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TL;DR - Scroll down to get a 1-week discount on my book — and an ask for a review!

It's my 5 year self-employment birthday!

I can’t believe I’ve been in full-time business for five years.

I left my job in March of 2021, after having prepared for it for about a year.

And what a time that was.

Five years ago…

Courses and cohorts were booming (and the big creators were still touting their digital course programs).

Interest rates were at historical lows and the stimulus packages were driving spending. But, the inflation driven by that cash and supply shortages hadn’t yet rippled through the economy.

ChatGPT and Claude were just a twinkle in their engineers’ eyes — not yet a driver of an unsustainable credit bubble slash existential threat to employment.

LinkedIn wasn’t completely overwhelmed by templates and AI-generated content responded to by AI commenting bots, and you saw the static feed posts of the people you followed on Instagram!

Ah… the good old days.

5 years really gives you a vantage point of what matters and what doesn't matter.

The hype around NFTs? Didn't matter.

The laughable quality of my first workshop graphics? The performance of a given reel? A blip in time.

How freaked out I was that my LinkedIn newsletter didn't get sent to everyone immediately when I launched it? Didn't matter.

The price points and names of my first programs and services? I've changed prices and program names so often (including lowering prices in many cases) as I learned who and how I liked to serve.

The sales calls where I freaked out and underpriced my proposals? Heck, I sometimes do that today when I custom scope stuff.

But in the long run? None of that mattered.

What did matter?

I kept learning. I kept going.

I kept putting my work out into the world—more consistently, more directly, and through far more relationships than I expected.

No matter what the Entrepreneurial Casino tells you, the 1000-day rule is real. Getting to sustainable momentum (not just making money) takes longer than you think.

Building your relationships and network ecosystem takes time.

Building your intellectual property takes time.

Building your own skills takes time.

And for all of that to compound into reputation… takes even longer.

My five-year journey spanned:

• Three rebrands.
• 260 newsletter issues.
• 48 free monthly classes.
• Over 100 podcast interviews and guest appearances.
• Countless coffee chats.
• So many programs and communities.
• And a book.

Phew.

I’m thankful for every contract gig I had, every bridge job I took, and every fractional role that helped me stay self-employed long enough to actually build the business I dreamed of.

I’ve learned a lot in five years — lessons I’ll share over the coming weeks.

The only reason I'm still here?

Because of you. Because of the relationships that surround this business.

I started with about 50 friends and colleagues reading my newsletter, and my work was mostly in-person in Charlotte.

Now this newsletter reaches thousands, and members are joining from as far as South Africa, India, and Australia.

Every week I talk with Deeper Foundations clients and members—many I’ve never met in person, and none of whom I knew when I started.

This year I’m traveling to Boise, Savannah, Boston, Chicago, Portland, San Francisco, Seattle, and LA to see friends… who didn’t exist in my world five years ago.

When I went to New York a few weeks ago, the people I texted for drinks were people I met through this business.

Some of you have been here since year one. Some of you just found me this week.

I’m grateful for all of you.

So thank you for being here.

For trusting me every Sunday in your inbox.

For sharing my work.

For participating in my programs.

For letting me be part of your work and your worlds.

It means more than I can say.

A celebration (and an ask) to mark five years…

If you’ve gotten value from my work, the best way to support the next chapter is to help more people find the book.

I’m running a 50% anniversary discount on Leaving the Casino through March 30.

Use code BIRTHDAY50.

And I’m also close to hitting 50 reviews on Amazon—we just need 12 more.

If you’ve read the book and found it useful, leaving a quick review would mean a lot. It’s one of the main ways new readers discover it.

And truly—thank you for being part of the first five years of Deeper Foundations.

I can’t wait to unveil some plans for the the next five years.

NEW EPISODES

Notion, ADHD, and Actually Useful AI Agents with Meighan O'Toole Many conversations about AI in the entrepreneur space default to content generation — blog posts, social captions, first drafts. But that’s only one layer of what AI can do, and for a lot of people, it’s not even the most useful one. In this episode, we’re joined by Meighan O’Toole of Ops+Bots, a Notion architect and workflow specialist who helps small teams build scalable systems they’ll actually use. We talk about the real difference between LLMs, chatbots, and agents; where Notion AI genuinely shines (and where it doesn’t); and why the tools that reduce administrative burden can be a genuine lifeline for people managing chronic illness, ADHD, or financial constraints. Listen to the Pod