Career Spotlight: Rajiv Asdhir, Investor at Sculptor Capital; formerly Bain Capital & Goldman Sachs
Understanding the value of time, avoiding burnout, and setting rules for your life.
Every month, I feature a high performer ‘Career Spotlight’ and interview them on their journey, mindset, and habits.
Last month, I interviewed Eugene Hayden, Data Scientist — to discuss the recruiting mindset, optimizing your resume, and effectively positioning yourself during job interviews
This month’s spotlight will be with Rajiv Asdhir, Investor at Sculptor Capital — and previously at Bain Capital and Goldman Sachs.
Rajiv is currently an Investor at Sculptor Capital, a hedge fund with US $30B+ assets under management (AUM). He was previously in Private Equity at Bain Capital and Investment Banking at Goldman Sachs.
I met Rajiv through our mutual friend, Angela, who I also interviewed for a Spotlight in March. We both attended school in Canada, play basketball, and are extremely competitive in some regard.
Upon meeting Rajiv for the first time, he immediately stuck me as someone who is incredibly sharp, attentive, and quick-witted — but also focused, determined, and rigorously intentional with how he spends his time and energy.
He’s also extremely well-read, as you’ll see from his responses below.
Rajiv’s done stints at the the world’s top financial institutions — corporations known for their exceptionally difficult recruitment process, and intense and rigorous working style. It's a world where long hours are the norm and the ability to make good decisions under high-stakes is crucial.
There’s a wealth of knowledge below touching the themes of prioritization, ego, performance, and ‘playing the game’ below. It’s a longer read than what I normally publish, but it’s a real treat.
Take your time, read slowly, and while you’re reading — take a step further to think about how these concepts apply to your own situations.
What do you do today? What has your career journey been?
I currently work at Sculptor Capital, a Hedge Fund, on its Long / Short Equity team.
Simplistically, my job is to analyze Companies — like Facebook, Alphabet (parent of Google) — and decide whether we should buy (long) their stock because I think it’s undervalued, sell (short) it because I think it’s overvalued, or do nothing (nine times out of ten!).
It naturally follows that the goal is to make money on the long-side because the stock price goes up and on the short side because the stock price goes down.
The day-to-day is usually uneventful.
It involves tons of active reading and digesting of information to figure out what companies do and how they plan to win in their competitive spheres; however, there are occasionally really exciting moments when you think you’ve found a pocket of “market inefficiency” in that a Company’s ability to win (or inevitability of loss) is not being appreciated by the market. These pockets of inefficiency / opportunity can be immensely profitable to the people who find them first and act on them.
Even though most of my peers in Finance will take a quick look at my resume and feel that I’ve followed a linear path:
Business undergrad → Banking → Private Equity → Hedge Fund
I’d personally say the plan was never a straight shot and involved a fair amount of impulsivity and luck.
I started university pursuing a Biomedical Sciences degree and thought I wanted to be a Doctor. During my 2nd year, I used my extra credit to take a famous Business class at my school and expand my horizons. A good friend was also taking the class and had been dogging me about the fact that I had already completed my medical school prerequisites, and I should spend my senior years learning about something totally outside of my comfort zone by applying to the 2-year Ivey Honors Business Administration program at my school. It was a famous program and, being young and undiscerning at the time, we viewed it as being the most “prestigious” degree coming out of my school.
He called me the night before Ivey applications were due and told me I should submit an application, so I stayed up all night and applied. Lo and behold I somehow snagged an offer and was on my way to a business undergrad.
Even though my path to a business education was random, the allure of stock-trading had always nagged at me as fascinating because of the pure competitive nature of it.
It’s meritocracy at its absolute finest and nothing — not your race, gender, fitness, status — matters except your track record.
A key moment that righted my ship in the direction of stock-picking happened in my senior year when I took a course called “Value Investing” and got my first introduction to the practice of value investing from an awesome professor named George Athanassakos. He was extremely passionate about it and if you listened closely enough, you could start to elucidate the beauty and creativity — two words you probably never thought I’d use in this context — behind investing.
