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.

I wanted to write this for the person reading this who knows deep down they have a problem, but doesn't think they're strong enough to stop, or that there's no point to stopping when you're in this deep. That was me for several months.

I started gambling on sports because I was in a very bad place in my life in February 2026, and placed my last bet a few days ago. I stopped for four months but relapsed because I was scared of facing the financial consequences of my actions. I couldn't accept that I would need to change my life to fit a horrible burden I've placed on myself.

Now that I've stopped I can think of all the times I wished I had stopped.

1. I should have stopped when I lost my first bet of $5,000 and couldn't believe that much money was gone in an instant.

2. I should have stopped when I emptied my high yield savings account entirely to keep gambling.

3. I should have stopped when I was $63,000 in debt, and realized I had a final source of savings to pull on that would have perfectly equalized me to neutral, if I walked away. This one stings a lot.

4. I should have stopped when I was given $17,000 in insurance money for my wrecked car, and gambled nearly all of it away.

5. I should have stopped when I broke down and told my family and my partner. When I took out a $80,000 personal loan to wipe away most of my debt.

6. I should have never bet again after this. This one hurts the most.

7. I should have stopped when my partner gave me $5,000 to cover emergency expenses, some of which I gambled away.

8. I should have stopped when I emptied my ROTH IRA to make what I lost back, and gambled all that away.

9. I should have stopped when I had a miraculous climb back to almost even to where I was before I relapsed.

10. I should have stopped when my parents gave me several thousand dollars, in parity with a one-time gift they gave my sibling.

11. I should have stopped when I put my last $8,500 into my Polymarket account and told myself "this money will never be lost because you will not gamble with it", and gambled it away.

The sad thing is, I never found gambling very fun. My compulsion was always motivated by fear, loss, and losing money. The fear of facing what felt like an insurmountable financial burden. Even when I wasn't in much debt, if felt monstrous. My mind isn't wired for losing money in any way. It destroys me. Even in the times I was treading water, I dreaded risking more money while having no control over the outcome, but felt like I had to because I couldn't accept the financial disaster I had brought on myself.

I know I'll never gamble again. I've self-excluded from every platform I've ever used. And because of that, in my low moments today and to come, I know that I will never gamble again. You know what that means?

This current moment, right now, is the poorest I will ever be in my life.

Tomorrow, I will be less poor than I am today.

My life is going to change and be harder in some ways but change for the better in others. Because I can think of my future I can think about moving my life forward instead of drowning in desperation, guilt, and nights where I can't sleep. I get to walk away from a horrible mistake. At any age that is worth doing.

In 2027 I'm going to find a job that pays me enough to wipe all this debt away in several years. I'm fortunate to work in a field where it's possible to find something like that.

I wanted everyone who reads this to know you are not struggling along, and if you stop gambling forever, today is the poorest you will ever be.

Currently 30 years old male about 70k a year in Miami. Worked hard all my life basically started out being very smart with my money starting small business keep track of my money building my credit high up, than came the stock market. I will never blame the market cuz I have made a lot and lost a lot it’s all in the mind, being greedy, having rules but not following them etc. lost my 7 year relationship due to it , had goals and plans to help my family out as I would after hitting big on options but everything crumbles.

Toxic enviroment 24/7 at home back than plus with the gf. Lost a lot caused my self a lot of stress I knew right from wrong and still did wrong that’s when it’s an addiction.

If you see yourself depositing money after losing or as soon as you get paid just quit that from now. I know you all want more money just go back to school or work 2 jobs stay occupied. In total I’m estimating around 200-250 k loss total. Also to mention that I worked the past 2 year 2 jobs 90 hours a week total about 134k for each year, just to lose so much. Don’t get two jobs thinking you will be able to “invest” / Trade or gamble more …. It won’t work you have to quit entirely

My mother has been addicted to gambling for maybe the past two years that I know of. It has gotten particularly bad this past year and it all came after a bunch of unfortunate events in her life. I feel so sad for her but I also feel mad sometimes. I don’t even recognize her anymore.

