The Mello Millionaire with Tommy Mello

Episode: Startup Secrets in the Age of AI with Entrepreneur and Author Henrik Werdelin

Date: November 29, 2025

Episode Overview

In this lively episode, billionaire entrepreneur Tommy Mello sits down with Henrik Werdelin—serial founder, author, and co-founder of Bark (the company behind Barkbox and Bark Air)—to discuss what it really means to be an entrepreneur in the era of Artificial Intelligence. They explore how AI is changing the game for startups, why human-centric problem-solving is the ultimate advantage, and Henrik’s personal path from MTV to building beloved brands for dogs. This conversation is full of actionable tips, candid wisdom, and optimism for anyone building or scaling a business today.

Key Discussion Points & Insights

I. Henrik Werdelin’s Entrepreneurial Journey

• Sneaking into Opportunity:
  • Started career at MTV Networks in Denmark, where he pitched an internet show, broke into the studio at 2 a.m. to make a live broadcast—got promoted rather than fired ([01:47]).
• Serial Builder:
  • Led product development at MTV outside the US, spun out to build and exit multiple companies—some worked, some didn’t ([01:47]).
• Approach to Startups:
  • Today, believes startups require far less capital than before—“$20,000, $30,000 to build something pretty meaningful” ([00:26]).

II. Human-First Entrepreneurship in the Age of AI

• About the Book:
  • “Me, My Customer and AI” grew from work at Pre-Hype (startup studio/entrepreneur support) ([02:58]).
  • Explores how workflows can be ‘atomized’ and handled by AI agents, freeing entrepreneurs from “shitty work.”
• Core Philosophy:
  • Even as AI democratizes access, your authentic connection (“relationship capital”) with a specific customer becomes your defensible moat.
  • Quote:
    • “Your authenticity and your authority with a specific customer group...is what's going to make [your venture] special.” – Henrik ([04:08])
• Impact on Everyday Entrepreneurs:
  • AI doesn’t just enable unicorns; it levels the playing field for everyday people to build $1M ‘Donkey Kong’ companies—one-person businesses with real impact ([05:15]).

III. The Future of AI, Work, and Humanity

• AI as Foundational Tech—Not the Endgame:
  • AI is as foundational as electricity: “The best way to predict the future is to make it” ([07:00]).
  • AI will commoditize repetitive work (payroll, HR, call centers, inventory), but frees people for “meaningful work doing something on the top of an AI stack.”
• Crucial Human Skills:
  • “To really understand AI, you have to understand about humans.”
  • AI reflects the ‘average answer,’ so asking original, meaningful questions—understanding what makes people tick—remains the entrepreneurial differentiator ([08:40]).
  • Memorable Metaphor:
    • “The only way to use it [AI] as an Ironman suit is to become better at bench pressing yourself.” ([00:00], [09:36])

IV. Navigating Exponential Change and Staying Optimistic

• Worries & Perspective:
  • Despite excitement, Henrik admits he catastrophizes like anyone ([13:39]).
  • Staying positive is a choice: “You can either get super worried...or figure out what is the good things that we can do and then just spend a lot of time talking about that.” ([13:47])
  • Shares his father’s World War II wisdom to put today’s changes into context ([14:00]).
• The Coming Decade:
  • “If you look over the next 10, 15 years, I think it's going to be wild...I think you can basically strap in, enjoy the show, and have a good time while you see where that takes us.” ([15:41])

V. AI Tools and Building Businesses in Minutes

• Zero Excuses for Entrepreneurs:
  • Comparing the late ’90s (servers, developers, designers needed) to now (cloud services, instant platforms): “You really don't have any excuse anymore than to go out and do it.” ([17:18])
• Demonstrated Efficiency with AI:
  • Stories of entrepreneurs scraping web data, producing and distributing content across all platforms, with AI composing everything (post, image, video) in minutes and at negligible cost ([16:28]).
• Experimental Launching:
  • Advocates for iteratively testing small ideas—crafting a landing page, putting $50 in ads, calling early signups (what he calls ‘signal mining’), and carving the business based on actual feedback ([26:39], [29:54]).

VI. Barkbox and Bark Air – The Brand Stories

• Origin of Barkbox:
  • Started from a serendipitous cruise ship cabin share with future co-founder Matt (and a heart-shaped bed), sparked by a conversation about finding great dog products ([18:57]).
  • Vision: “Disney for dogs”—goes well beyond boxes; now has airlines, food, treats, and toys ([18:57]).
• Bark Air:
  • Created for people with big dogs who can't travel easily by air—began as a luxury service to set standards, with a goal to eventually make dog-friendly air travel affordable for everyone ([21:03]).
  • Memorable Moment:
    • Co-founder Matt put in a crate and flown Miami to New York as a publicity stunt to show how dogs feel in cargo ([22:57]).

