Career in investing

[Madpawn]

Hi everyone,

 

I’m currently working in consulting tech and have been working on slowly moving towards finance (e.g., I’m now doing tech due diligence, have my own investments through real estate and stocks). What can I do to better position myself for a career in finance at a entity such as Fairfax? I would love to work on the operations side of things and eventually move towards investments management and would appreciate any advise this forum has

[73 Reds]

1 hour ago, Madpawn said:

Hi everyone,

 

I’m currently working in consulting tech and have been working on slowly moving towards finance (e.g., I’m now doing tech due diligence, have my own investments through real estate and stocks). What can I do to better position myself for a career in finance at a entity such as Fairfax? I would love to work on the operations side of things and eventually move towards investments management and would appreciate any advise this forum has

Can't speak to the procedures you should take but it would seem that a verifiable track record is a must.

[Madpawn]

37 minutes ago, 73 Reds said:

Can't speak to the procedures you should take but it would seem that a verifiable track record is a must.

Is this enough tho? One concern I have is the lack of a CFA/MBA and lack of IB or financial m&a experience 

[73 Reds]

5 minutes ago, Madpawn said:

Is this enough tho? One concern I have is the lack of a CFA/MBA and lack of IB or financial m&a experience 

Again, I'm not qualified to answer that question but there are some professional money managers here on this board.  Totally understand wanting to work for a company like Fairfax but if you are truly exceptional at investing, you probably don't need to work for anyone.

[SharperDingaan]

You aren't going to work at a FFH until you already have a great deal of experience at the major Lifeco's, P&C's, and Banks;  Union Card - part I. You will also need an MBA, and at least a recent completion of CFA-level II; Union Card - part II. Thereafter, true to yourself, differentiation from the rest of the pack, and a record of successfully walking the talk.

 

When everybody looks the same, and they are all very good, you can only do as well as everyone else. To stand out you need to be in the right hand tail; either because you're that very rare savant, or because you're that rare one-off outlier. The one who holds up his hand and demonstrates to the prospective boss that his company is one of only five that you want to work for, you're here to learn from the best, and his job is safe for now 'cause it will take you 3 years to learn this portion of the business. Hire you now, or have you beat on the door everyday until you eventually do; time is a wasting! 

 

Your interview will be memorable! you will meet them again at various events, and if you actually do as you say; at some point there will be a callback, if only to see such an arrogant bastard fall flat on his/her face. But Lenny .... if you can actually walk the talk, and amongst the best, the things you can build!

 

Back in the day, there used to be MITI; today, it is the rebuilding of Canada's infrastructure. 

https://en.wikipedia.org/wiki/Ministry_of_International_Trade_and_Industry

 

Good luck 

 

SD

 

  

 

Edited November 26, 2025 by SharperDingaan

[Pellom]

Pick one of their subsidiaries and become an expert. Focus on operations and not investing. 

[Gamecock-YT]

Find a niche and get good at it. Become an expert on a stock, know it better than anyone else in the world that isn’t an insider. Then keep doing it. 
 

work backwards from why anyone would want to hire you. 
 

Also, I would say moving from operations into investment management is a pipe dream. You’ll get pigeonholed into your role. Your boss won’t care about your aspirations, will likely consider you a flight risk once you poke your head up, which inevitably stalls your current role (good luck with your comp days after that, you're on the shit list!), and the investment management folks are looking for someone to plug and play with the prerequisites and resume to match. You either go in through the front door via MBA/CFA or you backdoor it from building a book on your own. 

Edited November 26, 2025 by Gamecock-YT

[schin]

On 11/26/2025 at 6:53 AM, Madpawn said:

Hi everyone,

 

I’m currently working in consulting tech and have been working on slowly moving towards finance (e.g., I’m now doing tech due diligence, have my own investments through real estate and stocks). What can I do to better position myself for a career in finance at a entity such as Fairfax? I would love to work on the operations side of things and eventually move towards investments management and would appreciate any advise this forum has

 

@Madpawn - With your technical background, it might be easier to work at Markel Ventures or one of many Constellation subs. Again, just be good at what you do and I come from technical background and there's a lot of finance involved in scaling tech, cost/benefit analysis (AoA -Analysis of Alternatives), etc... that will allow you to flex you financial muscle.

 

Operational excellence and technical proficiency are great, but salesmanship/BD is another area that'll get you over to the finance side. 

 

My ex-wife was in finance and I found all those restrictions on what we can buy and when..was frustrating and to a certain extent limiting. 

 

Unless I got a job at RenaissanceTech, DE Shaw, or some super interesting HF -- where I'm a general partner.... it'll be too hard to go up the tech to finance ladder as a worker bee.

 

Be great personally and at work -- and people will find you.

[Madpawn]

12 hours ago, schin said:

 

@Madpawn - With your technical background, it might be easier to work at Markel Ventures or one of many Constellation subs. Again, just be good at what you do and I come from technical background and there's a lot of finance involved in scaling tech, cost/benefit analysis (AoA -Analysis of Alternatives), etc... that will allow you to flex you financial muscle.

 

Operational excellence and technical proficiency are great, but salesmanship/BD is another area that'll get you over to the finance side. 

 

My ex-wife was in finance and I found all those restrictions on what we can buy and when..was frustrating and to a certain extent limiting. 

 

Unless I got a job at RenaissanceTech, DE Shaw, or some super interesting HF -- where I'm a general partner.... it'll be too hard to go up the tech to finance ladder as a worker bee.

 

Be great personally and at work -- and people will find you.

Thanks this is some helpful perspective, the one challenge I have with the tech world right now is I feel like the ceiling is too low hence why the desire to move into something more on the operations / investing side where it seems easier to scale