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Taxes and Exits

Taxes and Exits

Hosted by Paul H. Graham

Episodes

80

Latest episode

Oct 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
October 21, 202629 min

Why Most Business Partnerships Fail and How to Avoid Being Next

In this episode, Ash Patel shares invaluable lessons from his extensive experience in business partnerships, real estate, and entrepreneurship. Discover how to find the right partners, draft effective agreements, and navigate the complexities of busine...

October 14, 202631 min

AI Risks Small Businesses Overlook: How to Avoid Costly Mistakes

In this insightful interview, Paul Graham and David Robinson explore the critical risks and strategic considerations for small and mid-sized businesses adopting AI technology. They discuss how to identify real problems versus symptoms, the importance o...

October 1, 202633 min

Unlocking $22.1m in Stalled Pipeline

In this episode, Jen Kelly shares how a company unlocked $22 million in pipeline by refining lead nurturing and sales strategies. Paul Graham discusses growth mindset, customer diversification, and effective marketing tactics for business success.Timel...

September 22, 202651 min

Why Doing Everything Yourself Cost $100 Million

Larry G. Dix II shares his transformative journey of self-awareness, the importance of delegation, accountability, and living intentionally to maximize success and fulfillment in business and life. Timeline 00:00 Introduction and the importance of self...

September 16, 202639 min

The Power of Fractional CFOs in Scaling Your Business

In this episode, Paul Graham and Richard Boyd discuss the critical role of financial management and fractional CFOs in scaling businesses from five to thirty million dollars. They explore real-world stories, misconceptions about CFOs, and how AI is tra...

September 10, 202632 min

The End of Manual Capital Raising

In this episode, Paul sits down with Elisabeth Bykoff ex-PwC, 10-year venture veteran, and founder of Boxsy, to break down why most founders start the fundraising process completely wrong, whether you actually need to raise at all, and how an AI COO pl...

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...

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