Posted over 5 years ago

From Miserable Lawyer to Full-Time Real Estate Investor: How I Did It

Going from lawyer to full-time real estate entrepreneur was tough. Here's how I did it.

Trading My Life for Money

I practiced law for 12 years. I worked 14-hour days, ate every meal at my desk, and worked most weekends. Sometimes I went a month without a day off. I ate terribly, got fat, and felt miserable. I hardly dated or saw friends. My life consisted of eating, working, and sleeping (very little). The money was good. But my “Sunday night blues” started on Friday night. I wasn’t just trading time for money, I was trading away my life.

Why was I working so hard? So my faceless billion-dollar corporate client could fight over millions of dollars with another faceless billion-dollar corporation. And, right before trial, they'd always exchange some money and settle. The client would go right back to doing business with the enemy. I'd have just wasted three years of my life.

And, for what? To make partner? Yeah, right. Law firm partners don’t like to dilute their profits. And even if you make partner, then what? You work just as hard as the associates, except now you have to bring in business too. The pressure never stops. You have to feed the machine clients or it stops dead.

I tried to escape several times. I walked off the job with no plan. I just needed out. But, with no plan, I would drift back into law. I even went back to school for two years. Then I met my wife and returned to law for the money. But law firm life nearly destroyed my marriage.

In 2008, the Great Recession hit. I was grateful to have a job. But the work dried up, and as it did, my stress level rose. I surfed the Internet all day, dreading a knock on the door that meant someone was firing me or bringing me work. I could not decide which was worse.

Breaking In Nearly Broke Me

In early 2011, my firm got tired of paying me to surf the Internet and let me go. I was more relieved than upset. But the idea of interviewing for another law job made my stomach turn. I had to make a change. I’d always been interested in real estate. A friend and I had looked at properties together but had not made any offers. I started looking into real estate as a career. But, because of the recession, I was competing with guys out on the street with years of experience. I stood no chance.

One day, a very experienced real estate hand sat me down over coffee. “Look,” he said. “I’ll tell it to you straight. At your age [42], and with your background, no one in this city is going to hire you. The only way you’re going to break into this field is if someone just takes a liking to you and offers to make you their partner.”

Unbelievably, a few weeks later, that happened. I had been networking with everyone I could in real estate. I met a woman who owned property with her husband and wanted make real estate a business. She asked me to join her. “This isn’t rocket science. You’re smart. You can learn it,” she told me. “And, you have integrity. I can trust you. That’s most important.” She also thought I could raise money.

She must have had some kind of second-sight. I was not sure whether to accept her offer, so I asked some close friends for advice. Two of them told me that, if I accepted the offer, they would invest money with us. And the amounts they mentioned were substantial.

So, having a partnership offer and two investors in hand, I decided to go for it.

It was not easy. It took us more than a year to find our first deal. Then we found another from the same seller. But after we had spent money on due diligence costs, travel, legal fees, lender fees, etc., the lender backed out of one deal and we terminated the other. We lost months of work and tens of thousands of dollars each. And I was supporting my family out of savings at the time.

We decided to break up the partnership. We’d had some disagreements over strategy and decided at this point it was best to go our separate ways.

After Three Tough Years, Success at Last

Now what? I wondered.

A few weeks later, I was having dinner with one of my investors. I said I might have to go back into law. He said not to be hasty and then suggested that we form our own venture. In early 2013, we founded Two Bridges Asset Management LLC. It took a year to get any traction. But by 2015, we had four properties in our portfolio, comprising 404 apartments, worth nearly $20 million. Now we're planning to raise our first investment fund.

What enabled me to leap from miserable lawyer to full-time real estate entrepreneur?

  • I exercised a high degree of professionalism, which I learned as a lawyer
  • I established a reputation for intelligence, integrity and trustworthiness
  • I networked actively with people in the industry and followed their advice
  • I absorbed the losses personally when our deals went bad, rather than look to our investors, demonstrating integrity and commitment to the business
  • I kept moving forward in the face of setbacks
  • I said yes to opportunity when it came my way

If you are committed to a career in real estate, and you develop these traits, too, you can free yourself from the corporate grind. I did it. So can you.



Comments (22)

  1. Came for the article, stayed for the comments from other former lawyers who turned things around. Thanks for the Thursday inspiration!


  2. First of all, thanks for posting this story, it's so inspiring!  It gave me a good laugh to hear of your misery. You've painted such a good picture.  I'm in a similar situation at 48 years old. I work at a high paying job that I'm not in love with and am trying to "Shaw Shank" my way out.  However, everytime I get something going, something kills the deal (seller backs out, buyer backs out, etc.) I used to own about a dozen properties but some "newbie mistakes" caught up with me and I went thru a bankruptcy.  Learned a lot and definitely don't regret it.  I'm a member of a Real Estate club, am conversing with and building relationships with the right people, I have experience birddogging, wholesaling, light rehabbing, and I read constantly. I've even held a mortgage before.  The only problem is getting and turning the deals!! It's been about two years now since I've been to the closing table. It's so frustrating, but I keep on pressing.  Thanks again for the story.


