Jason Jacobs wants it all. 

As a father to young children, he wants to be active in their lives, but as an ambitious founder, he’s compelled to build and chase down opportunities that often require sacrificing the time with his family that he longs for. This is not a new tension for a repeat founder, but the current moment has presented Jason with an opportunity to reflect and explore whether the new tools and timing available today may make this next time... different. 

I first met Jason when we funded his startup, Runkeeper, the first fitness tracking app for the iPhone. It was a fascinating ride for the both of us as Jason piloted a rocket ship whose engine stalled as he pushed to tell a story that made investors swoon and customers scratch their heads. Runkeeper ended as a success via its acquisition by ASICS in 2016 and started a new chapter for Jason as a successfully exited founder. 

After a false start raising money for his first idea post-Runkeeper, Jason began to develop a process for discovering what comes next for him in his pursuit of entrepreneurial purpose and impact. He applied this process first in climate, ultimately founding the venture capital firm, MCJ. Recently, he’s begun the process again with The Next Next which he describes as:

My hope with this expedition is I can unpack what we as humans need out of work in this next era, what is possible with emerging tools, and how they can be applied most effectively to building startups. I am hoping it will lead to my next venture (iteratively, using this newsletter as an important feedback tool), and that if I find success with this new playbook, it can be a template for a new way of company building that many others will follow.

Some takeaways from this conversation:

- Chasing trends or investor expectations at the expense of your core mission can derail even a promising startup. Jason candidly admits that Runkeeper lost its way when it tried to expand beyond its core running focus into the broader “Health Graph” vision. This pivot, driven by the allure of venture capital and external validation, created internal friction and diluted the company’s identity.
- Realigning your business with its foundational strengths when navigating challenges. Jacobs’ decision to refocus Runkeeper on its original running mission marked a turning point for the company. By cutting unnecessary initiatives, streamlining operations, and regaining profitability, the team was able to position itself for acquisition by ASICS.
- The importance of “staying true to your weirdness” and building in a way that aligns with your values and strengths. Whether it’s rejecting the grind culture of traditional startups or refusing to compromise on family priorities, his journey highlights that success doesn’t have to come at the cost of personal fulfillment. For Jacobs, autonomy is not just a preference—it’s essential for achieving greatness.
- Learning in public as a superpower. After Runkeeper, Jacobs embraced the power of learning in public by sharing his explorations into climate tech and, later, AI through newsletters, podcasts, and social media. This approach not only helped him build credibility in new fields, but also attracted like-minded collaborators who became part of his growing tribe.
- Jason is now on a mission to prove that it’s possible to build impactful companies without sacrificing family, health, or balance. Leveraging AI tools to reduce operational overhead, he aims to build differently while maintaining control over his time and energy.

I have an expansive relationship with Jason, and I think that comes through in the video. We cover much of the struggles he had with investors, managing his psychology as a founder, and his process of discovery that he has unquestionable conviction in. 

My hope is that people will see some of themselves at various stages in Jason’s journey and find inspiration in both his mission and his process. 

I hope you enjoy watching as much as we enjoyed recording it.

Mikey Shulman is having a great time.

He’s running a rocket ship of a company, has $100M+ in funding from some of the top VCs, and is working on an opportunity that he’s passionate about.

Mikey hit my radar because of a text from my friend TJ. His firm was an early backer of Suno, and he said that if any company they work with was going to hit our “4 Min Mile” challenge of $100M in revenue with fewer than 10 employees, it'd be Suno. 

That was the conversation I was planning to have with Mikey when we stepped into the studio at Suno HQ in Cambridge. What unfolded was a conversation with much more nuance and range than I’d originally anticipated. 

