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Humans are analysts by nature. We like to sift through the past in search of clues for a successful future — and in the startup world, that’s no different: who among us has never hypothesized about the one key ingredient that determines whether or not a company will make it?

Some think it’s the team, others funding, and a few are convinced that product is the determining factor. Of course, all of these play a significant role, but none can hold a candle to an all-too-often overlooked criterion: timing.

How COVID Derailed Bookasleeper

In 2019, I co-founded the night train booking platform Bookasleeper with João Sobral and Christian Hirsig.

We launched this project in cooperation with SBB and ÖBB (the Swiss and Austrian national railway companies, respectively) at a time when booking night trains was a slow, frustrating process: you never got all the needed info, you had to switch platforms multiple times, and sometimes it simply wasn’t possible to purchase your ticket online.

We saw a consumer need and combined with it a worthy goal: motivate people to take the train instead of the plane. 

Bookasleeper


Early Success

At first, things went even better than expected! We launched in February 2020, and our social media campaigns and organic search quickly generated bookings faster and cheaper than originally assumed.

We had almost 100’000 website sessions in a short time and generated tens of thousands of euros in revenue. Our partners were happy with us and were on cloud nine. It all felt like the start of something great. 

And something ‘great’ was coming, in the original sense of the word… but not Bookasleeper’s success.

Fast forward one month to March 2020, and COVID hit Europe in full force — train services stopped: no night trains, no day trains, no nothing. The railways were at a standstill, and so was our chance at success.

Through no fault of our own (we haven’t gotten around to purchasing that crystal ball yet), we had launched Bookasleeper at precisely the wrong time.

Mitigation Strategies for an Ailing Startup

We weren’t going to go down without a fight, though. We slimmed down our (already remote) operations as much as humanly possible by shutting down ads, and we renegotiated with our partners and suppliers, letting them know we’d be entering hibernation mode until the COVID restrictions were lifted. 

But the pandemic, as we now know, lasted much longer than initially expected, and another unhappy development came along to put us out of our misery definitively: ÖBB started to consider us competitors. We sold more tickets than their biggest partners! You would think great sales numbers would be a plus, but the startup world has sneaky ways of surprising you. 

We made SBB and OBB all sorts of proposals: we told them we needed more funding, we suggested they integrate Bookasleeper into their existing systems (which would have been easier if these systems weren’t quite so geriatric), and we even proposed that they take over Bookasleeper and lead it themselves. None of these seemed like good options to them, and Bookasleeper shut down for good in September 2020.

How COVID Revitalized Rentouch and Led To Its Successful Exit

No pain, no gain, as they say. So, I picked myself up and joined a new venture: Rentouch, a remote visual collaboration software founded in 2012 by Raphael Vincent Sigg and Dominique Burnand.

Rentouch’s story drew a curious (some would say ironic) parallel with Bookasleeper’s: it started as a physical touch screen manufacturer before pivoting to software, and its mediocre traction almost led the founders to call it quits around 2018. But they pushed on instead — and two years after, when COVID came around, meeting/team collaboration software like Rentouch’s became God’s gift to corporate-kind. Sales went through the roof, and Raphael and Dominique found themselves needing additional support: that’s where I came in in April 2020.

In Rentouch’s case, the duration of the pandemic and its restrictions was a definite upside: inbound sales kept coming in like crazy from customers big and small, and we were able to scale the company up more than the founders could have predicted.

In 2022, I was offered the CEO role with a specific goal in mind: to lead Rentouch on its way to a big exit. A year later, we were in talks with a potential buyer; 4 months later, we signed the deal with Scaled Agile!

So what’s the lesson here? Rentouch was a moderately successful venture with few prospects of improvement until a worldwide, radically life-changing event came and tipped the business scales in their favor. Bookasleeper failed because we couldn’t possibly have predicted COVID, and Rentouch was reborn through no particular merit of its hard-working team but due to absolute chance.

What’s another word for chance, in this case? Oh, that’s right: TIMING!  

How This Applies To You

You’re not the master of the future (or present, for that matter). You can’t predict timing; you can’t change it. All you can do is pay attention and understand where you and your company stand.

If a catastrophe is on its way, then that’s that, but pondering that possibility can’t take up too much of your brain space, or you’ll be paralyzed and never start ventures at all. Similarly, you don’t know if or when the startup gods will decide things in your favor. You can, however, stay lean, with the lowest possible burn rate, and stay put, ready to pounce and scale up if the opportunity presents itself — if the timing is right.

How do you know if the timing seems to be going well for your company? There are no sure answers, but a good rule of thumb is inbound requests: are you finding yourself having to shove the product/service down the customer’s throat? Or do you, on the other hand, receive plenty of inbound requests, perhaps so many of them that you can hardly keep up?

Besides being a startup founder, I’m also a podcast host at Swisspreneur, Switzerland’s #1 business podcast. There was one thing that our founder and chairman, Alain Chuard, said on the show’s first-ever episode, which has stuck with me since: Timing is like surfing.

You can see the wave coming, and it comes regardless of how prepared you are — so what you can do as a founder and what you should do is ensure you’re ready.

I would add that we should also mind the importance of choosing the right wave: your risk-tolerant nature makes you see opportunities left and right, but not all possibilities are worth exploring, and focus is a startup founder’s most prized possession. Happy surfing!

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