I wish I could say that, after that class, I never looked back, but there was a lot of self-doubt and questioning that naturally follows when you willingly choose to leave one field for another. It’s like being the one who ended a relationship: you can’t help but wonder if you made the right choice.
The difficulty only compounds when you’re humbled, time and time again, by working in the professional sphere after mostly experiencing success in the academic one.
Fortunately for me, I had just enough conviction in the end goal to get through really challenging times and now be in a job that I really enjoy.
You’ve made a few pivots from top companies to other top companies. Can you share some of the thinking behind the pivots in your career journey?
I think I’m a pretty self-aware person and one thing I know about myself is that I’m extremely competitive, and, specifically: I like seeing the scoreboard.
I have a Peloton at home and I love it because I get to see the leaderboard and, in turn, push myself. It’s the same thing with running. I was inconsistent for years, but quickly became addicted once I started tracking my data using a Garmin watch + Strava, and comparing myself to my peers. I’m still not a great runner by any means, but the ability to progress and watch it in real-time is the thing I enjoy most about it.
For that reason, I think the ability to know (without question!) your track record is exciting.
My time at both Goldman Sachs and Bain Capital was incredible for my learning and I’m immensely grateful to both for taking a chance on me.
With all of that said, the allure of public investing was like a magnet attracting / guiding me and I don’t think I could have avoided it without feeling regret later in life. So far I’m happy to say it’s been a really great decision.
Being in such a high-performing industry: public investing — what are the key skills and mindsets you have to optimize for?
Oh boy — a lot here.
I’ll list key skills but I would caution that different skills are important at different points in your career and I’ve tried to differentiate between being right out of college to being in a position where you are trying to take the next step to establish yourself in a domain (where I am now). I imagine that as time goes on and you accumulate more responsibility, “key skills” change
Literal beginning of career: attention-to-detail (unfortunately), attitude (better defined as excitement level, willingness to learn, humility, respect for authority, lack of ego)
Jumping off point: time management, discipline, focus, compartmentalization, self-awareness, persuasiveness, coachability, intellectual honesty
In terms of mindsets / approach:
I view work as I would a game, and you, as the player, get to choose what game you want to play.
You might want to play the “Doctor” game, or the “Lawyer” game or the “Investor” game and in order to play those games you have to learn a set of rules and skills. (Note: you can also think about subsets of those games — I’m playing the management meeting game today where I have to be polished, friendly, respectful)
Once you pick your game, the next general “philosophy” which I believe in is that playing games at a really high level is more fun than playing games at a low level.
I used to play a lot of chess and, needless to say, it is a lot better the more you know because you start seeing patterns develop on the board instead of having someone explain to you how to move your knight.
The other important piece here is that you need to be appropriately challenged. You can’t be a 1200 ELO (Chess Ranking system) player playing a 2400 one, and vice versa. In fact, you don’t even want to be 1200 playing 1600. It’s just not fun that way.
So when you see people throwing up their arms at the age of 24 in burnout and walking away from work, it’s usually because they’re trying too hard to play in the big leagues when they should be playing A ball (sorry for mixing metaphors). I’ve struggled mightily with this last point, but it’s worth remembering that if you take a deep breath and appreciate that you will make mistakes and fail many times before you succeed, you can always get through tough times.
So to tie it back: there’s an addictive cycle that occurs once you start playing the right game, see yourself get better, and then play at a higher level. Once this happens, there no longer is any notion of work-life balance.
Everything in your life starts revolving around the concept of playing the game in a better way.
Decisions that once seemed irrelevant start to resolve themselves around the game you’re playing (I.e. I should eat healthily and work out 30 min per day because it enhances my thinking, I need to sleep 8 hours to play well tomorrow so I’m going to hit pause and get back at it then, etc.).
What’s your philosophy on work and life — and either the balance or integration of both?
Bit of a tangent before I tie it back:
You should think about your time and money as being on a continuum. You can usually trade between the two.
For example, you could do your own laundry for $4, or you could spend $15 to get someone to do it for you. At face value, the obvious decision is to do it yourself. If you think about the time-money continuum, it’s more complex. You could save yourself 30 minutes to an hour by paying someone. (FYI: don’t think it is a coincidence we use the verbiage “spend” your time…)
Well, the next obvious question is: how much is your time worth? That’s a harder question and has no straightforward answer. To try and get to it, we have to pull in the concept of marginal value from economics.
