Back in September 2019, way before COVID was a word understood in every language around the world, I decided that I was going to create a digital accelerator that would help more people build thriving consultancies.
Little did I know that six months later, the country would be thrown into an almost fully-remote workforce where parents were fumbling through their kids’ virtual school during the day while meeting work deadlines at midnight.
This unsustainable lack of balance, subsequent layoffs and the realization that most people really can work outside of the office—and (gasp!) the company will survive—led to an unforeseen acceleration of the flexible work movement.
As the CEO of a company that has been at the forefront of this revolution, I knew that 2020 would be a pivotal year for The Upside.
But the launch of our new accelerator program didn’t happen without a hitch. Here are the three fiascos that almost took down the whole darn thing.
The Tech Gifts That Kept On Giving
As a business owner, I know that the simpler a company looks on the user-end, the more complicated the tech is on the back-end.
The Upside is no different. We use more than a dozen SaaS-based products to create a seamless user experience for our customers.
Designing a new business line meant adding even more tech to bring it to market. More tech meant more potential snafus. And boy did those snafus hit us where it hurt.
We had emails going out at the wrong times to the wrong people and some with the wrong names. Then we had an irreversible 3-hour delay in our customers’ ability to access their new program. We also migrated our entire website over to a new platform and host, resulting in several dead links and 404 errors.
Every day seemed like tech whack-a-mole, never knowing what ugly surprise we’d find. Although the company survived the avalanche of tech issues, it wasn’t without a tremendous amount of stress and an avalanche of frantic late night Whatsapp messages among our team members.
The Election That Ruled All
One of our main strategies for building interest in the new program was through social media ads. It’s a strategy that’s worked really well for my peers, and I was looking forward to reaching more people who didn’t already have The Upside on their radar.
But note to everyone: don’t run an ads campaign a month leading up to elections. The ads barely got any traction no matter what we did. We tweaked copy, creative and targeting. Still crickets.
So we went into the launch with 10% of the audience we had originally projected. In the end, we were faced with the daunting task of squeezing juice out of a rock.
And squeeze we did. But not without working long weekends and late nights to make up for the huge gap in our audience numbers.
The Juggle That Got Real, Real Fast
In the height of the launch, when I needed to put in more hours than I ever had before, my kids were in school for only a few hours a day and I had no full-time childcare.
Miraculously, we were able to get our new au pair here with a lot of phone calls, piles of paperwork and an exemption visa. Then, a week later, he went back home to Germany with the teenage epiphany that it could be a full year of masks, lockdowns and travel bans and not the year of adventure and weekends in NYC he had hoped for.
With two young kids at home and no consistent childcare, I was bouncing between work calls and virtual school on an hourly basis. And I wasn’t doing a great job at either one.
The launch happened on time and as planned. But not without months of late nights (did I mention late nights?) and the constant support of my team plus the encouragement and 50/50 partnership of Mr. Upside who was also trying to run a business during the pandemic.
In The End...
Ultimately, this is a perfect example of what I’ve always said about entrepreneurship: persistence and resilience in business is often what separates the companies that survive and those that don’t.
Running a business can look glamorous and easy from the outside. But any successful business owner will tell you that what goes on behind the scenes is far from the pretty final product you see as the customer.
When quitting isn’t an option, you might encounter times when you have to scrape yourself off the pavement and keep moving forward. But always remember: forward in any direction is still forward!
