61: The Half-Trillion-Dollar Opportunity Between Venture Capital and Private Equity with Scott Ryan

Scott Ryan is a Managing Partner for Terra Rossa Investments—a family office and active investor that invests in fixed income, debt products, real estate, and later-stage tech.

Today, Scott shares his journey from working in tech sales to founding and exiting three companies (including an 8-figure exit) to running a fund in an asset class that’s “too late-stage for venture capitalism and too small for private equity.” 

Scott shares a complete breakdown of running and raising capital for his fund and the investor opportunity for accessing the half-trillion-dollar asset class. 

You’ll also hear Scott share a unique strategy for avoiding long-term capital gains tax, the biggest challenges in selling his companies, and various ways investors can access his market area with lower investment minimums.

Scott Ryan Inspiring Quotes

• “We’re risking a lot because we believe in the process.” – Scott Ryan

• “AT&T, Oracle, IBM, they don’t create a lot of their innovation. They acquire it. They buy it.” – Scott Ryan

• “Yield is what brings real estate investors and some other groups around to say, ‘Hey, this is kind of compelling to us.’” – Scott Ryan

✔️The half-a-trillion dollar opportunity between VC and PE.

✔️The model Scott used to land an 8-figure exit.

✔️Types of partners you can leverage when making an exit deal. 

✔️The key differences in how Scott’s fund operates compared with PE firms.

✔️Scott shares the toughest thing about selling his first company.

✔️The challenge Scott sees for CEOs who want to continue to accelerate—and how he solved it.

✔️A complete breakdown of the financial details for Scott’s Fund, including initial funding, investing, calls and distributions.

✔️Scott breaks down the various ways small businesses can raise money.

✔️One metric that can attract big real estate investors with $20-50B AUM.

✔️How Scott uses Special Purpose Vehicles (SPVs) to make investing in his fund more accessible.

✔️Understanding tax nuances with Qualified Small Business Stock (QSBS) to avoid paying federal capital gains on an exit.