Questioning Dorsey

I know we don’t talk a ton here about the character of leadership, that accelerating growth rates, expanding margins, excellent retention rates, giant moats and TAMs do the talking, but I have to wonder if the Sarah Friar departure is worse than we at first thought/think. FWIW, I am a SQ shareholder.

With Jack’s latest antics meditating in Myanmar and Tweeting about the “joyful” people, Friar’s departure irked me again, so I did a little research. I would have let this go, because I hate to pull the board into the “squishy” (non-math) areas, but these articles, as a whole, raise legit questions about Dorsey’s judgment, leadership, communication skills and even his character. So I felt worth sharing for your own consideration. For me, as as shareholder, I don’t like any of this, not one bit:

It sounds like Jack Dorsey really mailed his beard to Azelia Banks…

Explaining that, having written a book about Twitter, he regularly receives gossip about Dorsey, Bilton wrote, “Once, a source who worked with him told me Dorsey had sent a rapper his beard shavings to make him an amulet that would protect him from evildoers.”

The rapper who allegedly received Dorsey’s facial hair, I’m very excited to share, was Azealia Banks. She tweeted about this exchange in 2016, writing that Dorsey “sent me his hair in an envelope because i was supposed to make him an amulet for protection.”

Let’s remember why Jack Dorsey was fired as CEO of Twitter - 09/15…

Dorsey’s focus on outside hobbies, including sewing and drawing classes, and his frequent party appearances annoyed his co-workers. His lack of communication to investors and apparent six-figure text message bills annoyed the board. He had frequent arguments with Williams, who had provided the initial funding for Twitter. Oh, and while he was in charge, there was no backup of Twitter’s database.

Where is Jack Dorsey’s Charitable Foundation? - 12/18…

As I dug into this mystery, I found a mess of public filings, but no real answers to where the money is. The only thing that’s clear is there is absolutely no way to prove that he’s delivered on his public commitments.

Jack Dorsey’s Eureka Moment - To run Twitter he might have to quit it - 12/18…

Before he entered the Dhamma Mahimã monastery, where he would forgo all forms of communication for a week and a half, Dorsey had posed for a photograph with Twitter’s India team, where he was seen holding a poster that read “Smash Brahminical patriarchy.” The poster, which had been given to him before the photo was taken, set off an uproar in India, playing into the highly charged politics surrounding the country’s caste system, about which Dorsey seemed to be blissfully unaware.

Square CFO Steps down……

Friar isn’t a “normal” CFO, Andrew Jeffrey, an analyst at SunTrust Robinson Humphrey, wrote in a note to investors. “Her leadership in many ways has been more instrumental to Square’s emergence as a true payments disrupter and impressive growth story than CEO, Jack Dorsey’s.”

Bottom line: for elite A-list talent to report directly to this fella and succeed may be a bigger task than we can realize or fairly gauge from outside. I can’t fathom Hastings, Bezos, Buffett, Pandey, Ullal, Gates, Cook doing any of this nonsense. I can imagine Jobs doing it but I don’t think Dorsey is in Jobs’ league. So Friar is gone, Jack’s running this WHILE running the most visible news/social media site in the world? And disappearing for 10 days to meditate. That could be fine. Definitely. But it defies common sense.


Broadway Dan

PS - In my digging I did find that Friar was on the BoD of NEWR and left in May. Said Lew Cirne at the time of her departure, "Sarah has been an invaluable member of our board for many years and I am grateful for her countless contributions to New Relic’s success.” Purely FYI as I hadn’t known that. Apology if already covered here.


Hi Dan

On the other hand we have Tesla, which is within striking range of its all time high in spite of a CEO who I used to admire immensely, but who now seems to be acting like a psychiatric patient who hasn’t been taking his meds. In fact, who makes Dorsey look like a paragon of stability by contrast. :grinning: And he’s running one, two, three companies, I forget how many if you count Solar City. So who knows.



I think the Saulinian method lets the numbers do the talking. And I’ve come to respect that methodology as more logical. Agree 100% on Musk and he was very much on my mind when I posted this. I root for Musk but wouldn’t invest with him and am feeling similar thoughts here. One difference is no one ever questions Musk’s genius as the driving force behind his companies while others allegedly were the brains behind Twitter and Friar may have built Square.

