In this episode of the Sunny Ray Show, host Sunny Ray talks with Brian Lee, co-founder of Gilder, a community built to connect founders across stages so they can share hard-won lessons and avoid common startup pitfalls. Brian traces his path from studying political science and entrepreneurship at Purdue, through roles at major CPG companies like Hershey and Ferrara, to launching an escape room business with a college friend in 2015. He shares the origin story of Romely, a local-experience travel platform born from a trip to Scotland, and how the pandemic forced a pivot toward B2B partnerships with tourism boards and chambers of commerce. Brian reflects on lessons from two exits, the role of trust and risk in partnerships, and why he later co-founded Gilder after seeing how fragmented founder support systems were. The conversation closes with his thoughts on defensibility, market timing, and what the next generation of founders should focus on as building products becomes easier but standing out becomes harder.
Two-time founder Brian Lee on Purdue, Hershey, two exits, and building Gilder to help founders avoid common startup pitfalls.
Can you share what Gilder does for those tuning in for the first time?
Gilder started three years ago from our own experience across the entrepreneurial ecosystem. Founders at any stage, whether pre-revenue or at 10 million ARR, face similar problems regardless of industry. We built a space to put strong operators and founders together to share knowledge, save each other time and heartache, and reduce the high failure rate so many entrepreneurs face.
You studied political science and entrepreneurship at Purdue, an unusual combination. What was going on in your head at that age?
I actually started in business but failed calc 1 a few times and realized math wasn't for me. I pivoted to political science thinking I might pursue law or public policy, since I liked community impact. Entrepreneurship was more of a minor. Honestly, House of Cards had just come out and politics seemed interesting, which shows how little you know picking a major at eighteen.
What did working inside big CPG companies like Hershey and Ferrara teach you about products and branding?
Those experiences gave me a great baseline before I started my own ventures. At Hershey I worked on Lancaster, a new caramel product, which was a huge deal since they hadn't launched anything internally in decades. It taught me that even a legacy brand can only carry a new product so far, especially now with DTC and social media changing how products break through.
Take us back to launching your first company in 2015. Was it a spark or something that built over time?
My best friend and co-founder was teaching English in Japan, and a group of us visited him and did an escape room, which was still pretty new. Even without speaking Japanese we had a blast, so we thought it could work in the States. We opened one in Evanston as our nights-and-weekends project while still working full-time jobs.
By the time you'd exited two companies and worked across multiple industries, what was the biggest lesson you couldn't have learned from a textbook?
A lot of it comes down to luck and trust. I ran a business with a partner in Youngstown, Ohio for two years, sold it, and never met him in person, we found each other on Facebook Marketplace. Some founder friends have gotten burned doing similar things. You have to extend some blind trust while still protecting yourself, and everyone has a different appetite for that risk.
Tell us the origin story of Romely.
My co-founder Bonet, our friend Dan, and I were on a trip to Scotland when Dan came down with pneumonia and got quarantined in the Airbnb. Bonet and I wandered the city and realized Google, Yelp, and blogs only surfaced touristy spots or took hours to sift through. Romely became about helping people feel like locals in a new city, or tourists in their own.
What frustration in the startup ecosystem made you realize you needed to build something like Gilder?
After Romely, I joined an accelerator in Austin as head of product where I met my Gilder co-founders. Working with thousands of founders, from Series A to pre-revenue, we saw the same pain points repeat, but support was fragmented by region, industry, or stage. Founders were yearning for real connections that could shave hundreds of hours off their trial and error.
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