A documentary crew showed up at a portfolio company’s garage. An LP explains why he quadrupled his commitment. And tickets for Tampa are live.

Let's get into it.

Kavitta Ghai walked into The Pitch Room, pitched Nectir (Slack + AI for schools) and walked out with the most money any founder has ever raised on our show $1.4M in 30 minutes. Cyan Banister offered to lead at $1M on the spot.

That was in early 2024. Here's what happened next.

Kavitta went after the entire California Community Colleges system. All 116 schools, 2.1 million students, 40,000 faculty. 

Every VC Kavitta talked to told her not to chase a deal this large. Her own board told her not to chase it. She chased it anyway. And Kavitta offered the entire pilot for free to prove the ROI, staking the future of the company on this one deal.

The pilot started with 50-60 classes across 10-15 schools. By December 2024, 272 faculty had joined across 83 campuses and 8,000+ students were using Nectir AI in the classroom. The results: students in classes with Nectir saw a 13% GPA increase compared to control groups, and 17% more students passed their classes.

Following the successful pilot, the California Community Colleges System signed a multi-year contract with Nectir. It's the largest deployment of AI in education in the United States.

Nectir closed a $12.5M Series A at a $60M valuation, led by Rethink Impact alongside GingerBread Capital, Strada Education Foundation, and existing investors. The Pitch Fund I wrote a $218K follow-on check in the round alongside Long Journey Ventures and Precursor Ventures.

Kavitta told us she learned something from her pitch on our show. She learned how much of a difference it makes when everyone is in the same room together. So she flew to NYC to do her Series A meetings in person. As she put it: “The energy that you can feel, the way that they can see and feel my authenticity, is like, oh sh*t, she really is gonna go do the damn thing.”

One state down, 49 to go.

🎧 Listen to the NEW episode: Nectir Part 2: Chasing the Biggest AI Deal in Education

Jamie-Jin Lewis grew up watching her mother run a childcare program for 30 years. She saw firsthand how broken the tools were. So she built Wiggle Room: mobile-first management software designed for how small daycare providers actually operate, not how enterprise software companies think they should. Jamie-Jin Lewis has 50 paying daycares with zero churn, and she closed out her $1M round after pitching at our live show in NYC.

🎧 Listen to LIVE in NYC: 3 Startups, 3 Investors, 15 Minutes to Invest

Youtuber Will Phillips from Inside Startups spent a full day with the team in San Jose, and the mini-doc is worth your time. You get to see the prototype graveyard, meet the RF engineer who built his own equipment when off-the-shelf couldn't cut it, and watch a real customer use the ring in ways the team never predicted.

 🎧 Listen to episode #117 Lotus Ring: Hardware Hail Mary

A vertical AI platform for jewelry design trained on proprietary data to make sure designs are actually manufacturable. Q1 was their highest customer growth quarter ever and they’re on track for 4x ARR growth in 2026. They’re opening a $2M round. Interested?

Email [email protected] to request the deck.​​​​​​​​​​​​​​​​

April 21st-23rd in Tampa, FL. Three days of live pitch recording, and you're in the room for all of it. 

Chat with Charles Hudson on a break between pitches. Ask Elizabeth Yin about her love of Hippocorns over lunch. Give Josh a hard time with Jesse Middleton. Meet the charming Rohit Gupta. And find out if Mike Ma’s really as intimidating as the 30-day foxhole makes him sound.

The venue is what makes this one different. We found a coworking space that doubles as our recording set, so between tapings you can pull up your laptop and get work done alongside other founders and investors. We've also added a Founder Mixer open to the local Tampa startup community.

Tickets start at $799, our lowest price ever, so now's the time.

If you committed $100K or more in Fund II, you've got a free all-access ticket waiting. Just email Kate at [email protected] and she'll get you sorted.

Everyone else, grab your exclusive LP ticket before they're gone.

By Rich Smith, Author of The Encouragement Economy, LP in Fund I & II

$100,000 is real money.

When Josh and Lisa first mentioned the Fund II minimum, I felt the weight of that number. It's a different commitment than Fund I. So I sat with it for a while, testing my own thinking.

Then I reframed it.

Fund II isn't a $100,000 check you write tomorrow. It's 3-4 capital calls spread over a few years—about $25,000 to $30,000 per year.

Whenever numbers start to feel big, I always break them down into something familiar. 

Fund I was like maxing out a Roth IRA each year for a few years. Fund II is like maxing out a 401k for a few years.

Different scale. Same discipline.

But here's what really made the decision easy: what I learned from Fund I.

I watched founders who were on a mission—the ones building from lived experience—break through in ways that seemed impossible.

I saw human connection drive real results.

I saw calculated risks pay off.

And the community? It opened doors I never knew existed.

Being embedded in this ecosystem didn't just give me access to deals. It changed the trajectory of my life in ways I'm still discovering.

The Pitch isn't just a fund. Josh and Lisa built something different—a system where every investment strengthens the platform, and the platform strengthens every investment. That kind of compounding advantage is rare.

Fund I proved the model works. Fund II is about scaling what works.

When you see that kind of proof? Stepping back isn't an option.

So I committed $100,000.

Not because I had extra capital sitting around. But because when you see that opportunity is expanding right in front of you, you don't hesitate. You accelerate forward.

If you're thinking about Fund II and the number feels big, I get it.

But ask yourself if $25-30k per year over the next few years is an opportunity worth expanding for yourself.

I'll be in Tampa next month at the upcoming recording event. I'd love to hand you a copy of my book The Encouragement Economy personally. Chapter 10 tells the story of why I invested in The Pitch.

See you there.

📖 Get The Encouragement Economy Book on Amazon

Connect with Rich Smith on LinkedIn

Thanks for reading! We held our first close Fund II on January 30th. If you'd like to partner with us, just hit reply. We'll be in SF, Austin, Miami, Tampa and NYC this year, or we can hop on a Zoom anytime.

The best is yet to come,

Josh & Lisa