How I Went From Broke Poker Player at 25 to Millionaire at 31

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It’s a strange thing to think back at going broke and realize it was handedly my greatest lesson and an overarching asset in my life. Today I own 83 rental doors. I’ll begin by telling you how things went wrong, how I turned them right, and how I became a successful real estate investor.

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The Fall

I began attending the University of Central Florida with a full academic scholarship, but lost that scholarship in year two, after taking a hiatus to day-trade stocks. My natural linear progression at the time ultimately led me to the online poker craze. At 23 years old with $100,000 spread across the internet, I was invincible. I was never going to work a regular job.

To poker fans, or to those who remember the movie Rounders, I was a “grinder.” A grinder is risk averse and generally waits for strong cards, relying on his opponents to make that assumption. My strategy was to be calculating, to play the endurance and position game to outlast my opponents. But I never learned how to lose well. I was too competitive and immature to immediately compose myself when I lost. Poker players call it going on tilt when players become emotional and reckless. I couldn’t handle the tilt. I tried to make my losses back at higher-stakes tables. In hindsight, it was a terrible idea. It is the real estate equivalent of adding to an over-leveraged position with more bad debt.

The online poker world changed when payment processors froze player funds. My world changed as well, and in time my bankroll vanished. I distinctly remember sitting in my apartment in Orlando, wondering what I was going to do in life. Twenty-five years old, and with $35 in my bank account, I had to watch what I was buying for dinner in fear of an overdraft fee.  It was time to go back to college, get my degree, and get a job. First, though, I had to figure out how I was going to pay rent.

Related: The True “Get Rich Quick” Scheme: How Being Broke Allowed Me to Succeed in Real Estate

Learning Humility

The same guy who had been buying bottles of liquor at the night club was now filling ice for the bartender. Working as a telemarketer by day and restaurant barback by night, I went back to school with two jobs to pay the bills. This was a profound lesson in humility, and one I’ll never forget.

Seventy days went by without a single day off. I can still feel the pain in my feet after a long shift and remember rubbing them in agony. If I had another chance at business, I needed to make it count. The chance finally arrived one day – day 70, in fact – when an old friend called and offered me what would become a life-changing opportunity. My friend had built and owned a marketing company and had recently fired his manager. He needed someone to help with the day-to-day running of his business.

The past few years had humbled me. I went back into grind mode and worked 70-hour weeks. My goal was to become irreplaceable. In the second month, I realized a way to tweak his business to increase profits and offered a suggestion that ultimately doubled his revenue. I was later tasked with analyzing and negotiating most deals. Two more of my ideas were implemented over the next few years. His business was now thriving, and I was rewarded handsomely. From scooping ice and sweeping floors to managing operations at a thriving business, I went from borrowing to pay bills to investing disposable income. I was about to discover my new passion for real estate.

My First Real Estate Purchase

My first real estate deal was not far from what people call house hacking (at the time, I didn’t know the term). I bought a condo with cash on the intracoastal in Boynton Beach, Florida, for $95,000. Rent in Orlando was $1,000 per month, and I was collecting $950 in cash flow from the property. In full disclosure, I bought the condo without knowing the potential of real estate investing. Now I know. I was able to save money and hoard cash at a pace I had never experienced. I was hooked.

From One to 83 Units

After the intracoastal property showed me the power of cash flow in tangible terms, the mission became to scale. Eager to never feel the broke feeling again, I was running away from that fear and running toward cash-flowing properties. My wife and I purchased a home in Delray Beach, and I had already started looking at investment properties to purchase in the area for more cash flow: another condo, but this one with significantly lower HOA monthly dues. So I bought an REO from a bank for $85,500. This unit currently rents for $1,450 and would appraise around $200,000. These two units essentially paid the mortgage for our home, and I was already saving for the next investment. A bit tight on cash, I sought out a partner to split the purchase of a distressed six-unit building.

