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A few weeks back in this very email, I put out a request for a new content format we wanted to experiment with that we called “Startup Confessionals”.
From my note:
If you, or founders you know, are willing to share a startup confessional, we’d love to help. We can make these totally anonymized or public, whatever you're comfortable with. We'll be recording these remotely and aren't looking for hours long conversations — we're planning on editing them into quick lessons and anecdotes.
For example, here are “confessional” conversations I’ve had with people one-on-one just in the last few weeks:
— Over/under raising
— Surprising/shocking fundraising stories
— Horror stories of investors/board members behaving badly
— Hiring to please investors
— Acquisitions blocked or held hostage by investors/board membersThankfully, a few heeded the call. I think this week’s video captures the essence of what we were going for and the experiences we were hoping to mine.
This week, we have stories and lessons from some legendary founders —
Ben Kauffman
Founder of Quirky and Camp as well as CMO at Buzzfeed. Ben has an incredible knack for building brands and storytelling that has attracted some of the largest brand partnerships and most legendary investors.Harper Reed
Came into the national spotlight as the Chieff Technology Officer for Barack Obama’s re-election campaign. Shortly after, with encouragement and funding from then-Google CEO Eric Schmidt, he founder Modest which was later acquired by PayPal. Most recently, he wound down a venture backed startup Galactic. He’s currently exploring new ideas with his longtime collaborators.Finbarr Taylor
Got his start in tech in various staff roles at companies like Groupon, Pebble, and Y Combinator. As a co-founder of Shogun, he and his partners bootstrapped to over $1M in ARR before raising their first round of funding. That first round let to another and then another. Shogun continues to be a thriving business that Finbarr remains on the board of and actively advises in addition to angel investing. His takeaways from bootstrapping to rocketship growth to near unicorn status are lessons not to be missed or dismissed.This is our first attempt at this format and we’re so grateful to Ben, Harper, and Finbarr (as well as the others we have in the can) for being willing to wade into such uncertain waters with us.
We’re really happy with how this turned out and welcome your feedback on how we can improve it over time.
We’d also welcome more stories from you or your networks. If you know someone who’d be fun/interesting/insightful on the topic of unpacking their founder, or early employee experiences and lessons, please send them our way!
As always, we hope you enjoy watching this one as much as we all enjoyed making it.
Bryce
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As someone who entered the venture industry in the wake of the Dot-com crash, I have a deep appreciation for new managers, their entry point into the industry, and how that shapes their world view. For me, it was pure carnage for the first few years of “investing”. I put that in quotes because it was mostly triaging the portfolio and trying to assess which companies were worth saving and which were destined for the Dot-com dust bin.
Shortly after stepping out on my own to start OATV, another bubble burst with the Global Financial Crisis™. My trips to NYC for board meetings were often capped off with midnight strolls through Zuccatti Park to witness the occupation of Occupy Wall Street. The markets were in free fall, checkbooks closed, and founders, once again, were at the mercy of the market.
But easy times never make for strong people and that’s why I was excited to sit down with Turner Novak when we both found ourselves in Columbia, MO for the Main Street Summit a few weeks back. His is a “chronically online” story of discovery and persistence into the world of startups and VCs. Through the use of memes, social networks, and data, Turner was able to build an audience and a “fantasy portfolio” to land himself an internship and, eventually, a fund of his own.
Turner came into his own as an investor in the frothy times of the not-too-distant past. With wide eyes and fresh funds to deploy at his newly formed firm, Banana Capital, he set to work deploying near the peak of the ZIRP bubble. I thought it would be fun to unpack the experience of someone who built their brand online, from the midwest, and began deploying into a market that’s rules and dynamics quickly changed on them.
With that as the goal, this one did not disappoint. A few takeaways:
- Turner’s exposure to entrepreneurship began early with his mother running a small wedding gown business. Turner developed an interest in technology and the internet during his teenage years, teaching himself programming.
- Turner’s path into venture capital began in college, where he joined the investment club and got hooked on investing. After working in commercial lending and for a nonprofit endowment, he started building a “fantasy VC portfolio” on Twitter, which helped him break into the industry. His visibility on social media eventually led to his first job in venture capital.
- Turner’s largest learning from the last few years in venture is the importance of entry points — getting in at the right valuation can make or break an investment. While many aspects of startups are unpredictable, controlling the price you pay is crucial for long-term success.
