To Avoid the Perils of Get-Rich-Quick, Work With People Who’ll Play the Game Again (and Again)

Why is it so irritating to be nickel and dimed?

There is of course a financial aspect (you’re trying to take more of my money) and one of expectations (I might have paid $15 if you’d quoted me that, but you told me it was $10 and now you’re asking for $15).

But perhaps more important is the message you’re sending: a few extra bucks on this transaction is more important to you than our relationship.

In an extreme case, that behavior is completely rational (even if dishonest). If you weren’t well off and had limited future opportunities, you’d probably opt to “nickel and dime” Bill Gates for a million bucks.

In most real world cases, it’s a little more dubious.

Prisoner’s Dilemma, Over and Over

Everyone knows about the Prisoner’s Dilemma, in which the rational strategy for both arrested parties is to testify against their partner. This results in a situation where both men wind up worse than if they’d colluded and remained silent.

In this situation, the players only play the game one time, and almost inevitably wind up screwing one another over.

However, the optimal strategy in other variations of the game gets a lot more complex. If rather than just playing once, players play an unknown number of repeated games, a “tit for tat” strategy can be a very good one.

In a tit for tat strategy, a player starts off playing nice. He plays nice in subsequent rounds if his opponent just played nice with him, but he plays mean if his opponent just played mean with him. If both players adopt this strategy, they’ll wind up colluding and they will consistently help one another out.

Playing the Business Game Many Times

Business is usually both more enjoyable and more successful when your co-players expect to play the game repeatedly.

I can try to extract as much value out of you from you as possible for the thing I’m working on right now. That may mean taking your money, driving you to overwork yourself on my behalf, or getting you to do me favors. I’ll probably be better off tomorrow than I would have been, but you won’t trust me and I won’t be as well positioned the next time I play the game.

Or I can work with the expectation that we’ll play the game again: by doing a little more for you and asking a little less, you’ll treat me well in the future and we’ll both wind up better than we otherwise would have.

Oddly, those who likely have the most games in front of them — new professionals just out of school — are generally more likely to act like they’re only playing the game once. When I first started working, I didn’t have the experience of working with the same people at different companies.

Sure, I might have thought, I’m working with that guy now, but could I really have imagined that I would be part of his company or he of mine ten to twenty years down the road? Probably not: I didn’t fully internalize the importance of investing in relationships.

When, later in your career, you’ve had the experience of working with one person two or three times, you see the pattern. You realize that for any of your colleagues, this may not be the last time you work together.

LinkedIn is, at its core, an embodiment of the importance of ongoing professional relationships. Keith Rabois recently mentioned that an amazing five of LinkedIn’s first twenty-seven people (Keith, Lee Hower, Reid Hoffman, Josh Elman, and Matt Cohler) are partners at VC firms; in large part, that’s because each plays the game collaboratively, with the expectation that there will be many future iterations. Keith, Lee, Reid, Josh, and Matt are all in it for the long term.

It’s very easy to adopt a mentality that prioritizes the thing that’s in front of you. In business, that often manifests itself as a get rich quick scheme.

If your goal is success right now (screw the future), you can spend time with the nickel-and-dime, get-rich-quick types. If you’re interested in the longer term, I suggest working with people like Keith, Lee, Reid, Josh, and Matt.

Why ‘A’ Players Should Collude

They should have been paying me more.

That was my thinking, at least. I was building predictive models for PayPal to detect fraud, and my models were effective at saving the company money. From 2002 through 2004, that work was likely saving PayPal at least ten million dollars a year.

Knowing how much I was helping the company, I figured I’d have some pretty sweet leverage if I ever wanted to try to negotiate a better pay package. My work was easily quantified, and it was making a big difference.

If my models were capturing an extra ten million bucks, surely the company could reward me with half that, or at least a quarter of it, right? Especially since PayPal was being valued relative to earnings; at a multiplier of 30x earnings, those models had created an extra $300 million in shareholder value. Even a few percent of $300 million would make my day!

(At the time, I was not the type to “lean in” and negotiate harder, so that never came to fruition — but that’s a separate story.)

The Non-Zero Baseline

Sadly, my thinking was flawed. My assumption was that the baseline — the business equivalent to the “replacement” player in baseball was a business that was exactly break-even. I could add $10 million in profits, four others could do the same, and the company could effectively divvy up those $50 million in profits among the five of us.

The problem is that the baseline for PayPal — what would have happened with average players at every position — wasn’t zero. The baseline was a business that was losing hundreds of millions of dollars a year.

