Episode 176: Dr. Jennifer on Real Estate Development Land to Legacy, Surviving Your First Development
Summary
I recently had a great guest on my show on Episode 158, Eugene Gershman, who talked about how he co-develops with landowners and creates a great product for communities around the US. He learned of our Maui development that was 28 years in the making, and asked me to join him on his show, to talk about “How to Survive Your First Development”.
Join me today, talking with Eugene about surviving development. If you want some basic advice on real estate improvements, today’s episode is it!
Listen to the full episode :
This Week’s Blog Post:
How It All Started
Hi friends! I’m Dr. Jen, and in this episode of My Life as a Landlord, I joined Eugene Gershman on his Land to Legacy podcast to talk about what I’ve learned from real estate development—especially when you’re managing your first big project. We covered everything from assumptions to financing, building a team, and keeping your sanity during construction. I shared how my husband Michael and I built eight fourplexes in South Maui, how we handled setbacks, and what I wish I’d known before we started.
Checking Your Assumptions
The first thing I tell anyone getting into development is this: check your assumptions. Everyone does it—you plan with optimism, assuming construction costs will stay steady, the market will hold, and financing will come easily. But as I shared with Eugene, every assumption needs a reality check. Development always costs more and takes longer than you think. You’ll pay in time, money, sleep, or stress, so you might as well hire people who have done it before. Mentors can save you from expensive mistakes because what’s new and scary to you is just another Tuesday to them.
Managing Mistakes and Staying Calm
One of the hardest parts of any project is dealing with mistakes. Things go wrong—materials are misplaced, tanks are set in the wrong spot, or code requirements change. I use what I call the 90-second rule: let yourself get mad for 90 seconds, then focus on the fix. Losing your temper doesn’t help. Have a calm conversation with the person involved, ask for their proposed solution, and move on. When everyone knows that fixing the problem matters more than placing blame, you save time and keep your team motivated.
Choosing Focus and Building the Right Team
I also talked about how tempting it can be to try doing everything yourself—acting as your own general contractor, managing permits, or handling every trade. But the truth is, you can’t master it all. Pick one or two things to focus on and hire experts for the rest. A good general contractor brings more than skill—they bring speed, experience, and a network of people who can solve problems fast. Development is hard enough without trying to be a master of all trades.
Final Lessons and Defining Success
For me, success isn’t about money—it’s about time, health, and freedom. I designed my life so I can work from my boat in Desolation Sound, meet with my team online, and still have time to play in the afternoon. That’s what all the hard work was for. If you’re just getting started, educate yourself every day. Listen to podcasts, read, and stay curious. Development and real estate are full of awkward conversations and learning moments, but the more you expose yourself to them, the more confident you’ll become.
This episode was recorded while anchored in Desolation Sound, British Columbia. Why? Because real estate takes you places. Where do you want real estate to take you? Join me next week for Episode 177, where we’ll explore new insights from landlords across North America. I’ll see you there!