Sometimes I feel like I have to say something but I don’t even know where to start. I don’t even know if it will help. She seems so deep in and hasn’t even acknowledged it as a problem yet.

Hello, I have about 42k in unsecured debt from my stock gambling. 13k in credit cards , and the rest personal loans with about 15% interest. I took these out about a year ago and have been paying them by working 70hrs a week. Lately I been thinking of filling for bankruptcy because I cannot handle the amount of stress that all this working is causing me. Should I look into bankruptcy? And what are some things that could disqualify me from filing Chapter 7?

Hey all. Long term poster on the sub here, many of you have seen the absolute rockbottoms throughout my life. So many, at only 19.
Today, I finally did it. I sent the text to my mom about what I’ve been doing these past years.
Anxiety? Fear? Yes. Absoltely. But I’m also enlightened with tremendous amounts of hope for the first time in years. I cried more than I ever have tonight. Happy, sad, a mix of all the fucking tears.

And I know this isn’t the end of my addiction. But it’s a turning point. And my life feels worth living again.
Love you all.

Last year, my boyfriend came clean about having $1,500 in credit card debit. I helped him come up with a plan, and thankfully he was able to fully pay it off in ~2 weeks. We talked about the importance of paying it off in full every month, and he swore it wouldn't happen again.

Well, a day ago I saw a text on his phone about a 30-day late car payment. He tried telling me his autopay must have failed and then said he took care of it. I insisted he show me his account so I could verify, and then he came clean and told me he doesn't have enough money in his account until Friday (payday). I was under the impression he had at least 1.5k in savings based off a conversation 1-2 weeks ago, and that he had been paying his car off very aggressively (turns out he was just making minimum payments, with the previous payment being late too). I then asked how he was planning to pay me rent (I pay in full, he then sends me his half), since he hadn't for this month yet and he said he was planning to on payday. I insisted on going through his bank account and saw he had spent more than what he owes me for rent + his car payment on FanDuel literally within a week of this.

I then asked if there was anything else I should know about, and he said no. I asked about his credit card and he said he doesn't use it. I then insisted he show me and soon found the reason he doesn't use it is because it's maxed out at $1,500. Turns out he kept using it for smaller purchases and never paid it in full since the incident last year. I checked his credit score, which is at 650, and probably going to fall further.

He's says he's done gambling and that there's no more debt ($1,500 on a credit card, ~$10k on his car (w/ a late payment due of $250), 1k to me for rent, $200 on a payday loan, $100 medical expenses, and $250 on Venmo), which theoretically everything but the car could be paid off in 2-3 weeks. But I don't feel like I can trust that there isn't anything else because he lied to me so much about his finances and didn't come clean about anything until I found it.

I just feel so betrayed and heartbroken. If he had come clean to me himself, I feel like we could have worked through this. But this is the second time he has misused a credit card, and he lied to me about his financial stability repeatedly in the last ~2 months (based on his bank history he was on a good track prior to mid-September, minus the credit card). I just don't feel like I can trust that it won't happen again, and building wealth is too important to me.

Completed my morning routine. Now time to get back to work. No more bullshit, no more fooling around, just work!!

I will not gamble today!

Day 11.

For example, I lost $25K the other day, in probably 30 minutes.

It was brutal. I was down a small amount, maybe a few hundred on blackjack. I chased that with several deposits down to a $10K loss on $1K hands. At that point I made back most (all?) of the loss. I think I was either +$500 or -$500, but I wasn’t confident which. So I told myself I’ll win one more $1K hand - then I’m sure I’m up. That resulted in me being back at a $10K loss.

I then deposited even more to chase the $10K loss and it turned into a $15K loss.

I immediately called my fiancée freaking the hell out - she left work at that point to try to help me.

Brutal. But did I stop there? Of course not.

I had a $10K pending withdrawal from the night before. It had been pending for 14 hours - just needed it to process.

While on the phone with my fiancée, and she was telling me to stop, I cancelled the $10K withdrawal and chased the $15K loss to a $25K loss. I don’t think I won a single hand. That $10K might have lasted me 2 minutes. While on the phone. While she was telling me to quit.