So I was saving the company $10 million per year, so were perhaps nineteen of my colleagues. My statistical models were ‘A’ work and a huge improvement over the baseline, but so were our fraud policies, our viral growth channels, our eBay integration, our legal maneuverings, and many other areas.

Without all of those accomplishments, PayPal would have gone on losing hundreds of millions of dollars until we went out of business. If the baseline of mediocrity was a business that lost $180 million per year, adding twenty strong people (or teams) whose “above replacement” value was each $10 million per year could collectively improve our bottom line by $200 million — but that would still only lead to a business that made $20 million in profits.

In that sort of business — which is roughly what the pre-acquisition PayPal of 2002 looked like — my original reasoning made no sense.

Collusion Is Good

Recently, I’ve been evaluating a new startup idea. It’s something that’s as ambitious as PayPal, but also just as fraught with challenges: there are a lot of ways that it could lose money. And that’s encouraged me to revisit some of my PayPal memories.

One of my biggest lessons is the importance of team quality for such a difficult and ambitious company. Looking back, it’s as if a bunch of smart and hard-working people colluded and decided to work together on a business that would have failed if we hadn’t all worked on it. Without that collusion, PayPal wouldn’t even have a Wikipedia page, let alone a huge business or a mafia.

2002 was the ideal time for that sort of collusion, because there weren’t a whole lot of options in Silicon Valley. No one was starting their own company, and the list of hot private companies I was aware of had exactly two entries: PayPal and Google.

To solve the toughest problems — and building a slightly more elegant social networks doesn’t qualify — one still needs that type of collusion from ‘A’ players. The good news for founders is that Silicon Valley is attracting more talent than it was in 2002; the bad news is that starting a company has become cool again (I’m guilty too!) and the hot company list has grown from two to dozens.

Collusion generally has a negative connotation, but in this context it can be a very good thing. If, rather than spread themselves among ten mediocre companies, ten all-stars can be like LeBron (and Dwyane Wade and Chris Bosh) and collude, they can see better results and solve bigger problems. And unlike LeBron, they don’t have to do it in zero-sum games.

A Founder’s Constant State of Rejection

When recruiters ping me about open positions at hot companies, I tell them “thanks, but the next company I work for will be (another) one I start myself.”

It’s not clear whether I’m masochistic or just dumb; life was a lot easier before I got started on this whole founder thing.

An Easier Existence

The first seven years of my career were pretty straightforward. I was either an individual contributor or leading a small team inside a larger company. Within a year, I’d figure out a few things I could do to be successful, and I was able to cruise along easily.

PayPal hired 22-year-old me in 2000 to help solve the company’s massive fraud problem. For a few months, I didn’t really know what to do and flailed around a bit. But I soon created a template for predicting fraud, and used it repeatedly to apply a few techniques to solve many fraud problems. I was an individual contributor and making a comfortable salary; though I was working hard enough, my job lacked major challenges and I had little stress.

From there I went to LinkedIn, where I spent two and a half years leading the data analytics team. I faced more stress at LinkedIn than I had at PayPal: I had to hire people, I had to meet regularly with LinkedIn’s executives, and I was a lot closer to the company’s decision-making. Moreover, while at PayPal I had a known problem (detecting fraud) with an unknown solution, at LinkedIn I had an unknown problem (lots of data; what to do with it?) and an unknown solution.

Still, while I was at LinkedIn, my work-related stress was almost nil. I was occasionally exasperated by my colleagues’ decisions, but what could I do? LinkedIn’s successes were nice but hardly life-affirming; its failures made me roll my eyes but not search my soul.

In these larger companies, I found myself in positions where I was almost assured of success: I was skilled and solving problems I knew how to solve. I’d soon learn that life as a founder is completely different.

Founder Changes

When I co-founded the company that became Circle of Moms, I fount that my day-to-day responsibilities changed greatly. Instead of working in a cubicle in a huge office, I sat across from my co-founder at my kitchen table. Instead of asking IT to set up a new database for me, I figured out how to do it myself. Instead of asking a marketing person to write copy for the emails I wanted to send to users, I wrote the emails. Instead of being the crazy analytics guy the engineering team would never want writing production code, I coded the whole darned site myself.

And those are the unimportant changes. Here’s the important one:

A founder must continually put himself and his company out on the line for others to judge.

For an asocial geeky dude, that was an enormous shift. At LinkedIn and PayPal, I rarely took big risks and didn’t have to put myself out on the line. As a founder at Circle of Moms, I did it every single day.

