The Limits of Positive Returns

The last real album — at least by the standards I’ve given myself over the years, which are lower than Beyonce, but a lot higher than the average garage idiot — I’ve worked on came out five years ago, in 2014. That’s a really long time for me, but it’s not a coincidence that my daughter was born in early 2016, and my son in the middle of 2017. It’s not to say that I had kids and gave up on music, because I didn’t. My daughter even got to see me play on stage once! But, unsurprisingly, most of the time I’ve needed to be even a replacement-level parent has come from my favorite hobbies, which are writing/playing music and basketball.

Again, that’s pretty normal. But what’s interesting (and what I want to write about) is that there hasn’t been a linear relationship between the amount of free time I’ve had and the amount of production I get from my hobbies. Instead, there’s obviously some amount of critical mass involved, because with 30% as much time, I’m basically getting 5% of the output.

How I Used to Work

To have appropriate perspective, it’s important to realize that my music has historically come as a response to boredom. While I originally learned to play the saxophone as a kid because I actively enjoyed it, I didn’t really write or produce anything until I was a typical suburban teenager with long, directionless summer days and nights (and chemistry class). And even then, I didn’t start getting truly creative until college, when I had literally nothing to do on my weekends and would just drag a guitar and a cassette four-track to our music building and play and sing until my voice was gone.

I can’t understate the nature of how little I needed to be anywhere else during that process. Exactly zero people were ever looking for me, interested in at all in what I was doing with my time, or curious if I was being productive with it. Many times I would strike out, recording hundreds of awful, unusable, embarrassing demo ideas I never played for anybody or ever listened to again, and that never mattered. It certainly had no impact on my willingness or ability to continue plugging away the following weekend, or the weekend after that. In the aggregate, I don’t remember all the terrible things I made that didn’t work — I remember the overall process that gave me the demos that turned into songs I loved that we later recorded in the studio. The ratio of good to bad output was and is irrelevant.

Once I was out of school (and not even writing for a band), this was still the way I worked. I had two small bouts of unemployment that totaled less than a year (maybe six months right out of school, and then another six when I first moved to Cleveland in ’06), and I used the time in the exact same way. Set up shop, start grinding, and stop when you can’t go anymore. I got similar results; mostly crap demos I’m embarrassed by, and a few things I love that my kids still listen to today and dance to in the living room. The process worked.

Time and Capital

In theory, I think venture capital is supposed to work the same way. You try to buy time to give the right people and ideas sufficient room to just keep going to work every day, knowing that a lot of things won’t pan out, but the great ideas that do will be worth the overall process. But I’ve been dealing with venture capital for basically a decade now, and I don’t really think this is what happens at all. Sure, a couple big names keep getting absurd amounts of money pumped into them that allow a seemingly endless timeline of exploration — but that’s not actually what’s happening at those companies. They’re actually on a really tight, short-term timeline; it’s just about raising more money or keeping investors happy with what’s going on.

So that brings me to my critical mass problem with music. Like a VC backed startup, certain scenarios open up where I have time and freedom — for instance, I have an hour and a half or so this morning, because my wife and kids went to church. Therefore, why would I not go create an hour and a half of music?

Two reasons:

  1. Sometimes (most times?), an hour and a half of musical production effort results in… no measurable results at all (this is also true of writing, which is why everything on this site is disjointed and poorly edited now). As has always been the case, many times I just walk away with something I don’t really like and found frustrating to make. Compare that to an hour and a half of cleaning up the house, or getting ahead of stuff for work, where I always get demonstrable results and someone important is always happy. It’s tough to make that tradeoff when time is limited anyways.
  2. More importantly, the output of knowing you have an hour and a half to make something is usually something with scope and ambition of something you know you have to finish in 90 minutes. Those songs are very straightforward, unambitious, and often a little sterile. Verse, chorus, verse, bridge, chorus — crap, is that the van door? I gotta go, export, done. You can try to save it until next week, but I’ve always found songwriting to be very momentum driven. After seven days, the moment you were capturing is often long gone.

The Hour & a Half Business Plan

You’re seeing the startup equivalent of the hour and a half time investment throughout technology these days, and it’s more obvious than ever. Money is available to enterprise software startups that can run the exact same playbook that’s worked a million times, with the same bunch of founders with the same set of experiences and connections. Those startups are expected to hit certain growth patterns based on the success of other enterprise software startups, move up/down market, blah blah blah, rinse, repeat, and either IPO or be sold.

There’s nothing wrong with that, of course. I’ve worked for multiple companies like this who took this path because it made the most sense for the problem they were addressing. But you’ve got to admit that what I’m talking about is a pretty limited problem set.

Every time I have this discussion with either investors or people who spend a lot of time trying to win investors over, I get the same response, which is an immediate pivot to the financial justification for everything — as if I’m not aware of that after ten years of decks and quarterly reviews. But my point isn’t that VCs should start making unrealistic, borderline philanthropic investment strategies — it’s that the effective branding of VCs, the Valley, and “tech” as an industry (versus a concept that slowly moves along, well, everything) as this massive agent of useful social change has actually caused some of us to believe it, and just assume that cloud software for banks, or a variety of narrow systems designed to convert layer after layer of labor into disposable contractors are somehow the appropriate next stages of social evolution. All because they fit a desired exit timeline for today’s VC approach to investment strategy!

Let me say it more plainly.

  1. Capital is time to operate.
  2. Capital only comes from so many places.
  3. Bank loans are too small and too hard to get for most potential solutions/businesses/ideas.
  4. Internal investment at large companies is minimal and often constrained by various innovator’s dilemmas and the general inability of successful companies to grow and spread change and new ideas.
  5. VC money — and this is directly contrary to its carefully cultivated brand — is much too constrained in ambition, timeline, and willingness not for risk, but for actual loss to solve problems that actually matter at this point.
  6. Inherited wealth (as with business capital) mostly goes to people who don’t want things to change (because they are wealthy with things the way they are), or who are idiots and/or unmotivated.

So… what’s left? How did America come up with so many amazing innovations and honest-to-God progress through so much of the 20th century? It’s almost like we had a vehicle for broad, loosely managed but highly directional investment in things that, unlike VCs or banks, didn’t need to worry about capital returns.

Okay fine, have a hint.

Three Years, Five Months, Sixteen Days

Well, it’s been a while now, but after a very exciting and very educational adventure (in three offices!), I’ve decided to leave FiscalNote and figure out what’s next. Even though it was less than four years ago, I shudder to think at how different myself and my life were when I walked through the door back in 2015. There are plenty of cutesy current event examples, but the biggest two are that I now have not just one, but two kids, and that I live in New Jersey, just across the river from Manhattan.

These specifics were not… well, let’s just say “entirely expected”. Yeah, I was going to have kids, but nobody’s really ready for that that means, and we may not have totally planned on two in three years. Yeah, I knew my wife’s job might change, but I didn’t expect that I’d have to move to Maryland for her next adventure, or to New York less than a year later when that adventure was acquired by an enormous, exciting company you may have heard of that… helps you find what you’re looking for… on the internet. Yeah.

And while I’m loathe to give any generic advice to “the young people” given that we all come from very different backgrounds with very different resources, anchors, etc. — but if there’s one thing I think is universally true these days, it’s that if you do get a shot at something crazy, with a manageable level of risk, you better take it. I never in a million years thought I’d live in New York — seriously, never. And with kids? Utterly unthinkable.

But here we are. FiscalNote has been very cool about letting me work remotely for the last month or so, sometimes from home, and sometimes from our NYC office, but it only took me a couple weeks to realize that my life and my career were at an inflection point. Nothing crazy, no midlife crisis (that’s coming, I’m sure); just a series of events that have lined up somewhat coincidentally, but that together paint a pretty clear picture it’s time for me to figure out what’s next.

If you’re unaware, FiscalNote has gone through some truly insane growth since I started. After our acquisition of CQ Roll Call (which includes two publications I read voraciously long ago as a 20-year-old media intern roaming the halls of the Senate office buildings), we’ve become an eighty million dollar company with close to 400 employees. Lots of people have come and gone over the last couple of years — these were peak startup years — but this is different. FiscalNote is truly realizing what it’s going to be for the next, I dunno, ten or twenty years right now, and having done my small part to get us to this point, and then through the early parts of integrating two very similar yet very different companies, there’s a real feeling my job is just sort of… done. And while it’s true that I could probably abuse my long-term status a bit and become a living example of the Peter Principle, I’m fortunate enough to have some options, leave on my own terms, and maybe even breathe for a couple weeks before I dive into another job.