Related: How to Get Rich: 7 Awesome Ways to Build Wealth Today

Anyone who is familiar with Southeast Florida knows the stories of rampant abuse of rehabilitation facilities. I had lofty aspirations. I wanted to take one that was located near a terrific park next to the ocean and convert it into rental apartments. We purchased the property for $355,000, spent $40,000 on rehab costs, and turned the building around. It has doubled in value and cash flows phenomenally. We self-manage the property and take immense pride for playing a role in gentrifying the area. Over a three-year period while operating the rentals, I went the Dave Ramsey route and paid off any debt possible.

Today I own the rentals outright with no debt. With the current structure in place, we decided to now seek out larger mutlifamily properties. With minimal debt and significant equity (I had also been investing in the stock market and alternative investments) securing agency debt was a challenge and an excellent learning experience. Freddie Mac took a fine-tooth comb through our lives, financial track records, and the deal on a 74-unit apartment complex in Memphis, just outside of Germantown. It has been an amazing experience operating at that level, and I now have bigger plans of expanding to other regions and larger deals. But I’m still a grinder. I don’t want to go broke ever again.

Who I Am

I’m a husband, and a father to a son with another baby boy on the way. I have goals for the next three-to-five years to acquire 1,000 doors, and I will relentlessly pursue the goal to completion. Then I’ll pick a new number. Constantly striving toward personal growth, I try to get through a book per week on business, investing, or self-development. I’m a true believer in building bridges and trying to add value wherever possible. But regardless of the financial success, I know I have a lot to learn and approach life in a humble fashion.

I still get dirty and do physical labor at properties to stay grounded. I’m still a grinder, worried to lose it all. People often consult me to analyze properties, and I am more than willing to help in any way possible. Anyone can feel free to reach out at any time for objective real estate or business advice and I look forward to sharing my thoughts with this community.

We’re republishing this article to help out our newer readers.

How has real estate investing changed your life?

Let me know in the comments below!

About Author

Gus Ross

Gus Ross is a managing member of Ownup Capital. An accredited investor with goals of expansion, Gus is always evolving strategies for acquisition and analysis of properties throughout the country. An avid reader and seeking to learn and grow everyday, he has ultimate goals of philanthropy, business, and personal growth. A visitor at local REIA meetings, he is always seeking to network and meet investors and align goals and interests. Ownup Capital


      • Hi Gus, Great article!! I have approximately $70k saved up to purchase my first investment property. I am living here in South Florida, what areas are looking good to invest in here? I feel like Miami is getting overpriced? What financing strategy did you use to grow your portfolio?

    • Rebecca Jackson

      That’s an incredible life! It reminds me of a quote out of “The Last Lecture” by Dr Randy Pausch. He described obstacles not as a way to keep you out, but to keep out those that don’t want it as much.
      Your story proves that even with $35, you can find opportunities to make good things happen if you choose to.

  1. Braden burton

    Gus, what is the timeline to get to 83 units? You did this in just a couple years? I’m working on my second deal and often feel like I could be doing more. I know it takes time and I’m reading, learning and growing everyday. I know things are going to start to grow exponentially but wondering what the path looked like for you, and what timeline you went from 1,4,8 to 83. Thanks for the share!

    • Gus Ross

      It took 4-5 years but as is anything in investing, a lot had to do with luck and timing. One of my favorite books is Fooled By Randomness. I highly suggest it for an investing. I got lucky to turn my finances around in an up-trending market. With diligence and persistence, opportunity can be created so stay with it. If you ever seek advice or ever want an objective opinion feel free to reach out. I’d like to help as many people as possible. Without some assistance, I’d still be a telemarketer.

  2. Michael Steven Harris

    I was moved by your story I have one of my own I hit bottom two years ago, went from homeless to social services to where I am now. I am on track to go to law school and I have my eye on the joint JD/MSRE program at University of Florida. Ever since going back to school I have been a straight A student working at a restaurant to pay the bills on my public housing unit. Keep going stories like your inspire those without hope.

    • Gus Ross

      Motivation can come from strange places. A passionate speech by a man named Rick Rigsby went viral recently and in that speech he said something along the lines of “rock bottom can become a great foundation to build on.” Business and life have to do with perspective and mental fortitude. Please message me your email so that I can send you a book that I think may help in your journey.

      Both of our stories are still being written. If there is any way I can help you along the way please reach out to me.

