A Career Change That Made More Sense Than It First Appeared

Dennis Wells sat down with James Overbo of Macaulay Real Estate in northwest Indiana for a conversation about one of the more unusual paths into real estate the podcast has featured. Seventeen years as a track and field coach at Valparaiso University. An investment property purchased in 2021 to help address affordable housing needs for grad students and university staff. A significant life change last August that closed one chapter and opened this one.

James is nine months into his real estate career and already accumulating more experience than most agents get in several years. The crossovers between coaching and real estate that he did not fully anticipate when he started have turned out to be some of his most valuable professional assets.

Why Coaching Prepared Him for Real Estate in Ways He Did Not Expect

James describes the talent identification work of recruiting as one of the skills that transferred most directly. In recruiting you are learning everything you can about a person to determine fit. You are looking for the right match rather than forcing a placement. In real estate the same logic applies to properties and clients. The homework, the research, the deep dive into pros and cons, the process of helping clients define what they actually want rather than assuming the first thing they say is the final answer.

He also noted that in coaching you have to give someone an accurate read of you in the first three to five minutes and make them comfortable enough to trust what comes next. That skill applies directly to the first conversation with a potential buyer or seller. The knowledge matters but it becomes irrelevant if the person is not comfortable working with you first.

The discipline that athletics builds also shows up in how James approaches his business. He treats it like a nine to five. He is in the office every day. He is visible. That consistency has already produced opportunities from other agents who know he is reliable and available and that the work will get done correctly when they send something his way.

The Investment Property Background That Shaped His Perspective

Before getting his license James purchased an investment property in 2021. The rental market in Valparaiso can be expensive and difficult for the grad students and staff coming into the university and he saw a genuine need he could help address. That experience gave him a working understanding of landlording, tenant selection, and the realities of owning income-producing property before he ever helped a client do the same.

It also gave him a credibility baseline with investor clients that a brand new agent without personal investing experience does not have. He understands the process from the inside rather than from a textbook.

Nine Months In and Getting His Hands Into Everything

The running joke in the Macaulay office is how much experience James has accumulated in nine months. He has worked with first-time buyers who needed their hand held through every step of the process. He has worked with flippers and investors on their hundredth deal who just wanted the paperwork filed and the process cleared quickly. He has had deals close cleanly and deals fall apart before getting off the ground.

The most memorable transaction was his first client. They looked at a lot of houses across northwest Indiana, casting a wide net geographically that eventually led them somewhere that was not even on the original radar. The search took time and required patience from everyone involved. But when the right home appeared the client recognized it immediately and they made it work. That process of staying with a client through the search until the right fit arrives rather than pushing toward an early close on the wrong property is exactly the kind of agent James wants to be known as.

How He Gets Opportunities by Simply Talking to People

One of the most straightforward examples James shared involves his neighbor. Eight years of waving at each other in passing. A yard sale. A casual conversation. His neighbors mentioned they were moving to Florida and James offered his perspective on the house. They were already talking to another agent. The plans they discussed were similar enough in substance that the decision came down to the relationship built in a single afternoon of genuine conversation.

He got the listing.

That is the entire story and that is the point. Not a sophisticated marketing campaign. Not a billboard. A real conversation with real people who needed someone they felt comfortable with. James had been doing that for seventeen years in a different context and it transferred directly.

He is also straightforward about the things he does not know. Rather than pretending certainty he does not have he tells clients he will find the answer and get back to them with the most accurate current information available. That approach builds more trust than a confident guess that turns out to be wrong.

The Buyer Agency Agreement and How He Handles It

One of the most consistent early challenges for James was navigating the newer buyer agency agreement requirement. Buyers who are not familiar with the form can feel an initial layer of distrust and the agreement can feel like a barrier before the relationship even starts.

His approach is transparency and practicality. He explains what the form does, what its scope covers, how commission works, and that the goal is always to structure the deal so the seller covers the commission rather than the buyer. He also shared a recent example where a seller would only cover two percent of the commission he had agreed to seek. He amended the agreement and took the two percent.

The half percent he walked away from is not worth a client's trust or a potential referral. He would rather serve people well, build his name through word of mouth, and let the referrals come from a job done right than fight over fractions at the expense of the relationship.

What the Northwest Indiana Market Looks Like Right Now

James is operating in a market that has shifted from the frantic multiple-offer environment of the spring into something more balanced. He has seen deals where his clients were competing against ten offers. He has also seen the slower rhythm of a market where buyers have more time and more negotiating room.

The experience of navigating both environments in a compressed nine-month window has given him a practical market education that agents who came up in a single-speed market do not have. He knows what it looks like on both sides and can set realistic expectations for clients regardless of which environment they are entering.

Goals for Year Two

James is targeting the top producing rookie designation at Macaulay for his first year. He does not know the exact volume that will take but he has a target in mind and he is building toward it through experience accumulation rather than forcing transactions. Year two is about continued learning, more contacts, and deepening the reputation he is building one transaction at a time.

He specifically wants to be known and trusted not just by clients but by other agents. An agent who is visible, reliable, and known to do good work gets opportunities from colleagues that the invisible agent never receives. He has already seen that dynamic play out and intends to build on it.

James Off the Clock

James works with his hands when he is not working real estate. He recently dropped the gas tank on his Jeep to replace a fuel sending unit himself. He and his daughter have been refinishing furniture together including a desk, a chair, and shelves that she got to sand, paint, and help reupholster. He considers himself lucky that she shares that interest.

When the weekend allows he heads to Lake Michigan and sits at the beach. He also notes that one of the best parts of the career change from college athletics is proximity to his kids. The coaching life meant being away for two days, four days, sometimes a week at a stretch, year round. He has not spent more than a single day away from his kids in a row since making the switch and the difference in the household has been significant and welcome.

How to Reach James Overbo

Call or text James at 219-840-0858 or reach him by email at [email protected].

Dennis Wells works with buyers and investors across northwest Indiana and beyond on financing solutions including DSCR loans and programs for self-employed and non-traditional borrowers. Reach out to Dennis Wells to connect on the mortgage side of any transaction.

Sources

NorthwestIndianaAssociationofRealtors.com
NAR.realtor
MortgageNewsDaily.com
BiggerPockets.com
Investopedia.com