I’ve had a lot of cool adventures so far in the fifteen years since I entered the non-hourly workforce. But hands down, FiscalNote has been the craziest, most challenging, and most rewarding. In my twenties, I spent a lot of time working on other’s people’s projects and developing a lot of theories about how things — people, markets, co-workers, etc. — worked. FiscalNote, whether they originally planned on it or not, gave me a chance to really put those theories out into the world and watch them sink or swim. Sometimes I was right, and dammit, did that feel good. Sometimes I was wrong, and boy did I ever have some sleepless nights figuring out how to make things right (or less wrong). I hired people, I named things, I unveiled plans, I listened to people literally cry and argued with hundreds of people about hundreds of things. I even had to fire people, which was every bit as awful as people had warned me about.

The whole time, FiscalNote supported me in numerous ways. They let me go on two paternity leaves — 4 months for Mary, and 2 for Sam — that will matter forever because they fundamentally changed my marriage and my relationship with my kids for the better. They rolled me out with a microphone to sell the company on some of my biggest ideas because it was my job to have ideas like that and they liked what they heard. And they pushed back — oh Lord did they ever push back — when I needed criticism, and holes poked in grand plans, and just the occasional kick in the teeth to make sure I still cared. And I always did; maybe even a little too much at times.

Anyways, the reasons I’m leaving are simple.

  1. It’s pretty apparent I can’t do my job from NYC. I manage too many people, management for me is really personal and requires a ton of trust, and I can’t do 100% of it over a Google Hangout. I tried, and I just can’t. Not to my standards, at least.
  2. I could do a different job, perhaps, at FiscalNote — but that’s fraught with “change management” challenges, as captains of industry like myself like to say. There’s a point for every person at every organization where there are diminishing returns on time served, and experience shifts to baggage. I really hope I’m not there yet, but I bet it’s close, and I want to get out while I’m a net positive. I don’t want to be Patrick Ewing on the Sonics, for God’s sake.
  3. I live in NYC (okay, Jersey, but you know what I mean) — something I still can’t entirely get over and haven’t fully processed, and that means I’m a 36 year old tech person surrounded by an unthinkable buffet of professional options. Again, if opportunity strikes… you gotta go get it. You just have to, and then you pay it forward as much as possible. Short of starting a charity, I don’t know a better way to do good in this crazy, merciless, capitalist world we live in. So I’m going to find something good that I couldn’t do anywhere else, and see where that leads me.

It’s hard to overstate how much I learned and grew at FiscalNote — but since I stayed for a while (in startup terms), there actually aren’t that many people still around from the summer of 2015. That’s life in hyper-growth, I guess. Anyways, if you’re one of my colleagues and you’re reading this, thanks for the amazing three and half years and the opportunity to be a part of something special. I’m truly grateful and better for having gotten the chance to work with you.

Disagree and Commit to Replacing You With Someone More Fun

Here’s Business Insider on the latest trend from HR departments:

“Top tech companies are increasingly looking for people who, in the spirit of pushing the organization forward, know how to argue effectively. If you’re just going to nod your head and smile at every idea that comes your way, you’re probably not welcome.”

I am seeing this more and more from companies, but especially tech companies — when trouble strikes, they respond by shifting their hiring strategy. But while it’s not necessary a bad thing to think about (or even take some steps on), more than anything else it’s a dodge from the underlying challenge, and an unrealistic one at that.

See, it’s one thing to hire unethical people, people who steal, or callous, sociopathic people who step all over their colleagues. You never want those people, and you’ve almost certainly baked that fact into your hiring strategy already. More often than not, people who act like that simply… have a tendency to act like that, regardless of how incongruent it is from the overall environment. In their own perverse way, sociopaths and selfish people can thrive in healthy (but naive) cultures because there’s so much to take advantage of, just like fascism can thrive in a liberal (but naive) democracy.

Aversion to conflict is not like that. Here’s why.

Conflict is subjective

Selfishness is pretty straightforward. Most organizations don’t (and often can’t) design goals well enough so that employees can apply a laser-like focus to them without screwing over other people. That is not a real-world organization staffed by humans; it’s a fantasy that withers and dies once it leaves a PowerPoint presentation. Instead, every day lots of people make decisions to support other people on a very personal level, subsume a personal goal, or adjust a complicated plan to help give someone else a better chance to hit their goal, or just get through a bad spot. If you can’t recall ever doing this, you likely either work at a massive organization where nothing matters, or people probably kind of hate working with you, whether they admit it or not.

Good working relationships — real, human ones, not something you can proscribe via company values or an employee handbook — involve two or more smart people having sufficient empathy for each other to find a good balance here. What if I can save a couple thousand dollars off my budget by terminating a money-losing partnership set up by a former employee, but it will be accounted as churn during my account management colleague’s roughest quarter for retention (even though it’s not actual revenue churn)? By letting this slide for another quarter, am I being conflict averse or supporting my teammates? By drawing the line and demanding every resource our plan entitles me to, am I laser-focused on my goals and performance, or an unhelpful, cultural cancer?

It’s not an obvious answer, and if you think it is, you are probably either (a) kind of a sociopath, or (b) in a position where you face relatively little personal risk over business outcomes. In fact, let’s talk about that.

Aversion to conflict is often not a trait, but a choice

One of the more interesting concepts related to professional development and communication styles I’ve learned over the years is the idea of “adapted workplace style”. Basically, it’s the idea that everybody has their own personality, and obviously all or a lot of that impacts the way they work with others. But it’s not quite that simple — those of us with some amount of awareness and self-control often adapt aspects of our personality we either know or anticipate will be problematic in our working environment, which is why we act differently at work than we do at home.

For instance, as my very best friends (and a few acquaintances who have been in the wrong place at the wrong time) can tell you, my natural state when there’s nothing important to be done is essentially “lazy, cynical, self-righteous pain-in-the-ass”. I know this, because I was born this way, and my parents, teachers, friends, wife, cat, etc. have helped me understand the difference between when it’s amusing and lovable, and when it’s unhelpful and frustrating. This process is called “growing up”.

For me, though, one result is that I have a significantly adapted workplace style (I’ve actually taken some tests that made this same observation about me) that heavily leans into the things I have a natural tendency to ignore. While I still sound like me, and think like me, and have the same professional talents and gaps you’d expect me to have if you knew me, I make a concerted effort to focus on being the very opposite of lazy, cynical, and self-righteous. Sometimes, when I get to know people really well, those folks will see more elements of my non-work personality. It’s usually fine — again, these are almost always people who have grown to trust me and feel comfortable calling me out or lovingly telling me to shut up — but it’s always surprising to people who strictly know me as a reliable, collaborative partner at work, even if we’re just cracking jokes at a bar after work.

The point of all this is that of all the different unicorn qualities people try to hire for (“scrappiness”, emotional intelligence, entrepreneurial-mindset, etc.), the tendency for people to stand up for what they think is the right decision is one of the most adaptable things that exists. When you combine that with the fact that most people have jobs because they need money and careers to live and grow (duh), the end result is that “how much someone speaks their mind” is an incredibly fungible factor. People adapt, and they definitely adapt to the kinds of things that hurt their well-beings. How a company handles their opinion is one of those things.

That’s another decent segue, so let’s do it.

The culture and meaning of conflict is most heavily influenced by today’s organization, not new hires

Let’s tie this all together. You’ve got a highly sensitive, highly subjective concept — conflict — the definition of which self-aware, emotionally healthy people are especially good at adapting to, and you’re going to offer those people a great career so long as they learn to successfully navigate that definition to your liking. If they fail to interpret that properly, you’re going to sadly write them off as the wrong kind of person for the job.

Given that, what’s more likely — that new employees will dictate how your company defines healthy conflict, or that your existing company habits and leaders will (directly or not) dictate how strongly those employees stand up for what they believe in? Hilariously enough, the only people who safe bets to not regress to the mean of your existing culture of conflict-aversion are the sociopathic type-As you already know you don’t want. Conflict doesn’t bother them at all, and they’ll be sure to create it every single time it benefits them, regardless of what kind it is, or whether it’s good the organization as a whole. I really only see a couple ways out of this.

One is a world that requires perfect architecture — where people are basically independent, self-interested achievement bots, and we need a flawless algorithm (a.k.a., OKRs/goals) to keep them from inevitably eating each other alive.

The other is a world with what fees like an impossibly flawless working culture. On one hand, self-aware leadership purged of storied entrepreneurial vices like stubbornness, tunnel-vision, quick-tempers, and misdirected passion. On the other, front-line workers and middle management who constantly operate entirely in good faith, with zero fear of bad consequences for doing their best and speaking their mind, despite visible, daily reminders that those consequences are bigger than ever for themselves, their careers, and their families.

Which world are you betting on? I honestly don’t know which feels more plausible.

