When the 500-Year Flood Arrived

In my world of real estate lending, uncertainty and economic turmoil are the norm.  When evaluating the best way to mitigate or hedge risk from loss, as part of the due diligence process, a prudent investor runs at least 3 different potential outcomes: (a) the “base case” scenario where results are more in line with expectations, (b) the “worst case” scenario in which the results are much worse than expected and (c) the “best case” scenario in which the results are much better than expected.

In real estate when you buy a home near a river or stream that falls within a flood prone area FEMA provides homeowners with some form of catastrophic insurance from events that occur within the “100 year flood plain”.  For homes in much lower risk areas less because they are farther away from a river or stream FEMA also has a separate classification called the “500 year flood plain”.  FEMA never considers that to be much of a risk because, well, they don’t expect a flood to occur in this area more than once every 500 years.

So with full knowledge of these risks, combined with more than 25 years’ experience in real estate law, commercial lending, workouts, foreclosures and investment banking I decided to form a bridge lending platform to make short term, commercial bridge mortgage loans in 2005. I  partnered with 2 very sophisticated individuals, one of whom had been a public bank CFO for more than 2 banks that were bought out and the other had a 30 year track record in fixed income sales.  We invested more than $2.5 Million in our company to ensure our investors that our interests were aligned with theirs. I thought we knew more than anyone and with such complementary skills we would be very successful and, from 2005 until mid-2007 we were very profitable and growing.

While the money was important to me, it was not my primary motivator; my professional reputation was. I wanted to prove to others that I was a smart, successful and profitable entrepreneur.  My personal ego trip.  My objective was to make our commercial real estate bridge lending business a professional operation with written guidelines, committees, forms, lawyers, accountants, etc. In other words a really professional operation.  My goal was to combine intelligence, experience and professionalism to create a profitable and reputable business that treated its borrowers and investors with respect.

We never made loans to consumers or took mortgages on primary residences.  We never wanted to throw someone out of the home.  Commercial real estate was different-it was pure business.

My partners and I raised more than $10Million in capital and then secured a $40 Million warehouse line from a large money center bank.  We were returning more than 14% net to our investors and growing by leaps and bounds until June or July 2007.

That’s when the 500 year flood hit.

I remember waking up at 5 a.m. and turned on CNBC and was shocked to hear Lehman Brothers had filed for bankruptcy.  I was concerned but not that much because Lehman’s problems stemmed from the subprime residential mortgage crisis and we were in the commercial mortgage lending business.  In my feeble mind, there shouldn’t have been a correlation between residential and commercial loan defaults. Then a tsunami started forming and Lehman’s demise was quickly followed by Bear Stearns, AIG, Countrywide, Merrill Lynch, Fannie Mae, Freddie Mac and many, many others.

My world was crumbling around me and for the first time in my life I felt truly helpless.  I started working day and night to try to find solutions.  My warehouse lender called in a workout specialist who, after spending a week poring over my loans, concluded there was nothing he could do to assist.  I vividly remember him telling me “let it go… you’ve got to move on”.

It’s easier said than done.  Shortly after the dominoes started falling, my partners walked away leaving me to handle the mess with investors, lenders and borrowers.  The investors were my partners’ friends and family and he left me to clean up the mess.  I realized that he was distancing himself from the mess we created so that at the end of the day, he had moved on and reinvented himself.  I couldn’t do that.  I had taken investors’ funds and I was determined to do everything in my power to recover as much as I could for them until there were no more options.

I spent 2 years of my life working for free to save my reputation and recover funds for my lender and my investors.  The next 18 months my lender was paying me to liquidate what was left of the portfolio.

At the end of the day I bought a lawsuit against an attorney (not mine—it was one of my borrowers’ attorneys), spent $50K of my own money advancing legal expenses to bring the case to trial.  After being deposed for 8 hours and spending an additional 7 months of my life, we settled the case for almost $1.5 Million.  After the attorney took his cut I was left with $990K

You know what I did with the money?  I wrote checks to each of my former partners and told them I was sorry I couldn’t have collected more.  I never told them that I bought the lawsuit in case we lost.  I needed to manage expectations.  If we lost it would have been another $50K down the drain.  I kept $40K which is the amount I would have received had the partnership still been in existence.  I didn’t have any obligation to tell my investors anything about this and didn’t have to give them any money.  But I did anyway because I couldn’t live with myself if I profited from them at their expense.

I’m not sure I’m ever going to recover my self-esteem or reputation.  I’m now in my mid-50s and I’m unemployable, overqualified and can’t seem to shake this disaster.  I would appreciate some sage advice on how to overcome my perception that I’ve permanently destroyed my professional reputation.  Thanks for reading.


  • You have karma on your side my friend.

    What you did was honorable. I know that doesn’t pay the bills right now, but at the end of the day, I bet you can sleep well at night.

    With all of the repairing you did, do your old investors still have faith in you? I know nothing about the real estate market, but as an outsider, it feels like it’s strong. Can you not go back into lending?

  • Thanks for the words of encouragement. I may try.to find some new partners and re-enter that market. I have to have the confidence in myself that I can successfully run this business without allowing past history to affect my decisions. At the end of the day I think you’ve helped me realize that my confidence level will increase with the right partners. That’s a good first step. Thanks

  • What you did was absolutely the right thing to do. All the work did to put things right, will buy you a whole lot of love down the road. It just may not seem like it now.

    Read this; http://www.forbes.com/sites/amyanderson/2012/11/28/success-will-come-and-go-but-integrity-is-forever/ If you have any doubts you did the right thing, this will reinforce your belief system.

