What do billion-dollar investors and donors actually care about?

It’s not your pitch deck.

It’s not your financial model.

And it’s definitely not your IRR slide.

In this episode of Commercially Speaking, we sit down with Greg Dugard, COO of Sator Grove Holdings, who previously helped raise over $5 billion during Notre Dame’s historic capital campaign.

Greg breaks down what he learned from raising billions, working with ultra-high-net-worth families, and now partnering with founders through permanent capital, a long-term investment approach that rejects forced exits, short-term incentives, and five-year flip cycles.

We explore:

• What investors actually look for before wiring money
• Why time horizons destroy more value than bad deals
• Permanent capital vs private equity and venture capital
• How misaligned incentives quietly ruin partnerships
• Why selling too early kills compounding
• The difference between IRR and long-term wealth creation
• How founders should evaluate partners before signing
• Why trust beats returns in the long run
• What “life’s work” really means for a founder

If you’re a founder, investor, or operator thinking about taking on capital, this conversation might save you years of regret.

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🎧 Learn more about Greg & Sator Grove: https://satorgrove.com

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Thanks to Our Sponsors

• 💰🏙️ CRE Investor Coach: No Guess Work, No Wasted Time — https://cre-investor-coach.mykajabi.com/a/2148133410/9YMWzNXy
• 🤖 Superpowers HQ – Need a CRE executive assistant? Get one here: superpowershq.com/commerciallyspeaking

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⏱️ YouTube Chapters (Keyword-Optimized)

00:00 – What Billion-Dollar Investors Really Want

Why numbers aren’t the point

04:10 – Raising $5B Without a Med School

How Notre Dame broke records

09:40 – Why Most Capital Destroys Value

The hidden cost of short time horizons

15:30 – What Permanent Capital Actually Means

No flips. No forced exits.

22:20 – Why Selling Too Early Is the Real Risk

The compounding everyone ignores

30:10 – IRR vs Multiple on Capital (MoIC)

Why IRR lies over long periods

38:40 – Incentives: The Invisible Hand

The tattoo founders should get

47:30 – Choosing the Right Capital Partner

Who you let around the table matters

55:50 – Trust, Talent, and Long-Term Thinking

How great companies are really built

01:05:30 – The Taylor Swift Story

Yes, this actually happened

01:10:40 – Advice for Founders Before Signing

What to know before taking money

📒Show Notes📒

Subscribe and listen to Commercially Speaking here:

Youtube:  @commerciallyspeaking 

Spotify: https://podcasters.spotify.com/pod/show/commerciallyspeaking

Apple: https://podcasts.apple.com/us/podcast/commercially-speaking/id1680750330

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iHeart Radio: https://www.iheart.com/podcast/269-commercially-speaking-112157161/

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Bo is a CCIM Instructor, co-founder of HearthStone Capital, and the owner and operator of Barron Commercial Group, servicing Western KY and its surrounding markets.

For all CRE inquiries, visit barroncommercial.com

Timmy is an actor, comedian, writer and host: @timmybarron https://youtu.be/ICoIAHSZvgA