Note: I’ve written bits and pieces of this post over several weeks. The other day, our President made his “shithole countries” comment, by which he presumably was referring to Cameroon, among others. It saddens and incenses me that our nation is led by such a disgraceful human being.

Back in 2005, I made one of those big choices in my life from which everything else has since flowed: I decided to join the Peace Corps rather than pursue a career in politics (as an operative, not candidate). My old boss, Lt. Governor Tim Kaine, was running for Governor of Virginia, but I’d had enough of the political grind and wanted to plunge into international development instead. I was accepted into the Peace Corps and sent to the Central African nation of Cameroon as a Health and Water Sanitation volunteer.

I think about Cameroon often. Last fall was the ten-year anniversary of my return to the States, and I wrote a little about it then, but I wanted to talk a bit more about the Peace Corps in particular, and how it’s changed my perspective.

Continue reading “Cameroon”

What little companies don’t get about big ones

I frequently see discussion about/advice for startups about dealing with big companies (“BigCos”). Hunter Walk at Homebrew has this great, widely-shared piece on how startups can avoid wasting their time with big companies, and Steven Sinofsky has tips on competing with BigCo (and he would know). This is all very smart advice, but the way “BigCo” is often presented also struck me as somewhat unfamiliar, especially in that idiosyncratically Silly Valley way.

I’ve spent most of my tech career at big companies, not at startups, and I think a lot of startupland lacks an appreciation for the “BigCo” perspective on things. This is unfortunate, since many of those startups aspire to either (1) get bought by one of the BigCos they spend so much time complaining about, or (2) become a BigCo themselves. So here’s a few things I wish they understood.

Continue reading “What little companies don’t get about big ones”


Short one today. This is just about some tools I use for thinking.

The world is a complicated place and constantly presents us with problems that often contain many more layers of complexity than appear on the surface. This has been the human condition since we crawled out of the trees and stuck our heads above the grass on the Serengeti. Yet in the modern age, our lives – our communication, identities and especially livelihoods – are increasingly based on abstract constructions, rather than tangibles. We live in an age of symbols, and symbol manipulation, that require forms of abstract reasoning to really understand competently.

The problem? Abstract reasoning is hard, and it’s not really taught at all. The closest I ever got to it in my schooling was in philosophy classes (which, although ultimately valuable, were also mind-numbingly boring) and, more practically, on the college debate circuit, where it’s weaponized for advantage. Around that time, I realized that I tended to fall back on a list of certain heuristics – basic frameworks for conceptualizing an issue or problem – to understand and communicate about the facts around me. These heuristics aren’t always suited to every situation, but they tend to reveal much more truth than they conceal.

Continue reading “Heuristics”

The year in review

2017 has been a big year here. It was our first full year in New York. We got a lot accomplished. While the year has been filled with a lot of negativity for our country/world as a whole, it’s actually been pretty decent on a personal level.

Lots of people have different strategies for setting, making plans and achieving their goals. I tend to settle on very specific personal goals and then not talk about them much. This year, I managed to hit most (but not all) of the goals I set.

Continue reading “The year in review”

What people really want

The controversy-du-jour roiling tech this week has been, if you can believe it, how extremely wealthy Silicon Valley tech investors (virtually all white men) feel oppressed. Lots of these guys have been complaining of “censorship” of late, evidently not knowing or caring why that term doesn’t really apply to their situation; but then Sam Altman unburdened himself of his own hurt feelings in a cringe-worthy post in which he explained, evidently without irony, how much freer he felt in the less “restricted” environment of… Beijing.

I don’t mean to dunk on Altman, or the other (wealthy, white) dudes in tech who I’ve heard complain about not being “free” to say whatever they want without consequence. I would only refer them to xkcd, which has, per usual, the most succinct clarification of this issue around, as well as Anil Dash’s excellent rebuttal.

