You Can’t Plan for This: Unexpected Twists and Turns While We Pitched our Vision

by Kimberly Shenk

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I look back at some of the pressure-cooker moments we had during fundraising. You can’t prepare for it. You can’t make this stuff up.

We were at one of our very first venture capital meetings in Menlo Park. Nervous excitement filled the dimly lit conference room.

“Do you mind if I bring my two interns?” she asked. Of course we didn’t, we said. So she let them through the conference room doors.

We stood up, shook hands, and introduced ourselves. The first intern was in college. The second proudly announced he was about to be a junior in high school.  

We gave all three of them our memo. Meant to be consumed in 15 minutes, the VC finished it on time. The high schooler was still on page three.

This is the point where we would start discussing the business. She would ask us questions. We would engage in healthy discussion.

Instead, she pulled out her phone and began to check email while the high school junior painstakingly read every sentence.

He finally finished. We had a spirited back and forth with her. She told us her concerns. She gave useful suggestions. I took copious notes like a good student.

Then junior pitched in. He had marketing advice based on his month of internship experience. I nodded my head inquisitively and scribbled in my notebook. Was this a Seinfeld episode?

We didn’t get that investment. Maybe the high school kid didn’t like our idea. But it taught us to be prepared for anything.

Until a couple of days later when we found ourselves on Sand Hill Road meeting with another venture capitalist.

Jaleh and I started as usual. We gave our introductions and then explained why we had a memo and no deck.

He brushed past that point and introduced himself as a Harvard Law School graduate who had been investing for years. We passed him the memo.

“I’m sorry but it will take me all day to read this. I have dyslexia,” he said.

I thought law school was all about heavy reading so I giggled politely. Then I realized he was serious.

“You will have to pitch it to me.”

We awkwardly walked him through our idea.

“Do you have any feedback?” we asked.

“Just so you know, investors like myself have been doing this for years and we always expect a deck. We don’t like change. I recommend you put together a deck for your next pitches.”

He didn’t invest. And we didn’t create a deck. But we did practice pitching without materials.

A week later we found ourselves anxiously waiting for news from another investor. We had just pitched his entire firm and they were deliberating.

While sitting in the Capital One Cafe in downtown San Francisco, mooching off their free wifi, we received a one-line email from the investor. He had feedback for us.

Uh oh. Feedback? Feedback does not sound like an investment.

Even worse, we had just signed a lease for a coworking space.

We started talking about all the things this venture capital firm probably didn’t like. And concluded they probably weren’t a fit for us anyway.

We decided to cancel our lease. The cafe was working just fine for us. Jaleh called WeWork right then. We felt good about our frugal decision.

Then Jaleh’s phone rang. It was the investor. She walked outside the cafe.

I waited anxiously.

Suddenly she was rushing back into the cafe, still on the phone.

“They want to invest!” she mouthed.

What?!? I was shocked.

A term sheet came shortly after with an offer that was exactly what we’d hoped for. All the preparation in the world couldn’t have prepared us for that moment.

And, we still don’t have a lease. We’re actually happy about that last-minute decision. Our kitchen tables work just fine. We have coffee and wifi —  and our cute dogs love it.

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