Best Podcast Episodes About Small Business Administration

“… like suggestions of new restaurants to try, local events, shopping suggestions, and more. The new feature also ties into TikTok's push to attract small businesses to its app, not only as content producers, but as advertisers. This could help insulate it against further regulation and help it to claim, as Meta does, that it should not be reined in because so many small businesses rely on its services to reach their customers. TikTok notes that 7.5 million businesses currently use the app to reach global customers, and these businesses support more than 28 million workers, per a 2025 Oxford …” “… that the feed is meant to help users stay connected to their local community, and its posts are shown to people based on their location, the content's topic, and when the content was posted. This makes it a more current feed of local information, like suggestions of new restaurants to try, local events, shopping suggestions, and more. The new feature also ties into TikTok's push to attract small businesses to its app, not only as content producers, but as advertisers. This could help insulate it against further regulation and help it to claim, as Meta does, that it should not be reined in because so many small businesses rely on its services to reach their customers. TikTok notes that 7.5 million businesses currently use the app to reach global customers, and these businesses support more than 28 million workers, per a 2025 Oxford Economics report. The company also highlighted figures from the Small Business and Entrepreneurship Council, which found that 84% of TikTok's small business users said the platform helped grow their business, and 75% said TikTok helped them reach customers beyond their local area. In addition, another 74% said TikTok helps them connect with their local …” View more

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OpenAI's planned launch of an adult mode for ChatGPT has triggered significant backlash, leading to the firing of VP Ryan Biermeister who raised concerns about its potential harm. As she opposed the feature, claiming it could exacerbate unhealthy attachments to AI, several key researchers are now leaving the company, questioning its direction. This turmoil highlights the ethical dilemmas facing AI startups today.

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Tech Brew Ride Home · The “Covid Moment” For AI? · Feb 11, 2026

“… annual profits just from that one supercar in its first year. It could be even higher than 30%. Wow. Yeah. So it's critically important to the business. The business is in the supercars Yeah I mean this isn quite true but it is funny to think about this framing The Ferraris you see driving around occasionally those are just peanuts for their business And it's really all about the ones that are locked away in the garages that you don't see that actually make the money. If you think about the F40 and where Enzo was in his life and where the company was when they released that, I think they had …” “So I think that it's not crazy to assume that while that car will contribute 15% to revenues in the first 12 months, it's more like 30% of Ferrari's annual profits just from that one supercar in its first year. It could be even higher than 30%. Wow. Yeah. So it's critically important to the business. The business is in the supercars Yeah I mean this isn quite true but it is funny to think about this framing The Ferraris you see driving around occasionally those are just peanuts for their business And it's really all about the ones that are locked away in the garages that you don't see that actually make the money. If you think about the F40 and where Enzo was in his life and where the company was when they released that, I think they had no idea the business model they unlocked with this limited run supercar. Yeah, that's totally true. And where I imagine you were going with the Icona series is like, boy, wouldn't it be nice if we had a whole nother series with maybe not quite as good dynamics as that, but like pretty good dynamics. And gosh, it's a real shame we only have supercars …” View more

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Ferrari's new supercar could generate 30% of its annual profits in just the first year. Unlike other car manufacturers, Ferrari's unique production model allows them to launch four new models every year, creating a sense of exclusivity and demand that keeps their luxury brand thriving. This strategy not only boosts sales but also enhances their reputation as the pinnacle of automotive luxury.

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Acquired · Ferrari · Apr 13, 2026

“… So the answer would be no? Okay, gotcha. Yeah, I mean, I love real estate and I love investment property. I hate debt on it, and I really hate the Small Business Administration. They suck. And for you to get tied in with them and what that's going to do to the rest of your whole portfolio, all just to get a rental property, is the risk level that you just took on, neither one of you two are thinking about what you're doing here. The risk level is through the roof. So your investment guy's risk meter is broken. because the SB lock is always tied to other assets as well. And so you're putting all of that at risk to …” “… advisor presented me with the option of an SP lock He not pushing me towards it just presenting the options But I mean, if you've been listening to this, you know I don't borrow money or tell people to borrow money, right? That's right. Okay. So the answer would be no? Okay, gotcha. Yeah, I mean, I love real estate and I love investment property. I hate debt on it, and I really hate the Small Business Administration. They suck. And for you to get tied in with them and what that's going to do to the rest of your whole portfolio, all just to get a rental property, is the risk level that you just took on, neither one of you two are thinking about what you're doing here. The risk level is through the roof. So your investment guy's risk meter is broken. because the SB lock is always tied to other assets as well. And so you're putting all of that at risk to screw around with a rental property in California. Well, that's the thing. The rental property actually isn't in California. Oh, that's worse. It's a lot farther away in the island of Guam. Oh, that's really bad. It's my wife's grandmother's house. No, no, no, no, no, no, no, no, no, no. No, we do not have investment property that's long distance, and …” View more

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Dave Ramsey warns against pulling out an SBA loan for an investment property, especially one located in Guam. He emphasizes that investing in long-distance properties is risky and suggests that attempting to finance something unaffordable is a red flag. The conversation reveals the dangers of taking on debt for questionable investments, especially when it involves family properties.

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The Ramsey Show · Don’t Let a Lack of Boundaries Turn Into a Money Crisis · Mar 17, 2026

“… next area of focus for Airbnb to really kind of, the next area of growth for the company? No, that's exactly right. That's why you created the chief business officer role to do that expansion. The reason why we did the expansion is we need to help make the trip better overall. We know that when people travel to things like these events, they travel in larger groups, that there are a bunch of things that we can do to make it easier. That would be grocery delivery, airport pickup, and better. Wow, we're going to show you the best part of the community that you're visiting in. You're going to …” “… like a platform where you just kind of go and rent someone's apartment or house or something like that. But you guys have expanded into services and even things like, I think I read that you guys are piloting grocery deliveries as well. Is that the next area of focus for Airbnb to really kind of, the next area of growth for the company? No, that's exactly right. That's why you created the chief business officer role to do that expansion. The reason why we did the expansion is we need to help make the trip better overall. We know that when people travel to things like these events, they travel in larger groups, that there are a bunch of things that we can do to make it easier. That would be grocery delivery, airport pickup, and better. Wow, we're going to show you the best part of the community that you're visiting in. You're going to experience the community that you're staying in. You're going to stay in a local neighborhood. You can go to the local coffee shop. You can actually experience what the locals care about, and that's what the Experiences Service does. You can go to amazing restaurants, maybe a tour of a particular neighborhood. Maybe you see a unique boutique or clothing …” View more

Ridealong summary

Airbnb is transforming from a rental platform into a comprehensive travel service, engaging with major events like the Olympics and FIFA. By offering unique experiences and services, such as grocery deliveries and local tours, they aim to enhance the travel experience for groups and families. This strategy not only caters to event attendees but also seeks to attract solo travelers and business professionals with hotel partnerships.

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The Rundown · Airbnb Executive On Hotel Expansion, AI, and the Next Phase of Growth · Mar 15, 2026

“… requirements that they're subject to. And the big banks are okay because they can go tap the public markets for equity and raise capital. But our small community lenders will benefit most from doubling our manufacturing size because that will give them the capital base they need to grow. I love it. And so you're helping, again, millions of these owners. It's great for our society. How much money does the SBA give out or manage? How do you think about that? Yeah. So last year we put out a record in aggregate. We had a $100 billion impact in getting capital to Main Street. $45 billion of that …” “And yet our community lenders are saddled by Basel III, these global lending capital requirements that they're subject to. And the big banks are okay because they can go tap the public markets for equity and raise capital. But our small community lenders will benefit most from doubling our manufacturing size because that will give them the capital base they need to grow. I love it. And so you're helping, again, millions of these owners. It's great for our society. How much money does the SBA give out or manage? How do you think about that? Yeah. So last year we put out a record in aggregate. We had a $100 billion impact in getting capital to Main Street. $45 billion of that was through our lending programs. through our community lenders About billion went through our small business investment company SBIC program which is really a private equity portfolio that is investing in critical technology and other types of local manufacturing and other businesses And then we also have our SBIR program the innovation research, …” View more

Ridealong summary

The SBA recently reported a record $100 billion impact in capital distribution to small businesses, with $45 billion through community lenders. This funding not only supports local manufacturing but also addresses issues of fraud in government programs. As the SBA expands its reach, it plays a crucial role in fostering innovation and growth in the economy.

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Joe Lonsdale: American Optimist · Ep 145: SBA Administrator Kelly Loeffler on Exposing Billions in Fraud & What AI Means for Small Business · Mar 13, 2026

“… say this is what they thought they were going to do. What does that do? That suggests that there are way more people out there that should start businesses, but are probably not because someone told them they're not good enough or can't do it. Or it's self-talk that they don't believe they can do it on their own. It's so interesting because I think there are so many people that genuinely feel like that.” “… vision board, I think they'd say no. Not a single one of them. And I'm talking about Aloe and Viore and Fashion Nova and Gymshark and Figs and On Running. And I'm talking about like big, big brands. And I would say almost to a T, none of them would say this is what they thought they were going to do. What does that do? That suggests that there are way more people out there that should start businesses, but are probably not because someone told them they're not good enough or can't do it. Or it's self-talk that they don't believe they can do it on their own. It's so interesting because I think there are so many people that genuinely feel like that.” View more

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Many people believe entrepreneurship is out of reach, but Shopify's Harley Finkelstein suggests otherwise. He argues that today's low barriers to entry mean more people should give it a try, despite their doubts or lack of support. The success of major brands shows that many successful entrepreneurs never envisioned themselves as such, proving that anyone can start a business with the right mindset.

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Hot Smart Rich with Maggie Sellers Reum · How To Build A $1M Business For The Price Of A Manicure (escape the job you hate!) Shopify President Harley Finkelstein · Mar 25, 2026

“… you're doing subcontract work for a company of that scale all the way up to like a Microsoft or something like that. You're going to be working with smaller businesses that have unique needs and you need to be able to walk them through those things. I just think that's always going to, doing freelance work well, that's always going to be a huge part of it. Yeah. And just to give the listeners the benefit of kind of understanding the context, Like approximately how large are most of your clients in terms of like, you know, how big would the business be in like revenue or the number of people …” “… is subcontracting for a very large company like um i have a i have a good friend who had his own dev shop up until recently and you know they were up to a couple hundred employees and they would subcontract out stuff like from time to time, unless you're doing subcontract work for a company of that scale all the way up to like a Microsoft or something like that. You're going to be working with smaller businesses that have unique needs and you need to be able to walk them through those things. I just think that's always going to, doing freelance work well, that's always going to be a huge part of it. Yeah. And just to give the listeners the benefit of kind of understanding the context, Like approximately how large are most of your clients in terms of like, you know, how big would the business be in like revenue or the number of people working there? I know it's going to vary dramatically from industry to industry, and that's not necessarily a perfect proxy for how much software development work needs to be done for that company. But just give us an idea of like your typical clients like law firms. uh it our typical client if it's a professional service-based business that would be …” View more

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Freelancers often work with small to medium businesses, directly interacting with owners who deeply understand their company's needs. These businesses, like law firms and roofing companies, typically have fewer than 20 employees and unique software requirements. The rewarding part? Many of these owners evolve from solo entrepreneurs to thriving business leaders over time.

