Some Lessons Learned

My (generally good, despite some imagined controversy in the media) year at Google is over, and I've been asked the "do you know what you are going to do after Slide?" question exactly 524,287 times so far. Having considered Slide and PayPal side-by-side I know now what kinds of things I should do, and so here's that part of the answer.

Hard, valuable, and fun.

During the early days of PayPal, I was frequently cautioned by my co-founder Peter to not confuse the causality between hard and valuable. To a freshly-minted computer science graduate with a passion for making things, solving a very hard problem -- any hard problem, so long as it was really hard -- seemed like a good use of my time. Solving hard puzzles (like trying to quickly generate pairs of very large prime numbers on the very slow DragonBall/MC68328 chip) was a frequent, happy pursuit.

Peter enjoyed pointing out that while most things valuable are pretty hard to do, few truly difficult things are of much value at all (the many possible examples are obvious). Underwriting risk in millions of real-time financial transactions per day is a tricky, but very lucrative, business at scale -- PayPal is a valuable solution to real problems that happen to be very hard. Thanks to Peter's admonishments however, we actively avoided solving problems we didn't have to solve (even to my occasional chagrin).

Today, I see this truism taken to a reductionist extreme: precious few problems being solved in Silicon Valley are actually hard. As a prospective angel investor, a common answer I receive to "what are your company's competitive barriers?" is a shrug; sometimes, "speed of execution." "It's actually hard to do what we do" is heard occasionally, but often turns out to be wishful thinking rather than objective self-assessment.

(By the way, with barriers to startup entry seemingly at their all-time low (sans the associated talent shortage), picking harder problems to solve is probably the better strategy. In the last years in particular, abundance of startup capital, celebrification of founders, and "acqhiring" emerging as a viable exit strategy should have all but eliminated the low-hanging-fruit opportunities.)

To be precise: by "hard", I mean technically hard. Hard problems in technology have the advantage of often (not always) having a detectable solution. Invent an algorithm for factoring products of very large primes (in linear time), and you know you have something special. I'm not knocking non-technical hard problems, incidentally: designing great video games is really hard (I should know). But just like producing a hit song or writing a bestselling novel, you won't know you've got one until your audience votes with their feet and/or wallets.

Working on difficult problems is also intellectually more rewarding to an engineer, which is who I am, after all. To sustain that interest though, it's important to work on a fun hard problem, one you are passionate about. As the CTO of PayPal, one of my key tasks was staying a step ahead of the bad guys trying to steal our cusomers' money or break into our servers. Stressful as that work was, I found that I missed this excitement of trench warfare terribly after I left the company.

To be entirely honest, I never fully appreciated this balance of hard, valuable, and fun, taking it all rather for granted. But because I never achieved that balance at Slide, I have significantly more appreciation for it now.

Slide was plenty hard, too. As the CEO of the company, I was often putting out non-technical fires, but generally managed to keep my engineering ear to the ground most of the time. In both categories, there were many challenges, some very intellectually stimulating.

The value we created was delivered to our users on a deeply emotional level, much like a hit song, a great novel, or an addicting video game. The extremely personal feedback we'd frequently receive from our users was a great motivator, and there were great many times I found myself overwhelmed by pride in our team, their intelligence and dedication.

But remaining honest, even as our business evolved towards game-making, I became more and more aware that I was was not very passionate about games.

Despite the hard challenges and the obvious satisfaction we delivered to our users, in the universe of hard problems I was driven to solve, making the perfect game never occupied a central spot, ultimately undermining my perception of the value of my work.


It is clear that the path forward for me is to seek that balance of hard, valuable, and fun in every project I start, join, back, or advise. Hard is for intellectual engagement, the search for solution by any means necessary. Valuable is the knowledge that if this, whatever this is, works, the world will never be the same. Fun is the sense of passion, the wings that carry you out of the pit of despair when nothing seems to work; the first thought upon awakening -- I've gotta get to the office!