Intro - Looking to get out of W2 and build a meaningful legacy for my family

[Andrew Montgomery]

Hello! I live in a suburb of Indy with my wife and 3 teenage kids. We just jumped in the game in April when we bought our first STR in Sevierville, TN. Went big (5BR) and spent more than we wanted but so far so good (on track to be close to breakeven after 1 year). But after doing a lot of reading/research, thinking we want to focus more on LT for the next few deals.

I turn 50 in a month. I've worked in technology sales/mgmt for 28 years and have done well, but probably need to work 5 more years to ensure a comfortable retirement and legacy for the kids. The problem: The thought of working 5 more years in a high stress, anxiety producing W2 is almost unbearable. My wife and I are committed to real estate as our post-retirement gig. I know this is an intro forum but if anyone feels so inclined, would love some different perspectives, what would you do if you were in my position.

The lure of a good salary, benefits and insurance are hard to walk away from. But I'm so busy with my job that I have almost no time to focus on our real estate business (not to mention the constant stress and anxiety of delivering a number year after year). Perfect world, I'd quit today and focus on real estate. I'd rather not touch my 401k but do have $1.2M in stock I could liquidate. Would you throw caution to the wind and jump in with both feet, using half of your savings to build up a real estate portfolio? Or push through working another 4-5 years to make sure you were "safe"? I'm not very well versed on creative financing yet so maybe a better option that doesn't require me parting with my cash? Looking forward to connecting with like-minded folks in this new world!

[Ray Hage]

Quote from @Andrew Montgomery:

Quote from @Ray Hage:

Quote from @Andrew Montgomery:

Hello! I live in a suburb of Indy with my wife and 3 teenage kids. We just jumped in the game in April when we bought our first STR in Sevierville, TN. Went big (5BR) and spent more than we wanted but so far so good (on track to be close to breakeven after 1 year). But after doing a lot of reading/research, thinking we want to focus more on LT for the next few deals.

I turn 50 in a month. I've worked in technology sales/mgmt for 28 years and have done well, but probably need to work 5 more years to ensure a comfortable retirement and legacy for the kids. The problem: The thought of working 5 more years in a high stress, anxiety producing W2 is almost unbearable. My wife and I are committed to real estate as our post-retirement gig. I know this is an intro forum but if anyone feels so inclined, would love some different perspectives, what would you do if you were in my position.

The lure of a good salary, benefits and insurance are hard to walk away from. But I'm so busy with my job that I have almost no time to focus on our real estate business (not to mention the constant stress and anxiety of delivering a number year after year). Perfect world, I'd quit today and focus on real estate. I'd rather not touch my 401k but do have $1.2M in stock I could liquidate. Would you throw caution to the wind and jump in with both feet, using half of your savings to build up a real estate portfolio? Or push through working another 4-5 years to make sure you were "safe"? I'm not very well versed on creative financing yet so maybe a better option that doesn't require me parting with my cash? Looking forward to connecting with like-minded folks in this new world!

I certainly wouldn't quit my job and liquidate all the stocks. I don't think it's a wise decision due to the amount of risk. I was able to focus on my W-2 (at that time) and build the RE portfolio on the side. I started acquiring LTRs in my 30s and it was cheaper back then. I think the safe decision would be to focus on your W-2 and do your best with your limited time to get an investment property. Who knows? You might not like it that much so it's not wise to quit and liquidate your stock portfolio for this.

I am an investor first but I also am a realtor and private money lender. It's not quick money and there unexpected expenses that pop up from time to time. It takes a while to build a consistent and sufficient income to replace your W2. If it goes poorly in RE, what would you do? You have to consider worst case scenario of not doing well in RE right away. I like you goal but I think it would be best to build up as best as you can while maintaining a full time position.

Thanks Ray, good advice and I know that's the wise approach. I probably need to look for a less demanding W2 so I can enjoy the next ~5 years and have a little more time to devote to RE to determine if it's right for us, while still making a good income in case it's not. Appreciate the input! 

Yep a less demanding W-2 would work well. This is what I did when I was transitioning out. In fact, the last job I had was very slow at times so that gave me time to work on the RE analysis and managing the properties I already had. Obviously, there was no fulfillment in that job but it was wise. I really made a ton of progress in the RE industry while in that job. It did come with a pay cut but worth it since I wasn't crazy busy or dead tired during or after work. Hopefully, you can find something similar without a major pay cut