If you’re unemployed then you have a lot of time on your hands and probably not a lot of money. If you’re working then it’s the opposite. Needless to say, the unemployed person should find zero marginal value from time; what else are you going to do with your time? But the employed person should find the marginal value of time to be enormous. 30 minutes is the difference between a workout and not — which, over years, is the difference between health and illness.
So now let’s do a bit of math on your time. If you work 12 hour days and need, on average, 8 hours of sleep that leaves just 4 hours a day. 1 hour to get ready, 1 hour to eat and 1 hour for fitness leaves just 1 hour of free time per weekday. We should add in weekend time too — assuming zero work, you have 16 hours each on Saturday and Sunday. That’s a total of 37 hours per week for: socializing, reading, proactive work, dates, sports, movies, games, calling your family.
We haven’t even started talking about lost time — what % of your time is actually lost to dead time? Maybe 20%? So it’s really 30 hours. That’s 1,500 hours a year, give or take, to get the thing we call “life” done.
The math on laundry is harder now, ain’t it? How about the math on cleaning? Commuting? Every marginal hour of time is ridiculously precious when you don’t have a lot of it.
Now let’s think through strategies to deal with these truths. How can you multiply your time? I don’t really believe in multi-tasking, but there are basic things you can overlap. You could save an hour by walking while you listen to a call. You could meal prep on Sundays to save cooking time. You could automatically filter out useless emails on Outlook.
A really beautiful thing starts to happen once you reinvest and compound your time.
For example, what if you reinvest one saved hour into reading?
Well if an average book takes 10 hours to read then that’s roughly 1 book every 2 weeks, or 25 more books per year. Reading will compound your knowledge (nodes of knowledge connect in the brain exponentially, not linearly), which will make you faster at work.
If your rate of improvement in efficiency is 5% per year, that’s a 63% increase over a decade, and 600% over a 40-year career.
Imagine turning a 12 hour workday into 2 hours of work. That is the literal equivalent of adding years to your life. Or, it is the difference between being CEO and mid-level management.
To bring it back to the question, my philosophy on work and life is that time has fluctuating and, occasionally, wildly expensive marginal value, and that work and life have to be integrated because both take up the same source of valuable and finite time.
However, it’s not quite a zero-sum game because you can be clever in how you spend your time to maximize that resource.
Your goal, always and forever, should be to make your life more automated and efficient to give yourself more time to do the things you want and that are meaningful to you.
What’s the best piece of advice you’ve received prior to entering the world of finance?
I came across this quote a few years ago and I think it’s amazingly powerful:
“Nobody tells this to people who are beginners, I wish someone told me. All of us who do creative work, we get into it because we have good taste. But there is this gap. For the first couple years you make stuff, it’s just not that good. It’s trying to be good, it has potential, but it’s not. But your taste, the thing that got you into the game, is still killer. And your taste is why your work disappoints you.A lot of people never get past this phase, they quit.
Most people I know who do interesting, creative work went through years of this. We know our work doesn’t have this special thing that we want it to have. We all go through this. And if you are just starting out or you are still in this phase, you gotta know its normal and the most important thing you can do is do a lot of work.
Put yourself on a deadline so that every week you will finish one story. It is only by going through a volume of work that you will close that gap, and your work will be as good as your ambitions. And I took longer to figure out how to do this than anyone I’ve ever met. It’s gonna take awhile. It’s normal to take awhile. You’ve just gotta fight your way through.”
— Ira Glass
This one really hit home for me. I’m not saying I have this killer taste, I wouldn’t even focus on that part of the quote. Focus instead on the part about your work disappointing you. I don’t know anyone who hasn’t experienced this. Pretty much everyone I’ve talked to has experienced imposter syndrome because they take such a self-critical view of their own work.
The funny thing is (and I’m going to get super meta here) that self-critical view is the thing that will cause you to ultimately succeed. It doesn’t matter that your work is currently bad.
It’s that you care.
