In this episode of "Acquired," hosts Ben Gilbert and David Rosenthal, along with guest Courtland Allen of Indie Hackers, discuss the evolution of entrepreneurship in the digital age. They explore how the internet's reach has enabled niche businesses to thrive, and how platforms like Indie Hackers empower underdog entrepreneurs by providing inspiration, community support, and visibility. Courtland shares his journey from starting multiple companies, including the challenges and lessons learned, to Indie Hackers' acquisition by Stripe—a move that has significantly expanded the platform's reach and impact. The conversation also touches on the importance of aligning incentives in acquisitions, the value of trust, and the potential for tech companies to invest in media platforms to connect with audiences.
"I've got new m one MacBook Air. This is the first episode we're doing on it. Nice." "Nice. Silent recording in the background."
The quotes highlight the excitement about the new recording equipment, emphasizing the silent operation due to the MacBook Air's active cooling system, which is a feature of the MacBook Pro.
"Welcome to this special episode of Acquired, the podcast about great technology companies and the stories and playbooks behind them. I'm Ben Gilbert, and I'm the co-founder of Pioneer Square Labs, a startup studio and venture capital firm in Seattle." "And I'm David Rosenthal, and I am an angel investor and advisor to startups based in San Francisco."
The quotes introduce the hosts and the focus of the Acquired podcast, setting the stage for the discussion on technology companies and entrepreneurship.
"But today's episode is quite a bit different. In our conversation with Courtland Allen of Indie Hackers, which is the largest community of startup founders, we dive into the stories of the underdogs."
The quote sets the episode's theme of exploring the journeys of underdog entrepreneurs and the role of the internet in facilitating their ventures.
"No kidding. And a lot of people cannot wait for it to IPO soon enough." "That's going to be I got to imagine our biggest episode of next season. Hopefully next season."
The quotes convey the hosts' anticipation for Stripe's IPO, suggesting it will be a significant event for the podcast to cover.
"The community of Acquired Limited Partners is now an army in the thousands. For those of you who aren't already a part of the gang, becoming an LP gets you twice as many episodes, access to live events with us and other LPs."
The quote promotes the Acquired Limited Partners community, emphasizing the benefits of membership and the influence members have on the podcast.
"Our next sponsor for this episode is one of our favorite companies and longtime acquired partner Pilot for startups and growth companies of all kinds."
The quote introduces Pilot as a sponsor, highlighting their focus on providing accounting services to startups and their growth into a significant company.
"Okay, now on to our crossover episode with Indie Hackers, Courtland Allen. Welcome to acquired." "Yeah, I'm excited to do this. People have been asking for a while for me to do an episode on myself."
The quotes introduce Courtland Allen and his platform Indie Hackers, setting the stage for a discussion about his journey and the indie philosophy in entrepreneurship.
"And so people are creating these very tiny niche businesses that could never have existed 20 or 30 years ago, and in some cases not even five or ten years ago."
The quote from Courtland Allen highlights the transformative effect of the internet on entrepreneurship, allowing for the creation of niche businesses with global reach.
"With the Internet, you can just do one thing in one niche, but you have a nationally, if not globally addressable, market."
The quote emphasizes the paradigm shift in entrepreneurship, where the internet allows niche businesses to reach a global market, contrasting with the geographical limitations of traditional small businesses.
"So I was just talking to Jason Calacanis about this on his podcast, where he was talking about, kind of know, can anybody start a company? Does everybody have an equal chance to do this?"
The quote introduces Courtland Allen's perspective on the varying starting points individuals have when embarking on entrepreneurship, acknowledging the mix of advantages and challenges he faced.
"So the very first one was this company called Fmail, which stood for, get this, Gmail for Facebook."
The quote recounts one of Courtland Allen's early entrepreneurial ventures, showcasing his innovative approach to combining existing platforms to create new products.
"We did winter 2011 for YC. So this was like in the fall of 2010, like November, December."
The quote places Courtland Allen's YC experience in a timeline, providing context for the development of his project and the broader startup ecosystem at the time.
"And we presented and investors, just like, they weren't interested. They're like, yeah, you've had okay, growth, but where is this really going?"
The quote highlights the lack of investor enthusiasm due to the startup's moderate growth and unclear future direction.
"And he was just like, yeah, we're not raising any money. We packed our bags, we moved to Florida. We're making forms, but we're making forms sexy."
This quote illustrates Kevin Hale's unconventional approach to building a successful business without the need for venture capital.
"They need people to go for the gold. What ends up happening is just a lot of YC companies died."
This quote explains the high-risk, high-reward nature of YC's investment strategy, where many startups fail while aiming for massive success.
"Being an indie hacker is really about the idea that you can achieve your own sort of freedom, whatever that means to you."