This was a really fun one and I think Turner has a bright future ahead of him as an investor and fund builder. The easy times may be over, but I can see his strength already showing through as he navigates this new reality.
I hope you enjoy listening as much as we enjoyed recording it.
PS - Today is my birthday and all I want is for you to A) subscribe to the INDIE YouTube channel (just hit that subscribe button) and B) send the next category defining company our way. Is that too much to ask?!?
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A few weeks back, I was the morning speaker at an event hosted by David Senra of FoundersPodcast (one of my favorite podcasts and people). The afternoon speaker was someone I’d never heard of before, Shegun Otulana. The story he told resonated deeply — a Nigerian immigrant who came to study at the University of Alabama. He had the drive to be an entrepreneur and had a few early attempts that ended in a failed partnership and a pile of debt.
Feeling like he was made for more than pushing pixels at a 9-to-5, and at the urging of his wife, Shegun set out to find a problem he could solve and eventually build a business around. A chance encounter led to meeting the head of a mental health clinic in Birmingham, AL. They needed a new system to run their practice but none seemed to fit their unique needs. After failing to find them something he could help them buy, Shegun built them a simple app. That simple app led to feature requests, which led to his first paying customer and then the word of mouth began to spread.
Within 5 years, after only having raised $250,000 from local angel investors and with no experience in the industry, that side project had become a thriving business doing north of $50M in ARR and was valued at hundreds of millions of dollars. Along the way, he has able to bring in PE investors and de-risk his personal finances with several rounds of secondary. He eventually sold the business to KKR in 2021 for $1.25B, making it the largest tech exit in Alabama.
Some takeaways from this one:
— Shegun built a successful healthcare software company through disciplined, customer-obsessed growth. Their approach centered on deeply understanding customer problems at counseling centers and building the initial product based on direct feedback. They found differentiation through an innovative pricing model aligned with customer needs and an SEO forward sales motion.
— Starting with just $250,000 in initial funding, Shegun grew the business to over $50M in revenue within 5 years, eventually selling to KKR for $1.25 billion. Shegun emphasized fundamental business principles rather than chasing fundraising hype. The company maintained strong financials with 30% profit margins and 90% gross margins, growing organically without requiring additional capital on the balance sheet.
— Shegun’s leadership philosophy focused on creating a culture of transparency where team members could be vulnerable while maintaining high standards. He built a distributed team to access talent cost-effectively and gave team members significant autonomy within clear guidelines.At the conclusion of his talk at Senra's event, we both met in the hallway and gave each other a big hug. It was like finding someone who was a part of your tribe — speaking your same language and sharing your same values.
When we realized we’d both be at the Main Street Summit the following week, we decided then and there to get his story recorded. The MSS organizers were kind enough to turn over their main stage theatre for us to record in after hours and I think the resulting conversation and visuals make this one you can't skip.
I hope you enjoy listening as much as we enjoyed recording it.
As always, if you or someone you know is working on something that could be a fit for indie, don't hesitate to reach out.
Bryce
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When I reached out to Charles Broskoski, co-founder of Are.na, it was largely because I kept hearing mention of the service he'd built increasingly entering the zeitgeist among young, creative technologists.
What I thought would be a conversation about the tension between creativity in technology ended up being a much more nuanced conversation.
Some takeaways —
Arena has been operating for 13 years and has taken a slow, steady approach to growth. Arena initially struggled with fundraising but found success through a crowdfunding campaign and charging for their product. They prioritized profitability and user feedback over rapid growth or chasing trends. That trade-off leaves potential money on the table, but allows the community to flourish into its own unique place.
More Artists should start businesses — entrepreneurship provides an endless stream of problems that need solving through creativity and ingenuity. Focus on genuine passion and interest rather than chasing what seems “cool” or trendy with investors. Charging users early to validate the product and gain meaningful feedback.
Charles & Are.na have long been critics of traditional social media, for better and for worse. They’re critical of algorithmic recommendations and AI implementations that remove human discovery and idiosyncrasy from products. He believes in maintaining a human relationship with topics and interests, rather than optimizing for efficiency.
Charles and I had crossed paths several times in years past as he and the team had been working to bring Are.na to life. With each interaction, I was impressed with his vision, earnestness, and commitment to serving a community he cares deeply about.
