An Enterprise Primer

So perhaps you’re burned out in the consumer software game, or are just considering a pivot into the enterprise (“B2B”) market. You’ve heard that there’s a lot of opportunity in “selling to enterprises” – and maybe, you’re thinking, after you build some revenue there and make your investors happy, you can get back to the other world-changing stuff that you really want to build. Plus – most enterprise software kind of sucks, right? Users who have grown up with Facebook and Instagram are demanding way better experiences from the software they use at work, and you see an opportunity to serve those needs. So enterprise it is.

This is sort of a cardboard stereotype of a certain approach to enterprise software that I’ve seen voiced frequently – often by very smart, experienced people whose careers have mostly been in consumer-facing software. Well – it’s a very good strategy for failure. As a corrective, I offer this quick primer to some of the basics of how enterprise software is different. (I avoid the terms “B2C” and “B2B” as too jargon-y for my taste.)

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Tech is organizing

The prospect of labor organizing has long lived on the outer fringe of the technology industry. It’s long been assumed that highly skilled technology workers, particularly those in the most spectacularly successful Silicon Valley firms, were too spoiled with the industry’s famously lavish perks and compensation to ever consider forming unions. While that may still be mostly true, recent events make me wonder if a new moment is at hand. Spurred by ethical concerns over assisting the Trump administration, workers at Google recently forced a major change corporate policy, and others – publicly, at Microsoft and Amazon – are taking notice. Something new is definitely happening.

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This Meeting Should’ve Been An Email

Many of us today have jobs that are difficult to explain to our Boomer parents. Product Managers famously have this problem, but so do many flavors of knowledge workers: try explaining to someone who retired twenty years ago what a “social sentiment analyst” or “devops engineer” is. Advances in technology and changes in markets force evolution of job roles and responsibilities, as they always have and always will.

Yet something I find remarkable is how slowly change comes to how we work. I’ve been working in offices of various types for a while now, and can tell you that my office of 2018 is not that terribly different from one in 2003. The phones are all different, but meetings, interviews and most of the modes of working haven’t really changed. When I ask friends in other fields about this, I hear a lot of the same. Older people often point to the types of differences you’d expect – many fields have a somewhat more casual dress code today, workplace conduct is a little more decent, the women aren’t all secretaries. But what you mostly hear is just that things have sped up, or that capital is allocated more efficiently. (The shareholders have won.) But I think someone from your average 1980s office job could pretty quickly figure out one in 2018, at least once they figured out how to use the computer.

Maybe it’s not a lack of the right “work products” that’s holding us back. Maybe it’s us.

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Star Trek: Frontier

Fair warning – this post is going deep into Geek territory. If you’re not into Star Trek, you can probably safely skip this. This is a re-edit of a piece I wrote on Medium a few years ago. That said… here we go.

Late in 2017, the sixth major Star Trek TV series – Star Trek: Discovery – launched. And it was… fine. Like the rest of J.J. Abrams’ Trek storylines, it is set in the pre-TOS timeline. The way Viacom/CBS has pretty much abandoned “modern” Star Trek (that is, the entire post-TNG universe) has long baffled me. ST: Voyager wrapped up in 2001 and we had the “Nemesis” film in 2002, but since then, it’s just been the (relatively) short-lived “Enterprise” series and Abrams’ line of canon-immolating films set in the pre-Kirk era. In other words, almost as much time has passed since the last TNG-universe Trek content as between the end of TOS and the launch of ST:TNG (18 years).

This has always struck me as an awfully weird choice.

Like other millennials and Gen-Xers, I grew up on TNG, DS9 and Voyager. That’s canon. Enterprise, Discovery, and all the Abrams films just feel like retreading so much old ground, and I’m always irked by big plot departures they’re forced to take. (Let’s not discuss blowing up Vulcan.) In the last 16 years since Nemesis, there’s been nothing new built upon the post-TNG universe. So… here’s a pitch.