When you’re a founder, your company defines you. That means that your company’s daily ups and downs become your personal ups and downs; that’s a big adjustment.

I’m a fairly even-keeled person: when my co-founder would jump up and down with excitement after seeing good feedback on a new feature, I’d describe it as “encouraging”. I maintained a healthy lifestyle over those 4.5 years: I exercised almost every day, I ate a home-cooked dinner with my wife most nights, and usually maintained a good balance between working hard and living the rest of my life. Nevertheless, I’d still leave the office on many a Friday night completely despondent about the week I’d had, worried about the company and its prospects.

Five Ways to Fail

A consumer Internet company must do well in five areas: product metrics, revenue metrics, hiring, team culture/productivity, and fundraising. In the four and a half years I spent as CTO of Circle of Moms, we never had a time when all five were on a great path.

Just after we launched the site, our product metrics were excellent, but thanks to the financial crisis investors weren’t eager to invest in anything. In 2010, our revenue numbers were excellent, but our traffic stats were dipping. In early 2011, our traffic recovered strongly, but we had more trouble selling ad inventory.

Team culture may be the area where founders take success and failure most personally. If I showed up at 7 AM and left at 8 PM, made honest appraisals of company strengths and weaknesses, and took full responsibility for my failures, shouldn’t my colleagues do the same? And if they didn’t, was it a personal rebuke of me?

Good founders feel strongly about establishing the right environment for a happy and productive team; that’s surprisingly hard to do. A challenging but not unusual week might feature one employee taking an extra day off after a vacation, another one calling in sick with an important deadline the next day, and two others playing big-company-style political games against one another.

Those three ordeals were independent of one another and seem small in retrospect. But at the time, I felt like the roof was caving in: our employees were rejecting my leadership and they were getting lazy, political, and unproductive. The end was surely near.

Likewise, hiring is vitally important and requires thick skin. At Circle of Moms, we’d reach out to dozens of top candidates and usually hear nothing in response. I’d spend a full day at Stanford pitching our company to CS undergrads — far more tiring than any day I’d ever spent coding. After several months, we’d finally find one good candidate and make him an offer. When he’d instead choose to work for another startup — whose name was well-known to TechCrunch readers but whose vision we didn’t quite get — it was hard to avoid getting flustered.

Raising capital almost invariably features many rejections from investors, even with companies that become very successful. We experienced periods where our traction was good and fundraising was almost too easy (we turned down money from one VC because we saw he hadn’t even bothered to sign up for our product), but we also failed in several attempts to close a larger venture round. It’s easy to see a lack of fundraising progress as a company (and personal) failure: if you can’t raise a lot of capital, there must be something wrong with you.

As a techie individual contributor in a larger company, I could go to work everyday and execute 99% predictably. As a founder, I had to find ways to plead your case over and over — to employees, investors, candidates, advertisers, users — and I got rejected a lot. For an introvert, the amount of pleading and subsequent rejection came as quite a shock.

As a founder, you need to be prepared for this sort of rejection. It should affect you: if it doesn’t, it means you don’t care enough and should be doing something else. But a rejection of your company is a (hopefully) rational move by someone else, and it’s not a reflection on you as a founder or an individual. Don’t take it personally.

Of course, the founder/non-founder divide I describe doesn’t need to be binary: non-founders can and do sometimes work like the founder I describe above. A number of the top people at Circle of Moms took ownership and were truly wrapped up in the company’s success, and that helped us immensely. And those are the best people to have on your team.

Founder or not, taking ownership and repeatedly putting yourself in front of the world to be judged is difficult. But ultimately, it’s a tremendous way to learn, grow, and succeed.

3 Things I Learned at LinkedIn (and 2 I didn’t)

It’s a neat feeling when a story about your grandfather helps you contextualize your own journey.

When Poppop, my grandfather, was a young man, he worked in his father’s store. He would keep detailed records of what people were buying. Poppop tried various promotional strategies to improve sales, then closely examined the results. He found that he had a natural talent for gaining insight from looking at numbers; he realized that gave him a big advantage in business (he didn’t need lots of data or fancy A/B testing).

Later on, Poppop would bring those skills — and a natural ability to relate to people — to a business he started with his brothers. Their clothing company, Rockower Brothers, would go public in 1962; it was acquired by Woolworth in 1978.

