Permissionless Apprentice — Ryan Doyle

Guest author: Ryan Doyle.

I grew up on a crop farm in the Finger Lakes of New York. When I was eighteen, I had the opportunity to go to school in Los Angeles. For the first time since my great grandmother came here from Ireland, a Doyle left the “middle finger” of NY.

For four years, I studied “business.” For someone used to working with their hands, it was an uncomfortable amount of theory. Outside of my classes, I was tinkering. Projects like a bitcoin brokerage, seeking a patent for a garden tool, and a few ecommerce shops became my bridge between theory and action.

Quickly, building became my passion. As I graduated, I joined a software startup in Palo Alto to smile-and-dial as an entry-level sales person. I figured I’d see how these companies were built from the inside out so I could emulate it someday.

Hustle and elbow grease took me from that role, to another startup in NYC, where I helped build the sales team. I went from phone jockey to deal-closer. On my nights and weekends, I was teaching myself to code.


One of those nights, I found Visualize Value on Twitter. The simple theories resonated with my action-oriented mindset. In particular, the idea of a Permissionless Apprenticeship. (link to tweet thread)

This was something I was already doing in sales. I’d see a company that might be worth a few million dollars to the company. I’d live their brand for a few days, experiencing everything I could. Then I’d compile it and send it to the highest executive I could find, showing the gap we could fill.

It had the highest return on time of anything I did.

In the VV community of designers and makers, I accidentally found out that this was valued by anybody in business, not just Fortune 500 companies. I started doing “Free Sales Advice Friday,” and business owners would share what they were working on. I would reply with scrappy tactics to go out and find new customers, specifically for their business.

"Some of the best help I've received online, thank you." — Jordan Godbey

"That is superb advice." — Andy Whyte

"Ryan, this thread is gold!" — Ben Ford

I didn’t think too much of the feedback and kept working on my sales job. But I knew, mentally and emotionally, I was ready to make the leap into something of my own. I could code. I could sell. The pandemic provided the perfect reason to hide away for a year and hustle, nobody was hanging out without me anyhow.

In August, I quit my job, moved back to the farm to extend my runway, and committed myself to building. I felt like I had the skills I needed. The community was there through my sales work. I hadn’t realized it yet, but the community was there through Visualize Value as well.

I hoped salespeople would care about what I was building. As I applied my sales advice to my own software project, I found that more builders cared about how I approached sales. In months of Free Sales Advice Fridays, I advised 100+ business owners and explored so many different angles they could take.

There was already sales advice out on the internet. But the message didn’t matter to these people, the medium did. And I was the medium. To tap into that I built a small guide on pre-selling your product to customers and tested the offer of a premium newsletter. Then this happened:

On day 1, I hit $170 MRR. More revenue than I was making from my software project. Almost entirely profit. From what was already in my head. It was astonishing to me, that something so innate to me was worthy of an individual’s money.

By sharing that innate knowledge through Free Sales Advice Friday, I was really embodying the permissionless apprenticeship. Every week I was able to hone my message in a zero-stakes, zero-permission environment.

If I hadn’t sought out ways to provide free value, I wouldn’t have realize what people would pay me for. By the time I discovered what people wanted to pay for, I had built up enough “brand equity” for early adopters to trust me.

I’m still building my software projects. But my early adopters for my sales guides will allow me to do so with an audience who will test and support me, while paying me for the opportunity to do so.

I still do Free Sales Advice Fridays and stay active in the Visualize Value Community. When you join, look out for the weekly post in #general. Looking forward to giving you sales advice, too :)



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