The parts of this conversation I haven't been able to shake are the need for role models for creative technologists to follow and the trap that many fall into, chasing what's cool instead of creating something that's uniquely theirs to build.
There's something in here for everyone.
I hope you enjoy listening as much as we enjoyed recording this one.
As always, if you or someone you know is working on something that could be a fit for indie, don't hesitate to reach out.
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After wrapping this week’s conversation with published author and ReadySet’s CEO, Y-vonne Hutchinson, I stepped out of the studio, opened my phone, and X was ablaze.
In the year of our Lord 2024, a startup had decided that an anti-woke marketing campaign was the best possible way for them to generate attention for their payroll software company. The culmination of this campaign was one of their sales affiliates posting a racist rant. The fallout from this was all over my timeline. Even the most anti-woke of the tech set found themselves embarrassed and deeply uncomfortable with the direction and velocity the pendulum was swinging.
Tech has a tortured relationship with DEI, race, and gender. The world is becoming increasingly diverse, yet the number of employees and funded startup founders from diverse backgrounds has remain unchanged, if not shrunk. Because the Me Too, George Floyd, and Black Lives Matter movements have left a bad taste in the mouths of many tech leaders, I fear we’re at risk of throwing the baby out with the bath water.
At the heart of this uncomfortable conversation is something deeply important to company cultures specifically, and the future of tech broadly, so I invited my friend Y-vonne to talk about it.
Y-vonne and her company ReadySet were part of the Indie v4 batch of companies. I have a deep respect for her, her work, and the company she’s building. A few takeaways from this conversation:
Historical Context of DEI Efforts
Progress in diversity, equity and inclusion (DEI) often follows a pattern of advancement followed by backlash and retrenchment. This has happened repeatedly throughout U.S. history. The recent pushback against DEI initiatives can be seen as part of this historical pattern, rather than an isolated event. DEI efforts sometimes focused too much on individual change rather than systemic issues, leading to fatigue.DEI in the Tech Industry
The broad, nebulous nature of “DEI” as a concept allowed it to become a target for criticism. Some DEI initiatives were performative rather than substantive, causing disillusionment. The tech industry initially embraced DEI efforts, but economic pressures and changing market conditions led many companies to cut DEI programs and staff. Some tech leaders have used DEI as a “boogeyman” to justify cuts, even though the underlying issues of bias and lack of diversity remain unaddressed.DEI as a Business Imperative
Y-Vonne argues that DEI should be seen as a tool to solve real business problems like attrition, market share, and product-market fit. Companies that ignore diversity issues risk building products that don’t serve increasingly diverse markets and user bases. Companies should aim for “healthy culture” that enables collaboration and innovation, rather than trying to mandate diversity, but the healthiest cultures are diverse.Moving Forward
Work environments should avoid causing trauma, but shouldn’t be expected to heal past traumas - that’s not their purpose. While companies shouldn’t be responsible for “healing” employees, leaders can adopt a more trauma-informed approach to avoid causing additional harm. Broader social and political change is needed to address systemic issues, beyond what individual companies can accomplish.The world, and its demographics, are shifting so quickly it would be a huge miss for companies not to be thinking about how their culture can reflect the broader universe or potential customers and users.
This isn’t about quotas or raising or lowering bars, it’s about capturing opportunity.
This was such an engaging and energizing conversation for both Y-conne and I. We hope you enjoy listening as much as we enjoyed recording it.
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Walking through Madison Square Park a year ago, @schlaf talked about transitions, something he knew a lot about.
I first met Steve when he was a junior investing partner at RRE, a venture capital firm in New York City. At the time, Schlaf had the NYC startup scene in a chokehold. He had a reputation for hustling hard and winning some of the hottest consumer deals in the city. He was charismatic, he was aggressive, and then, he was gone.
At first, he left RRE to do a firm of his own, then he joined Primary as a Venture Partner, then struck out on his own again to blend a CEO coaching practice he was developing with a new chapter as an angel investor.
In the park that day last year, he talked about a new evolution of his practice. He'd gone deep on the study of transitions. As someone who'd lived through many in his career, he felt a connection to the subject. As conversations and calls for help with career transitions flooded into his coaching practice, he felt a calling.
