Zimride. This was when the “rays-of-sunshine” pattern was super popular for startups.

Rideshare Wars, Part 2: How did you know?

This is part of a series of posts dedicated to telling the story of building the most incredible startup of this decade, Lyft.

One thing a lot of people ask me these days is “How did you know?” As in, how did you know in 2011 when you first met John and Logan that Zimride would turn into something so transformative. They’re hoping that my advice will help them make the right career move and find the next Lyft, Uber, Facebook, Twitter, Linkedin, AirBnB, etc. The truth probably isn’t that surprising: I didn’t know. No one really does. It’s why so many VC investments fail and those guys have teams of analysts way smarter than you and me evaluating deals.

At Zimride, a seed/series A startup with revenue that depended on a long enterprise sales cycle with the two slowest-moving entities in existence (big companies and universities) it was impossible to know.

The consumer market we were (still are) tackling is enormous and marketplaces with critical mass are nearly impossible to dethrone. Zimride was building that marketplace in a space where you could count the number of competitors on one hand: Ridejoy (YC-backed, gone), Carpooling.com (threatened a US launch for years, hasn’t happened), BlaBlaCar (doing very well in the UK… now), Craigslist (who has ever heard of them), and some other players tinkering on the edges or focused primarily in international markets. Zimride’s mission was great, the product was still trying to hit its stride, but the people… they were (and still are) amazing.
There is much written about considering and evaluating your transition to a startup, but mine went something like this:

Background

It’s 2011 and I’m working at Shutterfly running the business side of the eCommerce team. I’ve been in this space now for five years (ofoto and Shutterfly) and doing the same thing for the last three.

I live in the Oakland/Berkeley border and this commute to Redwood City is killing me slowly.

Everyone who is senior to me is a white male with an [insert Ivy League School] MBA who was an early employee at [insert now-too-big-to-fail-early-internet-startup-usually-eBay].

It’s the middle of 2011 and we’re locking down the 2012 roadmap which will be very difficult to change once locked down.

What am I doing with my life/do I want to keep doing this/how do I take my career to the next level/what is going on/am I learning/why am I not excited about this job?

Options (no, not those options)

Given where I am, what I’m observing around me, and my risk profile I saw myself having one of two options:

Option 1

I can go back to school and get an MBA then hope to get a good job where I have a step-function change in salary or responsibility.

Option 2

I can join a startup, punch a little bit above my weight class, and get my experience the good old-fashioned way — working.

The Process

Here is my three-step process for choosing Option 2 and then deciding Zimride was the right move for me (note: shortened from a 100 step process for readability):

Step One: Inner Monologue (stream of consciousness)

MBAs are expensive and I’m making a great salary now | I have an undergraduate business degree from one of the best schools in the country, I don’t know that I’ll learn much more | I’m already in marketing, which is where a lot of people want to transition to when they get an MBA | My wife has a graduate degree; isn’t that enough? | Oh look, here’s an interesting job opportunity for a Director of Marketing role at a Series A startup | Maybe I should explore that.

Step Two: Meet Logan

This office is a lot of concrete and metal, it’s different. This neighborhood smells funny and I think I stepped over a river of urine a half a block up from here.

Who is this guy named Nasim* I’m supposed to meet?

There’s a dog in this office. I hear it’s Kevin Rose’s dog. Who is Kevin Rose?

Where is John? Oh, he’s down in LA working on a Zimride deal with LiveNation.**

Logan seems really nice, we’re hitting it off, and there’s a desk here that you can raise and lower with a button.

Hopefully he doesn’t think I’m a complete joker and I can meet some more people.

Logan is really passionate about this company’s mission.

[END SCENE]

Step Three: Meet John

This guy has a great face for bizdev. He’s from upstate New York, I know some people from there.

He shows me Zimride’s ethos which is written on the wall. It starts with “Communities aren’t born. They’re made.” I like this.

I can tell he’s evaluating my cultural fit for the company; that’s one thing that John is very good at. I think I’m a fit.

John is also really passionate about this company’s mission.

[END SCENE]

Turns out, no one thought I was a complete joker (probably just a partial one, which fit in with the culture). I was a bit more sold after meeting Logan and John, but I still had a long road ahead before joining Zimride.
In Rideshare Wars — Part 3 I’ll cover the rest of my interview process and our early days at Zimride.

Footnotes:

*Nasim is not a guy. She’s a wonderful woman who started as Zimride’s Office Manager/EA and is now an HR Manager (and close friend) at Lyft.

**If you’re a small company think twice before you try to do a deal with LiveNation. Even if the CEO is a potential investor there is a high likelihood that this deal will NOT 1) move fast or 2) work. Both true in our case.