Rather, it’s more interesting to examine the growing popular ennui with the tech-utopian-visionary schtick that I, too, have noticed. It does seem that people are less in thrall to the “crazy, audacious dreaming” thing of late, and are increasingly likely – in the tech press, twitter and elsewhere – to encounter it with frustrated exasperation. I’ve begun doing this more, too.

Continue reading “What people really want”

Learn to sell

From time to time, I get asked for career advice. Sometimes it’s folks looking to get into product management, and others just curious about working in technology generally. I’ve thought a lot about what type of advice I can give that would actually be useful.

A big problem with an awful lot of career advice you hear, particularly in tech circles, is that it’s hopelessly tainted by survivorship bias. Almost all life/career advice from famous rich people is usually useless for this very reason. Beyond that, it seems like the most popular advice you see is “learn to code.” I think this is a mistake, and not very useful for most people. Learning to write code and develop web applications has definitely been a positive in my life, but it’s probably only been marginally advantageous career-wise. I’d certainly encourage anyone to learn, but mostly for personal enrichment, not career advancement.

Instead, here’s my pitch: go do a stint in Sales. If I were early in my career and looking to boost my long-term trajectory, I think is where I would try to start. Even in mid-career, where I am now, it’s something I think about often. More tech professionals should consider it. Hear me out.

Continue reading “Learn to sell”

Paying for the Class of 2039

When we found out that Penny was on the way, among the first things I did as a soon-to-be dad was open a 529 college savings account.* I don’t know much, but I know that 18+ years is a lot of time for compounding to do its magic, and that sending her to college is not going to be cheap. We are determined for Penny to graduate in the Class of 2039 debt-free, as both Laura and I were able to do. I now pitch a few hundred dollars into her 529 every month.

Planning for something as far-out as college in 18 years obviously involves a ton of unknowns, like: will people even go to college as a matter of course then? My guess is that they will, so we have to plan for it, but I have my doubts. American higher education is in deep trouble and on a path whose costs alone are clearly unsustainable. (And as we know, the thing about unsustainable things is that, eventually, they always stop.) As a future buyer of educational services for our (nearly) 3-month-old, I don’t know that I’ll be on the universities’ side when the time comes to save them.

Continue reading “Paying for the Class of 2039”

Why SaaS will stay independent

A while back, the estimable Villi Iltchev published this outstanding piece on “Why SaaS consolidation is not happening.” It’s almost a year and a half old now, but has held up wonderfully. Villi points out a bunch of reasons why the SaaS market has not followed the same M&A path that on-premise software did in the 2000-2008-ish tech cycle, with a special emphasis on the importance of Customer Success in enterprise SaaS. I have some thoughts on enterprise SaaS that take it a step further, but as we close out 2017, his basic point has been proven correct. The Great SaaS Consolidation that many VCs were gambling on isn’t coming. Instead, we have something even better: a broad, burgeoning landscape of SaaS businesses whose need for outside investment is diminishing, whose customer bases are diversified, and whose destinies are bright as growing, independent companies.

Continue reading “Why SaaS will stay independent”

News on our book

There’s news on the book!

Refresher: a few months ago, O’Reilly asked to publish the book that Ben Gaines and I co-wrote this year on product management in enterprise software. We’ve been in editing cycles since then, getting feedback and some really awesome reviews from some big names. I’m super excited for y’all to see the final product.

Based on the feedback we received, we’ve decided to change the name – Make It So is no more. Our new title is Building for Business: Product Management in Enterprise Software. While I loved the Trek reference, I have to concede that it’s a little niche. “Building for Business” is catchier, I think (I mean, for product management – let’s not get carried away), and more germane.

You can learn all about the book at the (new) website: The old site will now redirect there, too. At the site, you can also read a sample chapter and get a heads-up when the book is released. Signups, I’m happy to say, have been brisk.

The book is also now up on O’Reilly’s website, though not available for preorders yet. I’m told that pre-orders will be available prior to publication. Go check it out!