Mar 15, 2021 · 48m · 20vc
20VC: Tony Fadell "The Father of The iPod" on Mentors, Self-Doubt, Vulnerability, His Relationship To Money, Why Entrepreneurs Need to Be Coachable, Why VCs Need To Be More Direct & Why The First Trillionaire Will Innovate Around Climate Change
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of 20VC, host Harry Stebbings interviews iPod co-creator and Nest founder Tony Fadell about founder coachability, personal growth, authentic networking, and FutureShape's investment focus on deep-tech and environmental solutions.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 24.9% of the talking time here. How this is scored →
Harry as informed peer 1.9 Guest teaching 5.2 Guest disagreement 3.2 Harry pushing back 1.7
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 19:14 Rejection of Learning from Success
Tony forcefully shuts down Harry's mentor's perspective with repeated 'no, no, no, no's, insisting that learning only occurs through action and failure.
Hardest push from Harry ▶ 19:00 Challenging Failure vs Success PremiseHarry directly challenges Tony's perspective on failure by introducing a counterargument from a wealthy mentor who claims success is a better teacher.
Biggest teaching moment ▶ 26:50 Exposing the Myth of Plastic RecyclingTony educates Harry on the systemic flaws in recycling, explaining how single-digit recycling rates and virgin plastic economics result in environmental dumping.
Harry holds his own ▶ 31:03 Highlighting Deep Tech Funding GapsHarry demonstrates domain expertise by pressing Tony on the structural lack of Series B and C lifecycle funding for non-software deep tech ventures.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Entrepreneurial Origins and Childhood Lessons in Sales | 1 | 3 | 0 | 0 | Harry asks about Tony's childhood sales experiences and father's sales advice. Tony shares stories about his third-grade egg route and Levi's sales philosophy without any conflict. | |
| Distinguishing Genuine Relationships from Transactional Intentions | 1 | 5 | 1 | 0 | Harry vulnerably asks how to distinguish genuine friends from transactional people as his platform grows. Tony advises him on conducting diligence and spotting fake relationships. | |
| The Role of Mentorship and Founder Coachability | 2 | 6 | 4 | 3 | Harry questions whether top founders really need to be coachable. Tony forcefully dismisses life coaches and insists that founders tackling unprecedented challenges must remain coachable. | |
| Delivering Direct Feedback, Boldness, and Overcoming Public Speaking Fear | 2 | 5 | 5 | 2 | Harry asks how to deliver harsh feedback, admitting his own British aversion to conflict. Tony sharply criticizes board meeting politeness and shares Bill Campbell's aggressive feedback style. | |
| Overcoming Imposter Syndrome and Learning Through Action | 3 | 6 | 6 | 4 | Harry tests Tony by quoting a mentor who claimed people learn more from success than failure. Tony forcefully rejects this notion, declaring that learning only comes from doing and failing first. | |
| FutureShape's Investment Philosophy and the Cannabis Opportunity | 2 | 4 | 2 | 1 | Tony explains FutureShape's role as mentors with money and answers Mickey Malka's question by picking cannabis over e-bikes and plastics due to its dual medicinal and vice dynamics. | |
| Rethinking Plastics and Building a Circular Economy | 2 | 7 | 5 | 2 | Harry asks why plastic recycling is bullshit. Tony details his experiences in Indonesia and breaks down how low recycling rates and virgin plastic economics create environmental destruction. | |
| Deep Tech, Infrastructure Transformation, and Atoms vs. Bits | 3 | 7 | 4 | 3 | Harry challenges deep tech viability by pointing out the lack of late-stage VC funding for hardware. Tony critiques fast-money VC culture and explains the macro shift back to physical infrastructure. | |
| Agriculture Financing Innovations and Personal Relationship to Wealth | 2 | 5 | 2 | 1 | Tony explains how agtech requires fintech business models to enable farmer adoption. He then reflects on downsizing his wealth, explaining that material possessions eventually become headaches. | |
| Quickfire Round and Future Outlook | 1 | 4 | 3 | 1 | In the quickfire round, Tony recommends Thinking Fast and Slow and pushes back on the societal pressure to be liked over being respected in business. |
Statements from this episode (20)
Fadell: Levi's jeans were black market currency in 1970s Russia
“In fact, they were traded as black market currency in Russia. So you could trade US Levi jeans to get, I don't know, caviar, who knows what it was in Russia, but it was literally black market currency.”