VII. Practical Entrepreneurial Frameworks & Advice

• Five P’s for Entrepreneurial Inspiration ([24:02]):
  • Powers: What are you already good at?
  • Passions: What excites you?
  • Possessions: What do you have access to (assets, skills, network)?
  • Positions: What roles or communities are you a part of?
  • Potentials: What untapped opportunities or ideas are around you?
  • Use these to find problems you’re uniquely positioned to solve, not just cool new ideas.
• Idea Generation & Execution:
  • Use “it sucks that…” statements as the seed for business ideas.
  • Get ideas out of your head and instantly into an AI for processing, outlining, and even emailing to your team ([26:45]).
  • Actionable Advice:
    • “Get stuff out of the brain and get it onto something that is actionable. And I think it's such a superpower and nobody's doing it.” ([26:45])
• Testing and Focus:
  • Be promiscuous with ideas—test many cheaply, watch for real-world signal, then double down ([31:02]).
  • Build the first “snowballs” of ideas; the best ones will grow the fastest ([31:02]).
• Bezos Analogy:
  • With great resources and AI, it’s tempting to chase too many ideas—find balance between exploring and focusing, especially early in your career ([29:54], [32:33]).

VIII. Life, Business Philosophy & IPO Experience

• Human Hardware and Software:
  • Top advice (via Richard Branson): “Go to the gym.” If your body/mind breaks down, you can't succeed ([23:27]).
• Pursue ‘Interestingness’:
  • Inspired by the book Why Greatness Can’t Be Planned: “If you just pursue what you find to be deeply interesting...that will create the stepping stones...it will take you somewhere good.” ([34:19])
  • Chasing money = mercenary people; chasing what’s interesting = sustainable success ([34:19]).
• Partnerships:
  • Prefers co-founders and collaboration, though acknowledges solo entrepreneurship has merits for some personalities ([36:04]).
• Going Public:
  • IPO is emotionally powerful: “Like winning the Oscars or the Nobel Prize for entrepreneurship.” ([37:42])
  • Public scrutiny brings highs and lows—growing a robust business matters more than daily stock price ([38:53]).

Notable Quotes & Memorable Moments

• On AI’s Role:

  “The only way to use it as an Ironman suit is to become better at bench pressing yourself. And the only way that you can bench press better in entrepreneurship is to really understand what makes humans tick.” – Henrik Werdelin ([00:00], [09:36])

• On the Future for Entrepreneurs:

  “What I hope we can do is not just build a bunch of one person unicorns, but that we can build a bunch of...Donkey Kong[s]: one person companies that do a million turnover a year.” – Henrik Werdelin ([05:15])

• On Optimism vs. Worry:

  “You can either just get super worried...or figure out what is the good things that we can do and then just spend a lot of time talking about that. And I know it's a little bit naive, but, like, I'm deciding to do the latter.”
  – Henrik Werdelin ([13:47])

• Barkbox Startup Story:

  “The first time I ever meet this dude, we're lying in a heart shaped bed on a cruise ship and I'm kind of awkwardly have to put my hand over the duvet and kind of shake his hand. So that's how we met each other.”
  – Henrik Werdelin ([18:57])

• Execution with AI:

  “Get stuff out of the brain and get it onto something that is actionable. And I think it's such a superpower and nobody's doing it.”
  – Henrik Werdelin ([26:45])

• IPO Reflection:

  “Standing there and touching the bell and hearing go ding, ding, ding...is like winning the Oscars or the Nobel Prize for entrepreneurship, right?”
  – Henrik Werdelin ([37:42])

Timestamps for Key Segments

• 00:00 – Using AI as an Ironman Suit; Human Insight is the Real Superpower
• 01:47 – Henrik’s Early Entrepreneurship Story at MTV and Beyond
• 02:58 – Genesis of “Me, My Customer and AI”
• 04:08 – Human Connection as the Last Business Moat
• 05:15 – Everyday Entrepreneurship in the Age of AI
• 07:00 – The Future of AI and the Role of the Entrepreneur
• 09:36 – Why Understanding Humans Matters More Than Ever with AI
• 13:39 – Coping with Worry and Choosing Optimism
• 16:28 – Rapid Prototyping & Content Creation with AI
• 18:57 – Barkbox Origin Story (Heart-Shaped Bed Moment)
• 21:03 – Bark Air: The Airline for Dogs, Vision & Rollout
• 23:27 – Game-Changing Early Career Advice: Take Care of Your Health
• 24:02 – The 5 P’s Framework for Entrepreneurial Inspiration
• 26:39 – AI Tools for Moving from Idea to Execution
• 29:54 – Testing Many Ideas Quickly (“Signal Mining”)
• 34:19 – Pursuing Interestingness and Partnering with Cool People
• 36:04 – The Role of Partnerships in Entrepreneurship
• 37:42 – IPO Experience: The Emotional Impact
• 38:53 – Navigating Public Company Highs & Lows

Summary Takeaway

If you’re building in today’s AI-powered world, the playbook is wide open and the tools are at your fingertips. What matters most: a deep understanding of real human problems, the authenticity of your connection to your customers, the creativity to launch and test ideas, and the courage to stay positive (and healthy!) in a rapidly changing world. Barkbox’s heart-shaped-bed origin, AI prototyping tips, and the honest reflections on entrepreneurship—from “bench pressing yourself” to ringing the IPO bell—make this a must-listen for builders looking for wisdom and inspiration.

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