Starting Investing Journey for Kids (and myself)

Providence, Rhode Island
Buying & Selling Real Estate
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Starting Investing Journey for Kids (and myself)

Jeff Gaccione
Member since 2025 · 6 posts · 2 votes
I’m looking to start my kids and my investing journey in the next 6-18 months. For me I’m looking for additional streams of income and tax benefits. For them I want to teach them about getting money working for them and to help house hack with their first time homebuyer benefits. I’ll take any initial advice this community is willing to share.
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Mohammed Rahman
Real Estate Broker · New York, NY · Member since 2020 · 2k+ posts · 1k+ votes
10mo

Hi Jeff,

I really admire that you’re thinking about investing not just for yourself but as a way to teach your kids. That kind of hands-on financial education is something they’ll carry for life.

1. Start with financial literacy basics. Teach them concepts like compounding and the time value of money. If you haven’t read The Richest Man in Babylon, it’s an excellent book for developing the mindset needed to build real wealth. Rich Dad Poor Dad is also a classic. You can’t invest smartly if you don’t understand how to save or invest from the beginning.

2. House hacking is a great entry into real estate investing. You'll get introduced to underwriting, property management, etc. There are tons of resources online like YouTube that show you how to evaluate deals. Remember that when you're running your numbers, it's your inputs that matter. Be realistic with your assumptions and lean conservative whenever possible. 

3. Financing matters. Learn traditional methods, but don’t be afraid to explore creative financing. As @Ken M. says, teach them about creative financing.

4. Network with local investors! Join a local REIA group, attend meetups. You might be able to find someone who will let you shadow them or just tell you about how they run numbers and structure deals.

5. Tenacity is crucial. This industry rewards persistence and consistent effort more than anything else.

Excited to see where you real estate investing journey takes you, and good luck!

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  • Ken M.
    Investor · Get yourself trained before doing something inadvisable. · Member since 2024 · 3k+ posts · 1k+ votes
    10mo
    Quote from @Jeff Gaccione:
    I’m looking to start my kids and my investing journey in the next 6-18 months. For me I’m looking for additional streams of income and tax benefits. For them I want to teach them about getting money working for them and to help house hack with their first time homebuyer benefits. I’ll take any initial advice this community is willing to share.
    I'm biased, so I'd naturally say, teach them about creative financing. They won't get much, if anything in school, about how money works, so teach them something that will put them ahead of the game. We started our kids when they were big enough to handle chores around the rehab, that gave them concrete examples of what we do. We always included taking them to the hardware store. I explained to them what a deed of trust, is what a warranty deed is, how they go together and why. And all the things in between.
    0Reply
    • Jeff Gaccione
      OP
      Member since 2025 · 6 posts · 2 votes
      10mo

      @Ken M. Thank you, son is 18, graduating this year and not inclined to go to school full time but part of an internship that will give him a full time job upon graduation.  I'm debating on bringing him along on a real estate journey as a way to help launch him as well.  Thanks for your tips about the deeds and hardware stores etc!

      0Reply
    • Ken M.
      Investor · Get yourself trained before doing something inadvisable. · Member since 2024 · 3k+ posts · 1k+ votes
      10mo
      Quote from @Jeff Gaccione:

      @Ken M. Thank you, son is 18, graduating this year and not inclined to go to school full time but part of an internship that will give him a full time job upon graduation.  I'm debating on bringing him along on a real estate journey as a way to help launch him as well.  Thanks for your tips about the deeds and hardware stores etc!

      All of our kids have their degrees. None are working in their chosen fields. :-) Real estate is paying off for the boys,

      0Reply
  • Aaron ZimmermanBusiness Member
    Accountant · Chicago, IL · Member since 2018 · 2k+ posts · 1k+ votes
    10mo

    What's your plan to buy your first property? What's your strategy (buy and hold, BRRRR, STRs, house hack, live in flip)?

    If you're teaching your kids, it'd be great to teach them budgeting and personal finance. That's the base of any investing, in my opinion, because you need savings to invest. 