That calling is still taking shape, but the current iteration of it is Downshift, a cohort-based "decelerator" for high achievers in career transitions. Downshift gives these strivers a place and permission to slow down and take inventory before embarking on the next chapters of their careers.
Some takeaways from this conversation —
Steve left venture burnt out from the nonstop pace and transactional nature of venture. He wanted more authentic relationships not based on dealmaking. Venture can feel like a “legalized casino” focused on status and wealth generation rather than substance. Instead of constantly being in meetings and pitches, he needed to slow down and have space to think and process.
In hindsight, Steve would approach venture differently:
— Scheduling no meetings before noon to allow time for research and deep thinking.
— Partnering only with people who share similar values.
— Balancing effort and recovery to avoid burnout.
— Being more upfront and decisive with entrepreneurs, trusting his intuition.As a coach, Steve helps clients navigate major life/career transitions and “ego deaths” as their identities and narratives break down. In practice, that looks like holding space with presence and empathy rather than driving them to specific outcomes, helping them see patterns and make decisions from a place of clarity and agency, not fear, and slowing down to allow emotions to be felt and processed. This method helps his clients reach a sustainable and ultimately stronger place.
The prompt to reach out to Steve was seeing his work show up outside of the usual startup circles, notably Bobby Kim, founder of the streetwear brand The Hundreds. Bobby wrote —
"Maybe it’s just me.
But I keep running into the same conversations around career crisis, purpose, and transitions. Several times a week, I’ll meet up for lunch, sink into a DM, or sift through a Telegram chat, and a friend will confide that they’re experiencing a tough time. When I comfort them, they are surprised that they’re not the only ones struggling with finances, that other industries aren’t immune to existential threats. They sigh relief when they realize that most everyone I know is confronted with formidable questions of their lives and futures."
He goes on to cite Steve's work and relate it to a wide range of industries with a similar theme. It felt like a good time to sit down with Schlaf to dive deep on his work and this current moment.
When I approached Schlaf about sitting down to talk about his journey, he had the vision of filming in Central Park. A daunting request, but one where teamwork really did make the dream work. The visuals were stunning, and the conversation clocked in at nearly 3hrs (don't worry, we edited it down to something much more manageable).
The park lent an incredible vibe. You'll hear notes from a nearby saxophone, people stopping to say hello, birds chirping, and general movement of the city. We really love how this one turned out, and hope you enjoy listening as much as we enjoyed having it.
— Bryce
As always, if you or someone you know has a company that could be a fit for and investment from indie, don't hesitate to reach out.
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In April 2015, I read an article that elicited a reaction I’d only had a few other times prior.
We had just closed applications for our first round of experimental indie investments and had made most of our selections.
The article in question was titled Instagram’s TMZ, not exactly a title that would typically grab the attention of a Mormon dad in Utah. But I was captivated by the story and the mystery of the founder known only by her first name, Angie. By design, she was not the face of The Shade Room (TSR), that was a distinction for her large and growing audience of “Roommates” who kept the comments buzzing and the scoops flowing.
Any fan of pop culture knows that it's largely downstream of Black culture. Control the headwaters of culture, and you can shape the conversation around it. That’s the opportunity that I saw in TSR, but the risk was that they would follow the playbook of the other modern media giants of their generation - Buzzfeed and Vice. Unlike the latter, who had built their own technology and properties from the ground up, TSR leveraged existing social channels to go directly to their audiences. This was as practical as it was counterintuitive and ultimately led to a meaningful part of the TSR success story, while Buzzfeed and Vice have drifted into obscurity and irrelevance.
A few takeaways from this conversation:
The Shade Room's journey and growth:
Angie started The Shade Room in 2015 with a vision of it becoming influential and a cultural game-changer, despite having only a few thousand followers at the time. After indie's investment, Angie was able to take that confidence and has grown significantly since then. The Shade Room has become an integral part of Black culture and media, with a highly engaged community called "The Roommates".Angie's approach to building The Shade Room:
Angie has purposefully kept the company bootstrapped, avoiding taking on additional investment in order to maintain ownership and control. She's turned down multiple 9-figure acquisition offers, driven by her long-term vision and purpose rather than financial gain. As a Black media company representing Black culture, The Shade Room faces increased scrutiny. Advertisers have undervalued The Shade Room's audience compared to other media outlets, like BuzzFeed and Vice. But because she kept her independence, the Shade Room was able to outlast those over-funded media companies.Advice for those starting out:
If Angie was starting the Shade Room today, she'd follow these three pieces of advice —
1) Speak to yourself and your own interests.
