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Posted (edited)

I'll tell you this much, not sure I have enough life to fit it in nor the wife to support it but i would LOVE to race vintage formula fords for fun.  

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Edited by troph
  • Hook 'Em 1
Posted (edited)
5 hours ago, troph said:

another big mistake. went all in on a race car drive line and transmission/transaxle company for the hobby enthusiast crowd just before the financial crisis. transmissions, transaxles, gears, axles, differentials, CV joints, suspension related parts, etc. lots of super freaking cool shit actually. race cars like this (formula atlantic and below that sprites and then all sorts of cars inbetween, some late model formula ford, all SCCA classes, etc...

image.thumb.png.3c58df10d11e82e31611a4b385aeace5.png

 

image.thumb.png.f7014441878e4781aa07950e6fb77fbe.png

Relates to my choice not to transfer to Dubai with a AMLAW top 15 firm at the time. jesus fucking christ we went all in, then went all in again on a manufacturing company, moved it from SF to Austin, ballsy move and lost EVERYTHING when the financial crisis hit. only reason we didn't declare bankruptcy was because the lawyers were too busy to take us I couldn't get any traction. ended up with a few equity deals right after that that allowed us to dig out of our mess but holy mother of god 2008 - 2014 was unbelievably difficult. 

but success and failure is not a straight line, it's not linear, and our bounce back was quick from 2015 once I had the guaranty settlement amount paid off and started cashing in on what I had learned.

Never go all in, not in vegas, not with a bank, not with your fortunes, maybe with a girl (phrasing I get it) but even then, consequences and risks abound.

 

I remember we talked about this around 2012 when I was piloting my SaaS startup  into the side of Bootstrap Mountain.
When you described it I said something about how much more fun your company was than mine, and you basically responded that it was destroying your life. 

Edited by Bozo_Casanova
  • Fuck Around and Find Out 1
Posted
17 minutes ago, Bozo_Casanova said:

I remember we talked about this around 2012 when I was piloting my SaaS startup  into the side of Bootstrap Mountain.
When you described it I said something about how much more fun your company was than mine, and you basically responded that it was destroying your life. 

It pretty much did ruin everything then, but things rapidly started going the right direction in 2013-2015 and has been pretty good since then. Won some, lost some but never went all in again. Real estate has sucked the last 3-4 years for us but this tough spot has been nothing like 2008-2012.

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  • Rage+1 1
Posted

Oh here’s another one, I was an angel investor in 2013 or 2014 in a start up that later sold for $500m. I did great like 35x returns, but two things sucked - had to split half with my ex and we didn’t put enough in to be the end game. I guess I shoulda gone all in on that one.

Posted (edited)

Okay, so add another one to the list.

I had an offer at Oracle during Covid when everyone was overpaying everyone, to join there growing OCI stack in services.

Pretty good take home pay but a big equity component with gauranteed refreshes yearly for three years, at like at $60/share. I thought, "Oracle? What a grindhouse. They suck, they are barely humans and neanderthals that are left at Oracle in 2020 after completely getting taken to the woodshed and beaten in the cloud wars."

So I took another job with a better brand name.

Probably left $2.5-3 million bucks on the table after yesterday.

Edited by Vegas64
  • Fuck Around and Find Out 1
Posted (edited)
19 hours ago, Vegas64 said:

Okay, so add another one to the list.

I had an offer at Oracle during Covid when everyone was overpaying everyone, to join there growing OCI stack in services.

Pretty good take home pay but a big equity component with gauranteed refreshes yearly for three years, at like at $60/share. I thought, "Oracle? What a grindhouse. They suck, they are barely humans and neanderthals that are left at Oracle in 2020 after completely getting taken to the woodshed and beaten in the cloud wars."

So I took another job with a better brand name.

Probably left $2.5-3 million bucks on the table after yesterday.

I'll raise you one, a certain now high flying tech darling of Austin - large company, been around forever and struggled perpetually as the ugly fat bridesmaid to a national tech darling that is now in the shitter - was a frequent landing spot for attorneys from the firm I left. at one point stock was below $10 and it's recent highs (last couple of years) were plus or minus $200 per share. At its low point the company was giving out stock options and RSUs like it was halloween at 10pm and they wanted to get rid of the candy before lights went out. GC is retired and worth over $200M and there are rank and file attorneys there that have made intense money staying put. VPs and Sr VPs which is probably my level at this point are probably worth a cool $20-30M if they played their cards right. I can't tell you how many times I turned down the chance to go in house.

don't get me wrong, I'm doing really well for myself and frankly the Dubai thing and this in house thing would have NEVER worked out, just not my style but the money left on the table is staggering.

Edited by troph
  • Rage+1 1
Posted (edited)

fucking A I have another one ... we bought 3 acres of undeveloped land on lake travis - land itself is not on the lake but has views and there is an easement for water access to have a boat dock etc. we paid $1M in 2019. We were offered $3M in 2021 and turned it down thinking we would break ground soon and instead of $2M in profit over another 3 years there would be $5M in profit. RE market tanked as rates and costs went up, we still have the raw land, and see no way to develop or sell anytime soon.  it's probably worth $1.8-$2.3M but only on paper (plus we have a capital stack and some debt that makes that close to breakeven on the low side). we are currently self funding costs to carry.  shoulda taken that triple in 2 years. wtf were we thinking.

pigs get fat, hogs get slaughter my friends. 

