Entrepreneurs at work
Founders sharing their journeys — starting companies, raising money, finding product-market fit, and the reality of building something from nothing.
100 clips
·
49 podcasts
Listen to the Playlist
Curated by Ridealong from the best podcast clips.
Top Podcast Clips
“Mm-hmm. Yeah. Or wasn't it dye to match the band Perry's blonde? Oh, no. I can show you evidence. I good I believe you No I met Johnny in October of 2020 in Dallas because Irene and I were working on some music down there and I just immediately fell in love with him And I can tell you he was that blonde. Very platinum. But he used to, he was not wearing leather as much then. You were wearing Carhartt overalls without t-shirts. Where are you from? Grew up in Dallas, Texas. Yeah. But mostly like …”
Ridealong summary
In this hilarious segment, the host recounts an unexpected culinary adventure while traveling in Europe, where he insists on stopping for a hot dog despite just having lunch. The twist? It's not just any hot dog; it's a 'worst' that is bigger than the bun and the best he's ever had, leading to a comedic reflection on European gas stations being like 'Buc-ee's everywhere.'
“And so NSF, it's taxpayer funding. So the government at least is not supposed to be funding businesses directly, although sometimes they do. But there was formal legal restrictions on funding things with commercial applications. And so what there was is there was something called the AUT, the Acceptable Use Policy. And the Acceptable Use Policy said that basically the internet, NSFnet turned internet was for academic and research use, and commercial activities were strictly prohibited, like …”
Ridealong summary
In September 1993, AOL connected regular users to the internet, marking the start of what Marc Andreessen calls 'Eternal September.' Before this, the internet was a utopian space for the world's brightest minds, free from commercial influence. This pivotal moment transformed the internet from an exclusive academic network into a mainstream platform for ordinary people, fundamentally altering its nature.
“So then I decided to take some time off and explore and have some fun. Yeah. And what time was this? What year was this? So I started working in 2007 and I left by 2009, which was actually in retrospect, I was really brave because it was in the midst of economic downturn. My thought process at the time was I was only 22 or three. And I figured even if I take a year off, I can still catch up, which I did. And what happened from there? How did you eventually get to WhatsApp? That was years later, …”
Ridealong summary
In 2012, I took a leap of faith and joined WhatsApp, a startup that was just beginning to gain traction outside of Europe and India. After taking a break from my career to explore my interests and gain life experience, I was ready for a role that offered both autonomy and mentorship. My journey to WhatsApp started with a chance encounter on LinkedIn, leading to a unique interview experience focused on system design rather than traditional coding tests.
“that. But when we sat down at the first meeting, the person we were sitting across was like, what are you going to do for the company? And I was like, oh, no, I'm pregnant. I'm just here to afford him. And she was like, oh, no, no, no, no, no, no. You're a part of this. And now I run the company and the scouts on permanent furlough. He's on permanent furlough. I admire the fact that you can work with your husband because like I sit next to my husband in our shared office. We don't work …”
Ridealong summary
Jacqueline Tatelman, Co-Founder of STATE Bags, shares how her simple idea transformed into an 8-figure business. Initially unsure of her role, she navigated challenges, including product failures, to create a brand that resonates with consumers through its give-back mission. The journey highlights the importance of separating personal and professional relationships while adapting to market needs.
“and got the money he needed to start the company. And then fast forward to 2013, which the excerpt in the Wall Street Journal of your book tells the story of a birthday party for Elon Musk, replete with all kinds of costumes and strange things and fake battlements. But this is perhaps, apart from the founding, the most crucial moment in DeepMind's genesis as a company, right? Yeah, that's right. So, you know, by this point, Demis had raised three rounds of venture capital, including from Elon …”
Ridealong summary
In a pivotal moment at Elon Musk's birthday party, Demis Hassabis, co-founder of DeepMind, was approached by Google’s Larry Page with an enticing offer: join Google and focus on science rather than fundraising. This unexpected conversation led to DeepMind's acquisition by Google, allowing Hassabis to pursue his passion for artificial intelligence with the resources he needed. The decision marked a critical turning point in the AI landscape.
“I called Sam into the office and Steve, I'm like, no, Sam. He was there. Steve was at studio working there. And I said, hey, Sammy, come here. Want to see something cool? He's like, yeah, check this out. And I pulled up my computer screen. It was not many thousands in there. And we had, you know, a huge nut to cover. We're halfway through the month. And he just looks at me and I'm just like, oh, that's our bank account, huh? I'm like, yeah, pretty much all the money we have. I'll share. We had …”
Ridealong summary
Facing a $300,000 payment deadline with only $10,000 in the bank, three entrepreneurs turned their dire situation into a success story. Instead of playing the blame game, they focused on their shared values and relentless execution, ultimately selling $700,000 worth of saunas in just two weeks. The key takeaway? Choose partners who align with your values and are willing to take risks together.
