From Solo To Squad: The First Three Hires Every Land Investor Needs

Whether you are a solo investor drowning in data or a growing firm ready to build an empire, transitioning from a one-person show to a high-performing squad is the most critical leap you’ll ever make. In this episode of the Land Academy Show, Steven Jack Butala and Jill DeWit pull back the curtain on a decade of hiring wins, losses, and “what was I thinking?” moments. They break down the “Solo to Squad” framework: the first three essential hires that move you from being “a guy with a hobby” to a true business owner. From seasoning your first “CEO-potential” administrator to finding the technical whiz who handles the data you hate, they share the exact strategy we use to buy back our time and scale our deal flow. In This Episode, You’ll Discover: The “Seasoning” Strategy: Why your first hire should be someone you can groom to eventually handle the big decisions. Hiring for Weakness: How to identify the tasks that are currently “costing you money” because you’re too slow or too bored to do them right. The Entrepreneur’s Trap: Why trying to “save” a friend or hire a “startup” personality can backfire during the operational phase. Meeting Your Team Where They Are: My unconventional (and perhaps controversial) advice on motivation, turnover, and finding the “soul” of your company. The Power of the Squad: How a dedicated team allowed us to move from struggling in 2009 to building multiple revenue streams and a legacy in land. Stop doing the busy work that keeps you from the deals you should be making. It’s time to stop overanalyzing and start building your squad.

You can listen to From Solo To Squad: The First Three Hires Every Land Investor Needs online on Radio and Podcast. Open the player on this page to stream the available audio.

From Solo To Squad: The First Three Hires Every Land Investor Needs is an episode from Land Academy Show by Steven Butala & Jill DeWit.

This episode is 30:00 long.

This episode was published on Apr 1, 2026.

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