Thank you for signing up for my newsletter via the Authentic Mentor website. I’ve decided to brand this newsletter as The Real Estate Venturist to better describe what I plan to write about. I realize “venturist” isn’t a real word, but it’s meant to convey that I’m on a journey with my real estate ventures. My hope is that my experiences, stories, and opinions will help you on your own real estate odyssey.

Every other week, this newsletter will give you a behind-the-scenes look at what it’s like to be a real estate entrepreneur. Here’s what’s in today’s inaugural newsletter:

• Is now the right time to leave your real estate job?

• Leaving a $30 billion private equity firm

• Today’s market opportunity

• Authentic Mentor

To leave, or not to leave, that is the question.

While the real estate market today differs vastly from 2010, when I founded Calvera Partners, the angst within real estate companies feels eerily familiar.

Employees feel beaten up. Honestly, I feel beaten up too, and I’m an owner. The past few years have been brutal.

Acquisitions professionals can’t buy properties. Asset managers are watching rents drop and expenses soar, eroding value. Lenders are tightening up, with bank balance sheets showing strain. Investor relations teams are fielding complaints instead of fundraising calls. Nobody’s doing what they signed up for—unless they’re in private credit.

Stress is sky-high, and the rewards for enduring it are slim, especially when you’re cleaning up someone else’s mess.

Starting a real estate company might make the grind worthwhile, though it brings even more stress and risk.

It paid off for me in 2010. For someone today, maybe not. I prize ownership of my time. It’s empowering to earn based on my ideas, investment theses, and execution.

Would I launch a new real estate firm in today’s climate? It depends. The opportunity isn’t as obvious as it was 15 years ago (though hindsight will likely prove me wrong). Calvera emerged from the Great Financial Crisis—a stressful time that became my personal catalyst. Perhaps today’s challenges will spawn a new wave of real estate entrepreneurs.

Calvera Partners rose from the GFC 

In 2010, I left a $30 billion private equity firm—where I’d just been promoted—to start Calvera Partners with two business school classmates and former colleagues. Real estate, like tech, is an industry where many think, “I can do that.” Plenty can, and even more try.

I’d dreamed of being an entrepreneur since selling homemade wrapping paper as a kid. As an adult, though, I took the safe route: undergrad business major, four years at a big bank, a top-10 MBA, then private equity. Not exactly the scrappy entrepreneur’s path—but it works in real estate.

Real estate entrepreneurs need either money or a deal. Having both is golden; having neither makes life tough.

I spotted opportunity in my backyard. In San Francisco, a major landlord was reeling from over-leveraging thousands of apartment units. Rents had tanked in the Bay Area due to the GFC, and I knew distressed portfolios would hit the market. Calvera aimed to chase those, but our first year fell flat.

So we pivoted, staying local. Rents were surging in Silicon Valley. Cap rates stayed low, but growth was undeniable. Tech was fueling a post-GFC rebound, and we began buying small apartment properties (7–50 units). Those deals were some of our best and helped us build our investor base. Today, we’re acquiring 150-, 200-, and 300-unit properties nationwide.

Today’s market opportunity

Today’s opportunities feel murky—not because they don’t exist, but because they demand more faith than facts.

I’m convinced office investments will yield huge returns for those with the stomach and the cash. But timing’s a gamble: you might land a tenant next week or wait three years to fill your space.

I also believe apartments will rebound once the current supply glut fades. Unlike office, where gateway markets are key, apartments will see patchy improvement nationwide. We’re already seeing it in the Midwest, with strong leasing velocity and rising rents.

The beauty of real estate entrepreneurship is the diversity of markets and property types. You can master a niche—maybe one I’d never touch. Those untapped corners are often the best places to shine. The struggles, challenges, and triumphs are universal, no matter your strategy.