Sol Lipman and PieFi on the Inspiring Founders Podcast
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For one of the very first episodes of the podcast, Mash headed to downtown Santa Cruz to meet Sol Lipman, a serial entrepreneur who owns Pleasure Pizza and started PieFi in the room behind the shop. Every year Sol mentors UC Santa Cruz students building products, and this year the products looked different: in market, cheap to build, marketed in public. So Sol made a space for them, ran a summer program with 10 teams building 10 products, and started asking whether the old path — idea, pitch deck, raise, build — still makes sense.
This conversation has been edited and condensed.
“Doing startups is like an art”
Introduce yourself. Who are you, and why are you interesting?
I don’t know about why I’m interesting, but I’m Sol, and I’m a serial entrepreneur. I live in Santa Cruz, California. I’ve started many, many startups, some of which have been awesome and some of which have been horrific failures. But I always like to make things and create things. So for me, doing startups is like an art. I love it.
When we met, you were pitching the idea of PieFi. You’d just bought the pizza shop downtown, there was this little room behind it, and you had a vision of creating a kind of private incubator space to help startups. You had a lot of energy telling us about it. What was the genesis?
Every year I mentor UC Santa Cruz students who are building products, and in the last year I’ve seen a real shift in the level of product being built, as well as the kind of entrepreneur building it. The trend was really visible during the Launchpad competition at UC Santa Cruz. We used to have a couple of legitimate companies, or potential companies, come out of that. This time it felt like there were products in market. The things the students were excited about were really different. How they approached marketing seemed really different. I was just really energized.
Our family bought the pizza shop downtown — Pleasure Pizza, best pizza in Santa Cruz — and I started to host events. It became a really cool experience where all of a sudden I was interacting with students with five different products in the market. Then this space became available. It used to be an antique store. We took it over, demoed part of it, painted it, put some of our old furniture in it, and we’ve got a literally eight-person foosball table, which is sick.
Also, having done so many startups and never landing a real career means I’ve seen a lot. It’s easier for me to help students because I’ve done so many things, for better or for worse.
“Just build a product”
I hear that a lot from serial entrepreneurs: the accelerators, the incubators, the university programs are so focused on the academia of it — the lecturing, “let us tell you what to do and how to do it.” And what you’re saying is that’s not what people need. It’s the experience, the stories.
When you do a startup, it usually goes: okay, I have an idea, let me validate that idea. Then I’m going to build an MVP, or maybe I need to go raise a little money to build an MVP. And then all of a sudden you’ve done all this work and you’ve hit a roadblock where you have to raise money. And that’s really hard to do. I think that’s changed. Now you can build a product, get it in market, and find out your customer acquisition costs before you even have to raise a dollar.
So it’s the same process, but today you can do it for $1,000 or $2,000 or less, where in the past it was 20 or 200?
That’s the real change. Everything prior to last year made it seem like a pitch deck was the right thing for an entrepreneurial class. The pitch deck brings a lot of things together. You have to think through a lot to make a successful one: What’s my message? What’s my product? What’s the problem I’m solving? What’s the TAM? Where’s the revenue model? All really good stuff.
But now you can really skip the pitch deck and just build a product. In some ways it’s easier to build a product and show it to people than it is to try to convince somebody that it’s a good idea. That’s a huge shift, and it’s going to shift everything. The funding markets are going to shift, because now I don’t need $500,000 from Y Combinator to succeed. I need $5,000 and some really good mentors.
I think we’re witnessing a real revolution, not just in how we use technology to enhance our lives but in how we actually make new products. I think AI is the next small business world. You used to not be able to afford to create an app that’s purpose-built for your local business. Now you can.
I was talking to somebody about the history of software development. Making software was so expensive, and you needed super skills to do it, so companies were created around building generalized software they could sell to a lot of people. As technology got better, you saw the SaaS companies come out building very vertical software. And now, with AI, you don’t have to be a software company or even a specialized developer. You can create the one piece of software you want for your business.
It’s crazy if you think about how fast that’s shifted. To me it means there are going to be millions of product developers where there weren’t before. Lovable is one of the vibe-coding platforms, and they say 100,000 new projects are started every day. A lot of those will be abandoned. A lot of those won’t be companies. But the fact that somebody can have an idea, put a prompt into an input box and come up with an app — that’s pretty crazy.
Ten teams, ten products
Let’s bring this back to PieFi. You were struck, like many of us, that this is an incredible moment, with incredibly creative students coming through the universities — many of them international students, who may have a different mentality about what’s possible, maybe more risk tolerance. You made the space, and then you set the challenge: 10 and 10. How did it work out?
We’re, what, six months into this whole idea of PieFi — not even that, I don’t think. We just did a summer program where we had 10 teams building 10 products. Some of those products were already at varying levels of completeness, so they were at different stages. They were all university students, and we had a couple of entering freshmen as well.