      • Ozzy Guzman

        Hey Gus, I am recently knew to Bigger Pockets and stumbled upon your story. Actually the first time to ever post anything. I am 27 years old and work in the REO preservation field and i find your story extremely inspiring. As i am no where near your level of success I cannot wait to get there one day. I want to thank you for mentioning the speech by Rick Rigsby. I looked it up and all i can say is WOW and Thank You. Came at a perfect time for me. I am stuck at a 50k a year job and in desperate need to do more. I know that i am capable, just dont know where to start.

  3. Kalyanii Kennedy

    Thank you for telling us your story. It’s very inspirational. I lost everything I had back in 2009 to my house forclosing and was homeless, got a divorce, and had a toddler to care for. I went back to school and have been able to dig myself out, but it took a lot of fortitude, planning, and thick skin. I hope to one day be as successful as you and the others on BiggerPockets so that I can help others. Your story gives me inspiration and hope for the future. Thank you so so much.

    • Gus Ross

      Kalyanii, you have the toughest job on earth. Raising a child is way more difficult than real estate. I always remember to tell my wife that she has the tougher job between us. Having just read what you wrote, your success is going to be a matter of time if you stay with that fortitude and thick skin.

      If you ever need advice along the way, feel free to reach out. I wish you the best of luck writing your own story.

  4. John Murray

    I’m a multimillionaire grunt too! My story took a bit longer to come to fruition but fruition it did. To make the jump from employee to entrepreneur was the most exciting time of my life, even more exciting than military success. Today I’m going to cut and fit HardieBacker, rock in the free world brother!

  5. Jiri Vetyska

    Great story Gus!
    I have a similar story, although I didn’t have a friend with a successful business asking me to run it (most people don’t). Lost everything in 2001 and was underwater in 2009, but staged a comeback in 2013. Without easy cashflow, it’s years and years of work and slowly acquiring properties.

  6. Charles A.

    Great story.
    I’m just trying to really work the timeline like someone earlier asked.

    You managed to pay cash for two $100k~ish condos and paid off a $355k debt in 2-4 years?

    The great break you got at that guy’s business must be darn well-paying….at least half a million a year.
    Or that math becomes difficult…

    • chad nagel

      Agreed, Numbers dont lie. Cool story bro. But show us some numbers. You went from $35 in bank and single to married with 95k cash to purchase. This would show a story to surround your self with rich friends with businesses then invest your W2 job cash into real estate. NOT how to invest with no money down.

  7. Jenn N.

    What an inspirational story! Thank you for sharing. My husband and I were, like many others, hit hard by the recession. We barely hung onto our properties in CA by cutting back on everything to the point of moving into an RV (It was great fun and taught us a lot). We finally sold them in 2015 and 2016 and have begun investing again in CO. I’m trying to learn as much as possible. Would you mind sharing your favorite books? I took note of the one mentioned above. Thank you! 🙂

    • Gus Ross

      Jenn that is awesome! Here is a list of great reads I love:

      Fooled by Randomness
      The Most Important Thing
      Principles: life and work

      Great books on understanding risk and investing that applies to real estate.

      Please message me your email. I’d like to send one to you and your husband.

  8. Isaac Antoine

    Beautiful Testimony, although you could’ve given up or remained stagnant, that was a reminder and really allowed you to be helpful, impactful and changing the neighborhoods you buy in.

    Do you still buy the houses and pay the debt quickly? Or Do you leverage credit /equity?

    • Gus Ross

      I’d like to get into bigger multifamily and am planning on leveraging. Though I am extremely risk averse and comb all deals with a fine tooth comb. I have an offer out there for 76 units with local REIA meetup guys that I met on Bigger Pockets so I’m open to doing deals in any form or fashion if they make sense.

  9. John Glaze

    I have to agree with most other posters very inspiring story. I’ve been driving for dollars for at least a year and watching my local market for over two and haven’t had any luck making a deal happen. I want to start out with at least for units but have to owner occupy one to make the deal the best I can with a va loan as I’m on limited income from military service disability.

