Reflecting on Milestones and New Beginnings

If I lost everything – the audience, the money, the reputation – and had to start over, here’s what I’d do.

Step 0: Take Inventory

What do I still have? My skills. My story. My scars. Just because the list is gone doesn’t mean the asset is. This helps frame that even starting from “nothing” isn’t truly nothing.

Step 1: Cry

I’d spend at least a week screaming into the void. “Why me Oh Lord, why me?” Then I would get down to business. I’d remind myself:

“There’s never been a better time to start over. The tools are free. The gatekeepers are gone. The only thing missing is your plan.”

Step 2: Pick a weirdly specific niche

I’d need to spend time to really find my purpose…my Tilt.

As Warren Buffett and Simon Sinek discuss, every successful person is really good at one thing. What am I really good at or know something about to truly differentiate?

And it’s not about being louder or flashier. It’s about being more specific, more real, and more essential to a group of people who need exactly what I have.

I’d need to work on it, but things like:

·         Helping laid-off corporate marketers build a business around one weekly email.

·         Guiding former agency owners to repurpose their network into a publishing-driven business.

·         Helping Midwest Gen Xers who want to escape the job ladder and own something by 50.

·         Coaching marketers over 40 to build businesses that don’t require social media.

·         Teaching people with 1,000 email subscribers how to make a full-time income.

·         Helping podcast hosts averaging over 10,000 downloads per month turn their show into a live event, a book, and a revenue flywheel.

I’d obsess over a tiny group of people with a burning problem.

I’d need to remind myself that you can’t be too niche. The more specific the better. I’m already thinking that a number of the ones I listed are not specific enough.

Step 3: Define Success

What will success look like? I’d spend some time visualizing what that could be. Family life? Money needs? Living situation? Career goals?

Basically, what do I really want here? What’s the dream?

Then, I would write that statement down in my journal and review it every day. Something like:

We are the leading event education resource for podcast hosts and sell the company for two million dollars in 2028.

Something like that.

Step 4: Start an email newsletter. Twice Per Week. Non-negotiable.

I’d write one useful, entertaining email two times per week. No fluff. No templates. Just my honest take.

This would be the home base for everything. The email list is the new land. Social is just rented space.

Even though I really like using Kit (how you received this email), I probably would opt for Substack, where you get the benefit of the direct connection (email) with a little more help from a network (social media).

Step 5: Spread the Word

I would create a list of 15-20 places where I believe my audience is hanging out, mostly other newsletters and podcasts. I would reach out and form relationships with these people to do guest articles and serve as podcast guests.

I would also prepare a few sample speeches and start submitting to relevant in-person events.

Step 6: Write the Book

As I create my newsletter I would start thinking about how I can take these newsletters and put it into a print, ebook and audiobook for sale. This will, ultimately, become my greatest marketing vehicle…the business card everyone wishes they had. Of course, I would use Tilt Publishing.

Step 7: Launch a product before I feel ready

By month 2, I’d offer something—a digital guide, a paid workshop, a 1-hour consult. Not to make money at first. But to get skin in the game and test what people will pay for.

Revenue doesn’t come from a viral moment. It comes from consistent service to a small, loyal group.

Step 8: Build in public

I’d document every win, fail, and lesson. Why? Because people don’t follow perfection. They follow momentum.

I’d most likely include my own creation strategies in every newsletter.

Step 9: Stack assets

By month 6, I’d package my best content into a course I could sell forever. Not for viral growth. For long-term leverage.

Step 10: Diversify into second channel

By six to nine months, I should have a small but growing email newsletter following, a newly published book, a speaking event here or there, some podcast appearances, a couple small consulting clients and a newly launched course.

If the small wins are there, I’d diversify into a second channel, most likely a podcast, which could also be a YouTube show. More than anything, this would be marketing for the main channel, the email newsletter.

Register for Content Entreprenuer Expo at CEX.events today.

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