The Transcend Podcast

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/

The Transcend Podcast is a business podcast hosted by Transcend UW, with 13 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Transcend UW hosts The Transcend Podcast, a business show with 13 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

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  The Transcend Podcast

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

  May 11, 202650 min

  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

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  The Transcend Podcast

  Arjay McCandless: How to System-Design Your Career

  May 4, 202659 min

  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

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  The Transcend Podcast

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

  Apr 27, 202650 min

  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/

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  The Transcend Podcast

  Aaryush Gupta: How AI is Changing the Startup Game

  Apr 20, 202644 min

  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.

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  The Transcend Podcast

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

  Feb 23, 202639 min

  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.

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