exec coach · helping founders build companies they can be proud of with partners who truly have their back · alum meta etsy yc stanford
Brooklyn, NY
Joined October 2006
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just realized attachment theory applies to every relationship -- including the one with your ambition:
anxious ambition: "i have to succeed to feel ok"
avoidant ambition: "if i don't try, i can't fail"
secure ambition: "i want success, but failing won't kill me"
"i don't have it in me to do another fundraise" - me in 2020
a hard convo with my cofounder on the highline after 3 years of pivoting
we decided to take the fb offer soon after
too many founders dodge hard convos—bc they're scary
sharing feelings that shatter the your carefully developed mask
"i won't respect myself if we can't raise a series a"
reframe: confronting the truth lets you act with greater internal alignment
confronting info you may not want to hear
"i don't trust you as much as used to"
reframe: you can't fix bugs you can't see
getting hurt or hurting others
"shit that's not what i meant"
reframe: repairing makes your partnership stronger
facing tough tradeoffs btw multiple valued outcomes
"growing the team means i won't code as much"
reframe: saying it outloud means you can model the optimization curve
some days i regret taking the acquisition
but mostly i regret all the hard convos i never had
met up IRL with the most cracked founders in SF
concluded that the level of trauma required to build generational companies out here needs to be studied
The idea that deliberate practice in writing is actually about rewriting hits different when generating reasonably smart text is basically free and instantaneous.
When you tell VC that the round is almost oversubscribed but you could squeeze them in at a 15% markup.
Named 100 women in 19 minutes. I know that sounds bad but I'm going to blame it on the lateness of the hour.
Really great game by @katiewav
Second to last Q&A - an easy one: what’s your mission in life?
“Increase the distribution of good ideas in the world.” @JamesClear
“Give creators and people everywhere the clarity and tools to reach financial freedom.” @nathanbarry
#craftandcommerce
Atomic Habits is has been the best selling books of the last 5 years.
To explain its incredible success (30M copies sold!) James Clear shared one great story about obsessing over quality:
The first sentence of every chapter is a crucial chance to hook readers.
To write the most compelling first sentences, James hired a programmer to scrape the most read / emailed articles on the New York Times for 30 days to pull the first sentence of those top articles into a spreadsheet.
He would then look at that list of 200 different first sentences to help craft his chapter openings.
“Half of the success of a book is the category, the title and subtitle, the cover itself,” he said.
“And the other half is a 1000 little details like the first sentence of your chapters.”
In this era of AI slop, I think this story is so important. The speed & volume enabled by technology is amazing, but there are many places where human obsession still matters more than anything else.
(Little snippet from my first time at Craft & Commerce)
Jason Shen · The Outlier Coach retweeted
Every person has a story to tell, and AI can help them tell it.
We're seeing this firsthand at @typedotai. We now serve writers ranging from NY Times bestsellers, to top 10 podcasters, to nearly 10k passionate independent authors.
We've been ~doubling revenue each quarter and active subscribers now spend 7+hours/week in our editor.
So we made this video to honor the intensely creative people we serve. Here's to the storytellers :)
1/ Most cofounder fights aren't about what they're about.
After 18 months of coaching cofounder pairs, I've found the same hidden pattern underneath almost every recurring argument.
I call it Old Wounds and Old Ways. 🧵
10/ No challenging. No "buts." No problem-solving.
Just: "I hear you. That sounds painful."
That's it. That's the whole exercise. This is how I came to understand my wife's experience.
It works because for the first time, each person sees why the other reacts the way they do. The fight stops being about the deadline. It becomes about the person.