Few journeys in real estate are as inspiring as Glenn Yaney’s. On a recent episode of “Raising Private Money” with Jay Conner, Glenn shared the inside scoop on how he went from waiting tables at Red Lobster to becoming the co-founder and COO of Vertical Equity Partners, raising over $14 million in private capital. Glenn’s story is proof that where you start doesn’t determine where you end up—and that the right mindset, strategies, and relationships can change your life.

Finding the Turning Point

Glenn didn’t come from money, connections, or a prestigious background. In the words of Jay Conner, Glenn’s leap “from serving tables at Red Lobster to raising millions in private money” is, frankly, wild. So how did Glenn make the switch from restaurant shifts to real estate investments?

It all started with immersion. Glenn began working for a REIT (Real Estate Investment Trust), spending his days off shadowing real estate operators. “I watched what they do,” Glenn shared, “and I learned that those guys who were most successful were the ones who figured out how to buy real estate without the banks.” This key insight set Glenn on the path to financial independence.

The First Steps: Liquidity and Income-Producing Assets

Initially, Glenn made the same mistake many do: pouring money into retirement accounts like his 401 (k) and IRAs, making himself illiquid. The real shift came when he realized, “I needed to become more liquid and buy income-producing assets.” Within a year of refocusing his investments, Glenn achieved financial independence—thanks to just a couple of smart deals.

His first deal came from a local real estate investor with a three-unit mobile home park. Glenn looked up to this investor, and when he made an offer on the property, the only way the deal worked was if the seller became the lender. The terms were set by the seller, and Glenn agreed; just like that, he had his first private loan. Similarly, he bought a nine-unit mobile home park from the same investor, solidifying his footing in the industry.

Mindset Shifts and Overcoming Fear

Glenn admits those initial deals were nerve-wracking. “You start to realize that you’re actually going to make a little bit of money other than your W2,” he recalls. For years, Glenn studied real estate and investing before he ever made money. The breakthrough came not from saving more, but from finding down payment money outside his own funds—by leveraging other people’s money.

Scaling Up and Building Trust

It wasn’t long before Glenn started scaling his business. “Raising $14 million hasn’t happened by accident,” Jay noted. Glenn’s process is systematic and built on relationships. After each deal, Glenn would talk about it with others, demonstrating experience and building credibility. His secret? Consistent communication.

“I generally call [my investors] once a quarter at least to check in, see how they’re doing personally. They either have a referral, more money to invest, or questions about their investment. And by the end of the conversation, you know what you need to do better in the future.” Glenn also relies on solid software and a strong brand to make things easy for investors.

Honesty, Transparency, and Consistency

So what turns a one-time lender into a repeat investor? “Consistency and being very honest,” says Glenn. Investors know that in real estate, things can go wrong. But if you keep them informed—especially during rough patches—they’re more likely to trust you with more capital in the future.

Glenn shared the story of a mobile home park that went eight feet underwater during Hurricane Helene. “We had to communicate with the lender. It’s not like you could tell them the park was fine.” Through honest updates and transparency, Glenn maintained the relationship even through zero-revenue periods.

Structure and Win-Win Deals

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