Nobody said this would be easy

I want to end this on a positive note, but I’m not sure I can. Given the subject (candor!), I’m not sure I should. After all, everywhere I’ve ever been, people have begged for me to be as real and as honest as possible (especially once they’re confident I’m a decent human being who cares about the well-being of the people around me)… until they don’t. And almost everyone (except a few truly exceptional co-workers I can probably count on one hand) has hit that point, where generic conflict turns into “a subject I’m very sensitive about” and the rules change, and change fast. A point where someone’s honest, thoughtful, nerve-wracking assessment becomes proof that they “just don’t get it”, are a “poor culture fit”, or “can be difficult to work with”.

We’ve had that conversation with so many of you, so many times, with the same productive, agreeable look on our faces, with “Radical Candor” on the bookshelf behind you, as you cut us off quicker and quicker while the argument escalates, and we silently, carefully recalibrate our approach to the subject, and in some cases, to you in general. And how do our leading organizations respond to this obvious problem?

“We need to hire people who aren’t afraid of conflict!”

Good luck, Corporate America.

Values & Outcomes

Playing in bands is probably the number one way I’ve spent my non-work time over the course of my adult life. This has been very much a recreational exercise for the most part — but in 2002, when I was twenty years old, I was in the weird position of being in a band that was more popular than it was supposed to be. In the process, I learned a couple of things that are still useful today in non-band contexts.

The background isn’t that important, but it’ll give proper context to the stakes at the time. My friends and I started a band in high school for a lot of the typical “let’s start a band in high school” reasons, with a few outside the norm-characteristics that made things interesting. For me, it was that I legitimately loved making things (even if I didn’t realize it when we started) and that songs and albums and related projects like that were a particularly good format for me. For us as a whole, it was that we were weirdly professional about concepts we’d later learn were actually business concepts; things like brand identity, quality assurance, and customer service. We weren’t necessarily good at these concepts when we were kids, but we did care about them even when there really wasn’t any money involved.

One result of this was that as kids, the people who seemed to really “get us” the most were older people — college students, adults in other (much better) bands, promoters, etc., who naturally had more respect for these business concepts than the other goofy kids we went to high school with. We were also better students than musicians, so most of the people who appreciated our more obtuse lyrics or gimmicks tended to be older and more, for lack of a less condescending term, literary. It was a weird brand, but it was ours, and it wasn’t hard to maintain because it fit the bag of dorks we naturally were.

Then we graduated from high school, recorded our first real studio album, and went our separate ways to college in different states. End of story.

… except it wasn’t. We didn’t want to stop playing music, and by that point we had achieved enough technical competence to make music that a growing number of people might actually listen to voluntarily. So we wrote more songs, practiced in our dorm rooms, and got right back at it when we got home. We booked more shows, made more merchandise, and recorded new albums.

So here’s where it gets atypical. When we started, our market was essentially our high school of 800 kids, plus a few groups from nearby towns, and the occasional scene person who caught us at a club and found us amusing. By 2002, the summer of my sophomore year of college, things were very different. Our core market had collapsed — we had been out of high school for two years had put essentially almost no effort into growing any kind of audience at our respective colleges. However, thanks to the internet, mail-order, some magazine reviews, and a small but not insignificant performance history out of state (and even out of region), that secondary market started to achieve a kind of proto-critical mass. By then, the average Glenn’s Army fan wasn’t someone who had gone to high school with us. It was someone who didn’t even know us personally, and that was something very different.

the fans you want and the fans you have

I always think to a conversation I had before a show with our guitarist (and more importantly, one of my best friends). This was more than fifteen years ago, so I’m paraphrasing most of this and probably getting the rest wrong, but bear with me because I think it’s an interesting thought exercise regardless of how bad I’m mangling the specifics.

When we were in high school, hometown shows (be they somewhere like the VFW, or a massive fire hazard in somebody’s basement) were always the most fun, because you could get tons of people to go, and a lot of them would be your friends. We did fewer and fewer of those as we got better, which was probably a good decision and had a lot to do with building an actual fan base. But we did book one that summer, and I remember being excited for our high school friends to hopefully turn out and help us relive simpler days.

A lot of people came — a lot more than I expected, given how much harder it is to promote that sort of thing without the built-in, captive market of our high school. But it wasn’t our old friends pulling up in station wagons and lining the walls of the old, wood-paneled portuguese-american club. It was… a bunch of kids. Kids too young to have gone to high school with us — some of them weren’t even in high school yet, and had their parents waiting in the parking lot. Some of the parents came in and sat in the back. And yes, some college aged kids from around the area who had seen us a few years back. But in general, we were above the median age of the room, and it definitely felt different.

Anyways, we talked about this weird culture shift both before and after the show, and we had two very takes on the situation. I was actually kind of thrilled; I wanted to expand our audience to the point where we might actually be able to play music professionally, and since we were nowhere near talented enough for some label to “make us famous”, that depended entirely on our ability to build our own following. Our fans getting younger seemed like an incredible sign of sustainable traction; we were like the opposite of U2, and incredibly, we were doing it simply by being ourselves and not pandering to anyone. We hadn’t changed at all, but our audience had somehow become more viable right when we needed them to.

That was not how our guitarist felt. He told me there was a certain kind of fan he wanted our band to have — basically older, smarter, wiser, with some historical understanding of what they were listening to and an appreciation of our influences. In other words, the kind of person who we had the most success with when we first got started. Success to him would be making this entire demographic aware of us, not impressing a bunch of kids (and somewhat uncomfortably for three 20 year old dudes, a lot of teenage girls) because we had loud amplifiers and driver’s licenses. If that’s who we were attracting, it was either time to fold up our tent, or figure out what we were doing wrong.

We didn’t play too many more shows after that, but the thing I’ve realized as time has passed is that there’s no right way to think about this sort of thing when you’re working on a passion project that’s an extension of yourself. If you want your music to be heard by a certain type of person, and that’s your primary goal, you shouldn’t be satisfied playing to people who are nothing like that, even if those people love you and there are a lot of them. Our band wasn’t a job, even if I hoped it could be some day. But either way, I realized I had an operating difference with, in startup parlance, my “co-founders”. I was content working from our values out and going with what happened, while they were more concerned about the outcome.

startups are like bands, pt. 17

High school/college bands and venture-backed startups have a lot of challenges in common, and the more I think about it, the more I think it’s because both tend to start in environments where their existential costs are subsidized (and thus hidden) for a while. Kids in bands don’t need to make money to keep having a band (or to eat); money they do make simply validates their effort and often gets reinvested into growth efforts. I know this because in the kinds of bands I’ve been in as an adult, getting paid sometimes seems so ridiculous that we refuse to accept it, especially if we’re playing with someone on tour who’s actually trying to run some kind of sustainable business.

But when you’re a kid, the fact that you don’t have to think about the grind of operating allows you to think about the things you want to think about; creative freedom, artistic integrity, and a brand that has nothing to do with money. And as I mentioned a moment ago, there’s nothing wrong with that, so long as that’s the end goal you’re working to — not financial independence.

Startups are funny because they’re a little bit of both; often passion projects for founders and early hires, but definitely investments and outcome-oriented ventures for institutional investors and later-stage employees. I’ve now been in enough of these to see the inevitable clash of these two perspectives — where some people believe adherence to their values is the key to driving outcomes, and other people believe it only makes sense to derive those values from the desired outcomes. Unfortunately, in a business, there are operational realities that make that clash a lot more consequential, and a lot less avoidable.

good and bad outcomes

If you work at a stable, profitable business, some of this thinking is probably going to seem ridiculous, so let me clarify a few things. There are a couple different outcomes for startups that can be desired at different times.

  • additional investment (at an increased valuation)
  • acquisition by another company (at a desired valuation; good for people with equity, or anyone who likes the buyer, not so good if you don’t have sufficient equity and don’t like the buyer, or stand to lose your job)
  • profitability (almost always good, but bad if it’s lower than expected or reveals the limitations of your business model)
  • development or traction that makes one of the other three things more likely (always good unless you are running out of money quickly)

Different people in different startups will have different opinions on all of these outcomes, depending on their prior experience, personal connection to the business, and interest in the kind of work the company does. Right there, you’re introducing a lot of potential conflict — and that’s just between a bunch of different, positive outcomes. There are also negative outcomes with different meaning to different people. For instance, a down round (where you get additional investment with a lower valuation) is bad for equity owners, and probably bodes poorly for future investment, but it’s still additional investment. If you’re looking for resources or to avoid cutting jobs, that can be a good thing.

Anyways, the most complicated thing about all of this is that just how desirable these and other outcomes are is a constantly moving target. It changes over time, and even changes individually in the heads of individual people as their personal and professional goals change. For instance, two people can start a company with dreams of dominating an industry. But after five years of passionate work, one of those people may decide they’d prefer to build a niche competitor with a great work environment, while the other is still convinced the opportunity for a better financial outcome is there. What happens then?

what values are for

One way to preemptively settle these potential disagreements — which happen not just among founders, but hundreds or even thousands of people in a company — is to base your decisions on values instead of outcomes. If you truly believe in a set of values, they can inform your transactional and operational decisions in a way that prevents the desire for a certain outcome from clouding anyone’s judgment.

