Lessons from Jack Dorsey, CEO of Square + Twitter

Shahirah Gardener, Finch + Jack Dorsey, Square/Twitter @ Victorian Innovation Hub. Photo credit @HughEvans

Shahirah Gardener, Finch + Jack Dorsey, Square/Twitter @ Victorian Innovation Hub. Photo credit @HughEvans

It’s a cool, sunny Melbourne morning in the first week of Spring and the Victorian Innovation Hub is all a-twitter. (Ha, see what I did there?)

And for good reason. Mr Jack Dorsey himself is in the building! The co-founder, CEO of Twitter and founder, CEO of payments FinTech, Square, Jack definitely has rock-star status in the founder and innovation community.

This morning, he shared the stage with Shahirah Gardener, co-founder and CMO of Aussie FinTech, Finch, and talked about his experience being a founder and leader of global companies.

We’ve gathered some of our favourite gems for you here…

On knowing everything…

“Be brave enough to ask ‘why?’
Be strong enough to say, “I don’t know.”
Be diligent enough to do the work to figure it out.”

On having domain expertise…

“Being naive [about finance] helped us question the fundamentals of the industry. We didn’t hire our first finance expert until about employee number 60.”

On simple business models…

“We ask ourselves [at Square] — How do we help the seller make their sales?
How do we help them make more sales?
If they grow, we grow.”

On founder wellbeing…

“I don’t expect that I can give 100% every day. But I set myself up to experiment, go to the edges of things and test them and learn something. This includes experimenting with new practices which might help my physical and mental health.”

On building something that lasts…

“The CEO’s role is to create a company that lasts beyond me, or any one employee. If you are a CEO making every single decision, you’ve built a failure of a company and your people are not empowered.”

On his top three responsibilities as a CEO…

“#1 job is to create an excellent team dynamic. This means hiring, firing and editing the team, and building a healthy, inspiring, challenging dynamic.

#2 job is to make sure decisions are being made in the contest of the people that we serve. Decisions should be made as close as possible to the customer.

#3 job is to constantly raise the bar. We’ve made the impossible possible, and we can still do so much more and push ourselves to be 1% better every day”

On personal and professional development…

Jack shared that he never set out to become an engineer or a CEO. Instead, he realised that in order to build things he wanted to build and solve problems for millions of people, he had to develop certain skills. Coding, understanding internet behaviour and culture, and running a business all ‘unfolded’ from the desire to build solutions.

On practicing your pitch…

Jack teed up two weeks worth of investor meetings, scheduling investors they didn’t want to work with at the start. By doing this, they could practice their pitch on ‘less important’ investors, so by the time they got to the ones they wanted, the pitch was polished and they had practiced answering investor questions.

On knowing your weaknesses…

Jack created a list of 140 reasons why the company could fail before they started pitching to investors. This allowed them to show vulnerability and start addressing all the gaps in their knowledge and business in a systematic fashion.

On working with corporates…

Despite a direct introduction to the CEO of Visa, Jack and his Square co-founder struggled to get traction with the finance giant in the early days. They pivoted and began working with Chase bank, where they discovered more innovative thinking. With Chase’s support, they were able to get Visa on board down the track!

On entrepreneurship…

Jack believes that the spirit of entrepreneurship is: “We will make it work,” and he believes that problem solving and critical thinking skills are essential for emerging entrepreneurs and innovators.


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For more amazing founder insights, real-life stories, skills and network building, check out The Hacker Exchange innovation programs in Melbourne, San Francisco, Singapore and Tel Aviv.


Thanks to Fintech Australia for hosting this event, to Bryce Chee from Stone & Chalk for the invitation, and to Hexie Sophia Ireland for contributing to this blog. Photo credit to @HeathEvans. Please note, some of the quotes may be paraphrased, and we’re happy to take edits from anyone who had a recording device at the event! :)