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Taxes and Exits

Taxes and Exits

Hosted by Paul H. Graham

Episodes

75

Latest episode

Aug 2026

Language

EN

About the show

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 figures in value across his companies. As Chief Growth Officer at Stakeholders Family Office, he helps 7–8 figure business owners coordinate tax strategy, alternative investments, and exit planning under one roof, so nothing falls through the cracks before or after the transaction. If you're a business owner scaling toward a liquidity event, trying to protect what the sale just created, and unwilling to sacrifice your joy in the process, this show was built for you. Subscribe for free and join the live show to ask your questions directly. When you're ready to talk about what a fractional family office could do for your situation, start at investorsguidetojoy.beehiiv.com

Listen to episodes

60 recent
August 6, 202625 min

Before You Build a Family Office, Fix This First

JD Rockefeller invented the family office in 1882 because every advisor he had was working in a silo and nobody was talking to each other. Most business owners today have the exact same problem. Dale Montgomery oversees a virtual family office with 70+...

August 6, 202626 min

The Hidden Cost of Not Tracking Your Digital Assets

An advisor came to Perry Woodin and said his client had 50 crypto wallets. When they looked closer, they found 150. With dozens of digital assets across them that the client didn't even know existed. Perry Woodin is the co-founder of Node40, a digital ...

July 20, 202634 min

How To Add AI To Your Business Without Breaking Everything That Already Works

It's not a magic robot. It's an LLM call on a while loop. Mike Vanamburg has built AI agents for companies across industries — from cannabis dispensaries to bookkeeping firms to his own business — and the lesson he keeps learning is the same every time...

July 13, 202641 min

What $5M to $30M Scaling Actually Looks Like Behind the Scenes

He had a booming business in 2024. Great profit. Cash in the bank. Then he launched a new product, hired new employees, bought new vehicles and within a year had lost everything he'd saved and was calling banks to ask about hardship assistance. Richard...

July 6, 202640 min

The Biggest Mistakes of Investing in Real Estate

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 ...

July 1, 202639 min

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

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...

June 23, 202624 min

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

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 ...

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...

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