September Capital

Knowing When to Call

As Skip left his partner Dan’s office, his pace was a little faster than usual. He wasn’t quite running. But had he sustained that pace, he would have been a reasonable contender in one of those silly walk races he’d occasionally happen upon on ESPN2. He could have blamed his pace on the adrenalin rush of getting the go ahead on a twenty million dollar investment in ElectricCity. But in reality, he was rushing out of there for fear that his partners would change their minds. Skip bound past Dan’s assistant trying to look nonchalant. He was feeling pretty good about his escape when he heard Noah’s voice calling after him from Dan’s office – “don’t fuck it up!"

Skip’s stride ground to a crawl. He suspected Noah was joking -- mostly because Noah was always joking -- but Skip was also relatively new to the partnership and therefore had a tendency to second guess himself. As he made his way around the corner to his office, Skip began the second guessing. Was he making the right choice here? What if the deal didn’t work and he lost twenty million dollars? How would he recover from that? Were his partners really supportive or would they do a whole lot of “I told you so”-ing if it went south? What did he know about the Apps space? What did he know about any space?

Skip closed his door and called Kitty.

“Hey.”

“Hi honey.  What’s up?”

“They all want to do the deal.”

Kitty’s inflection rose with excitement.  “That’s great. I’m so proud of you.”

“Yeah.”

“Skip, why don’t you sound excited?”

“I am. I’m excited. No, I am. But we’re talking about putting in a lot of money.”

“Isn’t that the point?”

“What do you mean?”

“I mean, you are an investor, aren’t you? Isn’t the whole point to invest?”

Skip’s voice dropped even quieter. “Yeah. I suppose. It isn’t the investing part I’m concerned about. It’s everything after that.”

“Everything what?”

“You know. The part where they have to not fail. The part where they have to become a big important company. The part where we turn twenty million dollars into two hundred million dollars.”

Skip’s baby made a little whimper on the other end of the phone. And with that, Kitty was done with playing therapist.  Her voice moved from sympathetic to impatient. “Listen Skip.  Its an awesome deal. And it will kick butt. You should be over the top excited. So stop whining at me and go get the darned deal done. I’ll see you tonight.”

“Thanks honey.” Skip was ten percent annoyed by his wife’s little kick in the butt and ninety percent grateful.

“Go get the deal done!”  Kitty hung up the phone.

Skip knew Kitty was right. She was always right. Despite the fact that she lived in the non-profit world, she had an unbelievable business mind. Kitty was his secret weapon. Thank goodness she hadn’t stayed with that clarinetist after college. That guy was such a dork. Skip knew that if he hung in there long enough, he would win her over. He hung in there long enough.

Despite ultimately winning over Kitty, Skip was not exactly a lady’s man. He had had exactly two girlfriends ever. Jenny, in high school, and Kitty. He never actually asked either of them out on a date. They both had asked him. Not that he was complaining. It had worked out great. But it didn’t exactly make him an expert in wooing.

Now that Skip was married, that didn’t matter much.  Except that Skip had been told repeatedly that the startup funding process was like dating. You met an entrepreneur and fell in love. And once you were in love, you had to hope that the feeling was mutual. Meanwhile, like some crazy wildlife show, all sorts of other suitors are running around puffing up their chests (“we have a two billion dollar fund”), strutting around (the car of choice used to be a bright red Ferrari, but now it was all about the Silver Tesla S), making crazy noises (“the last time I was this excited about a company was when I funded Amazon”), and generally trying to steal away your mate.

Skip took the dating analogy seriously. He didn’t want to look too eager and blow it. But he also didn’t want to seem uninterested and lose ElectricCity to some more zealous suitor. He sat in his office contemplating how long he should wait before calling to make an offer to fund the company. Skip knew that if he called too quickly he would appear overzealous and lose what little leverage (and dignity) he still had. It was now 10:00am. Skip thought that perhaps the next morning would be the right time to call.  Or maybe 3:00pm that afternoon. At the soonest.

Skip sat at his desk contemplating the perfect time to reengage. As he did so, he browsed through the online news site TechMeme. Even the day’s salacious headlines (“Why VCs are Stealing your Soul” “The Death of Microsoft – Long Live Microsoft” “Women Founders Get No Support”) couldn’t hold his attention. He thought about calling Kitty back, then heard her voice in the back of his head – “go get the deal done” – picked up his phone, and dialed the founder of ElectricCity.  It was 10:05.