177| From Raw Dirt to Real Deals: How to Develop Your Land (the Right Way) with Eugene Gershman

📝 Episode Summary

In this episode of Million Dollar Flip Flops, Rodric sits down with Eugene Gershman, CEO of GIS Companies, to demystify real estate development for landowners, builders, and investors who know they’re sitting on potential—but don’t know what to do next.

Eugene started in the family construction business over 20 years ago, transitioned into full-time development, and now runs a development services company that partners with landowners across the country. His team handles everything from feasibility and entitlement to design, permitting, capital stack, and GC selection—and instead of billing by the hour, they take JV equity and get paid when the project succeeds.

He breaks down:

•. What to look at first if you have a piece of land and a dream

•. Why feasibility is non-negotiable

•. How “money follows good deals” (and how to structure those deals)

•. The reality of permitting timelines, IRR vs equity multiple, and why he targets 2x+ equity rather than obsessing over IRR

•. How early-stage capital actually works (GP funds, bridge loans, angel investors)

If you’ve ever thought “I’d love to build something on this land, but I have no idea where to start,” this episode is your crash course.

🔑 In This Episode, You’ll Learn

•. What GIS Companies actually does

How Eugene’s team acts as a development partner, not just a consultant—bringing in the team, structuring the deal, and taking JV equity instead of hourly fees.

•. Who can work with them (hint: you don’t need experience)

Why you don’t need to be a developer to develop: from families with legacy land to builders stepping up in scale, Eugene loves helping people go from “I own dirt” to “I own a project.”

•. Why feasibility is the first non-negotiable step

Zoning, entitlements, municipality history, neighborhood opposition, site layout, market data, costs—they walk through all of it before anyone talks about pouring concrete.

•. How to think about “hard” municipalities

Why Eugene doesn’t care if a place is “hard”—he cares if it’s possible or impossible. If it’s not impossible, there’s a path.

•. The truth about finding money for your project

Why money follows good deals and why you can’t raise capital credibly until you know:

•. What can be built

•. What it costs

•. What the investor gets

•. Early-stage vs late-stage capital

•. Late-stage investors love coming in when permits are issued & debt is locked.

•. Early-stage money is harder and often comes from GP funds, bridge loans, and angel investors willing to accept higher risk.

•. How landowners can tap into their land value without selling outright

Using bridge loans (50–60% of land value), pairing that with feasibility, and understanding how bringing in partners dilutes you—and why that’s not always bad if structured right.

•. Returns: IRR vs Equity Multiple

Eugene explains why IRR is fragile (because permitting timelines blow it up), and why he prefers tracking equity multiple—aiming to double investor money (2x) or more over the life of the project.

•. Why right now might be a great time to start a project

Eugene shares his view that the next ~5 years could be a strong cycle for development—and why people sitting on land should seriously consider building instead of waiting.

•. How he thinks about sustaining goals

In response to a listener-style question, Eugene explains why habits and routines, not motivation, are what keep you from “losing 10 lbs and then going back to cake.”

⏱️ Suggested Timestamps

[00:00] “Money follows good deals.”

Why investors won’t show up until you can...