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Ramping up PnR with Cofounder Kevin Weatherman
SXSW to #NYTechWeek, new swag, upcoming races!
Dorothy Chau, Kat O’Brien & Kevin Weatherman
March 11, 2025
It’s no secret that Pitch and Run has grown 10x in the past year. The community is stronger than ever as it navigates new boroughs, states and now countries 🇬🇧 ! This growth didn’t happen overnight. We finally got to sit down with Kevin Weatherman, one of Pitch and Run’s cofounders, to get a glimpse into where PnR started. Not only is Kevin an avid runner, he’s an entrepreneur and angel investor with a track record of scaling startups from early stages to significant revenue growth. He was the first business executive at MoPub (acquired by Twitter), OneSignal, and PubMatic, helping grow MoPub from $0 to $250M+. As VP of Enterprise at Moloco, he contributed to the company’s rise as the #1 mobile app DSP, valued at $1.5B. An active investor in NYC, he has backed B2B SaaS companies like Attentive, Electric AI, and mParticle, leveraging his expertise in mobile, ad tech, and business development.
One of the first runners for the NYC marathon 2024! 💫
Q&A Interview with Kevin Weatherman, Cofounder of Pitch n Run
Dorothy: Can you tell us how you got into the startup ecosystem?
Kevin:I took a call from Google, and they asked what it would cost to transport all their employees to work every day. I helped sign the Google shuttle contract for Bowers Limousine in San Francisco. At the time, I asked my best friend from high school, who was working at a bank, “What does Google sell?” He told me they sell ads. That day, I started looking for startup ad companies in the Bay Area, got into ad tech, and I’ve been in the startup ecosystem ever since.
Dorothy: Where did you grow up?
Kevin: I grew up in Brisbane, South San Francisco, went to high school in San Diego, then attended Berkeley for college. After that, I stayed in the Bay Area for five more years before moving to New York City.
Dorothy: What was your first official introduction to startup life?
Kevin: My first intro was when I interviewed at AdBrite and got a job. Two things happened there: first, they gave me stock options, so I had to learn what those were and why employees receive them.
Then, a couple of months later, the founder of AdBrite, Philip Kaplan, explained in an all-hands meeting how they built their ad technology out of necessity, started making money, and eventually talked to angel investors. He mentioned that investors wanted to give him $200,000 for 5% of the company to get it off the ground.
I remember thinking, “What are angel investors?” That sparked my interest in how startups get funded and operate. I ended up at AdBrite because they had just raised $12 million from a major VC, and I had been reading TechCrunch while job searching. That led me to PubMatic, a publicly traded ad tech company, where one of my clients, Fandango, told me that 70% of tickets for Twilight were sold via their iOS app. This was 2010, and from that moment, I knew I had to work in mobile. Since then, I’ve worked at companies like MoPub, OneSignal, and Moloco—all heavily focused on mobile.
Dorothy: At what stage did you join those companies?
Kevin: I was employee #15 at AdBrite. At PubMatic, I was the second U.S. hire; they had a six- or seven-person engineering team in India. At MoPub, I was the first business hire and the fifth overall employee. At OneSignal, I was the seventh hire.
Dorothy: The startup industry has evolved a lot. You mentioned earlier that you didn’t even know what an angel investor was. Many people feel like the barrier to entry is steep because of all the industry jargon. How did you educate yourself?
Kevin: Mostly by talking to people—especially investors. A key moment for me was after we did a secondary at MoPub. That was the first time I paid off my student loans, my bank account wasn’t negative, and I could contribute to my 401(k). It was also the moment I realized I could become an angel investor.
I looked up the qualifications—you either need $1 million in assets (excluding your home) or have earned $200,000 annually for the past three years. That made me an accredited investor. This law dates back to the 1930s to protect people from bad investments, originally aimed at things like fake railroad companies.
