What I'd Tell the 17-Year-Old Who Started His First Business

Our first website was hideous. You can still find it on the Wayback Machine if you look. I check in on it sometimes just to remind myself: we had the world's ugliest website, but it was extremely effective. That's all that mattered.

I started my first real business at 14, a web hosting company with a friend. We figured out a good price point, found a simple product we could launch quickly, and used a reseller model that required zero infrastructure. No hardware, no servers. We just set up an account, built a website, and started selling.

We got listed on directories of web hosting providers, which generated significant traffic. That traffic turned into customers. At one point we added a free plan with small limits as a growth avenue. Get people in the door, then convert them to paid plans. It worked. We had a flood of free signups and decent conversion rates.

Then we learned a hard lesson very quickly.

One user ran up a massive bandwidth bill. We got charged, tried to bill the customer, and it turned out he was also a kid. He said there's no way he could pay. We were trying to collect something like $25,000 in bandwidth overages, which back then was real money. Today that would be maybe 12 cents worth of bandwidth. But at the time? Bandwidth was expensive.

Free generates activity. Free gets users. But if you don't have guardrails in place, it can backfire spectacularly.

We worried constantly about perception. We wanted to create this image that we were a big, established company. We had "multiple offices and locations." We had fancy phone numbers and 800 numbers, which seemed important because you wanted multiple ways for people to reach you.

But here's the thing: we were in high school. Having a phone number wasn't helpful when we couldn't actually answer it during the day because we were at school.

We had all these email addresses that just went to ourselves. HR. Legal. Customer service. Sales. In reality, it all went to the two of us. That was it.

We spent so much time on titles. On branding. On looking bigger than we were.

None of it mattered. Just call yourself the founder or president and move on. These days there are tools like virtual assistants and virtual receptionists if you really want to create a bigger look. But the energy we put into appearing legitimate could have gone into actually building the business.

Very early on we had a big influx of cash from customers signing up and prepaying for the year. And we spent a lot of that money.

Then we learned what happens when you have negative growth, when you're losing more customers than you're bringing in. That creates a real problem.

The lesson is simple: your number one goal is to bring in more money every month than you're spending. That's it. This is not rocket science.

If you're spending more than what's coming in, you either need to spend less or generate more revenue. That's pretty much the only thing that matters.

In terms of dealing with people (customers, partners, employees) I think the key is:

It's perfectly fine to say, "Hey, I need to look into this and I'll get back to you later." But being responsive is critically important.

When we had a significant amount of activity, it became hard to keep up. I would let things slip through just because there was so much happening. So prioritizing your inbox, making sure you at least respond with something, and then staying on top of follow-ups... that matters more than you think.

And speaking of follow-ups: follow-up is the name of the game. Most people don't do it right. Most people just give up after a couple of attempts. You have to constantly stay on top of things. Stay on top of people. People get busy. It's your job to follow up because the other people, your competitors, they aren't following up. When you do and they don't, that makes all the difference.

Also: it's easy to have a knee-jerk reaction and just say what you want to say. Maybe write that draft, sit on it for a while, and come back later. Especially if you're angry or upset, or if it's a response you don't look forward to sending.

There was constant doubt back then, and honestly, it still creeps in today. Why are we still doing this? Will this work out? Is this the right path? Should I just get a real job?

Staying motivated is the most important thing. Having a good attitude. Looking at the big picture and remembering you're in this because you want control of your time and the flexibility that comes with it.

It helps to see what other people are doing out there, what businesses are being built. Find peers. Find people you can talk to who are in the same position. People having the same struggles, or people who've had success and are where you want to be. I know I could do a better job building a bigger network. It's an ongoing challenge.

We were successful building community locally, and I think that's a good avenue depending on your business. If you have an online business it's a little harder, but you definitely want to build a network. Talking to other people, working through challenges together, that keeps you going.

I never seriously thought about quitting and going to get a "real job." This was just the path. This is what I do. You find a way forward. You adapt and overcome.

There are changes to the market, changes to products, changes to what you can deliver. These days with AI and all the tools available, you can move at lightning speed. But the fundamentals still matter. You still have to talk to customers. You still have to deliver something people actually want and are willing to pay for.

That's actually motivating in a way. Look at all these great new things we can do. Let's find a way to solve problems. Let's use these tools. Let's build something people are really interested in.

When you think back and ask yourself why did I start a company, why am I still doing this, you have to find what really motivates you. What really excites you. If you wake up and think, "Let me figure out what we can build today and create a really happy customer base," and sure, hopefully we make some money in the process... that will come.

I'm here to say it's always an ongoing challenge. There's no such thing as overnight success. You're constantly building, constantly learning. You're going to have bad years and good years. You will have challenges.

So to the 17-year-old who started his first business: keep going, but don't lose sight of the fundamentals. It's easy to brush that off, but it really does matter.

Cash flow. Building a good reputation. Talking to people. Being responsive.

That's what matters. Titles don't.