    • Gus Ross

      John I love to hear you’re driving for dollars. Right now is a tough time to find deals but they are still out there. If I can offer any value in analyzing properties for you or help in any way please reach out. Best of luck and thank you for your service. Without guys like you you none of us could invest.

  10. Mary White

    Thanks for the well-written article. I find it interesting that you’re a Dave Ramsey follower since both of you pushed too hard and went broke, then found success in business and real estate afterwards. We were accidental landlords at first and it was the best thing that could have happened. We discovered the power in real estate and gained the strength to take big risks for big rewards. Best of luck in your pursuits!

    • Gus Ross

      Thank you Mary … I went the no debt route because of life circumstance and fear. Investors should place their money based on their goals. In hindsight I could have scaled bigger by leveraging, but it was a great learning experience and allowed me to feel a great amount of security. It still does. Though next cycle, I may take a different approach without getting ahead of myself.

  11. Gus Ross

    Took 7 years Jared because of all the serial entrepreneur failures, but I beat the U Cant Finish brand. Was great to get the degree but unfortunately it’s an expensive piece of paper on my wall now. Best of luck to you, and if there’s any value I can add to you feel free to reach out anytime.

  12. Jim Celmer

    I was wondering if you pay yourself a salary for the earned income. So you can fund a retirement account(401-K,Roth)? I just retired from my job and will only have passive income now. I was debating on paying myself a salary or not? Another question please? If the tax reform(ha.not much reform IMO)passes. how will it affect real estate investing? Thanks Jim

    • Gus Ross

      Hey there Jim, that one I’d refer you to a greater mind than myself. Your question would be an awesome post for a CPA on Bigger Pockets. The answer will probably be a circumstance to your entire financial picture.

      As it relates to tax reform … I’ve heard numerous whispers but there is no final bill. Speculating on the final product is probably a waste of time and out of any of our control. Let’s wait until the final version and see how to navigate those waters. I pay attention to it daily though so let’s circle back when the time is appropriate.

  13. Mena George

    Thanks so much Gus for the amazing inspiration article !!
    I was in a similar position several years ago and lost a lot of money but now I have kind of stable cash flow and some savings and I’m looking forward to start investing again the right way away from the day trading and gambling !!
    But I’m still afraid to lose it all … again !!
    I’m still worry to buy any real estate or stocks or even bitcoins in this market or with these prices so I preferred to sit on the sidelines for a while now.
    Any advise for me ?

    • Gus Ross

      Thanks for the comments Mena! I think the distinction here is between being risk averse and weary to pull the trigger. Deal flow is certainly an issue lately but there are still deals out there. I wouldn’t be discouraged if you can’t find deals right now but would encourage you to keep looking and don’t give up. Persistence will lead you through the slow times. If there’s anything I can offer in terms of value or advice please feel free to ping me.

    • Gus Ross

      Hey there Danny. It was through a third party that sourced the deal. There are tons of commercial loan brokers looking to lend on deals like this and I’d be happy to refer you to a few folks if you’re interested? Ping me if so

      • Mike G.

        @gus Ross Gus first of all what a inspirational story. Complete turn around and how you scaled in REI so quickly is amazing in it self as well. I am coming out of a bad period in my life as well and have the W2 and I’m looking to scale and get a few cash flowing properties under my belt for buy n hold. I would be interested to be referred to the loan brokers that lend on multifamily deals if you would be so kind. Thanks for the inspiration

  14. landa price

    Inspiring article. much congrats on your wondering how you got from Florida to Tennessee with the acquisition in Germantown? Did you know someone there, or just pick up the phone and inquire of local re person? Am asking because I don’t want to invest where I live, but prefer to invest out of state which makes it difficult to find properties.

    • Gus Ross

      Hey Landa thanks for the questions. My partner and I prospected the area and flew out there. We had market research that honed in on the area and from there starting picking up the phone and calling brokers and property managers. It was months of due diligence that ultimately paid off.

      If you have any questions, feel free to ping me and I can explain further.

  15. Casey Rumfelt


    Great Post! Thanks for sharing.

