Are You Crazy to Think You Can Quit Your Job?

can you really live off a land flipping business

REtipster provides real estate guidance — not tax or investment advice.

This article should not be interpreted as financial advice. Always seek the help of a licensed financial professional before taking action.


Is it really possible to quit your job and live off the income from a real estate business?

I mean, seriously… whether you’re flipping land, flipping houses, wholesaling houses, buying rental properties, you have to admit – it’s a legitimate question.

Back when I was getting started, I used to wonder about this all the time.

I remember countless drives to and from my day job when I would have this internal dialogue with myself…

“I know others have made enough with this business to quit their job, but am I really capable of doing it?”

“Will I EVER feel comfortable enough to do this full time? Am I just kidding myself here?”

“The people who are ACTUALLY successful got there in 18 months, but I’m still not there after 3+ years. Is this ever going to happen for me??”

You see… my journey to financial independence wasn’t exactly fast.

I started my first real estate business back in 2008, and it wasn’t until 2016 that I FINALLY felt comfortable enough to quit my job and focus on real estate full-time.

It’s not that I couldn’t have done it sooner, but I’m someone who worries, overanalyzes and overthinks decisions of this magnitude. I need to have several contingency plans in place before I do something as monumental as quitting the J.O.B.

RELATED: Six Months After Quitting My Job – Here Are My Honest Thoughts.

Even though I knew that on paper, it was technically possible for my real estate business to be a fully sustainable, self-supporting business, there was a LONG period where I had my doubts, and I wondered if all of this dreaming would ever lead anywhere.

I’m Not Alone

I know I’m not the only person who has laid awake at night thinking about these things.

Being a full-time real estate investor is a big deal, and there are a lot of obstacles that need to be overcome in order to get over this hurdle.

  • Is it really possible to quit your job and survive off a real estate business full-time?
  • How can someone legitimately create enough sustainable income to rely on over the long-term?
  • What are the biggest obstacles to achieving this dream?
  • How much debt vs. equity should I have before I make the decision?
  • What should I do about health insurance?
  • How much savings should I have in case of a sudden financial catastrophe?

Part of what makes it such a perplexing (and scary) decision is that there are a lot of different paths that can be taken.

There isn’t a one-size-fits-all formula that will get you there. Every person has to fight different battles as they’re figuring it out.

With that in mind, I wanted to share several stories and case studies from people who have made it. My hope is that you’ll see a little bit of yourself in the stories below – because there’s a good chance you share something in common with each of these folks.

1. How To Survive Off Your Land Business (Without Starving To Death)

In this interview with Chris Gibson, Jaren asks about how he manages to feed his family and live a sustainable lifestyle with the income he generates from his land investing business.

Given the inherent “spikey” (and sometimes unpredictable) nature of this form of income, there is a lot to be learned about how to add certainty and reduce risk when depending on this source of income.

It’s also worth noting, your real estate business (whether it’s vacant land or some other type of real estate) doesn’t need to net millions each year before you can leave your job.

If you’ve got other forms of income (whether it’s another business or a working spouse), you can absolutely use this to your advantage.

2. How Brett Snodgrass Built a House Wholesaling Empire.

If anyone has ample experience with the issues of investing in real estate full-time, it’s Brett Snodgrass of Simple Wholesaling.

In this interview, Jaren drills down to find a lot of answers to the questions we all have about living this kind of lifestyle.

Is it really possible to quit your job, survive and thrive with a real estate investing business? How are you supposed to manage your finances and pay for your overhead expenses while also paying yourself? How do debt and taxes factor into the overall picture? What are the biggest challenges with this kind of business and lifestyle?

3. Going From 0 to 10 Deals per Month (and quitting his job) in 18 Months

Willie Goldberg is one of those guys who didn’t sit around and wait for years before quitting his job. He took the leap of faith on his first direct mail campaign, and within 18 months, he was able to transition to full-time land investing and generate $12,000 in monthly cash flow.

It doesn’t always happen this quickly, but Willie’s story is a great example of what can happen with a clear goal in mind and a willingness to work hard (and smart) to pursue the dream.

We actually did another, more in-depth interview with Willie on episode 39 of the REtipster Podcast, where he shared a lot more insights on how his business works and how he made the transition. You can also check out Willie’s website at WGlands.com.

4. David fired his boss to invest in land full-time. Here’s how he did it…

David VanSteenkiste is someone who jumped into the land business and took it seriously from the very beginning. With the benefit of experience from working with houses, he understood the challenges that come with real estate.

Part of David’s story involves a partnership, which is an interesting component to think about, especially with the potential it has to grow your business faster and reach your freedom number sooner rather than later. If you’re in the land flipping business and you want to grow it to the point where you have total autonomy over your life (or even if you’re considering jumping into the land investing game as a beginner), David is a great example of what’s possible when you take this business seriously and take action on building your financial freedom.

Check out the show notes from this interview with David on episode 36 of the REtipster Podcast. You can also check out David’s website at Mile High Rural Land.

5. Self-Employment Tips from a Self-Employed Financial Advisor

The challenges of self-employment aren’t exclusive to real estate investors. Everyone has to overcome some big obstacles to earn this kind of financial freedom.

In this interview, I chat with my college buddy Chris Wiesehan about what it took for him to make the leap into becoming a full-time financial advisor. Given Chris’ expertise, he also shares some of his guidance and suggestions for how someone can make the leap from day job to pursuing their actual dream in a financially prudent way.

Want to learn more about Chris? Check out his website at CJW Capital.

6. (BONUS) From Full-Time Employee to Full-Time Entrepreneur

While we’re on the topic, I thought I’d share this interview as well. Shortly after I quit my job in 2016, my friend Sharon Vornholt was nice enough to sit down at record an interview for her podcast about what my experience was like.

To see more details on what my experience was like, check out this blog post.

Different Paths for Everyone

One last thing I’d like you to bear in mind is that there is no cookie-cutter approach to quitting your job.

It’s also entirely possible (and even preferable, in some cases) to continue working your job even though your business is making enough to support you. There are a lot of stories of folks who have generated more than a full-time income from their business while working it on the site – but they continued to stick with their job until they were ready to leave.

Have you made the leap to full-time self-employment? Do you have any tips or suggestions you’d like to share with the REtipster community? Let us know your thoughts in the comments below!

The Best Real Estate Investing Strategy I’ve Found

I'll be completely honest with you. The most powerful strategy I've used to build my real estate investing career is probably NOT what you might guess.

Land investing (that's right, buying and selling vacant land) is a massive opportunity that most investors aren't paying attention to. For the few land investors who know how to pursue this business with the right acquisition strategy, it's an extremely lucrative and low-risk way to build serious wealth from real estate.

If you want to get the inside scoop on how to start and run your own land investing business, come and check out the REtipster Club – where I've put together a full 12-module course with dozens of videos, bonuses, downloads, group coaching sessions and a members-only forum (where we spend time answering questions every week). There is no better place to learn this business from the inside out!

About the author

Seth Williams is a land investor and residential income property owner, with hundreds of closed transactions and nearly a decade of experience in the commercial real estate banking industry. He is also the Founder of REtipster.com - a real estate investing blog that offers real world guidance for part-time real estate investors.

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