2) Listen to your audience.
3) Truly know your audience.Recording this conversation in Angie’s home was a beautiful contrast to when we first met. Her growth as a business builder and as a person has truly been highlight of my professional career. There’s no doubt in my mind that there’s much more runway ahead for her and TSR. Hopefully that can all happen without landing me in any more diss tracks…
We hope you enjoy listening as much as we enjoyed recording this one.
And as always, if you’re working on something that could be a fit for indie, or know someone who is, don’t hesitate to reach out.B
— Bryce
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A few years back, I got a DM from a founder wanting to meet and swap stories about adventures in entrepreneurship. Despite being backed by some of the top VCs in the world, they were taking a very different approach from the classic VC blitzscaling playbook. As we sat on the back patio of a bar in Brooklyn, it was clear that how Jori and his founding team at Linear were building was very aligned with how we were encouraging founders to consider building through indie (note - we are, sadly, not investors in Linear).
Years and a Series B later, the Linear founders have continued building their company on their terms.
A few weeks back, I had the opportunity to sit down with Jori’s co-founder, Karri Saarinen, at his home in California for a wide-ranging talk. We covered everything from their time at some of the biggest hyperscalers of the last wave (think AirBnB, Coinbase, Uber), to net-negative lifetime burn rate (they’ve basically never spent the $52M they’ve raised), to their version of “Founder Mode”, to Finnish potato farming.
A few notable takeaways from this conversation:
Building a Different Kind of Company
Linear aims to build a company and product in a way that differs from typical Silicon Valley startups by focusing on product quality and craft rather than rapid scaling. By maintaining profitability and controlled growth instead of burning through venture capital, they’ve been able to build a venture-scale company without giving up optionality. The founders draw on their experiences at companies like Airbnb and Coinbase to avoid pitfalls they observed there, like culture dilution from hyper-growth. They’ve emphasized a small, high-quality team over rapid hiring.Product and Growth Philosophy
Linear prioritizes product quality over growth hacks or aggressive marketing. By focusing on making the product so good that people naturally talk about it, they’ve been able to capitalize on word-of-mouth from satisfied users as a growth strategy.Founder Approach
Karri emphasizes the importance of founders staying connected to the product and the craft. Because they care deeply about the output and quality of work, they can avoid creating unnecessary management layers or processes. Karri advocates for founders to think critically about standard startup advice and find their own path that aligns with their strengths and values.Remote Work and Culture
Linear is fully remote, which they see as an advantage in maintaining focus and avoiding unnecessary distractions like office design. The company emphasizes clear communication and looks for employees with strong communication skills to thrive in a remote environment. Remote works if the founders want it to.I really loved this conversation with Karri.
It highlights for me that there really is a new wave of ultra ambitious founders who are finding a way to stay true to themselves and their visions by focusing on what matters, and putting themselves in a position to controlling their own destiny. Linear, Vanta, Zapier, Webflow, and so many others are validating that growth at all costs doesn’t have to cost you everything.
I hope you enjoy listening to this conversation as much as we enjoyed recording it.
As always if you or someone you know are working on something that could be a fit for indie, don’t hesitate to reach out.
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In this conversation we unpack their journey of building a “lifestyle business”. Some takeaways:
— Chris and Brendan emphasize the importance of patience, focus, and long-term thinking in building a sustainable business. They challenge the notion that raising large amounts of venture capital is necessary for success by finding that being profitable allows for more long-term focus and creative risk-taking. Compounding growth over time can lead to significant results, even if initial growth rates seem modest compared to venture-backed peers.
— After the buyback, there was a shift in company culture towards greater ownership and cost-consciousness among employees. They introduced profit sharing and later reintroduced stock options to align incentives with long-term growth. They stress the importance of building a team you enjoy working with and taking risks on people with growth potential.
— Wistia focuses on solving big problems in large, growing markets rather than chasing short-term trends. They’ve learned to be patient with new product initiatives, looking for early qualitative feedback before expecting significant revenue. The company balances short-term metrics with long-term vision, understanding that meaningful growth often takes time.
