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Life After Selling Your Business. The Good, The Bad, and The OMG, What Did I Just Do?

  • December 30, 2021
  • 35.8K views
  • 6 minute read
  • Jeff Wiener
life after selling your business
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And just like that, with one final signature, I changed the course of my life.

I didn’t come to the decision to sell my company lightly, but rather, it was a decision I made in January of 2017 when I realized that I had many unaccomplished goals and that I was still young enough to accomplish those goals. And with that fateful decision 16 months ago I started down the path of figuring out how to divest myself from my company

It’s easy to get into a routine of complacency, and after 26 years I was in that routine. Yes, business was good, and yes, for the most part, I loved what I did. Running my company was never a job, it was always a passion. My passion has always been to build a business. And that passion took us to 50 people strong.

And then I realized that there’s more to life after selling your business, and many unfulfilled passions.

So what’s next?

Life After Selling Your Business

Signing the Paper Work to Sell My Business
Signing the Paper Work to Sell My Business

I stepped down as President of my company at the end of December 2017. January 1st, 2018 marked my first day on my new journey. My first day as officially “semi-retired,” or “unemployed,” or whatever else you call it when you’re transitioning to something new.

When I started my business in 1991, I certainly didn’t think I would be running the same company for 27 years. And for 26 of those years, I thoroughly enjoyed the challenge of scaling a business. I decided that it was time to move on because I wasn’t excited by the prospect of growing the company any longer, I had enough to retire and decided that I was at the stage of life where I was ready to try something different.

Oh No. I Just Sold My Business. Now What?

My first day post-sale was bittersweet. On the one hand, the challenging M&A process was over, I had the cash in the bank, and I was excited by the opportunities that lay ahead. 

On the other hand, what I thought would be an easy personal transition was anything but. Little did I realize how much my identity, of who I am as an individual, was wrapped in the business and in my relationship with my contacts, customers, team members, and suppliers. 

You can read many books, articles, and blogs, and listen to many podcasts about a particular subject, but often, until you experience something for yourself, it’s difficult to appreciate what’s in store.

It Can Get Lonely Once You Sell Your Business

The silence of solitude can be deafening at times, especially considering how busy I was when I was President. My identity was wrapped in my role, and I lived it for so long, it was difficult to appreciate what life after selling my business would be like once that responsibility was no longer there.

Lonely after selling your businessI am an entrepreneur at heart, and while I am now a minority shareholder, the responsibility is different and I find myself missing the activity and excitement of scaling a company, of having people lined up at my door, of the exhilarating feeling of making quarterly and yearly sales forecasts and the feeling of accomplishment for meeting short- and long-term strategic goals.

What I have come to realize about myself is that I am an entrepreneur on the hunt for the next opportunity. Entering into entrepreneur semi-retirement has come as somewhat of a shock.

While having the money in the bank might buy some comforts, it’s difficult to replace the human interaction and excitement that comes with running a company. I don’t regret my decision. The huge advantage of leaving the business rat race is that I get to focus all of my energy on doing what I really want to do.

I began my new business venture on Monday, January 8th, 2018, and although I wasn’t entirely sure what I was going to do, I did know that my next gig was going to involve helping entrepreneurs, in some way. 

It’s now been over two years since I sem-retired, and although the initial few months post sale were a shock, I’ve comfortably settled into a new life of working with a couple of clients doing some ad-hoc consulting, sitting on two boards, one for profit, the other not for profit, writing for this blog, managing my real estate and private investments and portfolio, and doing a lot of traveling. You can read about my portfolio allocation and performance here.

I started and finished writing a 60,000-word book, and published a smaller book on investing for entrepreneurs which you can download for free here.

What to Tell Your Employees When You Sell Your Business?

The day I announced to my team that I decided to step down as the company President, I said the following quite appropriate quote: “20 years from now you will be disappointed by the things you didn’t do than by the ones you did. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.”

And just like that, with one final signature, I changed the course of my life.

Are You Considering Selling Your Business? 

In the last two years since I sold my company, I’ve had the opportunity to speak with at least two dozen other entrepreneurs who have also sold their businesses.  The good news is that, of all the people who I have spoken with, none have regretted their decision, although, some are struggling with life after selling their business.

Jeremy Greven
Jeremy Greven

Some of these entrepreneurs are now running angel investment firms. You can read about two of them here:  From Missing Payroll to a Successful Exit and Now 17 Time Angel Investor. An Interview With Entrepreneur Jeremy Greven, and here: 5 Big Mistakes Founders Make When Pitching for Venture Capital for Their Seed Round

Some are waiting on the sidelines trying to figure out what they’re going to do next. They’re taking a lot of vacations, having the occasional meeting, and it seems, buying time.

In most cases, of the entrepreneurs who I know, all of them have enough money to never have to work again, but, they choose to continue working, or, keep busy because you can only play so much golf and hang around the beach or pool for so long.

What do you do with your life when you have so much money that you don’t have to work?

You need a bigger purpose in life, and the purpose needs to transcend making more money. Not having to work for money, and having enough, is a hard concept to grasp, especially if worrying about not having enough has been in your entrepreneurial DNA for many years.  

You come to define yourself as an entrepreneur, and as someone who has worried about payroll, keeping customers happy, staff engaged, and the lights on for many years, and you don’t change who you are, fundamentally, just because you sold your business.   

Most entrepreneurs are hard-driving, ADD, assertive individuals who know how to get what they want. That doesn’t change just because you’ve sold your company.

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You should also consider subscribing to my blog. I publish one article a week on small business and wealth creation.  You can subscribe here.

Also, I published a book during the summer of 2018, “The Kickass Entrepreneur’s Guide to Investing, Three Simple Steps to Create Massive Wealth with Your Business’s Profits.” It was number 1 on Amazon in both the business and non-fiction sections. You can get a free copy here.

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  • What to Know About Selling Your Life Insurance Policy
  • How to Live a Good Life as an Expat in the UK
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  • How To Find A Good Business Vehicle: A Guide
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Jeff Wiener

Jeff sold his company to private equity in 2017 and is now semi-retired. Jeff spends time traveling and with his family, writing this blog, managing his real estate portfolio of apartment buildings,  overseeing his investment portfolio, investigating angel investments, coaching other entrepreneurs, and managing his private equity holdings. Jeff is currently on a couple of boards, one for profit, the other not for profit, and now helps entrepreneurs grow their business, profits, and ultimately, create wealth.

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