Your Many Many Gaps - And How You Fill Them

Nearly a decade ago, a member of my Executive Team walked into my office with a no-win situation. Here’s what it looked like:

I either restructured his ownership in the company, essentially doubling what he had been granted already  --  or he packed up his bag of tricks, shook some hands, wished everyone well…and quit -- exit stage left.

Providing him the equity he was asking for was impossible; he would end up with more ownership than any other executive. Not to mention it would require a Board Vote, an increase to the option pool, and dilution for every single person in the company.

He was valuable but, well, not to everyone else’s detriment.

That said, him leaving the company was nothing short of a nightmare. This was one incredibly talented individual who was literally the central nervous system of the business. He oversaw all of our finances, our employee operations, and our internal client processes; he chaired our team meetings; he managed every vendor relationship.

Losing him would be most certainly a step backward. And (get this) we were right in the middle of selling the company  --  and he was the one responsible for the transaction.

This distinguished gentleman was also a particularly stiff and fearless negotiator. I guess the timing of this “offer” would probably indicate that.

I called our Chairman in a panic. With vitriol and emotion, I explained the situation: Without this exec, we would end up in a tailspin, and our mergers and acquisitions (M&A) transaction would fall apart. We could very well go out of business.

Some of the best advice I've ever -- taken.

Our Chairman listened. He asked a few clarifying questions. He noted that this particular executive, no matter how we looked at it, on pretty much every dimension, would be a major loss and possible crushing blow to the company. After that, he offered the following:

“Let him walk,” he said. “No matter how irreplaceable you believe anyone is, somehow, the gaps always fill in.”

If you haven’t had a chance, ya gotta find some time to watch Under Great White Northern Lights, the 92-minute documentary about the White Stripes’ 2007 Summer Tour of Canada. It’s particularly special because the band intersperses major venue stops with random, obscure tiny gigs — on buses, in cafe’s, and for Indian Tribal Elders who are both bewildered and appreciative of the band’s garage-rock sound.

In the middle of the movie, Jack White shares an insider’s secret to bringing a massive amount of energy to their show each night. With just two musicians (Jack mainly plays guitar and and Meg mainly drums), there’s an incredible amount of space to fill. The trick: every night, Jack positions the piano an inch or two further away than the previous night.

That’s right, he moves it away from him.

Then, in the frenzy of one of their songs, while Jack is playing guitar (completely destroying it really) and singing lyrics through the front-of-stage microphone, he realizes he needs to get to the piano to nail a chord for the melody. So he has to leap — literally jump — over to the piano, which is now more distant from him than ever before.

Every night one inch. Then another inch. And another.

And it’s that tension -- that need to stretch -- to dig deep  --  to challenge his own ability  --  that drives the music. Just where he thinks he has no more room and has exceeded every element of his capability.

Jack White. Stretching. Pushing. Exceeding.

He Filled in Gaps he didn’t even know he had.

In 2013, I had the fortune of of sitting on the executive team of dunnhumby, a $1B revenue data analytics organization. My direct responsibilities included running a venture fund and M&A activities, but more broadly it was to work closely with this global team to run the business. I joined this team after selling BzzAgent to them — and had a few years of required employment to receive the earnout from that sale.

To say the role was overwhelming would be an understatement. Every 8 weeks the executive team traveled to one of our global locations — Thailand, India, Poland, Paris, Oslo, London, Cincinnati (ha, oh yeah, Cincinnati!) — and reviewed, debated and strategized for a week.

Besides a travel regiment that put all of us in a constant fog of jet lag, preparation for this one meeting alone often included a pre-read that could extend to north of 400 pages.

And as if I needed more to do, at the time I was also serving as Chairman of Smarterer, a machine-learning skill assessment business I’d founded back in late 2010. While that required less time, it absolutely filled in any gaps in my schedule and mindspace. Or, any gaps I thought I had.

Then the unimaginable happened.

The CEO of Smarterer resigned; it wasn’t sudden, but it did require immediate action to ensure the business didn’t falter. We had less than a year of cash and no clear scalable revenue model, so Smarterer was unable to stand on its own. We immediately tried to recruit a new CEO and talked to everyone we thought capable — but we were failing miserably. Every solid candidate seemed hesitant to join, for a myriad of reasons.

It was tense.

I flew out to meet with the partner of our lead venture capital investor to discuss the situation. After a bit of light chatter he turned to me, and laid it right down:

You sold us the vision, raised the money and brought in the CEO. You got us into this mess. There are no more bullets left.  Time to step up. You’re the f*cking CEO now.

Three days later I approached the CEO of dunnhumby, and let him know about the corner I’d backed myself into. His suggestion hadn’t even crossed my mind: “why don’t you continue your duties here -- and take that on, too?”

It seemed ridiculous. Untenable on any level. A mental punishment.

But, it was the only way to protect the investors in BzzAgent (for the earnout) and the investors in Smarterer. I really had no choice.

I promised myself I’d do it for only a year.

Somehow, someway I made that year work. I restructured my schedule to remove any wasted time; I shortened meetings by 15 minutes each; I used long flights to execute on project plans; I delegated tasks well beyond my typical micro-manager scope.

Know what? Somehow it all worked. dunnhumby Ventures thrived and I was even given another project or three to manage. And, as if a perfectly delivered punchline, by the end of that predetermined single year, Smarterer had been acquired for a massive returns for investors.

Know how I made it all work? >>The Gaps. I filled them in.

So you run Mylestone as CEO, and recently launched Flipside Crypto, a cryptocurrency investment club? These seem like two full-time jobs.

How exactly do you do both?

I’m not sure that’s the right question.

If you’re inspired, curious, and are driven to deliver on any project — regardless of what is already on your plate — then there is always room.

  • You might feel overwhelmed, but there are thousands of little gaps — little spaces that can be filled with some other effort — within your day that can be filled in.
  • And, on top of that, there are probably dozens of items that you realize could be removed to create even more sizeable gaps.
  • And then there’s the willingness — nay, the requirement — to always stretch to find the gaps you didn’t even know you had.

The Gaps, they always fill in. The Gaps you didn’t even know you had.

So really, the right question might be:

So what will you do to adapt, to adjust, to refine in order to make room?

What Gaps will YOU fill in?