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.

Data Scale – why big data trumps small data

As I walk into a coffee shop, the guy behind the counter sees that I’m in a hurry and that I’m by myself. He’s seen me a few times before, and knows that I don’t usually order sweet snacks. He knows I tip reasonably well. He’s likely to treat me a certain way: efficiently, without small talk, and not trying to sell me a muffin.

In the “real world”, his behavior — and my user experience — is largely the result of subconscious change (in Daniel Kahneman’s terrific book this is called System 1). Online, personalization and improvement of my experience usually comes from lots of data. Offline, the cashier’s “data set” is the personal experiences he’s had. Online, it’s the same thing for the site I’m visiting. The big difference is that most working humans are between 15 and 75 — a difference of 5x. Online, Facebook has nearly a billion users, and my blog has… less than one fifth that number. Online differences are orders of magnitude larger.

That advantage compounds over time, as companies with many millions of users attain data scale. Data scale is the millions of pieces of information that allow a company to improve the user experience in ways that competitors with fewer users cannot. I saw this firsthand at PayPal, LinkedIn, and Circle of Moms: all three companies were able to provide features and additional value to new and returning users because of what we’d learned from millions of others.

Network Effects and Big Data

Network effects are well-known and understood in the consumer Internet world. As Facebook grows more popular, more of your friends are on the site with you, and it becomes more and more useful (or at least, entertaining) for you. And that size distinguishes it from an upstart: why sign up for a new site with just three of your friends when you can be on Facebook with almost everyone? Network effects have clear and well-defined values for both websites and users.

By contrast, consider the opening sentence for the big data Wikipedia entry:

In information technology, big data consists of data sets that grow so large and complex that they become awkward to work with using on-hand database management tools

The entry depicts a purely technical set of requirements, with no bearing on the product or user. But lots of data is more than just awkwardness and data management tools. Companies with data scale can create a set of features and processes — prediction, testing, understanding, and segmentation — that aren’t possible to those with small user bases. Collectively, they allow a company to block access to fraudsters, tailor products to users, and understand them in deep ways. Data scale improves both the user experience and the bottom line.

The 4 Advantages of Data Scale

In my twelve years working with consumer Internet data, I’ve seen four things that companies with data scale can do much better than smaller competitors:

  1. Predict

    Fraud nearly destroyed PayPal’s business in its early years. Fortunately, we figured out how to accurately detect it, and wound up reducing fraud rates by 80-90%. After predicting which transactions were most risky, we’d block and reverse the bad ones — helping PayPal move from bleeding money in 2000 to profitability+IPO in 2002.

    Data scale was necessary for that detection. More transactions — and more fraudulent transactions — give smart scientists the data they need to discover complex but statistically valid predictors of fraud. Start with a set of only 10,000 transactions and 100 fraudulent transactions, and you can put together a few simple rules to find fraud. But with millions of transactions and tens of thousands of fraudulent transactions, our fraud analytics team could find subtler patterns and detect fraud more accurately. A mini-PayPal might have the world’s smartest predictive modelers, but without a large data set, there’s only so much they could do.

    Incidentally, this was a major reason PayPal needed to raise lots of capital. Losing a lot of money to fraud was a necessary byproduct in gathering the data needed to understand the problem and build good predictive models. A “lean startup” approach makes sense in some cases, but wouldn’t have cut it for PayPal.

    User perspective: if a company can figure out that you’re very likely a good, non-fraudulent customer, they can provide you with services they’d never want to offer their riskier users. That figuring out process is much more accurate when they have data scale.

  2. Understand

    Most websites start off with less structured data — their databases contain lots of text. Free form fields are easier for developers to code, and (early on) often make it easier for users to enter information. But unstructured data quickly get messy, and without scale, they don’t allow for easy inferences. But more unstructured data — along with a clever data scientist or two — can be a ticket to intelligently structure and build the corresponding features and insights. A few examples:

    • Until 2006, LinkedIn had no structure around company names. Users could type anything they wanted into a company field, and we had no way of automatically detecting that HP, H-P, Hewlett Packard, and HP, Inc. were all the same company. By parsing the data and matching it against other sources like email domain and address books, we were able to detect that those four names were synonyms. Without manual intervention, those processes are only possible with data scale: one person at “HP, Inc.” with an hp.com email address could be random, but when 97 out of 100 users have that property it’s a safe bet that it’s not a random fluke.

      Having an accurate list of companies allows LinkedIn to better guess who you know, it facilitates good company pages, and by using autocomplete, it improves data quality going forward.

    • Before we built Circle of Moms, we built a Facebook app called Circle of Friends. Less than a year in, with millions of users but weakening growth and minimal revenue, we started to search for ways we might shift our business. We found that moms were creating “circles of moms” and using them more than anyone else was using their circles.

