Business Book Club – Details, episodes & analysis

Most entrepreneurs are stuck in a race they never signed up for, chasing a version of success that leaves them burnt out and unfulfilled. In this episode, Caitlin Rozario, founder of Interlude, deconstructs the wisdom of The Almanack of Naval Ravikant. Caitlin shares her raw journey of shutting down her software business to pivot toward her "zone of genius”—revealing that the most successful people usually aren't the ones working the hardest, but the ones who have mastered the art of being themselves.

00:00 Introducing The Almanack of Naval Ravikant by Eric Jorgenson.

01:54 The power of deep specific knowledge: what is it & how you can “find” yours

03:20 Identifying "Play" vs. "Work": How to do the thing that feel like play to you but will look like work to others

04:25 The Ikigai Pivot: Caitlin describes using the Japanese concept of Ikigai—the cross-section of what you love, what you're good at, what the world needs, and what you can be paid for—to finalize her decision to shut down her app and move into workshops

08:15 Top tip - The "Smile File": How to combat the entrepreneurial "negativity bias”

09:19 Escaping Competition Through Authenticity: "If you are fundamentally building and marketing something that’s an extension of what you are, no one can compete with you on that."

18:02 Accepting you are a rat in a race: the best-case scenario is simply being a rat who is mindful enough to look up at the clouds once in a while

21:50 Defining Your Own Success: Why you must plan your career around your lifestyle rather than the other way around

📚The Almanack of Naval Ravikant by Eric Jorgenson

Cal Newport’s Deep Life Stack

The Ikigai Diagnostic Tool

Naval’s "How to Get Rich" (The 3-Hour Podcast)

1. Caitlin Rozario, Founder of Interlude
2. Interlude: The Anti-Toxic Productivity Bootcamp

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I ask founders: Which book has had the biggest impact on your business, or life?

We speak about 3 lessons from the book - and crucially - what the real impact has been for them.

Most of my guests are successful entrepreneurs and have read hundreds of books. Im asking for the one that's have the most impact. Then the most valuable learnings from the most valuable book.

Listen to absorb the most valuable lessons - from 50 books a year - in about 30 minutes a week.

If you’re a busy founder, pick an episode and get stuck in now. Or if you want to know more about me, give this trailer a listen.

Kim Scott is a heavyweight in the tech world, having coached CEOs at companies like Dropbox and Twitter and led teams at Google and Apple University.

In this episode, Ramsey Marwan, co-founder of MG Relations, unpacks how Radical Candor became a turning point in his career. He explains why "ruinous empathy" is the most dangerous trap for nice founders and why the best managers are the ones willing to have the conversations that sting in the moment but help in the long run.

00:00 Introducing Radical Candor by Kim Scott.

01:54 To scale, you must let go: Why jumping in to "fix" things yourself destroys trust and prevents your team from growing.

06:44 Don't just keep it professional, actually care: You cannot run a team without trust. Treat your employees like human beings, not robots or resources.

11:15 Mastering Silence: Why you need to "shut up" during one-on-ones to let the real issues surface.

15:40 – The Trap of Ruinous Empathy: Ramsey breaks down the famous 4-quadrant diagram (Caring Personally vs. Challenging Directly) and explains why being "nice" can actually hurt your team's reputation.

16:03 The 4 Quadrants Defined: Understanding the difference between Radical Candor, Obnoxious Aggression, Manipulative Insincerity, and Ruinous Empathy.

17:14 The "Zipper" Analogy: A simple way to understand how to apply the quadrants in real life.

22:00 Real-World Application: Ramsey shares a story of confronting a colleague who spoke poorly of a team member in a meeting.

📚Radical Candor by Kim Scott

1. The Radical Candor Matrix: The 4-quadrant framework (Care Personally + Challenge Directly)
2. FX Digital (Ramsey’s previous startup)

1. Ramsey Marwan, Co-Founder of MG Relations

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Unlike most business books, How to Get Rich doesn't sugarcoat the sacrifices, the ego, or the sheer obsession required to build wealth.

The late Felix Dennis—founder of Maxim magazine was one of Britain's richest self-made men. As he wrote How to Get Rich, he sat on a goldmine of hard-won lessons. He explains how wealth is really made and why most people will never do what it takes.

