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 founders make the mental shift from class project to real company.

We dive into:

• How to make the mental shift from student to startup founder
• Why every founder should read The Lean Startup
• The importance of traction
• Lessons from working with Japanese startups

This conversation is packed with practical insights on validation, traction, global startup trends, and what founders actually get wrong.

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, revealing the gritty reality of turning a campus side-hustle into a national platform. This episode serves as a masterclass of the student-founder, proving that your university years are the ultimate unfair advantage for building a startup.

Download LineLeap here: https://lineleap.com/

We dive into:

• The art of "doing things that don't scale" to validate an MVP
• Leveraging the university ecosystem to gain an unfair advantage
• Navigating the transition from student project to venture-backed company
• The psychological shift from "founder" to "executive"
• And more!

Transcend Competition sign-ups are open now! (Due February 20, 2026): https://www.transcenduw.com/upcoming

Follow Max Schauff: https://www.linkedin.com/in/max-schauff-3a5393104/

LineLeap IG: @lineleap

LineLeap LinkedIn: https://www.linkedin.com/company/lineleap

Transcend IG: @transcenduw

Transcend Website: www.transcenduw.com

Transcend UW LinkedIn:www.linkedin.com/company/transcenduw

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/register-for-wsbc2

We dive into:

• Building in professionalism from day one - despite being a student-run operation
• Pitching yourself with clarity and confidence
• Recruiting and retaining a team that’s constantly raising the bar
• What to look for in a good co-founding partnership
• And more!

Transcend Application (Due February 16, 2026): https://www.transcenduw.com/upcoming

WSBC IG: @wisconsinsbc

WSBC Website: https://www.wisconsinsbc.com/

WSBC Linkedin: http://linkedin.com/company/wisconsin-sports-business-conference

Transcend IG: @transcenduw

Transcend Website: www.transcenduw.com

Transcend UW Linkedin: www.linkedin.com/company/transcenduw

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 beginnings to scaling in just 4–5 years
• Landing a spot in Whole Foods and other retailers
• How to start a business with your friends — and STAY friends through pressure
• Why creator-led partnerships help smaller brands break through

Happi Co: https://thehappi.co/

Sam's Linkedin: https://www.linkedin.com/in/samuelrockwell/

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 venture fund that invests in undergraduate entrepreneurs with idea-stage companies. We get their firsthand perspective on what it’s really like to be a venture capitalist and explore Strato's crucial role in transforming our campus's startup landscape.

We dive into:

• A clear breakdown of what a Venture Capital firm is, where they get their money, and why founders need to care.
• Pre-seed, Seed, and Series A—we demystify the stages of venture funding and what VCs expect to see at each level.

• How Strato’s due diligence process differs when evaluating a fellow student and how they assess 'exit potential.'

• How an investor handles the tough conversation when a funded team starts to go "off the rails."

Shradha: https://www.linkedin.com/in/shradha-godishala/

Romeo: https://www.linkedin.com/in/romeo-trikolas-347083267/

James: https://www.linkedin.com/in/jamesotoole8/

Strato VC website: https://stratovc.com/

Strato VC Events: https://luma.com/stratovc?k=c

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 experienced as a medical student. We get her firsthand perspective on what it’s really like to be a "founder-physician" and explore her journey of turning a personal pain point into a rapidly-scaling business.

We dive into:

• The "lightbulb moment" that turned a real-world problem into a business.
• How to manage the intense context-switch between the high-stakes, structured world of the hospital and the chaotic, ambiguous world of a startup.
• The story of walking into a major developer's office unannounced and how to build partnerships from nothing.
• How a decade of rigorous medical training can actually provide an advantage in entrepreneurship.
• Actionable productivity habits for student founders who are also balancing a demanding schedule.

More from Christina:

LinkedIn: https://www.linkedin.com/in/christina-henderson-aa0a55a1/

Reliable Residence website: https://reliableresidence.com/

Instagram: Reliable_Residence

Facebook: https://www.facebook.com/p/Reliable-Residence-61575755723700/

Tik Tok: Reliable_Residence

More from Transcend:

Transcend IG: @transcenduw

Transcend LinkedIn: https://www.linkedin.com/company/transcenduw/

Transcend Website: https://www.transcenduw.com/

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 from sales and private equity to entrepreneurship, the mindset that kept him going when no one believed in the idea, and the pivotal decisions that led to SideShift’s crazy growth.

We also dive into:

• The value of conviction in your team and your product
• The deal that changed the trajectory of SideShift
• Why every founder should talk to their customers
• How SideShift has scaled and pivoted within only 2-3 years

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 effective customer discovery interviews & get your first beta testers
• Building community and confidence in male-dominated fields like tech & entrepreneurship
• Why your network is your net worth (and how to grow it)
• Time management tips for balancing school, startups, and student leadership

Trinity’s Linkedin: https://www.linkedin.com/in/trinity-krohn/

Tik Tok: @trin.talks.tech

Transcend UW Linkedin: www.linkedin.com/company/transcenduw

Transcend IG: @transcenduw

Transcend website: www.transcenduw.com

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 steps you can take to stand out, and what it actually takes to get hired by a startup.

Ben’s Linkedin: www.linkedin.com/in/ben-lukszys/

Transcend UW Linkedin: www.linkedin.com/company/transcenduw

Transcend IG: @transcenduw

Transcend website: www.transcenduw.com/

We talked with Jake about his UW experience, freelancing work, and running successful social media platforms.