27, Been Grinding for 6 Years, Still Not at Consistent 10K/Month. What Am I Doing Wrong?

27, been grinding for 6 years, still cant crack consistent 10k/month. Honestly lost right now.

Before you start reading this, this is part advice but also part therapy session. Its actually the first time I have ever written down my thoughts and what I'm going through. So bear with me lol it's gonna be long, so sorry in advance. I just need to get this all out because right now my head is in scrambles and I genuinely don't know what to do anymore.

I'm 27, turning 28, living in Canada. Been trying to build businesses since I was about 22. I was the first person in my whole friend group to go the whole entrepreneur thing, and honestly, I think I motivated most of them to level up too. One of my boys landed his first six figure job partly because of the mindset shift we all went through together. But here I am, the guy who started it all, and I still haven't crossed six figures in a year.

I have also learned a lot about myself through these years, and I think I learn slower than most people. I've watched guys I literally know start ecom while I was doing it go from nothing to 20k days in like a year plus, while I'm still trying to figure out how to be consistent at 10k months. But I also feel like when I finally learn something, I really master it. Just takes me longer to get there.

Anyway, let me walk you through everything chronologically because its been a ride.

So back in 2020 when COVID hit, Canada gave us CERB which was 2k a month. I was a university student and that money was honestly life changing for me. Not because of the amount but because of how it made me feel. I've always been a huge car guy and the year before I had this Acura TL manual six speed that I loved. When CERB started coming in I told my boys if I save for a few months and yall lend me some cash I can get my dream car. At the time that was a BMW 335i manual convertible going for like 10 to 12k.

My closest friend lent me 4k, another boy lent me 2k, and I got the car like a month later. And man. That car changed my life and I mean that in a dramatic way. Driving through downtown Toronto at night with the top down, Drake playing lol, my girl at the time in the passenger seat, people on the street saying nice car. I can't even describe that feeling. I was driving my dream car, not working, still getting money deposited. It was the first time I'd ever been to a nice "expensive" restaurant and just felt like I was living.

Then CERB stopped around August and reality hit. Couldn't afford anything. Went back to school but ended up dropping out, got a job. Life felt genuinely depressing because that feeling was just gone and it felt so far away from ever coming back.

So I sold the BMW. Paid my boys back. Had about 3k left. And I said fuck it let me try to build something.

First thing I tried was dropshipping around 2021. Gimmicky products, tried a clothing brand, tried selling shisha hookahs. Nothing worked. I did manage to hit 1k in a day for like 3 days at one point but nothing was profitable or consistent. I've gone back to ecom multiple times over the years because it checks all my boxes. 1. You don't need to show your face. 2. You can scale to the moon. 3. You can do it from anywhere in the world. But its only ever lost me money. I think I'm finally accepting ecom just isn't it for me.

Then around 2023 I got into cleaning. Saw it blowing up on Twitter and jumped in. First time I actually made real money. Hit my first 5k month profit and I was mindblown. But the industry became a race to the bottom SO fast. A 300 dollar cleaning dropped to like 180 to 200 within months. My profit per job went from 100 bucks to basically nothing.

Through cleaning, I met a guy doing Airbnb property management and he told me to get into it. Thats what I've been doing since 2024 and its made me the most money out of anything. Crossed my first 10k and 15k month profit. I was probably one of the first people running Facebook ads for this in Toronto which gave me a real edge early on.

But now I'm stuck and heres why.

The numbers just don't work the way I thought they would. When I got into this I assumed most properties would do like 10k a month and I'd be making 1000+ per property at my 15% cut. Reality is most properties average like 3 to 4k a month and its super seasonal. Peak months a property might hit 10k but in November or February that same property drops to 3k. 15% of 3k is 450 bucks. Thats nothing.

