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. Along the way, he built an audience of nearly 8,000 subscribers through the Tundra Angels Angle, the weekly newsletter he writes to be the "learning curve shortener" he wishes he'd had as a founder.

In this episode, we explore what it really takes to trade the safety of a corporate banking career for the high-variance world of startup investing.

We dive into:

• What Most Founder's Miss: Why scoping the wrong problem can kill your startup
• The Validation Playbook: His exact LinkedIn strategy for turning cold outreach into give-back conversations
• Why Wisconsin-Only: How niching down geographically became Tundra's biggest competitive edge
• And more!

Learn more about Tundra Angels here: https://www.tundraangels.com/

Subscribe to the Newsletter: https://newsletter.tundraangels.com/

Follow Matthew Kee: https://www.linkedin.com/in/matthewdkee/

Transcend IG: @transcenduw

Transcend Website: www.transcenduw.com

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

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 blurs the lines between engineer, marketer, and GTM operator. Along the way, he built a personal brand of 400K+ followers across TikTok, Instagram, and YouTube as ArjayTheDev, teaching system design and AI engineering to the next generation of builders.

In this episode, we explore what it really takes to trade the safety of a FAANG career for the freedom of the startup world.

We dive into:

• The College Playbook: Why CS classes alone won't land a top offer, and the four extracurricular moves that actually do
• The Social Media Catalyst: Why a personal brand is the highest-leverage move a software engineer can make today
• High-Velocity Environments: Why Arjay now codes more at a startup than he ever did at FAANG
• Building with Claude Code: Arjay's fully automated video pipeline and his core rule for working with AI
• And more!

Learn more about Maven here: https://maven.com/

Check out the Arjay McCandless Show: https://open.spotify.com/show/033BNeUbxt1qxUDeJCnwF3?si=e8db0d43f28b4710

Follow Arjay McCandless: https://www.linkedin.com/in/arjay-mccandless-9178b4198/

IG/YT: @arjay_the_dev

Tik Tok: @arjay_mccandless

Maven LinkedIn: https://www.linkedin.com/company/maven-hq/

Transcend IG: @transcenduw

Transcend Website: www.transcenduw.com

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

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 problem: B2B software engineers wasting up to half their time on customer support tickets. In this episode, we unpack how the playbook for scaling global tech giants translates when building an early-stage startup from absolute zero.

Learn more about Strudel AI here: ​​https://strudel.io/

We dive into:

• How to build a high-leverage professional network before you graduate
• Why prioritizing lifelong learning is an elite founder's ultimate competitive edge
• How to convince world-class engineers to take a risk and join your pre-seed vision
• How to adapt global, enterprise-scale go-to-market strategies for your early-stage startup
• And more!

Follow Kristin Isaac: https://www.linkedin.com/in/kristinisaac/

Strudel AI LinkedIn: https://www.linkedin.com/company/strudel-ai/

Transcend IG: @transcenduw

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

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

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.
• AI has fundamentally changed what it means to build.
• The solo founder unicorn is coming.

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/