      Data scale enabled us to find that trend, and understand what was going on. And that wound up being the insight that ultimately pushed us toward being a successful company.

    User perspective: younger, smaller companies don’t really know what users want, and thus have to keep their product open-ended. When you use the product of a company with lots of data, they’ve learned what people actually want to do, and you get a cleaner, more structured experience.

  3. Test

    Circle of Moms was fanatical about a/b testing on day one (LinkedIn was not — much to my chagrin — but I digress). But in order to decide between a and b, you need meaningful differences in outcomes. If there’s a large difference (say, 40-50%), then 100 outcomes (signups, clicks, whatever the company is optimizing for) in each group is often sufficient for establishing statistical significance. If the difference is 10% or less, you’ll need on the order of 1000+ outcomes.

    Let’s take a graphical look. Below are overall simulated clickthrough rates (CTRs) for different-sized user bases.

    clickthrough by population size

    [Technical details: I ran a simulation where a company a/b tests a variety of emails or subject lines. Each subject has clickthrough rate between 0.75% and 3%, randomly selected with a uniform distribution. All tests are pairwise, so A is tested against B, the winner is tested against C, that winner against D, etc. Tests are resolved at p=.99. A few aspects of this are unrealistic -- uniformly distributed CTRs, non-improving (on average) subjects, only tests with two participants, the same rules for resolving tests for big user bases and small, etc. -- but it's close enough for these purposes.]

    With a small user base, CTR will be mediocre: about 1.9%, and slow to improve. As a user base gets bigger and bigger, a higher and higher percentage of users wind up receiving a very good, well-tested subject line: big companies see a CTR very close to 3%. The largest improvement comes between 100,000 users and 1,000,000 users — in this case, that represents data scale. Most of our successful emails at Circle of Moms would go to a few hundred thousand or a few million people; we were right on the edge of having data scale. If we’d had fewer users, a high percentage of our users would have been “guinea pigs”. With millions of registered moms, we had (roughly) the same number of guinea pigs, but many more users for whom we could use our guinea pig learnings and send the very best content.

    Note the magnitudes of these differences. With data scale, testing can mean a bump of 50% or more; the testing bump is much less for a small operation. For a product close to being viral, an additional 10% — a “small data” bump — might be huge and a/b testing worthwhile. For a product with millions of users, a 50% jump is large almost regardless of application. On the other hand, for a small product where 10-20% doesn’t represent the difference between success and failure, time is best spent somewhere else. In other words, a/b testing is something every company with a large user base should do; for smaller companies the value varies.

    User perspective: if you’re part of a large group, you likely get better content because of feedback from those before you. If you’re part of a small group, you are more likely to be giving feedback rather than profiting from the feedback of those before you.

  4. Segment

    At Circle of Moms, segmenting was essentially a mix of predicting and testing. After we tested emails and subject lines with small batches of users, we’d create predictive models to figure out which future users would be likely to click on them.

    This meant we could figure out the odds that someone would click on each of twenty possible emails we might send. And we’d send the very best one for her.

    For Circle of Moms, predictive models were relatively simple and didn’t need as many users/observations as PayPal’s did. But because we were testing twenty different emails at a time and didn’t want to test everything on everyone, scale still mattered. 50,000 people is usually enough to create a model; multiply that by 20 and you have a million. That calls for a million people just in the training set (i.e., the guinea pigs). If you only have 1.5 million users, the benefit of this type of segmentation will be small — 2/3 of users will have received a “random” email to gather data for the models. At 5 million, a company is at data scale, and the vast majority of its users (80%) will get a personalized email.

    I got started on a segmentation-type problem at LinkedIn — matching people to jobs. Job matching means segmenting people into thousands of buckets (each job is a bucket), rather than only 20. Back in 2006, the quality and quantity of LinkedIn’s data made the job very difficult: 5 million users and only a few thousand past job listings was not enough data to do matching well. Today, with 20-30 times as many users, 7 years of job listings, and some scientists who are likely much better than I, LinkedIn does much better finding jobs for people than I did in 2006. That’s data scale (plus a talent upgrade) at work.

    Automated segmentation is harder to simulate and precisely quantify than testing. But the overall picture is clear: it’s useless at small scale, but usually far more valuable than testing at data scale.

    User perspective: when a company can figure out what you like, they can provide you with content uniquely suited to your needs and interests. The more data they have — both on you and on others — the better they can perform this service.

Things I don’t know I don’t know?

I’m both a data guy and an early stage startup guy, and that generally constrains the problems I see. I left PayPal a little while after the company was acquired by Ebay; I left LinkedIn when it was an 80-person company that I found too slow-moving; I left Circle of Moms after Sugar’s acquisition. That means I’ve never worked on a product with over ten million users. No doubt I’m missing out on some of the advantages that truly massive companies have. Others have more firsthand knowledge on the topic of really big data scale — those of you in that category, ping me about your favorite post and I’ll add a link.

