Episodios
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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.
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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.
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¿Faltan episodios?
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Chris Anderson can’t talk a lot about what he is up to these days. At least on camera.
His LinkedIn profile says he’s currently an Engineer at “Stealth". Prior to this current professional opacity, he was at Kitty Hawk, the electric aircraft maker founded by Sebastian Thrun (legendary Stanford Professor and former lead of Google’s self-driving car team that led to Waymo) and backed by Google Co-founder, Larry Page.
I became familiar with Chris while he was leading Wired Magazine as Editor-in-Chief. His work there was groundbreaking and set much of the pace, tone, and agenda for the early days of Web 2.0 and the Maker movement. After seeing a TedX talk about a side hustle he had selling cellophane bags of electrical parts and open source autopilots for DIY Drones I slid into his DM’s.
There is a lot of buzz around drones today, but note the date on that DM — November 3rd, 2010.
Little did I know at the time, that this little drone business was just beginning to grow from Chris and his kids packing orders at their dinner table to a proper manufacturing and distribution center along the border of Mexico.
As things happened, that DM turned into a conversation that turned into an investment in a company, 3D Robotics, that took Chris away from Wired and into the uncharted worlds of manufacturing, consumer hardware, and defense tech. He was early and 3DR didn’t play out the way that we’d all hoped but it laid the foundations for much of what he’s working on now — even though he can’t talk much about that publicly.
To say Chris has a knack for living in the future would be a massive understatement.
In this conversation we unpack his process for exploring possible futures — spoiler: Chris has started writing science fiction as a way to explore complex technological implications. He writes a book a month, using fiction as a computational tool to play out scenarios with artificial agents and see where they lead. We get into what he got right and what he got wrong about drones specifically and defense tech more broadly. And we discuss the culture of Silicon Valley, where we spar a bit on the amount of waste and wandering built into the system that ultimately leads to so many unexpected breakthroughs.
Since that first DM, he has become a dear friend, coconspirator, and sounding board for me. The unedited conversation here went on for nearly 3 hours (which reminds me that we really do need an “indie uncut” channel) but that’s the kind of person Chris is — generous in sharing his time, ideas, and insights.
I hope you enjoy listening as much as we enjoyed recording this one.
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Soleio Cuervo is more than a chin on the internet. He’s more than an early design leader at Facebook and Dropbox. And he's more than an epic angel investor.
He’s a truth seeker and truth teller. Or at least the truth as he sees it.
Soleio was one of Facebook’s earliest designers, joining in 2005 when the company was still finding its identity. During his six-year tenure, he helped shape Facebook’s culture of “move fast and break things,” where mistakes were acceptable but slowness was not. This philosophy was crystallized during the controversial launch of News Feed, which showed that transformative products could succeed despite initial user resistance if the team moved quickly to address concerns.
After Facebook, he joined Dropbox, first as an angel investor, then full-time in 2012 to lead design when they had just a handful of designers. The transition revealed stark cultural differences - while Facebook was a paranoid, competitive insurgent focused on speed, Dropbox prioritized reliability and stability, aiming to build “space shuttle quality software.” This experience taught Soleio how company culture gets set early and is deeply influenced by the business model and founders’ personalities.
Following his operational roles, Soleio had great success an angel investor before building Combine, a hybrid venture firm and design studio. However, the “Happy Meal” approach of bundling investment and services proved too complex, creating role confusion when advising founders. He ultimately returned to angel investing, finding it provided more authenticity and freedom to give direct advice without the constraints of managing outside capital. His investments include Figma, Vanta, Vercel, Replit, Perplexity, and many more.
The parts of this conversation I find myself continuing to reflect on are just how formative company cultures are and how often that's taken for granted by otherwise overwhelmed entrepreneurs. In our first post about indie we wrote:
Like cement, the cultural foundation for new projects and companies sets early. Those who focus on raising outside capital and achieving fundable milestones have a very difficult time getting off that VC treadmill.Those who focus on creating value for customers and generating positive cash flow from the very beginning are able to make their own decisions independent of competing outside interests.
This is true of fundraising, product, and execution. As Soleio says so eloquently in this conversation - Culture is the deepest moat one can create.
The "culture of Soleio” seems to contain a bunch of contradictions — care for craft with an obsession for speed. A clearly massive ambition coupled with a desire to be a “trim boat” that can be lean and focused.
With Soleio, you can’t spell culture without CULT, and in this conversation, he mentions a piece of writing that had a profound impact on him that we would be remiss not to share here:
The Cult of Done Manifesto by Bre Petis and Kio Starks
There are three states of being. Not knowing, action and completion.
Accept that everything is a draft. It helps to get it done.
There is no editing stage.
Pretending you know what you're doing is almost the same as knowing what you are doing, so just accept that you know what you're doing even if you don't and do it.
