The Trap of the “Successful” Wholesaling Business (And the Mistake That Almost Killed Mine)
On social media there are a lot of people talking about how they are absolutely “killing it” with wholesaling.
I’ll tell you a different story. About a year ago, I realized my business was killing me.
I was walking my dog along the river early one morning, just after sunrise, when a heavy thought poked me: If this business stopped today or tomorrow, I’d be scrambling to make ends meet. That’s no better of a situation than before I started the company. Back then, I was selling art at live shows and online, making new stuff every week just to keep up and pay the bills. Now, I owned a real estate wholesaling business. But at the end of the day, it was still just a job.
It was a high-paying job, and I was grateful to be my own boss, but until you are banking heavy cash reserves and creating vehicles that pay you while you sleep, it’s a job.
Hitting the Wall
Five years in, I had hit a wall.
On paper, we looked successful. I had built a business with seven team members, and we were closing an average of four deals per month. We had grown every single year. Everyone was getting paid salary plus bonuses, including me. We had made a small profit over the last two years, which barely offset what I put in to bootstrap the business at the start.
But behind the scenes, my tank was empty. I had put so much of myself into the daily grind that the stress was dictating my quality of life. I was having frequent panic attacks. I actually had to scale back my involvement in my own company just to protect my health.
I started fantasizing about selling it. But what would I get for a business that relied entirely on my daily stress to function? Enough to buy a basic, turn-key laundromat or a car wash? I didn’t want to quit—we were close to really making good profit—but I genuinely didn’t feel like I had much left to give.
The “Drain vs. Energize” Audit (And the False Fix)
I knew the theoretical answer. I had consumed Dan Sullivan’s material and participated in Strategic Coach. I knew the concept of Who Not How. I knew I needed to delegate the things that drained me and operate primarily in my zone of genius.
But I subconsciously believed that success required pain and grinding. I didn’t trust that working only in areas that brought me joy would actually be productive. Still, my body gave me no choice. I couldn’t keep going the way I had been.
I did a ruthless audit of my daily tasks, creating two categories: “Drains Me” and “Energizes Me.” I decided to farm out the drain tasks and hire an operations manager to bridge the gap between me and the daily grind.
I thought I had solved the puzzle. I was wrong.
The Difference Between Delegation and Abdication
I made a near-fatal leadership mistake: I stepped away too soon.
I handed the reins over to the new operations manager without verifying that he could actually deliver. I confused delegating with abdicating. I completely took my hands off the wheel without confirming that autopilot was working.
Within a year, the business tanked. The operations manager had a hand in the decline, but ultimately, the fault was mine. I had to step back in, fire him, and let three other people go just to right the ship.
One Year Later: Becoming a Real CEO
I wrote the original draft of this post about my panic attacks over a year ago. Today, the landscape looks completely different.
I survived the crash, but the rules of the game had to change. Today, I am the CEO of a lean, highly capable team of five. I operate almost entirely in my zone of genius, far away from the high-friction day-to-day operations, but with one massive difference: I keep my finger firmly on the pulse.
Here is what actual leadership looks like for me now:
- KPIs over Blind Trust: I empower my team, but I set crystal clear expectations for KPIs and verify the data.
- Coaching as a Superpower: I regularly check in with everyone. One of my true strengths is coaching and inspiring people, so that is one place I focus my energy.
- Visionary Focus: I do the behind-the-scenes visionary work the business actually needs to grow and stay on track.
If you are a few years into building your business and you feel like you are drowning, hear this: You do not have to suffer to succeed. Audit your energy, hand off the heavy lifting, and build the job you actually want to show up for. You will be happier, so will your team, and your business will do better.
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