Why do all sketchy founders dress sorta weird?
And that is absolutely not where you put your coffee...
Hello Gobbledeers,
How’s it going?
Before we start - thanks to the fine folks at Really Good Emails for having me speak at their Unspam conference this week (I’d be happy to speak at your conference, too!). The event was in Greenville, SC, and if you’ve never been there before you should cancel your trip to Savannah or Charleston and go there instead. It’s just an amazing little city.
With that out of the way, today we’ve got:
A possible answer to the mystery of who may have been behind that terrible chief of staff job posting
Using a pair of shorts to scam people out of $40 million
Where you shouldn’t put your coffee mug.
A Mystery Possibly Solved?
You may remember that last week we had a fun discussion about a Chief of Staff job opening that a recruiter posted.
For our new subscribers, the thing you need to know is this part of the description that talks about the founder that the chief of staff would be supporting:
“Currently, he runs five fintech businesses in various stages, generating hundreds of millions of dollars yearly... He is a very big thinker, always looking to evolve and learn. He is self-made and self-taught. Never went to college. He is crazy about learning.”
Also you should just read the whole thing, it’s amazing.
Just park that info in the back of your mind…
I was recently reading this bananas article about Ryan Breslow, the founder of a fintech something something called Bolt that at some point was worth $1 billion and now is, uh, not worth $1 billion, and Breslow also may have used $30 million of Bolt’s funds to pay some of his own debts.*
(*The law tends to frown upon this type of activity.)
After years of reading articles that had the thesis statement “listen to how batshit crazy this founder is” you might think I’ve grown tired of reading about batshit crazy founders.
I have not. And this article does not disappoint:
First sentence? “Ryan Breslow was dancing barefoot in a geodesic dome when his investors sued him last July.”
Why was he in the geodesic dome? “Breslow was headlining a mindfulness retreat centered around dance and “the pursuit of happiness.”
After Bolt’s board confronted Breslow about the $30 million, “Breslow installed three new directors — all of them friends. They included Grammy-award winning producer Larrance Dopson, journalist Esther Wojcicki (mother to Susan Wojcicki and “Godmother of Silicon Valley”), and The Mighty Ducks child actor and crypto investor Brock Pierce.”
“Florida court records viewed by Forbes show that a month [before raising funds at a $1 billion valuation], he changed his middle name to “King.”
“Party photos show Breslow splayed out on a tie dye mat, while a sound healer plays Tibetan singing bowls on his stomach.”
“By February 2022, he had cofounded four companies, all while remaining Bolt’s CEO. There was Movement DAO, a blockchain community project; Love Health, an online wellness marketplace; The Movement, a dance nonprofit; and the lending platform Prism.”
It is here that - if Substack offered the functionality - I would make that record-scratch sound that they use in movie trailers when you find out the wacky twist (the dog is the CEO of the company!).
That last part. That last part sounds familiar. “He had cofounded four companies, all while remaining Bolt’s CEO.”
Four companies + one company =
Holy crap, five fintech companies!
“Breslow had personified Silicon Valley success with an archetypal story: a public school kid who dropped out of Stanford University…”
Never went to college!
Self-taught!
“He’d also self published two instructional playbooks, Fundraising and Recruiting…”
Crazy about learning!
Is Ryan Breslow looking for a Chief of Staff??????
Now I kinda want to apply…
Last Call for Your Free Gift from Postal
Our friends at Postal don’t need a new chief of staff, but they HAVE been kind enough to support the Gobbledy Newsletter because while THEY know that there’s no better way to send gifts to prospects and customers, they also want to make sure YOU know that.
And because they also know that everyone loves gifts, they’re going to send you a fun gift box, no strings attached* if you sign up and get a demo of the platform.
(*Well, actually there are a few strings. They’re the same strings as the last few weeks - but that hasn’t stopped a whole bunch of you from deciding you wanted to learn more about Postal - you should! Anyway, they want 30 minutes of your time to show you why Postal is better than whatever you’re using now to send things (think corporate gifts, wine, food, or any of those “cool” branded items your CEO wants you to make that are sitting in the back of your utility closet).
And if you’re NOT using anything to send gifts, you’re in for a treat when you see how easy Postal makes it to send gifts.
GET YOUR DEMO OF POSTAL AND A FREE GIFT
Repositioning While Also Not Repositioning
I mean, yeah, sure, it’s now “for barnyard animals that are kinda cranky, Axe Body Spray is the only fragrance that will improve their emotional state and attraction to sexual partners by up to 18%” but also, kinda, that’s sorta what it was before?
Everything Is Positioning, Fly High Duluth Edition
Longtime Gobbledy readers may remember that sometimes we talk about how “Everything is positioning.” And I know that that’s maybe being a little flippant. Not everything. But like, many things? Or really, it’s more that Anything CAN be positioning.
