The Transcend Podcast

Matthew Kee didn't plan on being an entrepreneur, but a five-year fintech journey with his father changed that. After UpperRoom Technology failed in 2019 — the same year he lost his father and co-founder to cancer — Matthew channeled those lessons into Tundra Angels, a Green Bay–based angel network of 55+ investors that has evaluated over 160 startups and made 24 investments in Wisconsin companies...

Arjay McCandless doesn't consider himself an influencer, but the personal brand he built on the side became an unfair advantage that redefined his career. Most software engineers spend their careers chasing the next promotion at Big Tech. Arjay did the opposite. After climbing from SDE1 to SDE2 at Amazon in 18 months, he left the trillion-dollar company to join Maven as a social lead — a role that...

How do you go from scaling LinkedIn across Europe to tackling a $264 billion bottleneck in Madison, Wisconsin? Most founders start small and dream of reaching Big Tech. Kristin Isaac did the exact opposite. After a 20-year career building $15 million businesses from scratch for media and tech giants, Kristin walked away from the corporate safety net to solve a highly specific, massively expensive...

Aaryush Gupta is a serial entrepreneur and AI engineer who started day trading at 14, founded his first company at 16, and now serves as head of engineering at three companies — most notably Cylerity, a fintech/healthtech startup that has processed over $5 billion in healthcare claims and raised $4.5M+ in funding. Trust and distribution are the new moat. Fail fast, get in front of customers early....

In this episode, we sits down with Grant Watkins — founder turned venture capitalist at Generator, director of CS NEST at UW–Madison, and global startup ecosystem connector. Grant shares his journey from accidentally discovering entrepreneurship in high school DECA to teaching himself how to code during COVID, launching his own startup, and eventually moving into VC. Today, he helps student founde...

A UW engineering student turned a frozen line at Whiskey Jack’s into a venture-backed tech company - this is how he did it. Max Schauff didn't wait for a degree to start LineLeap. He launched his MVP by standing in the freezing cold on State Street to sell handwritten passes to his peers. We trace his evolution from winning the local Transcend Innovation Competition to scaling through Y Combinator...

We sat down with Jaxon Zemachson and Devin Mehta, who saw a gap at UW-Madison—while other Big 10 schools had established sports business conferences, UW didn’t. So instead of waiting, they built it themselves. Now, heading into year two, the Wisconsin Sports Business Conference is setting a new standard. WSBC is returning on February 27, 2026 Register here for WSBC2: https://www.wisconsinsbc.com/r...

From selling waffles at Mifflin as a UW-Madison student to landing product lines in Whole Foods and other major retailers, Sam Rockwell scaled a idea into a national brand - The Happi Co. Along the way, he and his cofounders partnered with major creators like Dave Portnoy and Snoop Dogg, proving that authentic influence moves real product. This episode breaks down his story. The Happi Co's scrappy...

Forget the big-city VCs—the most crucial first check for a student startup is being written by Strato VC, a student-led fund operating right in the heart of Madison's entrepreneurial energy. In this episode, we sit down with Shradha, Romeo, and James from Strato VC, one of the most exciting new organizations building the founder ecosystem at UW-Madison. They are a student-led, student-operated ven...

Building a startup is one of the hardest things you can do. So is completing a medical residency. Our guest today is doing both at the same time. In this episode, we sit down with Christina Henderson, the founder of Reliable Residence. She is a full-time anesthesiology resident right here at UW Health who is simultaneously building a high-growth venture to solve the exact "housing nightmare" she e...

What happens when a group of students decide to turn a simple problem—students who want local jobs on campus—into a fast-scaling startup? In this episode, we sit down with Nick Lawton, CEO and founder of SideShift, to talk about how he and his co-founder went from pitching on UW-Madison campus to now running a 13-person office in New York and generating a seven-figure ARR. Nick shares his journey...

In this episode, Trinity Krohn, a junior at UW–Madison and co-founder of the CampusConnect app, shares what she’s learned from starting three ventures: an Etsy slime shop, a dropshipping business, and now a growing app that’s live on the App Store. Trinity also opens up about creating Women in Entrepreneurship to inspire more women to feel welcome in startup spaces. We dive into: How to run effect...

Ever wondered what startups are really looking for in their hires or how to land your first role at one? In this episode, Ben Lukszys shares his journey in UW-Madison’s entrepreneurial ecosystem including running a startup accelerator, organizing the university’s 1st startup job fair, and matching students with local startups. We dive into the 4 key skill sets startups value most, the practical st...