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    0Reply
  • Wale LawalBusiness Member
    Real Estate Broker · Houston | Dallas | Austin, TX · Member since 2018 · 5k+ posts · 2k+ votes
    10mo

    @Jeff Gaccione

    I must say that is a fantastic goal with a fantastic timeframe. In order to model the process, tax advantages and systems, I would suggest to first purchase your own buy and hold or small multifamily. As your children get older you should then involve them in underwriting, rent tracking and fundamental decision making. Finally when they are ready, house hacking with FHA or first time buyer programs is an effective way to develop long term wealth while teaching leverage, cash flow and responsibility.

    Good luck.

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  • Marcus Auerbach
    Investor · Milwaukee - Mequon, WI · Member since 2010 · 5k+ posts · 7k+ votes
    10mo
    Quote from @Jeff Gaccione:
    I’m looking to start my kids and my investing journey in the next 6-18 months. For me I’m looking for additional streams of income and tax benefits. For them I want to teach them about getting money working for them and to help house hack with their first time homebuyer benefits. I’ll take any initial advice this community is willing to share.

    House hacking is a total no-brainer and includes a ton of lessens for colledge age kids. They learn how to search, evaluate and finance real estate. Then how to do repairs, hire contractors, screen and manage tenants. And on top of all that you have the financial benefits. And it takes away their first time home buyer fears.

    Now to the bad news: additional income and tax shelter don't really come into play until you get to a portfolio of properties, so you have to scale. Anything under 10 units total will give you long term wealth, but the cash flow is going to be negleable. Any free cash flow should go into more downpayments and towards improving asset values. But even one unit is super beneficial towards your retirement, just don't bank on extra income. (you'll get however some extra work ;-)

    1Reply
    • Jeff Gaccione
      OP
      Member since 2025 · 6 posts · 2 votes
      10mo

      @Marcus Auerbach Thanks, interesting about the less than 10 units.  I know this won't be easy money.  But moves like this feel necessary to help set them up for the future.  I don't have as long of a time horizon but can use some write offs.

      0Reply
  • Mohammed Rahman
    Real Estate Broker · New York, NY · Member since 2020 · 2k+ posts · 1k+ votes
    10mo

    Hi Jeff,

    I really admire that you’re thinking about investing not just for yourself but as a way to teach your kids. That kind of hands-on financial education is something they’ll carry for life.

    1. Start with financial literacy basics. Teach them concepts like compounding and the time value of money. If you haven’t read The Richest Man in Babylon, it’s an excellent book for developing the mindset needed to build real wealth. Rich Dad Poor Dad is also a classic. You can’t invest smartly if you don’t understand how to save or invest from the beginning.

    2. House hacking is a great entry into real estate investing. You'll get introduced to underwriting, property management, etc. There are tons of resources online like YouTube that show you how to evaluate deals. Remember that when you're running your numbers, it's your inputs that matter. Be realistic with your assumptions and lean conservative whenever possible. 

    3. Financing matters. Learn traditional methods, but don’t be afraid to explore creative financing. As @Ken M. says, teach them about creative financing.

    4. Network with local investors! Join a local REIA group, attend meetups. You might be able to find someone who will let you shadow them or just tell you about how they run numbers and structure deals.

    5. Tenacity is crucial. This industry rewards persistence and consistent effort more than anything else.

    Excited to see where you real estate investing journey takes you, and good luck!

    2Reply
    • Jeff Gaccione
      OP
      Member since 2025 · 6 posts · 2 votes
      10mo

      @Mohammed Rahman Great Suggestions, I've heard of the Babylon book, I'll add that to my list asap. My goal is traditional financing to start since he will have some FTHB options . But yes then creative financing after that.

      0Reply
  • Kevin Jo
    Member since 2025 · 28 posts · 22 votes
    10mo

    Forget the books, does not equate to your area. Everywhere is different. RI is similar to Ct where MF and SF are net zero or negative cash flow because of high prices. Deals can be found but require alot of work. Sweat equity deals are the best to start off rent positive. Do not start off net negative!!! Take your time and find the right deal. 

