How I paid off $2m of debt through selling my business

Hey ,

By the time I was 21, I was millions of dollars in personally guaranteed debt. I ended up paying it off through building equity not cash flow.

My last business - real estate management and development that I grew through acquisition - was heavily asset based, which naturally demands a lot of capital. If you don’t have the capital, you need debt. I had a grand strategy for the company, I predicted an era of inflation where currencies would steadily lose value. In that context, debt gets cheaper over time. I leaned into that logic, hard. I loaded up on loans, confident it was a smart strategic move.

At its peak, my debt totaled just over £2m or $2.6 million. That included about $1 million in mortgages, $1.4 million in investment liabilities, and $250,000 in bridging finance. It was a mix of long-term commitments and short-term pressure, all tied to an asset-heavy business model.

But what started as a calculated play quickly became a major source of stress in my life.

My first takeover was successful and we booked a half million dollar gross profit in the first year running the newly acquired business. I did everything you’re ‘supposed to do’ in business. I slowly paid the loans down in installments and sold a property for £300,000. But five years later, I was still stuck with over a million of the debt. The asset finance just wouldn’t budge. Despite enjoying the profits along the way, I felt trapped. I wanted to wipe the slate clean. That’s when I made the decision to find a buyer and exit.

I was averaging just about six figures in debt payments every year. I did everything you’re supposed to do as a business owner. But I felt burdened. Every month, I was earning just to pay banks and investors. The weight of that obligation never left. I started to wonder—what would life be like if I had no debt? If all that income actually went to me?

So I set a clear mission: to find an all-in-one deal—no payment plans, no trailing liabilities—that would wipe out every ounce of financial dead weight. After 18 months of searching, a few false starts, and some tense last-minute negotiation maneuvers, I finally landed it. A buyer acquired the business, clearing off all asset financing and buying for £1.2 million ($1.5 million). The moment the deal closed, I cleared every remaining loan. Just like that, the debt was gone.

What I Learned About Selling a Business Under Debt

1. Buyers care more about cashflow than your debt
   Debt is your problem, not theirs. If the business performs well, there is a buyer, even if you're buried in liabilities.

2. Clean exits are rare but powerful
   Many deals involve earnouts or claw backs. If you want a clean break, you have to be upfront and disciplined during negotiation and push for a complete buyout.

3. Don’t wait until you’re desperate
   I didn’t sell because I had to, I sold because I wanted to. That gave me leverage. Desperation usually means the buyer has all the cards.

4. Debt can make you blind to your freedom
   I thought I was being strategic with debt. And maybe I was - it did do what I expected it to do. But doing the math doesn’t include the mental strain and pressure of being under debt.

On the next issue, we’ll be doing a great case study on a $4.75M family business.

Until next time,

Unlocking Wealth Weekly