“Managing your own psychology is the number one challenge founders face” – Wonderbly CEO Asi Sharabi

Tech Nation, October 10, 2019 7 min read

James Silver interviewed Asi Sharabi, former scale coach on Tech Nation’s Upscale programme, and co-founder and CEO of Wonderbly, a Future Fifty alumni company. This is an edited extract from Upscale, the book on what it takes to scale a startup, from the people who’ve done it. Applications for Upscale 5.0 and Future Fifty 8.0 are open now.

As an eleventh hour substitute as coach for Upscale 3.0’s first mentoring session, Asi Sharabi, co-founder of Wonderbly, explored a topic rarely discussed by the tech community: the daunting personal and psychological challenges faced by founders when launching and growing their startup.

“Beyond the strategic and operational challenges of founders and CEOs, what I personally find the biggest challenge on a day-to-day basis is what I call managing your own psychology: managing the pressure, the anxiety and all the faces you have to put on in internal and external meetings,” he said. “I realised there are a lot of balancing acts to being a founder, especially when we decided to play the venture-backed game.”

Sharabi — whose startup is a full-stack publisher of personalised books for kids – described the key balancing act as “Killing it versus Shitting it”.

The startup world is awash with testosterone and bravado, and everyone’s expected to ‘kill it’ all the time, he said. “There is this sense of the founder and CEO as some kind of superhuman. Very rarely do you read about how flawed founders can be – just like any other human being. As a first-time founder, so many times I feel like I woke up one morning to find I have a board, investors and 80 people to manage – and I don’t have a f***ing clue about how to do it,” he joked.

At that point, he continues, founders are forced to put on an act at meetings or simply just to get through the day. “Sometimes you are very synched with that act and you feel very confident – and other times you don’t. And this isn’t just in a pitching situation, it’s standing in front of your own company, or doing a management meeting with your execs. On so many occasions and in so many contexts, you either need [to pretend] to be someone you are not, or you have to hack your way through it when you’re not ready.

“Whereas the expectation is that you’re supposed to be killing it all the time, the reality is most of the time you’re shitting it, because you know you’re winging it. You’re doing it for the first time and you’re hoping for the best. Managing your own psychology at those times is probably the number one challenge founders face.”

“A testosterone-led industry”

A week later, at Wonderbly’s Hackney warehouse base, 42-year-old Sharabi, who is almost too tall for the cramped meeting-room we’re in, says there’s something about startups, and VC-backed companies in particular that places intense pressure on a founder.

“When there’s investment involved and you’re making some big promises, there’s a lot more at stake. [Running and scaling a startup] becomes such a completely all-encompassing experience that you can’t afford not to be all in; and in many cases of winning, it’s 150 or even 200 per cent in. In fact, I can’t even imagine someone who managed to found and scale a startup to a desirable outcome, whether in three or ten years, without being 200 per cent all in.”

The result, he says, is that “it’s absolutely impossible” to switch off mentally. “[Your startup] never leaves your head – there’s not a single waking hour when this thing is not part of your being. This goes way beyond busy. You can optimise for busy. You can clear time for busy. I’m talking about the added level of mental commitment where it’s absolutely impossible to park it mentally.”

“Yes, you can say I’m taking a week off to go to Vietnam, but the ability to switch off when you get there is a luxury you just don’t have. You can optimise the conditions for switching off if you have a very supportive co-founder, that you absolutely trust, but that really isn’t what happens in practice.

“Generally speaking, when you’re scaling fast, and when things are going in the right direction for a significant amount of time, the company and the commitment grow at the same time – and, [contrary to what you may expect], it doesn’t get easier in any shape or form.

“You may convince yourself that you’re getting used to it all, you can still get better at managing your time and become more efficient, but that’s all tactical stuff. It’s such an all-encompassing experience…” He trails off. “I’ve been in various roles, in various situations,  and nothing compares with how all-consuming [founding a startup] is.”