I have about 15 properties right now. In the peak season, the properties generate around 100k a month in revenue, 15% is roughly 15k but I also have overhead so it ends up around 10k to 12k profit. In the low season I'm at like 4k. And thats before software and overhead costs. My best client has a 9 cabin resort that did 47k in one month last summer and I made about 3k off it. Thats my BEST client. If 3k a month is the ceiling per client the math just doesn't add up unless I somehow get to 200+ properties which creates a whole other set of problems like needing full time staff and dealing with way more overhead.

On top of that Toronto has been cracking down hard on Airbnb. They blame us for the housing crisis even though STR properties are less than 1% of housing stock in the city. So we are the low hanging fruit. Regulations in the city say you can only Airbnb the unit you actually live in (primary residence), you're also limited to 180 days a year of renting it out on Airbnb then you gotta switch to 6 month rentals, most cities around Toronto now need permits, and basically one client equals one property. For my clients, most of them aren't gonna go through the hassle of changing their driver's license address for verification and getting new permits every time they want to add a new property. They just don't care enough to do all that.

Lead gen wise, I can get leads cheap. About 3 bucks each, 60 to 70 leads a week on about 500 in ad spend. But the conversion is brutal. Out of 100 leads, 15 to 20 have a property that's not garbage, 5 of those actually want to start within a few months, and maybe 1 or 2 are ready to go within a couple weeks. So my close rate is like 1 to 2% (garbage). And I don't even break even on a client until about 3 months in. I just don't see how to scale this.

So here's what I've been thinking about. I know I'm a good marketer. Generating cheap leads is something I can do consistently, and I've learned how to apply marketing tactics across different industries. So I'm looking at starting a marketing agency. Two directions I'm considering.

First one is marketing for SaaS companies. Charge a big upfront fee like 10 to 12k plus a 4 to 6k monthly retainer. Help them move from low ticket subscription models to higher ticket sales. I've seen this model being done before and know someone who ran this exact model and collected 170k cash in like 60 days. 10 clients at 10k is 100k in cash collected in a month. The math is beautiful on paper.

Second one is marketing for mortgage brokers which is closer to what I already know since I'm in real estate. Tiered pricing. 3k a month with 500 going to ad spend so 2500 profit, or 4k a month, or 6k a month with more ad spend. 4 to 5 clients at the base tier gets me to 10k profit. I already tested out an offer and started running ads for this and got about 10 leads in the first few days, which is promising.

I also know I need to start creating content and putting my face out there which I've been avoiding. But I think its necessary at this point if I want to build a real lead magnet (plus I just need to do something different).

Now here's the personal side of things and why this is urgent.

My parents are in their 70s going into their 80s. They're not working anymore. Their expenses are becoming my expenses. Not by choice but because thats just the reality of the situation. I'm back against the wall financially. What I'm making now isn't keeping up with how fast things are adding up.

I've sacrificed a lot for this. Stopped hanging out with friends as much. Put basically everything into trying to make this work. I've probably generated close to 2 million in gross revenue over the last 3 years across all my businesses but that hasn't translated into the financial position I thought I'd be in. When I was 22, I thought by 27 I'd be living on my own, downtown with a BMW M2 lol but instead I'm at home grinding trying to figure out my next move.

I'm not trying to be dramatic, and I know I've grown. But I also don't want to keep doing the same thing and expecting different results.

So I guess my questions are.

Should I keep pushing the STR business? It's made me the most money, but the ceiling is low, scaling is brutal, and Toronto regs are working against me. It also requires me to be in person and local, which goes against what I originally wanted.

Should I go all in on the marketing agency? It checks more boxes and the margins are way better. But I don't want to fall into shiny object syndrome. If I can't hit 10k a month within 6 months I'd consider it pointless.

Am I just wasting my time overall? Because honestly, I could probably get a job paying 5 to 6k a month and end up in the same spot financially without all this stress. That thought keeps me up at night.

For anyone who's been through something similar or scaled past where I am. What am I not seeing? What would you do?

Appreciate anyone who actually read all this. My head's been a mess and I just need some real talk from people who get it.