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The Investor's Guide To Joy

The Investor's Guide To Joy

Hosted by Paul H. Graham

Episodes

67

Latest episode

Jun 2026

Language

EN

About the show

“How do I create true freedom without trading time for money?” “What’s the playbook for passive income, tax-smart investing, and joyful living?” You're in the right room. Each week, you'll hear from elite investors, founders, and wealth strategists who’ve traded stress for stewardship—sharing practical moves to help you grow, give, and enjoy more. Hosted by Paul Graham—entrepreneur, capital raiser, and founder of Octane—who helps purpose-driven leaders scale to 7–9 figures with peace of mind, not pressure. Ready to build wealth that serves your life—not the other way around? Subscribe and start investing with clarity, conviction, and joy.

Listen to episodes

60 recent
June 16, 202619 min

How To Cut Your Database Operations Cost Without Laying Off A Single Person

One outage. One hour. $1.5 million in lost revenue. That's the reality for enterprise companies running fragmented databases across multiple clouds, tools, and teams with no single place to see, manage, or fix any of it. Janardhan, founder of DBaaS Now...

June 9, 202629 min

The $0 Fix That Turned a Bleeding STR Into a Cash-Flowing Machine (yeah, seriously)

You bought the short-term rental. You're paying 20% to a property manager. And somehow, you're still stressed, still losing money, and still getting a text at 2AM about a broken microwave. Taylor Jolly has managed short-term rentals across Texas and se...

June 2, 202630 min

Banks, Gold & Getting Out of the System Before It's Too Late

Marc Walton has lived through the dot-com boom, the 2008 crash, the crypto run of 2020, and a gold bull market that delivered 300% gains on a single miner, all while trading Forex for 15 years from a sun-soaked island in Portugal. In this episode, he a...

May 26, 202619 min

The $1M to $10M Sales Blueprint: How to Stop Being the Only Closer in Your Business

Michael Schiltz spent 14 years mastering sales including carrying a $12M quota at Dell before moving into consulting to help founders do the one thing most can't: step out of the sales seat and build a system that scales without them. In this episode, ...

May 20, 202630 min

Owning Multiple Businesses 1,000+ Miles Away

Steven Nunez left corporate after 10 years, put six figures into his first build, and now owns and operates multiple full-service laundry centers across Central and South Florida all managed remotely from New Jersey. In this episode, he breaks down the...

May 12, 202631 min

Why Your Startup Pitch is Failing (And What Investors Actually Bet On)

Joe Feminella, entrepreneur and founder of First Round on Me, gets raw about what it really takes to raise $5M+ across multiple company pivots, no Harvard degree required. In this episode, Joe breaks down how a single investor conversation changed ever...

May 5, 202623 min

Bridging the Gap: Aligning Education, Economic Development, and Industry

In this episode, host Paul Graham sits down with Curtis Clough, a seasoned educational leader and superintendent, to discuss the critical intersection of K-12 education, workforce development, and economic growth. Curtis shares his unique "trifecta" pe...

April 28, 202625 min

The People ROI: Why Great Leaders Put Humans Before KPIs

Is your leadership style adding or multiplying? In this episode, Paul Graham sits down with Tim 'Coach' Scholze, a seasoned leader who climbed from the mailroom to the executive suite, to discuss why most CEOs fail when they focus solely on the data. T...

April 22, 202625 min

How Founders Accidentally Lose Millions During Due Diligence

Are you building a billion-dollar company with a thousand-dollar mindset? In this episode, Paul Graham sits down with Eric Nghiem, founder of The Cashflow Doctor, to dissect the financial "hiccups" that sink tech startups during due diligence. Eric sha...

April 16, 202626 min

Using AI to Audit and Avoid Extra Cloud Spend

In this episode, Max from CloudGo.ai explains how companies bleed millions in cloud spend. Discover how to audit your environment to ensure your tech stack is ready for VC due diligence or a single engineer becoming a point of expensive failure. 00:25 ...

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