I finally made it to the so-called "promised land," and I did so through an unconventional path. But now that I’m here, it isn’t exactly what I envisioned. I recognize I’m blessed to have this opportunity, and maybe that makes me sound spoiled, but this is where I’m at.
The higher you go, the worse it gets: I used to think that things would get easier with time and seniority, but it’s the opposite. The higher up you go, the more the stress compounds. Managing directors aren’t immune to sleepless nights, and they bear the weight of every deal on their shoulders. The belief that life smooths out as you climb the ladder is a complete myth.
No light at the end of the tunnel: I see friends who’ve built multi-billion-dollar companies—they work less, their work is more engaging, and they have the freedom to shape their schedules. In finance, your success is always tied to the next deal. There’s no lasting equity, no company to call your own. Sure, you accumulate wealth, but you don’t own anything meaningful in the long run.
No one seems happy: It’s unsettling to hear senior associates and VPs talk about how they crave something as simple as feeling the sun on their skin during the day, free from constant deadlines. If even those who've climbed higher still long for freedom, what am I really working toward?
The golden handcuffs are real: VPs and principals are financially stuck. Their net worth is so tied up in vested stock that walking away would ruin their financial plans. They’re locked in, unable to leave without massive personal risk.
There are better ways to make money: In today’s world, there are people making millions in far more unconventional ways—influencers, real estate professionals, you name it. The old idea that you need to grind in a fluorescent-lit office for 80 hours a week to be successful feels outdated. There are so many other paths that don’t require you to sacrifice your entire quality of life.
The people are one-dimensional: When I look around, the conversation is always the same—football, golf, running. It feels like everyone’s stuck in the same loop, with little diversity in interests or perspectives. It’s suffocating.
I don’t care about running endless analyses until 2 AM: Staying up until the early hours of the morning, running endless scenario analyses under a stressed-out MD who needs a memo out for a multi-billion-dollar deal—it’s exhausting. I don’t care about this enough to justify the constant pressure. Why is everything always so time-sensitive? It never ends, and I don’t want to live like this anymore.
I wanted to be an investor, but I feel like a process monkey: Investing—truly thinking like an investor—feels like it’s only about 30% of what I do. The rest is coordinating diligence and running processes, just like I did in banking. It’s more about figuring out how to show the investment committee or my VP what they want to see, not presenting what I actually believe.
Now the question is, where do I go from here if I pull through? Well, I’m either going to pursue the hedge fund (HF) route or take an 80% pay cut to go work for my dad in return for 50% of his company, with plans to embark on a buy-and-build acquisition strategy.
very unique take
TLDR: my dad is rich and I don’t want to grind so I work for him
If my dad was rich why would I be taking an 80% pay cut? I make more money than my dad. Though his industry is ripe for growth IMO.
Does he own an HVAC business?
I agree with you. If you want to have satisfaction you will have to take the risk of becoming an entrepreneur. The only reason why people go into IB/PE is because it is a career that gives you clear visibility into becoming a millionaire whereas being an entrepreneur doesn’t. High reward as an entrepreneur means higher risk. Taking the corporate exit sounds enticing until you realize that you have the golden handcuffs.
In private equity reality is that even the MDs are just outsourced investment labor for the institutions and ultra high net worth individuals who are LPs. An LP could be sitting on a beach in Miami and collecting distributions for capital gains from the fund while the PE’s MD and investment team are stressing their asses off about their portfolio.
I realize that I’m not an entrepreneur, I might be one, but as of now I’m sticking to this career because I see no other way of making good money. If I get an opportunity to start a successful business I would in a heart beat.
I think you just need to do the risk/reward calculation but also listen to what your heart is telling you. I’m already hating this job as a first year and I don’t know what to do.
I can assure you the LP is not sitting on a beach.
If the CIO / Managing Directors don't perform / increase AUM to fund the E&F, Pension, or SWF - they are axed.
Brother by LP he means UHNW, someone who has their money in a fund, not an allocator
Yes like the other reply stated, I’m referring to ultra high net worth individuals in that specific example.
LPs often do sit on beaches / yachts
Make VP first and report back
My brother in Christ, my VPs work more than me and look exhausted. Also, did you not just read what I wrote? I'd never leave if I made it to VP, by then, I'm in it for the long haul. If I wasn't clear, I think I'm saying, I don't think I want this life.
Your mindset will definitely change by the time you are offered a VP promotion, and the workload grind will shift. On this forum you won't find happy stories of being a VP+ at MF PE to the points you talked about.
Can you describe your unconventional path to IB/PE?
Operating companies is where the money will be in the future. Owning them is nowhere as lucrative as it once was.
