Will You Regret Selling Your Business?

You’ve heard about buyer’s remorse — when you buy something you’ve always wanted, only to second-guess the move when you discover the purchase didn’t make you happy. But what about seller’s remorse — when you ultimately regret the sale of something you seemingly ‘love.’ Like a house… or a business.

When you sell your company to a new owner, four items can trigger seller’s remorse, according to Lyons Solutions LLC, an M&A advisor:

  1. Still having passion for the business.
  2. Perceived loss of identity and self-worth.
  3. Concern about leaving money on the table.
  4. Worrying about what to do with your life after selling.

So how do you prevent seller’s remorse? Viking, another M&A advisor, recommends focusing on six action items:

  1. Have a good reason to sell.
  2. Explore options and learn.
  3. Gain financial security.
  4. Be sure about your plan.
  5. Find an agent
  6. Stay confident.

Focus On the Journey (Not the Event)

Now, my two cents. When my business partner (Amy Katz) and I sold an IT media mall business in 2011, we had an overall positive experience. But the “event” — the actual company sale — triggered mixed emotions.

  • On the one hand, much of our net worth had been locked up in the business. Selling was a way to unlock some of those funds and put aside some money for our respective family needs (most notably: college savings). Selling also meant we were could plug into a larger network of talent; the business’s new parent had market and platform skills that we simply couldn’t hire or fund on our own.
  • On the other hand, selling meant losing control of a business and associated content platforms that we loved. So, there were some highs and lows associated with the sale “event.”

Still, we ultimately focused on the journey. That meant integrating the business we built into a larger company; exceeding the financial and business targets tied to the deal; and ultimately writing succession plans to ensure the business continued to perform once we left.

The succession planning (including turnover reports) was particularly important to us. When we resigned in early 2014, we left clear instructions for how we’d focus the business going forward. Whether the new owner followed or abandoned those plans was beyond our control.

The Journey Continues

Plenty of folks ask me if I “look back” on the business we sold. The simple answer is “no.” When I resigned, I told people I needed some silence to hear again. Frankly, IT industry noise had overwhelmed my thinking at the time. Stepping away in early 2014 gave me some time to think about what I’d like to do next with my life.

I think the same can be said for Amy Katz. Unlike many business partners, she and I remained united during every step of the journey. From startup, to company sale, and even post-sale. And perhaps that’s why I never really suffered “seller’s remorse.” In the back of my mind, I always suspected that Amy and I would hatch another business together. And by 2015… we did.

Getting the Band Back Together?

Our story isn’t unique. Over and over again in the IT services industry, we all hear about entrepreneurs who “get the band back together.” In a typical scenario, the entrepreneurs work with a group of crazy talented employees. They build a business. They sell it. They eventually disappear. And then they eventually surface again, with another startup.

But back to the headline of this article. Will you regret selling your business? In my case, the answer was “no” because of two reasons:

  • Amy and I focused on the overall journey, rather than the sale event.
  • I always looked ahead and thought about tomorrow’s possibilities — rather than looking back to re-evaluate decisions that were already made.

Onward. Upward. If you’re formulating an exit strategy, make sure you’re able to sign on the dotted line with zero regrets.


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    Jeff Weinman:

    Tomorrow’s possibilities…and an optimistic outlook are powerful views/traits! From an entrepreneur’s perspective, I think these top the list. And as you point out, they help beyond “the business” and with life in general.

    Great post Joe.

      Joe Panettieri:

      Hey Jeff: Thanks for your readership. For the vast majority of entrepreneurs, I suspect all of the buy/sell answers are right in their hearts. If it feels right, then it’s the right deal at the right time. Please keep us posted on your own business journey.

    Mike Benkovich:

    Hi Joe – thanks for the insight.

    I’m struggling through this thought process right now. After 10 years I sold my business and have achieved some financial independence. Alas, 6 months down the track I’m feeling fairly disillusioned and directionless. Time off sounds great but for those of us driven enough to get there it’s a double edged sword. Time to think isn’t always a good thing.

    I think you’re right. I need to focus more on the possibilities ahead of he than what I’ve left behind.

      Joe Panettieri:

      Hey Mike: Thanks for your note and readership. Congrats on the sale. I dealt with the “directionless” feeling here and there. The trick was to keep exploring without necessarily knowing what you’re gonna do next.

      A few examples of what I did:
      1. Attended IT events outside my “comfort” zone. I had spent a decade at channel events. During my time away from the market, I went to IT and business events focused on big data, Hadoop, venture capital, etc. None of it was core channel — but there were always partner angles that popped up.
      2. Hung out with an Angel Investor Group. In my case it was Golden Seeds in New York.
      3. Never missed a chance to see my kids in a sport, in a play, in a concert performance.

      Roll all that together and what do you get? I basically discovered I wanted to do something in IT that shows entrepreneurs what’s next, how to build more profitable businesses, and how to ultimately afford to spend more time with your families. Hence, ChannelE2E.

      I don’t know what you’ll discover. But definitely go to events that are outside your traditional focus area. And keep me posted. I’d love to hear how you’re doing and what you’re doing. [email protected].


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