Some takeaways:

• Mikey emphasizes the importance of fun in AI development, contrasting with the industry’s focus on productivity gains. He sees AI as a tool for enhancing human creativity in music, potentially leading to new heights in artistic expression.
• Shulman sees AI as a tool that, like humans, learns from past data to create new expressions. He disagrees with the notion that AI can only look backward, arguing that it can be a powerful instrument for innovation in music when guided by human creativity.
• The company’s rapid growth was aided by staying somewhat removed from the AI hype cycle, allowing them to focus on building value and iterating quickly based on user feedback.
• Despite raising significant capital, Shulman actively tries to avoid fixating on the company’s war chest. He believes constantly thinking about available funds can distort decision-making and lead to inefficient resource allocation.
• Shulman credits much of Suno’s success to his talent for hiring and building a strong team, rather than his own ideas. He stresses the value of finding people who are passionate and committed to the company’s mission.

As Suno approaches the $100M mark with a much bigger team than 10, I can’t help but wonder if there’s more indie can be doing to encourage and support founders who are thinking similarly about small teams with ambitions for massive scale.

We’re doing that already through our direct investing, but I wonder if there’s a program we could put together that would involve investment and shared learnings from a group of like-minded founders working towards a similar goal that could help the whole get there that much quicker.

If you have thoughts on this, please share. It’s something we’re actively thinking through, and I would value additional ideas and points of view.

As always, we hope you enjoy watching this one as much as we enjoyed recording it. If you’re working on something with a similar ethos to Suno and looking for investment, don’t hesitate to reach out.

— Bryce

Today’s conversation with Mike Salguero went in a direction I really wasn’t anticipating. Initially, I was interested in talking to Mike because he’s lived multiple lives as a Founder. 

First, buying and then raising 10s of millions for a crafts persons marketplace called Custommade.com. Then, after winding down Custommade, starting what he would term a “hobby business” to recover a bit from the toll a large “venture scale” swing took on himself, his health, and his family. 

Interestingly, the big swing didn’t work. But the less ambitious “hobby business” has grown to $500M+ in revenue with zero outside funding. 

In our Indie Era of Startups talk, we theorize that:

— WE'RE ABOUT TO SEE THE BIGGEST CLASS OF SV-EDUCATED FOUNDERS IN HISTORY
— THEY'LL BUILD INDEPENDENT, INNOVATIVE BUSINESSES THAT WILL CHANGE THE WORLD
— THESE FOUNDERS WILL LOOK FOR MORE FLEXIBLE, SUSTAINABLE, AND ALIGNED FUNDING PARTNERS

Mike is a great example of those ideas personified, along with Alan from last week's video. The movement we’re building indie to support is happening, and Mike’s experiences and lessons learned are emblematic of many returning venture backed founders and early employees.

Some other takeaways from this one:

The power of constraints — Mike built a $550M empire on just $10K, proving you don’t need hoards of VC cash to disrupt an industry. The constraints he placed on the business early allowed ButcherBox to maintain control and focus on long-term growth rather than chasing short-term metrics to please investors.

Work-life balance isn’t just fluff — Mike built ButcherBox while prioritizing taking care of his body and his growing family. This approach demonstrates that success doesn’t always mean sacrificing personal well-being, and can actually lead to more sustainable growth and better decision-making.

Playing the long game — With a 25-year vision, ButcherBox is aiming for iconic brand status. This long-term perspective allows the company to focus on transforming the meat industry and building a lasting legacy rather than seeking quick exits or short-term gains.

The “barbell strategy” is pure hiring gold — Pairing fresh grads with industry vets creates a powerhouse team. As a VC backed founder, he was pushed to hire the most pedigreed and impressive over the most experienced or most hungry. This unique barbell approach combines the energy and fresh perspectives of young talent with the deep experience and mentorship capabilities of seasoned professionals.

Doing things you can’t at a VC backed Startup — When Mike said “hit our goals, we’re going to Mexico,” the team crushed it. A VC run board would have shut down the idea as not worth the significant expense but he was able to deliver on his promise even when it hurt the wallet. This commitment to following through on promises, no matter the cost, has built a culture of trust and motivation within the company.