100%. Operators with quality track records are scarce
Can you expand more on that? Why will owning not be lucrative?
Not OP but there’s just a shit ton of funds doing all sorts of strategies. Not a ton of actual differentiation in them. For example, if a PE fund comes up with a neat idea of buying car washes at low multiples and rolling them up into a big business with a big multiple, that is unique and interesting. But once they do that a few times, other funds realize they can outbid them and just do the same thing and you end up with a fund paying 15+x for a car wash…
Another point is how unique can you be if all your talent comes from the same schools, the same banks, and just churns out LBOs when that’s not a unique strategy anymore. Running a business is very difficult and you can’t institutionalize that as easily as you can cutting a large equity check.
Basically, actually running the business and improving it will be more valuable than your cut of buying and financing a business going forward.
100% agree. Many strong operators never have to relinquish equity too as they grow. Have seen some crazy generational wealth created at ~200-500 person companies where the founders are still operating and have large chunks of equity. Can be absolute cash cows with nepotistic succession plans.
The problem with really successful operators is when an opportunity shows up with a truly asymmetric risk profile, they are already in a position of having enough wealth to take down 100% of the equity. It’s the shit they aren’t ~95% confident in that ends up being syndicated and raped on fees from every different direction.
Why do you say that?
**Operating companies with employee and management ownership. Global GDP will continue to grow as well as TAM for all industries, higher margins with AI, USA competitive advantage with energy and geography means more market share for domestics etc ... however, private markets are now ruthlessly efficient, higher rates, too much capital chasing too few deals, far more uncertainty with geopolitcs, higher implied volatility all mean lower returns going forward etc etc
Can you unpack this a little more?
What sectors and company sizes are we talking about here? Assuming you’re referring to portcos and late stage startups but interested to hear a little more.
Let us know how it works out
You and I would be best friends in a parallel world. You spoke my words.
.
What industries did these friends go into? Have you considered going down this path?
Energy
Do you mind expanding on this? Energy sounds capital intensive. How did they get started in this field?
Only you know how much money you need to be happy. From what you’ve written it doesn’t seem like you’d be happy in PE no matter what your comp is. Go try to work for a HF and if that fails work with your dad.
I agree with a lot of your points, so why in the world would you decide HF is the next logical step?
Good point
Interesting analysis, as someone who wants to develop in the industry, it really makes me question whether its worth it or not. But in all honesty working in the sector even for a while gives you two valuable things - capital and network. I think it would be worth it sacrificing a couple of years of your life in order to gain a bit of a "headstart" when you start something on your own.
Mate go work in a start up that burns it's cash on parties, conference and event
How nice! You slip in right at the end your dad has his own business you can take over eventually lol. What a tough life for this young kid!
Lmao, it's kind of like making the statement, my dad gave me a car when I turned 16. Yes, it's a car. But that car was also a 2008 Honda civic with 90000 miles. I understand I was blessed to receive a car, but just like the car, the business is a fixer upper. I'm not inheriting Hewlett Packard my man. If I choose that route, I'm living lean until I build it up to where I think it can be.
No idea why this is getting MS. I know of some folks who had this dilemma with joining their parents buiness vs. corporate jobs. Everyone I know that left corporate America to help grow / run their family business never returned back to corporate. Majority of them succeeded but I also know a family where the siblings are fighting over a struggling company. Was successful at first but imploded in the past 5 years (they do a lot of business through China and they got hit hard by Trump's policies in the late 2010s, pandemic negatively impacted their supply chain + relationships overseas).
A lot of risk of leaving a job like yours but its up to you to make that choice.
Really awesome that you've gone through your process of discovery and landed on what you want in a path forward. Most don't even get to this step of awareness. That kind of path, partner at MF / MD at BB or whatever isn't for everyone happiness wise.
And to have achieved all you have in your journey so far. Congratulations on all your success. All the best for the future.
Uh go work for your dad if you think there is potential in the business? Presumably you would inherit the other 50%, and your compensation will grow if you’re successful. You could always go back to conventional roles, but I suspect you won’t want to after you’ve experienced operating for your own company
Suttle troll post ✔️
Subtle*
SpellCheckSecured*
Deleted.
You’d be surprised actually. Most of them really don’t make that much money and even the top ones fizzle out quickly and lose sponsorship offers. This is coming from someone who used to work with a lot of them…
What’s your estimated range then
What’s your estimated range then
What’s your estimated range then
Clown post
Sorry bro. I see a lot of first world problems in the orginal posts. A lot of them depends on what perspective you want to adopt.
