From a $12M-GCI Hobby to a Real Business with Jonathan Spears

What hit me upside the head is when I sold $450 million, and I could not tell you where that $12 or $13 million in GCI went. I feel like I know and I'm a very good steward of finances. I've never struggled in that department, but I was never looking too close.

My guest today got his real estate license on his 18th birthday. That was 2010 in the Florida Panhandle right after the crash and right after the BP oil spill fouled the exact beaches he was about to sell homes on. Most people would call that spectacularly bad timing. Jonathan Spears called it an opening.

He started in foreclosures at a small shop in Destin — high volume, ugly deals, the kind of work that teaches you the mechanics of a transaction whether you want to learn them or not. He was also finishing a business and finance degree at Florida State, which he graduated at 19. In 2015 he pivoted to luxury. Two years later he had a team. Today Spears Group is the number-one team in Northwest Florida with over $2.5 billion closed, and Jonathan crossed $1 billion in career volume before he turned 30.

But here's the part I actually want to get into. He'll tell you that for years he wasn't running a business. He was running what he calls a high-paid hobby. The production numbers looked great, the brand looked great, and underneath the water he was paddling like a maniac just to keep the surface smooth. What changed wasn't more hustle — it was operations.

>> Jonathan, welcome. >> Let's go, Ross. Glad to be here. >> Start way back — 2010, Florida Panhandle. The market is on fire in a bad way, the oil spill has just hit the beaches, and you got licensed anyway. What did an 18-year-old see that older people were missing? >> That time was chaos. The old adage that stuck with me is hard times produce great entrepreneurs and great times produce really soft entrepreneurs. Those hard times are what my foundation was built on.

I watched my parents nearly go into bankruptcy. I watched my gym partner — a stock trader — lose his whole business. But I was not your ordinary 18-year-old. I'd started college at 14, had my first degree at 16, bachelor's at 19. I was working in real estate my last year of college. I had no financial exposure personally to what was happening. I remember sitting in economics class when Lehman Brothers collapsed. None of that discouraged me — if anything it put a chip on my shoulder: that's never going to be me. I'm going to build.

>> What did the foreclosure work teach you that agents in a normal market wouldn't learn? >> There's a gap today between agents who think Million Dollar Listing and Selling Sunset is what the business looks like and the reality. I spent five years — all of my high school and early college — grinding. Never went to prom. Mom dropped me off at school every day. No partying. I gave up a piece of my life to build what I have today.

I had FOMO at 18 of 35-year-old Jonathan. Now I have FOMO of 50-year-old Jonathan. My motivation comes from looking out and going, if I don't plant these seeds today, I don't live that future. That's what 18-year-old Jonathan was thinking, and that's the competitive advantage I had.

>> Take me to that first luxury listing. You had no track record at that price point. >> In Florida, most top agents at that time, I would've been their grandkids' age. I was out of my league pitching that first appointment. Here's how I got it: foreclosures are a reactive business. Back then we were submitting broker price opinions to asset managers. I was doing 10 a day, six days a week — mold, fleas, dilapidated properties. Not sexy. But I learned a reactive path.

I had to figure out: how do I pivot from reactive to proactive? I'd pull the hot sheet 12 times a day. See who put something pending in the luxury segment, snoop the tax records, understand who was transacting and why. I'd farm neighborhoods with handwritten letters. My first luxury listing came because I sold a foreclosure in a neighborhood, met one of the neighbors on site, and started a conversation that was genuinely about relationship — not about selling him something. Cold to warm. That was the spark.

>> Does that still apply at your current scale? >> If you stop prospecting your business dies. Real estate is the closest comparison to professional athletics — when a professional athlete quits training, their body atrophies and they have nothing to offer. When salespeople quit sharpening their skills in the market, when they quit cold-calling, the business goes with them. Most salespeople live in a high-low trajectory because on the ascent they stop doing the thing that got them there. I've been intentional for 17 years about staying on an ascent.

Yesterday I told my executive assistant: there are only three motions you're allowed to do from now on. Prospect, show up, follow up. We cut the bottom seven items off her to-do list. We actually hired her an assistant so she could stay focused on those three because they are the most dollar-productive things in our business. If I have her doing it, me doing it, and a whole team doing just those three things, we can crank.