The final, and I thought most interesting, takeaway from this conversation was Mike’s idea that companies know what they want to be. Finding and being true to that has been the key to his success and ignoring it was the foundation of his failures. 

With Custommade, he wanted it to be something it didn’t want to be — a massive marketplace for craftspeople to connect and transact. What it wanted to be was a simple listing service. 

With Butcherbox, Mike wanted it to be a hobby business so he could outsource everything and collect a check every month from a beach. But what the business wants to be is a force within the world of meat for better quality products and more humane treatment of the animals and land. 

In both cases, and in different ways, he’s fought what the company is telling him about what it wants to be. When he’s embraced his role as a steward for an idea, a business and a culture that will continue long after he’s out of the day to day grew.

That’s what I took away from this one. I’m curious about your take away from this one, too. 

Let’s try something new this week — leave a comment on the YouTube video with your takeaways or thoughts, and any experiences you’ve had that relate to what Mike shares. Don’t hesitate to call BS if there’s something you think he or I miss the mark on. 

I’ll be monitoring and responding to as many comments as I can. Hoping this will be a fun addition to our weekly tradition of sharing these conversations and artifacts with you. 

As always, I hope you enjoy listening and commenting as much as we enjoyed recording this one. 

And if you’re working on something you think could be a fit for an investment from indie, please reach out.

— Bryce

"Would you be mad at us if we raised more money?"

That was the text I got late one night from Will Pearce, co-founder and CEO of Dreadnode, a company we'd funded about nine months prior.

I'd gotten to know Will through a cold DM he sent me. The DM had nothing to do with tech or investing, just starting a conversation. At the time, Will was working at NVIDIA as an AI red team lead putting him at the cutting edge of AI and ML security. As we got to know each other, it was clear he had a large vision for where the puck was going for the broader market and where his expertise and insights could create the foundation for building the leading company for offensive AI security.

I offered to put together a small round to put he and his co-founder, Nick Landers, in business. We filled the round out with several value-added angels and were off to the races to build product and company with indie ideals at the core. And it worked!

Within months, they were signing contracts with the top names at leading research labs and hyper-scalers. On several occasions, they were even profitable! And then the VCs noticed.

Shortly after our round closed, the word started to spread on what the team at Dreadnode was building. Then the emails started. The early answers were nos and not interested, but as demand from customers grew and incredible, early potential team members started coming out of the woodwork, these high class problems were becoming very real problems.

The team found themselves turning away customers and potential hires as their demand outstripped their resources. Thus, the late night text.

The text led to a conversation that led to a formal fundraising process and ended in the announcement last week of Dreadnode's $14M Series A led by Decibel, a top tier firm focused exclusively on security.

In today's video, we unpack the conversation and process that unfolded after that late night text. We dig into why Will may have had concerns that I, and indie, would be upset or not supportive of their decision, and learnings from two very green and very technical first time founders getting sucked into their first proper fundraising process. 

I hope what comes through in video is something I've written often — we are not anti-fundraising. But we believe that the best way to improve your odds of building a generational company that can attract world class customers and investors is to focus on the former, the latter will come. And when they do, you'll be in a position of ultimate optionality that empowers founding teams to pick exactly the partner they want, on the terms they want, and get back to build the company they want. 

It seems obvious, but it runs so counter to the advice and examples that get celebrated in the startup world. In the case of Dreadnode, they were able to do just that — work with the partner they wanted on the terms they wanted. And, as an added benefit, they were effectively able to skip 2 or 3 interim rounds of funding and skip straight to a fully baked Series A. 

Our goal with today's video was to put some personalities and experiences to that narrative and I think it comes through here. As always, I hope you enjoy watching it as much as we enjoyed recording it. 

PS — if you see any of yourself in the Dreadnode founders, don't hesitate to reach out to discuss what you're building and whether indie could be a fit for you too. 

