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Cover image for Leaving stability to bootstrap a SaaS startup

Leaving stability to bootstrap a SaaS startup

Bob Bass
Founder of DebtOS & Full stack software engineer with a long history in alternative Finance
・4 min read

I have been with some people may have referred to as a bottom feeder in the past. Almost 10 years ago I opened a debt collection agency and it has been fairly stable and moderately successful but I sold it in November of 2019 so that I could pursue automation full-time.

I won't bore you with the details of how I ended up starting a small business automation agency but pivoting entirely to bootstrapping a startup aimed at creating cutting-edge software for the debt collection industry, but I will mention that over the years I created software for my agency using C# and .NET. Did that collection industry is notoriously 20 years behind the rest of the world when it comes to technology and I understand why that is.

Nobody likes to be involved with the debt collection industry. There are bad actors who give the industry a bad name, consumer lawsuits are rampant, laws are unclear, outdated, and ambiguous, but most importantly - nobody has seen the need to fix a system that many people won't acknowledge is broken.

If you are using dev.to, it's probably fair to assume that you are technologically inclined. That isn't the case for people in the debt collection world. Some agencies are processing $1 million monthly while using physical desk phones and Windows XP desktop. That isn't an exaggeration, it's not even an edge case.

There has been one platform that tried to create a serverless debt collection platform (as opposed to the current standard of having a physical server in your office), and this company clearly didn't have experience collecting delinquent accounts. The software is verbose and complicated. it's very hard to be productive when the people who design the software don't really understand the industry. I've also noticed that the debt collection industry is very resistant to change and when I release my app, I have my doubts about whether or not people are going to give it a shot even though I will feel confident making the claim that their revenue should increase significantly if they are using a well-organized, reliable, and streamlined platform design specifically for their day-to-day operations. I am building the software that I had always wished existed when I ran my agency.

When I started this project, I intended to build it using asp.net and my JavaScript skills were limited because I had spent most of my time and energy learning C#. I believe it was fortunate that my brother who was living in Silicon Valley at the time pushed me to dive into single-page applications with JavaScript. I brushed up on my JavaScript and learned to React pretty quickly but I didn't fall in love with it. I then built a small app with VueJS after watching The Honeypot.io documentary about Vue. It's fair to say that the MVC-like structure clicked with me in a way that I could only describe as 'common sense web design'.

At the time I'm writing this, I have put in over 2,000 hours coding this platform. I have hired a part-time developer in Nigeria who is incredibly hard-working and skilled considering he's fresh out of a boot camp, and I have even relied on him to teach me best practices for team-based version control which I never had to learn since I've always built solo projects.

At this point I've joined a startup accelerator and I really enjoy it. It helps keep me motivated and it keeps me hopeful about doors that it may open for me. All of this isn't without its downsides.

The money that I made selling my agency has been almost completely exhausted covering development expenses such as server hosting and developer commissions. I'm technically unemployed since I choose to focus on this startup which is not yet making money and I'm putting a lot of faith into the idea that I know this industry very intimately and that my platform will be groundbreaking enough that people will be interested in trying it out.

So - for better or worse, I've decided to sell my house to provide me with additional runway. The papers are signed and the sale will go through any day now so there's no turning back. I'm passionate about this and I believe in myself.

The worst case scenario is that the app crashes and burns which I don't think is incredibly likely but if that happens, at least I will have gained invaluable experience building out an entire CRM and automation platform from scratch. I've learned Node, Vue, Firebase/Firestore/Cloud Functions, MySQL architecture, custom API integration, and version control in a team setting.

Hypothetically, if this startup fails - I'm not leaving empty-handed. I've learned a valuable lesson about how passionate I am when it comes to software development and I would feel confident joining a remote team working with a similar stack. I've also proven to myself that I can learn and implement new skills quickly and efficiently. I'm much more competent than I was when I started down this path and I even find myself refactoring old code to prevent technical debt further ahead into the future.

There's a lot of uncertainty right now, much of it stems back to my inexperience with marketing and sales, but I'm determined to push on and I will be sure to update here once there are some meaningful developments. I would be lying if I said that I wasn't terrified, or if I didn't admit that I feel like I'm making reckless decisions.

Today is my 30th birthday and I don't have the stability that I've gotten so used to over the past decade because I'm risking quite a bit to pursue a dream which has long been on the back burner.

I hope that someone who may be interested in doing the same can possibly gain some perspective from my experience so far, likewise - I would be thrilled to get some feedback from anybody who's been through a major career pivot from something stable to something uncertain for the sake of passion.

As I've done for quite a long time now, I will continue to share my experiences as I go down this reckless path of entrepreneurship.

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