Founder/Chairman @grainhq | 3x co-founder (prev: @missionu @degreed)

California
Joined December 2011
Today, I'm announcing @appy_ai - backed with $5M from @dschol & @fcollective Now, anyone can vibe their idea into a entire AI *business* in minutes. I may be having fun, but I'm 100% not kidding
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Just had 10 fire trucks rip up my street in Laguna Niguel… Apparently someone with no awareness started a fire in their chimney and it collapsed. Fire crew was right on it, looks likely they’re gonna contain it. But WTF people? Can we plz just not start any fires for a bit?
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Enjoyed some start-up real talk with @berman66 (Nanit, Vowel) & @kevingibbon (Shyp, Airhouse). Thanks for having me on the @SecondTF_pod
E53 w/ 3rd time founder @michaelglena on all his learnings including AI and choosing to step down from CEO Guest @michaelglena (Degreed, MissionU, Grain) Hosts @berman66 (Nanit, Vowel) @kevingibbon (Shyp, Airhouse) Listen, subscribe on all podcasting channels or watch on X!
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E53 w/ 3rd time founder @michaelglena on all his learnings including AI and choosing to step down from CEO Guest @michaelglena (Degreed, MissionU, Grain) Hosts @berman66 (Nanit, Vowel) @kevingibbon (Shyp, Airhouse) Listen, subscribe on all podcasting channels or watch on X!
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How to define a “pivot”: Anytime you substantially change the way you answer the question “what does your company do?” when asked by someone outside of your industry. By that measure @GrainHQ had pivoted at least 7 times over the past 5 years.
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5 year Carta customer w/ @GrainHQ Unbelievably bad comms from @henrysward This “woe is me” mindset is mind-boggling. Admits Carta “fucked up” but then proceeds to blame @karrisaarinen for the way he exposed it. Own your mistakes. Period. Only way to re-built customer trust.
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Similarly, nobody regrets hiring too slowly and methodically. Much better to never hire than have to fire.
Have yet to meet a founder who regretted cutting too deep.
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Just had a "glitch in the Matrix" moment: Opened a vendor's proposal in Notion Doc had an embedded vid of "Let's Go" by Trick Daddy That exact song that was actively playing on random shuffle of a random playlist in Spotify Had never heard that song even once before... wtf?
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Startups/founders think of themselves/teams as elite athletes… but then the prevailing advice is to ignore the other team? Sure, good advice to get your house in order if you’re at the bottom of your division. But you can’t expect take 1st without studying your opponents.
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Sad to see, good folks with smart things to say. If this doesn’t make one question the freemium/PLG thesis as viable mainstream strategy I don’t know what will.
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I just entered the “my 10 year old just did math in his head that I thought was wrong until he explained it to me and I realized I was wrong” phase of parenting. What’s next, beating me in the 100 yard dash? Not so fast!
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Before I lived in SF for 10 years, my only exposure to the city was from Tony Hawk Pro Skater 2. Incredibly fitting to see they cleaned up the tent camps for a skate park. 👏
There was a lot of opposition to this skate park at UN plaza in SF; it isn’t perfect but undeniably better to have people skating, working out, playing chess, ping pong and cornhole than the open air drug market that was here 1 month ago. Major kudos to the city for getting it done so quickly.
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When WeWork acquired my start-up in 2018 I got options "worth" $300k @ $47B val but never exercised them. w/ the bankruptcy, I was curious if at sometime I ever had a viable exercise/sell window. Let's break down the cap table math by option grant dates from '11-'19👇 /1
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Many "early exercisers" (buy stock & pay tax before liquidity) took cash losses even if sold @ peak liquid val in '21 Series B emp. w/ 125k shares: -'19 paper val: $6.6M (@$47B val) -'19 exc. cost+tax: ~$2M -'21 liquid val: $1.4M -'21 cash loss: -$600k -'21 paper loss: -$5M /6
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Bad cap table math has actually cost me millions.. So learn the hard way by losing $ w/ bad assumptions like I did... Or learn the easy way by getting the data you're missing and do scenario modeling. And if your co won't give you the data, consider running for the hills...
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As a kid in UT during the 90s housing boom I had access to unlimited scrap wood for tree houses. Building became core to my identity. I asked my 10 y/o son if he likes UT or CA better, he said: “In Utah there are so many boys and I could build so many treehouses.” 😭
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