At the end of February, I left my job at Botify after an extremely eventful two years. I enjoyed my time there, and worked with a lot of cool people (from all over the world!) in a very weird, largely COVID-dominated environment that forced me to interact with everyone almost entirely via Zoom and Slack. Botify had an excellent financial 2021 as they continue to move up market pretty quickly, and just raised another $55 million dollars to do everything bigger and faster.

Also… I got extremely bored.

This isn’t really Botify’s fault, per se. Part of the appeal of working in a startup environment — in theory, at least — is that every one is different, and the capacity is always there to chart a new course. But that’s more mythology than anything else, because I’m actually talking about a very specific flavor of startup — the venture backed, B2B kind that tends to want to hire people who do what I’ve historically done. And those are… basically all the same. That probably sounds like lunacy to many of us who spend our time working in the nooks and crannies of different businesses, mastering obscure industry workflows and customer personas, but those are just the details. The details are important when you’re actually operating — you can’t ignore them — but in terms of fundamental challenges, when you zoom out (as I have after 15 years of this), it’s really just the same thing over and over again.

1. Find an inefficiency (especially one that results from things being not-distributed, or not accessible, or something else internet dust could conceivably address).
2. Raise some money, get a growth target from investors.
3. Do crazy, wacky things like listen to your customers. String everything together. Make a lot of slide decks. Hit some growth targets, miss some others.
4. Realize you need a lot more money to do this the way you want, or more commonly, the way your investors want.
5. Raise more money. Get a bigger growth target.
6. Look for richer customers. Maybe get one or two. Realize if all your customers were like this, you’d be fine.
7. Move UPMARKET.
8. Realize moving upmarket is very expensive. Raise more money, get an even bigger growth target as a result.
9. Move UPMARKET-ER

This is usually about when I quit. The reason I tend to last about 2 years at places like this is that, if you do a good job, that’s about how long it takes to go from “let’s move upmarket” to “this is great, let’s move upmarket-er”. The latter is when you really start to get removed from your product, increasingly dependent on relationship selling and professional services, and if you do it right, start to make a ton of money. We all turn into our parents or die trying to, and our startups all turn into Oracle or die trying to. I’m kidding, but only a little.

None of this is even remotely unique to Botify; I’ve literally done this four times now with different details but essentially the same fundamentals, which in short are “how do we take what we already have and make it interesting to people with insane amounts of money”. Doing this at FiscalNote — soon to be a public company! — from 2015 through 2018 was one of the most rewarding challenges of my career. I can’t take a lot of credit for pulling Gooten out of the dumpster (a lot of that work happened before I got there, which made hiring me even possible), but it was definitely challenging and interesting, even if the mechanics of the business model were a little different (more on that someday). Botify was, situationally, almost a carbon copy of FiscalNote’s up-market-er scenario, and at some point you just feel like you’re watching some forgettable slasher flick on TNT late at night, yelling “NO, DON’T GO IN THE OLD BARN!!!” at your TV. You need to watch some different kinds of movies, or go to bed.

Another Movie

My Dad never pushed me into sports, which I am generally really grateful for, as I have a very healthy relationship with sports as a crazy middle aged man from New England, and that’s not as common as it should be. But he did want me to try playing organized basketball instead of baseball, because I was objectively horrible at baseball (and often miserable even though I loved it), and weirdly good at driveway basketball. I didn’t listen — I was too nervous to try something new and fail — and as a result, I never got as good at basketball as I probably should have, given how much I loved it and was willing to work at it. As I got older, I eventually stopped playing baseball anyways, kept playing basketball at the playground, and eventually battled/hustled my way onto the junior varsity bench of my high school team where I turned the ball over constantly and was generally terrible and unplayable. Then again, I also chased down a kid once and blocked a shot off the glass to the delight and delirious cheers of my varsity teammates, a silly moment I remember to this day. Basketball was good to me and I will always love it.

Is Marketing is my baseball? Something I keep doing because it’s the first discipline I found that would take me, but ultimately not what I should be doing? Or is it the version of basketball I managed to avoid (thanks, Dad) — the thing I’m ultimately wired best for, but one that I’ve spent too much time with and thus simply don’t want to do anymore? I don’t know the answer (although I have theories, clearly), but either way it’s not something I should be doing right now if I can avoid it, and the fact is that in rampantly inequitable, tight-labor-market America, I can absolutely avoid it right now.

So then… what now?

