Welcome to The Long View — a podcast for the builders and doers. Today's guest is Kevin Bailey.

Kevin spent over three decades building some of the most iconic brands in action sports and footwear, starting at Nike in the early 1990s before spending more than a decade in brand leadership at Vans. He rejoined VF Corporation in 2020, eventually rising to Global Brand President of Vans and later Chief Transformation Officer for the whole VF portfolio, before stepping away in 2024. Today he's the founder and managing director of Shadow Advisors, where he works directly with founders on brand and culture, and he sits on the advisory board here at Wildwood Ventures.

Kevin argues that losing your culture is often the first sign you're about to lose your business model. He explains why origin stories still matter years into a brand's life, and why leaders have to stay adaptive as the culture around them shifts. He shares hard rules for what to do — and not do — when you inherit a brand that's already built, starting with the discipline of listening. We also get into the mistake he saw firsthand at Vans: treating skateboarding as an activity instead of a way of life, and what that cost the brand. And he lays out the traits he now looks for in founders, drawn from his own experience advising them through culture crises of their own.

Please enjoy this conversation with Kevin Bailey, Founder and Managing Director of Shadow Advisors — who, in an age obsessed with AI, says he's bullish on the analogue world.

Find Kevin on LinkedIn: https://www.linkedin.com/in/kevindbailey/

Chapters

01:22 Kevin Bailey's Origin Story

06:07 The Importance of Company Culture

10:15 Stewarding Brand Culture at Vans

17:37 Advising Startups on Brand Development

21:52 Self-Diagnosing Company Culture

25:30 Patterns in Early Stage Founders

26:21 The Essentials of Founding: Grit and Perseverance

29:16 Trust and Team Dynamics in Startups

32:01 Overcoming Hindrances: Focus and Communication

38:41 Burnout and Mental Health: A Founder's Dilemma

44:22 The Future of Connection: Embracing the Analog World

Welcome to The Long View — a podcast for the builders and doers. Today's guest is William Hsu, co-founder and managing partner of Mucker Capital.

William's path to venture capital wasn't a straight line. At 22, he founded Buildpoint, only to be pushed out by his own board. He moved into the corporate world next, an unexpected chapter that taught him how to operate at a high level and, crucially, how to build relationships. One of those relationships was with his future Mucker Capital co-founder. From there, William built Mucker from $1 million in assets under management into one of the more recognized early-stage firms backing founders outside the traditional Silicon Valley mold.

In this conversation, William draws on the dot-com boom and bust to make sense of today's AI moment. He argues the current AI hype is three times the size of 1999's, and just as capable of getting ahead of itself. He shares the ironies of fundraising then and now. He explains why patient capital matters more than ever. And he makes the case that building something customers love at a premium price is still the only durable path to success. We also get into his hardest career moment, what it taught him about humility and resilience, and how he thinks about culture and leadership as someone who still identifies more as an entrepreneur than an investor.

Please enjoy this conversation with Will Hsu, current founder of Mucker Capital — an investor who will answer almost every cold email he gets. In fact, 25% of his portfolio came from cold outreach.

Find William on LinkedIn: https://www.linkedin.com/in/william-hsu-032273/

Chapters

02:03 The Dot-Com Bubble and Its Lessons

03:57 Fundraising Dynamics: Then and Now

05:34 The Silicon Valley vs. LA Dynamic

08:11 Navigating the AI Hype Cycle

11:20 The Journey of Build Point: A Cautionary Tale

14:04 The Importance of Experience in Entrepreneurship

16:51 The Transition from Entrepreneur to Investor

18:50 Building a Strong Company Culture

26:53 Cultivating a Positive Company Culture

29:22 Decisiveness and Speed in Decision-Making

30:57 The Importance of Grit and Resilience

35:32 Lessons from Mucker Fund One

40:13 Preparing the Next Generation for AI

42:59 Contrarian Views on SaaS and Applications

Donna Harris is the Founder and CEO of Builders + Backers, the world's first AI-powered venture studio helping entrepreneurs everywhere turn ideas into real companies.

