Yes, the blog is still called that. I named it before I knew better.

Getting what you want doesn't stop the wanting.

I spent 27 years building a company, sold it, and found out nobody warns you about what comes next. Since then, I've watched peers who caught much bigger fish than I did go right back to chasing, most of them worse for it. A heart attack didn't end the chase. It just changed the questions. I'm writing it down, in case you're chasing something too.

Jeff Wiener.
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Eleven chapters. Read in order. About an hour.

Jeff Wiener

Toronto · est. 1991, still figuring it out


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It's one story. Read it in order.

The sale 2017 Chapter 1

The Day After Selling Your Business

Checking email every fifteen minutes for problems that no longer came. I wasn't waiting for a message. I was waiting for the feeling I'd mistaken for purpose.

02 The building years 1991 Down to My Last Five Hundred Dollars Six months in, five hundred dollars left, grad school applications open. Then, on a drive to the bus station, my girlfriend said: you know what you could try? 03 The building years 2000 The Year I Lost Sixty Percent A bull market I mistook for skill. The crash took sixty percent and a company I loved, in the same year. 04 The building years 2008 The Week the Bank Pulled My Loan Lehman fell on a Monday. My financing vanished the same day. I bought the building anyway. 05 The building years 2004 The Things I Never Told Anyone A letter read to me over the phone in Greece ended our Nortel dealership. They were one hundred percent of our new business revenue. There was almost nobody I could tell. 06 The building years 2013 The Day My Best Employee Quit My best employee quit and told me the truth on his way out: the ceiling on the company was me. 07 The sale 2017 The Six-Hour Walk I went to the beach to plan how to double revenue. I came back six hours later having decided to sell. 08 The sale 2017 The Year I Was Gone But Not Gone Everyone was in the room. I made the announcement. And I knew that face, because I'd worn it as a kid. 09 Looking back 2018 A Letter to My Daughter About Money The money talk I flew across the country to give, and the lesson my daughter gave back. 10 Now 2023 The Day the List Reordered Training for a championship at 55 when a blocked artery called time. Five minutes, two wakings, and a list that finally flipped. 11 Now 2026 Success Solved Everything Except the Important Questions Two more companies, one heart attack, and a reordered list. The honest accounting, nine years out.