I still remember the day we hit 1,000 users at RemoteTeam. I was sitting in my home office, staring at the dashboard. The number ticked over from 999 to 1,000, and I just sat there for a minute. It wasn't some crazy, champagne-popping moment. It was quiet. But it was profound. A thousand people. A thousand real human beings had signed up for this thing I’d poured my life into. It was exhilarating and, if I'm being honest, completely terrifying.
Everyone in Silicon Valley talks about the hockey stick growth, the viral loops, the overnight successes. Let me tell you, the reality is a lot messier. It’s a grind. It’s a series of small wins and painful lessons. And that’s what I want to share with you today. Not the polished version, but the real, in-the-trenches story of how we got our first 1,000 users and what I learned along the way.
1. Your First Users Are Gold
Forget about scale for a minute. Your first 10, 100, 1,000 users are your lifeline. These are the people who will give you the most honest feedback, who will champion your product, and who will stick with you through the inevitable bugs and crashes. I personally onboarded our first 100 users. I’m not kidding. My calendar was a mess of Zoom calls and product demos. I probably drank more coffee in those first few months than I have in my entire life. But it was worth it. I got to know our users, I heard their stories, and I saw firsthand how our product was making a difference in their lives. That’s something you can’t get from a spreadsheet.
2. Content is King, But Community is the Kingdom
We started a blog before we even had a product. We wrote about the challenges of remote work, about building a remote team, about the future of work. We weren’t trying to sell anything. We were just trying to build a community of people who were passionate about the same things we were. That community became our first users, our first evangelists, and our first source of feedback. Don’t just create content, create a space for people to connect and learn from each other. That’s where the magic happens.
3. The “One Metric That Matters” is a Myth
I used to be obsessed with our daily active users. I would check it every morning, and it would either make or break my day. But here’s the thing: it’s a vanity metric. It doesn’t tell you if people are actually getting value from your product. We started focusing on retention instead. How many of our users were still active after 30 days? That became our north star. It forced us to build a better product, not just a product that people would try once and forget about. If you're interested in learning more about how we approached metrics, I wrote another post on how to find your north star metric.
4. Don’t Be Afraid to Charge
We were so scared to charge for our product. We thought people would leave, that they would think we were greedy. But we were wrong. Charging for our product was the best thing we ever did. It forced us to build a product that was worth paying for. It also gave us the revenue we needed to grow our team and invest in our product. If you’re providing real value, don’t be afraid to ask for something in return.
5. Your Team is Everything
I’ve been lucky enough to work with some of the most talented people in the world. But it’s not just about talent. It’s about finding people who are passionate, who are resilient, and who believe in your mission. Building a startup is a marathon, not a sprint. You need a team that will be there with you through the highs and the lows. I’m forever grateful to the team at RemoteTeam for their hard work and dedication. We wouldn’t have been able to do it without them.
6. The Acquisition That Almost Didn’t Happen
The Gusto acquisition was a wild ride. When they first reached out, my gut reaction was 'no way.' We were on a roll, and the thought of giving up control was tough to swallow. But Josh Reeves and the team at Gusto were persistent. They got what we were trying to do. They saw the future of remote work the same way we did. It wasn't just about selling a company; it was about joining forces to build something bigger. It was still one of the hardest decisions I've ever had to make, but I have no regrets.
7. The Power of a Single Tweet
You never know what's going to hit. We spent weeks planning our big launch for a new feature, and it was a total dud. Crickets. Then, a few days later, I randomly tweeted a screenshot of a small UI improvement we had made. It was nothing special, just a little tweak to make the interface cleaner. But for some reason, that tweet took off. It got retweeted by a few big names in the design community, and all of a sudden, we had a flood of new sign-ups. It was a humbling lesson in the power of serendipity.
8. The Messy Middle is Where You Grow
Everyone talks about the beginning and the end of the startup journey. But the middle is where the real work happens. It’s the messy, chaotic, and often frustrating part of the journey. But it’s also where you learn the most, where you grow the most, and where you build the resilience you need to succeed. Embrace the messy middle. It’s where you’ll find your strength.
9. It’s a Marathon, Not a Sprint
I’ll say it again: building a startup is a marathon, not a sprint. There will be times when you want to give up, when you feel like you’re not making any progress. But you have to keep going. You have to keep pushing. And you have to remember why you started in the first place. For me, it was about building a better future of work. And that’s what kept me going, even when things got tough. If you're a founder, an aspiring entrepreneur, or just someone who's curious about the startup world, I hope this was helpful. It's not an easy path, but it's a rewarding one. And if you're in the thick of it right now, just remember to keep going. You've got this. And if you want to read more about my journey, check out my post on my biggest mistakes as an entrepreneur.
Frequently Asked Questions
Are these recommendations still relevant in 2026?
Absolutely. While specific tools and tactics change, the underlying principles remain consistent. I update my thinking regularly based on what I'm seeing in the market and across my portfolio companies.
How were these items selected?
Each item on this list comes from direct experience, either from building my own companies or from patterns I've observed across the 200+ startups I've invested in. I prioritize practical, actionable items over theoretical concepts.
Which item on this list has the highest impact?
It depends on your stage and context, but in my experience, the items near the top of the list tend to have the broadest applicability. That said, sometimes the less obvious items create the biggest breakthroughs for specific situations.