    I love that you mentioned ole Dave Ramsey. I follow his principles but it’s not easy in this game especially getting started. I was wondering if you had any recommendations on maybe a safe debt ratio to get the ball rolling or is it truly better just to save and buy everything outright? Or do you go on the other side of the spectrum and just go all in and embrace the debt?

    Thanks again, looking forward to hearing back!

    • Gus Ross

      Hey Casey, I think the answer is circumstantial to your situation. Because of my past financial situation I wanted to remove any debt and fear of owing the banks money. In hindsight it was a mistake if my ultimately goal had been to acquire more property. I don’t regret it at all because I know in a downturn I can sleep at night like a baby =).

      I can’t really quantify a safe debt to income ratio but would say to leverage where you feel most comfortable and that varies from person to person. Feel free to ping me to discuss it in more detail.

  16. Great article!

    Gus has been a close family friend for many years so I can speak from experience. Me and my family can always count on him to give us valuable input on most financial decisions.
    In fact, the one bad real estate investment I made was when I foolishly went against his advice. Lesson learned!
    He has a true knack for business and a real passion for offering sound advice and helping others achieve success.
    We have only the highest praise and appreciation for his guidance.

    Wish you nothing but continued success!

    • Gus Ross

      Thank you Yaniv! The unit is gorgeous anyways and the market will come back. Your kind words bring more professional pride than money can buy. Our bond is a life-long one and there will be plenty of fruitful decisions ahead.

  17. Luis Vilar

    Amazing! I have a similar goal. I am in South Florida as well. I’ve been looking for my first deal for a couple of month now. This is a tough market. I’ll love to hear some advice from you on how to approach this market and how to make it, since you are doing great.

  18. Caleb Pendergast

    HI Gus! Thanks for sharing your story, it’s always insightful to see where other people have come from and how they got to where they are today. I am currently living in Sanford, FL. I just finished highschool and I’m a bit unsure of what to do. I have been very interested in real estate investing for the last 2 years and have been trying to learn everything I can online. Was wondering if you would be interested in going out for lunch or to have a coffee.

    God bless you

  19. John Ferrughelli

    I also agree, awesome story.

    Although some of the details have been glossed over, like how you went from 1 to 83 doors so quickly and the original condo was bought in cash for 95K and rents at 950 per month – you still haven’t made your money back on that original property because it would take over 8 years at 950 per month.

    Perhaps I’m getting too hung up on the numbers, but I’m fairly new at this so I am trying to figure out how the numbers work.

  20. Megan Clancy

    I love stories of people who “made it” starting with immense debt/nothing at all. I’m heavily in student loan (by my standards at least) and recently took the plunge into RE full-time, leaving my day job and therefore my W-2 income (and subsequently “easy” access to financing) so these stories give me hope and keep me focused to grind through and meet my goals too. Good luck!

  21. Nima Mohajeri

    Hi Gus, really great post. I currently have two properties I rent out, one condo in CA that breaks even but I assume will appreciate over time, and a triplex in Tucson which is pure cash flow. I’m short on cash now though, but really want to get to the next level. Any recommendations besides saving? At the rate I’m able to save from my current job, it’ll take me a couple years to be able to buy anything else…and I’m sure you understand, I simply can’t want wait that long!!! Thanks in advance.

  22. Alex Romoser

    Thank you Gus for putting your story here, and for being an inspiration.

    I have many takeaways, but something practical I’d love to hear more about: What does your day to day life look in order to aim for reading one book a week? (Audio books at the gym, an hour reading every morning, etc.) I’d love to pick up any of your tips / hacks, because this would be a very worthwhile habit for many of us on BP!

  23. Christopher L Hall

    Love the story Gus! I am a 41 year old looking for my first deal, reading anything I can find in the internet. Getting ready to hit my first REIA group meeting in my area. I have worked for someone else my whole life, and as a cook it is usally some guy who thinks his way is the only way, so I have made the decision in my life that working for others is not what I want. Love how you pointed out that “Rock Bottom” can be a good foundation to build success on. I hope that one day I can help someone out with their goal as you have with me. I WILL NOT GIVE UP ON MYSELF! If I could I would love to read that book you have offered to send people. with that thank you very much for sharing your story.


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