It started with a simple question. What if people could hear what actually happens in a pitch meeting?

Fifteen seasons later, that question has turned into something bigger. The Pitch isn't just a show, it's a community of founders who've been in the room, investors who've made the bet, and listeners who've watched ideas become companies.

This season, we're bringing you more pitches, more live events, and a big update on a listener-favorite company featured in season 11. Plus, we’re continuing to back the companies you hear on the show through The Pitch Fund.

This is where conviction meets capital. This is Season 15.

This Week’s Episode: Your AI Website Sucks. PeachWeb is the Future

In the 1980s, a Dutch shoe shop owner put a baby lion in his store.
People lined up. They talked. They bought shoes.

Four decades later, his grandson Lucas pitched PeachWeb — a 3D website builder — to four VCs. No cart. No checkout. No payments roadmap. No hedging.

Just one thing: unforgettable marketing sites. His baby lion.

The VCs loved it.  But is it lovable enough?

#176: Your AI Website Sucks. PeachWeb is the Future

The Pitch Tampa!

April 21-23. Sunny Tampa, FL. Three days of live pitch filming, real conversations, and the kind of community you can only build in person.

We're bringing together the investors, founders, and listeners who make this show what it is. If you've ever wanted to see what actually happens behind the scenes—or if you just want to spend three days with exceptional people who are building the future—this is it.

This event is for:

• Investors looking to meet their next portfolio company

• Listeners of the show who want the IRL experience

• Anyone who wants behind-the-scenes access to how deals actually get made

You'll watch live pitch filming, connect with brilliant builders and investors, eat incredibly well (it's Tampa, after all), and be part of the community that's shaping the next wave of startups.

Save your spot, tickets are live now!

Founders: Want to pitch on the show? Apply here.

Fund I Reflections As We Raise Fund II

From Josh & Lisa

An LP recently asked me, "What is your biggest learning from Fund I?" I sat there struggling for an answer for a solid 10 seconds. Fund I provided a breadth of learning opportunities. The struggle was narrowing it down to a simple takeaway.

In the moment, I talked about founder conviction and how the only investments we "regret" so far are those made into founders who didn't have a deep, life's passion for the problem they were solving. 

VCs often talk about investing in the crazy, the weird, the obsessed. And we're doubling down on the crazies in Fund II. In a game of outliers like venture, the people can be just as much of an outlier as the business itself.

But after that call I couldn't stop thinking about all the things we've learned in Fund I. I wish I could boil it down to one theme, but I think it's really just a bunch of tiny learnings that over time build into a better decision making machine for the fund.

Lisa and I both took time to write out a few learnings from Fund I. Perhaps a theme will emerge in time!

Josh's Learnings:

1. Now that product differentiation isn't a moat anymore, speed is everything. But investor capital probably won't unlock execution speed. If the team was executing slowly at pre-seed they're likely to continue slowly after raising seed.

2. Horizontal SaaS tools are dead, go vertical instead. Horizontal tools are now a winner-take-all game reserved only for the most well funded. Unless you've got the likes of Andreessen on the cap table, go deep instead. Find a customer no-one else is building for and replace their entire software stack.

Lisa's Learnings:

3. Follow your instincts. There were founders we spoke to that gave me red flags. But I followed "smarter" voices assuming they saw something I didn't. In hindsight it's clear, I saw things they didn't see.

4. There is no substitute for meeting IRL. Meeting a founder in person gives an abundance of character context. Each Pitch Event we have added more and more time with founders. Time = relationships. The more time spent, the more we get to know a founder and understand what drives them.

5. Consumer is a sweet spot for The Pitch. I believe we see an outsized number of deals in this area (because podcast = distribution) and, therefore, get to choose the cream of the crop. We’ve really strengthened our thesis here. In an era where companies are staying private longer, how do we return capital faster? Consumer gives us that potential, since winners are often crowned in shorter 5-7 year cycles.

6. We’re playing a different game. There are a lot of VCs out there and we can’t compare ourselves to them. We are non-traditional VCs, and that is not a weakness. It’s what gives us an edge.

Cheers,
Josh & Lisa