The Transcend Podcast

Transcend UW
  • 5.0 (1)
  • Entrepreneurship
  • Updated Biweekly

Welcome to the Transcend Podcast - the show where we highlight the stories of student founders at UW–Madison, local entrepreneurs across the Midwest, and campus leaders shaping UW into a hub for entrepreneurship. This podcast is presented to you by Transcend UW. We are the nation’s largest student-run pitch competition and we also connect students with the resources and opportunities to create their own ventures. Last year was our 10th annual competition and we were able to award $50K in prize money. Check out our socials to learn more or join our executive team: Transcend UW Linkedin: www.linkedin.com/company/transcenduw Transcend IG: @transcenduw Transcend website: www.transcenduw.com/

  1. Matthew Kee: How Failing as a Founder Made Him a Better Investor

    May 11

    Matthew Kee: How Failing as a Founder Made Him a Better Investor

    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 startupThe Validation Playbook: His exact LinkedIn strategy for turning cold outreach into give-back conversationsWhy Wisconsin-Only: How niching down geographically became Tundra's biggest competitive edgeAnd 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

    50 min
  2. Arjay McCandless: How to System-Design Your Career

    May 4

    Arjay McCandless: How to System-Design Your Career

    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 doThe Social Media Catalyst: Why a personal brand is the highest-leverage move a software engineer can make todayHigh-Velocity Environments: Why Arjay now codes more at a startup than he ever did at FAANGBuilding with Claude Code: Arjay's fully automated video pipeline and his core rule for working with AIAnd more!Learn more about Maven here: https://maven.com/ 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

    59 min
  3. Kristin Isaac: From Scaling Big Tech to Tackling a $264B Bottleneck with AI

    Apr 27

    Kristin Isaac: From Scaling Big Tech to Tackling a $264B Bottleneck with AI

    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 graduateWhy prioritizing lifelong learning is an elite founder's ultimate competitive edgeHow to convince world-class engineers to take a risk and join your pre-seed visionHow to adapt global, enterprise-scale go-to-market strategies for your early-stage startupAnd 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/

    50 min
  4. Aaryush Gupta: How AI is Changing the Startup Game

    Apr 20

    Aaryush Gupta: How AI is Changing the Startup Game

    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.

    44 min
  5. Grant Watkins: From Being a Founder to working at a Global VC Fund

    Feb 23

    Grant Watkins: From Being a Founder to working at a Global VC Fund

    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 founderWhy every founder should read The Lean StartupThe importance of tractionLessons from working with Japanese startups This conversation is packed with practical insights on validation, traction, global startup trends, and what founders actually get wrong.

    39 min
  6. Max Schauff: From Selling Passes in the Cold to Creating the Go-To App for Nightlife

    Feb 2

    Max Schauff: From Selling Passes in the Cold to Creating the Go-To App for Nightlife

    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 MVPLeveraging the university ecosystem to gain an unfair advantageNavigating the transition from student project to venture-backed companyThe 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

    1h 12m
  7. WSBC: The Story of Building UW's 1st Sports Business Conference

    Jan 19

    WSBC: The Story of Building UW's 1st Sports Business Conference

    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 operationPitching yourself with clarity and confidenceRecruiting and retaining a team that’s constantly raising the barWhat to look for in a good co-founding partnershipAnd 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

    34 min
  8. Sam Rockwell: Selling Waffles at Mifflin to Partnering with Dave Portnoy & Snoop Dogg

    12/08/2025

    Sam Rockwell: Selling Waffles at Mifflin to Partnering with Dave Portnoy & Snoop Dogg

    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 yearsLanding a spot in Whole Foods and other retailersHow to start a business with your friends — and STAY friends through pressureWhy creator-led partnerships help smaller brands break throughHappi Co: https://thehappi.co/ Sam's Linkedin: https://www.linkedin.com/in/samuelrockwell/

    38 min
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About

Welcome to the Transcend Podcast - the show where we highlight the stories of student founders at UW–Madison, local entrepreneurs across the Midwest, and campus leaders shaping UW into a hub for entrepreneurship. This podcast is presented to you by Transcend UW. We are the nation’s largest student-run pitch competition and we also connect students with the resources and opportunities to create their own ventures. Last year was our 10th annual competition and we were able to award $50K in prize money. Check out our socials to learn more or join our executive team: Transcend UW Linkedin: www.linkedin.com/company/transcenduw Transcend IG: @transcenduw Transcend website: www.transcenduw.com/

Information

  • Creator
    Transcend UW
  • Years Active
    2021 - 2026
  • Episodes
    13
  • Rating
    Clean
  • Copyright
    © Transcend 2025
  • Show Website
    The Transcend Podcast