>> Let's get into the hobbyist-to-professional idea. You've written that for years you thought you were running a business but you weren't. >> Most hobbyists would not admit they're professionally in a hobby. That would have been me circa 2021. The symptom of a hobbyist, the most typical one, is somebody who doesn't understand their finances. Top agents doing $400-500M+ a year — I talk to so many of them who don't run P&Ls, don't watch expenses, don't track month over month. They cannot hop on an earnings call about their own business.

>> This hits home. I've been doing this 20 years and only in the past four years did I start running P&Ls. I cut my expenses to a third of what they were. The stress level dropped. >> What does that do? It removes the anxiety. Are we our best selves when we're anxious? Absolutely not. I'm the worst parent, worst friend, worst leader when I have anxiety. When I have clarity I'm the best at all of them. Clarity is king. That's why we built MyOps.

The patterns of a hobbyist: no system, no process, reactive to the external world every day. Then there's high-performing hobbyism — the person who looks in the mirror and says I have it all together. That was me. Sold $450M, had it figured out. As soon as somebody asked: how much did you make, how much did you spend, what's your marketing spend, average commission rate, what's your team business worth separate from your personal production — I had no answer.

The best juxtaposition for real estate is the hobbyist golfer versus the professional. Hobbyist: woke up today, weather is good, I'll go play the back nine. Tomorrow it rains, scroll social instead. No routine. Pro: in the gym before the field, dietician has already picked the day's meals, mind right before physicality. The pro real estate agent runs a business they could step out of that other people could step into. Hobbyist runs a job that collapses when they leave.

At $450M I was a self-professed CEO with no understanding of our finances. I couldn't tell you how much my assistant made. If someone complained, I'd just pay them more because I was so busy. Busyness is not productivity. Leaning into how I'm actually productive — if I have eight hours in the day, how do I do more than any other human on the planet? Cut that in half — if I have four really good hours, how do I maximize those?

>> This sounds like the operational breaking point. >> One thousand percent. MyOps is an AI-native platform I built with my operators. A lot of top agents have great systems — they live in Google Drive, shared notes, text messages. If you're still running your team in text messages, that's one of your greatest organizational threats. When somebody leaves, they have all the receipts and the casual tone you were probably more casual with than you should have been.

I needed somebody from the outside to help me get organized. That was Maria Koukoulis. She was originally my publicist — she branded 30A as the Hamptons of the South and got us in the Wall Street Journal. I spotted a broader operator skill set and invited her into a different position. She said yes. That's how I got my COO.

>> What does MyOps do? >> MyOps was two years of custom work. All the operational issues I mentioned — I needed an aspirin and all I saw on the shelf was vitamins. Maria and I engaged an architect to design software that could actually solve the problems. P&Ls are usually static. MyOps takes my P&L and rectifies it against active and pending deal flow in real time. I can see projected net income, not just gross, and make real decisions off it.

AI's best capability is querying data at a high rate and saving us a ton of time on operational inefficiency. The biggest inefficiency agents have is getting asked the same questions over and over by different clients, by their own agents, by their operator. Same data regurgitated endlessly. Putting it in one spot and letting an AI (we named it Maria) regurgitate it from a single source of truth is a huge unlock.

>> What proved it was working? >> I spent 37 days in Colorado with my family this summer. Before MyOps, if you'd asked me circa 2021 whether I could go to Colorado for 30 days I would've choked. In those 37 days my team's volume went from $240 million to $340 million. At a glance I could see the entire operation — what Max was producing, what Mark was doing, how many open houses we were holding. My anxiety went down because the data was there.

In six months we've onboarded about 300 agents who average $117M in production. These are people already crushing it who know they need something more. I wasn't too proud at $450M to admit I didn't have it figured out. I had to uproot a 12-year-old tree and replant it. That meant pruning and change, but the question was: how do I get this to grow in a way where if I step away, it keeps growing?

>> What are you building toward now? >> The thing I'm most excited about is impacting the industry as a whole, not just a geography. Being 34 and looking at where our industry is headed, MyOps is my greatest purpose right now. I see it becoming the operational platform for real estate. As technology thrives and conglomerization keeps happening, people are going to want their time back and want to eliminate the anxiety. That's what we're building.