I just have to answer to my BoD (wife/kid). If Square were to tank hard, and they said, “Hold on, you put our money in the hands of a guy who mails his beard to rappers for ritual protection?” I’d be in what C. Everett McGill called, “a tight spot!”

This is the last I’ll speak of this as it’s been noted.


First of all, as intangible as it may be, I think information that helps assess the quality of management is relevant to the decisions about the companies we invest in. At least it is to me, and I think the sentiment is shared by others.

Quite some time ago I made it clear that I bailed out of BOFI primarily due to what I had learned about CEO Garrabrants. More recently I bailed from PVTL after reading the wandering comments from CEO Mee during the quarterly review. Just because we can’t put a number on it doesn’t mean that the quality of management is unimportant. Some time ago Saul sold his position in UBNT as CEO Pera was spending the majority of his time focused on the NBA team he owns.

At the same time, we need to consider how much weight to give to an anecdote about beard clippings sent to a female rapper in order to make an amulet. Was this anything more than a passing fancy with the woman? Well, if you read a little deeper, there was a business motive behind this somewhat bizarre event. Dorsey had promised to promote one of her mixes if she in turn promised to promote Square’s cash app. So maybe it wasn’t altogether so bizarre at all. Cash app is custom made for people who are without banking, who better to get to promote it than a rapper with a high percentage of un-banked fans. The idea of a protection amulet may have been less credible to Dorsey than it is to Azaelia Banks.

While that doesn’t explain all the anecdotes you assembled, it does suggest that Dorsey may not be quite so erratic as it may appear on first blush.

FWIW I’m long SQ (I wouldn’t touch TWTR). I’m willing to give Dorsey a pass on this stuff at least for the time being. But thanks for the information. I’ll be paying more attention to Dorsey’s outside activities.


There are a lot of good things one can say about Jack Dorsey. In fact, he probably doesn’t get a lot of the credit he deserves. First and foremost, he deserves the lion’s share of credit for founding Square, with obviously a huge assist to co-founder Jim McKelvey. That had nothing to do with Sarah.

Dorsey’s rating on Glassdoor are also more than solid. On Glassdoor, SQ scores 4.0 out of 5.0, and Dorsey receives a 84% approval rating. In 2017, Glassdoor ranked him #38 on their Top CEO list.


Roelof Botha, a venture capitalist with Sequoia Capital and a Square board member, wrote a beaming piece about Dorsey and Square when the company went public. Sequoia Capital was one of the first venture capital firms to invest in Square and still owns more than 9% of the company’s voting rights through Class B shares (as of last summer). Botha said:

Jack, and co-founder Jim McKelvey, created a way to bring payments to anyone with a smart phone, and then fought for a year to get it approved by the financial industry. Less resolute builders would have quit when up against such an entrenched and slow-moving system. But the team at Square persevered. Starting with payments as a way to open the door, they have built an entire suite of tools to help small businesses succeed…

…I vividly remember my first glimpse of the product—I started running around the office charging each of my colleagues a dollar for the chance to see the iPhone card reader in action. The device was thrillingly ingenious, but what caught the attention of Sequoia was the founders’ transformative impulse to democratize access to economic empowerment. The card reader was the way in, but economic transformation for small businesses was the goal.


Nearly all of Silicon Valley exhibits some … uh … odd tendencies. The culture is certainly different and I think we need to be careful not to judge some of our comapnies’ teams too harshly based on that culture.

Okay…all that being said, I harbor some concerns about Dorsey’s leadership and Square’s culture too. In last week’s Motley Fool podcast, Bryan Hinmon, Chief Investment Officer of Motley Fool Asset Management discusses the red flags of a corporate culture on the decline. What company does Hinmon believe might be showing signs of a declining culture right now? Yep, you guessed it, Square.

Definitely worth a listen to here…

While Friar was not important to the company’s founding or early days, she was fantastic. And it hurts to lose her.

Anyway, just thought I would share as I also wonder about Dorsey’s leadership capabilities too.

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Dorsey is on the latest Joe Rogan Experience podcast :

“In a wide-ranging two hour interview published Saturday, Jack addressed a number of topics, including questions about Twitter censorship, doxxing, “SmirkGate,” Donald Trump, Alex Jones, the nature of tech giants, the future of the Internet, and Bitcoin.” :…