Intercom’s Des Traynor reveals the realities of a founder’s journey

31 May 2019

Des Traynor, co-founder of Intercom. Image: Conor McCabe Photography

Intercom co-founder Des Traynor told Inspirefest how relying on the contingency of progress has served him well during the highs and lows of building a company.

Once viewed by the establishment as suspect, entrepreneurs are now fashionable, desirable and all in vogue. Especially tech entrepreneurs whose companies enter the elusive and exclusive $1bn ‘unicorn’ club. In many ways that’s the case of Intercom, a company started in San Francisco in 2011 by four Irishmen – Des Traynor, Ciaran Lee, Eoghan McCabe and David Barrett – and which last year sailed past the $1bn valuation milestone after raising $125m in a series D round.

The company employs about 600 people in five offices worldwide and has more than 30,000 customers. Most of the company’s engineering happens at its Dublin office on St Stephen’s Green.

‘Ignore the top tips and hustle bullshit, you do you and whatever happens is whatever should happen. And if you try to be somebody else, it ain’t gonna work’

But at Inspirefest 2019, Traynor appeared to feel duty-bound to inform people considering the start-up route that it is not all as glamorous as portrayed and that a founder’s journey is often one of tribulation and personal discovery.

In many ways, Traynor did the full apprenticeship. He studied computer science, got bored, became addicted to Counter-Strike, discovered new programming languages and came up with novel apps that had the unintended consequence of becoming the heart of Intercom.

Zoom forward to today where Intercom now has 30,000 customers, Traynor said he gets asked all the time about his “top tips” for start-up success – “when did you know?” or “what was your biggest mistake?”

He said: “The thing that frustrates me most is the popular answers like working 996 (9am to 9pm, six days a week). It’s horseshit. People say hustle, crush it, fail fast, fake it ’til you make it.

“Those are the wrong questions and answers, the cultural cycle of start-up gloss.”

There is no A to Z narrative on the founder’s journey

“What you don’t see is all the different decisions that we made along the way. All of these different paths. A start-up or life in general is like a set of multi-various decisions where you can start a company or not, or build this feature and not hire that person or not. And you know that does not make for a good movie, ‘but this ain’t a movie, dawg’, as Jay-Z once said.”

Traynor said that the founder’s journey is like anyone’s life; it’s about the decisions you make and how well you execute on those decisions.

“It’s things you choose to do and then how well you do them. How well you execute is probably the biggest control variable on your success in life, in start-ups, in relationships, whatever.

Crucially, Traynor revealed, it all boils down to time, effort, ability and luck. “How much [time] are you truly willing to sacrifice to make the thing you want to make happen?

“Time is the only resource that, no matter how much money you have, no matter how much influence, power, control, you can never manufacture time beyond the seconds you have on this planet. You have as many minutes in your day as Beyoncé, right?”

For knowledge workers, he asked: “Are you investing in making yourself a lot better? Are you reading, are you learning, are you getting inspiration, are you getting motivation, are you really genuinely investing in making yourself better? Because if you don’t, your lack of ability will hold you back. And, lastly, the thing everyone loves to forget is that you have to be fucking lucky, too.”

An example of the kind of lucky break for Intercom’s founders in the early days came when they built an app called Quitter based on Twitter’s API that notified people when someone stopped following them. That led to a meeting with Twitter co-founder Biz Stone who went on to invest the first $100,000 in Intercom.

Traynor said the journey of the founder is one of resilience, and there is a need to break out of negative cycles and emerge from setbacks.

“Negative cycles are one of the most destructive things in the decisions you make; your best chance when you’re in one is to make a decision that breaks you out of it.

“The decisions that I would make consistently that have helped me unlock cycles and actually keep the journey moving, I always try to rely on ‘the contingency of progress’. And what I mean by that phrase is, even if I’m making the wrong decision here, I’m still moving forward.

“Happiness comes from within. It does not come from the extrinsic trinkets of success. The success feeling that you need is actually inside you and it’s not held in your car or your yacht or anything like it.”

He reiterated that there is no A to Z narrative. “It’s a mess, and for me to pretend I knew what I was doing at any stage, I just can’t. Not only is it a mess, it’s just highs and lows 24/7. We closed $23m the day my mom got diagnosed with cancer. And you have to process these things at the same time. We closed our Series C on the day one of my best friends said he was going to leave the company and, like, that’s a professional high and low at the same time. You’re constantly jumping between various psychological states of professional and personal happiness and crises, and it’s literally relentless.

“Ignore the top tips and hustle bullshit, you do you and whatever happens is whatever should happen. And if you try to be somebody else, it ain’t gonna work.

“I really believe in relying on the contingency of progress. Keep moving forward. Break out of any negative cycles you find yourself in, professionally and personally. If you’re in a job where not you’re not moving forward, you are moving backwards.

“Know that your success is a combination of your time, your effort, your ability and luck.”

Inspirefest is Silicon Republic’s international event celebrating the point where science, technology and the arts collide. Ultra Early Bird tickets for Inspirefest 2020 are available now.

John Kennedy is a journalist who served as editor of Silicon Republic for 17 years