Joining me to unpack this unfiltered playbook is Alex Bodini, CEO and co-founder of Spin Group. Alex has built a global social media agency of 80+ people while launching multiple ventures like Acid Running and Janji Europe. For Alex, it’s never been about perfection but about momentum, learning, and loving the ride.

00:00 – Introducing How to Get Rich by Felix Dennis.

02:40 – Don't Listen to Jeremiahs: Why "wantrepreneurs" project their fears onto you.

06:40 – The Information Diet

09:23 – "Overhead Walks on Two Legs”: The dangerous trap of hiring too fast and buying fancy offices.

12:28 – Rules of Thumb: The "7% Rule”.

13:56 – Diversify Your Baskets (After Success):

15:21 – The Regret Minimization Framework: How to make decisions today that your 80-year-old self will thank you for.

📚How to Get Rich by Felix Dennis

1. Spin Group: Alex’s Social Media Agency
2. Acid Running: One of Alex’s side ventures
3. Janji Europe: Another venture in Alex’s portfolio

Alex Bodini, Co-Founder of Spin Group

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If there is a Bible for Silicon Valley CEOs, it is High Output Management by Andy Grove.

Though this isn't just a book—it is the operating system that helped Intel scale to become the world's largest semiconductor manufacturer. It is the framework used by leaders at Apple, Facebook, and Google. But does a book written about a chip manufacturer in the 80s actually apply to modern creative businesses?

To find out, I’m sitting down with my co-founder at Fascinate Productions, Rich Willan. Rich is obsessive about systems. He turned our creative workflows into a well-oiled machine, and he credits this book with changing how he leads.

1. 00:00 – Introducing High Output Management by Andy Grove.
2. 01:48 – The Breakfast Factory: Why everything—even creative work—is a process.
3. 05:39 – The "Podcast OS": Rich reveals the system he built to produce the Zoe Science & Nutrition show
4. 10:05 – Systemizing Personal Life: How Rich uses SOPs (Standard Operating Procedures) to book holidays and avoid "desert madness."
5. 11:32 – Task Relevant Maturity (TRM): The definitive guide on when to micromanage vs. when to delegate.
6. 16:56 – Leverage: How to distinguish between $10 tasks and $10,000 tasks.
7. 18:19 – Negative Leverage: Why being late to a meeting destroys more value than you think.
8. 19:37 – The Calendar Audit: Andy Grove’s method for color-coding your schedule to maximize output.

📚 High Output Management by Andy Grove

1. Tim Ferriss & Tobias Lütke Podcast: The episode where Rich first discovered the book.
2. Zoe Science & Nutrition: The podcast Rich produces using his "Podcast OS."

Rich Willan, Co-Founder of Fascinate Productions

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Joe Dispenza is a New York Times bestseller known for bridging the gap between neuroscience, epigenetics, and human potential. He challenges the idea that we are hardwired to be a certain way for the rest of our lives.

In this episode, Annika Lundström, former Youth Olympian and founder of the medtech startup Reminded, explains how she used the principles of this book to transition from high-level sports to the high-stakes world of startups. She breaks down the science of "neuroplasticity" and why your internal dialogue is actually the architect of your business outcomes.

00:00 Introducing Breaking the Habit of Being Yourself by Joe Dispenza.

02:14 Neuroplasticity 101: "To change your life, change your brain." Annika explains how to utilize awareness to rewire your mind.

03:20 Auditing your Inner Dialogue: Why the most important conversation you have is the one with yourself.

06:51 The "Future Anxiety" Trap: Sam shares a story about rugby legend Johnny Wilkinson to illustrate how high-performers struggle to live in the moment.

09:44 The 15,000 Euro Pitch: How Annika used "presence" to win the Google Pitching Competition in Helsinki.

11:02 Radical Responsibility: "Your thoughts are the architects of your destiny." Why you must stop blaming external circumstances for startup setbacks.

13:02 Pivoting based on feedback: How to detach your ego from your idea during fundraising.

16:46 Reminded: Annika’s mission to revolutionize stress hormone detection.