“So how did you raise money being in England at the time for Reportive? Well, you were a huge help for this. So like Jason said, we went viral very, very quickly, and then he emailed kind of out of the blue. And this was, I should share, it might be helpful for folks to know, this was like attempt number five or six for me as a startup. People often say, oh, great, you're two for two. I'm like, yeah, but remember the five startups before those two that completely failed and went nowhere. And so …”
Ridealong summary
Raul Vora's journey shifted dramatically when he went viral with Reportive, attracting major investors like Sequoia. After several failed startups, he finally found success in fundraising by connecting with influential angels at intimate events in California. This experience highlights the evolution of startup funding from small checks to larger investments in today's market.
“Building this media company, so to speak, has been the hardest thing I've ever fucking done in my life. If you knew what you were going to have to go through day one when you started this to get to today, would you have done it? No. I would have stayed in corporate America, made 300 grand a year and just been completely happy taking vacations whenever I wanted to because we had money to do it and lived like a robot. I'm going to tell it to everybody right now listening. Yesterday was a very …”
Ridealong summary
Building a media company can be incredibly challenging, as revealed by the speaker's candid reflection on their journey. They share a moment of vulnerability when their child senses their distress, highlighting how the pressures of entrepreneurship affect family life. This emotional insight underscores the unseen difficulties that come with pursuing success in the media industry.
“I tweet about them. I get information back in the process. I see your work. I see your work. I see a bunch of folks and try and incorporate that back in the box. My job is to try and connect all these things together and make it useful. And you're the number one spokesperson, right? So you do have to be out there. Yeah, but I kind of would be doing it whether or not... It's like I don't really think of it as a job requirement as much as like I just like social media. You're so good at it. Yeah. …”
Ridealong summary
The idea for Box was sparked during an internship at Paramount, where the challenge of sharing data mirrored the struggles of traditional enterprise software. This realization led to the creation of a platform that simplifies collaboration, blending the worlds of film and digital innovation. By connecting these dots, the founder transformed a passion for cinema into a groundbreaking business solution.
“Well, what Compare and Swap allows you to do is basically just you download the file, you make the modifications, and then you write it only if it hasn't changed while you did the modification. And if not, you retry, right? You just have this retry loops. Now, you can imagine if you have 100 nodes doing that, it's going to be really slow, but it will converge over time. That primitive was not available in S3. It wasn't available in S3 until late 2024, but it was available in GCP. The real story …”
Ridealong summary
Against all odds, we built our database on GCP, relying on a Compare and Swap feature that S3 lacked until late 2024. Our conviction led us to invest heavily in reducing latency, even laying dark fiber to connect AWS regions, despite our clients' skepticism. This gamble paid off as we navigated the challenges of cloud architecture, proving that innovation often comes from unexpected places.
“And we had great conversations about health care and what needed in health care And she just really lifted me Yeah that cool Yeah you never meet a successful person who didn have someone like her you know in their life or your CEO before you. So what's daily life like as a CEO of Amtelco? I think a lot of people, I think one of the reasons we have such a broad listenership and so many people that listen and put us in the top 10 globally is people want to know, you know, what's it like to be …”
Ridealong summary
As a CEO, my daily life revolves around supporting my team, much like bringing water to troops. I attend various meetings, including those with customers testing our software, to gather feedback and ensure our leaders have the resources they need. This approach not only fosters a strong company culture but also drives our overall success.
“Thanks, Jason. Pleasure to be here. Yeah. And so you started in Sydney, you and your brother was seven, eight years ago, and you got in early on Bitcoin and all these Bitcoin miners wanted to have data centers, huh? Yeah, that's directionally right. So the thesis we saw was this explosion of the digital world, the growth in the online. And at some point, the real world was going to struggle. So we set about to build out large scale data centers. Yes, the first use case was Bitcoin mining. But …”
Ridealong summary
Iren, led by Daniel Roberts, transitioned from Bitcoin mining to AI computing in just a few years. Initially, they built massive data centers to support Bitcoin miners, but as demand for AI compute surged, they pivoted their focus, showcasing their foresight in the digital landscape. Now, with a flagship site in Texas generating 750 megawatts, they are at the forefront of high-performance computing.
“See, my concern isn't for guys like us. And I love when you said in one of your interviews. By the way, I saw a clip yesterday. It could have been you. It says, sometimes all women want is a man that's got a vision, selling a vision. One day, we're going to do this. One day, we're going to be this. they need to have a man be in a pursuit of a vision and a dream, whatever that may be. But going back to it in regards to this with, you know, uh, you know, the idea of faith and all that stuff, I'm …”
Ridealong summary
After 25 years as an atheist, I found purpose through two transformative books: C.S. Lewis's 'Mere Christianity' and 'Case for Christ' by a mathematician. This shift in perspective fueled my entrepreneurial spirit, starting from selling hats in school to embracing a vision for success. It's a story of how belief can redefine your path to wealth and fulfillment.
