Jason Fried is the Founder & CEO @ Basecamp, the project management and team communication tool trusted by millions. Over an incredible 22 year journey, they have scaled to over 3.5M accounts and in 2020 they went back to being a multi-product company with the launch of their integrated email client & service, HEY. Jason is also the co-author of the widely acclaimed, ReWork and has also made several angel investments in the likes of Intercom, Gumroad and Hodinkee to name a few. In Today’s Episode You Will Learn: 1.) How Jason Fried made his way into the world of startups and came to found one of the leading project management and team communications tools in the form of Basecamp? 2.) How does Jason analyse and evaluate his relationship to money? Why does Jason believe that he has this inherent downside protection when it comes to money? How does he structure his personal finances between stocks, cash, crypto etc etc? What have been some of Jason's biggest lessons when it comes to tying happiness to monetary levels? 3.) What does Jason mean when he says, "I have a fantasy of getting fired"? How does Jason think about knowing when is the right time to step away from the business? What would he like to do with that time? How does Jason feel about the challenge of tying his identity to his company? What are the dangers of doing so? 4.) How does Jason approach decision-making frameworks? What does Jason believe is the right way to respond when a decision does not go as planned? Where do many make mistakes here? Does Jason feel regret with decisions? How does Jason try and minimise regret? 5.) How does Jason feel about his biggest insecurities as a leader and CEO today? What are Jason's views on a CEO's ability to have self-doubt and be vulnerable? How have his views on this changed over the years? In what way has having kids impacted Jason's operating mindset? How has it changed what he values and appreciates? Item’s Mentioned In Today’s Episode Jason’s Favourite Book: In Praise of Shadows As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Tony Fadell, often referred to as “the father of the iPod,” is currently Principal @ Future Shape, a global investment and advisory firm coaching engineers and scientists working on foundational deep technology. Prior to Future Shape, Tony was the Founder & CEO @ Nest Labs, the company was ultimately acquired by Google for a reported $3.2Bn. Before Nest, Tony spent an incredible 9 years at Apple Inc, where, as SVP of Apple’s iPod division, he led the team that created the first 18 generations of the iPod and the first three generations of the iPhone. Fun facts, Tony has filed more than 300 patents for his work and is also a prolific angel investor having invested in the likes of mmhmm and Nothing to name a few. In Today’s Episode With Tony Fadell You Will Learn: I. The building blocks of an entrepreneur What was the moment that Tony realised that he wanted to be an entrepreneur? “I got my first money when I was in third grade, because I had an egg route. We'd go get eggs from the farmer, and I'd load them in my wagon. Then my younger brother and I would go door to door around the neighborhood, and we'd sell eggs. And that was an every week or every other week situation. And I got money in my hands. And I was like, Oh my God, I can do whatever I want with that money – I don't have to ask anybody, I can just do it. And so that was the level of freedom that, especially when you're young, feels really cool. And then as I got older, I started to buy Atari video game cartridges for my 2600 (yes, I'm that old!), and that was really, really fun too.” What was the biggest lesson that Tony learned from his father on sales and building trusted relationships? "And he said, very clearly, Look, this is a relationship. If I make this person successful, he's gonna want to come back to me over, and over, and over. But if I sell him something and it doesn't sell, and he has to discount and he loses money, he's not going to come back. Even if I don't have the right product, I'll tell him where to go to get the right product they're looking for, or if they're picking the wrong one, I'll tell them, here's the right one, because my job is to make them successful. Because if they're successful, they'll come back to me year after year after year. And even when we have a down year, they're going to trust me, and they're going to come back." II. Reflections on experience How does Tony Fadell think about and assess his own relationship to money? How has it changed over the years? "So my relationship to money now is that it's just a means to make change happen. And so literally, for me, I can just have a backpack, my computer, my phone, a couple of roller bags with my clothes. And that's enough to live life with my family. I don't need all this other stuff. COVID taught me that even further." How does Tony determine true friendships vs transactional relationships? “If it's not a reference – if it's not coming from somebody saying, Hey, you really need to meet this person – I take everything with a grain of salt. With anybody who comes to me cold, I think they probably want something. I try to find that out through the network, Do you know this person? What are they about?" III. Tony Fadell on becoming a mentor Why does Tony Fadell believe that founders have to be "coachable"? “I think anybody who's trying to do something that the world has never seen before, or trying to work with people who are, they'd 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 so on a mission, that sometimes you'll be blinded, and you'll need somebody to come from left field and go, Wait a second, dude, you're not thinking about this right." What are the core signs that an individual is coachable? Trustworthiness 2. Willingness to listen What does Tony believe is the right way to deliver advice without fluff? "First, it's about trust. You have to be able to have a trusted relationship with somebody. And second, there are different ways of delivering a message. You can deliver a message the first time in an iron-fist-in-a-velvet-glove kind of way. But sometimes the velvet glove is going to come off." How do people make mistakes when giving advice? “I'm in too many board meetings; we have over 200 investments. I've seen all kinds of different CEOs and different boards, where the investors don't want to feel like they're going to get a bad rep because the CEO is going to say something if they say something negative." What does Tony Fadell advise founders when it comes to finding mentors? “Usually, a really great mentor is going to be highly selective. They're going to be like, I don't want to work with you. They only have so much time for people who are actually coachable." What are the characteristics of the best mentors? "You're gonna have tough love with them, you're gonna say things that they don't want to hear, you're not going to be liked all the time. Hopefully, one day, you'll be respected if not liked. And that's what it means to be a mentor.”  IV. Changing perceptions How does Tony assess his own relationship to self-doubt? “Everyone goes through imposter syndrome. Everyone does. We all have gone through it, I go through it. Because you know what, when you're doing stuff you've never done before, and you're changing the world, no one else has done it either. No one else has done it either. That means it's okay. 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." What are Tony's views on failure? “Now, there's taking stupid risks versus risk mitigation and taking calculated risks. But you should always be living on the edge of pushing yourself because that's where the growth is, that's where the change is happening." Does one learn more from success than from failure? "How we do and change the world is through the same method. We go do, and then we fail, and then we learn from that, and then we do again.” What does Tony mean when he says, "do, fail, learn." “Look, it's do, fail, learn; do, fail, learn. There's no such thing as learn and then you're able to do. No, no, no. When you really learn in life is after you've tried to do it." What is the right way for entrepreneurs to present their boldest of ambitions? "Look at Elon now. If he was pitching what he's doing now 15 years ago, people would go, No way! A few people, like Jurvetson and others, said, Yeah, sure, okay, great. But very few people would get behind that huge boldness." “So what they do is – and this is what I've had to do – they start and just pitch that simple ‘What's the next three to four years look like?’ and never tell anybody about the big picture. Because you scare most people off." How do investors need to change how they think about ambition and upside? 5.) Why does Tony believe the first trillionaire will originate from the climate change space? Why is the majority of plastics recycling total BS today? Why does Tony believe we need to fundamentally transform our economies? How do funding markets need to change to fund this structural reshaping of society?