📚Breaking the Habit of Being Yourself by Joe Dispenza

1. Reminded -Annika’s MedTech startup.
2. The "Future Anxiety" Case Study: Jonny Wilkinson’s Mental Health Journey
3. The Power of Obsession: Mr. Beast on the Joe Rogan Experience

1. Annika Lundström, Founder of Reminded

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Do you know anything about James Couzens or Roy Disney? Probably not. But you know their partners: Henry Ford and Walt Disney.

Walt Disney dreamed up the characters; Roy made the numbers work. Henry Ford revolutionized the car industry; James Couzens implemented the systems to scale it.

This is the core concept of Rocket Fuel: The relationship between a Visionary (the dreamer) and an Integrator (the executor). When this duo works, it is rocket fuel for a business. When it doesn’t, it’s chaos.

Joining me to unpack this is Jodie Imam, Co-founder and CEO of Tractor Ventures. Jodie explains how reading this book saved her working relationship with her co-founder, why they changed their job titles because of it, and how implementing the "Level 10 Meeting" completely transformed their team's culture and performance.

00:00 – Introducing Rocket Fuel and the concept of the Visionary/Integrator duo.

02:28 – Know Your Strengths: Why Jodie and her co-founder were stepping on each other's toes until they realized one was a Visionary and one was an Integrator.

04:44 – The Visionary/Integrator Test: How taking the official assessment brought clarity to their roles.

05:59 – Changing Titles: Why Jodie became "CEO" and her co-founder became "Head of Capital" to reflect their actual zones of genius—and why the team applauded the move.

07:43 – Structure Creates Flexibility (The 90-Day Scorecard): How giving every employee a single key metric enabled a 4-day workweek and flexible hours without sacrificing performance.

13:14 – The Level 10 Meeting: The 90-minute weekly meeting agenda that builds trust and solves problems before they hit the P&L.

16:12 – Rating the Meeting: Why every meeting must end with a rating out of 10 (and why you aren't allowed to choose "7").

22:16 – Tractor Ventures: Jodie explains their unique "non-dilutive" funding model for founders who want to build "tractors," not just "rockets."

📚 Rocket Fuel by Gino Wickman & Mark C. Winters

1. Tractor Ventures: Jodie’s alternative funding firm for founders.
2. Visionary/Integrator Assessment: The official test mentioned in the book.
3. EOS (Entrepreneurial Operating System): The broader system Rocket Fuel is part of.

Jodie Imam, Co-Founder & CEO of Tractor Ventures

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Most founders treat business decisions like chess, assuming that if they make the right move, they'll get the right outcome. But business isn't chess; it's poker.

You can make the perfect decision and still lose. You can make a terrible decision and get lucky.

Joining me to unpack this superb book is Jordan Staab, CEO of BetterFinances.org. Jordan is a serial entrepreneur who has raised over $200 million for VCs and led ventures worth over $30 million.

In this episode, Jordan explains how to separate your results from your decision quality, why saying "I'm 100% sure" is destroying your strategy, and how to build a truth-seeking inner circle to vet your bets.

00:00 – Thinking in Bets - why business is like poker, not chess

02:13 – Separate Outcome from Decision: Why a good outcome doesn't mean you made a good decision (and vice versa).

04:20 – The 50/80 Rule: How much data do you need before acting? Jordan explains his framework for balancing speed vs. confidence.

05:46 – The "iPhone Fingerprint" Analogy: Why you never have perfect information and how to gather just enough data to map the problem.

06:40 – Think in Probabilities, Not Absolutes: Jordan shares the "80% Question" he asks his team when creating financial projections.

09:24 – Climbing the Wrong Mountain: How to use decision trees to avoid backing your business into a corner.

11:27 – Standardize Your Decision Process: Why a problem well-defined is half-solved, and how to create a simple template for evaluating new ideas.

14:39 – Resulting is a Trap: The danger of judging the quality of a decision solely by its outcome (e.g., winning with a 7-2 offsuit in poker).

19:17 – The "Weddings & Funerals" Knowledge Gap: Why you need a truth-seeking inner circle to sanity-check your decisions in areas where you lack expertise.

📚 Thinking in Bets by Annie Duke

1. BetterFinances.org: Jordan’s financial literacy platform.
2. Amazon’s PR/FAQ: A famous example of a standardized decision-making document.