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The freeCodeCamp Podcast · #211 How to Land Freelance Clients with Small Business Whisperer Luke Ciciliano (Developer Interview) · Mar 13, 2026

“Okay, so a few months ago, I met with a big group of small business owners. And there was this moment when someone brought up these loan pitches, these never-ending calls and texts that they're getting promising quick cash. And so we were like, is this like predatory loans? And the room almost vibrated. Yes. I can talk for hours about everything. I get five calls a day. That is the story that no one's talking about in our country right now. But we will talk about it. Yes. So I heard someone say MCA. So …” “Okay, so a few months ago, I met with a big group of small business owners. And there was this moment when someone brought up these loan pitches, these never-ending calls and texts that they're getting promising quick cash. And so we were like, is this like predatory loans? And the room almost vibrated. Yes. I can talk for hours about everything. I get five calls a day. That is the story that no one's talking about in our country right now. But we will talk about it. Yes. So I heard someone say MCA. So that stands for Merchant Cash Advances. And this is the very shadowy financial world we are talking about. And the voice who said that is Joshua Esnard who got deeply in debt to these companies I visited him in North Carolina Hey how are you doing Good to see you He has a warehouse slash office near the Raleigh airport And Josh has this fun …” View more

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Josh's thriving business, The Cut Buddy, faced a staggering 152% increase in import tariffs, turning $230 in fees into over $4,600. This unexpected financial burden threatened to derail a decade of hard work and innovation. As Josh navigates this shadowy financial landscape, his story highlights the hidden challenges small business owners face today.

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The Indicator from Planet Money · The shadowy world of merchant cash advances · Mar 11, 2026

“A bigger budget line for travel is yet another hit for businesses this year, already dealing with uncertainty around tariffs and weakening consumer confidence. That's probably why business confidence, small business confidence in particular, is also in a bit of the doldrums right now. The National Federation of Independent Business, or NFIB for short, is out today with its February Small Business Optimism Index, which is down for a second straight month, although the numbers have rebounded from the sharp …” “A bigger budget line for travel is yet another hit for businesses this year, already dealing with uncertainty around tariffs and weakening consumer confidence. That's probably why business confidence, small business confidence in particular, is also in a bit of the doldrums right now. The National Federation of Independent Business, or NFIB for short, is out today with its February Small Business Optimism Index, which is down for a second straight month, although the numbers have rebounded from the sharp dive the index took last April after President Trump's Liberation Day tariffs were announced. Marketplace's Mitchell Hartman has more. NFIB's Optimism Index for February is just about average for the past 52 years that has been compiled. But one component of sentiment is running much higher than it has for decades, business uncertainty. Holly Wade …” View more

Ridealong summary

Despite facing rising costs and labor market challenges, small businesses are showing resilience by adding jobs at double the average rate. The NFIB's latest optimism index reveals a mix of concerns and cautious optimism among owners, as they adapt to economic pressures like inflation and tariffs. This adaptability highlights how quickly small businesses can respond to uncertainty in the market.

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Marketplace · Jet fuel prices soar as war continues · Mar 10, 2026

“… in too. So don't let me. I'm excited too. Okay. So what we have on the table today is the solution for ultra mobility. Okay. So that's where your business takes you. That's where you need to be. SIM card support, right? So the P12 supports SIM cards and support dual band Wi-Fi. It's lightning fast. Okay. So if you remember mobility devices of the past, this is nothing alike. There's a quad core processor, secure processor inside, and the screen is scratch resistant. Nice. Okay. So it's new or form for a longer time, protect your investment, which isn't that high to get started with because it's …” “… see, Ian, I don't know if you can get that. So yeah, we're running I-Pause-Pays on this little application. Can act as a standalone terminal. It can act as a pin pad. Lots of versatility there. Ron, I could keep going, but I know you want to jump in too. So don't let me. I'm excited too. Okay. So what we have on the table today is the solution for ultra mobility. Okay. So that's where your business takes you. That's where you need to be. SIM card support, right? So the P12 supports SIM cards and support dual band Wi-Fi. It's lightning fast. Okay. So if you remember mobility devices of the past, this is nothing alike. There's a quad core processor, secure processor inside, and the screen is scratch resistant. Nice. Okay. So it's new or form for a longer time, protect your investment, which isn't that high to get started with because it's really well priced and it's purposely made. Okay. So you can accept chip and pin. You can accept tap. Just the swipe is a thing of the past, so we get that. But it supports all types of transactions. It supports chip and pin and payment links and type in your card information or even display a QR for a customer to come and scan it. Okay. So you get …” View more

Ridealong summary

The P-12 device revolutionizes mobile payments with its ultra-portable design and versatile functionality. It supports all payment types, including chip, pin, and QR codes, making it ideal for farmers' markets and small businesses. With a competitive price point, it empowers merchants to keep more money in their local communities while competing against established services like Square.

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The Paycast Network · Payments Unplugged: From Seinfeld’s Black Card to Dejavoo’s Mobile Revolution · Feb 18, 2026

“… and it's just a very disruptive time. It's very disruptive, yeah. Then you had something like COVID, throw that in a couple of years ago. For many small businesses, they were really very local businesses before COVID. When COVID happened, it forced people to learn how to be virtual businesses, how to be remote businesses, to set up e-commerce shops and things like that. It forced a lot of small businesses into the world of technology, which may or may not have happened had it not been for COVID. Everyone was in the same place. You didn't have a choice. The companies that survived were the ones …” “… Revolution where big companies now provided work for people. Now, we're moving back to portfolio careers, right? We're farmers of data, I guess. I don't know, independent? But that's an interesting dynamic that we're experiencing. Absolutely, and it's just a very disruptive time. It's very disruptive, yeah. Then you had something like COVID, throw that in a couple of years ago. For many small businesses, they were really very local businesses before COVID. When COVID happened, it forced people to learn how to be virtual businesses, how to be remote businesses, to set up e-commerce shops and things like that. It forced a lot of small businesses into the world of technology, which may or may not have happened had it not been for COVID. Everyone was in the same place. You didn't have a choice. The companies that survived were the ones that learned how to utilize technology to further their business. It was an interesting time for a catalyst, right? For digital transformation.” View more

Ridealong summary

The COVID-19 pandemic forced small businesses to adapt or perish, pushing them to embrace technology and e-commerce like never before. This shift mirrors a historical trend where society moved from portfolio careers to industrial jobs and is now returning to a more independent work model. The businesses that survived learned to leverage digital tools, marking a significant transformation in the way we work.

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Embracing Digital Transformation · #326 The Rise of the Fractional Workforce · Feb 17, 2026

“Here's something most small business owners don't want to think about. What happens when something goes wrong? A customer slips, a shipment gets lost, a tool breaks, or someone gets hurt. You can lose thousands overnight. And most people only realize they need insurance after it's too late. That's why I like what Next Insurance is doing. They make getting business insurance as easy as ordering lunch online. You answer a few quick questions and Next figures out what you …” “Here's something most small business owners don't want to think about. What happens when something goes wrong? A customer slips, a shipment gets lost, a tool breaks, or someone gets hurt. You can lose thousands overnight. And most people only realize they need insurance after it's too late. That's why I like what Next Insurance is doing. They make getting business insurance as easy as ordering lunch online. You answer a few quick questions and Next figures out what you need. And just like that, you're covered. No phone calls, no headaches, no BS. Just fast, affordable coverage that actually protects you when things go sideways. Don't wait for a problem to remind you you're uncovered. Policies start as low as $29 a month. Get protected in minutes at nextinsurance.com. That's N-E-X-T insurance.com. We are in a state …” View more

Ridealong summary

Most small business owners only realize they need insurance after a disaster strikes. With Next Insurance, getting coverage is as easy as ordering lunch online, protecting you from potential losses. Embracing change is essential, as it allows businesses to adapt and thrive in a constantly evolving landscape.

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Creating Confidence with Heather Monahan · Confidence Classic: The 4 Phases of Change That Shape Your Next Level with Jason Feifer · Jan 06, 2026

“… Then where do we go? Okay. So, um, veteran was like a really tough, I like basically went like, I didn't have much money went like fully all in the business uh went into debt at one point in 2015 The business was having a tough time And then we ended up selling Ended up doing really well The business like completely hockey sticked in growth. And we got all the things figured out. And just like. Vetery. Vetery was. And then ended up getting approached by the world's largest recruiting company. The same groups you and I were talking about. The same groups we were trying to take out of business. and …” “Yeah. Then where do we go? Okay. So, um, veteran was like a really tough, I like basically went like, I didn't have much money went like fully all in the business uh went into debt at one point in 2015 The business was having a tough time And then we ended up selling Ended up doing really well The business like completely hockey sticked in growth. And we got all the things figured out. And just like. Vetery. Vetery was. And then ended up getting approached by the world's largest recruiting company. The same groups you and I were talking about. The same groups we were trying to take out of business. and they were like, oh, we want to acquire the company. And at the time, we were like, I was like completely dead broke and put everything out of the business. It was like, I think it was almost seven years in. And we were excited about an acquisition a year before that, $10 million from one of the big tech companies. And they came in at $110 million. …” View more

Ridealong summary

Brett Adcock shares the thrilling story of Vetery's unexpected acquisition by the world's largest recruiting company, Deco Group. After years of struggle and near bankruptcy, Vetery skyrocketed in growth and was approached with an offer that far exceeded previous expectations, culminating in a $110 million deal. This transformative moment marked a significant turning point in Adcock's career, leading him to seek even bigger ventures.

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The Shawn Ryan Show · #292 Brett Adcock - Shawn Ryan Meets a Humanoid Robot · Mar 30, 2026

“… We just danced around. Usually, we didn't stay that long. We'd go to a bonfire or something afterwards. But was it hard to date in a school that small? Was it hard to fall? What was the energy like that? I mean, you've known all these people your whole life. You know, they're, you know, what they're driving, you know, what their parents drive. I mean, yeah. I mean, you know how it is. Yeah. That's why I really, this town and this job is very similar to a small town. You get used to, um, like I kind of look at the fame thing like that now, you know, because when you're in a small town, like I …” “… the girl had to ask the guy, and he had to get him a shirt that matched. You had to do matching shirts or whatever. Uh-uh. You didn't have it? Uh-uh. But if y'all had to dance, what did y'all do with only that many students in the class? I don't know. We just danced around. Usually, we didn't stay that long. We'd go to a bonfire or something afterwards. But was it hard to date in a school that small? Was it hard to fall? What was the energy like that? I mean, you've known all these people your whole life. You know, they're, you know, what they're driving, you know, what their parents drive. I mean, yeah. I mean, you know how it is. Yeah. That's why I really, this town and this job is very similar to a small town. You get used to, um, like I kind of look at the fame thing like that now, you know, because when you're in a small town, like I would hear shit about me all the time. I'm like, I did what? You know? Yeah. And I don't know. You just get used to that. So do you think not being from Nashville is better coming into this kind of place? Like, is it does it when you get here, does it get so like is like the music scene, for lack of a better term? Is it more like is it so some type …” View more

Ridealong summary

Ella hilariously recounts her school dance experiences and the challenges of dating in a tiny class of 32. Her comparison of small-town life to newfound fame, complete with eye surgery anecdotes, keeps the laughs coming as she reflects on growing up with everyone knowing your business.

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This Past Weekend w/ Theo Von · #651 - Ella Langley · Apr 07, 2026

“Sometimes, same day, small businesses call the big bank, hey, I need help. I need $100,000. Payroll, things like that. Big banks says, nah, I'm sorry. Working with someone else right now. Can we call you next week? That's why Cardiff exists. It's for the small business. We're talking same day up to 500 grand. You don't deserve to be ignored because your business isn't a Fortune 500 company. You have needs too and Cardiff is here for those needs Go find out about it at …” “Sometimes, same day, small businesses call the big bank, hey, I need help. I need $100,000. Payroll, things like that. Big banks says, nah, I'm sorry. Working with someone else right now. Can we call you next week? That's why Cardiff exists. It's for the small business. We're talking same day up to 500 grand. You don't deserve to be ignored because your business isn't a Fortune 500 company. You have needs too and Cardiff is here for those needs Go find out about it at cardiff slash Jesse We be back No one knows what the future holds, but you deserve a weather app that can help. WeatherBug is easy to use and provides forecasts for your every need. From storm warnings to pollen levels, right at your fingertips. Get the fastest local alerts and comprehensive 10-day forecasts wherever you are. It's hyper-local, …” View more

Ridealong summary

Small businesses often find themselves overlooked by big banks, struggling to secure necessary funding. In contrast, Cardiff steps in to offer same-day financial support, providing up to $500,000 to help these businesses thrive. This highlights the growing need for tailored financial solutions in an increasingly competitive landscape.

