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My Story
Two and a half years ago, I had a little over 500 LinkedIn connections and decided to post every day with the aim of finally building the audience Gary Vaynerchuk had been telling me I should build for over a decade.
I studied content and built relationships with other creators. I took Justin Welsh’s LinkedIn MBA and Ship 30 for 30, then invested $5,000 in Chris Donley’s Creator Accelerator, one of the best investments I made during that period.
I learned how to grow.
My work has since generated more than 40 million LinkedIn impressions. My audience across platforms now exceeds 75,000. That includes 50,000 on my LinkedIn pages and 10,000 on TikTok. Here on Substack, Operating has 12,000 followers and 6,000 subscribers, and has become a bestselling publication.
For the first 18 months, I had neither a clear offer nor a clear enough purpose for the newsletter. I assumed that if I built the audience, the clients would come.
The expertise behind my best-paid work was available before any of that growth, but it was hidden within the consulting engagements that had long been my bread and butter.
My first offer was 4 hours of my coaching time for $99.
It sold +100 seats in 12 days.
I wanted to learn how to build a coaching offering. I wanted to do something crazy and unscalable that people would talk about if it succeeded. During those hours, I listened to the work and business challenges each member was facing and helped them solve the problems they brought.
Many wanted help scaling a newsletter, improving their content, or growing an audience. Most were trying to figure out what to sell and how to make money as solopreneurs. The conversation would get into the business underneath the content.
Then there were the people who already owned larger businesses. They brought 4 kinds of problems:
AI transformation.
Enterprise technology and software that needed improvement or optimization.
Sales and inventory operations strategy.
Growing EBITDA ahead of a business exit.
These were the kinds of challenges I had spent years solving in businesses I operated and companies I advised. When someone needed further help, I offered a larger coaching engagement. From there, I moved into the work I had been doing throughout my consulting career: understanding the situation, scoping the work, and building a proposal. We negotiated the engagement and decided whether to proceed.
That part was familiar. I knew how to understand a business problem and propose work to address it. I had been doing it for years.
A number of those coaching members became consulting or advisory clients. That work has brought in hundreds of thousands of dollars this year. I expect it to continue into next year.
The coaching offer itself was massively unsustainable. Four hours for $99 works out to $24.75 per coaching hour, before preparation or follow-up. More sales meant more time committed at that rate.
Those first 100 sales brought in roughly $15,000 in gross revenue. I was getting paid to learn how to build a coaching offering and whether I wanted to keep doing it. I eventually decided I did not want to build that coaching business.
The experiment also became a paid way to meet people who needed larger consulting and advisory engagements. Judging it only by the hourly coaching rate would miss most of what it produced.
Oper(AI)te™: The Hidden Offer is a four-week live build designed to turn the expertise, results, and experience you already have into an offer people will pay for. We’ll help you find it, validate the market, price it with evidence, publish the sales page, and build the AI systems that help sell it. You already did the hard part: becoming exceptionally good at something. Now we’re going to make it buyable.
Some people wanted advice on building an online business. Others needed the operating judgment I had developed long before I started publishing online. The conversations helped me understand the difference and decide where to put my work.
I spent my twenties studying economics at Harvard and the University of Chicago. I spent my thirties helping my father build, scale, optimize, and eventually sell an industrial distribution business. Over the last 6 years, I have consulted with manufacturing companies, B2B businesses, and technology firms.
The work I am paid best to do is operational optimization that improves financial performance. I spent 20 years learning it.
I love the creator community. Coaching solopreneurs has become some of the most rewarding work I do. I value the audience, the training, and the relationships I have built. The money I left on the table came from confusing the skill I had recently learned to distribute with the expertise I had already earned.
I could have tested an offer when I had 500 connections. I could have taken a specific problem and a proposed piece of work to people in my professional network. Their responses would have given me something to examine while I continued learning to publish.
Instead, I spent 18 months leaving the offer unresolved.
For someone with a long career, the work worth examining may be the work that feels most ordinary. Scoping a consulting engagement was familiar to me because I had done it repeatedly. Understanding a company’s operating problems was familiar for the same reason.
That familiarity made it easier to overlook the work when I was thinking about what to sell online.
Start With The Work You Have Already Done and Been Paid For
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