    Reading between the lines; it seems you know your industry well, you made a success of it before the downturn. Then had an very difficult period putting it right / patching up… ON YOUR OWN!

    Not all investors will admit this, but having been into battle actually makes you more worthy of investment. If they had a choice of putting their money into you or your former morally bankrupt partners – Who do you think they will go with?

    With the knowledge and additional skills you have gained, why not skip the slick guys and do it yourself. Build a team around you, take some money from investors but try to retain as much control as possible. As it seems you have the right tools and major ownership will allow for you to determine the integrity of the company.

    You may be in your 50’s but you have been there once and getting back could be far quicker than a first timer.

    Get your confidence up and jump straight back in… Good luck.

  • The amount paid to the partners who walked away should have been discounted reflecting the loss their absence created. The funds spread out to the investors. It should be important to communicate the lack of diligence from the partners their rep should suffer.

  • Thank you all for your input and encouragement.
    One inadvertent omission from my original post. I’m not trying to pile on to my misery, I”m just trying to provide a better picture of the unrelated stresses that affectt my decisions so I can get input from an informed audience .
    In 2007, while my business life was falling apart in New York, my wife of 30+ years unexpectedly and inexplicably developed 3 different autoimmune conditions (Fibromyalgia, Sjogren’s Disease and Reynaud’s Syndrome). The symptoms caused her so much widespread pain that she went from running 5-6 miles a day to spending 16+ hours a day in bed medicated on opiates to manage her pain. After 2 years of living with constant pain which she describes as “having someone strike a match, light her body on fire, and keep the match continuously lit) her doctors told me my wife had to move from the NYC area to the West Coast (Santa Monica) because the changes in barometric pressure on the East Coast were exacerbating her pain.
    While she’s much better now, I had to sell our 3000 sq. ft. condo, move across the country and find a place for us to live while I was going through the business meltdown. When we arrived in LA, I was still working 15 hours a day (at home) because most of my days were spent taking my wife to different doctors. For the first 2 years after she moved to LA (without me) I was, commuting between NYC and LA, because I wasn’t sure if her condition would really improve in LA and I didn’t want to uproot our lives permanently if her improvement was only goiing to be temprorary. After 2 years of commuting I finally had to move to the West Coast.
    She’s now much better. About 18 months ago I almost lost her-she went into septic shock and had to have emergency surgery to save her life. We’ve been married for 37 years but now that her condition is under control it’s a little more difficult evaluating new partners because I never really developed trusted partnerships in LA when I was working in NYC.
    I’m not complaining and don’t resent or blame my wife for any of the decisions of troubles we’ve encountered the last 7 years. I’ve learned that what doesn’t kill you makes you stronger. I now know that I can’t move back to the East Coast due to her medical condition but I’m a lot less confident about re-entering the market on the West Coast because have no professional acquaintances in LA and therefore no friends or potential partners with whom I have any trust or confidence. Any suggestions about how to find a trusted partner whose skill sets will be complementary and add value to the new venture?

  • I have a good friend who had taken over $200M of investment in real estate that was unwinding in 2008. He had made numerous personal guarantees and was continually trying to work out new deals to save his investors money. Just this year he finally filed for personal bankruptcy and wishes he had let it all fall down back in 2008 so that we would be back on his feet now.

  • Thank you for sharing, your story is strangely motivational. And I can’t imagine that your reputation is irretrievable, given your story. If you do start up a new venture though, I think either a) you are taken advantage of and the SV industry eats you alive, or b) your honesty and character helps you build a truly great company (not just a product). I hope its b, because that’s the world I want to live in.

    I am also older than the typical SV startup kid (30’s, wife, two children) but I’m planning on leaving a tenure-track professorship to start a company. If you want to chat, trade notes, drop me a line at: svyhr@thecloudindex.com. (I have no idea how I’ll be able to tell if it’s really the original poster, but nothing ventured nothing gained, right? I’ll dispose of the email in a day or two regardless.)

    Thanks again for sharing; I think someone with your character and integrity deserves a co-founder with the same. And I think investors are (not so secretly) looking for founders who are bit more mature (in morals, if not age).

    • SVYHR…thanks for the words of encouragement. Given my background the one thing I’m not worried about is being eaten up alive by SV industry. I used to swim with the sharks.

  • If you think this was a “500-year” flood, you’re doing it wrong. As we have more and more commerce, debt, political strife, etc. These things are going to be happening more often, don’t be naïve and think that it could never happen again in your lifetime.

    • I must be doing something wrong which is why I didn’t succeed.
      However, I do think think the last 5 years fall into the category of the 500 year flood. When was the last time you can recall 3 major global investment banks going broke (Lehman, Bear Stearns and Merrill Lynch, the latter qualifying as a “shotgun wedding” with Bank of America compliments of the Federal Reserve) , a federal bailout of a major insurer (AIG) and one or two national banks (Like Citigroup) a 15+% unemployment rate when counting those who stopped looking for jobs, the largest mortgage company in the country (Countrywide) forced to sell to Bank of America, the federal bailout of Fannie Mae, Freddie Mac and other housing related agencies, the massive housing foreclosures, bankruptcies and evictions in which most of whose homeowners have still not recovered, the enactment of HAMP, TARP and HARP federal legislation, the fact that firms like Blackstone, Carlyle, Colony Capital own, in the aggregate, more than 60,000 single family residences for rental. They don’t call it “The Great Recession” for nothing.
      I’d be interested in your definition of what you think constitutes a “500 year flood” in the real estate lending market. Thanks.

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