20 years ago I crashed and burned with the market

Dayton, Ohio
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20 years ago I crashed and burned with the market

Christopher Routson
Realtor · Franklin, OH · Member since 2026 · 1 post · 1 vote

20 years ago I crashed with the market. I had a duplex and a single-family and was in bankruptcy by 2008. I’m wanting to get back into the swing of things. I do need a mentor. Who on here has a reputable mentor program not just the fox and the cat taking advantage of Pinocchio.

I was 19 when I bought my first home 21 when I bought the duplex and I’m done being naïve at 45. I’ve been through the school of hard knocks. I know what not to do. But I am looking for a mentor who could help me buy the right properties to cash flow up to $12,000 a month, the job market is scarce and I have zero retirement.

What I’m looking for is a retirement portfolio that I can put in a trust to provide as an inheritance for my children after I die. I really would like to sell Real Estate as I am a realtor, part of selling real estate is being able to survive month after month and I believe if I invested wisely now by the time I put another 20 years of work and I will have this inheritance that I’m only talking about right now, I’m ready to take action who is willing to help me?

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G. Brian DavisPro Member
Investor · Hatboro, PA · Member since 2016 · 2k+ posts · 845 votes
15h

You’ve already learned some of the hardest lessons in real estate, and honestly, that experience is valuable. A lot of investors never get humbled by a bad cycle, but those lessons can make you a better investor the second time around.

I’d be careful about looking for someone who has all the answers. A good mentor should help you think through deals, understand the numbers, and avoid mistakes not just sell you a system.

I’d start by getting really clear on your numbers. What markets are you investing in? What does a property need to produce for you to hit your goals? How much capital do you have available? What level of risk are you comfortable with?

The goal of building a portfolio for retirement and your kids is a great one. Just focus on buying solid assets one at a time and making sure each deal works before moving on to the next.

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  • G. Brian DavisPro Member
    Investor · Hatboro, PA · Member since 2016 · 2k+ posts · 845 votes
    15h

    You’ve already learned some of the hardest lessons in real estate, and honestly, that experience is valuable. A lot of investors never get humbled by a bad cycle, but those lessons can make you a better investor the second time around.

    I’d be careful about looking for someone who has all the answers. A good mentor should help you think through deals, understand the numbers, and avoid mistakes not just sell you a system.

    I’d start by getting really clear on your numbers. What markets are you investing in? What does a property need to produce for you to hit your goals? How much capital do you have available? What level of risk are you comfortable with?

    The goal of building a portfolio for retirement and your kids is a great one. Just focus on buying solid assets one at a time and making sure each deal works before moving on to the next.

    1Reply
  • Jules Aton
    MD/DC · Member since 2024 · 1k+ posts · 1k+ votes
    13h

    If you are a Realtor what about successful colleagues in your brokerage? Also I'd focus on building a good income from your job while slowly, thoughtfully building a RE portfolio. Unless someone started years ago I suspect it is difficult to acheive a $12,000 monthly profit unless you have a stack of cash to begin with or decades to wait.

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  • Ashish AcharyaBusiness Member
    CPA, CFP®, PFS · FL · Member since 2017 · 5k+ posts · 3k+ votes
    6h

    Christopher, with what you’ve already been through, I’d make the second run much more about survivability than speed.

    If your goal is eventually replacing $12K/month of earned income and building something your children can inherit, I’d work backward from that number instead of starting with “how many doors do I need?” Figure out how much reliable monthly cash flow you actually need, how much debt you’re comfortable carrying, and how much liquidity you want outside the properties.

    The biggest thing I'd avoid is building a portfolio that only works when occupancy, appreciation, and financing all cooperate. I'd rather see fewer properties with stronger DSCR, healthy reserves, conservative leverage, and multiple exit options than a larger portfolio that leaves you vulnerable during the next downturn.

    For a mentor, I’d also look closely at how they actually make their money. I’d want someone whose incentives are aligned with helping you buy good real estate, not someone whose primary business is selling coaching. Ask to see how they underwrite deals, how they handle downside scenarios, and whether they’re willing to tell you not to buy something.

    From the tax side, I’d start planning the ownership and estate structure early. If the long-term goal is leaving the portfolio to your children, that involves more than simply putting properties into a trust. Entity ownership, depreciation, basis, estate planning, and how the assets pass at death all need to work together, ideally with both a CPA and estate-planning attorney involved.

    You’ve already learned what overexposure can look like. This time, I’d build the portfolio so one vacancy, one bad year, or one financing problem cannot put the whole plan at risk.

    Feel free to DM me, I’d be happy to send over a few resources that might help with rental underwriting, cash-flow planning, and building the tax side correctly from the beginning.

    [email protected]941-914-7779
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