Once I qualified, I started researching, talking to other angel investors, and eventually made my second angel investment through AngelList in 2014. I got excited and joined around 200 syndicates, allowing me to see a wide range of deals. Over time, I’ve done anywhere from one to ten investments per year and refined my focus to investing at the idea stage—before there’s even a pitch deck. At that stage, the main thing I’m betting on is whether the founder can break through obstacles to raise money and attract great people to their team.
Dorothy: You’re investing in the founder. But fundraising and building a team are often opposing skill sets.
Kevin: Yes, and sometimes different founders take on different roles. Often, one founder—usually a business or product person—focuses on fundraising, while a technical co-founder builds the early team.
When I meet founders, I always ask, “What’s your secret?” A great founder has an edge—whether it’s a unique way to acquire customers, a strong industry network, or a distribution advantage. That secret gives them a competitive advantage.
The most successful companies I’ve invested in have what I call a “10x founder”—someone who can fundraise, build a team, set a vision, and execute. Those founders are rare.
Dorothy: What’s your secret?
Kevin: Community. Everywhere I’ve gone, I’ve built communities. Pitch and Run is just one example. I’ve tried others, like Intangible Angel, an angel investing community that didn’t really take off.
Pitch and Run started when Nihal texted me on a Thursday night asking if I wanted to run the next morning. Oleg joined, and soon, the three of us were running every Friday. Then, we started tweeting about it, and it grew.
Now, we have Pitch and Run in New York, San Francisco, LA, Chicago, Denver, Austin, and London. The key to a successful chapter is consistency—showing up at least six months straight. Over time, it has become one of the most meaningful things in my life.
Dorothy: You run six days a week now?
Kevin: Yeah. We have runs on:
Monday in Chelsea
Tuesday in Prospect Park at 7:30 a.m.
Wednesday in Williamsburg (7:30 a.m.) and Central Park (8:00 a.m.)
Thursday in Tribeca
Friday at Chelsea Piers—the original run
Dorothy: And you’ve found people to anchor each of these runs consistently?
Kevin: Yes. It works best if there’s an investor involved. For example, both Nihal and I are active investors, and I know for certain that deals have come out of Pitch and Run. Founders have raised money through introductions made there.
It’s not just a catchy name—we actually do invest.
Dorothy: And it’s been a slow build over time.
Kevin: Yes. For the first three years, we were lucky to get five to ten people on Fridays—maybe 15 in the summer. But Tech Week in New York, organized by Andreessen Horowitz, changed everything.
Three years ago, at Tech Week, we had over 50 people show up. Last year, we had 167.
Dorothy: That’s when it really blew up.
Kevin: Yeah, according to Google Photos, 167 unique faces were in our group photo that day.
#NYTechWeek 2024
How many faces can you count?
Dorothy: Wow. Tell us about your latest deal.
Kevin: Can’t say much yet—it’s in stealth mode. But stay tuned for an announcement in April.
Dorothy: Okay, last question. You’ve probably heard hundreds of pitches. What makes a founder stand out?
Kevin: I always look for their “secret.” A startup is really hard, and founders who have a unique advantage are more likely to succeed.
The other thing is execution. If a founder says they’ll go from $0 to $1.5 million in six months, do I believe them? That’s why some investors delay making commitments—to see if the founder follows through.
Ideas are great, but execution is everything. Fun fact—I bought Text For A Taxi.com in 2008. Basically, the idea for Uber. But I didn’t execute. Execution separates great founders from the rest.
Dorothy: Thank you for this interview—it’s been long awaited!
Kevin: Thank you! And if you want to join Pitch and Run, come to Chelsea Piers on Fridays at 9 a.m. Or, if you want to start a chapter in your city, reach out!
Contact me instagram.com/kevinrunsnyc https://x.com/kevinrunsnyc https://www.linkedin.com/in/kevinweatherman/
Congratulations to all the finishers of Tokyo ‘25! 🇯🇵
🇯🇵 2025
🇯🇵 2025
Kick off this spring with new Pitch and Run socks! Orders end March 31st!
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