Banish procrastination. If you wait more than a week to get an idea done, abandon it.
The point of being done is not to finish but to get other things done.
Once you're done you can throw it away.
Laugh at perfection. It's boring and keeps you from being done.
People without dirty hands are wrong. Doing something makes you right.
Failure counts as done. So do mistakes.
Destruction is a variant of done.
If you have an idea and publish it on the internet, that counts as a ghost of done.
Done is the engine of more.
You may be piecing together a theme here that I hope comes through loud and clear here.Accelerating your time to done is the ultimate informant for what’s next. If you can master that loop, you’re well on your way to having the impact in life and culture that you aspire to.
This conversation with Soleio is a good reminder of that, and I hope you enjoy listening as much as we enjoyed recording it.
Happy New Year!
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Throughout the first year of indie’s return, I’ve felt a real sense of tension.
That tension sat at the intersection of what indie was and what indie wants to be.
In its earliest days, indie was often framed as an anti-VC, profit maxi path. Rigid in its philosophy and dogmatic in its practices. This positioning served as a counterbalance to the investor-focused narratives at the time of "always be raising" and building towards the next fundable milestone.
We had a point to make, but the point was often overshadowed by an undercurrent of disenfranchisement from various corners of founderdom.
So what was the point?
In 2017 we wrote:
We want to enable a world where founders don’t need permission from an increasingly small group of fickle funders to exist. We want to see companies thrive that live more than 30 min from Sand Hill Rd. or San Franciso. We want to see entrepreneurs who don’t look like, talk like, think like, or see the world like they do achieve their full potential. We want a world that isn’t simply trying to get in front of the product road maps of Google, Facebook, Amazon, or Microsoft.There’s a wild, weird, and wonderful world of opportunity that will go unrealized if we continue running the current VC-backed startup playbook of asking permission to exist every 12–18 months.
In 2018 we wrote:
The Basecamp way is NOT to never raise money or dogmatically bootstrap a pure and independent business even if it means putting your, or your family’s, financial well-being at risk. No, the Basecamp way is to put yourself in a position that should you choose raising money is in your best interest that it can be done on your terms and on your timeline and embody your own definition of success. And, far more founders should follow it.In 2019 we wrote:
“We’re not anti-V.C.,” said Akshay Kothari, the Notion's chief operating officer. “We’re just thinking for ourselves, rather than for them or other peers.” The rules of engagement around investment are changing as quickly as the dollars are shifting to various stages for deployment. Retained ownership and optionality are slowly replacing amounts raised and artificial valuations as the ultimate signal of ambition. If you’re an investor or entrepreneur not taking notice of these changes you’ll be left flat-footed in the months and years to come.Hopefully, you’re starting to see a pattern.
Historically, we anchored on fundraising to tell that story. But I think we’ve hit the expiration date for that.
Indie was never about fundraising. It was, and is, about independence. Not having to rely on outside funding just to exist is one way to do that. Not having to ask anyone for permission to build the thing you can't not build is another. But I'm excited to start telling other dimensions of what this "indie era" has in store.
As I’ve been telling the indie story this year I’ve continued to feel the tension between the old indie and the path ahead. Trying to square what people wanted indie to be and what it wants to become.
As a final send-off to the old indie, we recorded a little video capturing some of the ups, downs, and a hahs of the journey so far. It was surprisingly cathartic to recount the indie lore and felt like a proper end to the new indie’s first year.
2024 was an incredible year for indie generally and for me personally. I can’t thank all of you enough.
— Bryce
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Once upon a time, when MTV played music videos, their more mature sister channel, VH1, had a show called “Where Are They Now”. The idea behind the show was to track down notable artists of previous generations to see where life had taken them once they’d stepped out of the spotlight.
OK boomer, what does this have to do with the indieverse specifically, and the culture of technology more broadly?
In most creative fields, whether it's art, fashion, architecture, etc., there's a deeply held sense of respect, even reverence, for the innovators who came before. The breadcrumbs of insights and artifacts or creation serve as a foundation of reference points for those who come after.
But tech, as a creative field, feels different. Always forward, never back. There's frequently disregard, even contempt, for the innovators who came before.
I often say we have the raw materials for any number of possible futures. Breakthroughs in AI, energy, chip design, crypto, biology — the future has never been brighter. As excited as I am to charge forward, I thought it would be valuable to look back.
When I entered the venture market, it was in the wake of the dot com crash. Shortly after, my partner, Tim, popularized the term Web 2.0. Then, as now, there was a deep sense of hope starting to swell in technology. There were lessons to draw from and infrastructure to leverage to build upon, in addition to a renewed sense of optimism for the role technology could play in our lives.