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— Shift in Funding Landscape:
There has been a significant shift in the funding landscape, with a decrease in year-over-year growth rates for SaaS companies. This change underscores the need for venture capitalists to adapt and explore different investment opportunities. We do our best to highlight the importance of diversifying investment strategies in venture capital, emphasizing the need for alternative paths and approaches that deviate from the conventional SaaS-focused model prevalent in the 2010s.— Importance of Exceptional Founders:
The conversation points out that exceptional founders who want to do something differently are crucial. It emphasizes the value of supporting founders who are not just following the standard playbook but are instead looking to create something unique.— Zigging When Others Zag:
Delian shares the strategy of investing in areas that are less popular or overlooked by the majority. This approach is not dissimilar to indie.— The Need for Support Systems:
Whether it’s external support systems or family, founders need support systems to endure the grueling situations you encounter when building a generational company. Contrary to conventional wisdom, having children can allow you to get more done faster by clarifying the truly important over the urgent. -
Product-market fit requires both customers willing to pay and stay. It’s not just about initial sales, but also retention. Early-stage sales should focus on research and understanding customer problems rather than immediate revenue generation. Founders often skip this crucial research phase.Abstract solutions require focusing on specific problems rather than leading with the technology itself. To create urgency, you need to demonstrate how a problem is growing or intensifying for the customer. If a problem isn’t being measured or managed, it’s likely not a priority.Early adopters are often those early in their buying journey who are willing to experiment. They buy into the founder as a subject matter expert rather than expecting a fully-built product. Successful startups often start by focusing on a specific niche before expanding horizontally. Being highly specialized allows you to understand customer problems better than they do.Invalidation is a healthy part of the startup process. If you’re not invalidating assumptions, you’re likely not learning or going deep enough. Sales feedback is valuable for positioning and refinement, but product vision should come from founders or product leads. Salespeople should not drive product vision. Demonstrating expertise by setting boundaries on what your product does (and doesn’t do) can actually increase customer confidence.
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— Capital has no insights
Eric argues that venture capital alone doesn’t solve business problems, and having more capital doesn’t necessarily lead to better outcomes.— Compounding value vs. negative value
The importance of building companies that compound positive value over time, rather than scaling prematurely and compounding negative value. Funding should primarily be used for experimentation and scaling proven business models, not for scaling unproven ideas, because it’s easy to compound negative value if you’re not paying attention to the right things.— Vanity metrics vs. intrinsic value
The industry often focuses on vanity metrics like growth rates and valuations, rather than building long-term intrinsic value and durable businesses. The venture capital industry’s incentive structures often encourage behavior that may not be in the best interest of building sustainable businesses. It’s important to maintain a long-term perspective on building value, rather than getting caught up in short-term growth or fundraising cycles. In many tech businesses, there are often diseconomies of scale rather than economies of scale as companies grow.— Playing the game on your own terms
CEOs and founders are ultimately responsible for making disciplined decisions about resource allocation and scaling. While entrepreneurs can’t completely ignore the “game” of venture capital, they should focus on building value on their own terms rather than getting caught up in comparisons or unrealistic expectations. -
Some takeaways:
— There’s a significant gap between the hype around AI and its actual implementation in businesses. Many companies are still in the experimental phase, with few AI solutions in production. The main barriers to AI adoptions are technical challenges, cost considerations, and lack of expertise. We’re still very early in realizing AI’s promise.
— AI adoption was slow, then immediate. In a pre-ChatGPT world, the focus was on convincing companies to care about data science and machine learning. Post-ChatGPT, there’s been an explosion in demand, with companies actively seeking AI solutions.
— Most companies are still in the proof-of-concept stage. There’re limited production-ready AI use cases, which hinders adoption. But with major cloud providers (Microsoft, Amazon, Google) aggressively pursuing AI strategies, that’s bound to change. There’s constant evolution in model performance and capabilities. Companies need to view AI as a continuous investment, similar to cloud infrastructure, rather than a one-time project.
— Tribe’s approach to AI implementation is what made it such an interesting investment for indie. Their focus on education to help companies understand AI's potential, and emphasis on quick, cost-effective proof of concepts to demonstrate value, means they’re positioned to continue rapidly growing. As a services business, they’re able to help companies balance cost with value creation, navigate rapidly evolving AI technologies, and future-proofing AI investments.