That progression — from data-obsessed junior employee to entrepreneur using data strategically — sounded much like my own. For both me and my grandfather, mastery of data and math would be one step of several on the trail toward starting a meaningful company. Unfortunately, he died when I was young, so I never got to directly ask him about those experiences.

It’s tempting to paint Silicon Valley as a unique haven for progress with no historical precedent. As with many similarly bold pictures, that painting contains elements of truth, but doesn’t tell the whole story.

In the first post in this series, I wrote about my relatively confined role at PayPal; it made me comfortable with startup life but didn’t really prepare me for entrepreneurship.

My experience at LinkedIn — where I was the first analytics employee and led the analytics team — did much more to prepare me to start a company. That difference is more about my role than about the company: despite having a strong vision, LinkedIn was not tactically great and the team was not as strong as PayPal’s (it’s unlikely we’ll ever see a substantial “LinkedIn Mafia”).

Specifically, my time at LinkedIn allowed me to grow in three areas:

1) Product ecosystem and distribution

Silicon Valley’s priorities are changing. In the past few years, we’ve seen a collective appreciation for the importance of user experience on product. In the last year or two, the term “data scientist” has become popular, but almost no one understands what big data really means(here’s my answer). Very recently, the term “growth hacker” has become popular (I’ve been so branded), thanks to an understanding that getting people to use your product isn’t just something to hope for.

But almost nobody talks of the importance of understanding an Internet company’s usage ecosystem. Take a new user, and project her activity out a few months. Is she going to get through the signup flow? Engage with the product in different ways? Invite friends? And more important, how does this behavior affect other users on the site? Growth hacking requires an understanding of a subset of the usage ecosystem, but the usage ecosystem is much more than that. A company that does well on growth hacking but poorly on creating an ecosystem ends up providing very little value for its users. That was where we found ourselves with Circle of Friends — Circle of Moms’ predecessor — and a big part of why we decided to pivot.

At LinkedIn, a big chunk of my time was spent understanding the ecosystem. Before that experience, I had only a superficial understanding of virality, never seeing how small changes can make big differences. I knew nothing of the effects of different channels — transactional emails, marketing emails, social emails, SEO, partner referrals, press — on a product’s ecosystem. At PayPal, I crunched numbers. At LinkedIn, I wrote email copy to boost numbers and realized the importance of understanding user psychology. Those skills and interests would transfer nicely to the experience building out Circle of Moms, arguably becoming my strongest asset as a founder.

2) Leadership

LinkedIn was my first experience hiring and managing. There’s a lot of (mostly superfluous) writing on whether leaders are born or made. I won’t generalize, but I will state that I certainly wasn’t a born leader: 26-year old me was a much weaker leader than 34-year old me is.

26-year-old me was a very awkward manager. I felt bad asking my employees to do things for me and I was overly deferential to both my own team and others in the organization. To some extent, that’s my personality and will never change completely. But in two years managing people I gained a degree of confidence and authority as a leader that is absolutely essential for a co-founder. If in 2004 I’d started a company instead of joining LinkedIn, I would have ultimately ramped up and gotten used to managing people, but it would have been a bumpier process (and Circle of Moms was bumpy in its own right).

At LinkedIn, I hired two full-time employees and one part-time employee. All three were older than I was and more educated (two with PhD’s). Hiring was a new experience, and an educational one. In the hiring process, I saw a contingency recruiter misrepresent both sides to increase her own take; I also had a candidate accept an offer from us, only to change his mind when his then-employer made him a counter-offer. When I started (what became) Circle of Moms, I was hardly a hardened and savvy hirer, but I’d at least been around the block once or twice.

Of course, management experience is a double-edged sword for entrepreneurs. We all know stories of those who easily managed hundreds of people in big companies, then struggled to be hands-on when part of a tiny startup. My pre-startup experience — managing a couple of people at LinkedIn but still being mostly hands-on — was about the right prep to start a company. For those who more naturally gravitate towards management, leading a team pre-startup is probably unnecessary.

3) The hubristic belief that I could do better

I continued to build out my longtime side project, Team Rankings, while at LinkedIn. It was becoming more and more of a business. In 2004, I started to charge for premium NCAA Tournament content. In 2005, I started publishing predictive models on the site and charged people to access them. Later that year, Tom Federico started working on the site with me, and we raised the bar on product polish and the branding. Come 2006, we were really cranking on our March Madness product: we built an awesome tool called BracketBrains to help with office pool picks. That March, I was constantly tweaking the site’s SEO, scrambling to keep the server up as traffic surged, and optimizing our marketing messages in real-time. It was exhilarating.