One of my favorite unexpected positioning opportunities is how founders dress.
If you wanted to go out to Silicon Valley and raise some cash money back in the early 2010’s, you may have untied that tie, put on a hoodie, and then flown to San Francisco and asked guys* for $75 million.
(*Yeah, they weren’t ALL guys, but also they were all guys.)
Those guys weren’t wearing hoodies. They were wearing Allbirds. The guys giving out the $75 million wore Allbirds to suggest/imply that they’re guys who don’t JUST care about tech, they also care about how they look, and also maybe (?) they invested in Allbirds, and look how well rounded and smart they were for that!**
(**Until recently.)
So they were positioned as well rounded fellows who also are successful, unlike those stuffy East Coast banker types who wear vests.
The hoodied guys*** asking for the money were hoodied because they positioned themselves as “too focused on building products to care about dressing themselves.” Dressing well suggested they were wasting the investors’ money, and certainly THESE founders weren’t going to do that.
(***ibid)
We’ve talked about FTX’s Sam Bankman-Fried and how he successfully positioned himself as “unlike other crypto guys, I just don’t give a shit what anyone thinks about me, which shows how certain I am that what I’m doing is the right thing, which makes investors feel like this guy is SO certain he’s correct that I need to invest in him.”
SBF accomplished that by dressing like a homeless person and playing video games while doing TV interviews, and - more importantly - making sure everyone knew that he was dressing like a homeless person and playing video games while doing TV interviews, which is how people knew just how much of a shit he didn’t give, which showed HOW certain he was correct, which created FOMO among investors, etc.
I’m mentioning all of that, because of this Bloomberg article about Patrick Britton-Harr, the founder of “private jet club” Aeroventi, which is now accused of probably (?) taking/stealing/misappropriating/diverting/something the $40 million that people paid him to join his “private jet club.”
The description of Britton-Harr in the article is a greatest hits of founder positioning:
Britton-Harr, a self-described serial entrepreneur…founded AeroVanti in his late 30s. Wide-shouldered and big-jawed with short-cropped hair and a beaming smile, he communicated with the quick, confident diction of a QVC host. Fluent in boardroom jargon, he could sound like an artificial intelligence program trained on corporate PowerPoints. He preferred fist-bumps to handshakes. Most often he came to work wearing shorts, flip-flops, a visor, dark aviators and a Rolex.
If I wanted to scam a bunch of people out of $40 million (and I’m going to be honest with you, once I’m scamming people out of $40 million I’m definitely scamming them out of more than $40 million), I would follow that playbook:
“Communicate with the quick, confident diction of a QVC host”
Become “fluent in boardroom jargon”
Sound like “an artificial intelligence program trained on corporate PowerPoints” (ed. note: how is this not a thing yet?)
Offer my scamees fist-bumps instead of handshakes, to show that we’re buds
Wear shorts, flip-flops, a visor, dark aviators and a Rolex to the office
That last bit - dressing like a slob but also wearing a Rolex - positions himself as the guy who has already been so successful that he can both afford a Rolex and dress like he doesn’t give a shit, and why would THAT guy steal $40 million of your dollars? (Answer: Because he can.)
What’s Wrong with This Picture, Not Marketing Related Edition
We’ll play a quick game here at the end…what’s wrong with this picture, sent to me by longtime reader and also relative Jeremy B:
I did provide a hint…
Have you had a moment to guess?
Yes, the answer is that when you are sitting in first class and you take off your shoes like an animal (who uses Axe Body Spray to relieve grouchyness), you should stick your coffee holder inside your RIGHT shoe, not inside your left shoe. Removing your shoes and sticking your coffee cup inside your left shoe is considered uncouth.
As always, thanks for reading to the end.
I really, really enjoy chatting with readers, which is why I include a link to sign up for a 25 minute chat: Here’s my Calendly link. How do these usually go? We’ll spend 5 minutes BS’ing, then 20 minutes going through your site and you’ll get some ideas about how to make it better. Why wouldn’t you sign up for that?
And lastly, I’ve been doing a bunch of workshops around messaging, and the outcome is that your homepage will be SO much clearer. They’re 2 days. In person is best. If you want your homepage to be clearer, we should chat. You can reply to this newsletter, use that Calendly link, or email me at jared@sagelett.com.
And lastly lastly, if you want to reach an audience of marketing people, you can do no better than advertising in Gobbledy. That native ad above was pretty good, no? (Everyone loves humility.) Anyway, if you want to reach an engaged audience of marketing people, let’s chat about advertising opportunities. I’m still at jared@sagelett.com.
Argyle socks?