What was your Most Courageous Moment as an Investor?

54 Replies

I recently wrote a blog post about the start of our real estate investing. 

Recalling how scared I was when we began made me wonder about stories of courage. 

I think we were most courageous when we started. 

Knowing the math was only sort of right and that we were only sort of prepared. 

What was your most courageous moment as a real estate investor?

Thank you in advance,

Jonathan

I am in agreement with you Jonathan that as a beginner its when we exhibit most courage. If you start out wholesaling there's courage to do so and successfully close or if you choose to venture into another aspect of real estate investing there's courage needed to make that a success as well. So here are a few courageous moments for me in the beginning.

-Taking my first action after all of the schooling

-going in that abandoned house by myself (with unstable floorboards and missing steps on the staircase)

-making the phone calls 

-signing those agreements of which I wasn't familiar with or sure it was in my best interest

-trusting my gut

-although the fear had not subsided after my first closing I chose to re-up on more actions

Kudos,

Mary

2 Instances:

1)I started in 2000 by buying an REO though an agent. I was my most courageous when I realized that I could make a lot more money dealing directly with sellers as opposed to going through Realtors. And I was not an aggressive, direct sort of person so stepping out of my shell and courage to cold call and door knock took the most courage at that time.

2) But it's also up there with me weathering the storm (bursting of the RE bubble), surviving (never quitting REI) and coming back on top wiser and stronger with my career and business.

@Joe Villeneuve  

That is bravery. :-)

I suspect that moment also helped you refine your approach carefully. 

My wife often serves as my most thoughtful concept critic. 

Thank you,

Jonathan

@Mary B.  

Thank you for sharing your view. 

Putting it all into action really does take courage. 

But I find that the action through courage also builds strength and character. 

The next scary moment seems more doable having had the courage once before. 

Thank you again,

Jonathan

Handing $10K cash to a seller before closing.  Luckily, everything went as planned but knowing what I know now I would not have done that.   I still own that home and it is my largest cashflowing property, $900/month.  There are some advantages of being naïve.

Every time I purchase at Trustee sales my hands still shake while giving them cashier's checks.   That is a lot of my hard earned money and I'm hoping my educated risk pays off.

@Ibrahim Hughes  

Your second act of courage gave me chills. 

The crisis was no fun to face. 

We moved house during the crisis, into an unfinished flip, to make that time successful. 

May we all not need such courage again for a long time, if ever. 

Congrats to you on persevering. 

Thank you,

Jonathan

Originally posted by @Jonathan Cope :

@Joe Villeneuve 

That is bravery. :-)

I suspect that moment also helped you refine your approach carefully. 

My wife often serves as my most thoughtful concept critic. 

Thank you,

Jonathan

 Like your wife, mine is often my "test presentation".  Lucky for me, she's also my greatest supporter with these programs.

@Rocky V.  

only time I got nervous at trustee sales when a property came up and all the players were there and I was the only one to bid...  Was I smarter then them or did they know something I did not know.... Well I had it go both ways.

1. property had a 95k senior tax deferral that we missed.. I had to totally gut ad bedrooms etc to break even on that one.  and of course the other bidders new this and probably thought there goes Jay he is fubared on that one.

2. another one I was the only one and one romainan dude that did not understand a personal check was not going to do.. I got it for minimum bid.. But it had an underlying zone that allowed 24 units to the acre.. made 150k on the flip in 45 days.. that was a good one.. but non the less very nerve racking when the regulars were not there to bid.

My most courageous moment was starting my blog and therefore broadcasting what I did to the whole world. As I post my articles on my Facebook and address what I do pretty publicly. 

While getting started was "scary" for me the scariness was letting people know what we were doing, i.e. public opinion was scariest. While our close friends, squadron mates and some locals new what we did from watching the number of listing I had on local websites and Facebook pages. For the most part we operated under the cloak of "silence". Most family didn't know what we did and for me that was comfortable. So opening my self up in the real life was/has been the hardest!

It has so far been the most rewarding. Since I have opened up I have made more connections and really started to network. While I have already had a tenant "throw it in my face" there has been more good than bad. Althoguh the experiment is only 2 months old. So check back with me in a couple of years!

Originally posted by @Jonathan Cope :

I recently wrote a blog post about the start of our real estate investing. 

Recalling how scared I was when we began made me wonder about stories of courage. 

I think we were most courageous when we started. 

Knowing the math was only sort of right and that we were only sort of prepared. 

What was your most courageous moment as a real estate investor?

Thank you in advance,

Jonathan

My most courageous moment was back in 2007 when I was contacted by a seller desperate to offload her house in Virginia. I had no money and no-so-great credit. The only solution I had to offer her was me lease-optioning her home for the sole purpose of finding the end-buyer. 

When I spoke to her, there was a lump in my throat and I crossed up some of my words. Waiting for her reply (after my extra long explanation of the process) seemed to have taken an eternity. When she agreed to the terms, I wasn't excited... I panicked because I had no experience on how to go about sealing the deal. The only closing statement I had was a meet up date that I presented in the form of a question. How weak.

