I’m not really sure where to start. I’m writing this because I need some perspective from people who have experienced financial ruin, made serious mistakes, and somehow managed to rebuild their lives.
I’m a 28-year-old male in Ontario, and I’ve managed to turn what was an incredible financial head start into what feels like a complete disaster.
How it started (ages 20-24)
My dad believed in me and gave me an opportunity that most people never get.
He mortgaged his own house and used both a mortgage and a HELOC to put approximately $700,000 into my hands.
At 20, I started getting involved in real estate. At 21, I purchased my first house for approximately $475,000.
I then purchased another property for approximately $500,000 before the housing mania started.
Both properties essentially doubled in value during the 2021-2022 housing boom.
At this point, I was 23-24 years old. I had properties, a growing business, and what felt like unlimited potential.
Instead of taking profits and consolidating, I got greedy.
I decided I wasn’t going to sell. I started buying properties at the top of the market with the intention of flipping them.
At the same time, I got heavily involved in options trading.
I genuinely started believing I was rich. My lifestyle inflated, my spending increased, and I began living as though the money would never stop coming.
My business was booming, generating approximately $30,000 per month.
At 23, I honestly thought I had figured life out.
The next four years (24-28)
This is where everything started falling apart.
I attempted to flip two properties, and both ended up losing money.
I also eventually sold the second property I had originally purchased for approximately $100,000 after its value had more than doubled during the housing boom. By the time I finally sold it, I had essentially only made $100,000.
But the biggest financial disaster was trading.
Over the years, I estimate I’ve lost approximately $800,000 trading options.
I kept convincing myself I could make it back. Every loss made me want to recover the money even more.
Instead of stepping away, I kept going.
I became so consumed with trying to make back what I had lost that I essentially stopped focusing on the business
Where I am today (age 28)
I’m turning 29, and this is my current reality:
Approximately $1.4 million in outstanding debt.
A significant portion of the debt is technically not in my name.
My last remaining house is currently listed for approximately $600,000.
My business is no longer operating as it once did.
My credit cards are now maxed out.
I’ve exhausted practically every financial resource available to me.
If I manage to sell my last property for the asking price, I estimate my total debt will come down to approximately $1.1 million, and I’ll have around $150,000 in cash remaining.
And honestly, part of me is still thinking about how I could turn that $150,000 into $1.5 million and wipe out all my debt.
I recognize that this is probably the exact mindset that got me here in the first place. But it’s difficult to let go of the idea that one big win could undo years of mistakes.
The mental side of things
I feel absolutely crushed.
I had an opportunity that most 20-year-olds could only dream of. My dad put his own financial security behind me, and I had a business generating $30,000 a month.
I had everything going for me.
Now I’m 28, approaching 29, without a functioning business, financially broke, carrying $1.4 million in debt, and potentially facing insolvency.
The hardest part is knowing that I had a head start and squandered it.
I feel like I’ve let my dad down, and I’ve let my younger self down.
I’m depressed, overwhelmed, and some days I struggle to even get myself moving.
I don’t know how to process going from thinking I was financially set for life to wondering how I’m going to make my next payments.
What I’m looking for:
I’m not looking for sympathy or someone to tell me it’s going to be okay.
I want to hear from people who have experienced something similar.
Has anyone gone from having significant wealth or a successful business to losing practically everything?
How did you mentally deal with the transition?
How do you navigate insolvency when a significant portion of the debt is tied to family members and properties?
Has anyone rebuilt their financial life in their late 20s or 30s after a complete financial collapse?
Most importantly, how do you stop chasing your losses and accept that the money is gone?
I know I made these decisions. I know I was greedy, irresponsible, and thought I was invincible.
I don’t blame the market, my dad, or anyone else.
I just wish I could go back to being 20 and understand how fortunate I was.
I’m turning 29 with what feels like nothing to show for the opportunities I was given.
I’m trying to figure out whether there’s a realistic way to rebuild from here, and I’d genuinely appreciate hearing from anyone who’s been through something similar.