For a giant-sized, non-startup example that’s easy to wrap your head around, think about Apple. They have an almost unlimited set of ways to make money. How do they decide what to do, and what not to do? How do they sort out which things could create short term success at the expense of long term success? Which of those outcomes is more important?

While Apple, to my knowledge, doesn’t have some stone tablets with values written on them, the way they’ve operated for years and years now makes it clear that there are some fundamental values they stick to, various outcomes be damned. One (and again, this is just my interpretation) is that they don’t believe modern technology products are ever truly successful when produced as cheaply as possible. Sure, there’s a certain level of quality they will then aim to produce efficiently, but there’s always someone making a crappier, cheaper version of whatever Apple makes, and there always will be. Another is that they don’t outsource their design work to competitors or market trends. They’ll adapt, but only when they believe they’ve been proven wrong about something — big screen phones, for instance, versus touchscreen laptops. People have been screaming in huge numbers for Apple to do a bunch of different things forever, and Apple never listens, regardless of potential outcomes.

One of the ironies about values being so prevalent at venture backed startups is that new organizations are often the least equipped to decide what values they really want to follow, mostly because they’ve either never had to prioritize a value over an outcome, or at least an outcome they really, really wanted and realistically had a chance to achieve. That’s my test for the authenticity of a value — when have you had to turn down a realistic, desirable outcome in order to adhere to that value, and what did you choose instead? And to be clear, choosing not to screw over a customer because you don’t want other customers to find out isn’t about relying on values. That’s just trying to prevent an outcome you don’t want. Losing money (or time, or progress, or whatever) to not screwing over a customer when nobody will ever find out is a real test of your values.

It’s not just ethical questions, either. Have you ever held a product back that wasn’t good enough in the face of existential market pressure? If not, it’s crazy not to question your dedication to quality, because you’ve never actually stood up for it. Did you ever make a decision that your available data indicated was wrong? There’s nothing wrong with that — but again, I question your “value” of making data-driven decisions.

You don’t need a set of values to tell you to be a reasonable operator; to listen to data when it makes sense, meet customer needs when it’s good for business, or build products that are competitively differentiated from other products. That’s just running a business (or anything, really), and people have been doing that forever.

values are expensive

So look at my old band (those handsome devils) again. We had very, very strong values, and we had some desired outcomes. My main desired outcome was to do something that followed those values, and my secondary, disposable outcome was to be in a commercially sustainable band. I was really happy back in 2002 because it looked like both of the outcomes I wanted were possible, but if not, I was more than ready to throw away the secondary one. In a way, I did; one of my (unofficial, of course) values was to keep my best friends. When they didn’t want to support my desired outcome of being in a band for a living anymore, I gave up that goal, but didn’t give up (and still haven’t given up) those friends.

But I had that option, because I wasn’t a business. I didn’t have investors, or obligations to anyone at all. Venture backed startups often feel that same way, especially in the beginning, but at some point the bill always comes due, either because you run out of money, or become successful enough those investors and creditors want to see the dividends you promised so long ago. That inflection point is always hard, always confusing, and always surprisingly conflict ridden. Because the potential outcomes are suddenly very real, and very consequential, it’s the very hardest time to truly lean on values. It requires more faith than many people can reasonably have in something like that. Unfortunately, there’s a very simple, very tempting way to kick the can down the road and prevent this kind of intellectual and emotional reckoning — reverse engineering!

In business, that means you set up the values you feel good about, and the outcomes you want, and you set as a given that those outcomes will occur if those values are adhered to. In politics and policy, we call this ideology, and see it in the “no true Scotsman” fallacy, but it’s equally present in any organization with opinions and outcomes.

For instance, I could decide that my north star is quality control — that I won’t release any product into the market until it’s as rock solid as possible, and that I won’t make any operating decisions that runs the risk of putting products into that hands of customers that don’t work the way they expect. That seems like a good value I could get behind. But it’s entirely possible that some particular outcomes of adhering to that value is that I’m slower to market than my competitors, that I lack functionality customers want, that my product costs too much, and that I’m ultimately unable to grow into what I want my company to be. If I’m truly committed to that value, there’s no tough decision here; I’ll mitigate the costs of adhering to it the best I can, but I’m going to continue to prioritize my quality control above all else. If I fail, I fail. But I won’t fail because I didn’t stick to my value.

Staring down the barrel like that is really, really hard, but it does happen. Basecamp is a great example. So is Tesla, even though it seems more and more that the only core value Elon Musk is willing to go to the mat for is “I am smarter than everyone else”. In general, you’ll see it more often from privately or family-owned companies removed from the demands of stock price and valuation, like Rolex. Of course, there are also thousands of ventures you’ll never hear about, each with strong values they stuck to as they ran out of money and closed their doors.

values vs. delusion

As with many things I write about, I think the biggest takeaway from all of this is that lying to yourself about your motivations — especially in regards to values vs. outcomes — is a really good way to waste time and lose credibility. If your values are really a tiebreaker (“… we’ll use our values to decide what to do when everything else is going great!”), they simply aren’t very important, and you shouldn’t pretend they are.

Remember, people are adults, and we’ve all made — or will have to eventually make — some decisions in life driven by money and resources. If they didn’t, I wouldn’t even have a job! I’d be in a band.

The Era of Entrepreneurial Can-Kicking

I’ve seen Facebook’s recent mea-culpa television advertisement several times lately, which is actually pretty weird because I watch very little live TV. I guess it’s just on a lot.

The gist of the ad is basically this — Facebook was meant to be a cute wonderful thing for making people happy, and it did that, and everyone loved it, but then a bunch of people started using it to do terrible things, and now Facebook is going to “do more” to try to keep these terrible things from happening. Reasonable people can disagree, but I found the whole thing to be pretty weak tea, infused with a sufficiently on-brand blend of condescension and obliviousness.

One obvious, unanswered question involves what Facebook is actually going to do about this kind of stuff, other than “more”. But a better question is — why do all of these terrible things keep finding a home on a platform ostensibly designed to foster wonderful, magical personal relationships and connections?

The answer, of course, is that Facebook isn’t designed for that purpose at all. It’s designed to get people to stay on the platform specifically so they (a) look and click on as many advertisements as possible, and (b) provide the platform with data about themselves that allows Facebook to charge more money for ads that they see. That’s what the platform is designed for, because Facebook users have zero financial relevance to Facebook, Inc. outside of their ability to be monetized through advertisements.

This has come up a lot in the past, and not just about Facebook, but at this point society seems to have become bored with the lecture and is locking on either (a) Facebook unilaterally acting against the best interests of their primary revenue machine, or (b) the government making some of those best interests illegal and therefore forcing Facebook to either make less money or figure out another way to make it.

the original sin of consumer SaaS

If you were in the software startup space anytime during the last ten years or so, you probably heard a lot about the idea of “monetizing” a business, which basically means figure out something that people wanted to do online first, and figure out how to make money off supplying that thing later. This was a really tempting model for investors because it was obvious that so many industries were being re-positioned online (with new winners and losers), so the hope was basically to get in there first, establish yourself, and then sort out what to do with your market leadership later. If you had enough capital to work with, you could do this, at least for a while.

A couple of interesting models came up over time. Craigslist learned to make quite a bit of money by using technology to run more efficiently, and decouple a cash-cow service (classified ads) from a bunch of expensive, unrelated activities (journalism). A few services like Dropbox, etc., made freemium work by bolting expensive, must-have corporate features onto a nice consumer product people couldn’t resist bringing in to work. Amazon built an innovative technology stack to support a massive, break-even retail business, and then productized the technology stack. Apple kept things simple and just charged people for products and services.

In many cases, though, the clever business models fizzled out (or were never even conceived), and popular products fell back into one of two buckets — making money off of advertising, or selling their company to someone who knew how to make money off of advertising. Facebook, Google, and to a lesser extent well-capitalized weirdos like Pinterest build things for you to use, but ultimately live or die based on what advertisers are willing to pay them.

the problem with advertising

One of the odd things about a business with a purely advertising-driven revenue model is that as a measure of real value, it’s vague, amorphous bullshit. The Facebook user experience is good enough to… warrant usage, I guess? But we have no idea if it’s good enough for people to actual commit resources to, because they don’t have to. So Facebook gets to pretend they are above the idea of creating real, demonstrable consumer value (the kind measured in dollars), when the reality is that they have no idea how to create it and are simply kicking that necessary can down the road for someone else to figure out. If you create a product no one values enough to pay for, and then you cover it with advertisements, it’s true that you may be able to make a lot of money and a run a successful business. After all, Facebook sure has. But you still haven’t actually figured out how to make or do anything that people value enough to pay for — you’ve simply passed that responsibility on to other businesses who are supposed to do that, collect the money, and give you a cut for advertising the valuable-enough-to-pay-for thing. Gee, thanks.

