10 Years. 10 Hard-Earned Lessons in PE.

I trust that many of you can relate to this, or even better, many of you have lived these exact lessons. No particular order of importance but I feel these are ones that I need to learn, re-learn or reinterpret in my own head.

• On pursuing PE vs. other paths: 
   
  • Reminders: PE isn’t a magical money machine. Plenty of serious wealth is made outside it. Owning P&L, real equity, or being tied to a winning role in some random industry can outpay carry that never vests or funds that don't return properly. Your networks, twitter and the depths of internet are full of these stories so let's not cite them needlessly, I trust you understand what I mean.
     
  • Whether it's operators, ladder-climbers or random startup folks, they often do very well because they’re closer to customers, revenue management and operational decisions. Face it, these are in many ways more enduring skills with a better recycle potential vs. PE skills. Their upside may not be as capped by politics or fund cycles. 
     
  • I'm certainly not here to be making the grass greener, but I meet enough people outside of PE to realize that we are insanely tribal and think of ourselves as a superior race with a totally skewed and broken world view. 2/3s of PE people I have ever worked with would think of themselves as somehow superior and smarter than our targets, bankers and whatnot. That includes myself, even though I argue for keeping this in check. I think it's just ingrained in us. A bit of perspective helps.. especially when they rake it in more than you.
     
  • Returns compress across generations as the industry standardizes. Playbooks spread, alpha gets competed away, processes converge, and true breakout outcomes become rarer. Each cohort fights harder for thinner edges. It's time to accept that PE is just not the space that it was even 15 years ago, let alone 30.
     
  • Because of your ability to play god in PE (allocate money, boss almost anybody around, make things happen and the usual yada yada), it is hard to think outside the box and make a move to the next frontier. Recognize your biases and insecurities and make a call most suited to your ability to take risk. Each and every person has a different temperament, time preference and appetite for risk. The faster you dial in who you are, the easier it will be to choose the path that suits you.
     
• Good work ceases to be enough once you become seasoned — a web of relationships is more important
   
  • You must have multiple sponsors / guardians / key allies across power centers in your firm — these are the seniors you deliver for, who will actually advocate for you. One sponsor helps but a coalition of up to 3 can protect and provide great optionality. The bigger the firm the more important it is to stand on more legs.
     
  • Becoming one very senior person’s go-to (effectively their wholesale bitch) can rocket your trajectory if they are performing and pull you "up" with them. It’s a legitimate short-term strategy, but, buyer beware.
     
  • Key-person risk is real. If they stall, die, leave, or lose influence, your runway can vanish overnight. Betting your career on one person is a long-run mistake. I know it is extremely hard to actively build out strong enough relationships with multiple internal sponsors when you are grinding and barely have time to keep your personal life going alongside work — but it's imperative for long run success in your typical org.
     
  • Aim for two, ideally three, high-ranking sponsors who’ll vouch for you. Once two key people say “yes” reversals become very hard. Decisions calcify in your favor... I really wish I employed this earlier in my career. Can't stress this enough.
     
• It's all just selling at the end of the day. Communication and charisma.
   
  • I saw several above average communicators rise in different domains despite being generally mediocre elsewhere and just about moving the chains in their day to day. There are many flawed characters and over indexed people in the space. You don't need to be Jordan Belfort, you just need to be a slightly better orator than your degenerate peers. Over time, presence, narrative, and brevity routinely beat quiet excellence and nerdiness...
     
  • Great communicators, bullshitters, salesmen, and aggressive, no-compromise types win for a reason — boards, ICs, and recruiters, counterparties of all kind respond to certainty, confidence and a solid story.
     
  • As you rise in PE, you either have to become one of these people or learn to stand up to them or emulate them. That means having to put in the reps to know what you are saying, tight memos, proper presence and keeping conversations on track, plus board and IC craft to handle people. Easier said than done. A top PE operator is always a top politician.
     
• Don’t expect fairness. Respect the powers of collateral damage.
   
  • The investment space is tough and well-paid for a reason. Accept that merit is necessary but not sufficient. No single body of work or one relationship “saves” you.
     
  • Good people often get fucked by politics, idiosyncratic deal dynamics, timing, or random bad luck.
     
  • I’ll never forget what a senior partner told us early on in our career. At the time, I found it shocking and almost nonsensical. Often thought back on the old fool and laughed until I came to appreciate it. He said: “If you can lower your expectations and build a high tolerance for injustice, you’ll all go far in the investment space.”
     
• Founders, management and industry operators are sometimes very underrated
   
  • PEs love taking a massive shit at managers, portcos and make huge judgement calls or dish out fortune cookie advice despite never having sold or built a single fucking thing in their life.
     
  • While many founders or C-levels aren’t “exceptional” in a finance sense of polish, they will be practical, customer-anchored, and have their heads screwed on. They ship, they sell, they keep the lights on. This couldn't be further away from the skillset and attitude of PE people.
     
