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How Fear Stopped Me from Capturing a Once in a Lifetime Real Estate Market Opportunity

The biggest deal of my life

Yesterday evening, I submitted an AOS for the largest deal of my lifetime.  By faaaaar.  Like orders of magnitude.

I didn’t feel scared.  My partner and I had thought through and carefully crafted all of the contingencies and clauses to protect us.  We conferred multiple times about various risk mitigation options.  I had been having good conversations with the seller’s broker.

This morning, my partner said to me “How does it feel to have submitted that offer?  Were you scared when we did it?”

My answer was an easy and resounding “no”.  In fact, what I feel is both a distance from the deal, the submission, the size, as well as an excitement about the gamesmanship that is about to commence.  Over the past 5 years, I have found out that one of the most motivating factors for me in any aspect of life is the game of “strategery” as I call it – of figuring out how to get what I want while also working within others’ boundaries.  I love the unplanned moments when I hit upon a path through an obstacle.  If a collaborator voices critical or skeptical feedback, all the better!  It makes the gamesmanship even more fun.

Boy, how far have I come.

I wasn’t always seizing opportunities

Back in 2008, we purchased, rehabbed, and rented our first property – from many states away.   We had some stumbles during the process and yet came out on the upside, while providing good housing to a Housing Choice Voucher recipient.  Providing affordable and good housing is important to me.  Without a safe place to be, how can anyone thrive?

Do you remember 2008?  At that time, my partner said we had a once in a lifetime opportunity to buy 100 single family homes for our rental portfolio, and build the foundation for the lifestyle I wanted.   He was the student of history, of economics, of finance.  I most certainly was not.  I blindly nodded my head and said “let’s do it”.   That was the time we could buy properties with no money down, still hit the right DSCRs, rehab for comparatively much lower cost, and yet rents were not that much lower than they are now.

So we did about 50 transactions.  And even being naive in the actual practice of rental real estate – i.e. tenant selection, process formalization, tax deductions – we still made money.  But not what we should or could have.  Not what we could have built for a lifetime, if we had good strong teamwork.  If I had showed up.

What Happened

So why didn’t I show up?
My fear.  My fear of big numbers.  My fear of overwork.  My fear of success.  My fear of financial loss.  My fear of having to give up control in order to get to a bigger pie.  My fear of turning away from the “get a good job” mantra that my immigrant family had instilled in me.  My fear of making another huge life-changing mistake (I had made a few doozies already).  My fear of trusting any other person after perceiving myself as having navigated many life challenges “all by myself”.  (read that as “ego”)

It took me a good 13 years to move through that, and only this year can I say I’m not even having those thoughts.  But, guess what?  The market doesn’t wait around for your fears to pass.  You either face them directly and leverage resources and wisdom to move through them…or you lose out.  But I’m not just talking about the opportunities lost for growing wealth.  I’m talking about the fundamental damage to trust and confidence that happens when you say “yes” to something and then actively or passively work to not meet the commitment.   THAT can take years to repair, if at all.  And sometimes it causes one to look for other sources of partnership that end up going bad (yea, we did that too).

The one good thing is during that whole period, we successfully navigated the finances of all of our deals and returned all capital with the expected rate of return, and we still have more to return.

My mindset now

It’s 2024.   We find ourselves in another significant market opportunity – albeit not as straightforward.  And I’m not letting fear get in my way.  No matter what happens with this big deal, I’m going to move through with all the resources and support we have.

Let’s see what happens this coming week!  I’m sure a few years from now we’ll look back at this offer, no matter what happens, and laugh at aspects of how we approached it, but for now – it’s the product of fearless prep!

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