And that’s the real key here. It’d be one thing if there was one weird little tech company inserting themselves into things to make a confusing buck or two. But that’s the standard — that’s the go-to playbook for so many things. The only thing stranger and vaguer than the value of something like Facebook to its users is the value of something like Instagram to its users, which didn’t even bother to put together an advertising model. It just sold to Facebook for two billion dollars once a lot of people were using it. So now Instagram kicks the can of generating demonstrable value to Facebook, who immediately says “noooope!” and kicks it right on by to advertisers.

Even worse, we’re talking about advertising, the very definition of a difficult-to-measure return on investment. The most critical business goal Facebook and Google have really accomplished is the wall of ad-tech and thought leadership that’s convinced marketers they actually know what they’re getting out of digital advertising, when in reality they don’t really know anything. Some business models work great; first-touch attribution to a Google or Facebook ad with properly functioning tracking (easier said than done) that leads to revenue conversion event, like a subscription, or buying a t-shirt or whatever. That’s a pretty clear path. Most paths aren’t like that at all; people are marketing top-of-funnel type activities that kind-of-sort-of lead to revenue, but are massively dirtied and complicated by the use of multiple channels, broken tracking, click fraud, robots, fake accounts, and everything else. Nothing represents the “well, I guess we have to” stupidity of digital marketing quite like companies bidding for the rights to their own name so they can pay Google every time somebody clicks on it.

I get especially riled up by online advertising because I have to deal with it, but the vague, “nibbling at the margins and pretending we’ve made a huge difference” tendency seems to be everywhere. Uber’s another great example — on the surface, it looks like we’ve broken up the taxi lobby, but really we’ve built a generally accessible private car service subsidized by billions in venture capital and lower wages for drivers. Uber isn’t actually any more efficient at all, at least not enough to justify the lower prices it needed (and still needs) to appeal to the market. Tesla has had two major impacts; one, it’s changed the way the media covers the car industry, and two, it’s provided at least some kind of unquantifiable kick in the butt to real car companies who can actually produce in quantity to advance their electric technology. But I don’t think that’s why investors shoveled billions and billions of dollars into it, and I certainly don’t see it as world-changing innovation.

what the hell is going on?

So why is this happening? My theory is this — we’re running into the capitalist equivalent of a communist problem. With a state controlled economy, eventually you run out of obvious, top-down economic investments that make sense for the state to make, especially when there’s only one source of ideas (the government). At that point, you get some combination of stagnation, duplication of effort, or outright corruption as the state struggles to find something — anything — it can do to make a difference and justify the fact that it controls the economy. I’m a child of the 1980s, and this was the narrative we all saw play out in the Soviet bloc. Gray, repressive state apparatus can’t do anything right, suddenly budding entrepreneurs start solving random, long-irritating social problems with a flood of small ideas.

The capitalist equivalent of this is upon us. Instead of the state controlling all the money, we’ve watched it bubble up to a small group of people who are trying to use it to generate additional growth without actually changing too much about the social order, because those people are on top of it. We need consumers to generate more business for our investments, but consumers don’t have any more money than they did ten years ago, so we have to use them as representations of revenue through vehicles like advertising, credit, and “engagement”. Until more money (a lot more money) gets to the masses, you’re not going to see revolutionary ideas; you’re going to see ideas like Elon Musk’s stupid Boring Company, where he — and I guess he’s serious about this — plans to dig special tunnels underground that will transport individual people in their cars and help them avoid traffic for a while. This is not a social improvement wrought by the power of markets; it’s a marginal improvement on the status quo that largely benefits rich guys in big cities with cool cars.

While I don’t blame venture capital for this, I do think VC money (and the high-expenditure runways it allows) can help mask that it’s happening. That may seem pretty rich coming from me, someone whose last three jobs have been at VC backed companies, but the businesses I’ve worked for have each charged real amounts of money for their product, and have had business models dependent on creating enough direct customer value that said customers will pay for it. We might fail, but at least we accept math.

I don’t know how this era ends, to be honest. Maybe radical economic shifts aren’t necessary and I’m just being uncreative — but I don’t think so. If so, until those happen, many of our greatest innovators are going to be stuck reallocating a shrinking pool of consumer money from one shell to the next, and hoping nobody calls them out on it before they figure out what do.

Debates vs. Discussions

While I wouldn’t say I “avoid” writing about politics on this site, it’s definitely true that I try to focus on other things. This is mostly because there’s already so much good political writing from so many interesting perspectives, and there’s not a ton of value I can add. It’s also because I care a lot about civics and political thinking, and went to school for it, so just spouting off without putting in sufficient time to read and analyze the things I’m reacting to seems unproductive.

Still, for a lot of different reasons (splits in popular culture, fewer mass-experiences, etc.) , our political culture seems increasingly influential at a time where it also seems like an increasingly bad influence. People have been pointing this out for literally years — see Jon Stewart’s famous Crossfire appearance more than a decade ago — but it seems like The Game Show Host President has really pushed things over the edge (or at least pushed these trends into the mainstream), and many of our worst political tendencies are finding their way into our daily interactions.

There are a lot of these tendencies I could cover here, but I’m going to focus on one in particular that has major potential impact on organizations outside of politics and policy — the conflating of debates and discussions.


Debates can be a lot of fun, because they’re a combination of two things Americans love — ideas, and winning. I’m not going to use real debate terminology here (because I don’t know what it is), but for the purposes of what I’m talking about, let’s define a debate thusly :

  • in a debate, each position is represented by an advocate
  • each advocate attempts to convincingly prove that they are absolutely correct, and that their opponent is absolutely incorrect, at least when it comes any conflicts with their own position
  • there is some third party (judges, an audience, voters, whatever) that is going to ultimately pick a winner and a loser (or losers)

When I was a little kid, a lot of adults I looked up to told me that I would enjoy formal debates, probably because I was constantly arguing with them in ways that were only somewhat compelling but extremely entertaining. I even participated in a debate once (just once) in high school and thought it was kind of cool. However, debates actually have extremely limited utility in real life, because many of the key properties of debates I listed above don’t exist in realistic scenarios.

For instance, in real life :

  • the best answer is often represented by no side at all, often because it hasn’t occurred to anyone yet
  • almost every position has flaws, and a lot of bad ideas have interesting elements in them that can be used to solve flaws in better overall positions
  • there is often no third party to validate a position, or the third party is unqualified to do so

There’s a perfectly valid place for pure debates. It’s when you’re down to a few fixed courses of action (often some kind of specific tactic), and a bunch of people have to agree on which one to commit to. Once everyone understands the options and agrees on what they actually are, it can be very constructive to have an advocate for each (it’s even better if they actually believe in the stance), and hash it out for the rest of the group. When my high school punk rock band started taking songwriting (somewhat) seriously, we had lots of useful debates on things. Did this song need a third chorus, or was it too repetitive? Good, honest debates don’t necessarily drive consensus, but at least they get people to a point where they agree on what they don’t agree on, and everyone gets to hear the best story for each option. This is much better than having to do something you don’t like, and don’t even properly understand.


A much more common form of arguing/advocating in the discussion, which is much less emotionally satisfying for competitive people, because you can’t really “win” no matter how clever or well-prepared you are. Discussions occur (again, I’m making all these definitions up, so bear with me) when a bunch of people have to figure out what the right thing to do is, but don’t have a finite list of options they are trying to choose between. People have opinions and biases for sure, but they are often ideological, or directional, and very few if any of them have gone all the way down the rabbit hole to determine an operational plan with costs, benefits, and impacts on everyone. The group is having a discussion to figure out how to solve a problem, and that problem is emphatically NOT “which of these several options should we take”. If you think it is, you’re preparing for a debate, and you’re going to have trouble contributing positively to a discussion.

In punk band terms, our discussions weren’t about making final decisions like our debates; (often choosing between two unpleasant options) they were about figuring out what our next options could actually be. When those discussions felt like debates, it was usually because one of us thought they knew what someone else was getting at, and didn’t like it. These were… not our most productive discussions.

