


Season 16 of The Pitch focuses on “cool stuff” startups (consumer brands, hardware for accessibility, and deep tech) rather than middleware/AI wrappers. It highlights founders pitching to VCs in Tampa, plus deal-making and investing that happens outside the pitch room, including founders investing in each other and community growth via The Pitch Fund 2.
The transcript doesn’t name specific guests; it references Lisa (host/producer), “new VCs” (including mention of Draper wanting to invest $1M), and founders such as Natalia. It also mentions “18 founders and 10 VCs.”
Entrepreneurship balances hubris and humility; the pitch room drives investments, but relationships and group chats also lead to commitments.
8 Sleep for daytime; hardware to help blind people see; weather-changing tech aiming to make rain/snow on demand; “dairy” as a life journey.
Written by AI. May contain mistakes.
Discover the diverse range of innovative startups featured this season.
“What if you wanted to not make it rain somewhere else?”
Understand the evolution of the pitch events into a broader community and investment opportunities.
“when we bought our show back from Spotify and then started a venture fund to let listeners invest.”

Get the gist, explore an idea or ask about something said.
On The Pitch, what are the key points of this episode?
Automatic transcript. May contain errors.
0:00Welcome to a brand new season of The Pitch. It's our sweet 16. We're going to prom. This season, we ventured to Tampa. 18 founders and 10 VCs flew in just to swim with the manatees. JK, it was to hang out with me and Lisa. This season, we're giving you more of what you love and less of what you don't. I definitely start to blank out when we're talking about middleware AI wrappers. Software is out. Actual cool stuff is in. We've got consumer brands. We're building 8 Sleep for daytime. Hardware that helps blind people see. They kept asking for middle finger. Next thing we knew, we had like 10 students running around flipping each other off.
0:41We've got deep tech to change the weather. Our big vision is to make it rain and snow on demand. What if you wanted to not make it rain somewhere else? Like one day we're just like, screw Arizona. And of course, dairy. I never imagined my life journey would be milk. But it isn't just the founders giving us what we want. We've got some new VCs, and they were born for the pitch room. Entrepreneurship is the dance between hubris and humility. We were deep in the cut for three hours. My brain just, like, lit up. And all your old favorites are in the room, too, doing what they do best. I got strings.
1:19I'm not an easy yes. May I ask sort of an A-hole question? I don't think you're raising enough money. What are the weird use cases? The VCs bring out their checkbooks in a big way. I finally answered the FaceTime and he's like, dude, Draper wants to invest a million dollars. And I was just like, wait, what are you talking about? And more founders than ever before will enter the foxhole. Let me ask you a more plain, bold-faced question. Would you ever play a sport where you didn't know where the goal was? No. That's what you're doing. But what surprised me this season is that just as much happened outside the pitch room as did inside.
2:03Have you ever committed to a founder based on a group chat before? I can confidently say I have never. I have never. We even have founders investing in each other. Natalia comes up to me. She's like, hey, do you have a quick second to chat? And just right away, she's like, all right, I really, really want to invest$10 ,000. You know, when we started inviting people to these pitch events, we had no idea. it would grow into something so much bigger than a podcast. I really didn't totally understand what I was getting myself into with this thing. You know, like this is a program, this is a community.
2:36I mean, I guess we kind of knew this would happen when we bought our show back from Spotify and then started a venture fund to let listeners invest. Speaking of, in season 16, we make our first investments out of the Pitch Fund 2. Majority of that is already signed and wired. Who are you waiting on? Well, you know that to put you guys on the spot could you make a signed and wired commitment to the half-wear deal?
3:07We're in, Jack If you want to invest in what you hear this season you can learn more at thepitch.fund Season 16 starts next Wednesday August 19th We will see you wherever you get your podcasts In the pitch room Lisa, I didn't know you were here.
Hardware that helps blind people see. Deeptech that controls the weather. The brightest lamp you've ever seen. And... milk?
The Pitch is back on August 19th.
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