Switching off

Sharabi stresses the difficulty in mentally switching off, citing the example of a recent family holiday where his psychological absence sorely tested his family’s patience.

“Some weeks ago, I was with my wife’s extended family for an annual gathering in the Alps. I was there physically, but not mentally. It doesn’t matter how much you try, you can’t just put on a face and pretend that you’re fully engaged when you’re not. I was working all the time, but when you’re working, at least the others know what you’re doing. It’s in those couple of hours at least where you’re supposedly not working, that you’re spending with your family, that they notice you’re not really present.

“It’s a similar thing with weekends, where you kind of can’t wait for the weekend, because who doesn’t? But at the same time the weekend can be such a drag. It’s almost as if you get to Saturday morning and you’re 150mph one minute and hitting the wall the next. And there’s no one you can talk to about it.”

Asked whether he thinks many founders are almost complicit in not discussing this aspect of entrepreneurship, for fear of perhaps appearing ‘weak’, Sharabi is unequivocal. “I have no doubt. Anecdotally, occasionally, someone will voice something different but at the end of the day, you’re living in a testosterone-led industry where it’s all about “the gospel of growth”. And, mostly, you only hear the good stories.”

Balancing acts

“If you live in this world and you see the success stories, you develop this notion of the “Superman/Wonderwoman” founder who went through everything, the ups and downs, but came out winning. The expectation from a leader in any context – political, commercial – is to appear strong, optimistic, hopeful, resourceful and to know pretty much everything, at any given time. In this regard it’s not necessarily only a startup thing, but in the startup world in particular, that’s what’s expected of you, and especially in this context, where things can change so fast, and in many cases you almost accidentally got to this point – if it’s going well, and things are scaling,” he says.

But if founders are expecting simple solutions to managing the stresses and strains, he argues that they don’t exist. “The reason why I’ve started to think about balancing acts and the idea of managing your own psychology is there is no right and wrong way [of going about it]. You can apply one thing that makes a lot of sense in a particular context, but not in others. Sometimes, putting on this Superman mask and going for ‘the kill’ is exactly the right thing to do, because it comes more naturally to you. But at other times it doesn’t and it’s almost as if you don’t have the luxury to say: ‘Today I don’t feel like Superman’.”

Despite this, he is also at pains to stress that founding and running a startup is the best job he’s ever had. “The thrill of the journey, the satisfaction of figuring how to make it work, the small and big wins – it’s still absolutely worth it”, he insists.

Pulling yourself back to the present

Back at the Upscale mentoring session, Sharabi drew the session to a close by asking how many founders present had a partner and or kids? A smattering of hands slowly went up.

As a father of three daughters, he knows only too well how preserving a personal life while scaling a startup entails yet another balancing act – one he terms “Giving it everything versus Remembering your wife and kids”. He told those present: “I can find myself at home over the whole weekend, but I’m not there. The voices of my kids are just somewhere around me because I’m so completely preoccupied with my meeting on Friday or the one coming on Monday. And it can be incredibly difficult to pull yourself back to the present and be there with your partner and kids. Sometimes you can do it, other times you can’t.

“A very supportive partner like my wife is always a great thing to have, but be aware of that. Be aware that the [startup] is not the only thing that matters and there are others who need some of your attention too. So giving your startup absolutely everything you can, while at the same time not forgetting the other people who want you and need you, is a struggle –and it’s a balancing act that I’ve yet to personally master.” Then he adds: “But I’m doing better than I was six or seven months ago.”

Applications for Upscale 5.0 close on 24th October, with applications for Future Fifty 8.0 open until 5th November. To stay up to date with all Upscale & Future Fifty news follow us on twitter and sign up to the Tech Nation newsletter.

Explore more scaling insights from Asi Sharabi and 24 other UK founders, investors and tech veterens in Upscale, the book, what it takes to scale a startup, from those who’ve done it.

Mental Health, Upscale 4.0, Mid Stage