Celebrating the 4th anniversary of my newsletter

There’s a party going on right here

This week marks the 4th anniversary of my newsletter. It’s a milestone I’ve looked forward to celebrating!

On May 14, 2018, I sent out my very first newsletter. It had the subject line “Week 1, Day 1: The Side Hustle.” Over the next ten weeks, I sent daily emails on how to start a self-funded small business. It was…a lot.

Some of you still have those emails. About 50 of my readers have been here since the very beginning. Thank you for your support!

Special thanks to journalist and copywriter Margot Carmichael Lester of The Word Factory, who generously shared her pro tips for writing faster and in my own voice.

Soon after those ten weeks ended, our family moved to Spain for a year. I switched to writing a weekly newsletter that evolved into equal parts personal travelog and business tips, ultimately writing 80 newsletters in my first year.

I started this newsletter because I knew the importance of having my own list. I didn’t want to build my growth plan on the algorithmic whims of social media. When I started, I was halfway into my “five years to kindergarten” plan.

While the massive kindergarten-enabled growth surge didn’t happen, a two-year small business emergency did. Having this newsletter gave me the opportunity to support so many of you in accessing pandemic stimulus and navigating an ever-changing operating environment.

We’ve covered a lot of ground in the last four years. In celebration of this anniversary, we’ve selected five of our most popular newsletters and added them to our blog:

In particular, “Give yourself a raise” reminded me of all the reasons I want you to be a thriving and profitable business owner. The changes in my own life in the last 18 months were largely possible because I believed in my own ability to be financially independent. And with that independence comes the opportunity to invest in myself, my son, better food, healthcare, campaigns and candidates, and other entrepreneurs.

I have so many things I want to write about in the next few months. I’ve had a metaverse / web3 email in the works since September that I’d love to finish. I have half a dozen people among my clients and partners who I want you to hear from about their own areas of expertise and leadership. And I continue to be committed to writing at least one email a month on business operations and management fundamentals for self-funded small businesses.

I love and appreciate knowing that this newsletter helps you in any way. Tell me, what topics can I cover? What questions can I answer? Tell me! We’re working on our summer content calendar now and I welcome your suggestions. And if you aren’t already, you can subscribe to the newsletter using the link below.

Thank you for reading.

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