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The Jesse Kelly Show · Islamic Terror STRIKES America — And Democrats Are to Blame · Mar 13, 2026

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In the next 50 to 100 years, 60-70% of inventions will be a collaboration between humans and AI, fundamentally changing how creativity is approached. While AI will drive a significant portion of innovation, there will still be a small percentage of breakthroughs that rely solely on human intuition. To stay relevant, individuals must start integrating AI into their daily processes, from planning vacations to tackling difficult conversations.

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Silicon Valley Girl · Reid Hoffman: We're Only 5% Into AI — Here's What Happens to Your Career in the AI Era · Feb 25, 2026

“And so it's unclear now, and Terry might have some better intelligence on this, where eBase goes from here. But I think with the building presence of business aviation at Friedrichshafen, it may become more permanent over time if eBase doesn't make some sort of return with a static display. This year, this has always been considered a general aviation trade fair, but the static line has increased just from last year. And some of the bigger jets now that I've seen today on the static line, the Dassault Falcon 6X, the Bombardier Global 6500, the Textron Aviation Cessna Citation Longitude. Textrun …” “And so it's unclear now, and Terry might have some better intelligence on this, where eBase goes from here. But I think with the building presence of business aviation at Friedrichshafen, it may become more permanent over time if eBase doesn't make some sort of return with a static display. This year, this has always been considered a general aviation trade fair, but the static line has increased just from last year. And some of the bigger jets now that I've seen today on the static line, the Dassault Falcon 6X, the Bombardier Global 6500, the Textron Aviation Cessna Citation Longitude. Textrun Aviation is a major presence here, and they use this venue for the European public debut of the Cessna Citation Ascend mid-sized jet. So Friedrichshafen especially this year has taken on more of a significance for the business aviation segment because there may not be any alternative going forward Yeah thanks Bill And you mentioned well Dassault of …” View more

Ridealong summary

The future of the eBase aviation show is uncertain after environmental protests severely impacted its 2023 edition. With growing competition from the Aero Friedrichshafen event, which is gaining traction in business aviation, eBase may struggle to recover. Exhibitors are already expressing fatigue over high costs and inadequate protections, raising questions about its viability moving forward.

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Aviation Week's Check 6 Podcast · Aero Friedrichshafen Steps Up · Apr 24, 2026

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Judy Faulkner, founder of Epic Systems, emphasizes that her success as a female entrepreneur is secondary to her unique business approach, which prioritizes employee satisfaction over profit maximization. In a candid discussion, she compares her company's culture to that of a whimsical grocery store, highlighting the importance of a positive work environment. Faulkner believes this philosophy contributes to Epic's high employee retention and attracts a vast number of applicants.

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Freakonomics Radio · 672. What Makes Judy Faulkner Run? · Apr 24, 2026

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Diana Marsh, a designer from New York City, faced the brutal reality of losing her fabric stores during the COVID-19 pandemic, going from seven locations to almost nothing. Instead of retreating, she opened Diana Marsh Couture, a welcoming space that even serves Prosecco. Diana shares her unexpected journey into the fashion world, including her first experience walking in Fashion Week, highlighting the importance of embracing uncomfortable situations for personal growth.

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The Determined Society with Shawn French · The Brutal Reality of Losing Everything in Business · Apr 06, 2026

“… in debt and consistently having problems. And we just kept funding it. And that is part of the immaturity of not understanding how to run a business. And I think that the fact that we went in as blind as we did, those mistakes were really like kind of transformative for us in the way that we run the company, but also in getting the company going. It took a really long time to get it going because of how little we knew and how hard it was to start it. Because building a brand is one thing. Building a business behind the brand is a totally other thing. And they have to happen in tandem. But …” “… say that that was just kind of the beginning of all of the things that would get us deeper into debt. We bootstrapped for a really long time. We didn't get an investment until 2021. Yeah. And so the brand before that time, I would say, was just consistently in debt and consistently having problems. And we just kept funding it. And that is part of the immaturity of not understanding how to run a business. And I think that the fact that we went in as blind as we did, those mistakes were really like kind of transformative for us in the way that we run the company, but also in getting the company going. It took a really long time to get it going because of how little we knew and how hard it was to start it. Because building a brand is one thing. Building a business behind the brand is a totally other thing. And they have to happen in tandem. But you don't know that if you don't know that. No, you don't. You sure don't. And then you look back later like, shit, I built a brand, didn't build a business. Yeah. And you're like, oh, God. And now look at us. It's like still hard, you know, still hard. So with that stake in the ground, what were the changes you had to make to then make it into a …” View more

Ridealong summary

STATE Bags faced significant challenges in its early years, including financial struggles and product issues. Co-Founder Jacqueline Tatelman shares how a pivotal rebranding and the right leadership helped transform the brand into a successful business model, emphasizing the importance of understanding both branding and business operations.

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Superwomen with Rebecca Minkoff · How One Simple Idea Turned Into an 8-Figure Business with STATE Bags' Jacqueline Tatelman · Apr 02, 2026

“… architects. And I just started sending emails to all of them and they had not spoken to this person. Victoria had published work in The Guardian, in Business Insider, New York Magazine, Rolling Stone, Africa, Vogue, Philippines.” “… in the ballpark of what you might say. So that was the first piece that I thought, okay, this is a made up story. And then I just kept looking. There were more. There was a story in Dwell that quoted like 10 prominent international designers and architects. And I just started sending emails to all of them and they had not spoken to this person. Victoria had published work in The Guardian, in Business Insider, New York Magazine, Rolling Stone, Africa, Vogue, Philippines.” View more

Ridealong summary

Nick discovers that a freelance pitch from Victoria Goldie is not just poorly written but possibly generated by AI, leading him down a rabbit hole of deception. As he investigates her previous work, he finds fabricated quotes and non-existent sources, raising questions about the integrity of her journalism. The eerie realization that AI might be behind these stories sends Nick on a quest to uncover the truth.

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Uncanny Valley | WIRED · Introducing Kill Switch Podcast: Uncovering an AI Journalist · Mar 18, 2026

“… You can do all these different things, but so many of the tasks can just be one shot. I was talking with a friend of mine who's, they have a family business and they just describe when they need marketing collateral. like a sign they just describe it to chat gbt and it just makes a it just one shots it now and there's no reason they don't really care there's so many business there's like yeah in tech you might create a generation and then like spent want to spend a bunch of time refining it and taking it from like 90 to 100 but the average small business is like you got me to 90 like we're good to …” “… here and we're still in the early I think Jordy, you were saying something? Oh, I'm just, I'm very curious to see how consumer AI impacts Canva overall. Sure. Because I think so many of the typical entry points in Canva, like Canva is a massive tool. You can do all these different things, but so many of the tasks can just be one shot. I was talking with a friend of mine who's, they have a family business and they just describe when they need marketing collateral. like a sign they just describe it to chat gbt and it just makes a it just one shots it now and there's no reason they don't really care there's so many business there's like yeah in tech you might create a generation and then like spent want to spend a bunch of time refining it and taking it from like 90 to 100 but the average small business is like you got me to 90 like we're good to go i don't need i don't need that extra horsepower yeah i think the the use cases where the last 10 is really like 90 of the value where you need to be like really able to iterate on it like pixel by pixel and not one shot it where there's like really difficult integrations you have to build where you can capture ambient new data like all of that …” View more

Ridealong summary

Generative AI is reshaping creative tools, allowing small businesses to generate marketing materials with just a description. As platforms like Canva face competition from AI-native startups, the need for iterative design diminishes, favoring quick, one-shot solutions. This shift is especially evident in video editing, where generative models could soon outpace traditional apps.

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TBPN · Nvidia Invests in Thinking Machines, Meta Acquires Moltbook, BYD F1 | Olivia Moore, David Paffenholz, Adam Goldstein, Max Junestrand, Allan McLennan, Jagdeep Singh, Scott Hickle · Mar 10, 2026

“But it is still a pretty big annual expense for a small business and it keeps going up There has been years where we redoing the premiums and renegotiating And there like a slight gulp in my throat where I just like oh wow I remember when it was only this much That number is getting definitely bigger. And the numbers got a lot bigger last year across the board. As indicator listeners know, premiums are skyrocketing for most people who get their health insurance through the Affordable Care Act …” “But it is still a pretty big annual expense for a small business and it keeps going up There has been years where we redoing the premiums and renegotiating And there like a slight gulp in my throat where I just like oh wow I remember when it was only this much That number is getting definitely bigger. And the numbers got a lot bigger last year across the board. As indicator listeners know, premiums are skyrocketing for most people who get their health insurance through the Affordable Care Act exchanges, also called Obamacare. That's because Congress failed to extend subsidies for those plans. But that's only part of the problem because there are actually many more people in the United States who get health insurance through their employers. That's the system for the majority of working age Americans. And those premiums are also surging. …” View more

Ridealong summary

Some employers are offering no-premium health insurance plans, which could save employees thousands annually. Companies like Boston Consulting Group are investing heavily in these benefits, believing that healthy employees lead to greater productivity and lower turnover. However, these plans may come with trade-offs, affecting salaries and other benefits.

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The Indicator from Planet Money · No healthcare premiums? In this economy?! Here's how. · Mar 09, 2026

“… to becoming a leader and they're really given Verizon and AT&T a run for their money. It's very, very clear to me. And then if you have a small business, we talked about this several years ago on the show. We had Mitch Goldstone from Scan My Photos on and he talked about this idea that he basically went to court against these credit card companies and got them to settle for $5.5 billion involving these credit card swipe fees. This went all the way back to 2005. Basically they claim that the card networks forced merchants to pay excessive interchange fees. That's the money that they pay …” “they've gone from kind of this company that was not necessarily a leader in the marketplace to becoming a leader and they're really given Verizon and AT&T a run for their money. It's very, very clear to me. And then if you have a small business, we talked about this several years ago on the show. We had Mitch Goldstone from Scan My Photos on and he talked about this idea that he basically went to court against these credit card companies and got them to settle for $5.5 billion involving these credit card swipe fees. This went all the way back to 2005. Basically they claim that the card networks forced merchants to pay excessive interchange fees. That's the money that they pay to the processor when you swipe your card. And by the way, that's why you're seeing all these small businesses. If you want to use your credit card, they're like, Oh, we're putting 3% extra on your bill because they don't like these fees that the credit card processors charge them. Now I have my own thoughts on that. My feeling is if you're doing …” View more

Ridealong summary

Small businesses are feeling the pinch from credit card swipe fees, leading some to charge customers an extra 3% for card payments. This issue traces back to a major $5.5 billion antitrust settlement against card networks over excessive interchange fees. As checks from this settlement roll out, business owners are finally seeing some relief, but the debate over payment methods continues.

