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HMW #104: Should I keep my day job or become a full time real estate investor?

alan corey full time investor how to start quit job May 31, 2023

Read Time: 6.75 minutes


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Should you quit your day job and go whole hog on real estate investing? 

If you are evenly slightly resignation-curious, then count up your PTO days, hide out in that rarely-used conference room, and dig into this impromptu career guide that I've specially made for you.

Making that leap from part-time investor with steady full-time income to a full-time investor with sporadic cash flow can be a scary, blood-pumping thrill ride. 

It's either a round-trip ticket to the depths of debt hell and back or a Heavenly wealth-building ride to financial freedom.  You'll obviously want to make sure you are buying a ticket to the latter, unless you are the rare breed that finds bankruptcy court proceedings arousing. If that's you, then I suppose you also thought the Great Financial Crash in 2008 was when America was at her sexiest. Regardless, kudos to you for being into 232-year olds, that's actually quite progressive.

Ok, where were we?  Oh yeah, you spend your days fantasizing that your boss's corporate speak of:

  • "Too many balls in the air"
  • "Back burner that feature"
  • "Circle back on that for me"
  • "Make our delivery targets"
  • "Put your ducks in a row"
  • "Bring fresh ideas to the table" 
  • "That's some low-hanging fruit"

are all really just euphemisms (and permission) for you go take a massive dump on his desk.  We've all been there.  So I get it, you want to know right now when to make that jump to full-time investor life?  Or are you still stuck day-dreaming about the threesome consisting of your boss, his desk, and your bowels?


Ok, looks like you need some time to digest that exit strategy.

Unfortunately, most people have terrible timing when it comes to aligning their ambition with their current day-to-day responsibilities. It's important to remember:

One successful rental does not make for a full-time business.


Chances are you not a genius that understands real estate enough to go full-time, at least not yet. Other reasons why it may be best to wait before jumping ship:

  • You don't have the funds
  • You don't have the all-star team
  • You don't have the necessary deal flow
  • You don't have a clear career/retirement plan


No worries, I can help with that! There are 3 clear cut steps to take to craft an exit plan that sets you up for success:

Step 1: Ask a mortgage lender where you are on your DTI.

Your debt-to-income (DTI) level is the most important stat when getting approved for mortgages. And mortgage brokers can usually lend to borrowers up to a 45% DTI, so if you remove the income component of the variable then your most likely making you ineligible for getting a new mortgage. And well, you aren't going to go very far in your second-career of real estate without someone excited to lend you money.

Lenders drool over W-2s. It's the golden ticket to mortgage approval, so get all the mortgages you can with your W-2 in place until you max out your DTI. Once you max out your DTI, your easiest step forward is commercial loans. Commercial lenders lend on the deal more than the borrower, but this is riskier, so commercial loans are more expensive and have higher rates, and it's a littler hard to find commercial products offering 30-year fixed mortgages.

I want you get as many low-cost, low-down payment, 30-year fix residential mortgages as you possibly can. And then you'll have the foundation for F-you money from rentals that allows you to leave the 9-5 in good squatting standing.

Step 2: Give your current properties jobs

Your job right now is to bring enough income to cover your expenses. Now is the time to outsource this to the homes you already own. Make the cash flow of your first rental have a job of paying for your utility bills. Then make that second rental of yours job to cover your transportation expenses. That third rental can be "employed" to cover your food budget.

You don't have three rentals? The properties you have don't cover any bills? Oh okay, well, then get to tacking those KPIs at your day job so you can get a raise soon and start acquiring some assets that pay your bare minimal housing expenses. Want more info on this approach, check out my book "House FIRE" which breaks this down step-by-step with a lot fewer poop jokes.

Many investors take their properties cash flow to inflate their lifestyle, but you need real estate cash flow to cover the basics first. Once this is done, you can really fly, like double-birds to your boss's face on your way to the exit.

You properties are your income replacement, so treat them as such. If they fail at their job, then you either need to train them up (renovate them) or fire them (sell them.) If it's job is to cover your car loan payment then make sure it covers your car loan payment. You have to learn how to run a tight ship now so that you can run an even tighter ship when it's your full-time gig. 

And the best part of this arrangement?  When your houses have job, the eventually give you a raise. 

That's right! When the mortgage gets paid down and when rents go up, your new and improved cash flow on a property is like getting a raise at work: completely unexpected and possibly undeserved.

Now check in with yourself. Is this little reframing of the purpose of your real estate investments starting to make some sense?

Good to hear! With this improved attitude, I bet your boss puts in your annual review that "you are a good team member that is well-respected amongst your peers" which is corporate speak for "I think this person quiet quit 6 months ago."


Step 3: Change your identity into a real estate investor

Good news, this is the easiest part. And the most fun one! You must re-create yourself as a full-time investor before you actually made the leap.

Is your personal brand currently one of the following:

  • Dude that lives and breathes SaaS tech startups
  • Gal that coaches volleyball at a private school
  • Whiz kid developer and code junkie

Which one of these personal brands makes people think, I should talk to them about this off-market property I have available? Now imagine if you had the same job but this is what people say about you outside work:

  • Dude I work with has five duplexes, he might be interested
  • This gal that coaches in our league just flipped her third house
  • Our tech lead house-hacks and owns a few triplexes on my block


These are all describing the same person!  None of these descriptions say they are bad at their job.  Or they won't get a promotion because they have interests outside work.  It says, if anything, they are successful in multiple fields.

Now you want to introduce your favorite contractor to them.  Now you want to reach out to them with an off-market opportunity.   This is having your personal brand create organic inbound lead flow and networking.  This is the biggest switch you can make prior to jumping full-throttle.  It changes your exit from "Dennis left to do something with real estate, guess he's having a mid-life crisis" to "Dennis was doing so well in real estate he decided to do that full-time and let me introduce you to him."

So how do you shed the monkey suit from your current job and replace it with an outfit befitting a real estate investor?

  • Water-cooler talk is now your weekend warrior real estate stories
  • Create a new real estate channel in the office Slack/Discord
  • Transition your social media into being real estate focused 
  • Present real estate Lunch N' Learns to your co-workers
  • Be an investor that has a job to further your investing

So what do you think?

Can you be someone with an exit plan to be a full-time investor?

Can you take these 3 steps before putting in your two weeks notice?

Can you be an investor with a job instead of a employee who invests?



  • Get as many mortgages on your W-2 as you can
  • Give your current properties jobs to pay bills
  • Rebrand yourself as an investor

Are you a newer investor looking for some guidance?

We teach real estate! 


Check out House Money Media courses and coaching options.


Want to promote your brand to a growing and dedicated real estate audience? Reach out to [email protected].