That Time I Left $60 Million on the Table

“This is God View.” Austin Geidt was radiating so much excitement, I thought she was going to slip off her bar stool at Mead Hall in Cambridge, MA. As she scrolled across the Google map of NYC and SF, a few little black car logos were ticking up and down the streets. “I can monitor everything happening on our platform from this one view — which drivers have the app open, which cars have clients in them, which areas aren’t being serviced well enough. One day, there will be thousands of cars on this screen.”

Meeting Travis

The heat on my interview with the relatively unknown 20-person startup called Uber quickly ratcheted up to incinerate. Their Co-Founder and CEO, Travis Kalanick, was in town for business, and he was eager to meet me as a candidate to lead the launch of their Boston office. Riding high off the sale of his peer-to-peer file sharing company Red Swoosh for $19MM, Travis was clearly eager to prove he could swing for the fences with Uber. With $12MM in funding, their expansion plans had begun.

It was a Tuesday night, 8/30/2011, when I sat down with the dark-haired impresario. I prepared for the conversation by playing Kalanick’s interview with Jason Calacanis on loop for a couple hours at the Cosi down the street. We spent the next hour feeling each other out. I grabbed a beer, he ordered a water. We grilled each other on ideal team structure, business models, my experience at LevelUp, and his grand vision for Uber. Having previously used the $50 in credit given to me by Austin to get to the U.S. Open in Flushing, I openly wondered how the average millennial was going to choose a $50 black car ride from Brooklyn to Queens over a short subway ride, and Travis alluded to one day going beyond black cars. The conversation ended with a smile, handshake, and promise to push me forward in the interview process.  This could be the beginning of something big.

Before I tell you how it ended, let’s revisit how it all started.


A tweet from a close friend of a former colleague, who started using this awesome on-demand car service in SF and NYC, caught my attention.

A couple weeks later, I stumbled upon an article in TechCrunch announcing Uber’s intent to launch in Chicago, Seattle, Boston, NYC, and DC. Two years into my tenure at LevelUp, I had no intention to leave. I was a top performing sales rep about to lead the mobile payment startup’s expansion from Boston and Philadelphia to eight cities across the country. Most startup workers would die for the opportunity. But still, I was intrigued.

The Cover Letter

Dear Garrett, Travis, and Ryan,

I’m a hardcore Bostonian.  I eat Boston (think uBurger), drink Boston (think Stoddards), and live Boston (think Blue Man Group without the face paint and percussion skills).  I grew up in a nearby suburb and studied Economics at Tufts University.  Many late nights were spent gazing at the city skyline from the rooftop of the Tufts library plotting how I would take Boston by storm. After following your successes in California and New York, I am quickly realizing that the storm is a hurricane, and that hurricane is Uber.

I’m a thoroughbred startup guy.  I started the Beanie Baby Newsletter in middle school and 80/20 Booksellers in college. After spending my second summer of law school building TapInko at the Dreamit Ventures accelerator, I knew I was destined for startupland. I spent the last 18 months growing SCVNGR from 15 to 70 employees, driving over $100,000 in sales over 6 months while managing the brand new SCVNGR Conferences vertical, leading a team of 8 to go live with over 400 local businesses on SCVNGR rewards, and debuting SCVNGR’s Levelup pilot in Philadelphia with top quality merchants.

I’m loud.  I thrive on building both local excitement and national awareness for products and services.  At Harvard Square’s MayFair last Sunday, my marketing team and I took home over 800 email addresses for LevelUp Boston and a nasty sunburn after only 5 hours.  I embrace guerrilla marketing tactics at conferences and fairs as much as I enjoy speaking at events like AMPSummit, NokiaTalk, MobileMIT, Wharton BizTech, Geoweb Summit, and the upcoming Nordic AppWorks Conference in Oslo, Norway.

I love taking brand new products to a fresh market, especially products that I can get excited about.  I’m enamored by Uber’s disruptive model.  Bostonians have been waiting for the Uber solution to get them home from the theater district after a hot Saturday night date, from the financial district after a big interview, and from Fenway after a Sox game.  Boston is my home, and I would feel privileged to be considered for the Boston City Manager position at your incredible startup.

I look forward to hearing from you soon.

Best regards, John Valentine

The Interview Process

It didn’t take long for me to get engrossed in their interview process. First, I had to answer a few questions for Athena Maikish about how Uber should go about dominating Boston. the next week, I was given an Excel challenge in which I had to draw conclusions and make recommendations based on a data set from a number of days worth of rides in NYC. After a 1-hour VLOOKUP refresher course on YouTube, I sat in the lobby of the Sheraton Philadelphia and cranked out charts and graphs to make sense of the huge data set.

