The Best Deal I Ever Made Was the One I Walked Away From

Why the most powerful leverage in any negotiation is being willing to walk

What if I told you that walking away from a deal was one of the most profitable decisions I’ve ever made? I didn’t know it at the time. In fact, I was sure I had made a mistake. But not long after, an opportunity came along that would eventually turn a $75,000 investment into more than $7 million in assets.

I would have missed it entirely if I’d gotten what I wanted the first time.

Here’s how it happened. The seller wouldn’t move. I already knew what the property was worth, and I knew what I could pay and still make the numbers work. His number wasn’t it. We went back and forth for weeks. I could see the potential, and part of me wanted to just close the gap myself and call it done.

Instead, I walked.

It stung. I convinced myself I had let an amazing deal slip through my hands. I replayed the numbers, wondered if I should have bent, and told myself I’d been too rigid over what amounted to a few percentage points.

A few months later, a self-storage facility came across my desk. It had gone into foreclosure and was sitting at about 40% occupancy. The numbers only worked at one price, so we made our offer and waited, with no back and forth and no chasing. Eventually, the bank that foreclosed on it called and agreed to our terms. We bought it, rebuilt the systems, rebranded it, and filled it up. Four years later, we sold it for nearly three times what we paid, which was an incredible return on our investment since we had financed it with only 10% down. Through a series of 1031 exchanges, that original $75,000 down payment grew into more than $7 million in assets over the next decade, and it became the engine that funded much of what came after.

(I told the full story of that deal, including how we financed a property no bank would touch, in Your Next Bold Investment Starts Today.)

The property I “lost” would have tied up my capital at exactly the moment the real opportunity showed up. Walking away from the wrong deal is what made room for the right one.

Decide Before You Sit Down

That’s the mindset I’ve carried into every negotiation since: if it doesn’t work out, it wasn’t meant to be. That doesn’t mean I show up passive or careless. It means I do the work before the first conversation ever starts. I decide my walk-away point, the worst outcome I can live with and still call the deal a win. If the terms meet or beat that number, I’m satisfied. If they don’t, I walk, and I don’t look back wondering what if.

Most people do this backward. They walk into a negotiation hoping to figure out their number somewhere in the middle of the conversation, under pressure, with the other side watching their face. By then it’s too late. The number you land on when emotions are running high is rarely the one you’d choose with a clear head. Deciding your line in advance lets you stay calm when the pressure shows up, because the decision’s already made and all you’re doing is checking the terms against it.

I never negotiate from desperation, and that’s not because I don’t want the deal badly. It’s because I’ve seen what happens when a deal I need too much starts dictating my terms instead of the other way around. Desperation always shows, and it always costs you.

Everything Is a Negotiation

This principle doesn’t care what you’re negotiating. Whether you’re buying a house, hiring a key employee, or selling a business, it’s the same discipline every time. But it goes further than business. Most of us negotiate all day long without ever calling it that. We negotiate with our spouse about where the weekend goes, with our boss about a deadline, with ourselves about whether to get up and work out or hit snooze (I hate snooze), and with our kids about bedtime and screens. My kids are expert negotiators, so they keep me on my toes.

Every one of those conversations goes better when you know what matters to you before it starts. What outcome can you live with? What’s the line you won’t cross? When you’ve already answered those questions, you don’t have to win every exchange or get pulled into the emotion of the moment. You can be generous where it doesn’t matter, and firm where it does, and that’s a much better way to live than reacting under pressure all day.

What This Series Was Really About

Over the last month I’ve shared how I built most of my wealth: owning a home, improving it and moving up, making side plays, and now, knowing when to walk away. If there’s one thread that ties it all together, it’s that every one of those decisions was made deliberately, with a clear head and the numbers in hand, and never out of fear or desperation.

That’s how I want to approach money. More than that, it’s how I want to approach life. I’ve used my passion for real estate and what I’ve learned along the way to build financial wealth, and that wealth is a tool. It buys time with my family, the freedom to build what I care about, and the ability to say no to deals, jobs, and commitments that aren’t right. Being able to walk away might be the most underrated kind of wealth.

A Favor
If you enjoy this content, click the 💚 below. It takes two seconds, and it helps more people find these posts. Thank you.

Start Bold

Three moves to bring into your next negotiation:

1. Write down your walk-away point before the conversation starts. Not a range and not a feeling, but a specific number or set of terms you’d be satisfied to accept.

2. Decide it away from the table. Do this with a clear head, days or weeks before, not in the room while the other side is watching.

3. Hold the line without resentment. If you don’t get there, walk away clean, with no bitterness and no second-guessing. Trust that another opportunity is already on its way.

Your Turn

I’ve negotiated with sellers, banks, and buyers, but nobody has tested my walk-away point like my kids. What’s the best deal your kids ever talked you into? Tell me in the comments.

Minor in money. Major in life.

We build financial wealth not for status or scorekeeping, but to fuel the areas of life that matter most: family, health, growth, generosity, and joy.

Don’t drift. Live boldly.

The BOLD Life is for people who want to build wealth without losing themselves in the process - people who want their success to strengthen their health, relationships, purpose, and freedom rather than compete with them. If that’s the life you’re building, you’re in the right place. New here? Start with The Blueprint of a BOLD Life, then read whatever draws your attention. Every post stands on its own.

If you enjoyed this week’s content, please share it with a friend.

P.S. That self-storage deal only worked because I was willing to lose the one before it. Worth remembering the next time walking away feels like losing. When one door closes, another one opens.