  • As my career progressed, I found myself weighting their judgment sometimes well-above finance bully partners, lacking any depth, who’ve never solved an operational problem and only see the world through board packs and excel.
     
• The myth of the mighty senior partner 
   
  • Chances are your senior-most people aren’t the Henry Kravises or Ray Dalios of this world. They were surely smart, gutsy, lucky and assertive, sure, but they also won the genetic lottery, came up in the right cycle, and chose the right industry during one of the most extraordinary runs in economic history. Timing built many legends.
     
  • Allow yourself to be cocky, ambitious, and hungry. Drop the imposter syndrome. Every few years, you’ll find yourself a few drinks deep with these multi-millionaire foxes, and they’ll quietly admit they’re not sure they could make it today. Listen closely, that’s not false humility but their recognition that the game has changed.
     
  • They built careers in an era when cheaper money, less competition, and uncharted deal flow rewarded risk-taking and charisma. You’re operating in a world of crowded capital, compressed returns, institutional processes, and walls of many kinds. The skill set required today is fundamentally different. Probably much sharper, more standardized and far less forgiving.
     
  • Don’t mythologize them. Learn from them, respect them, but don’t worship them. The ecosystem that made them doesn’t exist anymore. Their path is closed to you, and yours will have to be carved differently. More strategic, more self-directed, and less dependent on a once-in-a-lifetime tailwind. The new world rewards different predators. 
     
  • Challenge yourself and look at a range of successful founders and their backgrounds to see how they made themselves. 
     
  • Nothing is ever set in stone. Don't let any of these mofos tell you who you are and what you can be.
     
• Even PE work becomes just a people, projects and admin job after some years.
   
  • Days drift from being very close to investments to never ending meeting time, always reviewing docs and doing governance stuff, directing folks and being the fucking guy telling people what to do. 
     
  • Expect to not do any real work but somehow always having endless meetings, high-level wrangling, with a lot of pressure and responsibility to move the ball a couple of yards forward every time.
     
  • The higher you climb, the more meta - and further from ground truth - your day will be. Process, people, optics and papering start to dominate actual investment work.
     
  • Skill atrophy is totally real and something to be respected.
     
  • Unless you want a board-advisor or C-level life, all this PE choreography won’t make you the domain specialist a company hires for specifics. Over time, PE trains you to be a C-level or board person, but certainly not an expert in anything. This can be quite risky for career pivots. Don't think you can run XYZ function or company just because you've been on 15 boards and realized XYZ MOIC on your deals.
     
• Don’t allow PE to be your main thing
   
  • (This is advice for juniors who don't have a family yet.)
  • I certainly made the mistake of over-indexing my life and identity to something that was probably not worth it in the grand scheme of things. Just to remind you, you never get your youth back. Something I always glanced over, but age makes you realize this stuff. Be gregarious and enjoy life while you can.
     
• You need to make some mistakes to learn from them. It probably won't make a difference that you read this post.
   
  • Reading all this is nice; I probably read a dozen posts like this on WSO over the years, but living it is what changes behavior. 
     
  • You will have to touch the stove on politics, sponsorship, portfolio, and that pain teaches faster than any advice. Just do your post-mortems, adjust and move on.
     
• Careers are often made out of nothing, or everything
   
  • If you spend long enough time in the space, you realize people can get exceptionally lucky or unlucky at big and small shops both, with every team structure and life background you can think of. Can be wrong timing, wrong boss, wrong LP mood, wrong time to raise, wrong time to exit, you name it — or the opposite.
     
  • You’ll see the clueless get lucky — and others rise at lightning speed and being rewarded too much, too early. That’s life. Your job is to maximize your surface area for luck while protecting the downside when it inevitably turns.
     
  • The more I think about surface area and genuine human networks, the more convinced I am that it’s the only real safety net. Too many people will tell you to “just move to XYZ fund” or “switch sectors.” That’s not how this fucking game works - the average person doesn't just get 3-5 choices of their liking to pick and choose from. The more you work, the more the organizational pyramid hardens — lateral mobility drops, politics increase, and optionality shrinks. When things eventually go sideways, it won’t be your CV that saves you. It’ll be your network.
     
  • Good people, good grind and good results get recognized at some point. Max out what you’re naturally good at; don’t cosplay someone else if it breaks your modus operandi. But prepare that it will take more grind and more grit to get something done (or recover, if you fell) than ever.
     

  • Lastly and most importantly, don't let anybody ever tell you or suggest to you what you can and cannot do. Not me, not your mother, not your boss, not the government. Only you decide on how you want shape your career and what you are willing to endure to "make it".

    
    “If you can lower your expectations and build a high tolerance for injustice, you’ll all go far in the investment space.”