Main St. Summit Q&A + Request for Startup Confessionals
Last week, I had the opportunity to return to Columbia, MO to participate in the Main Street Summit, hosted by my friends at Permanent Equity. Last year, I kicked off the event with a talk from the main stage that I titled The Indie Era of Startups. That take was so well received, I think it surprised all of us — including me. A highlight of the event this year was the number of people who ran up to me quoting lines and stats from the presentation. If you haven’t read it, you can revisit it here.
I think I got some things really right and some things kind of right that will be more pronounced in the coming 18 months. It was fun to see what stuck with people and what we could still debate this year. I absolutely love this stuff.
This year, we kept it simple with me moderating a panel and doing a live Q&A session in an area they called The Trenches.
We had our gear in tow, so we decided to record The Trenches session, which we edited down to just under 20 min. The questions we covered included:
— The indie backstory
— When does it make sense to lose money?
— What’s venture going to look like over the coming years?
— What stage and type of company does indie invest in?
— How does indie think about liquidity and timelines?
These were all off the cuff and unscripted, so there are holes I would love to fill in and nuance I’d add with more time and consideration. But people seemed to enjoy the session, and we wrapped with more hands in the air than than we had time to call on, which I take as a good sign.
I hope it sheds some light on how our thinking at indie is evolving, and if it prompts any questions of your own, don’t hesitate to reach out — I’ll try to answer as many as I can in future videos.
Speaking of content…
A few weeks ago while speaking at an event in Austin, I had someone come up to me afterwards and confess: “I’ve literally made every mistake you just warned us about”.
To be fair, this happens to me all the time, but this one was a bit different. The founder in question had previously founded a very large public company that I guarantee most of you have used at one point or another. For their second act, they had decided to raise a nine-figure seed round, and proceeded to build like the ZIRP era would never end. This person is a phenomenal operator, and they will be fine, but we had a probing and rich conversation about how those mistakes were impacting how he has to capitalize and build the business going forward. Which got me thinking…
I’ve had *so many* of these conversations over the years, that I jokingly call them “Startup Confessionals”. These are really open and candid conversations with current and former founders about indie-related mistakes they’ve made that they’d like to avoid in the future or sticky situations they’re in right now that they want and need help thinking through.
Often, these people feel alone. Like they’re the first to find themselves in these situations. In startups, we tend to generalize and celebrate success, and avoid sharing lessons from avoidable failures and mistakes. Maybe that’s partly why the Founder Mode essay resonated so much? It got me thinking about a way for us to capture some of these startup confessionals to share these learned lessons and lived experiences more broadly.
REQUEST
We’d like to experiment with telling these stories.
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 members
There’s a lot of these out there that I think would be valuable for other founders to hear and learn from. I think we have a setup to share them in a way that is respectful to the experience and discrete with the sharers identity.
It’s worth noting that my intent with this isn’t to dunk on or expose anyone. My intent here is informed by a deep love and respect for entrepreneurship and startup culture. I want to see more founders succeed, and my hope is that sharing these stories will help many to avoid the traps others before them have tripped.
Startup Confessionals can be submitted: HERE
And, 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
