Old Ape Checking Back In – 15 Years Later

Hey all – old ape here (don't know that's still a thing now on WSO). Just realized that I still had this account , so here goes my first post in about 15 years.

Quick background:

  • Tier I target school, got lucky with a full scholarship.
  • Started in consulting, got my CFA in 18 months then lateral’d into 2nd year IBD, tier I.
  • Moved on to a multi-strat hedge fund, basically we lend money to whoever needs it on the best terms possible (aka structured finance).
  • Sat on the board of a Nasdaq spac when it was the rage a few years back 

But the truth is I always wanted to build some shit. 

So I took a year off building random stuff, then ended up in Silicon Valley for the last decade. First stop was a new boutique merchant bank spun up by some big names (ex-global chair of M&A at Tier 1, former GS head of corpfin, etc.). Then Trump admin locked down a lot of deals (we focused on Asian buyers / US tech at the time), CFIUS was brutal, deals fell through. 

Then I completely switched gears, found an operating role a venture-backed startup to see what it's all about. Landed at a no-name but turned out the founder sold his first startup for 9 figures in his late twenties - with no outside capital (wtf). Made me realize all these hidden wealth behind the scenes being built in the valley. 

When GPT came out two years ago, something told me this was going to be the biggest thing in my life time, so I called up my buddy who was a researcher at Google Brain (smartest guy I can find) and been heads-down building in AI since.

Long story short, I've seen my fair share of shit, was lucky to have worked with some of the smartest people around, now looking back (and look forward) sharing a message that I tell all of our college interns:

  • Take AI seriously. Most bankers statistically won’t make it all the way to MD. PE is going to run leaner than ever with AI. IBMBA → Big Tech pipeline is shutting down. All while AI is going from a helper role to flat out competitive to most what you can do. Traditional careers are already a thing of the past, the future for most of you is going to be rocky.  
  • Had coffee w my hedge fund boss (guy was taking home $50M a year), told me he could now run a multimillion deal with just himself, AI, and maybe one analyst. That’s how real this shift is.
  • IB is still one of the best exposures you can get early in your career. But no matter what you do after, learn AI. Better yet - use the new “vibe coding” tools to actually build something.

The last generation had home equity as their wealth base. The future? My bet is product equity. Build 2–5 small products, do it when you are in college, lowest opportunity cost, and got time to burn, keep them running, sprinkle some love and nurture them (not the Silicon Valley go viral or go broke shit), and be a daddy to your product. Own the product, own the community of users. Maybe it goes no where, but my experience tells me time is the greatest equalizer, problem is most people don't have the patience to stay with what they built to make it to light at the end of the tunnel. 

If you can do this consistently (and assuming your product doesn't royally suck), my bet is it will compound gradually over time, you end up with some paying customers, a decent community of users, and a good story to tell. Not only is this the best way to get real world experience, but you will feel human doing it (not pushing papers and excel models). So if you do it well, it's good for the wallet and good for the soul. 

Anyway, figure I write something quick. I will consider a follow up post or answer of questions if I get enough bananas. 
 

26 Comments
 
  • Had coffee w my hedge fund boss (guy was taking home $50M a year), told me he could now run a multimillion deal with just himself, AI, and maybe one analyst. That’s how real this shift is.

Having never worked in HF world, can you elaborate on this:

  1. how many people / how much time was previously spent doing a 'multimillion deal'
  2. How specifically is AI eliminating resources required
  3. How does he get around information paywalls (bloomberg, capiq, etc.) to get good information
 

Quaneaser:

  • Had coffee w my hedge fund boss (guy was taking home $50M a year), told me he could now run a multimillion deal with just himself, AI, and maybe one analyst. That’s how real this shift is.


Having never worked in HF world, can you elaborate on this:



  1. how many people / how much time was previously spent doing a 'multimillion deal'
  2. How specifically is AI eliminating resources required
  3. How does he get around information paywalls (bloomberg, capiq, etc.) to get good information


2. It’s not.
3. OP mentioned that the Partner still has an analyst on his deals.

 

I want to play devil’s advocate on your product equity idea. How do you account for the risk that your product could be made obsolete by rapid innovation from incumbents (e.g., ChatGPT Agents, Salesforce Agentforce, etc.). I’ve seen startups lose ground quickly as big tech launches competing features within months. How do you avoid that?

 

Learn AI…high level, learn to check its work and quality prompts. Can be a massive time saver, instructor, etc. Just remember, if you don’t understand what you’re asking it, you won’t be able to tell if results are legit.

Only two sources I trust, Glenn Beck and singing woodland creatures.
 

Shock - finance professionals get insecure at a former peer turned entrepreneur. Haven't seen that one before. Sore truth is, team, that society rewards risk-taking builders, not those who make a load of money for the builders/shareholders. Can't stress the point on product equity more. You're working for yourself (rewarding), getting feedback on your product from real users/creating a community (again, rewarding) - this is the responsibility of MDs, and probably most importantly, trying to create value out of something from nothing (most rewarding). This isn't to say everyone should immediately throw their hands up and quit tomorrow, far from it. But there's nothing stopping anyone from hacking away for a couple of hours each weekend on a problem/something that you think others might find useful. And in the age of AI - it really is more possible than ever to go learn a skill and execute on that idea. Code, design, iterative thinking - all collapsed through LLMs. There's no downside to this - best case, you get a form of "passive" revenue stream, worst case, you accumulate real knowledge from learning by doing and create IP (potentially reusable) which is uniquely yours. 

 

Agree with the principal of independence and entrepreneurship but this massive AI jerk off is just old and I think ignores the fact that many great businesses continue to be built that have nothing to do with AI

 

Almost all tech companies (with the exception of Amazon, but the downside is that you have to work for Amazon) have a bias against MBAs because they’re seen as worthless middle managers/product managers with no technical skill. This is even more exacerbated by the fact that people in MBA programs favor strategy roles given that many of them come from a consulting adjacent background, and strategy is often looked at as one of the least important functions in tech companies bc they’re product-led. So basically, you’re fighting an uphill battle when recruiting for tech, and they hardly go on campus (unless you’re at Stanford maybe Berkeley) so you have no chance to network face to face with those companies like you do with consulting and finance. 

Edit: I only just saw now you asked for what could be an alternative. Not sure if by alternative you meant alternative ways to break into tech or alternative industries to recruit for. For the latter question, a lot of us ended up having to take finance roles (not necessarily just IB - think corp fin, strategic finance, investment management, etc) or go into strategy/tech consulting roles at Tier 2 firms.

For the former, I've seen people who went into a technical Masters program like engineering, data science have more success pivoting into tech from a non-related industry prior. But again, still not great overall, just better chances than recruiting for tech out of MBA.

 

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