Retiring after 22 years investing and passing on a a Legacy Portfolio

Retiring after 22 years investing and passing on a a Legacy Portfolio

Member since 2026 · 1 post · 2 votes

I grew up poor in southern Maryland. A family of nine brothers and sisters. I planted corn and tobacco in the spring and the fall and worked the sport fishing boats during the summer. At the age of 16 I joined the Navy for two tours.

Three of the most important things I ever learned is :

. Mae your bed every day that way you start the day accomplishing something.

. following the same advice everyone else does leads to rigid thinking and lack of problem solving skills.

. learn 1 new skill every day from some source like YouTube ad keep a log of the skills and the source.

I started investing by purchasing rundown 1 bedroom condos for 40 to 50 k . I would ask the owners to hold the note for 3 to 5 years at market rates. I would live in them while doing the renovation room by room. I did all the work myself while studying for my MHIC license .

After the first 3 I had 3 rentals with tenants. I then paid off the 3 loans and got a consolidated loan for the next 2.

(Got married and my wife after a little training took over the accounting and tenant relations as well as final renovation decisions like paint colors and decor.

Fast forward, we then did 15 town houses ( I went to part time work ) , started hiring nieces and nephews for summer work. We started on single family homes (paying cash).

At this point we were adding other family members full time to fill other positions like Demolition, Reno Build out, marketing, pre purchase.

At this point we also started a 401K program, education program.

Note anyone hired had to work on a minimum of 5 house projects from start to finish, learning all aspects of renovation including swinging a hammer, digging ditches, estimating not only projects , but time estimates.

This point we found a great niche market, corporate executives rentals. Mainly to large companies that bring in CEO and C suite executives. These are 4 to 5 bedroom McMansions on 3 acre lots. These properties come fully furnished, a maintenance plan and land scraping plan.

We then split the companies into divisions and refined the roles .

Internal controls include:

. every division has a division manager and assistant division manager.

. AP and AR are separate persons.

. We run Quickbooks with Contractors Job Cost (updates disabled, so we don't have to pay for subscription services. Microsoft Office Suite ( disabled) Crystal report writer, proprietary property management and tenant portal software, proprietary property job cost software that allows me to import property lists and run ROI calculations on an infinite number of properties based on parameters entered.

We are retiring now at 55, it’s times to spend a lot more time surfing ad scuba diving .

My wife and I have enjoyed both the good ties and bad times of investing. Our daughter will be CEO and we are confident she will do well as she has been my XO for the past 3 years. We are also staying on as the Board of directors for the next 10 years.

We had lawyers involved in the purchase and a complete review of corporate documents.

Feel free to ask any questions, I’m more than willing to answer certain questions.

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  • Jay HinrichsBusiness Member
    Real Estate Consultant · Summerlin, NV · Member since 2014 · 45k+ posts · 66k+ votes
    1d

    Nice post and way to build a family business I am sure its quite gratifying to you. !!!

  • Realtor · Memphis, Shelby County · Member since 2026 · 221 posts · 72 votes
    21h

    Travis, congratulations on 22 years — that's a real legacy, and building it as a family business makes it even better. If you're open to sharing, I'd love to hear what you'd do differently in those first five years knowing what you know now. So many new investors get caught up chasing the "perfect" first deal instead of just getting started with solid fundamentals, the way you did with those first condos. I'm also curious how your criteria for a good deal evolved as the portfolio grew — did you get more conservative, or did experience let you take on bigger projects with more confidence? Thanks for offering to pass the knowledge on. Enjoy the surfing and scuba diving!

  • Member since 2026 · 237 posts · 25 votes
    20h

    What a journey, from the farm and the boats to building something your whole family could share. Congratulations on the retirement, and thank you for telling the story so openly.

    Randy, Bunklow

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