I’m in a weird position. I have some subject matter expertise in a bunch of fairly useful, lucrative things that I don’t really want to do anymore, namely high growth sales & marketing process/strategy/tactics. I’m also pretty plugged in to the basics of modern software applications at a time where those things are really important and affect a lot of people. I’m not going to pivot to being a developer — I took computer science in college, I know not just that I am bad at this, but exactly why and how — but I’ve got some real literacy there. Also, I’m kind of a lunatic and I’ve done a lot of overthinking for the last four or five years about how businesses work.

All of this is why I am making a product. It’s called Resolution, and I’ve actually been working on pieces of it (and then throwing those pieces out and starting over) for a couple years now, in the background of going to work and raising kids and making my wife laugh. I’ll have a lot more to say about Resolution soon (duh), but here are the details that exist now and are important to me.

• Resolution is a general purpose tool designed to help non-math professionals use real math along with their own expertise to make better plans and decisions.
• It is not magic. It does not use AI/ML or do anything predictive. It might someday, but that will never be the core point of it. Instead, it will often make you smarter. But it does not do your work for you.
• I have been looking for something like Resolution for the last five or six years, to address a problem I’ve used whiteboards and spreadsheets to solve, but it is very much neither a whiteboard or a spreadsheet.
• I have not raised any money to build this. It is currently bootstrapped and self-funded (thanks, years of tech industry jobs!), and is being built by me and the fine people I’ve hired at Viget.
• The initial version of Resolution isn’t going to be fancy, but it is going to be cool and potentially useful to you. I have a big long, exciting (and feasible!) roadmap of additions and improvements that I think many of you will love.
• I will probably have some kind of Kickstarter-like thing to fund the next round of improvements, where you’d get access to this version in the meantime. But it’s not vaporware; I’m using it right now, and we should have something legitimately cool for you to try early this summer (or maybe even earlier).

The Part Where I am Weird

The toughest part about explaining Resolution to people is that there are several stories to tell inside all of this, and despite being generally disconnected, they are all pretty important and fairly nuanced. But in order of importance, the short versions are:

1. There is a huge gap between “data driven decision making” culture and people’s actual holistic understanding of what they are working on, and I think a big part of it is caused (or at least not improved) by the kinds of tools we use every day. This is the product/problem story, and that’s really what is most important to me and the driving impulse behind everything.
2. I have become increasingly disenchanted with how software is thought about and built. Entirely AI/ML-based solutions to everyday problems are simply not viable yet, and we’ve allowed the fact that ML can legitimately do some really cool things (like find pictures of things) to convince us that it’s going to be able to do the hard parts of our jobs (or our team’s jobs) soon. This is delusional, plain and simple, and I think very little energy is going into dealing with it.
3. Much of this is due to the fact that B2B software is dominated by venture-backed companies that have no long-term strategy other than being bought by a huge company (where their product will die from internal politics/innovator’s dilemmas or simply be forgotten about), or improbably IPO-ing and turning into Salesforce, at which point it will be able to be a piece of shit without any market consequence.
4. Therefore, as important as my product vision & purpose is (and it’s very important, that’s why it is first on this list), my “corporate” vision and strategy is almost as important, because simply going by the book and doing what I’m supposed to right now (“4x ENTREPRENEUR MARKETING GUY RAISES SERIES A, BECOMES QUIPPY THOUGHT LEADER”) would probably be a wild ride if I was even able to pull it off, but would absolutely not result in (a) good software or (b) solving the problem I’m allegedly passionate about. If I build a “lifestyle” business where I’m taking home what I’d be taking home at one of my normal jobs, but this thing is awesome and cheap and improving, and people are going less crazy at work because of it, I will continue doing that forever until I die.

In short, I never wanted to be a guy who started a business without a real purpose just because he wanted to be in charge or feel important, and — I swear to God — I don’t feel like that’s what I’m doing now, which is good. That being said, do I want to be in charge? Do I feel important? Yes, and… sort of yes, I suppose.

But that is all largely irrelevant. I will either get to do this because I build something useful and successfully get people to use it/get value from it/pay for it, or I will not, and I will be back at work somewhere teaching sales guys how to sound like they have some idea what they are talking about. It’s a living, and it’s a living I’ve enjoyed at certain points, and a bunch of people will vouch for me that I’m pretty good at it, so if that happens I’ll be fine.

For now, though, I’m just happy to be focused on thinking and building, at least for now. I’ll have lots and lots to share in just a couple weeks, whether it’s in this space, or somewhere else.