In politics, there seem to be fewer and fewer visible discussions, and even the few we have are framed as “negotiations”, which in practice appears to be largely a debate between various red lines parties really, really don’t want to cross — but might, in the right scenario. Again, that’s not really a discussion.

too many debates, not enough discussions

As mentioned earlier, debates are an emotionally satisfying form of collaboration for people brought up on winning and demonstrable excellence. Unfortunately, they’re only truly useful in a small number of situations, so most of the debates I’m either forced to witness or — God forbid — take part in are pointless. The advocates are primarily there to win approval of a certain position, not explore options or the validity of their own position, so various tactics that improve the odds of winning while making the overall environment more confusing and less productive tend to creep into the room. Some common ones I roll my eyes at :

  • apples versus oranges — defining the definitions used in the discussion based on the debate you want to have, and then forcing every option into that framework (even if it makes no sense) because you’re ready to argue on that turf
  • not relevant — setting boundaries for the discussion that extend to fit around your position, but not necessarily other positions, so you can dismiss flaws to your position (or positives to another) as irrelevant to the current discussion
  • projection — telling other people what they think, so you can turn an actual person’s position into (at best) a proper debate partner, or (at worst) a straw man you’re excited to beat up with your preferred position
  • axe grinding / redirection — undercutting a useful path an open-ended discussion takes as it becomes apparent your pre-established position is not a viable solution to the newly identified challenge (“… BUT HER EMAILS!!!”)

Again, these unhelpful actions are not necessarily a result of someone having a bad idea or weak position; it’s a result of them insisting on having a certain position when the group simply isn’t ready for one yet. The fact that Ted Cruz loves formal debating (and is, from what I understand, extremely good at it) and the fact that everyone in the Senate from both parties actively resents him and wishes he would go away is probably not a total coincidence; he brings an insistence on debates to things that should be discussions, and it’s entirely possible that someone like Cruz is great with debates (which are rare in actual legislating) and terrible at discussions (which are a key component of legislating).

fight to protect the properties of a good discussion

Professionally, people have often mistaken my refusal to take a debate position on some workplace question as a lack of interest in the subject. This is usually wrong; most of the things I truly don’t care about don’t get brought to my desk, and when one of them is, my lack of interest is usually really obvious. For everything else, what I’m really trying to do is protect the integrity of a real, live discussion designed to fix the problem. If I immediately become an advocate for a particular solution, it’s possible — probable, even — that I will do so before I have sufficient understanding of the issue and its impact on everyone else at work. After all, we have entire teams dedicated to very different challenges than mine (engineering, product, sales, support, finance, etc.). How could that not be true?

When there’s a problem that affects everyone, and I’m tasked with solving it, I’m a strong believer that setting up the frame for a proper discussion with everyone is the most useful thing I can do. Often, in doing so, it’s useful to build a theoretical stance that would make sense in the framework I’m suggesting, and when that’s the case, I’ll do it. But — and this is really, really important — you can’t lose sight of the fact that your stance is secondary to that discussion framework. You absolutely have to be ready to throw your stance in the garbage if your open discussion reveals that your stance is not inherently dumb, but simply the wrong type of stance for the actual problem you’ve uncovered. This is something that I’ve had to work really hard to get better at over the last ten years or so, but it’s led to most of the best professional decisions I’ve helped organizations come to.

As Long As I’ve Got My Suit and Tie, I’m Going to Leave It Out On The Floor Tonight

I’ve never been very good at dressing up. My roots are in technical tinkering and the creative arts, with a healthy dose of New England punk rock (and think New Hampshire, not New York), so maintaining appearances was never interesting or natural to me. As a kid, I agonized over even basic, semi-formal requirements for things like school dances, performances, or graduations — never mind things like weddings.

This remained fine as I grew up, primarily because I went into tech instead of my other potential destination, journalism (or, God forbid, law). I interned as a clueless D.C. journalist in the fall of 2002 and enjoyed a lot of what I got to do, but still found myself jealous of the CSPAN cameramen who got to play with cooler equipment and dress like AV guys while I poked at the itchy collar on my shirt and my uncomfortable shoes. So when I started my career at a mid-stage Boston tech startup in 2004 and discovered that they cared a lot more about how fast I could format press releases and assuage customer concerns over the phone than whether I could tie a tie, I knew I had a path.

From then on, nothing brought me any closer to formalwear. Support, technical writing, product management, and eventually product marketing required me to be increasingly strategic, but not sartorially impressive, especially since I worked for bosses who understood my value and trusted my ideas and execution skills, but usually handled dealing with customers and company brass themselves.

As a result of all this, when I found myself running FiscalNote’s marketing team this fall, I suddenly found myself in the unexpected position of representing our company and our function at an executive level — even if somewhat by default. While in the past I had never felt any real internal pressure to figure out how to fit in with the suit and tie crowd, this seemed different. My company had given me a chance to step up into a role even I wouldn’t have thought myself capable of just a few years ago; why shouldn’t I at least try to meet those expectations on every possible front? Customer events, board meetings, etc. — these were important things I was being given an opportunity to attend, influence, and make as successful as possible.

Basically, while I still loved the idea of not wearing a suit (or anything other than Boston sports-franchise related t-shirt, to be honest), actively refusing to didn’t resonate with me the way it used to. That kind of line in the sand just didn’t feel like a part of my identity anymore, and I felt worse about the idea of letting my colleagues down (even just a little) than I did about wearing silly clothes.

Man, did that ever make me feel old.

this suit is black not

So I bought a suit. It wasn’t fancy, but it wasn’t cheap, either — the nice people at the nice store in the nice mall I usually don’t go to tailored it and told me it looked great and had me try on different jackets and stuff. My wife was very helpful, and didn’t laugh at me too much.

I went home, put on my suit, and went to work. Here’s what I learned about the dressed-up version of myself.

  • Clothes aren’t magic. Instead of feeling like a badass captain of industry, I felt self-conscious and stupid most of the day. Worst of all, I felt inauthentic, which I think is an even bigger hang-up for me than it is for most people.
  • I thought about my clothes a lot, which is not a great frame of mind to be in when you need to get work done. There are just a lot of things you can do wrong with formal clothes that people who wear them all the time naturally avoid, and I probably did them all several times.
  • Eating, drinking, sitting, leaning against things, bathroom breaks — pretty much everything is risky behavior when you’re walking around in what are basically pajamas made out of money, and that didn’t make me any more comfortable with my environment.
  • If you’re the kind of person who doesn’t wear formal clothing, and you’re suddenly thrust into an environment where everyone there is dressed up, there’s really no way to succeed when your goal is to fit in and not be a distraction. If you don’t dress up, you’ll make a scene. If you do, people will notice, and you’ll make a scene. (“Whoaaaa, look at this guy!!!”) Hopefully this gets better with time.
  • I’m pretty sure that my problem with most real-time interactions is my preference for honesty and candor. I’m certainly not rude, or inappropriate — I just have trouble naturally interacting with other folks with the right professional safeties on, so rather than say something stupid, I prefer not to say much at all. I don’t hate small talk so much as I’m actively bad at it. I’m not disinterested in you as a person, I’m disinterested in the stupid, safe topic we’re inexplicably discussing, but since many people are uncomfortable having honest conversations with people they’ve just met (myself included), that’s what we’re going to talk about.

In short, my trouble with suits doesn’t really have anything to do with work, or business — I’m actually pretty good at that stuff. The trouble I have is with many of our oldest, most irrational social traditions, and that’s been a problem that’s dogged me since I was a little kid. I literally just don’t understand ties, just like I literally don’t understand how to feign more interest in another person’s story than I actually have, or how to impress a girl in front of a keg in a frat house where I can barely hear what anyone is saying.

(That last one hasn’t been important in about 15 years, so at least I’m making progress.)

“That’s just how things work” has always been the exasperated response from my well-intentioned, more socially flexible friends and colleagues, and I’ve always grudgingly accepted it and never insisted or expected that anyone else think the way I do. The funny thing, though, is that when I am actually praised for my thinking, it’s almost always for clearly and accurately modeling a complex situation into something real and approachable. And yet many people are often surprised by the fact that this same person would struggle to integrate irrational, distracting bullshit into their natural behavior.

Suits and ties don’t make any more sense than skinny jeans, or those crazy things that make you have giant earlobes, or the safety pins on leather jackets kids at our shows used to wear. And while I understand that our society uses them to convey a complex series of social indicators (suits indicate business acumen and wisdom, or at least the possibility of wisdom, now hoodies sort of mean tech, etc., etc.), I’d be lying if I didn’t admit that I still think it’d be a lot more efficient if everyone was just honest with each other and evaluated what we all said and did on the merits.

The fact that I’m old and realistic enough at 35 to realize people aren’t going to do this doesn’t make it any less true, or any less the way my brain works. But I’d like to think being able to work around that is just another thing I’ve been able to improve about myself.

