The Million Dollar Reality Check: Why Most Business Owners Fail to Sell Their Companies

Ever wonder why some business owners walk away with millions while others can’t even get a buyer to look at their company? I recently sat down with Jacob Koenig from Woodbridge Group, and what he revealed about selling businesses shocked me. Here’s the brutal truth about what’s really happening behind closed doors in M&A deals.

The Ego Trap That’s Killing Your Business Value

Let’s cut straight to the chase. The biggest mistake business owners make? Thinking they’re irreplaceable.

As Jacob put it: “A lot of people who have their ego tied up in a company will come out and say, ‘Look, this is how important I am, this is what all the things that I’m doing, this is how great I am.’ And not enough focus on the company and how it can run without you.”

Here’s the hard truth: If your business can’t run without you, it’s worth far less than you think. Buyers don’t want to purchase a job – they want a business that will thrive after you’re gone.

The Numbers Don’t Lie: Why Going Solo Could Cost You Millions

Think you’ll save money by selling your business yourself? Think again. According to Jacob, “95 percent of the deals that we do end up with buyers who are our client has never heard of before.”

Let that sink in. You’re probably missing out on 95% of potential buyers by trying to go it alone.

The Perfect Timing Myth

One of the biggest myths in selling your business is waiting for the “perfect time.” Here’s what Jacob had to say about timing:

“If you try to time it where you’re top ticking the market or top ticking your business, it’s almost always going to result in heartbreak. The fact is people, buyers can smell that.”

When Should You Actually Start Looking to Sell?

The best time to sell isn’t when you’re at your peak – it’s when you still have growth potential but need help getting to the next level. As Jacob explains:

“A lot of the sellers that we speak to, people who have been running their business for many years, decades sometimes, and they’ve gotten to a point where ‘I’ve grown this thing as much as I can, and I need some help, I need some fresh view to really get to that next level.'”

Inside the M&A Process: What Actually Happens

Here’s what most people don’t tell you about selling your business:

1. Initial Preparation
   • Creating detailed company information
   • Producing promotional videos
   • Getting financials in order
2. The Auction Process
   • Sending out teasers to hundreds of potential buyers
   • Getting non-disclosure agreements signed
   • Reviewing initial bids
3. Deal Structure
   • Cash upfront isn’t always the whole story
   • Equity roles (10-40% ownership retention)
   • Earnouts based on future performance
   • Seller financing options

Time Kills Deals: The Silent Deal Killer

Want to know the number one reason deals fall apart? Time. “The industry average is somewhere between five and 10 months. We always try to do it in two. 60 days is really the goal,” Jacob shares.

Why? Because the longer a deal takes:

• More things can go wrong
• Buyers can get cold feet
• Business performance might slip
• Legal fees keep mounting

Hot Industries and Market Trends

Right now, certain industries are seeing massive buyer interest:

• Pet care services
• Recession-resistant businesses
• Healthcare-related companies
• Companies with predictable revenue streams

The Million Dollar Question: Is Your Business Actually Sellable?

The good news? According to Jacob, most legitimate businesses can find a buyer: “Any company that’s not doing anything fraudulent or otherwise, as long as you’re upstanding and you’re honest, transparent, and you’re running a business that’s making money, we’ll find you a match.”

Taking Action: Next Steps

Ready to explore selling your business? Here are your next steps:

1. Start documenting systems and processes
2. Build a management team that can run without you
3. Get your financials in perfect order
4. Consider professional M&A guidance

Want to learn more? Connect with Jacob Koenig on LinkedIn or visit Woodbridge Group for more information. You can also check out their amazing case studies on their YouTube channel.

For the full conversation, listen to the complete episode on Spotify or Apple Podcasts.

Remember Jacob’s golden rule: “Time kills deals.” Don’t wait until it’s too late to start planning your exit strategy.

Want to continue the conversation or get more specific advice for your situation? Drop a comment below or reach out directly. Like always, I’m here to help you take that next step in your journey, wherever you are.