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Rich On Tech · Google expands ID removal, cord-cutting tips & Bitcoin selloff analysis (161, February 14, 2026) · Feb 15, 2026

“A lot of business owners say they want to grow, but they hesitate the moment growth costs them control. Randy Reed runs a $2 million CPA firm with 14 team members. He's experienced, he's trusted, and he knows exactly how he wants things done, which is part of the problem. Because even with a solid team around him, Randy still finds himself buried in work that pulls him away from bigger leadership responsibilities. Not because no one else can do it, but because …” “A lot of business owners say they want to grow, but they hesitate the moment growth costs them control. Randy Reed runs a $2 million CPA firm with 14 team members. He's experienced, he's trusted, and he knows exactly how he wants things done, which is part of the problem. Because even with a solid team around him, Randy still finds himself buried in work that pulls him away from bigger leadership responsibilities. Not because no one else can do it, but because letting go feels risky. Today, Entree Leadership's head coach, John Falcons, sits down with Randy to unpack what's really keeping him in the weeds. And why sometimes the biggest ceiling in your business isn't capacity, it's you. If you've ever said, it's just easier if I do it myself, this conversation is going to challenge you. Check it out. Well, …” View more

Ridealong summary

Randy Reed, a CPA firm owner, realizes that his desire for control is stunting his business growth. Despite leading a $2 million firm with a solid team, he spends only 15-20% of his time on leadership, trapped in low-value tasks. To unlock potential growth, he must learn to delegate and focus on strategic leadership, a challenge many business owners face.

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The EntreLeadership Podcast · The Biggest Time-Wasting Mistake CEOs Make · Apr 27, 2026

“… use of a dollar? It's going to take a lot to convince me that it's something other than what I can go after and do. That doesn't mean it's always business profit-centered, like I don't always have to make money. Can I, Sam, go out and make an impact on the world by taking my own funds and building something special out of it that has an impact on whether it's mentorship, exposure, or whatever it is? So TBD, as you know, when you receive money, you spend a lot of time thinking about deploying and you don't want to rush into anything. But I would expect that the more meaningful deployment of my …” “… decide to give any away? Yeah, TBD on it. But one of the hardest things I have is I've thought about my impact. It's the same as I don't even know if I'll invest than other companies. It's not because I don't believe, it's like, what's the next best use of a dollar? It's going to take a lot to convince me that it's something other than what I can go after and do. That doesn't mean it's always business profit-centered, like I don't always have to make money. Can I, Sam, go out and make an impact on the world by taking my own funds and building something special out of it that has an impact on whether it's mentorship, exposure, or whatever it is? So TBD, as you know, when you receive money, you spend a lot of time thinking about deploying and you don't want to rush into anything. But I would expect that the more meaningful deployment of my capital is going to come through some personal effort in my life that I do to make an impact. Well, first of all, let me ask a boring question. Where did you invest it? The current money, where did you invest? Is it just boring index funds? Well, you know there's a difference between signing and closing. So you have to go through anti-regulatory. So …” View more

Ridealong summary

After selling his gummies business for over $1 billion, Chad Janis reflects on the complexities of deploying that capital. He shares insights on the regulatory hurdles and the unexpected opportunity that arose from a delayed deal, which ultimately led to a more advantageous investment for his company. This experience highlights the unpredictable nature of large transactions and the importance of strategic thinking in capital deployment.

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My First Million · This guy built a $1B+ brand in 3 years. The product? You'd never guess · Apr 24, 2026

“… So let's say if we can think creatively, we can start to get a glimpse of what maybe is possible. What do you see as the kind of first-generation businesses that you're excited about and what the second-order effect might be? Well, now we've got intelligence that is so rapid and non-latent. So you can solve problems way faster that are really complex. So one of the businesses that we've got that I'm most excited about is we pulled a team out of Tesla that built the supply chain automation platform at Tesla, which is super sophisticated and way beyond anything anybody had in the industry. And they …” “I love that story. So keep going. So let's say if we can think creatively, we can start to get a glimpse of what maybe is possible. What do you see as the kind of first-generation businesses that you're excited about and what the second-order effect might be? Well, now we've got intelligence that is so rapid and non-latent. So you can solve problems way faster that are really complex. So one of the businesses that we've got that I'm most excited about is we pulled a team out of Tesla that built the supply chain automation platform at Tesla, which is super sophisticated and way beyond anything anybody had in the industry. And they built this with ML in like 2017-ish. and we said, how would you like to build it today in AI? And what AI allows that team to do is solve a super complex problem really quickly, but also use agentic AI to understand the workflows of their clients super rapidly. So they just went into one of the biggest grocery delivery platforms in the country. I …” View more

Ridealong summary

Elon Musk's approach to goal setting is to aim for the seemingly impossible, such as increasing online car sales by 20 times, rather than simply improving from a position of weakness. This method forces teams to think innovatively and disruptively, leading to breakthroughs that wouldn't happen with conventional goals. By setting ambitious targets, Musk empowers his team to find unique solutions to complex problems.

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My First Million · Ex-Tesla President: The Unconventional Ideas Behind Tesla's Hypergrowth · Apr 09, 2026

“… we'll see more data pipelines being created, more data products being created, because I think historically data has been underutilized by businesses in terms of what's possible to do to run businesses more efficiently. And the economics will just create really strong motivation to do more. Yeah, you're seeing the references to Jevin's paradox a lot in the software space as well of people having that debate over our software engineers going to be completely obviated and removed as a result of AI. But instead, you're just seeing software engineers doing more. I know in my own work, there …” “… you see a lot of talk about Jevons paradox in the context of GPUs and AI and how the cost of AI dropping and people will be using more AI. I think the same is true for the output of data engineering. Because it's going to be cheaper to create data pipelines, we'll see more data pipelines being created, more data products being created, because I think historically data has been underutilized by businesses in terms of what's possible to do to run businesses more efficiently. And the economics will just create really strong motivation to do more. Yeah, you're seeing the references to Jevin's paradox a lot in the software space as well of people having that debate over our software engineers going to be completely obviated and removed as a result of AI. But instead, you're just seeing software engineers doing more. I know in my own work, there are dozens of different little scripts or tweaks or improvements or side projects that I've done in my day job that I wouldn't have otherwise bothered with. I actually just recently had a project that's been waiting on the shelf for about two years that I did a full rate up on. This is exactly how I would do it if I had the time. It's probably going …” View more

Ridealong summary

AI is revolutionizing data engineering, making it cheaper and easier to create data pipelines, leading to an explosion of data products. This shift is reminiscent of Jevons Paradox, where increased efficiency drives greater consumption. As AI takes on heavy lifting, we may see a consolidation of roles in data professions, empowering broader responsibilities for individuals.

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Data Engineering Podcast · The AI-First Data Engineer: 10–50x Productivity and What Changes Next · Apr 07, 2026

“… all over YouTube, TikTok, wherever you've been seeing. And what I'm interested in is I would have always loved to go to Stanford and go to Stanford Business School. There's probably a lot of people listening to this that kind of wonder what would it be like. And that would be cool to be able to go learn from the best at one of the best schools. Well, we get to kind of do that today. We have somebody who not only is out in the field, you've got a private equity fund that has almost like 20 billion in assets under management, but you also teach at Stanford. And I think today it'll be fun if we get to …” “… start with overhype. How about that? I feel like I can rule the world. I know I could be what I want to. I put my all in it like no days off. On the road, let's travel. All right, well, listen, we have Graham Weaver here today. You've seen this guy all over YouTube, TikTok, wherever you've been seeing. And what I'm interested in is I would have always loved to go to Stanford and go to Stanford Business School. There's probably a lot of people listening to this that kind of wonder what would it be like. And that would be cool to be able to go learn from the best at one of the best schools. Well, we get to kind of do that today. We have somebody who not only is out in the field, you've got a private equity fund that has almost like 20 billion in assets under management, but you also teach at Stanford. And I think today it'll be fun if we get to hang out and pick your brain and be students like we're in your class. I love it. looking forward to it. You know, what's funny is like you, I've watched your talks for a long time and they're amazing. How to live an asymmetric life was a really good one. How to live your full life. I think that wasn't the exact title one, but that was my takeaway …” View more

Ridealong summary

Graham Weaver shares how his private equity firm, Alpine, set an ambitious goal to become the top-performing fund, achieving over 5x returns on their investments in just six years. By focusing on treating people well and building a strong team, they not only hit their financial targets but also created a positive impact in their industry. This approach is a blueprint for success in today's competitive market.

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My First Million · We asked a $15B Investor how to survive the AI bubble · Apr 07, 2026

“… probably the coolest thing on the planet. I just love the idea of MNA, but me personally, I've turned into a greenfield organic machine. We grew the business. We'll do over 100 million of EBITDA and we grew 85% of it through organic, but I just got a really tight buy box. But in the future, I'm planning on really getting good at M&A. Why don't you give us a little story about yourself, your journey, how you got where you're at today? Yeah. Well, I'll first leave you with, I work with founders who are, they're great at building revenue, right, but have not yet built enterprise value. And I want to …” “… doing. It's an, it's an, it's an crazy, but thanks for being, having me on Tommy. No, it's going to be great, man. I, you know, MNA when I, I remember in 2017, I learned this crazy word and I've got it on my license plate. It's a arbitrage and it's probably the coolest thing on the planet. I just love the idea of MNA, but me personally, I've turned into a greenfield organic machine. We grew the business. We'll do over 100 million of EBITDA and we grew 85% of it through organic, but I just got a really tight buy box. But in the future, I'm planning on really getting good at M&A. Why don't you give us a little story about yourself, your journey, how you got where you're at today? Yeah. Well, I'll first leave you with, I work with founders who are, they're great at building revenue, right, but have not yet built enterprise value. And I want to theme it that way because that's what we're talking about. So my job is to help them turn a strong operating company into a transferable asset for that, what we call the inevitable exit. So with that framing, you know, my inspiration behind the book, Inevitable Exit, really falls within my work, but more so with a personal story with my father. And …” View more

Ridealong summary

Brian Franco shares a heartfelt story about his father's struggle with health and its impact on his thriving business, valued at $35 million. This personal journey inspired Brian to help other founders ensure their companies can endure beyond their ownership, emphasizing the importance of preparing for an inevitable exit on their own terms. His father's will to live amidst adversity serves as a powerful motivation for Brian's mission in business succession.

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The Home Service Expert Podcast · How to Scale and Exit Your Business (Brian Franco) · Apr 06, 2026

“… the things because MedV has also been criticized. It said it was a compounder of drugs. So I'm going to set aside all that. The fact is he built a business that was selling. And then in GLP-1, you have to say the right things with yourself, just like we had in life insurance. It was a regulated industry, and you have to do it right. So that first point I'm not going to get into. I'm just going to leave that there. But what this shows is that with AI, he created what? He created ad creators. And the agents did A-B testing. He used AI to create a customer service response. So where anybody …” “… thoughts on this story here with, you know, this fellow who built this Matthew Gallagher that built this company that could do 1.8 billion this year. Well, I have two sets of thoughts. So first is I'm going to set aside anybody who wants to send me the things because MedV has also been criticized. It said it was a compounder of drugs. So I'm going to set aside all that. The fact is he built a business that was selling. And then in GLP-1, you have to say the right things with yourself, just like we had in life insurance. It was a regulated industry, and you have to do it right. So that first point I'm not going to get into. I'm just going to leave that there. But what this shows is that with AI, he created what? He created ad creators. And the agents did A-B testing. He used AI to create a customer service response. So where anybody responded, you immediately got an email back. Thank you, Vinny, for your interest. Here's the information you were looking for. So it shows that you can use these agents to do chores of the basic stuff to build a business. Now, here's what AI doesn't do. It's not going to select an industry for you. It's not going to make you incredibly smart about that …” View more

Ridealong summary

Matthew Gallagher built a $1.8 billion company using AI to streamline operations and customer service in the healthcare sector. His success illustrates that while AI can enhance business efficiency, human oversight and industry knowledge are crucial for navigating regulations. This case highlights the importance of combining technology with thoughtful leadership in entrepreneurship.

