How do you overcome fear and self-doubt after an initial success?

- Backstory -

I’m a solo entrepreneur who hit a relative home run once before - I created an eBay application that generated several million dollars for me over a decade ago. I realize that's peanuts for some people around here, but for me it's huge. However, I attribute much of the success I had to a special scenario.

eBay had an app store at the time and I was one of the last developers to get in before they closed it to new developers. For eight years, my cohorts and I bathed in a steady stream of leads. Once eBay eventually shuttered their app store, I quickly migrated my users to my own site (as eBay had a hosted app model similar to Shopify), since then, it hasn't grown at all.

- Fear -

During my app's time in the eBay app store, I witnessed small-scale operations, much like my own, blow right past me and grow substantially (3DSellers, Inkfrog, Outright). While these companies had more employees than me, I don't believe that was the critical factor in their success. Rather, their founders exhibited a level of fearlessness and focus that I lacked.

Having crafted an app in three months that out-earned my entire previous decade of employment was a shock to my system. I found myself constantly worrying about losing what I had built, instead of capitalizing on it. Ultimately, this a failure—not financially, but in terms of unrealized potential.

Another issue I grappled with was the safety net the eBay app store provided. The limited competition was incredible, but it left me feeling ill-prepared to attract users independently.

Recently, three successful founders I know (Mike Flynn and Oisin O’Connor from ReCharge, and Ben Curren from Outright) recommended a book called “The Startup Owner's Manual” by Steve Blank and Bob Dorf. I initially skimmed it but found it more academic than other reads like 'Traction' or 'ReWork'. However, hearing it mentioned at a conference by the ReCharge duo compelled me to look deeper.

The book emphasizes the importance of customer interaction, outlining how to create a business plan using the Business Model Canvas. It advises on testing various business dimensions through customer interaction—a process I am beginning to undertake for a new product I'm developing.

The product is a browser extension that records user interactions. While similar products exist, I aim to differentiate mine by adding elements of gamification and fun. I think "fun" is increasingly becoming a differentiator. As of now, I have a few Figma prototypes and some working code, and I'm in the early stages of pitching this to potential users.

Here’s an early screenshot of the working code - it’s changed a bunch since then

https://preview.redd.it/907g98vqf77b1.png?width=2430&format=png&auto=webp&v=enabled&s=8a97f47e156ee4ddeb0d554922df4af729a39ba6

If you're interested in helping me refine this product and willing to serve as what the Startup Owner's Manual refers to as an “Earlyvangelist”— someone eager to try early-stage software and help shape its future—please e-mail at john@demo.fun to arrange a Zoom call (or if you would rather stick to e-mail that's fine). Your insights would be greatly appreciated. I also have a contact form on https://www.demo.fun