It is incredibly rare to have your startup become a verb. Google and Uber immediately come to mind. But what about when a group of strangers or friends with shared interests decide they want to get together? They, Meetup. 

Scott Heifferman didn’t set out with becoming a verb in mind but he certainly started Meetup with the intent of building something big and impactful. And on those dimensions he delivered in spades. Along the way he sold 30% of his company for $1M to Tim Draper’s DFJ (funny story around the 36 min mark), raised from other great investors (Brad Burnham from USV makes a cameo in the video), met face to face with Mark Zuckerberg who also decided that getting groups of people to meetup would be important for Facebook too, going so far as to run their very first Super Bowl ad promoting their meetup competitor product. There are so many great stories and anecdotes in this one. 

In our effort to mine Web 2.0 ideas and playbooks for applicable lessons for this current wave to startups, this conversation delivers in spades. A few take aways:

— The Origins of Meetup and Community Building: Heiferman reflects on how 9/11 and experiences like Burning Man inspired Meetup’s mission to foster real-world connections. He emphasized the importance of creating tools that empower people to form communities and build belonging offline, using the internet as a catalyst.

— Early NYC Tech Scene vs. Silicon Valley: Heiferman shares stories of the scrappy, experimental nature of the 1990s NYC tech ecosystem, contrasting it with Silicon Valley’s more established infrastructure. He recalls starting iTraffic with maxed-out credit cards and seeing startups like Razorfish and DoubleClick shape the local scene.

— Facebook’s Competitive Threat: Heiferman recounts how Facebook’s groups feature directly competed with Meetup, even running Super Bowl ads mimicking its concept. This competition influenced his decision to sell Meetup to WeWork, as Facebook’s scale and resources were hard to match.

— Critique of Modern Marketplaces: Heiferman critiques platforms like Uber and DoorDash for extracting excessive margins from workers and businesses. He advocates for a fairer market economy where technology empowers individuals rather than exploiting them.

— Future Vision and Lessons Learned: Looking ahead, Heiferman expresses interest in building impactful projects outside traditional VC structures. He emphasizes the need to focus on creating products that energize people, deliver value, and prioritize meaningful societal impact over maximizing profits.

One thing that especially stood out to me in this conversation was a reminder of how “people” were so core to Web 2.0 ideals. Whether it was getting people to connect online or off, fostering real and personal connection was such an important driver for innovation at that time. When today’s headlines are so  filled with stories that seem to pit people against algorithms, Scott’s sentiment is a refreshing reminder that technology at it’s best is a tool for enhancing our lives, not eradicating them. 

On that theme, a comment Scott made has been rattling in my head ever since. At around the 40 min mark he says something along the lines of “AB testing is the price you pay for not having a pulse on people”. In this conversation he talk a lot about energy, following the energy of individuals and his own energy and interests. He seems energized to build again and we talk a bit about what’s next for him and how his time working in an Amazon warehouse informed his thinking around what problems he wants to tackle. We can’t wait to see where he goes with all that energy. 

This was a ton of fun to connect with Scott and Brad to revisit the Meetup story. We hope you enjoy listening as much as we enjoyed recording it. 

This is a spicy one! 🌶️

This week we sat down with Brandon Arvanaghi from Meow.com to discuss his journey from money burning crypto company to profitable fintech. His tweet last year about hitting the profitability milestone had some obvious, and some less intuitive, take aways from their experience. Everything from opting out of the VC treadmill to applying the Costco model to low margin financial services. 