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PBD Podcast · US Pilot RESCUED + Trump's BRUTAL Iran Warning | PBD #771 · Apr 06, 2026

“… not fun to what? It's the worst part of the gig. Oh, it's what? Taxes. Amen, brother. He got it. How many times, Brian, have you sat down with a small business owner? They launch their first business. They start their first side gig. And maybe they're not laying in front of the couch crying, but that same realization. Holy cow, why on earth do I owe so much taxes? I finally just made my business profitable. It is something that if you do not plan for it and don't know that it's coming, you may also find yourself in tears. Probably a proud parent moment though. Like, okay, he's going to be a …” “… to go do a new W-4 Change the numbers And then grip and rip and let it go Until the next tax season Where's all your money gone, Donnie? Taxes. Uh-oh, he's crying. Let me fix my houses. But it's okay. It's part of the gig. Is it monopoly? It is. It's not fun to what? It's the worst part of the gig. Oh, it's what? Taxes. Amen, brother. He got it. How many times, Brian, have you sat down with a small business owner? They launch their first business. They start their first side gig. And maybe they're not laying in front of the couch crying, but that same realization. Holy cow, why on earth do I owe so much taxes? I finally just made my business profitable. It is something that if you do not plan for it and don't know that it's coming, you may also find yourself in tears. Probably a proud parent moment though. Like, okay, he's going to be a hard worker and not want to pay taxes. He an American Here how to never pay tax again So this is what I would do if I was solely basing my decisions off of tax and nothing else First I would become a real estate professional under IRS definitions because they receive by far the best tax advantages Two is I would purchase real estate. And third is …” View more

Ridealong summary

You can legally avoid paying taxes by becoming a real estate professional and utilizing specific strategies like 1031 exchanges and cost segregation studies. This approach allows you to defer capital gains and offset ordinary income, but it requires careful planning and an understanding of IRS rules. Many small business owners are caught off guard by their tax liabilities, but with the right knowledge, you can navigate these waters successfully.

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Money Guy Show · Financial Advisors React to the BEST and WORST Tax Advice · Apr 06, 2026

“And so that is a lot of what I focus on, which is, you know, if you focus your business on being human centric and your employee first, ultimately, the numbers pay off in volume. And there are lots of reports that talk about that. Yeah, I'm glad you brought that up because I think that's an important aspect, right, is if you're not just worried about hiring people and a number, but you actually engage your employees, like you were mentioning, they're going to produce more for you. They're going to stay engaged in the company as …” “And so that is a lot of what I focus on, which is, you know, if you focus your business on being human centric and your employee first, ultimately, the numbers pay off in volume. And there are lots of reports that talk about that. Yeah, I'm glad you brought that up because I think that's an important aspect, right, is if you're not just worried about hiring people and a number, but you actually engage your employees, like you were mentioning, they're going to produce more for you. They're going to stay engaged in the company as well. It's almost like in big corporations, you can easily get lost in the shuffle and basically hide. and we saw that when um elon musk came through twitter we saw that when elon musk came through the federal government and doge happened they got rid of people that were working other jobs and still taking a paycheck not engaged at all in their in …” View more

Ridealong summary

A staggering 79% of employees are disengaged, costing companies significantly in lost productivity. Engaging employees not only boosts morale but also leads to one-third less turnover and eight times more revenue per employee. This shows that investing in people is far more beneficial than simply cutting staff.

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Embracing Digital Transformation · #339 The 8X Revenue Secret: Engaging Employees Like a Coach · Apr 02, 2026

“… on the cybersecurity subreddit. By the way, we do those CISO series, we do them every month. Companies are demanding that security demonstrate business value rather than just pouring money into continuous improvement exercises. Answers for showing ROI varied. Some suggested financial risk modeling that dovetails with cyber risk. Another relied on quantitative frameworks such as FAIR, focusing on whether controls reduce annualized loss expectancy. And these methodologies exist, are well documented and debated. And I gonna start with you Jason on this Where do you think we should show the value …” “… Z-E-P-O dot A-I. And let them know you heard about them from the CISO series. It comes down to the fundamentals. Explaining ROI for cyber is a dark art, said Defense In-Depth co-host Steve Zalewski in a recent CISO series AMA, that's an Ask Me Anything, on the cybersecurity subreddit. By the way, we do those CISO series, we do them every month. Companies are demanding that security demonstrate business value rather than just pouring money into continuous improvement exercises. Answers for showing ROI varied. Some suggested financial risk modeling that dovetails with cyber risk. Another relied on quantitative frameworks such as FAIR, focusing on whether controls reduce annualized loss expectancy. And these methodologies exist, are well documented and debated. And I gonna start with you Jason on this Where do you think we should show the value of cyber And I think actually the answer varies depending on what industry you in Can we show that it helping us make money Or is it better ROI about demonstrating the cost of not doing it I mean, where do you begin to determine that? I would never start with the cost of not doing it. Honestly, I don't think that would go over very well. And …” View more

Ridealong summary

In today's cybersecurity landscape, your people are no longer the weakest link; they're your greatest asset. Companies must shift from mere compliance to actively enhancing employee capabilities through platforms like Zippo Intelligence, which provides tailored training and measurable security metrics. This change not only strengthens defenses but also demonstrates the tangible ROI of cybersecurity investments.

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CISO Series Podcast · Do You Think These Compliance Boxes Check Themselves? (LIVE in Clearwater, FL) · Mar 31, 2026

Ridealong summary

Kyle Hjelmeseth reveals that his journey from managing one client to overseeing over 100 creators is rooted in love and integrity. He emphasizes that prioritizing genuine relationships and serving others led to a surprising 75-80% referral rate, proving that caring can drive financial success in the creator economy. This unexpected outcome challenges traditional business norms and showcases the power of community in the industry.

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Technically Creative by KoobrikLabs · Influencers into Industry: The Rise of the Creator Economy With Kyle Hjelmeseth · Mar 31, 2026

Ridealong summary

Jeff Bezos transformed Amazon's meetings by banning PowerPoint presentations and requiring a structured narrative instead. This approach ensures clarity and alignment among team members, allowing for more effective communication and decision-making. By prioritizing structured writing, Bezos demonstrated that clear thinking leads to clear speaking.

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BigDeal · #133 Be ARTICULATE and Speak SMARTLY: Communicate Like A Pro · Mar 31, 2026

“… Yeah. It's like, this is like literally like things that people just are not focusing on. Right. Give me another one. I think it happens in a lot of businesses. Like at Lululemon, when I asked the question, where do we make our money? Yeah. Lululemon has historically made their money in bottoms, not tops. And so it's the pant wall. That's where they make their money. Yeah. So then you'd ask the question, okay, why do we have all the rest of this extraneous stuff going on then? Totally. Because it's just diluting profitability, to your point. And it's like the $20 deal versus the $1,000 deal. So like …” “… that a million dollars versus 20 bucks you still working Like the amount of work is usually the same. That's a great example. Exactly. The amount of work is the same. And so why not apply that work to the profit pool? Super simple. Exactly. Yeah. It's like, this is like literally like things that people just are not focusing on. Right. Give me another one. I think it happens in a lot of businesses. Like at Lululemon, when I asked the question, where do we make our money? Yeah. Lululemon has historically made their money in bottoms, not tops. And so it's the pant wall. That's where they make their money. Yeah. So then you'd ask the question, okay, why do we have all the rest of this extraneous stuff going on then? Totally. Because it's just diluting profitability, to your point. And it's like the $20 deal versus the $1,000 deal. So like this happens all over businesses because businesses get complex over time and nobody comes along. It's like a garden that gets weeds and nobody comes along to weed the garden. And I feel like my job is come weed the garden. Like let's figure out which of these plants matter and let's water the heck out of them and let's whack the heck out of …” View more

Ridealong summary

Lululemon makes most of its profits from selling bottoms, not tops, which raises the question of why they offer so many other products. By focusing on their most profitable items, they could streamline operations and enhance profitability. This strategy mirrors a broader business lesson: simplifying can lead to greater success.

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Habits and Hustle · Episode 541: Jon McNeill: Why “Less” and “Simple” are the Smartest Growth Strategies · Mar 31, 2026

“… ground, you have to talk to the people actually making this economy go. That's the assignment at Marketplace Mitchell Hartman got this morning, the small business economy yet to come. For a while now, we've been hearing that employers are hesitant to add workers, also hesitant to lay off the ones they've already got. And that is what I heard from small business owners I connected with today. We're hiring right now because we're replacing people. But no, we're not looking to increase employment. That's Adam Orman in Austin, Texas. He's got two Italian restaurants, one casual, one more upscale. …” “Talking to analysts and economists about what's going on out there, as Sam Fields was just doing, is all well and good, and we do a fair amount of that because it's valuable. But sometimes if you really want to get into sense of things on the ground, you have to talk to the people actually making this economy go. That's the assignment at Marketplace Mitchell Hartman got this morning, the small business economy yet to come. For a while now, we've been hearing that employers are hesitant to add workers, also hesitant to lay off the ones they've already got. And that is what I heard from small business owners I connected with today. We're hiring right now because we're replacing people. But no, we're not looking to increase employment. That's Adam Orman in Austin, Texas. He's got two Italian restaurants, one casual, one more upscale. And his headcount now is about 50 employees. It has shrunk a little bit for a number of reasons. Inflation-weary consumers are dining out and drinking less. Plus... It continues to be very difficult to hire. A lot of people left the restaurant workforce during the pandemic. And then over the last year and a half we seen a lot of immigrants leave the …” View more

Ridealong summary

Small business owners are facing a tough hiring landscape, often replacing existing employees rather than expanding their teams. Factors like inflation and a shrinking workforce, especially among immigrants, are causing many to hesitate on new hires. Despite these challenges, some entrepreneurs remain optimistic about growth, as evidenced by one founder's recent hiring despite overall industry struggles.

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Marketplace · Triple-digit trouble · Mar 30, 2026

Ridealong summary

You don't have to like the founders you invest in, according to Marc Andreessen. He argues that personal emotional needs shouldn't interfere with professional relationships, citing examples of successful but unlikable figures in history. Instead, a productive working relationship is what matters most, regardless of personal connections.

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The a16z Show · Marc Andreessen on Evaluating Founders and AI's Consumer Surplus · Mar 30, 2026

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A culture of innovation thrives on risk-taking and embracing failure, rather than just improving existing models. Brian Solis emphasizes that true innovation is about creating new value, not merely doing things better or cheaper. This mindset shift is crucial for businesses to keep pace with the evolving landscape of technology like AI.

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Digital Disruption with Geoff Nielson · AI is Losing Ground: Futurist Brian Solis on Why AI Adoption is Failing · Mar 30, 2026

“… a it's a crazy different kind of expense. Right. We just maybe we do need to just align our goals. One more question for you, Christy. Ken, this business is so new when it starts really taking off. Right. Because it sounds like you've done it for so long. You're obviously very good at it. Do you have some income expectations of where you think it will – before it's like a fledgling business. What's the goal you're working towards? Because I think maybe that might help even in terms of how we're planning some of this. Currently – so I mean we've already hit $100,000 in sales in one week of being …” “But, you know, now that we have something together like kids, I guess we've always had our marriage. But now we have this. I mean, it's a it's a crazy different kind of expense. Right. We just maybe we do need to just align our goals. One more question for you, Christy. Ken, this business is so new when it starts really taking off. Right. Because it sounds like you've done it for so long. You're obviously very good at it. Do you have some income expectations of where you think it will – before it's like a fledgling business. What's the goal you're working towards? Because I think maybe that might help even in terms of how we're planning some of this. Currently – so I mean we've already hit $100,000 in sales in one week of being officially registered with different suppliers. So that's revenue. So that brings in about – right now we're at $12,500 in commission in one week. And then most of that currently is mine. My new agents are just starting out. But that's in just one week, which is just wild. It's awesome. So I'm really, and with just myself and currently two agents …” View more

Ridealong summary

Nathan and Crissi are navigating the challenges of launching a new business while balancing family life. With an impressive $100,000 in sales in just one week, Nathan sets an ambitious goal of reaching $2 million in net revenue within five years, contingent on hiring the right agents. The discussion reveals the potential for growth and the realities of business expansion in the travel industry.