My Saw Man Argument (WOMP, WOMP)

One of the best parts of working at a relatively early stage — or at least growth stage — company is that there’s a general bias towards doing things quickly. This is great, because I’ve found that working with other people on just about anything tends to slow things down for a variety of reasons. More people means more opinions, more views to consolidate, and more fears about failure (both personal and organizational). In mature companies, this basically eliminates the ability to quickly try interesting things unless you set up some kind of specific environment to do so, which is why people like me tend to go crazy at mature companies, or just give up and read the internet too much. Fortunately for my career — and unfortunately for the message boards I used to spend time on in the mid-2000s — I haven’t worked at a mature company in about ten years. Instead, I’ve been working for businesses in the highly motivated “grow or die” stage, where standing still is the only thing you can really do wrong.

Of course, anyone can do lots of random things quickly — that doesn’t take skill, sound decision making, prioritization, or anything other than energy, really. And while doing that in an early stage environment gives you a lot of very satisfying dopamine hits, you also run the risk of generating — and living inside of — the illusion of progress. Yeah, you’re doing lots of stuff, but what’s really different than before? (Sorry, can’t take the time to answer that — have to do more stuff!!!) Marketing departments are often the worst at this kind of thing because they’re where a lot of companies turn for miracles, like unexpected press coverage, or some crazy stunt that suddenly changes undesirable business fundamentals. That dynamic is partially the fault of Marketing people who don’t like to be held accountable preferring to skip around from one crazy project to another, and partially the fault of everyone else for expecting white-elephant type events to overcome less exciting operational or strategic problems.

move fast and accomplish things

While I am abjectly terrible at construction and home improvement tasks, I do remember my Dad teaching me how to use a saw. When he first put a piece of wood into the vice in the basement and handed me his, I attacked the wood exactly as you’d expect a crazy seven-year old with borderline ADHD to. I wildly thrashed about, moving the saw as fast and as violently as possible in an attempt to cut it in half.

This is not a good way to cut wood. So my Dad taught me to slow down — just a little — and make decisive, high quality strokes with the saw. Keep it straight. Make sure the blade is really getting into the wood. Take five or six quality swings in a row to get a rhythm before you start trying to go any faster. Do that, and before long you’re positively flying through lumber at what seems like an unimaginable rate, you’re getting a better cut, and you’re not working nearly as hard.

At work, there’s a healthy cadence to the right kind of moving fast. It’s not chaos — I know the feeling of too many things going on at once, and that usually doesn’t work out very well. It’s also not a passive, stagnant feeling, where you’re waiting for a solution to unsolvable problems to fall out of the sky. Instead, the best environments have that perfect sawing rhythm, and when you’re really going, great progress seems almost inevitable. New process here, iteration here, letting something breathe over here, etc., etc., and so forth. Teams can feel when they are operating this way, and it feels good, as if even complex, existential challenges (while still difficult) are ultimately just waiting to hit the blade and be ground away.

effective speed is what really matters

Thinking this way requires a lot of things, but more than anything, it requires discipline. I’m not talking about the mastering-martial-arts kind of discipline, or even the learning-a-language kind. Just the kind you need to simultaneously realize what today’s limitations are while still understanding the extreme end of what’s possible, and then go out and achieve it. The idea that you can just get as psyched up as humanly possible, and then blast through your challenges like you’re running a Tough Mudder or something is, while in some ways laudable, usually mistaken. If you’re really trying to get somewhere quickly inside of a group, your effective speed — how fast you can actually get that group to make a lasting impact towards your goal — is a lot more important than how furiously you do various sub-activities, even if they seem like positives at an individual level.

You’re (probably) not going to solve the most important challenges with one great idea and ten bad ones all executed as quickly as possible, or a flurry of well-intentioned, disconnected exertion. You’re (probably) going to solve them by making well-executed, focused efforts, and yes… making those efforts a little quicker than everybody else. Because yeah, sometimes you just have to saw a little faster than the other guys.

Depth & Breadth

the most annoying people on LinkedIn

For me, LinkedIn has turned into a sort of career-focused version of WebMD. I almost never start poking around in there for an emotionally healthy reason — I’m either frustrated by something at work and looking to wallow in self-pity for a minute or two, or reading about whatever happened to that incompetent product manager I used to work with. And, as with WebMD, all I really get out of the experience are pangs of insecurity and a fair amount of eye-rolling horseshit.

Now, I have a decent amount of patience for the amount of terrible, uninteresting nonsense on LinkedIn. It’s an inherently self-serving environment, combining the narcissism of any social network with the naked greed and ambition that comes with private business and career advancement. My Dad, who has one foot in retirement after a long, interesting career, has the best LinkedIn profile ever (I’m pretty sure he only had it to look at people he was supposed to interview eventually). It has no accomplishments, no skills, lists one company he’s worked at, and has the same picture he’s used for everything that I’m pretty sure is from my junior year of high school. And it’s not like the twenty year old pictures some people have on LinkedIn, either. It’s not some idealized version of himself — it’s just the standard picture he’s used forever because my Dad places zero weight on your opinion of his appearance, or really anything else about him. Like, actually zero.

The polar opposite of my father — and the source of unquestionably the worst material on LinkedIn — is the insufferable “growth hacking” people, who are usually either digital marketing consultants (sorry, “CEOs” of their one person companies), or people who claim to have worked for like, eleven different startups in seven years. “NINE TIME STARTUP ENTREPRENEUR!!!” Uhh… congratulations?

You can spot these people by their long, self-congratulatory posts about how hard they worked, and how everything is possible through said hard work. (“AirBnB turned me down for a job out of school, but guess what? NOW I’M AWESOME!!!”) They are always white guys in their twenties, except for a couple of white guys in their forties, who are gods to the people in their twenties, and are advisors to no fewer than twenty-five different startups.


Obviously my resume is a little different, with fewer lasers and pyrotechnics. I’ve had real jobs producing some sort of fairly concrete business value since I got out of school thirteen years ago, in 2004. Other than one extremely difficult year in Cleveland, I’ve had steady, pretty intense employment at growth-focused companies the entire time, and I’ve learned at what I can only conclude is an above-average rate for a couple reasons :

  • the growth-focused thing; outside of Cleveland, I haven’t worked for a company on cruise control
  • the companies I’ve worked at have been pretty small, or early enough in their trajectory that you really need to pull your weight and often punch above it
  • most companies have had a strong technology component, and were in a new or rapidly changing industry
  • I’m a little bit of a generalist so I’ve gotten to have lots of different kinds of roles (support, product, marketing, leadership)

I’m very grateful for how all of this has played out, because I know for a fact that I work my hardest and do my best work in environments that really need me (this also explains my extremely inconsistent academic history). I’ve felt very strongly needed everywhere I’ve been since I moved to D.C. in 2008, and that’s not a feeling everybody gets to have.

But here’s the interesting thing; even though I’m really confident I’ve had an extremely productive, challenging, and enlightening first thirteen years of my career, I feel like I’m increasingly running into people who — on paper, at least — have done so much more. I’ll read a resume from a candidate with fifteen jobs, three major promotions, some kind of graduate degree, and one or more entrepreneurial experiences, and then realize they are three or four years younger than me. And the only thing I can think is… how did you do this? Are the annoying LinkedIn people right? Have I simply discovered a sub-class of superhuman professionals? Am I going to have to go back to working in the kitchen of that steakhouse from college again? (Just kidding, they’d never hire me back.)


This kind of thing used to freak me out a fair amount, until I started actually calling these people, interviewing (and sometimes hiring) them, and working alongside them. What I pretty quickly realized is that more often than not, these kinds of people take very little of substance from their experiences, maybe because they are so focused on title, perception, and the next step on their path. Once you experience this, the whole facade starts to crumble, and the realization is pretty jarring. If this is what this person wants to be doing more than anything right now, and they are just sort of so-so engaged, what does that say about their prior experiences?

This has been (and remains) my number one concern about going back to school for any kind of graduate business education. No, I don’t want to spend the money, and no, I don’t want to spend the time away from my kids, my wife, music, the gym, writing, and other things that have long track records of making me happier and smarter and better. But I really would consider sacrificing parts of those things if I wasn’t so worried that the whole experience is a great networking exercise bolted onto a bunch of faux-intellectual nonsense. Given that I have plenty to do, and great venues to do it in already, I’m worried that going to school is actually a less efficient way to learn than what I’m doing now.

I say that because, if you’re really in the gears of how a business grows and operates… holy smokes is there a lot to think about, design, execute, and learn from. That’s certainly true at FiscalNote, but it was true at Contactually, and EEx, and Bamboo as well, and even back when I was writing documentation and filing bugs, I always had access to the core questions and challenges of the business, and could feel the connection between them and my work.