I am at VP/Principal level and changed job twice (from MF to MF to MM) and walked awayfrom all carries but learnings / deal expericne are better each time.
P.S. I have minimum associate life style. I like food, gym, doing deals (enjoy it). Don't care spending money/compare with others.
Inspired to post my perspective because I was in your shoes a few years ago (sans the MF qualifier or the family company off-ramp) and maybe my experience could be of interest, but then again, probably not. Just had my 3rd espresso, and I'm procrastinating an engineering doc review, so here I go on another rant anyways.
I turned down a VP promotion at my MM PE fund and a pod-shop HF role to pursue what is perhaps the most unconventional corp. dev. role on this website at a start-up-esque company. I have no regrets.
I started interviewing for my current role 12 months before a VP promotion and around the same time as I was getting looks in the HF space. I went thru several rounds at a few shops, including some household name type places, and while I enjoyed running the analysis I defended in my case studies, I couldn't shake the feeling that it was going to be a "same shit different color" vs. my distaste for the PE path I was on.
There's a heavy caveat here regarding compensation that gives me significant hindsight bias in my response. I've gotten quite lucky in that my equity comp (which ultimately came out at 20% of what I tried to negotiate for when joining - perhaps I do have at least one regret) has come out in the low 7 figures in the past few years. The proverbial "carrot" of carry at my prior fund has not materialized despite all the spreadsheet masturbation the firm leadership iterated on and shared with me as part of VP promotion discussions. Part of my calculus in turning down the VP offer including risking that carry to near $0. I did the same with equity comp at my new seat at the time of the decision, but perhaps if we had shit the bed and equity didn't materialize, I would have a different perspective on the decision today.. but that's a discussion topic for a therapist.
One thing I want to stress about my current role is it is so fundamentally different than my banking or PE experience that it took me almost 18 months to adjust and I still catch myself missing the "rigor" of finance. This is why your post has got me ranting here. This factor was the single hardest adjustment for me, and I suspect it may be an overlooked topic for you in the event you go work with your dad, or for those who seek a similar off-ramp out of high finance. I thought the lighter workload would be a net benefit, and while it certainly is these days, it gave me an existential crisis for a time. Do not overestimate the quality of some team members in "normal" industry roles outside of finance. If you do leave finance, do not expect your new coworkers to all share the same intensity/drive/work-ethic you've become accustomed to across your teams in finance. I have trained my team to a finance standard, but outside of our division it's a crapshoot.
I also faced more guilt than I anticipated for giving up what so many people on this site consider the "golden path" or having "made it". As someone who came from an unconventional background (no internships; STEM degree w/ GPA starting with 2; first real job at a no-name bank earning pennies; etc.), I felt like I was throwing away other folks' dream situation. This was another element that weighed heavily on me as I started up in my new role that I failed to anticipate.
To respond to a few bullet points of yours directly:
Golden Handcuffs - these are so real and there's no escaping it. If you're anything like I was, you have saved a decent chunk of change from 4+ y in finance but it seems like not enough. If you haven't already, build a simple model and compound that at a conservative 400 basis points for 20 years. It's probably enough. Life is too short to work a job that makes you unhappy for incremental dollars beyond a certain point. Only you can quantify that threshold, but my suggestion is that it's probably a lower number than you think when you're surrounded by finance people in some VHCOL city.
Better Ways to Make Money - yes, absolutely, but the grass is always greener. One of my childhood friends is a small-time "influencer" working full-time via socials; a graduating classmate of mine made an 8-figure business being influencer-adjacent. Neither are "happy" necessarily - one in fact is so miserable with their $50m revenue boot-strapped business relies on fake Instagram personalities that they have gone on record saying they would never take this path again in a million lifetimes. Money is just means to an end. For me, that end was to be "comfortable" - I don't need 3 vacation houses or an black-on-black Porsche 930 (although I do want these things). I can speak from personal experience that $400k cash comp felt no better than $200k cash comp on a day-to-day basis, because the former came with pretty severe psychological baggage.
Investor vs. Process Monkey - this really hits home for me; I joined PE to be "an investor". I wanted fulfillment from what I envisioned that role to be, and while at times I did truly feel fulfilled in the PE seat, most of the time I felt like a pair of hands at a keyboard with no brain of their own. The allure of my corp. dev. role was that I would be a part of building something and get my hands truly dirty.. which has been a mixed bag (topic for a separate post perhaps) but certainly has left me more fulfilled than PE. I know for a fact it doesn't get better with seniority at that firm - perhaps this is an idiosyncratic thing, but I doubt its an isolated case.