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Money Guy Show · Will Their Unique Financial Structure Hold Up? | Making a Millionaire · Mar 30, 2026

“… it into a lot of growth initiatives that might not even be the best for the company in the long run. So the mindset of spend now and figure out the business plan later, we have seen those examples with companies like WeWork or Quibi where they started out really strong, had a lot of funding from investors, but then flamed out towards the end. Yeah. And a big part of this is all about incentives. So in order to understand incentives, you need to really understand the way that VCs are typically set up. So venture capital funds, they actually invest in a whole portfolio of startups, right? So …” “… grow your company at this incredible rate and so i think that's why a lot of startups have this sort of grow at all cost mentality where they're going to take all the money that was invested in them by the venture capitalists and sort of like throw it into a lot of growth initiatives that might not even be the best for the company in the long run. So the mindset of spend now and figure out the business plan later, we have seen those examples with companies like WeWork or Quibi where they started out really strong, had a lot of funding from investors, but then flamed out towards the end. Yeah. And a big part of this is all about incentives. So in order to understand incentives, you need to really understand the way that VCs are typically set up. So venture capital funds, they actually invest in a whole portfolio of startups, right? So typically they have like 20, 30, 40, hundreds of startups that are all a part of their portfolio. And what they're really looking for is a very small portion of them to become 100X, 1000X companies. Those are the sort of like unicorns that you've heard about before. And they already know or it's sort of baked into their expectation that the vast majority …” View more

Ridealong summary

Venture capital often pressures startups to grow rapidly, leading to potentially harmful decisions. Many founders feel compelled to chase massive growth at all costs, which can result in the downfall of companies like WeWork and Quibi. It's crucial for entrepreneurs to evaluate whether VC investment is truly the right path for their business.

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Tiger Sisters · How to Sound Smart About Money in Any Room · Mar 30, 2026

“I fucking love it dude We got one more for you dog Let bring on home We got a question number three guys Andy I started my business because I believed in the work Now I spend most of my time selling negotiating marketing and dealing with people It feels like I don actually get to do the thing I good at anymore Is that just what growth requires or is there a smarter way to structure this? Does it say what he does? It does not. All right. Okay. Okay. So You gotta understand something Whatever your skill set is Let's say you're a woodworker And you're fucking The most amazing …” “I fucking love it dude We got one more for you dog Let bring on home We got a question number three guys Andy I started my business because I believed in the work Now I spend most of my time selling negotiating marketing and dealing with people It feels like I don actually get to do the thing I good at anymore Is that just what growth requires or is there a smarter way to structure this? Does it say what he does? It does not. All right. Okay. Okay. So You gotta understand something Whatever your skill set is Let's say you're a woodworker And you're fucking The most amazing woodworker On the fucking planet And you want to turn this woodworking Into a business Obviously you have a great product And obviously you're skilled at it. Once you start to turn something that you really love into a business, for at least temporarily, it will pull you away from that craft. Okay. And you'll have to learn this whole new set of …” View more

Ridealong summary

Transitioning from a craft to a business often means sacrificing the joy of creation for the demands of management. Andy explains that while you may need to step away from your passion initially, successful entrepreneurs like Jesse James eventually find a way to return to their craft. This journey requires learning new skills and building a team to support your vision.

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REAL AF with Andy Frisella · 1014. Q&AF: Regaining Your Edge, Rewarding Yourself Responsibly & Working In Vs On The Business · Mar 30, 2026

“… I said, I'm going to take a year off, and I really want to be intentional. And so now I'm in that second year, and I'm starting to explore different business ideas. And it's been all over the board. I didn't sell with the idea of, I want to go do this specifically. it was more i've got to a point where i'm not learning anymore myself and we're in 5 000 cities if i go scale another 5 000 it's gonna be the same for me yeah um we also we're getting so big that we're gonna have to go public if we didn't find a you know a buyer and for me like once you become public then you've got to stay with business …” “Are you planning on starting another company ever again? Yeah. Yeah. This last year, I said, I'm going to take a year off, and I really want to be intentional. And so now I'm in that second year, and I'm starting to explore different business ideas. And it's been all over the board. I didn't sell with the idea of, I want to go do this specifically. it was more i've got to a point where i'm not learning anymore myself and we're in 5 000 cities if i go scale another 5 000 it's gonna be the same for me yeah um we also we're getting so big that we're gonna have to go public if we didn't find a you know a buyer and for me like once you become public then you've got to stay with business for a long period of time you can't just sell all of your stock at once or you know breaks out the market and i thought ah do i really have another 10, 20 years in me to do this. And I'm like, I think I'm ready for a different challenge. So it was a way to be able to get all the money out at once, help everybody have an incredible payday. And I …” View more

Ridealong summary

Surrounding yourself with the right mentors can dramatically impact your entrepreneurial journey. David Royce emphasizes the importance of peer mentors and entrepreneurship groups like YPO, which provide invaluable support and diverse perspectives. He warns against tying your identity solely to your business, highlighting the need for personal growth and connection.

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Young and Profiting with Hala Taha (Entrepreneurship, Sales, Marketing) · David Royce: How to Turn a Boring Idea into a 9-Figure Business | Entrepreneurship | E392 · Mar 30, 2026

“And so as far as the operation of a business where that unit economics and the amount consumed is core to how the business actually generates revenue, what are some of the ways that that poses unique operational challenges that are different from businesses that are in the either physical goods or services industries so once consumption is a unit of cost what is a unit of revenue right one thing is very important is that your operations becomes a real-time optimization problem why i say …” “And so as far as the operation of a business where that unit economics and the amount consumed is core to how the business actually generates revenue, what are some of the ways that that poses unique operational challenges that are different from businesses that are in the either physical goods or services industries so once consumption is a unit of cost what is a unit of revenue right one thing is very important is that your operations becomes a real-time optimization problem why i say that because now you're using consumption to drive everything so consumption is part of your operations every day that's why that's the real-time optimization Problem is you are juggling with all the metering data on the cost attribution, right? Okay, customer is using this what is the cost of serving this customer? You are always looking into this …” View more

Ridealong summary

In consumption-based business models, accurate metering is crucial to prevent revenue leakage. As consumption drives operations, businesses must optimize real-time data management and billing processes to ensure they capture all revenue accurately. Without strong governance and efficient workflows, companies risk losing significant income due to inaccuracies in consumption measurement.

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Data Engineering Podcast · Treat Metering Like Finance: Building Data Platforms for Consumption Economics · Mar 29, 2026

“… this thing. Trust is the hard part. So there's two parts of two ways that we're solving this. You know, they always say like, it's like when you're small, it's easy to have a relationship with your customers, but there's no way you're going to sit on the phone and call everyone of your customers and say, thanks for booking with us. Hey, it's Tommy. Thanks for booking with us. Hey, it's Tommy. Thanks for booking with us, right? There's a point in your business where you can't be that guy. You can't be, oh, that's my HVAC guy. That's my garage door guy. You can't be that guy for everybody because …” “… people understand what that does. That's the base. So there's two parts to this. There's two major parts. And there's the trust is what we're really trying to gain here. And that's the difficult part of all that in this sea of commodities and all this thing. Trust is the hard part. So there's two parts of two ways that we're solving this. You know, they always say like, it's like when you're small, it's easy to have a relationship with your customers, but there's no way you're going to sit on the phone and call everyone of your customers and say, thanks for booking with us. Hey, it's Tommy. Thanks for booking with us. Hey, it's Tommy. Thanks for booking with us, right? There's a point in your business where you can't be that guy. You can't be, oh, that's my HVAC guy. That's my garage door guy. You can't be that guy for everybody because you're too big. And so there's this coldness that comes from scaling where you lose that authenticity. and so the way that we combat that and I call you know it's like scaling authenticity is very difficult thing and and the way that we do that is through technology you can take uh your authenticity and say it to a video to a camera once and now …” View more

Ridealong summary

Home service businesses can maintain authenticity even as they scale by using technology for customer engagement. By sending personalized thank-you videos through iMessage, companies can build trust and connection without losing that personal touch. This innovative approach not only keeps customers engaged but also significantly boosts response rates.

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The Home Service Expert Podcast · How AI Is Closing Deals for Home Service Businesses with Chiirp (Ryan Fenn) · Mar 27, 2026

“… like books written about it What did you think in that time was was ahead for the company The big debate was like the sort of debate over the business model for Twitter. What was the team that we needed? And what was the path that we should pursue for a business model for Twitter? And Ev had a lot of me as well. We had a lot of hesitancy about the ads only approach to the business model for Twitter because we had worked at Google and were not super wild about the user experience of content targeted ads and advertising and social media. It was like, you know, all this stuff about like, you …” “… that like I wasn't going to support Jack as a leader at the company. And this is an important part of all this, too. At this time it is a relatively chaotic managerial like there just a lot of like shuffling around Oh yeah And like the drama of Twitter like books written about it What did you think in that time was was ahead for the company The big debate was like the sort of debate over the business model for Twitter. What was the team that we needed? And what was the path that we should pursue for a business model for Twitter? And Ev had a lot of me as well. We had a lot of hesitancy about the ads only approach to the business model for Twitter because we had worked at Google and were not super wild about the user experience of content targeted ads and advertising and social media. It was like, you know, all this stuff about like, you know, the surveillance, you know, surveillance capitalism and, you know, you are the product, like all of that stuff is true. Like, it's just true. Like, you know, we haven't come up with a better business model to replace it. It turns out that business model is both high margin and high volume. They get remains the dominant way to monetize content on …” View more

Ridealong summary

Twitter played a crucial role in Donald Trump's 2016 presidential election victory, according to former Twitter executive Jason. He reflects on how the platform's unique dynamics shaped political discourse, leading to a broader conversation about social media's influence on civic life, particularly in the wake of Trump's rise. This pivotal moment highlighted the tension between Twitter's cultural impact and its business model challenges.

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Galaxy Brain · What Is Twitter’s Legacy, 20 Years Later? · Mar 27, 2026

“… we have to be really excited about and striving for and helping to create as well is, I want my nine-year-old to be able to create a lawn service business and use robots. or yeah for sure if you know do we have a chef we call that job shepherd yeah shepherd for robots i have a cynical take on it i'm guessing okay figure no no just on the figure i'll figure something i mean i i think the most generous take is what he said hey we tried to use these lms it doesn't work for our robots okay fair enough you make your own um cynical take uh which would be hey the valuations of open AI, the valuation of …” “But I think the vision of the future we have to be really excited about and striving for and helping to create as well is, I want my nine-year-old to be able to create a lawn service business and use robots. or yeah for sure if you know do we have a chef we call that job shepherd yeah shepherd for robots i have a cynical take on it i'm guessing okay figure no no just on the figure i'll figure something i mean i i think the most generous take is what he said hey we tried to use these lms it doesn't work for our robots okay fair enough you make your own um cynical take uh which would be hey the valuations of open AI, the valuation of Claude, you know, getting to 800 billion, 400 billion, I'm sure Claude's next valuation will go from 350 billion to 800 and be neck and neck with open AI. So I believe they'll probably be similarly valued. So if they're going to be worth 900 billion and XAI as part of SpaceX is worth 2 trillion I need to be in that group not in the robotics group …” View more

Ridealong summary

Chasing validation and mimicking successful companies can lead to mediocrity instead of excellence. Founders must focus on delivering core value to customers rather than getting lost in the hype of market trends. True success comes from hard work and a commitment to meaningful contributions, not just flashy announcements.