The Visionary and The Pivoter

A tale of two startups

Last month, my startup of 4.5 years, Circle of Moms, was acquired by Sugar. I’m proud of what my team created over that time: the product behind a large and strong community of moms, a set of technologies that allowed us to move quickly and make sound data-driven decisions, and a positive team culture conducive to both good work and employee happiness.

A month out, I’ve had a little bit of time to reflect, and the lessons I’ve learned from the process are still fresh in my mind. By almost any measure, Circle of Moms was a success, but not a “rocket ship”, either of the quick (YouTube) or slow (Facebook) variety. We did lots of good things and lots of bad things along the way, and this is a great time to write about a few of them.

I’m going to recount a few pieces of my experience as honestly as possible, trying not to pretend that we were more clever than we actually were. Circle of Moms has usually been an environment where people are comfortable owning up to mistakes and weaknesses; hopefully I can maintain that spirit and provide some interesting lessons in the process.

What is a Pivot?

A year ago, I wrote about why I was building technology for moms. I outlined the thought process we went through in 2008 when we transitioned from “Google+ Circles for Facebook” to “LinkedIn for moms”.

Our story is occasionally highlighted in entrepreneurship classes as an example of a successful pivot. The term “pivot” has become something of a cliche, but unlike many business cliches it has real meaning. The outline for the pivot story is often abbreviated to:

  • Team has an idea they think is brilliant.
  • They build it out, and find out it wasn’t brilliant.
  • Team realizes that some byproduct of what they built was in fact brilliant. Byproduct = pivot opportunity!
  • They pivot the company in this new direction and immediately achieve success, fame, and fortune.

Does that story apply to what actually happened at Circle of Moms? Yes and no.

  • Original idea not being brilliant? Yep.
  • Byproduct = pivot opportunity? Yep.
  • Immediate success, fame, and fortune? Not so much: the pivot is only the beginning of the story.

The Pivoters

In 2008, when we decided to shift our company’s focus to moms, my co-founder Ephraim and I were guided by both personal goals and a business opportunity. On the personal side, we wanted to create a substantial website that would truly improve the world. I admire Zynga’s data-driven approach and relentless execution, but I wouldn’t derive a lot of satisfaction from building up a casual gaming property.

On the business side, four things were pushing us forward:

1) We were confident we could quickly drive distribution among moms. We’d been very successful with viral growth as Circle of Friends, and Circle of Friends’ viral mechanism had been far more effective among moms than anywhere else.

2) Moms were frustrated with the online products available to them. No good ways to meet other moms, poor information available online, difficulty storing and sharing their kids’ special moments, and decade-old tools to communicate with others like them.

3) Advertisers were willing to pay to reach moms. That meant that with moderate scale, we could get to profitability.

4) Moms told us they’d pay for tools and features that make their lives better and simpler. The now quaint-sounding quip I made in 2008 was that our customers weren’t 15-year-olds who had nothing better to buy than fancy ringtones.

In short, four positive indicators: a distribution mechanism (something all too many startups overlook), a high-level consumer need, and two possibilities for monetization.

Great, right? Well, yes — but there was one key constraint. Let me explain by making a comparison.

The Visionary

When I joined Reid Hoffman’s team at LinkedIn in early 2004, LinkedIn had 250,000 users and similar dynamics on items 1-4: a promising if not fully built out viral mechanism, a strong set of needs from a valuable audience, and a couple of potential revenue drivers. But in Reid, LinkedIn also had one unfair advantage.

Before LinkedIn even existed, Reid forcefully described a changing world in which everyone needed a place to hang their professional shingle. His vision of the future professional world was fluid and efficient on one hand, and relationship-driven on the other. This stood in sharp contrast to both the slow-moving, stay-at-a-company-all-your-life world of the 1960s, 1970s, and 1980s, and the transactional career-oriented sites that grew up in the 1990s. And this vision was truly a manifestation of his life: Reid cares deeply both about making the professional world more efficient, and about fostering relationships that can help all parties involved.

Very few founders have the ability to forecast where the world is going and then mix in their startup’s product. Reid’s correct vision of how LinkedIn could succeed — albeit with tactical shifts along the way — allowed the company to make big smart bets and helped its prospects immensely. The execution at LinkedIn was fine but not exceptional; many tactical choices were sub-optimal; the team was solid but not as the level of PayPal’s early team. But the combination of clarity of purpose, a good distribution model, and an ultimately correct view of the world allowed LinkedIn to overcome a number of challenges and become an influential and highly valued company.