My final thought:
Without having spent time at a HF role I can't definitively say, but my evaluation of the roles I was seeing a few years ago suggested to me that it wouldn't be much better than PE for my own personal goals and values. Don't take the decision lightly, but don't be afraid to marinate on it for a few months before taking action. I took a week of solo "vacation" at a cabin on a lake (with my trusty firm-provided laptop and cell phone online the whole time, of course) before pulling the trigger. I had to grind on an emergency working capital IC memo for a failing investment during that time which probably sealed the deal for me.
Only you can make the final call, but as someone who opted out of the PE path and the HF alternative, I can tell you I have no regrets.
Thus ends another Onebagger rant™. Time to go argue with our technical team about the actual cost of their proposed R&D side quests.
As someone going into MF PE with the thought of doing a HF afterwards, what really turned you away from HFs? My understanding was that a lot of the process work was cut out in the HF world so even though there's a lot of stress / volatility, a lot of the BS is removed.
First of all going to get back to one bagger on his post, which was great and echoed my sentiment. I assume a lot of the work and people on HFs are exactly the same.
[Edited to add: sorry to keep writing fucking novels here - its a good distraction]
...
A variety of factors.. most, if not all of them, are unique to my own situation and personality. Not least of which was a damn-near visceral fear of my working hours and intensity being tied to the market, and my professional performance being tied to book performance. As someone with chronic analysis paralysis and a sprinkling of performance anxiety, I honestly don't think feel like I'm cut out for that aspect of the job. Might take some heat for being a coward, but I'll own it.
Again, I have no direct HF experience so I could be way off base here, but my personal thought is there would be a similar amount of stress in aggregate, albeit from different sources. Less bullshit and process/admin tedium as you correctly point out. Pure analysis-driven decision making, merit-based performance and near-instantaneous feedback - some people are better suited to that environment than others. Your mileage may vary. There are far more knowledge people on this board than me on the pros/cons of working at a HF.
A friend of mine is PM at a small fund, so I had some insight into his working life. As a burnt-out 3rd year associate on the verge of moving to VP, which in my view is the seat which provides the slimmest opportunities to lateral within finance, I was apprehensive of entering that world. He thought I was making a huge mistake by not taking a HF role and grilled me for it for months. His view was I could always do a year or two in HF, and the worst case scenario was I sucked and could then leave finance for CorpDev or some other easy off-ramp.. He wasn't wrong. I would echo that advice to most people in my former shoes - you have to weigh that against qualitative, idiosyncratic factors like burnout.
I'm a pretty unconventional WSO poster, and unlike many of you I didn't always want a career in finance. I got super lucky with an analyst opportunity, and couldn't say no to the unparalleled experience and opportunity it offered. After my doing my time in IB and PE for 5+ years, I wanted a break from the grind and stress more than anything. I figured HF would be equally stressful and intense for me as the PE seat I was leaving.
Caveat again that I'm speaking with major hindsight bias, but most of the team at the exact fund/pod I was considering no longer work there. Granted that team probably earned a multiple of what I have in the same time, but I didn't want to expose myself to that sort of career risk. I wanted stability and longevity, at the expense of earning potential and overall trajectory. IMO, my decision to leave to the corp. dev. world basically sterilizes my finance career forever. I lost a lot of sleep over that initially, but now I am comfortable I made the right call for me.
For you, the constraining variables might be entirely different. IB -> MF PE -> HF is a pretty phenomenal trajectory for a variety of reasons we on this board understand better than most. Take my perspective above, along with most thoughts on this board, with a healthy dash of salt. I say perspective deliberately - I don't presume to be informed enough to offer advice.
$50 million? What do they even sell?
I won't pretend to understand the space well, and want to be careful of doxxing anyone, but as I understand it, its Merch and Merch-Adjacent - including white labelling, drop-shipping, and introducing creators to manufacturers.
They've been going a relatively long time; since before the term influencer was common (in my circles at least). The $50m number is a few years old now - looks like they brag about a significantly higher number nowadays.
This space is crazy - a young family member of mine bought a youtuber's branded hoody for $90. It was a Gildan. Probably cost $7, all-in landed in the US, to the YouTuber.
If you're interested in a related rabbit-hole, look up a YouTube creator called Will Lasry (@wlasry) - he goes to these manufacturers for major recognizable clothing brands and gets their quotes for 200/2,000 unit orders. Super interesting content and will make you think twice about buying branded clothing. I've seen him cover some stuff I've copped for >10x the price and I consider myself to be pretty cheap when it comes to clothing.
Would love to read a post on your “mixed bag” experience in a corporate and in particular the projects you’ve most liked/disliked
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