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A few takeaways from this conversation:
— Early crypto applications were challenging to use and primarily attracted tech enthusiasts and speculators. Over time, the technology matured, making applications more user-friendly and broadening the user base. While there’s still a long way to go, the maturation of the technology also led to a shift in focus from speculative gains to building durable and sustainable businesses.
— A significant issue in the crypto space is the short-term focus of many projects, prioritizing quick liquidity events, like token generation events (TGEs), over long-term business building. This emphasizes the importance of founders who are serious about building lasting companies rather than those looking for quick gains.
— Market cycles heavily influence behavior in the crypto space. Bull markets attract a lot of attention and speculative projects, while bear markets tend to wash out less-committed participants, leaving behind those genuinely interested in the technology. smac notes that bear markets often lead to better quality projects and more serious builders.
— Events like the FTX collapse and the Silicon Valley Bank (SVB) crisis reinforced the importance of self-sovereignty and distrust in traditional institutions. Compound's belief in the growing importance of self-sovereignty extends beyond financial institutions to healthcare, education, and data institutions.
— Compound looks for founders who are serious about building their companies and have a long-term vision. They value founders who are thoughtful about their projects and not just looking for quick liquidity.
— How crypto can be applied in areas like distributed energy and healthcare data. We also highlight the potential of decentralized physical infrastructure networks (Deepin) and decentralized science (DeSci) as promising areas for future investment.
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When you end an essay with a line like:
"Majoring in computer science today will be like majoring in journalism in the late 90’s.”
You’re bound to ruffle some feathers. In the case of Chris Paik’s “End of Software” essay, not only were feathers ruffled, but the entire farm was flustered. And then the pitchforks came out…
Given the violent response to the piece, both positive and negative, we approached Chris with the idea of adapting the Jimmy Kimmel “Mean Tweets” skit to address some of the critics and dive into the nuances of such a bombastic proclamation. What we ended up with was an incredible, and occasionally comical, deep dive into his thinking and observations around the innovation that’s emerging at the intersection of software development and Artificial Intelligence.
Some insights from this one —
The cost of creating software is approaching zero, which will fundamentally change its nature. Software is shifting to a new phase where it will be created on-demand to serve a specific intent and then disappear. This is similar to how content creation and distribution costs went to zero with the internet, enabling ephemeral user-generated content.People are lazy and want software that routes them directly to what they want with minimal effort. Platform providers that can best deliver on user intent will monopolize the market, just as social media platforms monopolized attention.Solving the discovery and distribution challenges amidst this coming explosion of near-zero cost software will be the source of the biggest future opportunities and venture returns.While AI will make average software more accessible, it will also shift the curve to enable the creation of revolutionary new software that is better than what exists today. -
This is really one you should watch on our YouTube. Like, all of them are. But this one has Will going to a White Board.
What if we could know whether the business idea you can’t shake is worth pursuing? What if we could ensure that we're pairing the right ideas with the right capital sources to ensure the best possible outcomes? Will Quist, from Slow Ventures, is on a mission to answer these question and more for founders with subject matter expertise and high opportunity cost.
To that end, he’s designed the Slow PhD, a program that embraces the idea that "Important companies and successful businesses can’t be hacked, forced, or faked.” Through a rigorous engagement process and step by step opportunity analysis, Will hopes to target more of the right people at the right opportunities with the right sources of capital behind them.
There has been a decoupling of awesome products from awesome companies and awesome companies from awesome venture capital investments. Just because a product is great doesn’t mean it will make a great company or require venture capital. A lot is knowable early on about a company’s prospects.The abundance of venture capital in recent years may actually be a bug, not a feature, for founders. When capital was scarcer, getting funded was a stronger signal that an idea was worth a founder’s opportunity cost to pursue. Now, founders are sacrificing a lot of their valuable time without enough diligence.Venture capital should be used to fund experiments to test novel hypotheses about how the world works that could be wildly valuable if true. The experiments should generate clear true/false signals without requiring too much capital. This gives optionality to pursue bigger opportunities if the initial hypothesis is validated.If founders become better “investors” in their own companies by deeply understanding their business model, capital efficiency, and growth levers beyond just building great products, it could lead to more efficient allocation of capital and better venture outcomes overall. But truly great venture-scale companies may still be constrained more by the supply of innovative ideas than the supply of capital.
