Welcome back to The Huddel. Thanks for being here.
I posted a 7-second video this week about the things I wish I knew before I left my job to invest in real estate and buy businesses.
7 seconds is enough to plant a flag. It's not enough to actually help anyone.
So here's the longer version. The stuff I'd tell my younger self over a beer if I could go back to the day I handed in my notice.
1. There's no shame in keeping your job.
The internet will tell you W2s are prison and entrepreneurs are free. That's a lie sold by people trying to get clicks.
A steady paycheck while you build on the side is one of the most underrated wealth strategies that exists. It funds your deals. It keeps your family fed. It buys you the patience to wait for the right opportunity instead of forcing the wrong one because rent is due.
Stay employed longer than you think you need to. Your future self will thank you.
2. Your runway needs to be longer than you think.
I had 12 months saved when I jumped. I still felt the squeeze.
Deals take longer to close than the spreadsheet says. Revenue takes longer to hit than the pro forma promises. And life keeps happening the whole time - kids, medical bills, a roof, a car, a thousand small things that don't care about your business plan.
12 months is the floor, not the goal. If you can swing 18, do it. The extra 6 months is the difference between making decisions from a place of strength and making them from a place of panic.
3. Account for the expenses nobody warns you about.
Health insurance is a big one. I'm lucky my wife carries ours through her job, but if you don't have a spouse with benefits, that bill alone can run you $1,500+ a month for a family.
Then there's self-employment tax, which is another punch in the face. You've been paying half your whole career and your employer covered the other half. Now you cover both. Surprise. Good news is you now get to play the tax game. But you gotta learn it.
Plus the random stuff. A new HVAC. A baby on the way. A deal that needs $20K of earnest money you weren't planning on. A laptop that dies the week you can't afford to replace it.
The "I'll figure it out" budget always loses.
4. Build a flywheel, not a hustle.
This one took me a while to actually internalize.
One income stream can be a nice lifestyle business. But the whole point of leaving the W2 is to build something that compounds, not to trade one boss for a hundred customers who all want a piece of you.
Take the cash flow from one thing and feed it into the next. I flipped land, rolled those profits into note investing, and let the payments compound back in. Each piece feeds the next.
That's how you build something that doesn't collapse the second you stop pushing. The flywheel is the point. The hustle is just the cost of getting it spinning.
5. Going from zero to one is brutal.
I had two startups fail. I'd never do another one from scratch.
Buying cash-flowing assets and businesses is hard enough. Building something from nothing while also paying your mortgage is a different kind of pain that almost nobody talks about honestly. The forums and the podcasts make it sound like grit and grind get you there. What they don't show you is the 18 months of zero revenue, the savings draining, the conversations with your spouse that get harder every month.
If you can buy instead of build, buy. Cash flow on day one is worth more than the dream of building the next big thing.
6. Cash flow beats everything.
Not appreciation. Not "potential." Not the pitch deck math. Not the exit you're hoping for in 5 years.
Real dollars hitting your account every month is what keeps you in the game long enough to win. Cash flow is oxygen and I’m convinced that everything else is decoration.
The takeaway.
The dream of owning your time is real. I'm living a version of it right now and I wouldn't trade it.
But the path there is way less sexy than Instagram makes it look. It's spreadsheets, savings accounts, boring decisions, and a long list of things you wish you'd known before you jumped.
Catch you next Thursday,
Jake