Some other key takeaways: 

- Brandon built Meow to $1B+ in assets with just 12 people by rejecting Silicon Valley’s “growth at all costs” playbook. His secret? Being profitable and savage about staying lean. “The future is lean - you can’t go from 1000 people down to 10 and pass back savings, but you can stay lean from the start.”
- Brandon’s building Meow like “Costco for financial services” - focusing on rock-bottom prices and passing savings to customers vs the typical VC-backed approach of sneakily raising prices to hit growth targets. He believes in 5-6 years, when pricing becomes fully transparent, this will be the only way to compete.
- “VCs are lemmings” — Brandon says the 18-month runway advice is a psyop to keep founders dependent on VCs. He argues most VCs just follow each other and care more about looking good to their LPs than helping build real businesses. The rare exceptions? Maybe 1 in 20 VCs.
- “Stay in the game, win the game” - Brandon argues real innovation doesn’t require betting on non-existent markets. His advice? Pick obvious bets without market risk, stay profitable, and make them 10x better through execution. “How can you not make a generational outcome if you just keep pushing the ball forward?”

Big thanks to Brandon for really going there with us. He shares lived experience around many of the ideas we've been advocating for at indie for years. To see someone so fully embrace those ideas and find incredible success on the other side is great validation for others wishing they could go their own way too. 

We hope you enjoy listening to this one as much as we enjoyed recording it.  

Late last year, we sat down with Eric Ries, who fundamentally changed how we think about building startups through The Lean Startup. Only Eric can make corporate governance sound poetic. The conversation took an unexpected turn as we delved into what Ries calls "vampire founders" - leaders who feel immortal yet isolated, watching employees come and go while they remain eternally at the helm. This phenomenon stems from founders conflating their identity with their companies, leading to a uniquely lonely experience that differs markedly from traditional CEO roles.

The discussion revealed how the current startup ecosystem, flush with capital but short on genuine opportunities, has created a pressure cooker environment where founders often compromise their original values to fit institutional expectations. Ries argues that most entrepreneurs start with genuine idealism but get caught in a system that strips companies of their distinctiveness - what he calls being "surgically deboned". This process happens gradually through what Ries terms "gravity," where financial transactions unconsciously transmit values that pull companies toward conformity.

Perhaps most provocatively, Ries challenges the fundamental premise of shareholder primacy theory and suggests that the way we currently build companies is neither inevitable nor optimal. He points to examples like Anthropic's Long Term Benefit Trust as evidence that alternative governance structures can work, while arguing that the current system's defenders spend inordinate energy convincing everyone that the status quo is inevitable - a sure sign, he suggests, that it isn't.

Some key insights from this video:

-  The "vampire founder" phenomenon describes leaders who feel immortal yet isolated, watching teams cycle through while they remain unchanged

-  Most founders begin idealistic but face systemic pressure to conform, leading to companies losing their distinctiveness over time

-  The startup ecosystem has more capital than good opportunities, creating pressure to grow at unnatural rates

-  Traditional governance structures often force unnecessary compromises that make both founders and companies weaker

-  Alternative governance models exist and can work, but the system actively resists their adoption becoming widespread

-  Financial transactions always transmit values unconsciously, creating a gravitational pull toward conformity

-  The current startup system is defended not because it's inevitable, but because it's actually quite fragile

-  Most founders who achieve financial success still end up deeply unhappy due to the compromises they made along the way

-  Building trustworthy companies is actually more profitable than exploitation, but the system makes this hard to see

-  Change is possible - Ries points to how The Lean Startup went from radical idea to conventional wisdom in just a few years.

Making any kind of time bounded predictions about where AI will be in the year of our lord 2025 is a fools errand. But, we’re suckers for this stuff, so we asked Jackie from Tribe to revise the State of AI download we did last year and orient it to what she sees coming for AI in the enterprise in the new year.

No sooner did we record the conversation than OpenAI announced Stargate, Operator, and Deep Seek shot to the top of the App Store. And made the whole conversation form the week before feel dated. 

But dated is different than timeless and I think what Jackie does an incredible job doing is anchoring founders and executives on the timeless principles of leveraging AI to deliver ROI and unlock entirely new experiences. 

For this conversation, the key takeaway is that AI implementation is moving from theoretical to practical, with clear winners emerging based on their ability to drive real business value rather than just run experiments.