Fadell: Cold outreach is ignored unless vetted via mutual network
“Anybody who comes to me cold, because I'm like, they probably want something. And so through that, I try to make sure that through the network, I'm like, do you know this person? What are they about?”
Fadell: Pitching requires upfront transparency, not fake friendship
“If you are selling someone, you gotta be upfront and say, look, I'm talking to you about this. This is why I want your time. I think you could be helpful with this, but be upfront on what the game is about and what you're trying to discuss with people.”
Fadell: Founders should avoid life coaches because they lack real experience
“If anyone has a life coach title, Jesus Christ, that's like walk on down the street, just forget about it. Because typically if you see a life coach, they didn't have enough experience, right?”
Fadell: Founders building novel products must be highly coachable
“I think anybody who's trying to do something that the world has never seen before or trying to work with people who've never, they better be coachable. Because you're going to be so narrowly focused. You're going to be so heads down. You're going to be on a mi…”
Stebbings reveals his years-long struggle with bulimia and eating disorders
“I was bulimic before and had troubles with eating disorders for years.”
Fadell: Quiet people rarely succeed in business, regardless of intelligence
“The quiet person in the corner Doesn't typically succeed because they're not getting other people excited and interested in what they're saying or what they're thinking, even if they're the smartest people in the world.”
Fadell: Founders lacking daily anxiety are not taking enough risks
“And I always say if you don't have butterflies in your stomach each day, you're either not paying attention or you're not pushing hard enough and taking enough risk.”
Fadell: College and modern higher education are fundamentally backwards
“I think college in our education system is entirely backwards. You sit here and you go learn something and you learn for years and years and years, and then you're told to go do.”
Fadell: Advisors without skin in the game just want consulting fees
“Advice when they're not, like, putting money behind it and, like, truly working on it, that's usually just somebody trying to make some consulting dollars.”
Fadell: Cannabis is a better investment than e-bikes or plastics
“Cannabis is actually medicinal, and it's a vice. It's both. And so when you can have those two dynamics together, when you can actually help people, whether that's recreationally or medically, and you can have all of the uplift of the recreational side for the…”
Fadell: Single-use plastic recycling is "a bunch of bullshit"
“Recycling is basically a bunch of bullshit, especially when it comes to single-use or low-use plastics versus durable-use plastics.”
Fadell: FutureShape backs startups that mine urban waste landfills
“We're finding at FutureShape all kinds of businesses that literally go and mine urban mines. Instead of mining the earth, let's go mine the stuff we've already extracted and get it out of those things into valuable mineral streams again so we can reuse them.”
Fadell: Physical infrastructure will dramatically change over the next 20 years
“Almost every piece of infrastructure around us is going to change in a dramatic way with atoms over the next 10 to 20 years.”
Fadell: SPAC managers call daily seeking ESG-compliant portfolio companies
“I can't tell you how many calls I've got. I got a SPAC. What do you have with ESG goals in your portfolio? Every day.”
Fadell: The world's first trillionaire will be someone who fixes climate change
“The first trillionaire in the world is someone who's going to fix climate change. It's true, because it's going to be all about atoms, and it's going to be about changing the infrastructure around us.”
Fadell: Most successful agtech startups are actually fintech companies first
“Most of our ag tech companies are FinTech companies first.”
Fadell: Financing SMB tech adoption represents a massive profit opportunity
“We are going to have to finance so many things, and this is where the finance industry can make a ton of money if they start looking at these small, medium-sized businesses And start looking at the technology that they could adopt if they were financed properl…”
Fadell: Earning respect by being direct beats striving for popularity
“You got to be respected and you got to speak your mind and be damned if people don't like you for a little while. Typically, they'll come around and respect you. So it's like, say the tough things, because we're only on this planet for so long, and stop all th…”
Fadell: Randy Komisar was the best board member he ever had
“Official board member, I would say, would be Randy Komisar. Randy Komisar, he's straight. He and I both had Bill Campbell as a mentor. He saw things that other people didn't see. He backed you up. He stood behind you. He told you when you were screwing up. And…”