The Two Climbers

Imagine two climbers. The first is a mountaineer. He knows he wants to climb Everest — it’s the most famous mountain in the world. He identifies the best people to help him, maps out the route, understands the challenge. When he actually goes to climb it, he encounters a blizzard and one of his colleagues gets sick — so he has to adjust his strategy. But he knows where he’s going and has a good understanding of how to get there.

Then picture a second climber. His goal is to get up as high as possible. He finds himself in San Francisco, on a foggy day. He knows from Wikipedia that Mt. Davidson is the city’s highest point. He can’t see more than a few feet ahead, but he can tell the difference between up and down, and sets off to cleverly find a way to the top.

Now map these types to two entrepreneurs starting companies. At Circle of Moms, I was the guy wading through the fog (and no, I didn’t have Google Maps on my phone). That wasn’t necessarily by choice: I’d spent several years working for a visionary founder, and would have emulated him had that been realistic.

Though you might not know it from reading popular accounts of startup stories, my non-visionary status wasn’t unusual: a pivoting company almost always starts out in the “fighting through the fog” mode. Circle of Moms was an extreme pivot case, a business largely chanced into by two men without kids. As such, we were unlikely to ever be blessed with an intuitive vision like Reid’s to guide our team. What were the biggest challenges our users were facing, and how was our company uniquely positioned to combine our resources and the technologies du jour to solve them? Those were questions Reid was able to answer instinctively and intuitively about LinkedIn; I found I really had to work to make progress on them for Circle of Moms.

Not having that intuition makes it harder to get one’s hands around a sense of purpose; I don’t think I ever perfected my elevator pitch. It was a challenge to find something like “the place to hang your professional shingle” (LinkedIn), “holding the Internet in your hands” (iPad), or even the smart journal that helps you share life with the ones you love (Path).

Embracing the Pivot Style

We ultimately settled on “motherhood, shared and simplified” as a tagline for Circle of Moms. It’s pithy, but not descriptive: better as part of the logo on a website than as a hook to convince potential recruits to join a team.

Lest you worry that I spent those 4.5 years crying myself to sleep, I’ll assert that tagline clarity rarely makes or breaks a company. But that communication challenge is representative of an area where we weren’t as strong. Like LinkedIn, we did what we could to capitalize on our strengths. In our case, that meant doubling down on execution and making the best of the resources we had.

Data-driven pivoting was certainly one strength of ours, and we were constantly making small shifts. We may not have found the most massive mountain, but we maneuvered the hills around us adeptly. We got features out quickly and then focused on optimizing them. We did well on SEO, figured out what worked on social media, crafted good viral flows, and had success creating and customizing content for email. Early on, we had an ad sales partner who helped us to become an attractive destination for brand advertisers. With revenue from those ad campaigns, we managed to grow the team steadily, while never wasting large amounts of money in unnecessary ways.

We had more trouble in areas like reinventing our home page, coming up with crazy new products, or pulling disparate features into a single experience. And press was probably never our strength.

Keys to Success

All else being equal, I’d rather be a visionary than a pivoter. For Circle of Moms, success happened because we found a good tack and paid attention to our constraints. I never had the vision for Circle of Moms that Reid had for LinkedIn. Yet our team managed to survive and prosper, because of a few key things we did well:

1) Turning the size of our user base into an advantage. Early on, many moms signed up for Circle of Moms, but didn’t do much on our site. In 2011, we built out technology to scientifically test out and optimize many different types of email content. That technology, coupled with a strong team writing new content, allowed us to reinvigorate our base of six million moms. Without that large user base, we never would have been able to find and optimize the best posts.

2) Hedging against Facebook-related risks. When Circle of Moms launched, we were almost 100% dependent on Facebook for traffic; in 2009 many VCs considered that an unacceptable risk and weren’t interested in funding us. That changed so much that 2-3 years down the line, during acquisition conversations with Sugar, I don’t remember the subject of Facebook traffic ever being brought up.

3) Moving away from several ineffective products. Between 2008 and 2012, we had four distinct primary product focus areas: communities of moms with similar interests, Child Page to chronicle each child’s development, local moms’ groups, and blog-style content. I wish we’d found the perfect feature; short of that, the discipline to pull away from things that weren’t working was the next best thing. And our mini-pivots ultimately allowed us to find a path to grow usage 2.5x in our last 14 months as a standalone company.

I’ll be writing future posts on each of those three topics.

Looking back, I’m glad to have both learned and accomplished a lot. Over those 4.5 years, we built a strong team and a community of millions of moms. We succeeded more than we failed. And I left the company in strong hands — Sugar’s and Ephraim’s — when I departed last month. Sugar’s team brings a number of new skills to the table, and I look forward to seeing how the combined companies will address some of the challenges we struggled with on our own.


Thanks to Elaine, Mark, Matt, Ephraim, and Tom for feedback on early drafts of this article