Writing the book (a book?) on what exited entrepreneurs do with the rest of their lives. (Also, AI compliance).

Joined December 2008
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I like that I can easily use the heuristic of instantly discounting any tweet starting with "This guy literally dropped." Saves a lot of time.
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2 Aug 2025
The flip side to “every generation thinks the last one is lazy” is “every generation thinks they have it worse than anyone in history.”
1 Aug 2025
If I we’re 20 years old in 1945 there’s a chance I’d have 4 confirmed kills in the Pacific Theater. Each generation carries a burden. But man we do have it good today compared others.
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6 Apr 2025
There is an expensive seminar somewhere that must be teaching all these people to call common knowledge “brutal truths.”
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6 Aug 2024
Investing in search funds and #smb is a phase for basically every post exit entrepreneur I’ve interviewed. Use that information wisely.
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1 Aug 2024
I’m starting all of my tweets from now on with “I won’t punch down.” Amazing power move
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28 May 2024
I grew up in Topeka and we definitely thought this
😳
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10 May 2024
I saw someone with "last exit $xxx" in their profile. They had started a small startup which sold to a larger startup, which then sold to a public for, you guessed it, $xxx. If you have to exaggerate the size of your exit, something has gone wrong inside.
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9 Feb 2024
Me posting memes to my text chain
A young Shaquille O'Neal shatters a backboard, 1993.
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6 Dec 2023
This is exactly right. We either believe in free speech on campus (and the right for faculty and students to say awful things) or we don't. The problem is that universities have gone out of their way to control speech in every other context.
As a professor who favors free speech on campus, I can sympathize with the "nuanced" answers given by U. presidents yesterday, about whether calls to attack or wipe out Israel violate campus speech policies. What offends me is that since 2015, universities have been so quick to punish "microaggressions," including statements intended to be kind, if even one person from a favored group took offense. The presidents are now saying: "Jews are not a favored group, so offending or threatening Jews is not so bad. For Jews, it all depends on context." We might call this double standard "institutional anti-semitism." University presidents: If you're not going to punish students for calling for the elimination of Israel and Israelis, it's OK with me, but ONLY if you also immediately dismantle the speech policing apparatus and norms you created in 2015-2016. Please read The Coddling of the American Mind. @glukianoff and I laid out exactly where the oppressor/victim frame came from (ch. 3), how it spread out of a few departments to gain power over administrators and campus culture (chapters 4 and 5), and how it drove the creation of the bureaucratic structures and processes that now have us all teaching and learning on eggshells (ch. 10). In chapter 13 we offer advice to leaders on how to to return universities to their academic mission and regain public trust.
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1 Dec 2023
My 6 year old son asked for "a security camera on wheels with a remote control" for Christmas. I asked ChatGPT, it went to Walmart.com (?) and figured it out instantly. Amazing.

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16 Oct 2023
Someone is going to make $1B if they figure out how to make anxious parents pay to make their kids more “free range”
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14 Sep 2023
This must be the absolute most brutal business to operate -- pickups for seniors, sitting on top of Uber/Lyft. So glad someone other than me is taking this on!
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5 Sep 2023
One thing that's really hard and surprising for second-time entrepreneurs is to see a project fail. After the combo of hard work get lucky the first time, they expect the luck to continue. Often, it doesn't. Part of the reason is that second-timers often choose a much harder business the second time around -- less proven demand, worse cash conversion cycle, higher upfront investment.
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27 Jul 2023
One reason that I don't care about being a billionaire or whatever is that I don't think I can donate to charity more than whoever my "replacement would be." And I place negative value on sneaking my name onto buildings etc.
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24 Jul 2023
I just had a VC backed competitor steal my copy -- like very nearly word for word, same bullet points, same language. Cease and desists are boring. How can I respond in a way that's maximally entertaining for me?
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10 Jun 2023
Which of these obviously Christmas wrapping paper choices looks most like a child birthday? The eternal struggle
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25 May 2023
I’m willing to bet tweets about buying a cash-flowing business with no money down literally outnumber the sum total of completed no money down acquisitions in all human history,
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9 May 2023
Hot take: W2 is a lot easier on marriages compared to entrepreneurship / #smb Incredibly hard to do a good job at both business building and family life, which both, at times, need to be all-consuming.
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13 Apr 2023
For all you smarties out there, no correlation between intelligence and happiness, and strong negative correlation between large vocabulary and happiness. This tracks with personal experience -- smart people choose ambitious projects and constantly strive.
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