Meanwhile, things were moving along pretty slowly at LinkedIn. I was firmly planted on the analytics side of things. I couldn’t write production code, and had limited places to make user-facing changes. A few months earlier, my friend Jawed had pinged me about joining his new startup called YouTube. I hadn’t been interested then, but after that March Madness experience, I saw things differently: YouTube’s early growth, quick speed of iteration, and small size (around ten people) had some appeal. I had significant discussions with YouTube but didn’t wind up joining them; I probably would have if I’d found online video as interesting and important as a professional network.

In the months following, I became more frustrated with both the slow speed of development and what I thought were some poor tactical decisions. Because I was so close to the numbers, LinkedIn’s decision-making bugged me, and made me think I could do better. Because I had built up Team Rankings and been able to quickly iterate on it, I figured I could also build products better and more quickly (to those who have had the misfortune of working with my code: insert a snide remark here).

What I didn’t learn at LinkedIn

When I started Circle of Moms, I was a crappy software developer (I’m still no superstar). I could write code pretty quickly and solve scalability problems in clever ways, but I didn’t do a very good job architecting a system. That wasn’t the end of the world — we had lots of good engineers who eventually made our code base fairly solid — and I’d argue that for very early consumer Internet startups, an A+ engineer is only a nice-to-have.

I also didn’t have much of a business focus at LinkedIn; I didn’t know or understand much about raising capital, equity, finances, or the role of sales on LinkedIn’s success. At Circle of Moms, my co-founder Ephraim — who was CEO while I was CTO — focused more on these areas. My lack of knowledge here certainly didn’t help, but probably wasn’t the end of the world: it’s much easier for a good product person to learn about business than for a good business person to learn about product.

Moving on

In January 2007, it was time to move on. I told Sarah Imbach (my boss) and Reid Hoffman that I was planning to resign and ultimately start my own thing. Reid sat me down, seemingly to convince me to stick around. In a similar conversation nine months prior, Reid had convinced me that LinkedIn — and not YouTube — was the place to be (it’s nice when your fork in the road leads to honey on one side and sugar on the other). But the dynamic for this discussion was very different: I’d found the honey for myself at the end of the LinkedIn road and wanted to move on to climb a big but as yet undefined mountain.

In that conversation, Reid revealed to me that LinkedIn was very close to bringing on a CEO to replace him, describing the candidate as a very well-respected #2 person at a public company. I was somewhat taken aback, but it made sense: Reid understands his skills (product vision, many different types of strategy) and weaknesses (operational details) as well as almost anyone. It was probably a last-ditch effort to get me to stay, the implication being that LinkedIn would soon be better led and better run. The new CEO, who it turned out would be Dan Nye, would hopefully address the weaknesses I saw in the company and its culture.

Alas, I’d made up my mind and knew where I wanted to go. I’d grown in three very important areas. Like my grandfather who moved on from his father’s store, I was ready for a new challenge.

The Slow Road to Entrepreneurship: Learnings From Early PayPal

We all know the stories: Zuckerberg, Jobs, and Gates dropped out of school and founded three of the companies that define our world. They went from college students to entrepreneurs, no transition required. But that’s the exception; to generalize Dave McClure’s instant classic, those of us in Silicon Valley’s 99.9% have to content ourselves with being relatively late bloomers.

That’s reflective of a larger narrative that dominates much of the talk around entrepreneurship: the narrative implies that one is either 0% entrepreneur or 100% entrepreneur. Such a binary classification implies that entrepreneurs have to go from 0 to 100 in one step. While there’s some truth in that — you won’t completely understand the thrills, stresses, and demands of starting a company unless you do it yourself — you can certainly prepare yourself for future entrepreneurship by being a part of early stage companies with people who can help you learn quickly.

My own story is certainly reflective of that: I wasn’t ready for entrepreneurship at age 21 or 22. By my late 20′s, I was aching and ready to start and grow a company. Here’s how that change happened.

My first substantial job experience after college (following eight months as an engineer at a failed startup) was at early-ish PayPal. I was part of the company’s growth from small in 2000 (a very unprofitable hundred person startup) to huge in 2004 (massive subsidiary of massive Ebay).

As a new employee, I knew nothing about fraud detection and received minimal guidance. Somewhat lost, I added very little value to the company my first few months. Three months after joining PayPal, Sports Illustrated wrote an article about my side project, Team Rankings. I sensed some irritation from my boss Max: I was doing only so-so work at PayPal, but was getting significant publicity for a side project. That irritation seemed unfair to me at the time; having now been a founder myself, I can completely relate. Founders want people on their team executing at the highest level; seeing someone perform better on a side project than in the office doesn’t send that signal.

