Know Your Broker: Tom Bailey

Tom Bailey, like several other brokers on our team, grew up on a farm and hence developed a great love for the outdoors. One particular aspect of the outdoors that Tom was drawn to were the waterways of America. He’s kayaked the whole Missouri River and has also kayaked all the way down to the Gulf of Mexico.

With that level of commitment, it’s not that surprising that he started working for the owner of the kayak rental company he worked at in between these big trips. Some time later the opportunity to buy the business came along and Tom went for it. He still operates KC Kayak LLC on the weekends. You can get a perspective on kayaking near Downtown KC here.

Tom’s undergraduate degree is in metallurgical engineering, from the University of Missouri at Rolla (Now Missouri University of Science and Technology), where he learned to be process-focused, asking questions along the way. He also picked up an Executive MBA from Washington University in St. Louis. That business background and process mindset has served him well in business brokering. “I really enjoy peering into different businesses and learning all about this new world and the complexities I could have never guessed.”

The human side of business brokering can have its humor. Tom shared that recently he was given an unintelligible checkbook register when he asked for financials. When he asked for more details, he got a handwritten P&L.

Then there’s the seller who was convinced his business was worth a 10x multiple. “I asked him to put himself in the buyer’s shoes and reframed it: ‘Would you pay 10X for a competitor?’ When he answered no, that made it easy for me to say, ‘Then don’t expect anyone to pay you that, either.’”

But Tom understands where that “10X” valuation is coming from, as well. “These people have been building these businesses for many years so sometimes all that blood and sweat and tears inflates into a large number.” Tom sees it as his job to make sure his clients understand the realities of the market and what a business can realistically fetch.

When he’s not with his clients, Tom keeps busy with a young daughter and when he can, he gets away camping on the Missouri River.