I wasn’t the first applicant to tackle the Excel challenge, and as I started poking around I heard disappointing tales from a bunch of people I knew that had failed to pass through the data gauntlet. Fortunately, I made it through.

Having received the green light to start salary negotiations, I spent the next week in NYC taking calls with Travis and Ryan Graves in between pitching restauranteurs to launch on LevelUp’s mobile payment platform. Boston’s launch date was set. My salary was set. My equity package was negotiated. All that was left to do was sign the employment agreement and put in my two weeks notice.

I asked LevelUp’s COO and my good friend Michael Hagan to Sunday brunch the day before my decision was due. Michael couldn’t contain his excitement about LevelUp’s 8-city expansion, and extolled the virtues of being a part of something special from the beginning through massive scale. Either way though, he would respect my decision. “Michael, if I show up tomorrow at work at 9am, I’m in. If not, I’m out.”

The Goodbye Letter

Ryan, Travis, Athena, and Austin,

First of all, I’d like to thank all of you for taking me through your interview process, challenging me, and putting in time and effort to determine whether I was a good fit for your team.  I’m convinced that I would work incredibly with all of you, and that we would make Boston a special city for Uber.

But there’s this thing called LevelUp.  I’ve been with the startup through its ups and downs, twists and turns, good pivots and bad.  If you had pushed me through the interview process at the outset  (while LevelUp was experimenting with deals) the decision to jump would have been much easier.  At its current state, LevelUp is sitting at the calm before next week’s rapid expansion, much like Uber was a few months back. I am one of the two linchpins for the expansion.  

While I’d certainly have a major role in Uber’s success immediately in Boston and in other capacities down-the-line, the ability to both open and later manage a portfolio of cities for the company I helped grow will not only give me upside monetarily, but more importantly allow me to make macro decisions that move entire company.

Before falling asleep last night I asked myself where my heart was, and I chose LevelUp.  It’s where my heart is right now.

I know you’re going to dominate here in Boston.  Think Seattle x2.  Good luck in finding the elusive GM for Boston and the rest of your cities.  Another good fit is certainly out there.  We like to think we’re pretty sharp here in Beantown.

Cheers, John

The Aftermath

I spent the next three years building upon my successful tenure at LevelUp. We did launch those eight cities, and I spent almost two years building out our restaurant network with 25 of the best salespeople I’ve ever known. I wouldn’t trade those flights, strategy meetings, customer service visits, announcements, and team dinners for anything in the world. Towards the end of my time with LevelUp, we expanded to build custom mobile payment and loyalty apps for mid-size and national brands. I went out on top, with very little left to prove.

I knew Uber was going to be successful, but few at the time could have predicted its meteoric rise. Michael Pao took the Boston GM position, crafted “surge pricing,” and just left to be an EIR at Greylock. Uber went on to raise over $10B over 14 rounds of funding, most recently with a valuation of $62.5B. Contingent on my staying at Uber through full vesting and their valuation holding strong or growing, I would have been staring at stock certificates worth tens of millions of dollars. Unfathomable amounts of money.

The Lesson

Life is like one of those “Choose Your Own Adventure” books you read as a kid. Every big decision is a fork in the road. You make a gut call and flip to page 35. The only difference is, in life, there is no peeking or turning back.

For every Uber, there are thousands of other startups that simply tread water or sink under the weight of a bad team, terrible business strategy decisions, or superfluous funding. Did I get hit with little pangs of second-guessing with each funding announcement to hit TechCrunch? Yea, definitely. Did my first dozen Uber rides around Boston sting a little bit? Sure. Did it fade over time? Yep. Am I the only person that has ever missed a lottery ticket like this? Hell no.

For every missed opportunity in my life, there have been hundreds of great decisions. Like joining a small startup called SCVNGR founded by an 18-year-old wunderkind with a $500,000 check from Highland Capital. Like marrying the woman of my dreams surrounded by incredible friends and family. Like recently joining MassChallenge, one of the few organizations to dream of a worldwide startup renaissance and have a damn good chance of actually making happen. Instead of hustling with one startup, my work has a daily impact on hundreds. It’s a beautiful thing.

For all those agonizing over your next big decision or lamenting a missed opportunity, you are only on page 20 of a thousand page story.

That Time I Left $60 Million on the Table

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