    0Reply
  • Nicholas L.Pro Member
    Flipper/Rehabber · Pittsburgh · Member since 2018 · 6k+ posts · 5k+ votes
    10mo

    @Jeff Gaccione

    just to echo what @Marcus Auerbach said, cash flow is tough right now unless you're in a cash-flow generating business.  and by "tough" i mean there isn't any at all.  =)

    but equity is still gettable.  and in the long term, equity can be turned into cash flow - by selling, refinancing, value-adding, 1031ing, appreciation, rent growth, etc.  10+ units and 10+ years I think is the sweet spot.

    having your kids start early and build equity is a great strategy.

    1Reply
  • Rick Albert
    Real Estate Agent · Los Angeles, CA · Member since 2018 · 2k+ posts · 1k+ votes
    10mo

    My daughter is under 2 years old but I can't wait to get her involved. Here is my plan:

    -As I get more organized, I intend on having monthly or quarterly family meetings about the properties. This is what the ultra wealthy do and how they are able to beat the stereotype of wealth running out by the third generation. 

    -If there is a problem, come up with two viable solutions and have them help in the decision making process. 

    -Not sure how I'm going to do this part but I want to make it clear that if my daughter isn't willing to work on the business with me, then she isn't getting them. I'll donate the properties when I die. She needs to earn it just like my wife and I did to get us where we are today.

    -Have your kids listen in on the calls with the contractors, property managers, etc. See how hard you work and set that as a standard.

    Hope this helps. Good luck!

    1Reply
  • Ashish AcharyaBusiness Member
    CPA, CFP®, PFS · Sarasota, FL · Member since 2017 · 5k+ posts · 3k+ votes
    10mo

    Hey @Jeff Gaccione! I love that you’re starting this journey and bringing your kids along with you. That’s really what building generational wealth through real estate is about, and you’ve already gotten some solid advice here.

    There’s a lot to consider early on, financing, strategy, what’s actually worth the effort, and especially taxes. A lot of people chase “passive” income without realizing how real estate can impact their current income, too, when it’s structured the right way.

    To start, I'd focus on the basics of financing. Since you're considering a house hack, it doesn't need to be complicated. A primary residence loan, conventional or FHA, can get your kids in the door. They live in one unit, rent the others (sometimes even to friends), and let that income help cover the mortgage. The beauty of house hacking is that it often helps fund the next primary without jumping into creative or complex financing right away.

    From a tax perspective, even small rentals like a house hack can create depreciation that helps soften the tax hit while you’re building cash flow. It’s also important to understand passive versus non-passive income early and how that fits with your current income. That context helps determine whether long-term or short-term rentals make the most sense for your overall financial picture.

    For your kids, house hacking is one of the best real-world lessons there is. I’ve seen young buyers live in one unit, rent the rest, and walk away a few years later with equity, confidence, and financial skills most people never learn.

    The biggest mistake I see is overcomplicating things too early. You don’t need fancy structures to start. Focus on good deals, clean numbers, and understanding cash flow and the tax strategy behind it all. As the portfolio grows, that’s when advanced tax planning really matters. You'll also want to build a team, a mortgage lender you trust, a knowledgeable real estate agent in the areas you're interested in, and eventually a CPA who specializes in real estate is KEY if you want to scale. Jump on free webinars and learn from real-life stories they share, all of these types of professionals should have free resources like this.

    You’re on the right path by being on here, jumping in, and asking the right questions. Good luck, and happy to connect.

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  • Camren BerryPro Member
    AZ · Member since 2021 · 86 posts · 14 votes
    9mo

    That’s a great long-term mindset, both for building additional income and teaching your kids strong financial fundamentals early. Many families start by building a small rental portfolio alongside educating their kids on cash flow, leverage, and risk management. 

    [email protected]480-818-6158
    0Reply
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