Joel Always one syllable, sometimes "@jayroh"

Challenges in Solopreneurship

14 Nov 2023

A man, alone, looking out into the distance, down a very clear and empty road.
An illustration of what solo entrepreneurship, in retrospect, would feel like.

Nine years ago, I embarked on a journey with Shubox, a solution to simplify uploading to, and working with, Amazon’s S3. This venture not only evolved along with my career but offered rich lessons worth sharing. In addition to my day job, I work on it my nights and weekends. This is some background information for the basis of a story I’ve participated and observed throughout my career.

The story looks a little like:

  1. You move on from full-time software engineering employment.
  2. Hang a shingle out your door, advertising your new, independent contracting/consulting business.
  3. Work with great clients, get paid (well). Make ends meet.
  4. Leave enough time for yourself to build your own product, perhaps launch your own SaaS.
  5. …?
  6. Make enough money off your SaaS to devote 100% of your time to that product.

I’ve done this and currently remain at step #5. I’ve known many colleagues and friends who’ve also done this. The ratio of people who get to step 5 and never manage to see step 6 is, most likely, in the 98% range[2]. It should go without saying that this particular hustle is way way more difficult than we would want or expect. I guess if it were different, we’d have every tech-hub over-populated by wealthy, bootstrapped, side-hustle-preneurs.

Would I discourage anyone from following this path? No, absolutely not. The likelihood they catch the right wave is slim, but the probability they learn an extraordinary amount is high. If learning is a goal, then you are inherently set up to succeed. With that, here are some of the things I’ve learned along the way while building Shubox.

Being “Solo”

I started Shubox because I saw a problem (uploading files from your website to S3) more than several times that grew to an “itch” that compelled me to “scratch”. Why was there nothing better? Surely there was something to fill my requirements that took less time to wire together? After building the POC I was convinced I was onto something. This was now doing what I wanted!

Building something you are so certain the world needs - that feeling is intoxicating. “The world needs this! I can’t believe this doesn’t exist! It’ll sell itself!” …Maybe? Coding it is just the beginning. A semi-functional POC will get you only so far. What about design? Marketing? Product management? Social engagement? User research?

In addition to being a strong engineer, if you are equally skilled in any of the above, you are fortunate. I’ll tell you what? I am not. So let’s talk about being “solo”. When it’s just you, you are all of those functions. If you can’t, or don’t want to, fake it, then you’re going to pay for it. Literally. Even so, that is a singular transaction. Those partners will only be around for so long. What happens then?

Solo. Alone. No one to bounce ideas off of. No one to share in defining strategy. No one to lean on, or hold you accountable. No one to review your work. No one to tell you when something is a bad idea.

It’s lonely. The experience of trying to build Shubox has been lonely. If I could go back and change something, I wouldn’t have gone down this road without a partner, and will most likely never do that again[2].

Know Yourself

How well do you know yourself? I mean, really know yourself? Have you done the work to inspect the depths of your strenghts and weaknesses? I find self-awareness to be an incredibly underrated trait. What are your flaws? Are you clear on what motivates you? What discourages you? What you’re terrified of, but would never in a million years admit to? You may not be familiar with these unknown unknowns yet , but putting yourself through the process of starting and running a business will surface these, over time, almost certainly.

For example, I now know I have a distaste for marketing me, putting myself “out there”. I am modest to a fault and would much rather play hype-man for friends, and colleagues. Building in the open? Why would anyone care? I’m just some random guy!

I also know I’d rather work on “this technical thing”, than pour effort and cycles into the marketing, promotion, selling. It’s so much easier to be neck deep in code building something.

And - this one’s tough - do you know you can never really fail if you don’t really try? Not gonna lie, this one hurts. It’s taken me a long time to confront this in particular. There’s a voice in the depths of the back of my brain, haunting me: “If I don’t allow this get big, then will I ever truly fail?” It’s a process to recognize and confront those voices, one truth at a time.


As mentioned previously, the lack of accountability remains one of the more profoundly affecting missing pieces of the puzzle. When there’s no one to report to, where do you go? Who is there to keep you honest? Over the years upon reflection, the biggest challenges I’ve managed to overcome had accountability as a central tenant, providing me a ballast to keep my ship upright, to stay on course. If you are accountable to no one, then you are accountable to no one. Find that person, those people, even if they don’t really care! Email them! Say “I’m going to do this”, then follow up. If you do not accomplish what you set out to do, be honest, be vulnerable, know yourself, and truly know why you did or did not do what you said you would.


This post has been living in my head for months while I work through how I’m moving forward. My publishing this, in and of itself, is a large part of the process where I come to grips with those fears, uncertainties, hard truths, while allowing myself to feel uncomfortable. I am at peace knowing that failure isn’t truly failure if I’ve set out on that journey, did my best, learned something, and can look back with no regrets.

So, here we are!

Stay tuned.

More to come.


  1. Let’s pick an easy arbitrary number for that population of “smart friends who went solo-preneur” - 100 people. Of those 100 people I know 2 people - TWO! - who have made a thing, bootstrapped it, and had successful exits.
  2. What do you think of what I’m doing with Shubox? Any interest in talking about what the future holds for the product? Hit me up! (My email is easy to find, or on Mastodon I would still love to find that co-founder!

I'm working on something called!

Want to know more about it? (Answer: "Yes. I do") Check it out or sign up for my newsletter to receive news, announcements and other good bits!