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The Kickass Entrepreneur
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Retirement

16 posts

The Life of a Retired Entrepreneur

Now that I’m semi-retired, I spend my time traveling and with my family, writing this blog, managing my real estate portfolio (I have a property manager and controller), overseeing my investment portfolio, looking at angel investments, coaching other entrepreneurs, and managing my private equity holdings. Oh, and I’m also on a couple of boards, one for profit, the other not for profit.

I write about all of these things on this blog.

Entrepreneur Semi-Retirement
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My Three Year Semi-Retirement Winter 2021 Check-in

  • January 2, 2021
  • Jeff Wiener
Remember me? Yes, it’s been a while since you’ve heard from me. I haven’t written a blog post since September – that’s almost four months of not connecting. So what…
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When to Sell Your Business
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How Do You Know When to Sell Your Business? It’s Not All About the Money

  • December 19, 2020
  • Jeff Wiener
You can listen to this episode on my podcast here:   I sold my business in October 2017. It took the better part of a year to figure out what…
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life after selling your business
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Life After Selling Your Business. The Good, The Bad, and The OMG, What Did I Just Do?

  • November 20, 2020
  • Jeff Wiener
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…
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passive income
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Building Wealth Through Passive Income and Business Ownership

  • September 29, 2020
  • Jeff Wiener
This article is about two things that are closely related.  Generating wealth through: passive and residual income, and through small business ownership. One of the things I’ve written extensively about…
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Semi retired at 50
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Semi-Retired at 50. An Entrepreneur’s Life Post Business Sale. My Summer 2020 Check-In

  • June 27, 2020
  • Jeff Wiener
That was an interesting six-months indeed. That’s how long it’s been since I wrote my last personal update, and it’s now been almost three years since I sold my business,…
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Early Retirement
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Semi-Retired at 50, Traveling, and Enjoying Life. My Winter 2020 Check-In

  • December 12, 2019
  • Jeff Wiener
Just for fun, I added some travel pictures throughout this post. October 17, 2019, marked the two-year anniversary since the sale of my business, and since I semi-retired at 50.…
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Jeff Wiener Semi-Retirement Update
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Entrepreneur Semi-Retirement. The Life of a Semi-Retired Entrepreneur [Summer 2019]

  • July 16, 2019
  • One comment
  • Jeff Wiener
It’s hard to believe that it’s been over six months since my last update. It’s also hard to believe how much has happened, both on the work front but also…
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Retired Early
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How to Retire Early. Here’s How Much You’ll Need and How To Get There

  • July 9, 2019
  • Jeff Wiener
In one of my favorite financial books, The Millionaire Next Door, the author, Thomas Stanley, coins the phrase, “big hat, no cattle.” The term describes an individual who, by all…
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Jeff Wiener, Semi-Retirement
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My Eleven-Week Experience Running a Business as Interim President. Semi-Retirement on Hold!

  • June 18, 2019
  • Jeff Wiener
I stepped into a new role on March 27th of this year as the interim president of the company I sold in 2017. Semi-Retirement was on hold for a period…
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Another Chance at Bat As I Step Back Into a Management Role.

  • April 2, 2019
  • Jeff Wiener
If you’ve been following my blog from the beginning, you will know that I stepped down as president in December 2017 of the company I founded in 1991. In a…
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Jeff Wiener
Jeff Wiener
Jeff sold his company to private equity in 2017 and is now semi-retired. Jeff spends time…

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