INDIE AUDIO

I had never met Anjan Katta before entering his apartment a few months back.  It was some combination of office, shrine, and looney bin plucked from the Charlie Conspiracy episode of Always Sunny in Philadelphia. Despite the absolute chaos surrounding us, the vibe was calm and the energy was high. Clearly this was a founder who had seen some things and had returned to share the lessons gathered th...

Miss us? Feels like it's been a few weeks since we’ve had something new to share. This week, we’re excited to share a video we recorded just before the release of First of Kind.  Grant Lee fits the profile of a founder indie is built to support: worked in investment banking, and joined a hot YC startup that didn’t end up being the rocket ship they’d planned. Joined another venture-backed startup t...

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...

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...

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 t...

"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 th...

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...

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 financia...

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...

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 D...

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...

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-f...

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...

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...

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?...

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...

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 ho...

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 wer...

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...

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 yea...

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 s...

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,...

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...

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 w...