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This Week in Startups · $2.5B Chip Heist, The Future of American AI, and Purpose-Built Robots | This Week in AI Ep 6 · Mar 25, 2026

“so when I walk in and say I'm a b2b software investor at the seed stage and you come to me with a life sciences business at the growth phase you might have a sick business I can't do that deal right so it's like so just you have to there's a qualification there and I think the other thing um yeah and there's like fun math associated with it um and i would also say there's like a little bit of a capitalization fit like i said at the beginning like there's a lot of people that show up with a great idea but i'm like don't raise venture capital yeah because there's …” “so when I walk in and say I'm a b2b software investor at the seed stage and you come to me with a life sciences business at the growth phase you might have a sick business I can't do that deal right so it's like so just you have to there's a qualification there and I think the other thing um yeah and there's like fun math associated with it um and i would also say there's like a little bit of a capitalization fit like i said at the beginning like there's a lot of people that show up with a great idea but i'm like don't raise venture capital yeah because there's certain ideas that should be bootstrapped there's certain ideas that should be private equity and that's kind of a surprise too that was one of the biggest things that i had to learn the hard way in my career. So I was telling you, I scaled my business and I ended up selling it. Coming out of COVID a whole bunch of stuff happening Just over 24 …” View more

Ridealong summary

Selling your business can lead to unexpected challenges, especially if you choose the wrong buyers. Many entrepreneurs overlook critical integration questions that can cause friction post-sale, leading to a misalignment of goals and expectations. Understanding these pitfalls can save you from a tumultuous transition and ensure a smoother journey after the deal closes.

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Finding Peak w/ Ryan Hanley · Former HubSpot CRO on the Math Nobody Uses to Scale | Mark Roberge · Mar 25, 2026

“… super cheap. You know, I've been in million dollar booths. I've been in, you know, all kinds of, And then, you know, it depends on the scale of the business that you have, right? What kind of investment you want to make. But I think one of the things that we talk about, we talk about the trade show triangle. And it's like there's different levels of exhibitors. And so many are in the bottom part of that triangle where they are what we call a booth buyer. They buy a booth, they show up, and they wait. And they buy into that myth, if you build it, they will come, which is from Field of Dreams. And if …” “… you have a solution for this big problem. I want to hear all about it. One solution, maybe not just one. We're going to have like a kind of a multi-pronged attack and look at that. I mean, 50 grand and it depends on the industry. That could be super cheap. You know, I've been in million dollar booths. I've been in, you know, all kinds of, And then, you know, it depends on the scale of the business that you have, right? What kind of investment you want to make. But I think one of the things that we talk about, we talk about the trade show triangle. And it's like there's different levels of exhibitors. And so many are in the bottom part of that triangle where they are what we call a booth buyer. They buy a booth, they show up, and they wait. And they buy into that myth, if you build it, they will come, which is from Field of Dreams. And if you believe that, you're dreaming that this is going to work for you, right, at a trade show. So understanding that engagement is so key, understanding that it's going to take some energy, some being proactive. You know, there's a lot of things that you need to do to be able to make your investment worthwhile. And those who do crack that code are …” View more

Ridealong summary

Many companies waste $50,000 or more at trade shows by sending their least effective salespeople, hoping for success. Anders Boulanger reveals that the key to maximizing your investment lies in proactive engagement, rather than the outdated belief that 'if you build it, they will come.' With the right strategies, exhibitors can achieve 3x to 4x ROI on their trade show investments.

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The Vault Unlocked · Why Your Trade Show ROI Is Suffering and How to Fix Your Sales Team's Booth Strategy · Mar 25, 2026

“… and then they charged me forty thousand dollars and I've never seen them again right that is the that is the consulting doom loop sounds like a good business model though sounds like a pro that now that would be a profitable business model, although you're always chasing clients. So how did you, because I think enterprise sales or being a founder and looking at enterprise could be game changer for a lot of people. Like a lot of, you know, for me starting out, I was looking at, you know, smaller. And then as my confidence grew, I then started looking at bigger and bigger because obviously those are …” “… almost anti-consultant. Like if you think big four, you think, okay, I paid them a lot of money. they came in and said a bunch of words that I don't understand uh then they created a slide deck that said I should reduce costs and increase revenue uh and then they charged me forty thousand dollars and I've never seen them again right that is the that is the consulting doom loop sounds like a good business model though sounds like a pro that now that would be a profitable business model, although you're always chasing clients. So how did you, because I think enterprise sales or being a founder and looking at enterprise could be game changer for a lot of people. Like a lot of, you know, for me starting out, I was looking at, you know, smaller. And then as my confidence grew, I then started looking at bigger and bigger because obviously those are like larger and larger contracts. What helped you? And I was a type of a consultant before that. And I learned a lot about things before I went into business. So like, worst job I ever had, I was miserable, but also best job for learning. Now, for you, what was in the beginning? What did you do to be able to get these enterprise contracts? Well, …” View more

Ridealong summary

Kandace Swaisland reveals that her early consulting experience was crucial in landing enterprise contracts. By working with over 400 businesses as an auditor, she gained invaluable insights into their struggles, building a network and credibility that set her apart when she transitioned to entrepreneurship. This unique approach transformed her into a trusted partner for larger contracts.

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Founder's Story · The Hidden Compliance Wall That Blocks Small Businesses From Big Contracts | Ep. 328 with Kandace Swaisland Founder of KAKSCORP · Mar 24, 2026

Ridealong summary

AI has commoditized outputs, making differentiation essential for businesses to thrive. Companies must leverage human creativity to guide AI, transforming it from a tool into a catalyst for innovation and growth. This shift is crucial as organizations navigate the complexities of AI implementation and address common misconceptions about its capabilities.

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The AI in Business Podcast · From AI Experiments to Enterprise Value Driving Real Business ROI - with Dan Diasio of EY · Mar 24, 2026

Ridealong summary

Good CEOs know to assess projects without emotional bias. They focus on objective metrics to determine success and ask if they'd invest in a project anew, disregarding past investments. This approach helps avoid the sunk cost fallacy, ensuring resources are allocated wisely for future success.

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Prof G Markets · The Next Inflation Wave Is Already Here · Mar 23, 2026

“… of just getting out there and hustling. Let's talk about how this happened. We're going to wind the clock back to 2017. We were grinding away in our small, tiny office here in San Francisco for Superhuman Mail. And I was, you know, we hadn't even launched, but there was this conference called The Lobby Enterprise put on at that time by August Capital. my co-founder Vivek, Rapleaf Vivek, was like, you should go. I'm like, I don't want to go. We don't have fucking time. I've got to build this. We ought to hit products market fit. I'm not going to take out a week just to go drink tequila next to a …” “… generating everything else. Think about Grammarly, which helps you write more confidently and more accurately. why isn't all of this connected? So there's the opportunity to create a really incredible bundle. And this is another example of just getting out there and hustling. Let's talk about how this happened. We're going to wind the clock back to 2017. We were grinding away in our small, tiny office here in San Francisco for Superhuman Mail. And I was, you know, we hadn't even launched, but there was this conference called The Lobby Enterprise put on at that time by August Capital. my co-founder Vivek, Rapleaf Vivek, was like, you should go. I'm like, I don't want to go. We don't have fucking time. I've got to build this. We ought to hit products market fit. I'm not going to take out a week just to go drink tequila next to a pool in Hawaii. And he was like, trust me, something good will come out of this. I don't know what it is, but something good will happen. And I'm like, fine. This is why I hired you is to make me uncomfortable and to push me to things that I don't want to do. I trust you. I will go have this mandatory vacation. So I turn up and I'm a little bit …” View more

Ridealong summary

A chance encounter at a conference led to the acquisition of Superhuman by Grammarly, worth over $4 billion. The founder of Superhuman, after being convinced to attend the event, showcased his product to a former Google executive who became a fan and later CEO of Grammarly. This illustrates the power of networking and the importance of relationships in business growth and acquisition.

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This Week in Startups · The Drone Company Everyone Thought Was Illegal (Now Worth $4B+) | E2265 · Mar 20, 2026

“… an open conversation with him going and say, listen, okay. Number one, my relationship with you as your brother is more important to me than this business. and this business is starting to sour the relationship because of the discussion we had the other day. And, you know, you want to be a 50% owner in something that you don't contribute 50% to. Correct. And that's just not right. And we need to keep talking about that. So when you think about how to solve this, because I don't think you're going to come back and carry the 50% of the load. I think we're all in agreement on that. So since you're …” “And the $400,000 was your gross revs. That's not your profit. Correct. Okay. Our expenses were about 90 grand last year, so about 310, a little over. So you made 100 and a half each. Yeah. Okay. Okay. Um, well, I think you just got to keep an open conversation with him going and say, listen, okay. Number one, my relationship with you as your brother is more important to me than this business. and this business is starting to sour the relationship because of the discussion we had the other day. And, you know, you want to be a 50% owner in something that you don't contribute 50% to. Correct. And that's just not right. And we need to keep talking about that. So when you think about how to solve this, because I don't think you're going to come back and carry the 50% of the load. I think we're all in agreement on that. So since you're not, since you're not, how are we going to solve this where you're not the 50% owner anymore? Maybe I buy you out. You know, if this was a, and I'm sorry, go ahead. Yeah, I think it's just kind of got an ego about being that 50% over or owner and he's stubborn about it. He's willing to give up money for it, like the percentage of profit being split, …” View more

Ridealong summary

One business owner confronts his brother about their unequal contribution to their joint venture. He emphasizes that their relationship matters more than the business, suggesting a buyout or splitting the company to ensure fairness. This conversation highlights the importance of accountability in partnerships.

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The EntreLeadership Podcast · My Team Member Refuses to Do This Simple Request . . . · Mar 20, 2026

“… loyalty program. We have incredible loyal customers. And the centerpiece of all that is we have the best people and not just in the airline business, in any hospitality business We are folks that are low ego and they love to serve our customers And that what is not changing That is the essential promise of Southwest Airlines When Herb founded this place he looked at the industry in the 70s, in the late 60s and 70s, and went, it's high fare,” “… is essential and what do we stand for, and then what are just things that are attributes of the product. So what has always been true for Southwest is not changing. We have the best domestic network. We have the best hospitality. We have the most rewarding loyalty program. We have incredible loyal customers. And the centerpiece of all that is we have the best people and not just in the airline business, in any hospitality business We are folks that are low ego and they love to serve our customers And that what is not changing That is the essential promise of Southwest Airlines When Herb founded this place he looked at the industry in the 70s, in the late 60s and 70s, and went, it's high fare,” View more

Ridealong summary

Changing the boarding process and snack options at Southwest Airlines sparked strong emotional reactions from loyal customers. CEO Bob Jordan shares how these changes made some feel like the 'soul of the airline' was lost, despite the company's commitment to its core values of hospitality and customer service. Understanding what truly matters to customers is essential for maintaining that emotional connection.

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Bold Names · Southwest’s $1 Billion Pivot: CEO Bob Jordan on Bag Fees And Other Changes · Mar 20, 2026

Ridealong summary

Successful founders know their strengths and when to delegate. They possess innate qualities like grit, determination, and a positive attitude, which are crucial for overcoming challenges. When these traits combine with intelligence, it creates a powerful force for innovation and growth.