This conversation was an attempt to give a preview of the PhD program and explore ideas around its perimeter. Take aways from this one— -
My friend, Michael Dempsey, Managing Partner at Compound, and I have an ongoing thread about the intersection of indie ideals and his areas of focus in deep tech. Most of these conversations happen over meals or online, so we decided to dive in a bit with the cameras on.
Our conversation was as fun as it was wide ranging.
I’ve watched for years as Michael has built Compound into a research focused, thesis-driven firm that has moved from the edges to the center of some of the hottest investment areas today. We get into details behind his early conviction around AI juggernauts like RunwayML and Wayve, to new themes they’re exploring in crypto and biology.
Some quick takeaways and highlights to look for —
There’s a trend of deep tech startups pursuing overly ambitious “narrative rotations” by constantly expanding into new areas, which Michael aptly calls a “Ponzi scheme of ambition.” This is driven by the need to justify raising large amounts of venture capital.His bias towards building one big business in a massive market rather than narrative expansions. For shelling point investments, like SpaceX and Palantir, the focus is on owning and expanding a principle or market over time, rather than narrative rotations.Compound’s approach to investment themes that are considered “too early or too ridiculous” with no real customers yet, and funding those contrarian opportunities.The value of developing specific year-by-year theses on how certain sectors will play out, acknowledging that 80% may be wrong but aiming for the 20% that are very right. You only really need to be right twice per fund. -
We invited our friend, Reggie James, to help unpack what's happening in hardware and break down what's behind many of the recent negative viral product review videos currently hitting the internet. Reggie is a longtime friend to indie and prolific advisor to many of this new crop of hardware startups in market and in development. He cuts right to the point with strong opinions and spicy takes that may not be obvious to the casual observer. You'll also hear a view on technology and culture that extends far beyond any single device.
In this one, we touch on —
The disconnect between the world of venture capital/tech startups and the reality of many creatives/builders who don't view capital as a tool for building. With AI enabling code generation, this group could potentially produce venture-scale outcomes without relying on traditional funding.The tech industry has struggled with effectively communicating and branding themselves, especially after the era of Steve Jobs and Apple's lifestyle branding. This has led to insular narratives and misunderstandings around emerging technologies like crypto and AI.Physical products and hardware still hold importance for branding and communicating a clear lifestyle/use case, unlike software companies that often neglect this aspect. Successful hardware brands like Teenage Engineering have a distinct identity tied to their products.Devices like Humane's are attempting to break people's "addiction" to smartphones by offering an alternative that frees the user's hands and gaze, challenging the narcissistic nature of current mobile devices.Niche hardware products like USB Club's file-sharing network cater to specific communities (DJs, designers, etc.) and could enable new economic models by tying hardware to digital networks and data storage.There is a potential cultural shift happening around the perception of manufacturing/trade jobs, with younger generations being more open to these paths instead of defaulting to universities and white-collar work. -
One of the most frequent requests we get is to hear directly from indie founders. Today's conversation is just that. And we did it in style. James Nord, founder of Fohr, has had a front row seat to indie having been one of the very first investments we made. In turn, I've had a front row seat for their growth from hundreds of thousands in revenue to 10s of millions.
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I had the opportunity to know Christina Cacioppo early in her time at Union Square Ventures. Always whip-smart and ever curious, we found ourselves drawn to similar founders and edges of emerging markets. When her time at USV ended, we lost touch. She moved from NYC to San Francisco, took a job at Dropbox, and carried on with her post-VC life.
Fast forward a few more years, and she’s leading one of the fastest-growing SaaS businesses as the co-founder and CEO of Vanta. A few weeks back, we got to reconnect for a long overdue catch up at Vanta’s office in San Francisco. Initially scheduled for 30 minutes, our conversation expanded into nearly two hours of lessons learned, hilarious anecdotes, and a genuine reconnection between two old friends.
Although Vanta is not an indie portfolio company, you’ll quickly notice Christina’s indie-aligned approach to starting and scaling Vanta. From her quick product iteration, to early paying customers that led to early profitability, and intentional decisions around how and when to best capitalize the business. We cover it all. I’ve watched a bunch of Christina’s past interviews and feel like this one gets closest to the intensely whip-smart and soulful person she is.
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