Over her career as a six-time entrepreneur and top-ranked seed-stage investor, she co-founded 1776 in Washington, DC, served as Managing Director of the Startup America Partnership, and is now General Partner of 1776 Ventures — giving her a front-row seat to what actually separates thriving startup ecosystems from ones that stall out.

In this episode we discuss:

• What's actually broken in the startup ecosystem
• The truth about alternative funding options beyond venture capital
• How AI is reshaping the future of venture building
• Why so much "startup success" is an illusion
• Lessons from Tulsa on what makes an ecosystem work
• Why human judgment is the one thing AI can't replace

Find Donna on LinkedIn: https://www.linkedin.com/in/dharrisindc/

Enjoy!

Timestamps:
0:00 Intro
04:24 Building the Startup Ecosystem in D.C.
07:22 Reflections on Startup Success and Challenges
09:58 Navigating Alternative Funding Options
19:25 The Role of AI in Shaping the Future of Startups
22:27 Evaluating Venture Building Models
25:08 The Reality of Startup Growth and Expectations
31:06 The Illusion of Startup Success
33:17 The Reality of Entrepreneurship
35:42 Rethinking Economic Development
38:34 Successful Ecosystems: Lessons from Tulsa
41:07 Myths in Entrepreneurship
44:00 Leveraging AI Tools for Startups
48:36 The Human Element in an AI World

Welcome to The Long View, a podcast for the builders and doers. Today's guest is just that. Ron Schneidermann was the CEO of AllTrails, largely considered one of the top outdoor / adventure platforms in the world. I used it this weekend to hike a 14er with my family. He took it from six people and half a million in ARR to over 100 million registered users worldwide and an exit, which he talks about. Before that, Ron wrote the business plan for Liftopia in the early 2000's using books he bought at Barnes & Noble. Ron talks about what the unglamorous version of startups actually looks like: self-funding, brutal prioritization, and the hardest questions a CEO has to ask themselves. He has hot takes on co-founders, on when NOT to raise money, on culture as the only real competitive moat, and on why, in an age where building anything is trivially easy, human taste and judgment are the last defensible thing we have. Now he's CEO of Acley, an AI-powered standardized-test prep platform, where the same philosophy he's carried through every chapter is running the show.

Ron’s LinkedIn: https://www.linkedin.com/in/schneidermann/

Most venture capitalists have a tech or finance background but Mel Strong took a non-traditional route into the industry, from teaching first grade in West Philly to working at Nike, and ultimately becoming a pioneering VC. In this episode, she shares her unlikely journey, the lessons learned from building iconic brands, and how her diverse experiences shape her approach to investing today. You'll discover how Mel’s unconventional path, teaching, journalism, and global corporate stints, gives her a unique perspective on founder resilience, market opportunities, and leadership authenticity. We break down her approach to mentorship, the art of cold outreach, and maintaining grace in high-stakes environments. Perfect for founders, investors, and anyone curious about how extraordinary careers are built from unexpected beginnings.

Check out Melanie on LinkedIn: https://www.linkedin.com/in/melanie-strong/

In this episode, entrepreneur and outdoor industry leader Robin Thurston shares the lessons behind building, scaling, selling, and reviving category-defining companies. From the rise of MapMyRide and its acquisition by Under Armour to leading the future of Outside, Robin breaks down the realities of startup timing, resilience through growth cycles, and the power of vision-driven leadership. The conversation explores storytelling, risk-taking, AI-driven innovation, outdoor community building through Outside Days, and where the next wave of fitness and outdoor tech opportunities is emerging. 

The Long View with Jesse Marble is a podcast for builders and founders. The ones who know the game is fast but isn't won in a quarter. Every episode, I sit down with founders, investors, athletes, authors, operators, leaders who've been through it, the sleepless stretches, the bets that looked stupid until they didn't, the unsexy work that compounds when nobody's watching. We talk about conviction, survival, and what it actually looks like to build something that lasts. No hacks. No highlight reels. Guards down. 

Check out Robin Thurston on LinkedIn: https://www.linkedin.com/in/robinthurston/