What is the ballsiest thing you’ve ever done?

We all know finance tends to attract risk averse personalities. 

What’s the “ballsiest” thing you’ve ever done?


It can be in career, dating or a relationship, or any aspect of life. 


A defining moment. 

47 Comments
 

Godspeed. Many on this forum talking about starting a business. Few seem to take the leap. 

 

Anonymous Monkey

Godspeed. Many on this forum talking about starting a business. Few seem to take the leap. 

I started my own business. It didn’t really work financially but I learned a lot.

"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee
 

Analyst 1 in IB - Cov

Dropping out of high school because it seemed useless. 

I dropped out of high school too but then went back to an accelerated learning program. I finished 3 months earlier than my peers.

"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee
 

PEarbitrage

High School is pretty useless, more useful than college, but overall still pretty useless.

I disagree about High School. A guy a year before me in High School bought a boat on a one night a week job. (it might have been his wife's money, or maybe what they got from the super bowl ad.) still buying a 400 foot decomissioned ferry is a very questionable call. A guy a year below me left ESPN for a podcasting career with Draft Kings.

The only difference between Asset Management and Investment Research is assets. I generally see somebody I know on TV on Bloomberg/CNBC etc. once or twice a week. This sounds cool, until I remind myself that I see somebody I know on ESPN five days a week.
 
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"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee
 

11Belitist

Converted a killer family office/hedge fund internship role into a full time offer. Got drunk, decided I didn’t want to do excel in my twenties and enlisted into the Army. 

We will see if I will recover in the long run, but no regrets

Hooah

"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee
 

I flipped a hobie cat. 

The only difference between Asset Management and Investment Research is assets. I generally see somebody I know on TV on Bloomberg/CNBC etc. once or twice a week. This sounds cool, until I remind myself that I see somebody I know on ESPN five days a week.
 

collegemonkey123

Passed a cop car at 120 mph. Not sure how I didn’t get lit up.

"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee
 

Isaiah_53_5 💎🙌💎🙌💎

collegemonkey123

Passed a cop car at 120 mph. Not sure how I didn’t get lit up.

I played tag with a 996 Turbo and a V12 Vanquish in a 1997 Miata with the top down,  We dropped a C7 because he didn't have the balls to hang.  I saw ~125 on the speedometer, but I know that top speed top up was listed as 119 new.  The speedos run high on that too, and a dozen years couldn't have been great on it either. I will not state where this was for liability reasons.  I think i cheated last time by saying it was not a US highway, but a "limited access environment"

The only difference between Asset Management and Investment Research is assets. I generally see somebody I know on TV on Bloomberg/CNBC etc. once or twice a week. This sounds cool, until I remind myself that I see somebody I know on ESPN five days a week.
 

One of the ballsiest things I’ve done was quitting a comfortable position to start my own business. No safety net, no fallback plan—just me, my savings, and a vision. It didn’t go exactly how I planned, but I learned more in that time than any job could’ve taught me. Would I do it again? Probably, but with fewer blind leaps and more calculated risks.

 

johnchan476

One of the ballsiest things I’ve done was quitting a comfortable position to start my own business. No safety net, no fallback plan—just me, my savings, and a vision. It didn’t go exactly how I planned, but I learned more in that time than any job could’ve taught me. Would I do it again? Probably, but with fewer blind leaps and more calculated risks.

same

"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee
 

m_1

When I was 16 I stole a bunch of drugs from a drug dealer.

wtf coke?

"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee
 

I've been bridge jumping and tower jumping into water. Up to about 60 feet. Pure adrenaline rush.

"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee
 

One day I was in Cinque Terre with two chicks. We were walking along the coast of the five towns. We went through a couple towns and it was nice, relaxing, beautiful views on the shore. But on the third town we were walking and saw a cave off in the distance. It was on top of a cliff. For some reason I decided to scale the cliff in Rainbow sandals and these girls were screaming and crying at me. I had complete confidence in my climbing abilities. I made it to the cave and it felt like a grand accomplishment.

Later that night I gave both these chicks bare back massages. Then I had too much grappa and passed out before the three of us got into any shenanigans. We then went to Venice and I left them to go to Greece. 

"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee
 

Career: Missed the boat for Jr year internships, just didn't really understand the concept (not as big in my country to be fair) and had an above average but not stellar profile at the time. When I realised how crucial it was for landing a gig in say, IB, AM etc I literally made a list of every boutique bank/fund in my area that didn't have a formal recruitment program and just went door to door presenting my resume. In general people were more willing to talk than you might've expected and got a few coffees out of it, and after about 12 places I got a break at a well respected local shop, which led to many other opportunities. I strongly doubt I'd be in the seat I'm in today (analyst at a top MM HF) without having gotten that opportunity 10 years ago. 

Personal: There was a drop dead 10/10 girl at my high school. Easily the hottest girl I've ever seen and totally out of my league. We knew each other on a name basis but that was about it - had no mutual friends, just some classes together and brief interactions. One day I had a random fit of "What if-ism" and just walked up to her in the parking lot after school and said that I thought she was beautiful and I'd love to take her out sometime. She was super friendly about it....but let me down gently. Oh well at least I shot my shot, or so I thought. A few years later, long after high school had finished, she texted me out of nowhere asking to hang out. We went to the beach, she told me she'd never stopped thinking about me since that day, and we ended up dating for 3 years. 

 


Young Kid: after my mom died of cancer when I was 5 years old, I asked my dad to stop smoking so that he would live a long time for me.  That was the last time he smoked.

College: started a student club that I thought was needed and led me to be more than just a student.  

Relationship: asking my friend to go out on a date, right after she told me she broke up with her high school boyfriend.  I cut right in line of guys who would want to date her.  Bold and decisive.  I learned this lesson my freshman year of high school after a girl I liked asked me to the freshman ball and I said I wanted to go stag with my friends.  She ended up going with this other guy and then dating him after.  By the time she became a Sophomore in high school, the upper classmen guys were going after her and her friends.  You learn to take your shot. 

First job: was the first person (that I know of) to get a direct to Big Four job on the Mainland directly from the University of Hawaii (normally would be the local office) all because I put on the fourth application San Francisco instead of Honolulu.  It was lighting hitting my head, which can change your life.

Careerwise: sold my ROTH and 401K and other money to the tune of millions, to keep my business afloat amid various lawsuits and achieved a good exit that I felt was a 20% outcome. You learn that sometimes you have to bet on yourself all in, but know that your wife could leave you and you could end up with nothing.  I sometimes think this kind of boldness is for the ignorant/naive (which you need be somewhat naive to take big risks; Jenson Huang of NVIDIA talks about this when asked would he started that company knowing what he knows today).


I have never been in an actual war situation that was life or death.  That to me is being really bold.  

I’m just sharing my little acts of boldness to hopefully remind you that you can change your life by acting on lightning striking your head at the right moment.  And betting on yourself now, and not leaving it to your future self to somehow recreate the conditions of your lucky situations.  You need to seize them now, because “lightning strikes maybe once, maybe twice” (Fleetwood Mac song “Gypsy”). 

Have compassion as well as ambition and you’ll go far in life. I am interested in digital immortality. Check out my blog at digitalimmortality.com
 

I took the Aussie Gymnast Skiing up at Hunter when he came back um I had to keep him on the bunnies it really ruined my day I wanted to be on lower K27 and Hunter West

The only difference between Asset Management and Investment Research is assets. I generally see somebody I know on TV on Bloomberg/CNBC etc. once or twice a week. This sounds cool, until I remind myself that I see somebody I know on ESPN five days a week.
 

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"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee
 

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"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee
 

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