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TBPN · Samsung Invests $70B in AI Chips, The Cubanator Joins, Apple: Behind in AI, Ahead in Revenue | Mark Cuban, John Kim, Eugen Alpeza, Ari Herbert-Voss, Alex Konrad, Carl Eschenbach & Pat Grady, Jim Cantrell, Tom Hulme · Mar 19, 2026

“… hear it again. Engineering organizations are funded, tasked, and measured on shipping features that deliver outcomes. If you're selling software and business side has little incentive to fund AppSec because they have already externalized all of that risk to their customers with limitation of liability clauses. Good for them, by the way. Going back to the quote. Yeah. By the way, let's just stop the quote. If you can pull that off, none of this is important. None of this is important. But going back to Greg's quote, if you're developing software for internal customers, there is even less incentive to …” “This is not just a security issue. Greg Notch, CSO of Expel, said, quote, the problem is rooted in economics and incentives. Oh, this came up before. Let's hear it again. Engineering organizations are funded, tasked, and measured on shipping features that deliver outcomes. If you're selling software and business side has little incentive to fund AppSec because they have already externalized all of that risk to their customers with limitation of liability clauses. Good for them, by the way. Going back to the quote. Yeah. By the way, let's just stop the quote. If you can pull that off, none of this is important. None of this is important. But going back to Greg's quote, if you're developing software for internal customers, there is even less incentive to care. The core problem is that there is very little real downside risk, except in extreme black swan type situations. And the probability of that is low enough. Most will accept the risk and probably have a completely rational argument for doing so. This is hard for security people to hear, of course. The extreme example of this is the …” View more

Ridealong summary

The real issue with software security lies in economic incentives, as highlighted by Greg Notch, CSO of Expel. Developers are often rewarded for speed and feature delivery, leaving security concerns sidelined, especially when risks can be externalized to customers. This dynamic creates a friction that security teams must navigate by aligning their goals with business objectives to change the narrative around security's importance.

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Defense in Depth · Who is Responsible for the Conflict Between Security and Developers? · Mar 19, 2026

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Elon Musk's relationship with Jeffrey Epstein reveals a web of influence involving the Dubai Future Foundation and self-driving technology ambitions. In a bizarre twist, Epstein pitched Musk to Emirati officials, leading to a partnership that boosted Tesla's image while Dubai sought cutting-edge innovation. This mutualistic exchange highlights the intricate connections between tech giants and foreign governments.

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Tech Won't Save Us · Elon Musk and Jeffrey Epstein w/ Ed Niedermeyer · Mar 19, 2026

“OK, so with with all that change, there's there's a lot to unpack here. One is as an executive or a business owner, how do I know what to take advantage of? And then as an individual employee or an individual just in the world today I not going to have a job That where the fear is So your book to me could apply to individuals and companies right So, all right. So, John, we've talked about all this great stuff, a little bit of fear. I don't think it's as much fear for me as it is opportunity because I guess I'm an opportunist or an entrepreneur. Yeah, …” “OK, so with with all that change, there's there's a lot to unpack here. One is as an executive or a business owner, how do I know what to take advantage of? And then as an individual employee or an individual just in the world today I not going to have a job That where the fear is So your book to me could apply to individuals and companies right So, all right. So, John, we've talked about all this great stuff, a little bit of fear. I don't think it's as much fear for me as it is opportunity because I guess I'm an opportunist or an entrepreneur. Yeah, see, there's the difference, right? Different words for the same thing, right? I see huge opportunities in front of me, but how in the world do I get started? There's too much going on. So how do I get started? If I were to go through your book in my very first step, what do I do? Yeah, great question. So I think you're right. Signal to noise is a …” View more

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The key to harnessing AI's potential lies in how you communicate with it. Jon Hamm emphasizes that learning to prompt AI effectively can transform your ideas into actionable plans, enhancing productivity and innovation. This skill is crucial for both individuals and companies navigating the rapidly changing tech landscape.

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Embracing Digital Transformation · #335 Increasing your AI Fluency steps to AI Augmentation · Mar 19, 2026

“… It wasn't from this year of writing blogs and trying to out out out work the algorithm. It was actually from three years ago when we put a full on business plan in place for SEO, knowing it was going to be a three year plan. And now that's coming to fruition. So if you're telling me you're thousands of podcasts and, you know, thousand weeks of SEO blog writing, then, yeah, you will be showing up. Absolutely. And that makes sense. It's no hockey stick. Right. I mean, there's no shortcut. You need to do the work every week, every week, every week. That's the one thing I think a lot of, and I have no …” “… don't have an advertising agency. But here's something you're not saying that I think that you've said it indirectly, but it needs to be said because I can tell you I'm showing up on on AI for certain things. And I'll tell you exactly where it's from. It wasn't from this year of writing blogs and trying to out out out work the algorithm. It was actually from three years ago when we put a full on business plan in place for SEO, knowing it was going to be a three year plan. And now that's coming to fruition. So if you're telling me you're thousands of podcasts and, you know, thousand weeks of SEO blog writing, then, yeah, you will be showing up. Absolutely. And that makes sense. It's no hockey stick. Right. I mean, there's no shortcut. You need to do the work every week, every week, every week. That's the one thing I think a lot of, and I have no problem saying it because I speak to too many business owners, not respecting and understanding the power of SEO, number one, but not realizing it's not like paid ads. You don't win right away. You've got to invest, invest, invest, invest time, money, energy, invest time, money, energy in a year, two years. It starts to come to fruition, but it …” View more

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In today's AI-driven world, branding is more crucial than ever, as businesses must connect with customers who increasingly rely on algorithms. Take Gatorade, for instance: despite Powerade's presence, athletes overwhelmingly prefer Gatorade, demonstrating the power of brand loyalty. The challenge lies in measuring the ROI of branding efforts, yet investing in branding is essential to stand out in a landscape dominated by AI.

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The Vault Unlocked · How AI Is Rewiring Your Customers (And Why Most Businesses Aren't Ready) · Mar 18, 2026

“… do, they will have an operational added advantage that you will take time because it's just not a technology that needs to be deployed. It's my business processes or the way I did business fundamentally change. And having that coming in and understanding the hurdles of making that happen, not only from a technology adoption standpoint, but people process is the key aspect that the” “… bring? You've got to change your management mindset, layers, all of that, right? I think has to be rethought. That's what I said, right? When these, it's not about if, or should I think about it is you have to, because if you don't and your competitors do, they will have an operational added advantage that you will take time because it's just not a technology that needs to be deployed. It's my business processes or the way I did business fundamentally change. And having that coming in and understanding the hurdles of making that happen, not only from a technology adoption standpoint, but people process is the key aspect that the” View more

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Companies must adapt to manage AI workers alongside humans, or risk losing their competitive edge. As digital workers become integral to business processes, organizations need to rethink management strategies and operational structures. The shift is not just technological; it fundamentally changes how businesses operate.

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The AI in Business Podcast · How Digital Workers Are Changing Industrial Performance - with Somya Kapoor of IFS Loops · Mar 18, 2026

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A tech company is transforming industries like oil and gas by developing robotics that diagnose asset health in real-time, potentially saving millions. By building technology directly in the field rather than in labs, they aim to enhance operational efficiency and reduce downtime for critical assets like naval ships. This innovative approach challenges traditional methods and could reshape how capital-intensive sectors operate.

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TBPN · AI Side Quests, Zaslav's Payday, SF Housing Market is Back | Shyam Sankar, Gili Raanan, Anna Patterson, Jake Loosararian, carried_no_interest · Mar 17, 2026

“… side. And, you know, I have a question. You said you were early adopter. And one of the things that I get, particularly from, we'll say, service businesses, main street businesses that reach out. I think a lot of owners, operators, executives, maybe second generation family members. So I also seemingly get this a lot. And maybe you see this from the sons and daughters of business owners who maybe tend to go operations versus the hard grind of sales. I think they struggle a lot with how do I stay out on the front edge of what's coming while still doing the day-to-day work that it takes to …” “… floating down a timeline where you still had to click the load more button just to give everyone context. It wasn't even infinity scroll invented back then. And kind of took a similar, took a similar path into marketing and have always been on that side. And, you know, I have a question. You said you were early adopter. And one of the things that I get, particularly from, we'll say, service businesses, main street businesses that reach out. I think a lot of owners, operators, executives, maybe second generation family members. So I also seemingly get this a lot. And maybe you see this from the sons and daughters of business owners who maybe tend to go operations versus the hard grind of sales. I think they struggle a lot with how do I stay out on the front edge of what's coming while still doing the day-to-day work that it takes to actually operate one of these businesses. This is a big mental struggle for people. And they constantly seem to be yo between I way out ahead This isn really producing results I spinning my wheels I wasting time with oh my gosh I behind We don have the right tech Our competitors are getting out ahead of us So as someone who tends to skew early adopter how …” View more

Ridealong summary

To thrive in the fast-paced world of AI tools, successful business owners must delegate effectively. By outsourcing day-to-day tasks, they can focus on testing new technologies and identifying what truly drives results. This approach not only enhances productivity but also keeps them ahead in the competitive landscape.

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Finding Peak w/ Ryan Hanley · How to Build Your Own AI Software (Without Knowing How to Code) · Mar 17, 2026

“… to still get quite far. And I think that applies very much to our situation at the time. We didn't have millions of dollars. We had a consulting business that we had to make pay for all these experiences we wanted to do. And therefore, we just had to be radically more productive. I mean, this, in my case, on the technical side, was the birth of Ruby on Rails. I could not use the same technology as everyone else was using because I had a tenth, a hundredth, a thousandth of the capacity. Therefore, I had to use something else. I had to use something or come up with something that allowed me as an …” “… not buy NVIDIA CPUs due to export restraints. They trained the whole thing on 5 million. I know there's reservations and asterisks behind that. But the fundamental principle was they came up with some novel new techniques of using vastly less compute to still get quite far. And I think that applies very much to our situation at the time. We didn't have millions of dollars. We had a consulting business that we had to make pay for all these experiences we wanted to do. And therefore, we just had to be radically more productive. I mean, this, in my case, on the technical side, was the birth of Ruby on Rails. I could not use the same technology as everyone else was using because I had a tenth, a hundredth, a thousandth of the capacity. Therefore, I had to use something else. I had to use something or come up with something that allowed me as an individual programmer and technical person in the whole operation to build Basecamp by myself on the technical side. I am forever grateful that these were the constraints we were under. if we had raised i don't know 20 million dollars and hired 100 people we would just use the same shit as everyone else and we would never have come up with ruby on …” View more

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David Heinemeier Hansson reveals that many investors, including himself, initially saw Facebook's traffic as 'trash' without a solid monetization strategy. He explains how the shift to surveillance capitalism transformed this perceived trash into gold by targeting ads based on user data. This insight highlights the unexpected ways businesses can turn failures into successes.

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My First Million · DHH: $100M+ Advice That'll Piss Off Every Business Guru · Mar 17, 2026

“… they had built payroll engines in South Africa and eventually expanded across all of the different countries in Africa because South Africa is too small. And they had not realized that they had built the first global payroll engine by just going into the other countries in Africa. and bringing them in we brought in like 15 or 20 plus years of experience in building hardcore very boring but very hardcore payroll knowledge and payroll engine building which is basically like how do you calculate your salary gross to net all the calculations in every country like a lot of companies are trying to do …” “… We're really very much acquiring for expertise and years of experience. For example, we acquired a company called Payspace. Payspace was a company started in South Africa by four brothers or three brothers and one brother from another mother. And they had built payroll engines in South Africa and eventually expanded across all of the different countries in Africa because South Africa is too small. And they had not realized that they had built the first global payroll engine by just going into the other countries in Africa. and bringing them in we brought in like 15 or 20 plus years of experience in building hardcore very boring but very hardcore payroll knowledge and payroll engine building which is basically like how do you calculate your salary gross to net all the calculations in every country like a lot of companies are trying to do this right now i think i'm decently smart i think my team are very smart i would not be able to do what those guys did uh so bringing that knowledge in house and like rebuilding with them is like it's just such an acceleration for the business because we're in such an m&a acquisitive oh we're in m&a land right now yes i mean it's and you have …” View more

Ridealong summary

Deel's CEO Alex Bouaziz reveals that only 10% of their revenue comes from acquisitions, focusing instead on gaining expertise and experience. By integrating newly acquired companies quickly and efficiently, Deel turns potential disruptions into growth opportunities, achieving impressive results in just 12 months.

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Sourcery · Deel Hits $1.4B+ in ARR | CEO Alex Bouaziz Shares Growth Playbook · Mar 17, 2026

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