What I wish I had known

Six months ago, we sold ReallyGoodEmails.com after a decade of building it. Most people still don't know this, but RGE never had a full-time employee. Sometimes it felt like we were full-time since we dedicated hours of our nights, weekends, holidays, and the occasional lunch break to it. Our kids, wives, and partners often called it our "other family." And for what we couldn't do because of our day jobs or lack of knowledge, we contracted out to some amazingly talented people.

RGE wasn’t just a business—it was a wild side hustle that turned into something much bigger than any of us imagined. I’ll be honest, hitting the 10-year milestone had me reflecting on what I’ve learned over the years—not just about email design, but about the whole process of creating something from scratch with weirdos from the internet I had never met before, and then working (often async) to grow into a community-driven beast.

When you’re deep in the grind, it’s easy to lose sight of the bigger picture. But now, with some distance (and a little time to breathe), I’ve realized there are lessons we learned with RGE that can be applied to anything—whether you’re building a product, a community, or just trying to survive in this fast-paced world of creative work. So here’s a rundown of the top 10 things I wish I had known back when we first started ReallyGoodEmails, along with some pitfalls to watch out for along the way.

1. Imposter Syndrome is Real (Especially at Your Own Event)

Hosting UNSPAM for email pros—many of whom could run circles around us—was intimidating. But having our own event showed us the real impact of our work, and that gave us the motivation to keep going. Lesson? Even if you feel like an imposter, you’re making an impact.

2. Side Hustling Ain’t Glamorous

Running RGE as a side hustle was tough. There were times we couldn’t give it the attention it needed. But, having it as a side gig meant we could survive the early days when it didn’t make money. If we’d gone full-time too soon, we probably wouldn’t have lasted.

3. Do Things That Don’t Scale

We still do the unscalable stuff—personally replying to emails, doing deep research projects, and interacting with our community. That personal touch made all the difference. It might not scale, but it makes you stand out.

4. Good Swag Makes a Difference

Our swag wasn’t cheap stuff with a logo slapped on it. We made high-quality gear that people wanted to wear. Lesson: Good swag sticks with people and leaves a lasting impression.

5. Reinvest in Your Vision (Not Your Wallet)

We barely paid ourselves in the early days, choosing instead to reinvest in making RGE better. This kept our focus on improving the community experience, but we did lose our way a few times building things we thought people wanted without checking first.

6. Embrace the Weird

We leaned into our quirks—being real, fun, and just a bit weird. It helped us stand out in a sea of corporate blah. If I could go back, I’d tell myself to double down on that weirdness even sooner.

7. Data and Distribution Are Your Best Friends

Our email trends analysis put us on the map. Leveraging our unique data and distributing it smartly opened doors for speaking gigs, guest posts, and great SEO. Share what you know and get it in front of the right people.

8. Learn How to Say No

When our traffic blew up in 2020-2021, we wanted to do everything, but it almost burned us out. Lesson: Saying no is tough, but it’s crucial. Focus on what matters most, and leave the rest for another day.

9. Find Those Who Will Help

Don’t try to go it alone. We had amazing support from smart and fun co-founders, but also early partners like Mailchimp, Airbnb’s marketing team, and Metalab. Those relationships gave us the boost we needed when we didn’t have the resources. Find your allies.

10. Community and Kindness Go Further Than You Think

We wouldn’t be here without the community. People have stuck with us because we treated them like people, not just users. Building something meaningful is about showing up, being kind, and giving back.

10 years. 10 lessons. And if I’ve learned anything, it’s this: Keep showing up, keep experimenting, and have fun while you’re at it.