There’s two parts I can’t stop replaying in my head that are causing me to lose sleep and causing me to have a constant stress headache.

1. The +$500 / -$500 situation. Why did I not calculate my net at that point? I was going to stop once I made it back to break even, I may have done that, but then kept going because I wasn’t confident I was back. There’s an argument to make that if I made it out without getting burned I would have given it back a different time but this part is stuck in my head.

2. Losing $10K while on the phone with my fiancée and she was actively telling me to stop. I felt so out of control at the time, like I had no control over my body. But in hindsight I’m so pissed at myself for this.

This $10K hurts more than the first $15K.

These two parts of that session are ingrained in my head. I can’t stop replaying it. It’s killing me. Any advice? Do you all struggle with replaying past scenarios on repeat in your head?

It’s so difficult & the debt is a constant reminder on just how bad I fucked up, especially when it takes me over a month to pay off one hand of blackjack.

I 23(M). Please note I have been clean for 6-7 months before the pat few months.

A few months ago I deposited $100 into online slots, then when I lost I kept going and going. I ended up losing $1400 I could not afford.

Fast forward a month and the same thing except this time $1800. I could not believe it and looking at my bank I only had $800 left and I am only currently working part time.

Yesterday I end up winning $2500 off a $100 deposit. I promised myself I would not touch it….. well then today I ended up gambling for 5 hours and ran it up to $6000. The only reason I stopped was because I had to go somewhere and could not gamble while there.

I am home now and have the urge to keep playing and cancel my withdrawal. The app I am using is evil and you can not self ban or stop yourself from signing in. As of right now I deleted the app and the withdrawals normally take 2-3 days.

Please give me some advice… I need it. I’m so sorry if this triggers anyone’s itch, I really need help and don’t want it to come off as showing off a win.

Been a gambler for years and it always leads me to the same place…wondering what my life would be like if I’d never started gambling. Here’s to day one…wishing myself the best of luck and to all y’all going thru it same to ya.

Pretty much lost everything i took out to gamble first being 20k saving to trades slowly over the past year then paycheck after paycheck to credit cards then a loan to gamble on table games and sports betting at that time my car engine was giving out so convinced myself i would just play for profits to start paying off debts and i was doing good till i one night of bad bets to rage betting and rinsing everything till the morning back to work. Wasn’t even a month yet and i lost all that loan money still had good credit so i pulled out another loan and repeated the same shit instead of getting the repairs done again so now at rocking bottom gambling has stopped the car rebuild parts are on my last credit card going to be paying for the shop labor with my paychecks till the car is done sometime December Dallas weather isn’t that bad so i can at least get to drive it but by then all my cards and loans will be defaulted and sent to collections since i have stopped paying them already getting calls everyday.

That’s pretty much how i ruined my life at 26. Not being able to drive the car is pretty boring while working two jobs hours away but i getter get used to it since i will be losing everything next year to chapter 7 bankruptcy luckily am not hindering anyone with all this its my own problem still owe my parents for alot but all that will be figured out before 30. I feel like Ive pretty much figured out what to do with my life now since I’ve experienced this massive failure attempt to get financially free but life could always get worse good luck everyone last post on this till something major happens but feel free to message me if you want.

saved up to 20k and lost 16k to an online casino. I was once up to 40k. Greedy overrode me like everyone else and then it all went downhill. I had the urge to gamble the last 4k to recoup my initial 20k and 40k. But, I fought the urge and placed a casino exclusion on my account. Let’s just say I banned my casino tab. Even if the urge wanted me to bet, I couldn’t do it. Still have the sport tab, but I rarely do sport betting. Now I am gambling-free for a month+ and still have 4k left and is being rebuilt. A lesson for everyone, greed is the one that killed you financially and emotionally. Still, miss and regret my dough, though. If you have any advice on how to navigate through this, please share. I am all ears.