-The AI vendor landscape is shifting from a winner-take-all market to a more competitive space, with Anthropic emerging as a serious challenger to OpenAI. Companies are increasingly comfortable switching between different AI models based on specific needs and cost considerations.

-Three areas showed clear product-market fit in 2024:
Enterprise ChatGPT implementations
Customer support automation
Code generation tools (with Google reportedly generating 50% of their code using AI tools)

- Many companies are stuck in “POC Purgatory” - running small AI proof-of-concepts that never scale to production. The successful companies are those making real commitments and showing patience through initial iterations.

-The biggest barriers to AI adoption aren’t technical - they’re cultural and organizational. Senior engineers and executives often resist AI tools while junior staff embrace them. Success requires leadership commitment and openness to changing how work gets done.

- Private equity firms are emerging as surprising AI innovators, focusing on implementing AI in their portfolio companies to drive value. This is shifting PE’s reputation from financial engineering to technological transformation.

- “Agents” are becoming the dominant theme for 2025, with companies seeking to automate entire workflows rather than just individual tasks. There’s growing demand for “factories of agents” that can scale automation across organizations.

- The traditional lines between software and services companies are blurring. Service-heavy companies like Palantir are being valued more like software companies as they demonstrate scalable AI implementation approaches.

- Marketing automation is emerging as the next major AI opportunity, with companies seeking to both reduce costs and improve ROI through automated content creation and campaign optimization.

- Companies that don’t move beyond experimentation risk falling permanently behind, as AI is compressing innovation cycles and creating growing gaps between leaders and laggards.

This was a wild ride of a conversation with someone who’s in the trenches with a wide range of enterprise customers. Her perspective and insights are invaluable. I hope you enjoy listening as much as we enjoyed recording it. 

And if you are looking to get started with or level up AI within your company, don’t hesitate to reach out directly to Jackie at [email protected]. 600+ of the best AI engineers on the planet are standing by.

On my flight to NYC last week, I casually asked if there were any events happening in the city while I was there. 

Reggie, who you may remember from his New Hardware video, and as the person who coined the term “indie-pilled”, replied that we should do one of our own. 

So we did. 

Thankfully we had our cameras in tow and were able to record the conversation. It turned into a nearly 2hr Q&A on all things indie, the current state of venture, the evolution of seed, the role of secondaries in venture, and some funny untold indie lore. 

In the video, Reggie mentions a piece he recently wrote titled “Lies My Teacher Told Me”, which set some timely context for this event. 

From the essay:

"The point of this is short. The new thing has to look like the new thing, which makes it hard to pattern match to the previous new thing. But pattern matching is at the heart of de-risking. This creates a weird loop of advice. 

The previous advice of zero interest rates and Snapchat as the last big thing for consumer software was to grow at all costs / monetize later / find novel behavior. 

Nikita Bier showed all of this was wrong with Gas App. Monetize directly in the V1. De-risk through known behavior. Growth inputs must be advantageously proportional to the monetization in the V1. 

There wouldn’t be a single VC that could share this advice. As a result, we’ve only had 1 US consumer internet win since Snapchat."

My sense is that that’s why indie is resonating so strongly this time around. As we wrote in our FACTS section:

"The game has changed. ZIRP-era playbooks of VC treadmills, pump and dump schemes, and growth at all costs have aged like milk. The future belongs to real builders, building real businesses. 

There’s a time-tested playbook for building generational companies — less time fundraising, more time building, with a focus on the fundamentals. Most of the iconic companies of the past, think Amazon, Microsoft, and Google as well as emerging leaders like Midjourney,  Vanta, and  Zapier, have followed a similar playbook.

We’ve built our firm from the ground up with this playbook in mind."

This is the future we’re been building towards, and it seems to be hitting an inflection point.

Thanks to Reggie and the team at Earshot for hosting us and making this happen on short notice. 

Hope you enjoy listening as much as we enjoyed having this conversation.