Fortunately, I soon found my way, and (with some help) figured out how to turn massive amounts of data into statistical models that could accurately predict fraud. I felt like I was living on the edge because I eschewed the “easy” off the shelf enterprise tools others were using. Some 23-year-olds rebel by using mind-altering drugs or traveling the world; for me rebellion was writing software from scratch to build statistical models. And this defined me: any job other than predictive modeling struck me as superficial, scientifically empty, and not worth doing.

My job at PayPal focused and insulated me. In 3.5 years at the company, I did one thing: build technology to predict fraud. Most of what was going on at the company — operations, usage, product, competition, finance — were of no concern whatsoever. I became very skilled in a few very specific areas, but knew very little about the goings on across PayPal.

If I had a publicist, I’m sure he or she would tell me to broadcast that I magically learned how to build a business while I was at PayPal: surely that magic would cement my place as part of an all-knowing PayPal Mafia. Alas, I don’t have a publicist, so the truth will have to do: PayPal taught me very little about how to build a successful startup.

But the PayPal experience was formative in two key ways. First, it showed me that talented, driven, resourceful people with virtually no knowledge of an industry could become skilled in areas they’d never known about before (for me: fraud detection) and collectively build a large Internet business and change the world. Second, my colleagues at PayPal set a bar for the caliber of thought and effort that I now expect from those I work with.

After several great and educational years, by early 2004 my job at PayPal had become routine. Fifteen months after Ebay acquiring us, the company’s combative, execution-focused culture had been swallowed by Ebay’s relentless drive to maximize employee time spent in PowerPoint meetings. I didn’t have deep insight into the business of PayPal and Ebay, but I knew I didn’t want to play the big company game. Yet for financial reasons, I was motivated to stay around to vest my remaining stock options.

Researching my choices, I discovered that Ebay had a policy which allowed employees to work just 24 hours a week, while continuing to fully vest their stock. This held a lot of appeal — especially since I was interested in spending some time helping out some friends who were working on a new site called LinkedIn.

Ebay’s lenient vesting policy was likely designed for new mothers or those with health issues — not 26-year-old males interested in moonlighting at a startup. That didn’t dissuade me: I soon shifted my schedule to one where I worked 3 days a week at PayPal and spent the rest of my time at LinkedIn. And the LinkedIn days were a lot of fun, as I got to work with a small team, focus on a completely different set of data problems, and understand how a social network could rapidly grow.

At this point, in the first half of 2004, my boss Nathan at PayPal was trying (struggling) to find cool stuff to work on, so we spent some time with other groups at Ebay looking for interesting data problems to solve. But I soon realized that once I started to look down upon my employer, it would be difficult for me to do top-quality work. I was still building good fraud models, but I was no longer psyched about my job at PayPal, and the caliber of my work certainly suffered. I admire those who can be completely professional and work at full intensity for anyone at any time, but I’m not like that. When I’m excited about a project and a company, I’m hard-working, clever, and efficient. When I’m coasting, I’m none of those things.

Trying to foster more commitment, Nathan came to me in July 2004 and told me that I had to choose between working full-time at PayPal and leaving. I’m guessing he thought this would push me to increase my commitment, but it had the opposite effect: I was bored, disgruntled and antsy, and I was going to leave. I left PayPal in August and darted off to France for a month of cycling.

At this point, I had aspirations of starting a company some day. I’d had some entrepreneurial experience with Team Rankings (more on that later), and had built up some skills at PayPal. At PayPal, I’d worked on some other side projects that could have turned into their own companies (none amounted to much). But I didn’t have in mind a specific company that needed to be started, nor was I compelled to start a company just to start something. And LinkedIn seemed like an attractive place to be: a strong 15-20 person team, an innovative and useful product, a really interesting data set. So I decided I’d join LinkedIn full-time.

I’d spend two and a half years at LinkedIn. I was the first analytics scientist and would lead what’s now called the Data Science team. Unlike my insulated time at PayPal, my years at LinkedIn would get me very close to the business and the product, piquing my interest in a much wider array of topics. Ultimately, that experience would nudge me to jump off the entrepreneurship cliff and start my own company. In my next post (follow me on Twitter), I’ll tell the story of those two and a half years and of the key experiences that led me to start something myself.