Jordan Staab, CEO of BetterFinances.org

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Who is Charlie Munger? Warren Buffett called him "our generation's Benjamin Franklin." Bill Gates hailed him as "one of the sharpest minds in business."

As Buffett's right hand at Berkshire Hathaway for 45 years, Munger helped achieve staggering 19.8% annual returns—double what the S&P 500 achieved in the same period.

In this episode, we dive into his legacy: Poor Charlie's Almanack.

Joining me is Alex Melia, founder of Swoosh English, to unpack the wit and wisdom of the man who popularized "mental models" and the art of "sit on your ass investing."

We discuss why patience is the ultimate competitive advantage, how to avoid "charismatic" fraudsters, and why the best way to get what you want in life is to deserve what you want.

00:00 – Introducing Charlie Munger and his impact on modern investing.

02:53 – Patience + Discipline = Success: Why the big money is not in the buying and selling, but in the waiting.

03:43 – "Sit On Your Ass Investing": Alex explains how Munger’s contrarian approach helps him weather business storms (like losing US contracts overnight).

06:57 – The Crypto Trap: Alex shares his personal story of ignoring Munger’s advice, following the herd into crypto, and learning a hard lesson about "fads."

10:41 – Be a Lifelong Learner: Why Munger, at age 99, was still the most curious person in the room (and why he asked more questions than he answered).

14:35 – The Multidisciplinary Approach: How reading outside your field (e.g., Range) gives you a competitive edge.

17:27 – Reputation & Trust: "It takes 20 years to build a reputation and five minutes to ruin it."

20:15 – The Red Flag Story: Alex reveals how he lost a fortune to a "charismatic" partner because he ignored the red flags of integrity.

📚 Poor Charlie's Almanack by Charlie Munger

1. Stripe Press Edition: The accessible, beautifully designed edition Alex recommends over the vintage copies.
2. Range by David Epstein: The perfect companion read for applying the "Generalist" strategy.
3. Berkshire Hathaway Shareholder Letters: Decades of free wisdom and the raw data for "sit on your ass investing."
4. Swoosh English: Alex's platform helping medical professionals pass high-stakes English exams.

Alex Melia, Founder of Swoosh English

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Even smart, well-funded executive teams fail.

Patrick Lencioni's masterpiece, The 5 Dysfunctions of a Team, exposes the silent killers of company growth and provides a practical framework to turn a group of capable individuals into a truly cohesive unit.

Joining me to unpack this framework is Alisa Cohn, an award-winning executive coach who was named the #1 Startup Coach in the world and has worked with C-suites at Venmo, Etsy, Microsoft, and Google.

Today, Alisa breaks down why your department is not your most important team, how to build vulnerability-based trust, and why self-awareness is the ultimate cheat code for leadership.

00:00 – Introducing The 5 Dysfunctions of a Team and the silent killers of company growth.

02:00 – The 5 Dysfunctions Framework: Alisa breaks down the hierarchy of team success: Trust drives Conflict, Conflict drives Commitment, Commitment drives Accountability, and Accountability drives Results. You cannot skip a step.

04:37 – Diagnosing Your Team: Why a lack of accountability is often just a symptom of a team that hasn't learned how to have productive conflict.

07:11 – The "First Team" Concept: Why the CMO's most important team is not the marketing department. It is the executive team.

09:20 – The Cost of Loyalty: How prioritizing your specific department over the executive team leads directly to toxic politics, silos, and blame.

14:24 – Self-Awareness as a Cheat Code: Why managing your ego and acting in service of the company is the hardest—but most necessary—leadership skill.

16:03 – The "Working With Me" Document: How creating a 1-to-2 page personal operating manual builds vulnerability-based trust.

16:59 – The 360 Feedback Loop: How to gather actionable behavioral feedback from the people above you, below you, and beside you.

📚The 5 Dysfunctions of a Team by Patrick Lencioni

1. From Start-up to Grown-up: Alisa Cohn's book, featuring 14 specific scripts to help you navigate delicate and difficult conversations.
2. The "Working With Me" Document: Atlassian's excellent free template and guide for creating a personal user manual.
3. The 360 Feedback Model: A comprehensive breakdown of how to run these reviews from the Center for Creative Leadership.

Alisa Cohn, Executive Coach & Author

Podcast & Book: From Start-up to Grown-up

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