How three PearX S19 alums raised $50M this quarter
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Today, raising capital is far more challenging than it was a few years ago. There are no fake Series A’s— most businesses require a good foundation, strong unit economics and growth as well as a moat to get there. We talked to three alums from our 2019 PearX cohort to hear how they raised capital this year: Andrew Powell from Learn to Win, John Dean from Windborne, and Parth Shah from Polimorphic.
PearX is our exclusive, small batch, 14 week program. 90% of our companies go on to raise a successful seed round from top tier investors. PearX alumni companies include Affinity (S14), Viz.ai (S16), Cardless (S19), Federato (S20), Valar Labs (S21), and more.
Answers have been edited for brevity.
Learn to Win (PearX S19):
Learn to Win is a training platform that empowers companies to design, deliver and assess the impact of employee training. They serve customers across commercial and government markets in primarily high-intensity training situations. Learn to Win closed a $30M Series A round in June 2024, led by the Westly Group and joined by Pear and Norwest Venture Partners.
Windborne Systems (PearX S19):
Windborne is a full-stack, vertically-integrated weather intelligence company. They operate the largest balloon constellation on the planet, running a base weather forecast with the data they collect from those balloons. Windborne raised a $15M Series A round, led by Khosla Ventures and joined by existing investors Footwork VC, Pear VC, and Convective Capital.
Polimorphic (PearX S19):
Polimorphic digitizes government operations, helping governments provide a great customer service experience to their residents and businesses. AI-powered search and voice software empowers municipal employees with saved time and resources, while delivering a modern service experience that delights residents. Polimorphic raised a $5.6M round, led by M13 with participation from existing investors Shine Capital and Pear VC.
It’s been five years since you went through PearX. What did you learn from this accelerator program that still provides you value today?
Windborne: Mar played a big role in us even founding a company. Our very first check came from Pear Dorm. Fundamentally, we learned how to be entrepreneurs, and every connection in those early days came through Pear.
Polimorphic: One of the most interesting pieces of it was thinking about how venture-scale businesses are different. When we came into PearX, we didn’t even have a company yet, and we hadn’t even landed on this iteration of Polimorphic.
It takes time to find product market fit. PearX supported us during the exploration phase— you need to be nimble, trying stuff until you find what clicks. COVID interfered with a lot of our plans to work with the government in the early days, and recently we’ve really found product market fit.
Where has Pear helped your company the most?
Learn to Win: Hiring and fundraising. Pear has helped hire our first few engineers and our first few executives.
Windborne: Especially in the last year and a half, Pear’s talent team has been insanely helpful with hiring. Beyond that, they offer general advice on people ops: compensation, policies, equity splits— everything around managing people. We use Ashby for free through Pear. It’s very convenient to have a VC you trust a lot to help you get set up with these things.
One of the single biggest challenges that all companies face is talent. If you’re good at talent, you’ll win. If you’re bad at talent, you’ll lose. To have a VC that stands out in talent is incredibly valuable.
What’s a piece of advice for founders trying to raise a Series A?
Learn to Win: When it comes to Series A, there’s certainly more of an emphasis on metrics and scalability. Talk to other folks in your sector and ask them what key metric they were gunning for, what pieces of evidence they gave to investors to help them understand your business opportunity.
At seed, we proved we could build a great product and deliver great value for customers. What needs to change is an engine that can repeatedly do that at scale.
Windborne: My biggest piece of advice is to be wary of advice that isn’t relevant to you. Think about where you want advice and where you don’t. For us, we disregard a lot of things people tell us when it comes to engineering and manufacturing when they don’t understand the way we run our business. You’re not going to win by only following commercial industry wisdom.
As the rounds progress, things definitely get harder— riskier, scarier, more challenging. But they also get so much more fun.
What sets Pear apart from other venture firms?
Polimorphic: Pear’s willingness to be involved. We were pre-idea, pre-company when we met Pear; we just knew we were interested in the political realm. Pear stuck with us as we started to explore government. Their ethos of investing in people manifested in sticking with us through a few different iterations.
Learn to Win: Pear is an expert at early stage— even what comes before it. We were still students at Stanford working out of our dorm room, and Pejman and Mar were some of the first people to believe in the potential of our business. In the early days, there’s so many people that could point out a million reasons why your startup will fail. Pear believed in the one reason out of a million and helped us understand how to dig into it.
What are your goals for the next phase of your company?
Learn to Win: We’re trying to ramp up our defense business and grow aggressively across the board. We’re just scratching the surface, and we’re excited to see what we can do with this new capital.
Windborne: We want to scale up data collection operations. We’re launching around 100 balloons a month, and we want to be doing a few hundred a month. By the next round, we want to be doing over 10 million a year in revenue. And more importantly, we want to be collecting more in situ weather observations than the rest of the world combined.
Polimorphic: We’re on path to having 100 government clients, which is a big milestone. We started with cities and counties and are about to do our first state-level deal. That’s the next big phase: acquiring more customers, delivering a new paradigm for governments to provide customer service to their residents.
All three of these companies were in the same PearX S19 cohort. At the time, these startups were all just a few founders and an idea. It’s amazing to see their growth and to see them collectively raise $50M+ over the last quarter. Read more about PearX here. Applications for PearX W25 open on August 20th.