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This interview with Asi Sharabi, cofounder and CEO of Wonderbly is the first in a new series called Upscale Knowledge; a run of interviews with mentors from the programme on a range of topics facing entrepreneurs today.

As an eleventh hour substitute as coach for 2017’s first Upscale mentoring session, Asi Sharabi 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. “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 luxury you just don’t have. 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. I’ve been in various roles, in various situations,  and nothing compares with how all-consuming it is.”

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.”

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.

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.”

Two more of Asi Sarabi’s ‘balancing acts’ for founders.

‘Focus versus opportunism’

“This is more of a juggling act. I can’t think of a single board meeting I’ve been to where the board didn’t emphasize focus, as in: ‘You guys need to focus more – and you’ll be fine’’. What they mean by that is that if you spread yourself too thin, you’ll end up not achieving anything. If there is an opportunity for 2x growth here and 2x growth there, you cannot juggle between the two, you have to decide which one you’re going after and apply yourself 100% to that.

While it makes a lot of sense, it’s also very [theoretical]. In many cases, you need to find the right balance, between forcing yourself to focus, because it’s a good discipline in itself, but at the same time, there is something inherently positive in the mild ADD [Attention Deficit Disorder] that good founders have, where they’re thinking ‘What’s next?’ all the time.

You can really screw yourself over by not being focused by spreading yourself so thin that you end up achieving nothing, but at the same time you can focus so hard that you miss some big things — and see your competition come in and pass you by as a result.”

‘Stepping up versus track record?’

“This one is a little more practical than psychological: promoting talent internally versus hiring a heavyweight outsider with a proven track record. As a founder, you’ll hear successful entrepreneurs and VCs say: ‘Look, your job is to manage your risks, and hiring [external] senior execs who have ‘been there, done that’, is one way to de-risk. And because your job is inherently about taking risks, then if there’s any way to de-risk than you should take the opportunity [to do so]’.

“But at the same time you’re saying to yourself, if — in my own case — there was an opening for a CEO role at a tech-led publishing company in London, I probably wouldn’t get approached, [despite the fact that] I’m doing this role right now, and doing it relatively OK. Besides, I have lots of examples of Venture-backed companies who, as soon as they raised Series A, hired two or three senior execs, and the business couldn’t absorb them. And [in those cases], it was a failure because that person was wrong for the business, or they might have performed in one context but couldn’t replicate it another. So, as a founder, you have to balance these competing [outlooks].”

Applications for Upscale 3.0 open October 2017. To stay up to date with all Upscale news follow us on twitter and sign up to the Tech City UK newsletter.

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