It’s hard to say goodbye!

Friday was my last day at Datorama (Salesforce). It still doesn’t feel quite real. Datorama has, without question, been the highlight of my professional career. The learning, the growth, the relationships, the economic result, all were more than I could ever ask for. Probably more than I deserve.

And so, at such a transitional moment in my career, or more accurately my life, I’ll take a moment to reflect.

One thing I learned…

If you had asked me to define leadership before 2015, I might have said something about work ethic, the will to win, or putting the team on your back. I might have described the ability to deliver consistently stellar results. But today I have a different perspective. I’m not even sure what words to use, but I’ll offer up a few emblematic moments that capture the idea.

When Datorama was acquired by Salesforce in August of 2018, we had a company-wide all hands to celebrate the milestone. My boss stood up to talk about what the moment meant to him. But before he could muster up any words, he began to cry. I’m not sure I heard anything that he said after the tears began to flow. The tears said everything. For me, those tears represented how deeply he cared. How deeply he cared about our employees, our customers, and our families that often carried the load at home while we were on the grind trying to accomplish the impossible. 20 years from now, I won’t remember any of the deals we closed or how much money we made. But I will forever remember those tears and how much he cares.

I love Halloween! The love partially stems from the fact that my birthday falls on November 1st, so Halloween celebrations always feel like birthday parties. But there’s another reason. Our Monday sales meetings at the office following Halloween are always some of my favorites. My boss has 4 young girls and he always puts up pictures of their family Halloween costumes. I think my favorite over the years would probably be when all of the girls, he, and his wife all dressed up as different sized Russian dolls. Incredible!

The pictures were fun and comedic, but they also said something more important. They said that being a good dad matters. They said that family is important. They said that we are all much more than our sales results or performance reviews. We are whole human beings and or support systems are crucial if we are to do anything of significance. Those pictures taught me more about leadership than any management book ever will.

I recently met Magic Johnson in Las Vegas during our annual sales kickoff.

He told a story about playing for the Dream Team (the 1992 Olympic gold-winning US men’s basketball team, arguably the greatest team ever assembled). According to Magic, the coach asked Michael Jordan if he wanted to be a team captain. Surprisingly, he said that Magic and Bird (Larry) were the obvious choices, and that those guys should share the responsibility. Magic was clear about who lead the team when they hit the floor (MJ), but in that moment, he felt that Jordan’s humility and respect for two greats of the game demonstrated that the team came before his ego. That set the tone.

Coming back to my boss, he’s the best salesperson I’ve ever met. He built the sales machine from scratch and single-handedly closed the first $5 million in revenue. Yet, I never once saw him beat his chest or seek out the spotlight. The only time he sought attention was when someone needed to take responsibility for missing our numbers, or when someone needed to speak to an irate customer. It’s a really special combination when someone celebrates other people’s success over their own, while regularly diving on grenades for other people at the first sign of trouble.

I guess what I’m saying, after rereading what I just wrote, is that there aren’t really any adjectives that describe leadership adequately. Rather, it’s all about the small actions, steps, and behaviors that a leader demonstrates repeatedly over time that define their significance to the organization.

So how would I define leadership? Tyler Sandler.

Why it’s time to leave…

One of my favorite people at Datorama has a great question for anyone leaving a job.

“Are you running away from something or running toward something?”

To be clear, there are times when you need to escape a situation. Mental or physical abuse, discrimination, unethical behavior, a generally toxic environment. All can be reasons to pull the rip cord.

However, broadly speaking, it seems to me that it’s preferable to be running towards something as opposed to away.

At Datorama, there’s not much to run away from. The company is growing faster than it ever has. 75% of the sales organization is hitting their numbers, including everyone that reported to me. We have a stellar management team. We have built-in distribution in a large base of existing Salesforce customers. The stock is up 70% in the last 2 years. What’s not to like?

But remember, I am running towards something. In my annual letter this year, I wrote about the driving force of my life. I wrote about the desire to achieve economic and intellectual escape velocity. Taking a shot at building a company is the next step on that journey.

On the intellectual front, building this company will be an infinitely harder intellectual challenge. It falls on my shoulders to define the sales process, marketing strategy, pricing model… everything to do with our go-to-market. My partner’s area of responsibility is all things product and technology. To be honest, it’s actually a bit anxiety-producing when I think about it. But I think that anxiety is natural. Your heart is supposed to beat faster and your palms are supposed to sweat before you ask the girl to dance.

Further, even if this doesn’t work out, I believe that the learnings that I take from the experience will be invaluable. You can read all of the books and take all of the classes, but some things in life are trial by fire. I don’t want to look back at today when I’m 50 and say that I never took my shot.

On the economic front, starting a technology company is not rational. The overwhelming majority of companies fail. However, the upside potential is far greater than working for other people. And that’s not only with regard to the outlier companies that ring the bell at the stock exchange or sell for hundreds of millions of dollars. When you hold substantial equity ownership in even modestly sized businesses, seemingly small outcomes become meaningful.

And again, to come back to the very real possibility that it doesn’t work, the economic downside is limited. We have sufficient money in the bank to take a chance. My beautiful wife has an incredible job with great health benefits that I can attach to. I’m confident I could get another job down the road if it came to that.

In short, it’s worth taking a shot when you have limited downside with unlimited upside.

So what comes next? What are we building?

I spent many of my childhood years in a town called Elkins Park on the border of northern Philadelphia. It was a quiet and safe neighborhood. We often left the door unlocked when we left the house for a few hours. When at home, it was often wide open. I don’t remember having a curfew and no homeless people were wandering the streets. Most of my time was spent at home, at school, or somewhere in my immediate neighborhood.

Now I live in New York City. In a big urban environment, everything changes. The options for how to spend your time are infinite. Our doors are always locked. I meet my wife at the subway station if she finishes work late. If it’s later still, Uber or a cab wins out over public transportation and she uses “Find My iPhone” to share her location.

Urbanization, more broadly, is a macroeconomic trend. People everywhere increasingly choose to live in and around big cities, and that requires different rules and protocols for how you navigate the world. It’s not good or bad per se, just different.

You might think about the internet in similar terms. Back in the year 2000, if I was spending time online, I was sending an email, chatting with friends via AIM, or playing a game. A couple of years on, I had an iTunes account and wasted a bunch of time on Facebook. A handful of accounts on a handful of different services.

Today, we operate in the digital equivalent of New York City. My phone has 75 different apps on it all requiring unique accounts. 9 finance apps, 5 social, 8 travel, 5 transportation, and on and on.
At work, there’s a completely different set of apps you use. There’s your work email, CRM, expense platform, and many more.

But despite leaving the digital countryside for the big city, many people (and businesses) haven’t made any changes to how they navigate the digital world. They spend virtually no time or energy worrying about the internet’s version of locking your doors and safely navigating to different digital destinations.

In slightly more literal terms, we’re building a software company called Idenati (pronounced “identity”) to help businesses and everyday people be a bit more thoughtful about their security when using the internet.

You can click here to sign up for free if you want to check it out and join us on our journey!