Lightspeed’s Justin Overdorff: Empowering NYC’s Next Generation of Fintech Unicorns! (Ryan’s Final Episode)
Listen on Apple | Spotify | Soundcloud
It is with a heavy, heavy heart that I say my farewell to the Wharton Fintech Podcast…I’ll have a proper goodbye section at the bottom of this article.
In my final episode, I sit down with none other than Justin Overdorff, former Stripe exec and now Lightspeed’s newest Fintech partner, based in New York City.
Justin joined Lightspeed after an incredible career spanning Wall Street, growth equity, Techstars, Yelp!, Stripe, a whole lot of angel investing (Lithic, Alloy, Orum, Moov, Stir, Puzzle), and of course…a 2-year stop at Wharton for his MBA. At Lightspeed, Justin is helping lead the team’s Fintech practice and build on its portfolio investments in iconic companies like Affirm and Carta.
As a Fintech junkie with a product-focused passion for tech, Justin understands the true value of innovation and how it can serve as a major impetus for change. Justin’s previous experience at Stripe (which we cover in-depth) stoked his passion for Fintech and the constraints of creative problem-solving in a regulated industry. After hearing his incredible journey, it’s no surprise he’s now helping lead one of the world’s historic investment firms.
Justin was a fantastic final guest, and I’m proud to share the mic with him for the last time. In today’s episode, we discuss:
- His long, winding journey from Wall Street to Wharton to Silicon Valley
- How “exploring” at Wharton during his MBA led him down the tech rabbithole
“My time at Wharton was really formative for me. I didn’t know what I wanted to do right away going into business school. So I spent two years trying to figure out what it is I wanted to do….I started interning at Tech Stars in NYC, with Dave Tisch and Adam Rothenberg…when I graduated, I joined full time, and spent a year and a half working with companies that were at their most formative stage…Working with founders at that stage was incredibly interesting to me. It helped me get a much better perspective of what the entrepreneurial journey looks like.”
- His initial foray into fintech (and a big missed opportunity…)
“I had this kind of long running interest in FinTech, but my interest in it came more from folks that I actually met on Twitter. Folks like Howard Lindzon, who was really looking at FinTech more from the Wall Street angle…At the time, Howard kind of had this community of Twitter folks, Fintwit, if you will, that was really getting interested in fintech...So I started spending time with Howard and I attended a couple of conferences that he had. He has something called Stocktoberfest and then Lindzonpalooza, and I started going to those and meeting people in various places. A funny story is I saw the Robinhood founders pitch to a roomful of maybe 40 people in a bar! I was not smart enough in any way to put any money in that company at the time.”
- His incredible tenure at Stripe, where he launched some of their most prolific products, and also what he believes is the key to Stripe’s long success
- Why he left one of the greatest startups of all time to join Lightspeed
“When word started to spread that I had left, a bunch of firms started reaching out, including Lightspeed, and I spent time getting to know a lot of these partners at many firms. And the thing I kept coming back to with Lightspeed was they had this motto, ‘One Lightspeed.’ And it really means that the firm is above the individual, and everyone wins or loses as a team. The reason that was interesting to me was that venture can be a very lonely business, right? I tend to gravitate more towards team approaches. And a lot of firms say that they’re team oriented. But in spending my time with various firms and partners, there was a lack of consistency in the ways with how people speak about their times at their firms. And for Lightspeed, it was just amazing how consistent every partner, every person that I talked to, talked about One Lightspeed. Every person talked about it being a, ‘we’re going to win as a team, and we’re going to lose this team, your success is my success’ culture. That really resonated with me — it was a super strong signal.”
- Why narrowing your focus is a crucial key to success in venture
- Fintech’s underestimated TAMs
“How we underwrite deals to certain exits, and to what the TAM looks like, in some of these cases, has been misunderstood. Particularly in things like infrastructure, the way an infrastructure play unfolds over the long term is there is certainly an initial use case, but if you’re building great infrastructure like Stripe, what you’re actually doing is you’re enabling new business models. Things that could not be built in the past that are being enabled by great products today. As a result, these TAMs really expand over time.”
- How he’s framing investing in this Raging Bull market and credit cycle
- His prolific angel investing
- A fun rapid-fire round including his fintech heroes and Facebook Libra’s “Leroy Jenkins” moment
And much more!
Listen on Apple | Spotify | Soundcloud
*Some quotes have been lightly edited for clarity.
—
A Brief Farewell
As I mentioned at the start, this will be my final episode with Wharton Fintech as I am long graduated.
Sharing the stories of 200+ of the world’s top fintech builders, investors, and thinkers has been the honor of my professional career. Though I (and definitely my classmates) questioned why I dedicated half of my MBA to record podcasts and write articles in my room, it turned out to be the best decision I’ve ever made.
I’ve made lifelong friends and met inspiring people that have changed my life, while learning so much about this industry. I want to extend a special thanks to previous Wharton Fintech stewards like Peter Jankovsky, Shayaan Khanna, Keane Ehsani, and Wharton Fintech Founders Daniel Macauley / Steve Weiner for paving the way…Miguel Armaza for being my fearless copilot over the last 2 years and always daring to think bigger, to our editor Rafo for doing pristine work on the toughest timelines, to the new hosts for keeping the show going strong, to all of my guests, and to the 130k+ strong Wharton Fintech community.
I’ve since moved to the Bay Area, still working in fintech, and would love to meet some of you. You can reach me on LinkedIn or Twitter.
One thing is for sure, I know this is not my last time behind the mic. I’ll be back…here or elsewhere. Have a wonderful new year and thank you for tuning in to our show.
—
Other Episodes You Might Enjoy:
Billionaire Investor, Activist, & Educator Tim Draper — China, Bitcoin, and Free Societies
Jon Zanoff, Founder of Empire Startups & Stella Ventures — YOLO Fintech and the Get Sh*t Done KPI
Balderton Capital GP & Former GS Partner Rana Yared — Fintech Investing in Europe!
Y Combinator’s Michael Seibel & Dalton Caldwell — Lessons from 5000 Entrepreneurs
Jeff Immelt, Former GE CEO — Globalization, Crisis Leadership, & 16 Years at The Top
Former Vanguard CEO & Chairman Bill McNabb: The Future of Finance, Leading in Crisis, & ESG
Brianne Kimmel, Founder of Worklife Ventures — 6 Unicorns, Solo Capitalists, & the Future of Work!
Michael Sidgmore, Partner at Broadhaven Ventures: Why Alts Are Going Mainstream!
Republic Founder Kendrick Nguyen: Empowering 1 Million People with Private Investing!
Mayor Francis Suarez — Bringing Silicon Valley to Miami!
Jarrid Tingle, Managing Partner of Harlem Capital — Transforming the Face of Entrepreneurship
Kai Cunningham of Limited Ventures: Bridging the Gap Between VC and Pro Athletes + Entertainers
Chad Byers, Susa Ventures: Starting a VC, Robinhood’s Seed Round, & A WFT Exclusive Announcement!
—
For more Fintech insights, follow us below:
Wharton FinTech
