Modern Wisdom
Modern Wisdom

What Are The Biggest Regrets Of The Super Rich? - Noah Kagan - #761

Noah Kagan is an entrepreneur, founder of AppSumo and a YouTuber. Does money make you happy? What about a lot of money? Like billions of dollars a lot of money. Noah has spent years around some of the richest people in the world and deconstructed some of their biggest regrets, thinking patterns and

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Episode Summary

Executive Summary: The conversation centers on the power of persistence, asking for help, and building businesses or media brands by playing to personal strengths. Both speakers argue that success comes from long-term focus on one thing, early validation, discomfort tolerance, and protecting motivation over time. They also explore the hidden costs of wealth, the importance of inner work, and how coaching, therapy, and self-awareness help sustain success without losing joy or balance.

Main Topics: Persistence and compounding over time (Priority: 5/5): The hosts stress that most meaningful results come from sticking with one path long enough for compounding to work. Early years are often flat, but returns accelerate later if you continue. Playing to personal strengths (Priority: 5/5): A major theme is that people should lean into their natural advantages—detail orientation, speed, asking, or consistency—instead of trying to imitate someone else’s style. The value of asking and doing non-scalable work (Priority: 5/5): Much of the discussion focuses on cold outreach, follow-ups, direct asks, and manual validation as the practical behaviors that kickstart businesses and media growth. Wealth, happiness, and hidden costs of success (Priority: 4/5): They contrast outward success with internal dissatisfaction, arguing that money and status solve some problems but can worsen others, especially family and emotional fulfillment. Therapy, coaching, and self-regulation (Priority: 4/5): Both speakers describe investing heavily in therapy and coaching to improve emotional control, leadership, and personal relationships, framing business as a vehicle for self-development. Fear, rejection, and inner resistance (Priority: 5/5): A recurring point is that fear of asking, rejection, and unrealized potential keeps people stuck, and small exposure exercises can reduce that fear. Brand-building and audience growth (Priority: 4/5): The transcript includes detailed tactics for growing a podcast, YouTube channel, and product launches, emphasizing consistency, audience trust, and one-core-offering focus.

Key Arguments: Long-term compounding beats short-term hustle: the show and businesses only became powerful after years of consistent effort. Trying to imitate a fast, high-velocity style is a mistake if your strength is detail, thoroughness, or relationship-building. Winning early validation matters; people should quickly test whether anyone actually wants what they are making before scaling. Non-scalable actions—manual messages, direct follow-ups, spreadsheet-driven outreach—are often the real engines of early traction. The best businesses are usually built in large and growing markets rather than around trends or solutions detached from real problems. The same traits that help people succeed—obsession, dissatisfaction, perfectionism—can become harmful once a business matures. Wealth does not automatically create happiness; many rich people trade family, peace of mind, and contentment for status and money. Internal validation is more sustainable than relying on external applause, especially once success starts to plateau or become routine. Facing the work you are avoiding is often the shortest route to growth in business, relationships, and self-worth. Coaching and therapy are rational investments because they accelerate learning, improve behavior, and help leaders avoid blind spots. Rejection is usually less painful than imagined, and practicing small asks can rewire someone’s relationship to fear. The goal is not just to become successful, but to stay happy and grounded while doing it.

Data Points: Podcast audience growth: ~500 million people a year - Noah describes the scale of the podcast's reach. Show growth lag: Flat for 3.5 years - The podcast had minimal growth for the first several years before compounding. Audience acquisition last year: 85% of the audience found the show last year - A large share of listeners came relatively late in the show's life. Monthly subscriber growth: More subscribers in one month than in the first 3.5 years combined - Illustrates compounding after a slow start. Rogan scale comparison: 26x bigger by followers alone - The show is compared to Joe Rogan’s audience size. AppSumo revenue: Almost $100 million a year - Used as an example of long-term business compounding. Early launch team outreach: 1,000 people - Noah used a spreadsheet of a thousand contacts for the book launch team. WhatsApp broadcast contacts: 2,500 contacts - Used in the early podcast launch through club-promo contacts. Broadcast list size: 50-person lists - WhatsApp chunked contacts into 50-person broadcast groups. Podcast launch timing: About 4-6 months - Time from idea to launch/branding decision in 2017-2018. Million Dollar Weekend launch team: 1,000 lines in a spreadsheet - Used to organize outreach and reviews for the book. Book validation revenue: $3,000 in 24 hours - Direct customer deposits from outreach for the DocuSign alternative idea. Coach spending: At least $1 million - Collective spending on coaches by Noah and his team. Business coach cost: $10,000 a day - An expensive coaching engagement Noah described as unhelpful. Patrón sale: $3.5 billion - John Paul DeJoria’s tequila business exit is cited as a model of one-thing focus. Kinko’s sale: $2.4 billion - Paul Orfalea’s copier business example of decades-long focus. Audience validation example: 300 views on first YouTube video - Noah describes the early content validation of his channel. Mature show performance: 200,000x what it was six years ago - A hyperbolic comparison to show how returns changed over time. Podcasting market growth: 20% to 30% per year - Chris mentions the category’s expansion as a tailwind.

Pivotal Quotes: "The tools that got you here won't get you there." — Chris Williamson: Discussing how early-stage skills can become limiting later. "The magic you are looking for is in the work you're avoiding." — Noah Kagan: Explaining that the hardest avoided tasks often unlock growth. "It is easier to achieve our material desires than to renounce them." — Chris Williamson: On why external success is easier to chase than internal contentment.

Implications: For creators and founders, the lesson is to start fast, validate early, then commit long-term while protecting mental health. Success scales best when paired with self-awareness, coaching, and a willingness to ask, follow up, and endure rejection.

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Chris Williamson in long-form conversation with the world's most interesting people - psychologists, scientists, authors, comedians and entrepreneurs - on life, science, health, fitness, business and philosophy.

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