Episode Details
Back to Episodes
Lisa Englehart: Why She'll Never Retire From What She Does in Real Estate Investing
Description
In this episode of Burning the Ships, I sit down with Lisa Englehart, a powerhouse real estate investor, developer, and mentor from Richmond, Virginia whose story is a masterclass in perseverance, grit, and reinvention.
Lisa shares how she went from working in banking to selling REO properties after the 2008 crash, and how one life-changing event with mentor Jim Ingersoll completely transformed her path. Today, she’s known for developing land, building small communities, and helping other investors break through their limiting beliefs.
We dive deep into how Lisa sources off-market deals through “driving for dollars,” funds her developments using private money, and balances business with a purpose – creating neighborhoods where families thrive. She also opens up about what it really takes to succeed in real estate investing: learning from failure, finding the right mentors, and remembering that everything is figureoutable.
If you’ve ever struggled with burnout, self-doubt, or fear of starting over, Lisa’s journey will inspire you to push through, find your purpose, and bet on yourself no matter where you are in your story.
Key Talking Points of the Episode
00:00 Introduction
01:58 JJ’s Joke of the Week
02:46 Lisa’s early years in Richmond and her first steps into real estate
05:02 The first land deal that sparked her passion for development
06:37 Surviving the 2008 crash and pivoting into REO properties
09:28 Meeting mentor Jim Ingersoll and attending her first investor bootcamp
10:37 Walking away from burnout and “burning the ships” to go all-in on investing
12:48 Lisa’s first flip: learning through mistakes and earning through resilience
15:36 Building confidence, using private money, and changing her mindset about borrowing
19:07 How Lisa found off-market deals with zero marketing budget
21:18 The power of handwritten letters and personal connections in seller outreach
24:48 “Find the deal, the money will come”—how this mindset changed everything
25:25 Shifting from flips to land development and small community building
27:12 How Lisa structures her deals with private money and layered financing
33:05 Creating communities, building legacy, and being her buyers’ “neighbor”
36:05 Why she avoids red tape and focuses on shovel-ready land with clean zoning
39:15 “Everything’s Figureoutable”: turning obstacles into opportunities
41:08 The power of mentorship and surrounding yourself with the right people
43:57 Networking, relationships, and how Lisa overcame being an introvert
49:33 Grit, purpose, and why Lisa will never “retire” from doing what she loves
Quotables
“Get a mentor. You’ll get further along if you have somebody to help you—but you have to give back to that person too.”
“Everything is figureoutable. I had to learn that if I wanted to stop sitting on the porch watching everyone else succeed.”
“You have to show up. Go to the events, go to lunch with people, build relationships—that’s where the power is.”
Links
608B Capital