How to Invest After Selling a Business (Without Losing It All) with Ben Fraser of Aspen Funds

Beyond 8 Figures

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You built the business. You cashed out. Now what?

Most founders think they need to “reinvest everything” or go chase the next big thing. But in this episode of Beyond 8 Figures, I sit down with Ben Fraser of Aspen Funds to break down how to invest after selling a business — the right way.

Ben’s been inside this game since the last recession. He watched his father build Aspen Funds from scratch after the 2008 crash, and he’s since helped scale it into a multi-million-dollar platform that helps entrepreneurs invest passively (and intelligently).

We talk about why entrepreneurs make terrible investors, how billionaires actually diversify, and the overlooked tax strategy that could save you six figures. If you’re still betting everything on your business — or worse, sitting on cash and hoping for the best — this episode will shift your mindset.

Guest Introduction:
Ben Fraser is the Chief Investment Officer at Aspen Funds and co-host of the Invest Like a Billionaire podcast, where he helps high-performing entrepreneurs grow and protect their wealth through smarter, passive investments. With a background in commercial lending and institutional asset management, Ben has overseen $125M+ in real estate and business loans. Today, he specializes in guiding business owners toward alternative investment strategies that prioritize stability, cash flow, and long-term growth—without adding complexity to their lives.

Key Takeaways & Timestamps:

[05:37] The One-Liner That Changes Everything – “Wealth is created through concentration, but preserved through diversification.”
[06:38] How Billionaires Really Diversify – Ben reveals the Tiger 21 portfolio breakdown and how to use it.
[14:35] Unlocking Tax Loopholes Most Entrepreneurs Miss – What happens when your spouse qualifies as a real estate professional.
[15:36] Why One Founder Quit a 6-Figure Job to Save More – Ben shares a story that’ll make you rethink W-2s.
[19:47] Where the Smart Money Is Moving in 2025 – Ben’s macro-driven view of real estate (and what KKR just did).

The next big move in your business might start with a conversation.
If you’ve been thinking about leveling up, shifting directions, or preparing for a future exit, A.J. offers strategic support for entrepreneurs at a crossroads. No pitch—just a chance to explore what’s possible.

👉 Start here

Episode Highlights:

Don’t just reinvest everything into your business — you’re exposed.
Real diversification starts when you stop chasing control.
Use tax law to your advantage (especially with a strategic spouse).
Billionaires don’t try to time the market — they plan across decades.

Key Quotes:

“Wealth is created through concentration. But it’s preserved through diversification.”
“Entrepreneurs make terrible investors… because we’re wired to take risk, not preserve what we’ve built.
“You don’t need to earn more. You need to invest smarter.”

Resources & Links:

Connect with Ben Fraser:

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