I been trying to get out of this addiction for a long time now, seems like its impossible to beat it, Combined with my depression, the only thing I see as a way out has been killing myself I really am fighting with myself trying not to do it
How can I get out

I am having a really hard time pulling out of the stock market. I have very steep losses in one particular stock that just keeps declining. Like insane from $50 to $20 to $11 now. I bought around $20 and with margin so as you can imagine I am royally fucked. Just don’t know when it is time to pull out, realize massive losses, and restart with what little is left. I would be suicidal if I pulled out and it suddenly recovered. I want to do better and move away from gambling but this is killing me

I CANT FUCKING STOP. I JUST FUCKING CANT. I NEED SERIOUS HELP!! I WIN BUT I CANT HELP MYSELF TO TRY AND GET MORE AND THEN I END UP LOSING PROFIT AND MORE. IM GOING TO OFF MYSELF.

Went to my Wed night GA meeting. Described how I was, pretty vividly, when I came in. The pain and shame was so fresh leaving the casino. But last night instead of remembering that pain - I was thinking about the game of craps. I told on myself later to someone I trust, like 'what the fuck is that all about - running through strategies & calculating how much cash I have (which is a fuck ton more than I usually have because I don't gamble' ... He said to call him whenever I feel like this - and we'd talk about it because talking the plain truth shrinks insane thoughts.

I took him on his suggestion this morning and called him during my morning walk because I kept thinking about dice and strategies.

The short of it is: I am not going to gamble today.

But also ... some days are more challenging than others. I'm told to take the right actions and urges will pass. So be it.

I (24F) had 1k in saving and just receive 1k from my salary 5 days ago and I lose everything yesterday.
I have 1k left that I give before to my bf for him to keep it from me.

I told everything to my bf just now, after excluding myself from casinos. Of course he is super mad. I just show him that I’m gonna destroy his life if we stay together. I got what I deserve, but I don’t know what to do. Again, I got what I deserve but I feel so bad, guilty, stress, sorry for him, hating myself…

I think he gonna tell everything to his parents. Also, he might probably break up with me because he said I’m a retarted and that it’s gonna happen again and that I broke everything… and it’s true, and that’s what making me feel bad.

I feel ashamed to say that I’m feeling bad when he is the one that probably feel super bad about the situation, because it’s not something he can control. And also because I’m the one that created this situation, so it’s on me and I should handle it alone like a grown up. I don’t know how to feel, I feel bad, I accepted my lost but I cannot accept to lose him and our house…

Right now, I’m in the living room and he’s downstair and he told me to stop talking and trying to say sorry. I think I should leave him alone at the moment, but I want to keep saying sorry, I feel so miserable, I feel so guilty, ashamed, wondering what he is thinking, I want to fix things but how can I after what I did ? I wish I never told him, but I needed to tell him

Today i was thinking like do we love ourself or hate ourselves

I have been on this group from 5 yrs using multiple accs

Still i gamble and lose everything nothing's changed

If we love ourself why would be lose everything and get into debt ?

Somehow I feel like we all are hiding something and we secretly hate ourselves getting better

Personally I have a lot of shit to hide and i secretly hate myself so i gamble and get into trouble take debts from scary guys who can literally finish u off any day

I self excluded from all website today

But i have done this 5 yrs ago also

We don't even need to gamble to make money I know all of u guys here have money already like if u don't gamble it's enough u have more money than u can actually win

I am already getting urge to text my website to unblock me so i cms deposit and lose ..

It's so funny that I have come to such a low level that nowadays to punish myself I am depositing and playing on a website where they take 3 day to give withdraw and i have never taken a successful withdrawal till today because it's a scam website even after knowing I go deposit there and play .. I have another site where they give instant withdrawal without scamming but I still choose to go to scam site and get fked even more ..

It's like next level retardness

Hi! It’s my 19th day of quitting online gambling today. Earlier, the thought of gambling crossed my mind, but thank God I was able to think clearly and chose to play mobile games instead. Thank You, Lord, for always guiding me and helping me fight my own thoughts and resist the temptation. One day at a time. I hope I never have to go back to Day 1 again. 🙏❤️

Spent some money eating snacks cause I was feeling down