I Reviewed 100 Businesses. Only One Was Worth an Offer.

I reviewed nearly 100 businesses looking for my next acquisition. I submitted ONE letter of intent.

Over my career, I’ve had the opportunity to start, grow, buy, and sell multiple businesses. Like most entrepreneurs, I’ve experienced the highs that make it all worthwhile and the lows that make you question nearly every decision that led you there.

After selling one of my businesses, I began looking for the next opportunity. I reviewed close to 100 companies, searching for a business I could acquire, grow, and help take into its next chapter. There were a lot of good businesses in that group. Many were profitable, well-established companies built by incredibly hardworking owners. But as I dug deeper, I kept finding risks that were difficult to overlook.

In most of the business, the owner was responsible for nearly all of the sales. In others, the supplier relationships depended entirely on the owner’s personal connections. One company had a single customer responsible for 35% of its revenue, and that customer happened to be the owner’s brother-in-law.

The financial statements often looked strong, but when you pulled back the layers, the businesses were far more fragile than they first appeared. Their success depended too heavily on one customer, one relationship, one employee, or, most often, the owner. Of the roughly 100 businesses I explored, I submitted one LOI (letter of intent).

That experience stayed with me. I have an enormous amount of respect for entrepreneurs and what it takes to build a business. I’ve been in your shoes, and still am. I understand mortgaging the house to make payroll. I understand the late nights, early mornings, missed family events, strained friendships, and the weight of knowing that employees, customers, suppliers, and their families are counting on you. Business ownership can be incredibly rewarding, but there is a cost that rarely appears on a financial statement. Owners invest years of their lives, take risks most people never see, and carry responsibilities that can be difficult to explain to anyone who hasn’t lived it.

That is why I couldn’t get past the brutal reality that many businesses are not being built to eventually transfer, transact, or operate successfully without their owner. An owner may spend 20 or 30 years building a profitable company, only to discover that much of its value depends on them continuing to be there. When they are finally ready to step away, often the business is difficult to sell, worth less than expected, or unable to continue without them.

A massive percentage of owners could see their life’s work go largely unrewarded. Not because they failed to build a good business, but because no one helped them build a business that could confidently continue under someone else’s ownership.

That is why I started VentureOut.

Our goal is to help entrepreneurs understand what they’ve built, identify the risks hiding beneath the surface, and intentionally create a stronger, more valuable, and more transferable business. We want owners to have more choices, whether they plan to sell, transition the company to family, bring in a partner, step away from daily operations, or simply build a better business today.

I’m not standing on the sidelines offering theories. I’m still building companies, taking risks, solving problems, and navigating the same uncertainty as the entrepreneurs we support. I’ve been in the trenches, and in many ways, I’m still there. My hope is that VentureOut can help more entrepreneurs thrive, maximize the value of everything they have built, and ultimately receive more of the reward their effort, risk, and sacrifice deserve.