Success can bring many benefits, but it won’t stop fear in its tracks. From Musk to Branson, even billionaire masterminds say the entrepreneurial journey is one that naturally leads to a lot of hairy moments.
However, it’s worth remembering the thing that scares or stresses you most in your business is unique to you — and everyone has to sit with tough moments and stare down situations where it seems like your business is entering troubled waters.
We asked four founders to share some of the scariest moments in their careers: the times they’ve feared all is lost, the moments that trigger the fear and how they’ve forged ahead.
Janine Allis | Founder, Boost Juice
Has there been a particularly scary moment in your career so far that stands out?
“Not scary… there are things where you go, ‘oh my god’, though. For me, it’s probably when something has hit the media and you get that note to call 45 media stations [to talk about it]. You have no control of it, but you always go, ‘well this will be interesting’.
“Anything where I’m not in control is scary for me – so like legal things, where there’s nothing certain, and there may be grey areas.”
What advice do you have for sitting with that fear?
“Keep perspective on it, because nine times out of ten, nobody died. For you it’s probably the worst thing in the world, but just keep perspective and battle the battles when they come.”
Josh Simons | Co-founder of music networking app Vampr
What has been the scariest moment of your career so far?
“Every time we have come to the end of a cash runway and need to close a capital raising is pretty tense.”
Has there been a moment where it’s gone down to the wire, where it’s felt like you’re in seriously troubled waters with your business?
“Multiple times! We’ve nearly had to lay off our entire staff on two separate occasions — it’s the nature of a pre-revenue startup. You’re simultaneously trying to build a skilled and dedicated team whilst also growing a user base. Longevity and scalability are important concepts on both sides.
“And growing each side costs money — both necessary to win over prospective investors and to build a proper business.”
How did you overcame this and do you have any advice for company founders off the back of it?
“Patience, persistence and attentiveness. All three things probably seem obvious but when your back is up against the wall it’s easy to forgot all three. You need to remain calm. You have to keep hustling, perhaps pivot in your approach, and most importantly, listen.
“If enough people aren’t jumping in there’s possibly a reason (beyond the state of the market). It’s important to look inwards and maybe execute in areas you’ve previously neglected or didn’t feel the need to address. Some of the people who have said no to us in the past have helped us grow to where we are today, and in a backwards way I’m very glad we had to put up with the adversity at the time.”
Matt Schiller | Co-founder of photography startup Snappr
What has been the scariest moment of building your business so far? Why was that the case and how did you face it?
“The scariest time in the life of Snappr was in the lead-up to our launch in the US, just after having started the Y Combinator program. Having run Snappr’s on-demand photography marketplace exclusively in Australia in our early days in 2016, we had great product-market fit in Australia, but we didn’t know how this would extend to the US market.
“A lot hinged on our US launch being a success. Many questions flew around. Would our cheeky style of marketing strike the right chord with Americans? Would the unit economics for on-demand photographers work in a different market? Would Snappr be able to rise above the ‘noise’ of the Silicon Valley?
“We’d done as much paper research as we could to predict the answers, but there was no way of knowing how it would play out in reality … apart from going for it! After pushing the button on our San Francisco launch on February 14, 2017, to our great relief everything went swimmingly and San Francisco became our fastest growing market.”
Any advice for other entrepreneurs based off the experience?
“I think the biggest lesson from this would be, ‘don’t be scared of the US market and American customers’! While it is a more competitive and sophisticated market in many respects, ultimately American consumers have more in common with Aussies than they have differences.”
Richenda Vermeulen | Founder of digital agency ntegrity
What’s been the scariest or most ‘down to the wire’ moment in building your business so far?
“There are so many that come to mind, but isn’t that the whole journey? You’re scared [as an entrepreneur] and then you overcome it and go on.
“There are a couple of things in particular that come to mind. One was around 2014, after the election had happened. We had just seen a change of government [in 2013] and because of that, it killed a couple of government departments we had good contracts with. Thirty percent of our revenue was gone overnight.
“I had just hired people off those contracts, so that was pretty terrifying. It’s really something that happens and you really can’t see it coming.
“It’s that moment when you think you can’t pay these staff that you just hired.”
What did you learn from that experience?
“What that taught me was about diversification. We were specialists working in governments and not-for-profits. But now as the market shifts and things happen, we’re never too exposed — and that [approach] is actually counter to advice we got at the time, which was to specialise.
“In terms of other [scary] things I’ve seen in business, well, I think I speak to a lot of other founders who resonate with this: that the pressure that running your own company puts on you can mean you’re more prone to struggles with mental health.
“And there can be fear in that if there is a morning where you can’t get out of bed, well you just have to — nobody else is going to run the show. When you don’t know what’s going on in your head sometimes but you need to keep going anyway, well I think that’s something a lot of founders don’t talk about publicly.”
Do you have any thoughts on how founders can face those tough moments?
“It’s never easy to share it, because people don’t want to hear it. However, you should really just try to make space for rest. Being in that vulnerable state is often accompanied by working long hours and not getting much sleep. So even if it’s just a day to step away, have a rest.”
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