Terminal NYC with Reggie James

9 snips

Jan 23, 2025

Bryce Roberts, a leading venture capitalist from OATV known for his indie investment thesis, joins Reggie James, tech innovator and coiner of 'indie-pilled'. Together, they dive into the current dynamics of venture capital, highlighting the shift from rapid returns to sustainable growth. They discuss the importance of cash flow and customer needs, the evolution of seed funding, and the impact of AI and cryptocurrency. With humor and personal stories, they explore challenges in startup culture and the philosophy of ephemeral entrepreneurship, advocating for mindful, independent business practices.

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ANECDOTE

Bryce's Early Career

Bryce Roberts got into tech through a Y2K SAP implementation project.
His first entrepreneurial venture was a custom ski maker, which failed.

INSIGHT

Smaller Exits and Venture

Smaller exits, like Flickr and Delicious, had a market, but VCs couldn't profit from them.
Smaller funds, however, could generate venture returns from these acquisitions.

ANECDOTE

The Shift in Seed Investing

Seed investing initially offered optionality: raise more, become profitable, or sell early.
Seed investing quickly evolved into an arbitrage opportunity: raise a small amount, improve the company's image, and then sell quickly at a high markup.

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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.