the asymmetric life
what's an asymmetric life and why you're just $5 away from living it.
sometimes the universe whispers.
other times it shouts.
this time it was shouting.
between bites of pizza, i lamented to andrew (fellow man of the ‘sletter) that i felt i wasn’t taking full advantage of new york.
if you’re paying $3500 for a shoebox you better be getting more out of the city than just feeling in on the latest nolitadirtbag meme.
the talent pool in new york is bar none. your proximity to greatness is unmatched by any other city.
shouldn’t i take advantage of that?
there’s this concept i love—it’s the idea of the asymmetric life1.
speaking at stanford, graham weaver reflects on his 29-year career as an investor,
if i had to summarize great investing in a single word, it would be “asymmetry.”
seek opportunities where the possibility of gains wildly outweighs what you can lose, which is typically capped at 1x your investment.
you’re not playing for a 1.5x or 2.0x outcome, you could be playing for a 10x, 20x, or even 100x outcome.
…
as i started applying the principle of asymmetry to investing, i also began to realize that the principles were even more powerful when i applied them to other areas of my life. and just like in investing, i was playing small in my life — playing not to lose.
playing not to lose. that’s how i felt.
what’s a fella to do?
only one answer…
send more cold email.
as far as bets go, i can’t think of anything that’s more asymmetric than firing off a cold email.
takes you, what, 5 minutes to draft and send?
downside: wasted 5 minutes
upside: a great conversation, a new best friend, a lover. if you’re lucky—all three.
something about our convo must have struck andrew, because our imessage thread quickly turned into a cold email circle jerk.
that final one tipped the scale.
the challenge was on.
but we needed a little skin in the game.
and tadzio cometh to collect:
”life-changing” is pretty overused.
but it applies here.
send one cold email a week for a year (52) and there’s zero chance it doesn’t shift the trajectory of your life, even slightly.
the first person on my hit list was adam robinson.
i heard him on an interview 7 years earlier. that interview changed my life (no, really).
then the other day while researching a piece, i happened to look him up.
his twitter says he lives in williamsburg. i’m in greenpoint. we’re neighbors?
fuck it.
after crafting the ~perfect~ email, i tracked down an old email of his and fired it off.
5 minutes later my email client showed he opened it.
*refresh, refresh, refresh*
nothing.
…
still nothing.
to be fair, the guys got better things to do…
he’s advisor to your fav hedge fund billionaires
founded the princeton review
chummy pals with warren buffet
but i wasn’t done.
a week later i hit him on IG DMs.
moments after i see “typing…”
queue anxious excitement.
quick—close the app before he sends and the read receipt shows.
10 minutes later—after i’ve given his message sufficient time to marinate—i reopen the app to see what awaits.
oh shit, his direct number !
i schedule a coffee chat before he’s got a chance to reconsider.
well that 20 min chat turned into a 2.5 hour chat.
and doggone it, the motherfucker did it again—changed my life for the second time.
but…
there’s no one i want to connect with.
nonsense.
if you consume media, there are people whose thoughts you enjoy. start there.
go through your newsletters, fav podcasts, books, etc and make a list of the ones you enjoyed the most.
you can even do it with folks on social, though i’d avoid folks with above 100k followers.
but i don’t live in nyc.
well i’m back in oregon now.
touching grass.
and hosting our annual lobster club residency.
in fact, i’m writing this from the middle of a forest.
but i’m still sending my weekly cold outreach.
so if you’re not in new york city, you’re not off the hook.
in an era of zoom, distance is no excuse. obvi meeting IRL is the gold standard—though you shouldn’t always go straight for the kill…
it took me embarrassingly long to realize this—a cold outreach doesn’t need to have an ask attached to it.
many of the best ones don’t.
they’re a simple—hey i appreciate what you do.
sometimes that’ll be the end of it.
other times it’ll be the start of a beautiful relationship.
a few tips:
reply to newsletters!
despite having worked in email for years, i still forget that you can respond to newsletters. when i do, i’m always surprised by how often i get a response. try it.
any time you consume a piece of media you like (podcast, video, essay), take 30 seconds to send them a note saying you enjoyed it. try to be specific about what resonated. you’ll make their day and you might get a few new friends out of it.
keep it short and to the point — this template from alex banayan is a decent place to start:
1st line:“i know you are very busy and get a lot of email so this will only take 60 seconds.”actually, this is probably a terrible way to start a cold email. i’d skip it.2nd line: 1 or 2 sentences about who you are and how that’s relevant to the person you’re contacting.
3rd line: 1 or 2 sentences with a specific question (should show that you’ve done your homework) the recipient can answer quickly.
4th line: “i totally understand if you’re too busy to reply. even a 1-to-2-line response will make my day.”
get some skin in the game.
ask a pal to be your accountability buddy & put $5 on the line for each time one of you doesn’t send a cold outreach that week.
editor’s note: halfway through this piece i realized something—i only know andrew because 3 years ago i sent him a cold DM. in fact, the kid blew me off twice. a few reschedules later, i reluctantly agreed to meet him at a pub in mexico city to catch a world cup match (for those that don’t know—tadz hates televised sports). look at us now—monetarily, i’m at least $5 richer than i would be otherwise, and richer in non-monetary ways many times over.
send the damn email.
talk soon,
-t
gorgeous. i needed this. i absolutely love the message and principle here. especially the part where you mention there's no chance regularly sending cold outreaches doesn't change your life. also love the part where you mention they don't need to necessarily have an ask attached to it. so many cheers to this practice of, ultimately, courage and making our voices heard
really enjoyed this. i think we forget people appreciate validation as well, even if they dont need it!!