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Legend of the Plaid Dragon

I am not a software developer, but I like to code.

A couple years ago now, I was feeling handy enough with really basic Javascript to start looking for a coding project to really pull together a bunch of web dev skills and actually make something. I decided that I wanted to try cloning Legend of the Red Dragon, a text adventure game I played when I was a kid that is arguably the most successful BBS door game of all time. (All due props to Trade Wars.) After Ben and I finished the book last year and our family moved back to North Carolina, I picked up this project again and really make it into something.

tl;dr – I have a new Slack game available that you can try right now. Click here to learn more and, if you like, invite it to your workspace! The rest of this blog is all about how, and why, I built it.

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“Should I get an MBA”

One question I get from time to time is from people considering getting an MBA, and whether it’s worth the investment. I’m going to try to generalize my answer here so it’s applicable to folks from a variety of different backgrounds/career goals, even though I wound up in technology.

First, to show my cards: I have an MBA from Duke. (They want us to call it the “Fuqua School of Business,” but no one knows what that is, so I just say Duke.) I went through the traditional full-time program and graduated in 2011. I am still paying off the debt, which was considerable, even though I got a sizable tuition discount. What I wound up doing after B-school (tech) is completely different than what I went in expecting to do (international development). I’ll speak to my personal experience later on.

The modern MBA was mostly designed to serve traditional, defined career tracks into management consulting and finance. If you want to do one of those things, then going to B-school is basically a foregone conclusion and you can stop reading here. If not, then I hope the rest of this post can offer you some value in weighing this big decision.

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In Defense of Email

One of the “first world problems” that I seem to hear most often, but understand the least, is people who complain about email: getting too much of it, how it’s a waste of time, interpreting it, the list of complaints goes on. Usually, the people making this argument are selling something (like, say, an enterprise chat solution) or relying on email for something it’s not as useful for (like a substitution for a verbal discussion). So allow me make the counterargument: email is great. Email was literally the first thing humans used networked computers for and it is the ur-example of how open standards truly power the internet.

Unfortunately, this is also why I am increasingly dubious about the centralization of global email platforms, particularly Gmail, which threaten this model for how email works.

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The History of the Future

You cannot separate “history” from how history is done. This makes intuitive sense to anyone who thinks about it, but is easy to forget when you think of “history” as something that’s already known, as opposed to a field where there is lots of new research, discoveries, and re-interpretations of all manner of things that everyone thought they already knew. The methodologies used to do historical research have a direct impact on what we are able to draw from that research. This has me thinking a lot about how “doing history” in the future is going to be dramatically different than it is today, with big implications for whose stories are preserved and understood.

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Top Talent and HQ2

A popular parlor game around the Raleigh/Durham area of late, like in many other cities, has been handicapping our region’s chances of being picked for Amazon’s HQ2. My guess is that we’re in the top 3 or 4 cities, but hey, who knows? There are lots of pro/con positions for Raleigh (which really means the whole Research Triangle region): ex. available office space plus plenty of room to expand and good housing inventory, but a paucity of public transport. It’s a fun exercise to go back and forth on.

Yet one factor looms above the others, and it’s a persistent source of insecurity by the not just the Raleigh/Durham metro, but dozens of others around the country: the local availability of “top talent.” Specifically, this criticism says that the region in question does not have access to a global pool of people who can run or lead a major corporation. Since people run companies, not being able to tap that pool is a kiss of death. Fin.

The genius behind Thiel’s famous interview question, “what do you believe that no one else does?” is that it reveals where a person sees opportunity. It’s awfully hard to build something new and valuable if you only hold consensus views, after all. So here’s one of mine: 90% of consensus ideas about “talent,” including the one above, are utter nonsense. It’s both a self-serving criticism by Ascelaland devotees and implicitly relies on a whole theory of “talent” that is logically inconsistent and perpetuates a toxic and reductive view of what humans can do.

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