As we enter a similar moment in tech, I wanted to return to some of the innovators of Web 2.0 to see if there were any lessons to glean from their experiences, and to celebrate their contributions to the progress we're building on now.
The first of these came up in our conversation with Charles from Are.na earlier this year. He and his team and had drawn inspiration from a popular Web 2.0 called Del.icio.us, known primarily as a shared, social website bookmarking service. I have known and respected its founder, Joshua Shacter, for years. We decided to trek to Mountain View for a catchup with Joshua on his past learnings and current projects.
Joshua built Del.icio.us as a side project while working at Morgan Stanley, evolving it from his earlier project called Meme Pool. He didn’t set out to build a startup - it was simply a tool to manage his own bookmarks that grew organically to millions of users. Within less than a year of raising funding from Fred Wilson at USV, Del.icio.us was acquired by Yahoo, where Joshua experienced the challenges of corporate bureaucracy and struggled with the loss of control over his product.
The Web 2.0 era allowed for more experimental approaches, whereas today’s entrepreneurs are highly focused on specific business opportunities, particularly in areas like AI tooling for business functions. Joshua believes that the current AI revolution has reset computing to a pre-6502 type era where fundamental architectures are still being determined, making it an exciting and challenging time for founders who need to balance innovation with market demands.
When investing, Joshua looks for founders who are perpetually unhappy with their tools and constantly seeking improvement. He prefers to invest in weird ideas that make him think, “I never would have thought of that”, rather than incremental improvements to existing solutions. His approach is fundamentally engineering-driven, and he values founders who can engage in deep technical discussions.
This one was a ton of fun. It's a new format for us, so be gentle with the feedback. We’ve already learned so much and hope to improve on it. We have a few more of these in the can and a few more lined up for the new year. If there’s someone you’d love to see us catch up with, shoot us a reply with suggestions.
As always, if you or someone you know are working on something that could be a fit for the indieverse, we’re always on the hunt for our next investment.
Finally, from all of us to all of you, wishing you the happiest of holiday seasons.
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There’s a section of our website that generates more reaction than any single piece of content I’ve ever written. It says:
We’re obsessed with the idea that someone is going to build a business doing $100M in revenue with less than 10 employees and see it as this generation of founders’ 4 min mile. Once someone shows it can be done, many more will follow. We want to partner with the one that does to help define a repeatable playbook for those that follow.
Whether the numbers are correct or simply guide posts, it’s undeniable that how and what we build in a post-AI world is changing by the day. (Maybe hour?) This theme has been a clear focus for our investing at indie and has shown up in the form of AI infrastructure, AI services, and new work modalities enabled by AI.
This week, we sit down with a founder at the vanguard of post-AI entrepreneurship — Rahul Sonwalkar of Julius AI. One thing I was struck by in this conversation is not only the efficiency and speed that new AI tools unlock, but the ability to embed more of the humanity of the founders into the businesses they are building as both a competitive moat and differentiator. Rahul is the embodiment of this in ways that will become clear in the video.
The story of Julius begins after six pivots and countless experiments. Rahul and his team built Julius.AI by embracing a hacker mentality and following their instincts rather than conventional startup wisdom. Instead of building a massive sales organization or chasing traditional metrics, they focused on product-led growth and let users discover the value naturally. Today, Julius processes over two million lines of AI-generated code daily, helping knowledge workers analyze data without needing to code or relying on data analysts for their insights.
The funding landscape has shifted dramatically with AI-native startups. These companies can operate much more efficiently than their predecessors, giving them more optionality around fundraising. Rather than raising capital at predetermined milestones, Rahul has taken a more opportunistic approach, something we call “macrodosing capital”, raising smaller amounts when offered and focusing on infrastructure investments that will pay dividends long-term.
Looking ahead, Rahul believes the key to building in the AI-era is positioning your company to benefit from, not be threatened by, improving technology. While giants like ChatGPT attempt to replicate features, Julius has found that the large player’s marketing efforts actually educates the market and drives users to more specialized solutions. Rahul aims to go public eventually, seeing a massive opportunity in making AI-powered products accessible to everyone — not just developers.
This is a must watch for anyone curious about how AI is reshaping entrepreneurship and the opportunities it presents.
That said, if you’re looking for actionable insights or a playbook here, you may find yourself frustrated. This is an emerging field where the landscape is shifting underneath us. Any tools or tactics mentioned here could be obsolete by the time you finish watching. The core ideas of being true to your instincts, staying lean, doing more with less, and delivering value for customer feel even more timeless in the context of this conversation.
I hope you enjoy watching as much as we enjoyed making it. And if you do, please share widely. Like and subscribe. All that jazz.
And, as always, if you're working on anything in these areas that could be a fit for an investment from indie, don’t hesitate to reach out.
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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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