The end of the year always lends itself to reflections, and this year in particular feels ripe for thinking back on what I’ve learned about building a business. It’s been the worst year in our 14 year history as a company, and it’s for reasons outside of our control. The SaaS implosion that happened in 2026 took a huge chunk out of our business for about 9 months, and it’s slowly starting to recover. I sit with a lot of emotion around that event, everything from frustration to sadness. But in times where this happens it’s helpful to zoom out and think about things on a broader level. So here are the biggest things I have learned from 14 years building a multi-million dollar business completely bootstrapped.
As cliché as it sounds, it really is all about the people. The people who work alongside you on your team, the people who use your product, the people who work with the people who use your product. This is what truly saddens me about the AI boom. Because AI makes people think they don’t need people. I’ve seen so much destruction of relationships over people turning to AI and thinking they can now just lone wolf everything and make all the money. It’s created a zero sum mentality that is really just a bummer. But there are glimmers of hope as some people are starting to wake up and see that you can’t just use AI to make a million dollars in a basement, unless you are scamming people. And that’s not going to last very long. As I look back at our business. The biggest gains come from times when our team is clicking. We are working together smoothly and quickly, with deep trust amongst each other and the ability to have ideas flow. The best breakthroughs happen when we are playing it fast and loose, within a system where we know where we are headed. Customer relationships, and collaborator relationships, matter equally. Building those takes time, patience, persistence. There is no such thing as rushing it, and that’s also what AI has totally wrong. If you are going to build something as fast as AI has built, it will also dismantle as fast as it grows. Because what creates steadiness is a strong base of relationships with customers, with partners, with a team that can continue to deliver. When everything is based on fast growth and faster money, it will all collapse as quickly as it started. This point has been especially hard to remember in 2026 as it seems like the whole world has flocked to a fast-fire, fix all the problems overnight, mentality. Of course it is great to adopt new technology and new ideas as they come out, but dropping everything to go chase a shiny object is a sure-fire way to burn all bridges at once. And that’s what has happened for a lot of businesses in the past few years. For ourselves, the reminder is to always stay true to building positive connections, even if there is turbulence.
Build routine around the business. It’s a long game. Sometimes you have to sprint, other times it’s more of a gradual drum beat. Whatever phase you are in, building a routine is vital to the long-term success of anything worth building. Nothing special happens overnight, which again, speaking of the AI, just because you can make it look like you did something worthwhile in an hour, doesn’t mean it is. things worth building take time because you have to figure out every little aspect of how to deliver a product or a service that truly works for your customers. What issues will they face? what questions will they have? where do they need you to lean in and help? those things are what makes a truly great product or service stand out from one that is a fly-by-night operation just trying to get you to give them money. And doing this for a very long time is not something you can fake. And it’s not something you can outsource to an AI. It’s a distinctly individual experience that takes years to develop. I can hear the AI bros breathing down my neck right now being like “yah but can’t you just program that into an AI?” The answer is Yes, sure, if you want to spend 10 years talking to customers, figuring out what they need, building it, iterating, and programming all of that into an AI, be my guest, or just do it yourself and save yourself the headache of trying to maintain an AI that does the same thing you are doing, and takes the same amount of time to get up and running, have fun. I’m being somewhat sarcastic, but not really. It takes a really long time to root out all the issues you can face, even in a seemingly simple business. There are a thousand little problems customers deal with, and they want you to have the answers. If it really was so easy to just program it once and let it run, we’d all be doing that. And we’ve had AI for long time now, it is not doing that. Human nature would tell you that even if that did work, it would stop working immediately, because human needs change rapidly, and what worked yesterday is not what works today. So as soon as you took all the time to program it one way, you’d have to start over. What’s better is building a routine around adapting to what customers want and need. Harkening back to it every single day. Listening to what’s changing and meeting the moment constantly. Some things will stay the same, and those have to be rock solid. Other things will adapt to what the world is doing right now, and you have to stay in lock-step with that. The only way to do this over a long period of time is to have a routine around how you help customers. How you build your product. How you listen to what people need. How you make sure you are still delivering value. Set it and forget it was never reality, and AI isn’t going to change that.
Emotional regulation is the only way to sustain a business. There are days when everything is terrible. Or in the case of 2026, a year when everything is terrible. Truly this year we have seen a market where the idea of paying for software was seen as not just a bad idea, but an outright sin. That was wild, and it is now passing with each day we realize there are trade-offs to using AI for everything, particularly with time it takes to build from scratch and the customer backlash against AI-looking apps. It honestly comes down to whether or not you can enjoy the work. The building, the creating, the writing, the connection, the collaboration. If those things sustain you, it’s much easier to stay regulated than if it’s just about the money.
These are the top things I’ve learned over my 14 years. This is a somber reflection after a year in which AI tried to take over the world. But people are kind, people are resilient, people are thoughtful. And we will find a way to make a brighter future for everyone where we can work with one another towards better businesses, better communities, better relationships, and AI as a new tool and facilitator is going to be a part of it, just not the quick fix we got pulled into this year.