    1. You're welcome, David.  Thanks for the nice comment!


  3. Congrats Jonathan for your success so far. Your story is so inspiring. I can relate to your story as I'm a Chartered Accountant and worked for several years for a big four accounting firm and for the banks. Now I own my own practice and do real estate on the side here in Canada. I agree with your advise on engaging professionals. I'm currently looking for a lawyer to help set up my corporate structure in Florida for my US real estate business so if you know someone you can refer I would appreciate that. More success to you!


    1. If the lawyer does not need to be in Florida, then I can recommend the person I use here in New York.  Please private message me.


  4. Congratulations.  I too am a lawyer with a similar story.  Left big firm practice and followed my dream of investing in real estate.  My partner and I own 400 apartment units and manage another 1000.  Would never go back.  Persistence is key.  Good Luck to you.


    1. That's awesome!  Congratulations on that success!


  5. Many thanks for this post - as a young person about to become a trainee attorney, I am already feeling the pressure you mention. I'm very keen about getting into REI, particularly the MFRE deals you talk about in other blog posts. It's good to know that the transition is possible!

    Quick question - how much do you feel your background in real estate on the legal side helped you in your investor-side endeavors? I'm wondering how much exposure I should be looking to get, as most firms here focus on the 'faceless' corporate clients.

    Thanks for the great post!


    1. Being a lawyer helped in real estate insofar as I knew how to be a professional and how to be client-facing.  I also understood how important your role is as a fiduciary, so I knew to put investors first.

      As far as the legal side of things was concerned, I knew enough to know what I don't know -- as well as how essential proper legal advice is.  So many people on BP want to take short cuts and avoid using lawyers because they just think it's an expense.  But I am a lawyer, admitted in two states, and I would never do my own legal work, because property law was not my speciality as a lawyer, and neither was putting together the corporate or securities documents for a syndication.  People who think that they can do this themselves or just using Legal Zoom are in for a very rude awakening if things ever go wrong.  So I always advise the use of a properly trained attorney in these deals.  It's real business.   Professionals treat it that way.


  6. This is a very insightful piece, Jonathan. I, too, am a lawyer, but I am trying to see more opportunity in my employment. I am a tax attorney, by trade. I am taking this opportunity to learn as much as I can from the job - i.e. how to engage in appropriate tax planning through corporations, partnerships, and LLCs. In the interim, I am also investing in real estate and learning how the tax code can help a sole-proprietor and the individual investor. I hope to take the knowledge from work, and eventually branch out solely into investing in real estate. I'm glad to hear that you were able to make that leap, and that that is a possibility for me too, eventually! Please keep me posted on how your investments keep growing! Looking forward to following your journey, and taking notes, along the way!


    1. Thanks, Lani.  Great to hear from you.  Good luck on your journey from lawyer to real estate investor.  There are a lot of us out there!


  7. Great article.  What I learned from you is to never give up, even when things don't look promising.  This is the kind of motivation I need to persevere in my real estate career.


    1. Just keep going. Half of business success is just showing up every day, no matter what happens. Plug away!

  8. Jonathan thank you for sharing your story. 


    1. You're very welcome! I'm happy that you enjoyed it and found value.

  9. Thanks for sharing Jonathan.  I am glad you found success in real estate investing and look forward to reading more from you.

    I am sorry your legal career was such an unhappy one.  My experience has been the opposite.  While it is a stressful and demanding profession, I love the law and look forward to practicing for many years to come while I build wealth through investing with passionate real estate professionals like you.

    Keep up the great work and thanks again for inspiring us to greater endeavours!


    1. Brian,

      I heard a rumor that there was a happy lawyer out there.  Must have been talking about you!

      But seriously, I am glad to hear that you love the law, and that you are happy.  It was not the right career for me, but that does not apply to everyone!  Glad you liked the blog post!


  10. Yes, very inspiring indeed. Thanks for sharing Jonathan. 


    1. Thanks, Joe!


  11. What an inspiring post, Jonathan, thank you! Most people focus on the opportunity of investing (and there IS a lot of it) but they fail to realize the work that goes into it... most would not have stayed with it for as long as you did. Congratulations on tapping into a perseverance that few possess, and for seizing the opportunities that came your way. All the best in years to come!


    1. Thanks very much, Kent!  I appreciate the compliment.  Glad you found it helpful!


      1. The more reasons I have to keep going. Thanks.