“I want to have a little extra money. I want to blah, blah, blah. And that's all great shit. That's like your foundation. That's the shit you have to have. Okay, but that's not the win, bro, because now you have all this knowledge. Now you have all these skills and now you have these relationships. Now you know how to execute And if you stop now you going to feel like a failure your whole life regardless because you going to always ask yourself what could I have been had I actually committed So …”
Ridealong summary
If you stop pushing yourself, you'll feel like a failure for the rest of your life. To avoid stagnation, entrepreneurs must continuously expand their purpose and goals, as the world is always moving forward. The only way to protect your current success is to stay on offense and keep striving for more.
“Right. You don't have to be on a rocket ship every time you start a business. That's not the point, at least not to me. Right. So you just have to think about what you want your company to be and what potential does it have. With TaskRabbit, I always saw a vision of the world where the future of work was changing. The gig economy at the time was nascent. It was not a thing. We really helped create the gig economy along with other companies. And so for me, it was like, this is a venture-backed …”
Ridealong summary
Leah Solivan reveals how TaskRabbit helped create the gig economy during the Great Recession of 2008, capitalizing on a wave of layoffs among high earners. She emphasizes that they didn't invent the concept, but rather recognized a crucial shift in the future of work. This foresight allowed them to build a scalable venture that resonated with a changing workforce, setting the stage for the freelance trends we see today.
“The co-founder of HubSpot came on this podcast and he talked about in his first company, he was making everything up. And his second company, he said, oh, now I know how I'm going to do everything differently. And it totally failed. And he goes, just because I was ignorant doesn't mean I was wrong. And there something to that idea of like you can be both ignorant and correct I go so far as to say that ignorance is a benefit for a huge class of problems That you are cursed when you've been …”
Ridealong summary
David Heinemeier Hansson reveals that sometimes being ignorant can actually be beneficial in business. He shares how the co-founder of HubSpot learned from failure after overthinking his second company, contrasting it with the fresh perspective of starting anew. This insight suggests that breaking free from established paradigms can spark innovation and success.
“So wait, wait, 100% you're going to put in your own company? Not 100% because I think for the next venture, I will most likely raise money just because now this is kind of like my nest egg. I never need to worry about it. I'm definitely willing to like take risks. But how much? What percent? Like in your head, you're thinking, let's say hypothetically, you have $10 million. What percent do you want to put in your new company? Yeah, well, I mean, maybe this goes to the EV question a little bit, …”
Ridealong summary
At just 20 years old, this ambitious entrepreneur is at a pivotal moment, contemplating whether to invest a significant portion of his wealth into his next venture. Drawing inspiration from Elon Musk's risky bets, he recognizes the importance of understanding global trends to build a tech giant. This conversation captures the essence of youthful ambition and the potential for future success.
“Just to underline that a bit, Anthropic says its run rate revenue has hit 14 billion dollars, growing over 10x annually in each of the past three years. And Claude Code's run rate revenue has grown to more than two and a half billion dollars. We are, folks, seeing revenue in some of these places. Go hockey stick. Here's another data point to that end. Also from CNBC, Cohere hit roughly 240 million dollars in annual recurring revenue last year, surpassing its 200 million dollar target, according …”
Ridealong summary
Cohere's annual recurring revenue skyrocketed to $240 million, surpassing its $200 million target, with a quarterly growth rate exceeding 50%. Founded in 2019, this Toronto-based startup is backed by major investors and is poised for a public market debut, thanks to its capital-efficient model that allows customers to run AI models on their own infrastructure. This strategic approach positions Cohere for sustainable growth in a rapidly evolving AI landscape.
“market news here. So Polymarket, which is the leading prediction market platform, acquires Brahma if I saying that right B to scale blockchain trading infrastructure So we know these platforms are very disruptive And in fact you know the crypto industry is facing a lot of battles from incumbents You got the banks”
Ridealong summary
Polymarket, the leading prediction market platform, has acquired Brahma to enhance its blockchain trading infrastructure. This strategic acquisition comes as the crypto industry faces intense competition from traditional banks and other incumbents. By scaling up their technology, Polymarket aims to solidify its position in the rapidly evolving market landscape.
“But he made it back. He did make it back and more. He was worth like $8 or $9 billion and got down to his last $1 billion, basically, because of the stock drop in Amazon. But he not only kept Amazon alive, which I think everyone knows that, you know, Amazon went up during the dot-com bubble and then crashed and then built back up. But he also kept Blue Origin alive during that time because he founded Blue Origin in 2000. Wow. Before the crash. I didn't know that. Yeah, before the crash. So he …”
Ridealong summary
Jeff Bezos faced a near-collapse of his fortune during the dot-com crash, dropping from $9 billion to just $1 billion. Despite this, he kept both Amazon and his space venture, Blue Origin, alive, showcasing his unique operational skills. This resilience has allowed Blue Origin to finally unlock new capabilities, proving Bezos's strategic vision in the face of adversity.
Top Podcasts in This Playlist
TBPN
5 clips
Sourcery
5 clips
The Pragmatic Engineer
2 clips
This Week in Startups
2 clips
Latent Space: The AI Engineer Podcast
2 clips
All-In with Chamath, Jason, Sacks & Friedberg
2 clips
My First Million
2 clips
Thinking Crypto News & Interviews
2 clips
