Paul H. Graham

The Investor's Guide To Joy

Business EN ↓ 71 episodes

Keep More of What You Built. Live a Life Worth Having. Without Sacrificing Your Joy. This is the podcast for 7–8 figure business owners who are approaching, or have already had, an exit, and don't want to hand half of it to the IRS.Every week, you'll hear from founders, operators, and wealth strategists who've navigated the exit, the tax bill, and the harder question on the other side: now what? Hosted by Paul H. Graham, a 3x founder, co-author with Kevin Harrington (the Original Shark from Shark Tank), and author of The Entrepreneur's Tax Strategy. Paul has built, sold, and driven over nine f...

Author

Paul H. Graham

Category

Business

Latest episode

Jul 6, 2026

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Episodes

The Biggest Mistakes of Investing in Real Estate 06.07.2026

Most business owners invest in real estate the same way they run their business in the early days doing everything themselves, trusting their gut, and skipping the team that would actually get them to scale. Matthew Owens is a CPA who quit his firm in ...

Don’t Invest in Oil And Gas Until You Listen to This - A Guide to Oil And Gas investments 01.07.2026

People spend three to five years saving $100,000 then lose it in three to five months chasing the wrong oil and gas deal. Courtney has personally invested in over 100 wells and manages a portfolio of nearly 100 more, and she's seen it all: dry holes, f...

Why Traditional Business Rules are Dead: An AI Survival Guide for Executives 23.06.2026

AI isn't a search engine. It's not Google. And the executives treating it like one are missing the entire shift. Dov Levin works with executives and small-to-medium businesses to implement AI the right way starting with mindset, not the most expensive ...

How To Cut Your Database Operations Cost Without Laying Off A Single Person 16.06.2026

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...

The $0 Fix That Turned a Bleeding STR Into a Cash-Flowing Machine (yeah, seriously) 09.06.2026

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...

Banks, Gold & Getting Out of the System Before It's Too Late 02.06.2026

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...

The $1M to $10M Sales Blueprint: How to Stop Being the Only Closer in Your Business 26.05.2026

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, ...

Owning Multiple Businesses 1,000+ Miles Away 20.05.2026

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...

Why Your Startup Pitch is Failing (And What Investors Actually Bet On) 12.05.2026

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...

Bridging the Gap: Aligning Education, Economic Development, and Industry 05.05.2026

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...

The People ROI: Why Great Leaders Put Humans Before KPIs 28.04.2026

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...

How Founders Accidentally Lose Millions During Due Diligence 22.04.2026

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...

Using AI to Audit and Avoid Extra Cloud Spend 16.04.2026

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 ...

The Relaunch: Why I Paused the Podcast 14.04.2026

In this relaunch episode, I share why I paused the show for nine months to shift from "making noise" to creating real transformation. Discover how to grow your net worth without losing your identity or your family, as you transition from a moneymaker t...

What Every Business Owner Must Know About the 10% Equity Rule Starting June 1st 23.05.2025

In this episode of The Investor’s Guide to Joy, Paul Graham sits down with business strategist Jimmy Rios to unpack major SBA rule changes coming June 1, 2025, and what they mean for business owners looking to sell, scale, or bulletproof their companie...

The Truth and Timeline Behind DIY Cost Cutting for Business Owners 22.05.2025

In this episode of The Investor’s Guide to Joy, Paul Graham sits down with cost-reduction expert Shawn Stratton to uncover how business owners can save thousands without sacrificing service quality. From telecom audits to waste management, Shawn breaks...

Cut 28% of Your Business Expenses 20.05.2025

In this episode of The Investor’s Guide to Joy, host Paul Graham sits down with Shawn Stratton of Schooley Mitchell to uncover how businesses can boost profitability by slashing hidden operating costs without sacrificing service. From waste removal to ...

Never Fail a 1031 Exchange with this Method 07.05.2025

In this episode of The Investor’s Guide to Joy, Paul Graham welcomes Trevor LaParl, to explore the power of the 1031 Exchange. Trevor breaks down how investors can legally defer capital gains taxes, shares real-life success stories, and explains how to...

Commercial Office Building Changed Everything 05.05.2025

In this episode of The Investor’s Guide to Joy, Matt Drouin shares how he broke away from the grind of chasing money to build a life and business rooted in purpose, community, and joy. Tune in to hear his journey from burnout to breakthrough and how re...

Save 40-50% of Your Business Overhead 02.05.2025

Discover how seven-figure entrepreneurs are cutting up to 50% in operational costs and scaling smarter with AI in this game-changing episode featuring Devan Dillard. From replacing entire departments with intelligent agents to optimizing workflows, mar...

Double Your Company with These AI Systems 30.04.2025

In this episode of The Investor's Guide to Joy, Paul Graham sits down with AI strategist Devan Dillard to explore how six-figure business owners can leverage AI to scale smarter, not harder. From automating content creation and lead nurturing to using ...

What I Learned From Buying Multiple Small Businesses 28.04.2025

In this insightful episode of The Investor’s Guide to Joy, Jay Bourgana seasoned entrepreneur and GoBundance member, shares powerful strategies for buying and scaling service-based businesses. From fire extinguisher compliance services to niche landsca...

Helping Business Owners Create More Lifestyle Freedom 21.04.2025

In this solo episode of The Investor's Guide to Joy, host Paul Graham unveils a powerful new direction for the podcast focusing on helping business owners scale without burnout, exit with clarity, and build lasting wealth. Drawing from his own journey ...

Never pay Taxes On the Sale of Your Business 17.04.2025

Paul Graham and Trevor LaParl of Q1031.com discuss how the 537 Installment Sale Trust (IST) can serve as a powerful alternative or backup to 1031 exchanges, which often fail, leading to unexpected tax bills. Trevor explains how the IST allows investors...

How Dirt Can Turn Into Millions? 09.04.2025

In this episode of the Investor's Guide to Joy, we dive into the wild, gritty world of land development with Greg Farricielli a real estate wizard who’s turned empty lots into over $100 million in sales. Picture this: a guy who looks at a patch of dirt...

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