What Keeps Business Owners Up at Night

The best, truest, and most bleak line I’ve heard from a mega-successful company founder was Dave Becker telling me: “we have all had the sleepless nights, when it’s 2am and you’re staring at the ceiling.” Dave is the founder of a number of companies including First Internet Bancorp (Nasdaq: INBK), the granddaddy of online banking.

From the outside, we see a successful entrepreneur with multiple home runs and think they must be sitting on easy street. What could possibly go wrong?

The answer is: everything. It always appears easy or obvious once a company has made it, but what we often don’t hear about are the trials and tribulations that happen at every stage of a company’s growth from young and unknown, to in between, and then big and ambitious. The sleepless nights. The questions of can you make payroll. The we-almost-went-bankrupt moments. This is real and it’s no surprise that many of our inquiries for help from owners show up in our inbox after the 9-5 employees have gone home.

The Early Jitters

The early jitters that keep owners up at night are plentiful from cash crunches, to lack of talent, to not enough customers. When I interviewed 45 entrepreneurs for the book How They Did It, asking them to share advice and insights from their journey, Eric Lefkofsky whose latest company Tempus is a technology to battle cancer, told us his only real challenge was revenue – a great perspective to keep every other issue in check. Jeff Aronin, a biotech and healthcare entrepreneur, put it another way, saying that when a company is young, there’s nowhere to hide.

The Long Middle

At the beginning of a new idea, everyone is fired up and excited. The end of the process is also easy once there is massive success, market share and profits. But the hard thing is the number of years where no one could have anticipated how long it would take for the market to adopt, for the team to fully execute, and for the world to catch up on our grand plans. Steve Ballmer described this as the long middle, pointing Microsoft’s execution of the graphic user interface, which all in only took about 20 years to full realize.

The Perils of True Success

So it all gets easier with scale and market adulation right? Owners still report sleepless nights. We’ll bet Netflix founder, Reed Hastings, didn’t get much shuteye while dealing with the pricing debacle and launch of the ill-fated Quikster service, which at the time cut Netflix’s valuation in half overnight. The challenge is seeing where competition, the markets, and global demand will go. The established companies should never discount the entrepreneurs working out of their garage…. that’s where most of them started after all. A few will make it. Most will not. But owners need to surround themselves with those who will challenge the status quo, not be afraid to reinvent, and never stop innovating.