Discipline, Speed, and Community: Wendell Butler’s Rules for Real Estate Investing

What separates those who dream about raising real money in real estate from those who actually do it? According to Wendell Butler, a former military officer who went on to found Hammerhead Capital and Flip Fuel Lending, it’s not complicated spreadsheets or pitch decks. In reality, it comes down to discipline, speed, and crystal-clear communication.

Laying the Foundation: From the Military to Real Estate

Wendell’s journey didn’t start in real estate—he began as a military officer, where discipline became second nature. He later transitioned to a loan officer role, gaining firsthand experience in the world of lending and underwriting. That dual background proved invaluable, allowing him to understand deals from both the lender’s and the investor’s perspectives.

But how did Wendell Butler make his first step into raising private money? It wasn’t about flashy presentations or aggressive sales pitches. Instead, he focused on building a reliable track record—executing on two simple deals, living in and flipping homes using his knowledge as a loan officer. “It was less about what I said and more about what I did,” he recalls. Showing proof of concept and genuine results was enough to inspire confidence in his earliest private investors—even when those deals were relatively small.

The Power of Simple, Honest Communication

One of the biggest takeaways from Wendell Butler’s interview with Jay Conner is the importance of keeping things simple. For new investors, the temptation to use industry jargon can be strong, but as Jay Conner points out, “A confused mind does not make a decision. Actually, they do—it’s called no.”

Instead, Wendell started conversations with people in his closest circles—family and friends—breaking his process down in plain language. He described what he had done, how it worked, and what kind of returns they could expect, bypassing complicated terms like “equity splits” or “GP/LP shares.” By making the opportunity easy to understand, he won early buy-in and trust, leading to soft commitments before he even had deals in hand.

Discipline as a Competitive Edge

Wendell Butler’s military background instilled an unwavering discipline, which became his edge in investing. That discipline wasn’t just about executing deals—it also translated into always doing what he said he’d do, especially when it came to private lenders. “No matter what, I’m going to get my investor the money that I promised them—even if the deal goes south and it comes out of my own pocket,” Wendell explains.

He also stresses the value of disciplined underwriting (thanks to his loan officer days). By never stretching the numbers and maintaining a conservative outlook on each deal, he not only protected his investors but built up even more credibility. For him, it’s all about “staying disciplined to the numbers… because numbers don’t lie.”

Shifting from Sales to Service

A key mindset shift for Wendell Butler was letting go of the idea that raising private money is about “selling.” Instead, he reframed it as providing an opportunity—one that could solve a real problem for someone else. This approach—educating, sharing opportunities, and encouraging potential investors to take or leave it—created less pressure and cultivated relationships built on trust, not desperation.

Jay Conner reinforced this, noting that the goal isn’t to chase or persuade but to offer solutions to “ordinary people with lazy money”—meaning funds that aren’t working hard for them. “Private money doesn’t go to the smartest investor; it goes to the most prepared, the most consistent, and the most trustworthy,” he says.

Community and Continuous Learning

Wendell’s entrepreneurial spirit extended to launching The Hive in Charlotte, an entrepreneur meetup designed to foster genuine connections. “When you build true relationships through service, deals and private money wil