Decade

Customer demand. No amount of cleverness, flawless execution, or external funding can fix a lack of customer demand. And massive customer demand can overcome a whole bunch of dumb ideas, poor execution, and limited resources. I think my ideas and execution weren’t terrible but fundamentally I was able to wade into this business because there was so much demand so early on that it gave me time to learn.

Pricing. I used to think there was some kind of standardized pricing that the market agreed upon and that was that. But pricing is a story we tell ourselves. What price do your customers WANT to pay? The answer is almost never “as little as possible.” The answer is “an amount that makes them feel like they are making the RIGHT decision FOR THEM.” If they think something is hard and important they will WANT to pay “a lot” for it because they will feel more assured that they are making a smart investment and that it will go well. Our ability to consistently price ourselves at the high end of our market has been a core ingredient of business health, second only to…

Culture. Man I thought this was such an empty buzzword ten years ago, and man was I dead wrong. When you’re working in a volatile, uncertain, complex, and ambiguous environment (aren’t we all?), culture is how decisions get made because there is no documentation or set of policies that can capture everything an individual will work on all day. It’s like the culture in yogurt or sourdough bread: culture spreads to encompass the entirety of the container it is placed in. It determines the taste and texture of the whole endeavor, and it is how growth happens - or doesn’t.

Further - good culture is not “it’s fun to work here.” Culture must be strong and specific enough such that it is NOT fun to work here for SOME people - otherwise it is just too generic to be useful. I was not intentional about this early on, I just wanted to be liked and I wanted everyone to enjoy themselves at work. In the future I want to be exceptionally clear about our company culture and I will know I’m successful with that when some people - the wrong fits - self-identify their way out of the company.

Taxes. There have been five or six moments where I figured out something (fully legal!) we could adjust with our taxes that would save the company $10k or more. When you’re a W2 employee your taxes are fairly straightforward and you don’t have that many moves open to you. When you own a business and the business income passes through to your personal return, you have dozens of new, impactful, government-encouraged moves you can make. Now as I think about starting a new business I am thinking about the tax implications from day one.

Rules of the game. By my nature I don’t care that much about other people’s expectations and constraints. So I assumed my team members would feel the same way, and I gave everyone wide open latitude to approach things how they wanted to. But that leads to confusion and stress because people have to do a whole lot more guesswork. It is kindness to just tell people straight up how to play the game here, where the boundaries are, and how to win. This is hard for me to do and I am still learning this lesson.

Self-awareness. This is obviously always good to have. But the degree to which it is connected to financial success for my company is something I didn’t realize before being in this seat. On a weekly basis this job pushes me to get to know myself better, and I can see a direct line between my ability (or at times, inability) to do so and how we perform as a company. It’s almost spooky. This is probably worth another post or two at some point.

Optimistic teammates with high integrity. This is also pretty obvious. But wow it is an astonishing gift. It feels like a gift because even though you can try to hire for these traits, you just never really know how it’s going to go once someone starts work. So when people show up day after day with a good attitude and then they do the things they said they were going to do it’s like…damn how did I get so lucky to find these humans?? You’ll never hit 100% of your team in this category but all you need are 2-3 and your workplace is transformed.

Autobiographies. I’ve read 250+ business books in the past ten years.¹ The “Here’s a framework for how to run your business” books have been mostly useless. The honest and specific stories told by people who did big and hard and quirky things are extremely helpful. Especially if they did that in a totally different field, I harvest so many ideas from trying to connect the dots from their life to mine.

Being in person. We have been a remote-first company since 2018 and there is no way we could have assembled the talented crew we have now without that model. BUT I still hate it. I don’t believe humans are wired to just be thumbnails on a screen all day long. When I look back at the various people challenges we had, I fully believe 95% of them would have been easily solved or just not a thing at all if we all worked in person together. Instead of someone sitting on something that needed to be said for weeks or months because it didn’t feel big enough to Slack someone to ask to chat, if we were all in person those people would have made eye contact and someone would have said “hey can you come get coffee with me?” and they would have sorted it out.

Another great example happened for me last week. I coincidentally happened to be visiting a city where one of my teammates lives, and this teammate was seriously considering taking another job - they had done two interviews and were a finalist for the role. We got lunch and just chatted about work and life and the future, and I didn’t bring any pressure to the conversation in any way, just expressed support for whatever decision this person wanted to make. The next day, this person messaged me to say that they had decided to stay in their current role with OpenTent. Perhaps we would have reached the same result from a Zoom conversation - but I think there was something to the experience of “we’re humans and this thing we’re trying to do together is real” that can only come from eyes looking into other eyes, not into a screen.

ART. We spent $12,000 on custom art for our website, hand-drawn by a Portuguese couple. It felt a bit insane at the time but now I have no doubt it has more than paid off. We are constantly told by clients and job applicants how much our company energy comes through our website, especially in comparison to our competitors. I freaking love it.