Becker Business Podcast: "Building Success in Southeast Florida Real Estate"

Guest: Jake Geleerd (aka Jamie Gileard), CEO of Tortoise Properties
Host: Scott Becker
Date: November 17, 2025

Episode Overview

This episode features a deep-dive conversation with real estate developer and entrepreneur Jake Geleerd of Tortoise Properties. Host Scott Becker and Jake discuss the evolution and current trends of the Southeast Florida real estate market, lessons from a career marked by resilience and strategic pivots, principles of partnership and team-building, and the personal habits that drive long-term success in the business.

Key Discussion Points & Insights

1. Jake’s Career Journey & Tortoise Properties ([00:40]–[02:36])

• Transition to Real Estate:

  • Started as a golf pro at Club Med before working for Sam Zell at the Equity Group in Chicago.
  • Gained significant experience by taking multiple real estate firms public, working on high-profile deals like SkyDome (now Rogers Stadium), and leading Harapin Properties prior to the financial crisis.

• Resilience and Reinvention:

  • After the 2008 financial crisis, Jake started fresh in Florida, co-founding Tortoise Properties.
  • Led major residential developments in Southeast Florida, especially the recent Tortoise One in downtown West Palm Beach (264 apartments, now 75% leased).

Quote (on past and present):
"I started over, and in 2016, I partnered... and we started a business together in Florida in Palm Beach County ... Tortoise One... 264 apartments in downtown West Palm Beach. We opened up one tower in May last year and the second tower in September, or 75% leased." — Jake [01:44]

2. Trends and Opportunities in Southeast Florida Real Estate ([02:36]–[05:09])

• Impact of Covid & Market Dynamics:

  • Miami’s historic status as an international city; Palm Beach’s reputation for ultra-high-net-worth individuals.
  • Covid dramatically increased migration to Florida—especially from the Northeast and Midwest—creating the “Wall Street South” phenomenon as numerous finance firms relocated.

• Ongoing Growth Drivers:

  • No state income tax, favorable weather, and a collaborative business environment.
  • Emphasis on continued expansion and addressing challenges like affordable housing.

Quote (on Florida’s appeal):
"There's no Republican, Democrat in Florida. In southeast Florida, we all work together for the good of the community. And as long as that continues, you will see companies continue to relocate, continue to expand." — Jake [03:55]

3. Project Evaluation & Decision Framework ([05:09]–[09:03])

• Core Principles:

  • Location is paramount—understand why people would live and work in an area, assess market needs, and competition.
  • Evaluate the local government and business environment—Florida is described as welcoming to business compared to more oppositional city governments elsewhere.

• Financial Discipline:

  • Pro formas are “100% wrong by definition”—anticipate the unexpected (e.g., interest rate changes).
  • Always raise extra capital and have backup plans (Plan B and C) to survive downturns.

Memorable Analogy:
"If you're sitting at the Florida table, they pay a 2 to 1, they pat you on the back, give you a nice dinner and a drink and they ask you to stay. So where do you want to do business?" — Jake [06:55]

4. Building Teams & Partnerships ([09:03]–[10:48])

• Relationship Matters:
  • Invest time in getting to know all key partners—contractors, vendors, leasing and management—before engaging in projects.
  • Enduring partnerships are crucial for successfully navigating inevitable challenges in development.

Quote (on partnership):
"Picking the right people is... in any business, it's a people business." — Jake [10:43]

• Scott’s Perspective:
  • Legal contracts are less important than having the right partners.
  • "You can't do a good contract with a bad partner, but a good partner...you work through those [tough times] and make them work." — Scott [10:50]

5. Habits, Principles, and the "Grit and Grind" ([10:48]–[15:03])

• Daily Focus & Productivity:

  • Inspired by Sam Zell, Jake maximizes productivity, focuses on the present, and is always prepared.
  • Engages fully in every aspect of his work—both in diligence and relationship-building.

• Lifestyle, Not Just Work:

  • Sees real estate as a lifestyle; surrounds himself with people he enjoys working with.
  • "I get the most out of every day... I try to get every minute out of every day as productive and as forward thinking as possible." — Jake [12:54]

• Discipline and Commitment:

  • Learned early (University of Illinois): Always "answer the bell"—no sleeping in or missing a beat, regardless of circumstances.

Quote (on engagement):
"If you're not into what you're doing, get out of it. You've got to be engaged and focused." — Jake [14:06]

Notable Quotes & Moments

• On Resilience:
  "Those are the things you gotta learn over time because you gotta stay in business. Everything is cyclical. Even though Florida's on a nice run, things could change." — Jake [08:44]

• On Learning & Preparation (Sam Zell's lesson):
  "If I didn't know the deal backwards and forwards, I don't get a second chance... So I was always prepared, I always did my diligence." — Jake [13:09]

• On Enjoyment and Purpose:
  "I don't work. It's a lifestyle. But that's by choice, by surrounding myself with people I want to be with, by doing things I like to do." — Jake [13:45]

Timestamps for Key Segments

• [00:40] Jake’s career introduction and evolution
• [03:08] Southeast Florida market dynamics post-Covid
• [05:53] Evaluating new real estate projects and financial discipline
• [09:21] The value of team-building and partnerships
• [12:52] Personal habits, routines, and staying driven

Summary

Jake Geleerd’s journey embodies resilience, strategic acumen, and a people-first philosophy in real estate development. This episode gives listeners not only a masterclass in navigating cyclical markets and building successful projects, but also a look at the personal discipline and relationship-building that sustain a decades-long, dynamic career in Southeast Florida’s booming market. Jake’s story and advice are as relevant to aspiring developers as they are to seasoned business leaders.