The first time I had sex I was seventeen.

I can’t say I was incredibly attracted to her, or that I even liked her all that much, but I’d finally met a girl who didn’t want me to drop her off at her boyfriend’s apartment.

It was tough to compete with apartments.

That year I had almost set a school record for most days absent, while dropping girls off at their boyfriends apartments. I was trumped only by Ashley Summers, with her innate ability to manipulate male authority, who beat me by 8 days.

As for our relationship, there were no dinners. No romantic notes in class or long phone conversations where we’d rather fall asleep on the phone than hang up. I never even met her parents.

I had no idea what I was doing.

Our relationship was built on skipping school and laying in bed. This was arguably better than skipping school and laying elsewhere, unless it was laying in Bjorks bed. That would have been better.

After the third day we didn’t have much more to talk about and there really wasn’t anywhere to take it except “is this really going to happen?” There was the usual squirming foreplay but this time we both knew where it was headed.

“Am I doing this right?”
“Is this all it is?”
“This IS all it is!”
“I’m Doing Sex!”

The first thing I recall out of her mouth was “maybe next time we can do it a little longer,” followed by “you are number fourteen you know.

Fourteen! Who were these other thirteen guys? They probably all had apartments. I couldn’t compete. I had no idea what I was even doing. I had to break up with her immediately.


Hiring our first employee we tried to do everything right. We spent months scouting him, trying out small tasks before he moonlighted as our lead designer on several key projects.

We flew him in from Las Vegas to San Diego for a weekend to woo him away from his current position. We put him and his significant other up at the nicest hotel we could afford (it had a rooftop pool!). We showed them all the amazing things San Diego had to offer in a two day blitz of the city.

We had just taken on more work than we could reasonably handle for some very large clients. Large clients meant large nets and we weren’t going to see a dime for three to six months. We were in over our heads on all angles and we knew it.

We needed a young jack of all trades and he was a perfect fit. A designer who could hack through a frontend interface and loved terminal. All he needed was some good leadership and the rest would take care of itself.

But I had no idea what I was doing.

At first things were great. We were so busy knocking out multiple large-scale applications with insane deadlines that we had no time to think. But as we finished those projects we moved into murkier waters. We suddenly had time to breathe and I needed to find a direction that was both challenging and profitable.

I was right back there — squirming around. Looking for affirmation that my decisions were suitable. That I really could lead someone who was more talented than myself.

Again, we tried to do everything right. Free Lunches. Expensive dinners. All expenses paid trips to tech conferences. We had paid gym memberships. We had weekly Yoga. We treated our neighbor’s Foosball table as our own. We even gave large year end bonuses.

But in the end, I was a terrible leader. The signs were all around me. He was visibly miserable coming into the office. What started off as working until the day’s work was done soon became a five o’clock sprint for the door. We couldn’t offer a salary as high as the buzzing recruiters. Our benefits were non-existent and I was too scared to offer the direction and critique that he needed to grow. I let this erode my confidence and ultimately lose our first hire.

When he finally took another job offer, it stung a little. Not because we wouldn’t have his amazing talent floating around the office. Not because we had built our entire marketing campaign around his designs (which had just hit the front page of Dribbble). But because I knew I had failed. I knew that I hadn’t delivered as a leader.

Leadership isn’t always about your company culture. It isn’t about perks at work or how many free lunches you give out. You can’t buy yourself leadership.

It’s about pushing people farther than they thought they could go. It’s about creating results that are bigger than our sum. Most importantly leadership is about inspiring people to be better than they currently are. Without this type of magic, our team splintered.

While I would have loved to say I nailed it, I’m thankful for getting it wrong the first time. I wasn’t ready then but I’m ready now.


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