The quote captures the essence of the indie hacker ethos, which is centered around personal freedom and self-determination through entrepreneurship.
"So we threw up kind of a stripe subscription in maybe like a day or two, just like over a weekend. And the next weekend I think we made like $3,000 in payments."
This quote demonstrates the rapid impact of implementing a payment system on the startup's revenue, leading to a critical moment in the business's direction.
"Really all you need to do is just to make sure that you don't quit before you get to that number. That's really the entire name of the game, just don't quit before you get to the number where you succeed."
The quote underscores the importance of perseverance in entrepreneurship, suggesting that success is a matter of persistence rather than immediate success.
"I want to build kind of an indie hacker business so I can sort of pay my rent, pay my bills, and then figure out what I want to do next."
This quote reflects the founder's intention to create a self-sustaining business that could also serve as a stepping stone to future endeavors.
"I decided I wanted to make the site like blue. So it's like this very dark blue color that's probably not very accessible and kind of hard to read. But every other site in existence was just like white with black text. Everybody was writing on medium. It all looked the same."
The quote explains Courtland's intention to differentiate Indie Hackers visually from other content platforms, emphasizing the importance of unique branding in digital spaces.
"I wasn't thinking about, honestly, any of that indie even. I wasn't even aware that there were indie developers. I was just like, okay, well, I want the idea of an independent programmer..."
This quote highlights Courtland's focus on the concept of independence in programming and his lack of awareness of the existing indie developer community, reinforcing the originality of the Indie Hackers concept.
"There are no hard and fast rules. Like never build on a platform, right? Like if you build on a platform, maybe it can give you additional distribution, but then you get the risk that they might shut you down or change things..."
The quote reflects Courtland's nuanced understanding of platform risk, suggesting that while platforms can offer benefits, they also come with significant risks that must be carefully considered.
"Budy, Greg Eisenberg, has this whole idea of unbundling Craigslist, unbundling Reddit, unbundling hacker news. It's a huge community. There's all sorts of sub discussions happening in there that happen regularly."
Courtland's quote reveals the inspiration behind Indie Hackers, which was to create a focused community for discussions that were otherwise scattered within larger platforms like Hacker News.
"You can almost imagine the web is like a collection of feeds or destinations, and some of them are places where people go habitually."
This quote explains the rationale behind leveraging email as a channel, recognizing it as a habitual destination that could be used to maintain engagement with Indie Hackers' content.
"So I created kind of like a dream list of companies. Like, okay, which companies actually have a lot of money? That would be good sponsors."
The quote illustrates Courtland's strategic shift from targeting smaller startups to larger companies with bigger budgets for advertising, highlighting the importance of aligning with sponsors that have the financial capacity to support the platform.
"I get this email out of the blue... 'Acquire Indie Hackers?' from, like, patrick at stripe. And I was just like, holy shit, there's like, there's no way this email is real."
Courtland's reaction to the acquisition offer from Stripe conveys the surprise and significance of the opportunity, indicating the potential for Indie Hackers to align with a larger entity that shared similar goals.
"So I just emailed as many people as I knew who either worked at Stripe, had dealings with Stripe, or had dealings with Patrick in the past. I'm like, hey, what kind of person am I dealing with? And I got a lot of really positive stories."
This quote highlights the process of due diligence Courtland undertook to establish the trustworthiness of Stripe and Patrick Collison before entering into any agreement.
"And part of that was also doing research, like, how much do engineers at Stripe get paid? By that point, I was pretty good at getting people to reveal numbers to me from working on Indie Hackers."
Courtland used his experience and research to inform his negotiation strategy, ensuring he was well-prepared to discuss compensation and benefits.
"If it's Stripe, for love of God, take the equity, take the stock. If it's a Groupon, then I don't know, maybe you want the cash."
This quote emphasizes the strategic decision-making involved in choosing between equity and cash during an acquisition, depending on the company's prospects.
"There's like a very small little logo that says Stripe at the very bottom of the website that you kind of have to search to find, which is freeing in a way."
This quote illustrates how Indie Hackers retained its unique branding and identity even after being acquired by Stripe, benefiting from association while remaining largely independent.
"And one of the things we like to measure is kind of like a rough estimate of how many people have started companies as a result of Indie Hackers."
This quote highlights Courtland's focus on the tangible impact of Indie Hackers on entrepreneurship, using metrics to assess its success in inspiring new business ventures.
"Oh, a plus. I think it's, I'm slightly biased here. Like, Stripe is a company, as you may know, that has lots and lots of money. And the India Acres acquisition did not cost billions of dollars."
Courtland rates the acquisition highly, recognizing its value and impact relative to the investment made by Stripe.