Thread by @ankithharathi

On October 5, 2015, Jack Dorsey had a meeting that would go on to become infamous.

Immediately after, many called for his resignation as CEO.

Here’s what went down in that meeting 🧶👇

1/ Jack Dorsey almost never became tech founder. He was entirely obsessed with a different world.

Fashion design.

2/ But after meeting Evan Williams and Biz Stone, the group founded Twitter in 2006 and Jack became CEO

Just one month before their official launch, he told his co-founders

“I’m going to quit tech and become a fashion designer”

3/ Even before officially leaving, Jack faced criticism for his outside interests.

He’d regularly leave the office “around 6 p.m. for drawing classes, hot yoga sessions and a course at a local fashion school”

4/ Evan Williams was straight with him

“You can either be a dressmaker or the CEO of Twitter. But you can’t be both”

On October 16, 2008, Williams took over as CEO.

5/ Jack now had the separation he wanted.

But surprisingly, he found his way back to tech.

In 2009, while helping a friend accept credit cards as payments for his small business, he co-founded Square.

6/ Square grew rapidly. And this time, Jack stayed at the helm.

Just about a month before Square was set to go public, he called a company wide meeting.

7/ Everyone gathered, anxious to hear what Jack had to say on the precipice of their monumental achievement.

After a brief welcome, he wasted no time in making his announcement:

He’d just been named the CEO of Twitter, again.

8/ But what about Square?

He wasn’t leaving. He’d still be CEO.

He was going to lead both companies, at the same time.

9/ Immediately, people expressed their outrage and disappointment.

Even Elon Musk, who’d been doing the same with Tesla and SpaceX, didn’t recommend running two companies simultaneously.

10/ Twitter had been public for 2 years already, and Square was just a month away.

Many feared that because of Jack, the stock prices of of the two companies would be unfairly linked.

11/ Sensing the frustration, he immediately responded.

“Look, we don’t always need to agree. And that’s okay”

This was happening.

12/ People could protest as much as they’d like, but they couldn’t argue with results.

Unfortunately, the short-term results weren’t so great.

13/ After taking over, Jack announced that Twitter had gotten too large and they were going to lay off 8% of the workforce (~340 people).

Coupled with disappointing third-quarter results, Twitter stock price plunged.

But Jack continued to face the fight directly.

14/ As part of the restructuring, he announced he’d give $200M of his own personal stock compensation, back to Twitter employees.

He created a detailed turnaround plan for the company with renewed focus on its mission.

15/ As Square prepped for its IPO, the company lowered its initial offering share price to $9 (from an expected $11-13).

Investors speculated this was to account for public market wariness about Jack being the CEO of two companies.

16/ But on IPO day, the stock popped 45%, and Square was off to the races.

Over the next few years, he wrangled both Square and Twitter, with both co’s hitting record-high all time stock prices.

17/ On reflection, Jack thought back to that moment at the Square all-hands.

“There are many moments in a company’s life where, as a leader, you’ll be an island.

And you expect your team to disagree, but still commit.”

18/ Although the disagreement was palpable, the teams at Square and Twitter committed to Jack’s vision.

And the results speak for themselves.