What is the most risky thing you have ever done?

Some people are risk averse and stay away from certain investments, or situations unless they know more, while others jump in.

What story can you share where in hindsight you really should have taken more due diligence, and how did it work out?

What is the most risky thing you have ever done in your property investment journey?
Climbed a cliff at Cape Woolamai over pounding surf (like you know when you young and stupid and just decide to give it a go while walking along the beach - no gear nothing). Rock gave way under my hand..... lucky I my other hand was grabbing onto something solid..... :eek:

The Y-man
What is the most risky thing you have ever done in your property investment journey?
I impulse purchased my first house... sort of. I had been looking in the area and knew the prices. Driving down a street I saw a sign to a home open. Inspected, liked the place and bought it that day. I didn't bother with DD or anything like that because it was to be my PPoR. I impulse sold it about 7 years later after renting it out for nearly 5 years. Made a nice CGT free windfall. No issues, no regrets. I would not impulse buy an IP though.
Got married
Yup, I'm with Allsuccess. Worst thing I've done is diverge from property into mining and bio speccies.

First property I bought I did a sweet reno job with my old man and released over 200k equity in 12 months thanks to a rising market and a less than conservative valuation.

I took 100k of that, and turned it into 50k pretty quickly investing in "great stories", "great resources" and "great management" :D

Unfortunately for me, I tend only to learn lessons the hard way. I'm not very bright.
Most risky that I "regret":
-- purchasing a holiday unit in JV with a friend.

Most risky that I've had a hand in (albeit don't regret, yet!):
-- going all-in on a purchase, that left us with literally NO buffers, for several years. Not a nice position to be in, but if things work out, it will eventually be all good (no guarantees, though - and we know it).
Jumped off a sheer 3000ft cliff in Yosemite national park in my hang glider.

As far as property goes... buying in Spain after the crash. Problem was I was too early and it kept crashing.
Lost 10k in a property syndicate I signed up for (3 months before the GFC) that I saw in the accountants office whilst waiting for an appointment.

Not much pain as it was via the SMSF. Still sucked though.
I know someone who married the same person twice - divorced again too!

Is it.Derryn hinch.!?!?!?!?

If I married the same girl twice and divorced her twice I would certainly question my ability to judge people

Oh and I put 130k on mining speccies

I think today they are worth about 2k

I don't even look at them anymore
I know someone who married the same person twice
I did that.

Once by law and once by church.

(In Mexico you had to be married by law before being married by church. Married by law in the USA. The disastrous consequence was two wedding anniversaries every year).
What is the most risky thing you have ever done in your property investment journey?

When I took out my IP loans a few years back I was told by my finance broker to take out income protection insurance (who even gave me several real examples from client experience), as did my accountant and my financial planner - "...because you never know" etc., and "...it doesn't matter now, but something can happen" etc. ; to which I always replied that I never get sick as I was extremely fit, run and lift weights daily, don't smoke etc.

Long story short... :) within 2 years and from nowhere, I got very sick and couldn't work for a year (only income source). The only insurance I didn't choose was income protection insurance in my policy at the time which would have been quite useful. :(
Listened to a property investor and bought at the peak in mackay with out doing my own study, trusted them to look after construction progress as they sorted the builder out, left with a category 1 defect (driveway) which you cannot fix without dropping garage slab, been sitting there not rented for over a year and market went to ****! Can't sue builder coz he will close up and I've already wasted 10g on lawyer fees! Fml:mad: