This Is What Billionaires Regret Before Dying - Noah Kagan
Noah Kagan (guest), Chris Williamson (host)
In this episode of Modern Wisdom, featuring Noah Kagan and Chris Williamson, This Is What Billionaires Regret Before Dying - Noah Kagan explores billionaires’ Regrets, Real Wealth, And Starting Businesses Without Excuses Chris Williamson and Noah Kagan explore the psychology behind ambition, success, and fulfillment, using Noah’s experiences with billionaires, AppSumo, and his new book ‘Million Dollar Weekend’ as anchors.
Billionaires’ Regrets, Real Wealth, And Starting Businesses Without Excuses
Chris Williamson and Noah Kagan explore the psychology behind ambition, success, and fulfillment, using Noah’s experiences with billionaires, AppSumo, and his new book ‘Million Dollar Weekend’ as anchors.
They contrast obsessive perfectionism versus ‘move fast’ experimentation, emphasizing that most people quit too early and spread themselves too thin instead of going deep on one winning thing.
Noah shares patterns he’s seen in billionaires: they focus on one big market for decades, often at the cost of family and contentment, and many privately regret neglecting relationships.
The conversation closes on practical courage: shrinking fear through small “asks,” re-framing rejection, using coaches, and building a life that balances world‑class work with inner peace.
Key Takeaways
Play to your natural strengths instead of copying others’ styles.
Chris accepts that he’s slow and detail‑oriented rather than a ‘move fast, break things’ founder; by leaning into that, he wins “in the weeds” instead of trying to compete on speed he doesn’t naturally have.
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Most success comes from going deep on one thing for a long time.
Noah notes that every billionaire he’s worked with became rich from a single focus (e. ...
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Stick with what’s working and quit what isn’t—fast.
They argue people invert persistence: they cling to failing ideas for years but abandon promising ones too early. ...
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Protect motivation through the hardest, lowest‑reward early phase.
Drawing on Paul Graham, Chris points out that starting requires huge energy for minimal results; without support, celebrating small wins, and systems, you risk arriving at success with zero motivation left.
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Rejection and asking are trainable skills that unlock opportunity.
Noah’s ‘coffee challenge’ (ask for a 10% discount) and his DocuSign experiment show that practicing small, safe asks shrinks fear, normalizes ‘no,’ and directly leads to customers and revenue.
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Billionaires often regret sacrificing family and inner peace.
Noah recounts billionaires who spent 30+ years stressed and later admitted they missed their kids, marriages, and any sense of “enough,” underscoring that massive wealth doesn’t resolve inner emptiness.
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Use coaches and therapy to shorten learning curves and soften the journey.
Noah has spent over $1M on coaches (CEO, CFO, marketing, therapy) to address blind spots in business, emotions, and health—arguing you can literally buy others’ 10,000 hours instead of reinventing everything.
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Notable Quotes
“Perfectionism is procrastination masquerading as quality control.”
— Chris Williamson
“All the billionaires I’ve worked with got rich on one thing.”
— Noah Kagan
“I’m not here just to make so much money that I can have the nicest cemetery grave.”
— Noah Kagan
“If you would do this thing for free, you will win, because the person that loves walking will way outwalk the person who has to walk.”
— Chris Williamson
“The magic you are looking for is in the work you’re avoiding.”
— Chris Williamson
Questions Answered in This Episode
If most billionaires regret sacrificing family and peace, where is the true ‘enough’ point for wealth and ambition in my own life?
Chris Williamson and Noah Kagan explore the psychology behind ambition, success, and fulfillment, using Noah’s experiences with billionaires, AppSumo, and his new book ‘Million Dollar Weekend’ as anchors.
Get the full analysis with uListen AI
What is the one project, skill, or business I could commit to for 10–20 years instead of constantly starting over?
They contrast obsessive perfectionism versus ‘move fast’ experimentation, emphasizing that most people quit too early and spread themselves too thin instead of going deep on one winning thing.
Get the full analysis with uListen AI
Which small, scary ask could I make this week (a discount, a sale, a favor) to begin rewiring my relationship with rejection?
Noah shares patterns he’s seen in billionaires: they focus on one big market for decades, often at the cost of family and contentment, and many privately regret neglecting relationships.
Get the full analysis with uListen AI
Am I clinging to any projects that aren’t working while under‑investing in the few that clearly are?
The conversation closes on practical courage: shrinking fear through small “asks,” re-framing rejection, using coaches, and building a life that balances world‑class work with inner peace.
Get the full analysis with uListen AI
How could I use coaching, therapy, or outside expertise to collapse years of stumbling into months of focused progress—and what resistance do I feel to doing that?
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Transcript Preview
I was so impressed to see that you emailed me in 2019.
Yeah, tell me about that. You were reading the archive emails back.
It's just interesting to see who makes it, right? And, uh, I think I emailed you as Million Dollar Weekend was coming out. I was talking to the team and I was like, "Oh, there's a few shows I'd love to be on." And, and you were one of them. Uh, I think Stephanie reached out and we reached out and then it was like, "Yeah, it's gonna happen." I was like, "Oh, that's interesting." And I saw one of your clips about Success Bias, As The World Works. And I was like, "I just want to tell him I love his stuff." And I think that's such a thing that anyone can copy. Like, reach out to someone and just tell them that you've made an impact or that you like what they're doing. And so I, "Let me just search my Gmail." So I searched Chris Williamson in my Gmail, and it was in 2019, January, you said, "Hey, mate." That's how you British like-
Mm-hmm.
... you like to address us. And I... And you said, "Hey, I'd love for you to come on the show." And I just couldn't believe... And then what was even crazier, I was reading it to my girlfriend today. I said, "Hey, I'm busy with my, with AppSumo. Can you follow up in March?" You said, "No problem." You followed up in March. I said, "I'm busy in March." Can you follow up in two months?" You followed up every single time. And it's... You don't know who's really gonna make it, but it said a lot about your character that you kept following up, following up, and following up. And I, I always admire people that follow up.
Thank you.
So it's cool that we're, we're here ............................
I appreciate that. Yeah, man. It's come full circle. It's only, what, five years later or whatever-
(laughs)
... but finally, we find... I've g- I got you in the end, you motherfucker.
There, it happens, yes. (laughs)
I got you in the end. Um, no, yeah, I think... Look, there's a lot of disadvantages to being, uh, obsessive and compulsive, like, uh, even if it doesn't meet the medical criteria of, of that.
(laughs)
Um, there are a lot of disadvantages, like you, you, you see things and you don't let things go and it causes you to move slowly. Like, I find, um... And a lot of the people who also have an attention to detail that's probably over the top, um, will notice that they leave things on the table because they can't move as quickly as people who are a little bit more blase.
Mm-hmm.
You know, if you're able to just, like, move fast, break shit, like, that whole kind of, like, Silicon Valley SF thing, that's never been me. It's never, ever, ever been me. And I've kind of... I've come to terms with that now, and I've realized where my competitive advantage lies, and it's being thorough and, and paying attention to detail and winning in the weeds. And other people can win with velocity, but that's not the game. I, I, I would need to, I don't know, just permanently be on, like, MDMA or something if I was gonna do that.
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