Zaire Allen

What's it like to make millions young just to end up losing it all and being in -$80,000+ debt before your 20s is over?

Well, for starters. I didn't piss it all away on debauchery, overly expensive vices or exotic Lamborghini's.

Before I continue, it's updating on where life's now at today. Currently, I work in a coffee shop clocking around 48 working hours a week and another 15 hours commuting. I make around $23 per hour.

Do I enjoy this? God no. I miss being able to eat steaks at the finest restaurants on a whim. The thrill of driving fast cars. Better yet, the sleep you get at night knowing money problems weren't a burden. I went from having a team of 8 colleagues, and over a hundred thousand in the bank to being chased by debt collectors.

It all started with trying to help get people employed. I built an online design school called Love Circular from the ground up. We taught 1,300+ people UX/Product Design and a few other courses in other fields. We helped launch and place around 400 of those designers we taught who now earn $30m+ in salaries.

My professional skillset is a bit of a mess at this stage after 5 years of being a 'entrepreneur'. I went from a full-time growth-minded Designer to a well-experienced generalist quite quickly. This is great for growing companies and being at some startups, but detrimental now that I'm trying to get into building a career again. I'm skilled enough to get many different jobs done to a high enough level to drive revenue, customer retention and user satisfaction, but not enough to be the specialist who nurtures the product/service further... at least on paper.

For the past 4 months, I've tried to land a career job in Product Design, Operations and Sales. I've spoken with recruiters and had numerous interviews. It's becoming clear that I'm a difficult hire for many companies. Not because of competence, far from it in most cases. It's the narrative around me. "She also didn't understand why you would be looking ie with Love Circular revenue etc" – feedback from a recruiter.

The thought of "has he considered starting a new business?" has probably crossed your mind by this point. Yes, many. Coaching designers to build service businesses was the most fruitful and filling. I also tried a small design agency for MVP projects; just didn't enjoy the work enough. And, after learning to code, an AI note taker was a fun option.

I've thought about bootstrapping, and raising venture capital. I've spoke to a few different people. Honestly, I couldn't tell you where the fuck my mind wants to be on the whole building a business path. I know I love solving real big problems for people/companies, I'm just not sure how. Building businesses when you're living and financial situation is precarious is insane. You end up needing every idea you have to be the "right one."

I left the UK at the beginning of 2024, to move to the US (New York City). Finding my feet is still a work-in-progress 18 months on. Many days I ask myself how ridiculous the idea of me seeking a new life was. Delusion maybe? I ask myself how far can this go, how many months of financial instability can I cheat my way through. Two close friend's have called me a 'cockroach' and quite frankly, they might be onto something.

Life's become one masochistic game of how resilient can I be?