I will never let that mistake happen again.

Edited by troph
Posted

Buying IBRX?

Fairly early on I did have a good amount of BTC but then I found out about leveraged trading on BitMex and blew it all. 

Work wise I could have joined a small startup many years ago called Klaviyo but would have had to move to Boston. 

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Posted (edited)
On 9/10/2025 at 3:26 PM, Vegas64 said:

Okay, so add another one to the list.

I had an offer at Oracle during Covid when everyone was overpaying everyone, to join there growing OCI stack in services.

Pretty good take home pay but a big equity component with gauranteed refreshes yearly for three years, at like at $60/share. I thought, "Oracle? What a grindhouse. They suck, they are barely humans and neanderthals that are left at Oracle in 2020 after completely getting taken to the woodshed and beaten in the cloud wars."

So I took another job with a better brand name.

Probably left $2.5-3 million bucks on the table after yesterday.

2014 I was in a specialist SE role at a big tech focused on VDI. A friend of mine from my team got downsized, and ended up at Nvidia. At the time they had just released some high end workstation GPUs that could be virtualized, and we were selling a lot of them in my practice. Anyway, my buddy reaches out to see if I'd be interested in jumping over there, so I went through the interview process. They eventually made me an offer, and low-balled me. I saw it as basically a lateral move to a niche company with less security than I had at the time(My twins were 7 then), so I said "thanks, but no thanks"...

Buddy is still there, and just bought a house in Crested Butte..

Edited by Pescado_Rojo
  • Rage+1 1
Posted
2 hours ago, Pescado_Rojo said:

2014 I was in a specialist SE role at a big tech focused on VDI. A friend of mine from my team got downsized, and ended up at Nvidia. At the time they had just released some high end workstation GPUs that could be virtualized, and we were selling a lot of them in my practice. Anyway, my buddy reaches out to see if I'd be interested in jumping over there, so I went through the interview process. They eventually made me an offer, and low-balled me. I saw it as basically a lateral move to a niche company with less security than I had at the time(My twins were 7 then), so I said "thanks, but no thanks"...

Buddy is still there, and just bought a house in Crested Butte..

No alternative text description for this image

 

That's a good one.

  • 1 month later...
Posted
On 9/9/2025 at 9:35 PM, troph said:

another big mistake. went all in on a race car drive line and transmission/transaxle company for the hobby enthusiast crowd just before the financial crisis. transmissions, transaxles, gears, axles, differentials, CV joints, suspension related parts, etc. lots of super freaking cool shit actually. race cars like this (formula atlantic and below that sprites and then all sorts of cars inbetween, some late model formula ford, all SCCA classes, etc...

image.thumb.png.3c58df10d11e82e31611a4b385aeace5.png

 

image.thumb.png.f7014441878e4781aa07950e6fb77fbe.png

Relates to my choice not to transfer to Dubai with a AMLAW top 15 firm at the time. jesus fucking christ we went all in, then went all in again on a manufacturing company, moved it from SF to Austin, ballsy move and lost EVERYTHING when the financial crisis hit. only reason we didn't declare bankruptcy was because the lawyers were too busy to take us I couldn't get any traction. ended up with a few equity deals right after that that allowed us to dig out of our mess but holy mother of god 2008 - 2014 was unbelievably difficult. 

but success and failure is not a straight line, it's not linear, and our bounce back was quick from 2015 once I had the guaranty settlement amount paid off and started cashing in on what I had learned.

Never go all in, not in vegas, not with a bank, not with your fortunes, maybe with a girl (phrasing I get it) but even then, consequences and risks abound.

 

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Posted (edited)

All of mine are in real estate. Coming out of the financial crisis, I bought real estate with buddies. By the 2019 or so timeframe we were at close to 300 doors, had a property management company managing 800-1000 doors, lawn company, etc. Property values were not increasing in our market and it was all a big ass headache with our day jobs, so we liquidated leading into and through Covid. The values I’m seeing on the same properties selling now is significant. One 8 plex we sold for $300k (needed some work) is currently listed for $1.2M.
 

I also had a chance to buy 30+ finished condos in a development on 30A out of receivership for $250k each back then. We put the money together and had an accepted offer at less than that with the bank and got cold feet during due diligence because it had what we thought was a strange beach access setup and a couple other issues. The association had a pontoon that ran you back and forth across a dune lake to a beach access and we thought for rentals it just wouldn’t interest them. Last time I looked they were selling in the $1.3M range and the building stays heavily rented.

The state helped fund developing a 1000 acre lake about 30 miles from me. During the time frame where they were doing surveys, I had a chance to buy what ultimately would have been 20+ waterfront lots and additional land for less than $200k. We walked the property after they had surveyed it and just couldn’t get a good feeling about the static water level line and there were a lot of questions about homeowner access still. Needless to say that was a bad call.

Edited by Brew

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