I remember when our investors pushed most of the good people out at Bamboo (there was some personal stuff there). Almost overnight, it became obvious that we weren’t a “business” anymore; we were a bunch of people tasked with jockeying for the favor of our investor group as various people sought to extract cash out of what was left of the company. Some people saw that as an opportunity — “if I handle this right, I can be a vice-president!” — but I immediately knew I had to go even as it was made very clear to me that I was needed for this exercise. But what the hell is the point of working in business if you aren’t motivated by growing and improving a business? I had just turned thirty, so I left and spent the next couple of years frantically, maniacally building a functional company with my wife, which seemed a lot less crazy than whatever was going on Bamboo.

Five years later, I’m a little more sympathetic to the mortgage-havers and whatnot who didn’t have the luxury of my self-righteous professional/moral high ground. But many of those folks were further along in their lives and careers than I am even now, and had more to lose than I can fully comprehend yet. But the point remains that ladder-climbing and cache-gathering isn’t a cost-free exercise, whether you’re in school or at work, and that fact doesn’t always translate well to something like LinkedIn. Basically, resumes and the like are still great conversation starters and rudimentary framing devices, but at this point I now know there’s more depth beneath those titles and accomplishments than I may have fully realized in the past. Or in some cases, there isn’t, and that’s even crazier.

Insecurity 101

I was going to start this off with a really bold, all-encompassing statement like “the root of all problems is insecurity”, but then I thought about it for a minute, and realized that’s nonsense. Some of the worst problems I’ve ever dealt with professionally have come from people who were utterly and hopelessly secure about what they were doing, and in fact, those problems were in all likelihood largely a result of that confidence. Big surprise — most of these people were incompetent.

So anyways, like everything else, professional insecurity isn’t compatible with a snappy, Seth Godin-esque bumper sticker of a blog post. But it is a pretty big problem, and I’ll go so far as to say that most of the big problems I’ve had to deal with that involved talented, competent people resulted largely from insecurity about something or other. That being the case, it seems like something worth digging into a bit.

what do I mean by insecurity?

Not unlike Fight Club, the rules of workplace insecurity are short, and kind of meta. Most importantly, the first rule of workplace insecurity is that it’s almost impossible to exhibit workplace insecurity if you’re worried about your workplace insecurities. I know, what a relief.

What I mean by that is that everyone is insecure about something. That’s just life. Professional insecurity only becomes an issue when you lose track of it, and start thinking it’s something else, like a conspiracy to disrespect you, or a plague of implausibly exclusive incompetence that somehow affects everyone but you and a few people who allow you to complain to them. If you’re working on your insecurities — if you’re thinking about them, and being critical of yourself but pragmatic about how you can improve… well, it’s very unlikely those insecurities are causing anybody problems, even if they keep you up at night.

The truly dangerous insecurities are different, and they’re largely hidden. They often do sneaky things like project themselves onto others (so you can justify them), or create distractions that keep you from addressing them. Those are the ones I’m talking about here.

why are talented people insecure?

I’ve worked with a lot of talented people, and some of those people had insecurity problems that hurt their careers and/or their teams. Most of those people worked through those issues — in a few cases, I’d like to think I helped at least a little — and hopefully the rest will someday. With all of them, though, there were a couple of insecurity-causing scenarios that kept popping up.

(NOTE : There was almost always only one of these per person, although parts of one can overlap onto another.)

  • They took a disingenuous or unfair shortcut in their career, and deep down, they know they did.
  • Their life is based on achieving excellence relative to others, and as you get older and join higher performing groups, standing out from your peers gets harder.
  • Their personal identity isn’t really any different from their professional identity, so when they aren’t an awesome professional they feel like they aren’t an awesome person, and that scares the hell out of them.
  • They don’t want to do some portion of the work that’s necessary to truly excel (or they don’t think they have the ability to), but they aren’t comfortable admitting it.
  • They are objectively bad at something they think they (or people in their role) should be good at, and even if it doesn’t really matter, it makes them crazy.
  • Their job has required them to bullshit a lot (try raising capital, selling something that isn’t really done yet, or spending too much time arguing in favor of your subjective opinion, it’s hard), but they’re an inherently honest person and they feel, in some way, kind of guilty (whether they should or not).

I’m sure there are more than that, but even this list is a pretty broad swath of experiences that all contribute to the same kind of toxic behavior and thinking. In my experience, that behavior includes :

  • lack of empathy, and the feeling that empathy is often excuse making for others
  • a tendency to see weaknesses in a functional area as a result of someone else’s inherent, personal flaws
  • seeing the (often negative) outcomes you expect as inevitable, and any evidence to the contrary as someone’s attempt to deceive
  • frequent false positives that validate bad things about other people, or ideas, that the same person would normally detect as obvious confirmation bias
  • shutting down conversations or necessary arguments as “unproductive”, “pointless”, or “something we’ve already resolved”
  • exaggerated self importance (as if everyone cares as much about the person’s perceived weakness as they do)
  • projection of your perceived failings onto other people
  • the inability to concede portions of an argument and the tendency to conflate multiple, separate issues into a single, all-encompassing thesis people either “get” or “don’t get”

All of this sucks, and it’s frustrating whether you’re dealing with a friend, a boss, or someone you work with and are trying to build up. But… it’s not the end of the world, by a long shot.

the homer simpson boxing approach

For me, the only thing that’s ever allowed me to help someone deal with toxic insecurity is trust. Unfortunately, trust takes a long time to build — unless you’re a perfect match for someone socially, you aren’t going to build real trust overnight by going to a happy hour or on a weekend retreat. No, instead, you’ll work with them on something that triggers their darkest insecurity, and they’ll lash out at you in one of the many ways listed above.

At that point, I like to break out what I think of as the Homer Simpson approach, which is based on the awesome episode of the The Simpsons where Homer becomes an amateur boxer after his doctor determines he has an inexplicable condition that allows him to take repeated blows to the head without incident. Homer is a poor athlete and a terrible boxer, so his trainer (the always wonderful Moe the Bartender) convinces him to simply stand there while his opponents continually punch him in the face. Eventually, they’d become exhausted from all the punching, and Homer would then gently push them over.

It’s a great episode.

The point is, the reason many people act defensive towards someone else is because they are scared of how that person will react to something. Most of the time co-workers have aggressively approached me with complaints about a colleague, it’s a pre-emptive strike over an issue that multiple people (including the person complaining) are partially responsible for. Most of the time people react poorly to constructive feedback (sometimes by criticizing something unrelated I’ve worked on), they’re really just nervous that their work sucks, even if it doesn’t. But these aren’t firmly held beliefs, or even particularly well-thought out ones — they’re irrational, emotional fears, and they don’t last unless they get reinforced.

Hence, the Homer Simpson approach. When someone is exhibiting severe symptoms of insecurity in their interactions to me, I just… let them do it. I let them complain (although I gently remind them of oversimplifications or exaggerations in their complaints). I let them yell at me. I let them call me hypocritical, out of touch, blind, irrelevant, stupid, ignorant, and everything else in the book and simply focus on not doing anything to confirm or reinforce those assessments.

Eventually, unless someone is truly damaged (this does happen), they simply run out of defensiveness-fueled-rage, even if it takes multiple conversations. At that point, more often than not, you can get them to simply tell them what they’re really worried about. And once they do that, you can actually work on it.

postscript : the gandalf corollary

The Homer Simpson Boxing Approach is awesome, but it’s not a flawless answer — there are times where an insecure colleague will respond to your patience not with exhaustion and eventual trust, but by doubling down on the intensity of their attacks, or by incorrectly detecting weakness and turning those increasingly aggressive attacks on you.

When this happens, I’ll admit that I’ve been forced to apply the Gandalf from The Lord of the Rings Approach, demonstrated here by Gandalf himself.

This is one of my favorite scenes in any movie, period, mostly because it reminds me of the way my Dad used to deal with my notoriously explosive, self-righteous temper. He successfully applied the Homer Simpson Approach to my sister and I for years, constantly forcing us to exhaust our insecurities and defenses until we finally just gave up and leveled with him. But in certain moments, like Bilbo, we’d forget who we were talking to. Dad would talk to us as equals by choice — until we started thinking, maybe, just maybe, he was out to get us too! The subtle, clear change in voice he’d use when I was a kid to draw a line (“Now wait a minute…”, or “Hey!”) was never sharp, or defensive like us. It was just strong, almost like an audible reminder of the difference between making an argument based in fear and an argument based in wisdom. I’m pretty sure both me and my sister did that exact same cowering/running in for a hug thing that Bilbo does, except we were probably seven years old at the time, and Bilbo was like, a hundred and twenty or something. But still.

There are a million wrong ways to break out The Gandalf, so I’m incredibly careful with it. I’m sure lots of people (maybe me, sometimes) think they are doing it, but are really just acting on the same types of defensiveness and insecurity they think they’re disarming. But done properly, it’s often the defining moment in a professional relationship.