What Billion-Dollar Investors Actually Look For (It’s Not Your Numbers) | Greg Dugard

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Recorded10 Feb 2026

Publisheranchor.fm ↗

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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 Seder 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 moneyWhy time horizons destroy more value than bad dealsPermanent capital vs private equity and venture capitalHow misaligned incentives quietly ruin partnershipsWhy selling too early kills compoundingThe difference between IRR and long-term wealth creationHow founders should evaluate partners before signingWhy trust beats returns in the long runWhat “life’s work” really means for a founderIf you’re a founder, investor, or operator thinking about taking on capital, this conversation might save you years of regret.🎧 Learn more about Greg & Seder Grove:https://sedergrove.comThanks 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📺 Subscribe for more conversations about real estate, investing, leadership, and building things that last.And Barbara Corcoran… permanent capital only. We’re ready.00:00 – What Billion-Dollar Investors Really WantWhy numbers aren’t the point04:10 – Raising $5B Without a Med SchoolHow Notre Dame broke records09:40 – Why Most Capital Destroys ValueThe hidden cost of short time horizons15:30 – What Permanent Capital Actually MeansNo flips. No forced exits.22:20 – Why Selling Too Early Is the Real RiskThe compounding everyone ignores30:10 – IRR vs Multiple on Capital (MoIC)Why IRR lies over long periods38:40 – Incentives: The Invisible HandThe tattoo founders should get47:30 – Choosing the Right Capital PartnerWho you let around the table matters55:50 – Trust, Talent, and Long-Term ThinkingHow great companies are really built01:05:30 – The Taylor Swift StoryYes, this actually happened01:10:40 – Advice for Founders Before SigningWhat to know before taking money⏱️ YouTube Chapters (Keyword-Optimized)

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