I spent nearly half the night before meet-up day combing over the contracts I had pre-prepared. When I finally met her, I felt like she was sizing me up like, "this is the guy I was speaking with?" 

In the end, she was a very willing and graceful owner and we did great business together until the last tenants decided to raise pitch forks on us because they could not qualify for a loan and wanted their earnest money back.

I grew some chest hair during that experience.  

@Rocky V.  

Putting one's money where their mouth is always the scariest test. 

There are times I am still surprised that I assume these risks. 

But I take strength from the preparation, education and past success. 

Nonetheless, I found myself unsettled just yesterday when I was considering a new neighborhood. 

Good luck. 

Thank you for sharing,

Jonathan

@Joe Villeneuve  

I am with you. 

Some of my greatest fortune is how seriously and supportively my wife takes the real estate investing business. 

Yet another thing to be thankful for this season. 

@Jay Hinrichs  

That is great perspective. Thank you. 

1) must have been an annoying lesson to learn. 

2) sounds like the good version of karma paying back. 

Your stories remind me of Gretzky's great quote, 'you miss 100 percent of the shots you don't take.'

You have to be more courageous than him of course. 

The shots he took rarely hit back at him. 

Thank you for sharing,

Jonathan

@Elizabeth Colegrove 

Going public is quite courageous. 

Being public about the potential to fail is always scary. 

Like @Joe Villeneuve  , I find that sharing my endeavors publicly with family and friends makes me more thoughtful and deliberate in my approach. 

It somehow professionalizes my process. 

During the crisis, I had people try to use our openness about investing against us. 

Somehow they momentarily took strength from suggesting that we were worse off than them. 

Thankfully our conservative approach gave us options throughout the crisis that made us stronger. 

Best of luck with your blogging and investing. 

Thank you,

Jonathan

@Guy M.  

Thank you for sharing. 

That is a great story of courage. 

You must have felt like you were on a tightrope the whole time. 

Congratulations on facing the newness and the circumstance. 

Most projects after that must have seemed simple. 

No better way to get life experience. 

Thank you again,

Jonathan

Quitting my job of 19 years to pursue apartment investing full time.  I had to sell my house at the beach and downsized to minimize the living expenses.

@Steve Olafson  

Impressive. 

Hopefully you felt then that you were moving toward what you were supposed to do. 

Toward a passion or life's purpose. 

I am always pleased by how confident I can be in the face of a next big step when I know I am moving along the right path. 

Thank you for sharing,

Jonathan 

Originally posted by @Jonathan Cope :

@Steve Olafson 

Hopefully you felt then that you were moving toward what you were supposed to do. 

Toward a passion or life's purpose. 

 Yes, it worked out well.  I have bought and sold over a thousand apartment units in the 15 years since that time.  :)

I once bought 8 units of "apartments".  Well, I made a lot of mistakes on the front end, over-paid, didn't get the type of financing that I thought I would get, the market crashed, etc, etc.  Anyway, I was in a negative cash-flow situation (yes, believe it or not, it can happen).  I guess the courageous thing was in the way that I got out of them.  I took them to absolute auction.  Lost money (I expected to before the auction, and I did), but I got rid of them and can now move on with life.

@Bryan L.  

Now that took courage both to do and share. 

Thank you. 

Knowing when to fold'em takes a lot wisdom and strength. 

I've been there in the equity markets. 

My view was that the loss was the price of education. 

Not an education I would ever hope to repeat. 

Thank you again,

Jonathan

I've had a knife pulled on my and accused of being an f-ing Jew by a sub...

Welcome to the world, son. Those of you nubs who think that REI is all about the damn CF numbers you see on your screen - think again.

Why are you doing it, and why will you not quit when **** hits the fan...?!

@Ben Leybovich  

Oh no, that's not good. 

Am sorry to hear that you experienced either. 

I'm always disappointed when the nasty side of life shows itself. 

Desperate people do inane and dangerous things the world over. 

Bad people, too. 

The threat of loss of life and dignity seems too much to consider when planning by spreadsheet for a next investment but is critical, as you note. 

Real estate is in the real world. 

Planning thoughtfully and mitigating risk as feasible should be front of mind for all. 

Thank you for sharing,

Jonathan

Free eBook from BiggerPockets!

Ultimate Beginner's Guide Book Cover

Join BiggerPockets and get The Ultimate Beginner's Guide to Real Estate Investing for FREE - read by more than 100,000 people - AND get exclusive real estate investing tips, tricks and techniques delivered straight to your inbox twice weekly!

  • Actionable advice for getting started,
  • Discover the 10 Most Lucrative Real Estate Niches,
  • Learn how to get started with or without money,
  • Explore Real-Life Strategies for Building Wealth,
  • And a LOT more.

Lock We hate spam just as much as you

Join the Largest Real Estate Investing Community

Basic membership is free, forever.

By signing up, you indicate that you agree to the BiggerPockets Terms & Conditions.