How I bootstrapped my startup in just 2 years to 16 million users

Within six months, I bootstrapped my startup to 1.4 million users. Two years later, our software is used by 16 million people worldwide

Venture capitalists scoffed when I said I was self-funding (bootstrapping) my new artificial intelligence startup. Other industry veterans I spoke with said competing without a fair whack of VC dollars was a fool’s errand.

I’d already gone the VC route with my previous startup, ChatterQuant, so I knew what it entailed: less control, lots of fine print, and a skyscraper of expectations.

We launched our startup because we noticed a problem: current AI solutions flagging real human writer’s work as AI-generated. Students were accused of using ChatGPT on their assignments, and writers were fired because their work seemed ‘too AI-generated.’

The irony was palpable. People were punished for the perception of using artificial intelligence. Someone needed to level the playing field.

The first step was market validation. First, we reached out to people online who were complaining about AI detectors. There were two types of initial customers:

1. People whose original work was frequently flagged by detectors
2. People who wanted to use AI to create content identical to human content.

Early on, people told us they’d use our product but wouldn’t pay for it. The truth is, if someone needs a product badly enough, they’re willing to pay for it – whether they admit it or not. Talking to people is great, and it’s how we met one of our first founders and other talented people who contributed value to the company.

We encountered Henry Cooper, an IT and cyber security specialist from New Zealand. He heard about Undetectable AI, checked our website, noticed a few vulnerabilities, and let us know.

We rewarded him by granting him access to our API, which he’s now using to research cybersecurity applications, and he updates us regularly.

Money doesn’t always make success

The keys to properly bootstrapping are great people with obsessive resourcefulness and investing time where money lacks.

My initial $1,500 investment wouldn’t impress venture capitalists, but it forced a discipline that VC-backed startups often miss.

Early on we mastered clever workarounds and quick deployments with a minimal tech stack that was functional and effective. Initially, our product design wasn’t pretty but it worked.

Well-funded competitors poured funds into eye-catching interfaces. We delivered raw value that solved an immediate problem for our users and saved them time. They forgave us for our whacky early web design.

Our MVP (minimal viable product) strategy was brutally simple: Does this feature solve the user’s problem
directly? If not, it waits.

The A team

Fantastic founders and first hires are the foundation of our company. I had a knack for sales, my CTO a brain for code, and our CCO a public relations polymath with a penchant for wielding words and forging brands.

When you’re bootstrapping, having founders and early team members willing to invest excessive dedication is necessary – not preferable. You need people willing to fix things at midnight, not because their contract requires it, nor due to force, but because they’re building something they believe in.

When you’re just launching, look for the lowest-cost ways to market your product. We used cold email, social media outreach, public relations, and partnered with commission-based affiliates to drive early growth for low costs.

Search engine optimization is another low-cost strategy we used, and social media has been and still is a huge driver of engagement for us. At one point, we had 1000 TikTok videos about our software being made every month.

Eleven months into our startup, four million people were using our product. We were making money, but the growth greatly strained our minimalist tech stack. It was time to scale further because we were profitable and needed to sustain our continual growth.

Expanding independently

The transition to stronger, scalable systems meant painful rewrites and sleepless nights. Big tech companies threw teams of engineers at these problems, and we threw ourselves into learning whatever skills the moment demanded.

My non-technical co-founder, Devan Leos, and I dedicated days, weeks, and sleepless nights to researching AI model improvements and submitting data for bug fixes and patches. We had calls every day.

One thing bootstrapping protected us from was investor pressure to enter enterprise markets early on. Enterprise contracts are more significant but have longer sales cycles and slower growth.

If we had initially focused heavily on enterprise markets, we wouldn’t have the number of users we do today.

Staying independent allowed us to build a product users wanted rather than one that looked best in quarterly investor updates. Around the 12-month mark, we started doing enterprise deals. A competitive product is key; having a massive user base proves your product works.

Bootstrapping isn’t easy, but if executed properly, a bigger win – not just a financial strategy or status. For us, it’s been about maintaining our vision and the independence that drew us all to entrepreneurship in the first place. Each milestone feels earned rather than purchased.

Ironically, by refusing early investment, we’ve created something investors now actively pursue. The difference is that we negotiate from strength, not necessity or desperation.

Make no mistake, sometimes taking venture capital is necessary, and I’m not against VC-backing – but the success of our company proves that bootstrapping to profitability is possible. You can always take a venture capital injection later, but often times once you do, there’s no going back to being self-funded.

At the time of writing, our company Undetectable AI has over 16 million users and has generated millions of dollars. The key to that growth was dedicated founders, radically passionate early hires, and cost-effective marketing and advertising solutions that drove growth without putting us in debt.

In a world obsessed with unicorns and cash-backed ventures, sometimes the most radical and right choice is to build a sustainable business that just delivers what it promises. The key of course, is doing it with the right people.