It went pretty well. Some of the projects never flew. There was one we got really excited about, but once we got it into market and started testing it, we realized it didn’t work. Which is another amazing thing about this timeline for us as entrepreneurs: you can build something, decide it didn’t work, and do something else.
If you take half a million dollars of investment, or $10 million, somebody expects you to finish the job. You have to go find product-market fit. That holds back entrepreneurs all the time. Now that won’t happen anymore.
“Now I don’t need $500,000 from Y Combinator to succeed. I need $5,000 and some really good mentors.”
— Sol Lipman · Inspiring Founders Podcast, Ep. 01
“Start building what’s in your heart”
What did you do differently with PieFi from what was already out there?
First of all, the universities in general are amazing, and some of them are very experiential, where you go and you build. But a lot of these ideas are coming out of computer science degrees, where the goal isn’t necessarily to do a startup. The goal is to learn. It’s the academic part of it.
PieFi just says: start building what’s in your heart. Whatever cool idea you have, let’s start building it. There are all these different stages, from the spark stage to knowing your cost of customer acquisition. Wherever you land, we’ll help you get to the next place.
Culturally, things have changed too. People like to build in public now. Marketing is built into the development of a product in a way it didn’t used to be. It used to be that it was going to take you a year, you didn’t want anybody else to do it, and you wanted that aha moment when you finally released your thing. Now it’s “Come be part of this journey, this story,” not “Be the recipient of the news later.” That’s really fascinating to me — building in public, having to market yourself on TikTok or LinkedIn or Twitter or wherever. It’s a totally different world.
So when I look at what’s going on — even when I meet with venture capitalists, or see the things on LinkedIn about “I just raised this” and “I just raised that” — I think this is the long tail of what started with the dot-com boom. All the things you’re seeing in these AI infrastructure companies are really cool, but I think they’ll start to be less interesting. Think about the funding models. The whole goal is to have unicorn companies. I think there’s a new goal, and that’s to build great businesses. Some of those will become unicorns, but some of them will be $100 million run-rate businesses that are badass — jobs and wealth and happiness and great customer experiences.
And some of them don’t even need big venture money. You could build a $100 million ARR business and run it.
That’s why, if you go to the end of the story — these companies become successful in whatever way they become successful — and work backwards, all the infrastructure that exists, from municipalities to universities to institutional investors, angel investors and accelerators, is not made for the future.
I think a model like PieFi is about people coming together, people building. I think a lot about reverse mentoring. The students I’m working with know a lot more than a lot of the people I used to work with at Amazon or Yahoo or AOL. A community space where you’re encouraged to build and help each other and ship things is really what I want to do.
Not a mentor — a connector
I’m interviewing a program manager at an incubator and the director of the SBDC in Silicon Valley tomorrow, and those are the two topics that keep coming up: community and mentorship. It used to be discovery and money and advising. What you’re saying — and I believe it’s true — is build community, put people together, and they’ll figure it out. People are smart, but they want that connection. And mentorship is less about advising or telling than a kind of Socratic dialogue.
You’re right. It’s more about coming together and helping each other out. It’s not even about mentors. One team built a platform that matches college students with local shift jobs — like at the pizza shop. What did they need? A product manager who had built a lot of interfaces, because they had a really cool interface, but it needed work. It needed to pare down features. So I hooked them up with somebody I think is the very best product manager, so she could say, “Okay, guys, these colors don’t make sense here. If you did the onboarding like this, it would be better.”
So your role is less mentor, more connector — someone who can see what they’re missing and fill in the gaps.
The idea of a mentor who can’t really do something for you seems silly to me. If those guys need it, I know people who work at Indeed or Upwork. And if I don’t know those people, they’re one connection away from me, so I can get to them.
That’s what I’ve been doing. We’ve got one team building an AI voice resource for incarcerated people, and they really needed a public defender. So we all started working our networks — not just me; the other students started working their networks too — to find somebody this person could really talk to. It’s collaborative. It’s community. I feel invested in every single thing we’re building, and I think the other students feel invested. We’re all working on a startup together to formalize how we work into a front end that anybody can use.
After the 10 and 10, have you had a chance to debrief with the startups — what happened for you, what did you learn, what can we do differently?
Honestly, we’re not really done yet. We’re going to do an event on November 2nd at the Museum of Art and History. In part it’ll be a demo day, and there will be some other really cool things we’ll announce soon. There will be pizza. Maybe some chicken tenders. They just got back to class last week, so we haven’t really done the postmortem. Our big meeting is tonight, actually, in this room — our first meeting in the clubhouse. So it’s very exciting.
More conversations with founders on the Inspiring Founders Podcast.