Your only goal is to avoid burnout. This is not easy for everyone. Especially for those people who’ve only ever experienced academic success. But if you make it through alive then the rewards can be incredible.
Put simply: stay committed, don’t burn out.
How do you perform at such a high level for extended periods of time (i.e. work investment banking hours)
You need to build both efficiency and flexibility in your life.
I spoke at length about efficiency earlier so I’ll avoid that topic here except to state that you should always look for ways to become faster and more automated — aka plagiarize, ask people how to improve, be 80/20 on your first iterations of a project.
On the topic of flexibility: working really long hours and, perhaps more importantly — not knowing when those hours will come, is a tough situation. You basically have 0-2 “free” hours per day, so you have to be really thoughtful about how to spend them. I have three insights that are hopefully helpful.
The first is to prioritize your life.
Buffett is (wrongly) attributed a famous passage that says something along the lines of: write down the 25 things you want to do in your life and strike down the bottom 20.
I believe it’s more severe than that.
You can only master one thing in your life, and then have 1 hobby where you are really good. If you have 2 hobbies, then you’re probably average at both. In this vein of thought, when you have limited time there’s only two things that matter: meaningful time with significant people (immediate family, relationships, best friends), and personal health (exercise and diet).
Everything else is irrelevant in the short term (frankly, everything else is probably irrelevant in the long term too, but we’re human and we like to have fun).
The second is a direct extension of the first — do the things that matter right away in the morning. Never compromise on this.
You can’t rely on yourself to do anything after work because a) you don’t know when you’ll be done, and b) you’ll probably be drained from expending mental energy. If this means working out and calling or seeing family in the morning, do it.
The other important benefit of this is that you will now be fully committed to work. There is nothing holding you back at night and this is an unusual advantage over your peers. You can’t let yourself compromise for any reason.
“I don’t want to run today because I have a morning call,” quickly transforms into “I don’t want to run because I had a late night.” These thoughts are insidious because our brains are wired for laziness.
Finally, focus on sustainability.
I get it as much as the next person:
After a long week, you “need” a glass of wine (or ten) on a Friday night. Fine. But beers every weeknight during a live deal is not sustainable. You will fail and burn out in the long term.
Once you’ve internalized the importance of sustainability, build it throughout your life and keep improving it.
Don’t drink coffee after 4pm and try to avoid it on weekends. Eat healthily, avoid drinking too much, and even avoid working out too much (weird one, but it’s true!).
On discipline and building habits — what is your philosophy for work and life?
Set rules vs principles for your life
Find effective ways to change unwanted behavior
A lot of really great business leaders talk about making rules for your life instead of following general principles.
This a really powerful concept. Rather than saying “I want to drink less” you say “I don’t drink on weeknights.”
The benefit of doing this is that you no longer have to spend the mental energy on a) figuring out whether or not you should drink, and b) actually fighting off your temptation when you decide you should not. It’s a much easier way to live your life.
The cool thing about this is that it’s easy to remember and enforce, and it gets the ball rolling into developing into a better version of yourself.
If you wanted to start getting in the habit of running, you might start out with a simple rule — “I run every day.” However, as I found out recently, running every day could lead to a stress injury.
So let’s say you get a minor injury, you rest up a bit and then get back into it, but your rule for running becomes more complex — “I’m going to run 5 days a week, and if I feel knee pain then I’m going to stop.”
It’s really tough to get to that more complex second rule without first trying out the simple one. The complex rule requires a tracker, it requires intuition on knee pain vs. body ache, and it’s not that catchy! If you had already developed the habit of running daily, it’s much easier to convert and remember the more complex rule.
Eventually your rule will become more and more complicated — “if I run 20km, I need an extra day off. If I do intervals, I can’t follow that up with another hard run, etc.” — but your brain will also develop intuition around the rule. You won’t even need to think about it.
Eventually the rule becomes a habit, then a lifestyle, and then, finally, it gets folded into your identity: “I run.”
What folks would you recommend pursue a career in finance — and who would you recommend stay away?
The latter question is easier so I’ll start there.
Stay away if you:
Genuinely view work as an “enabler” of life, and are not committed to it as a central piece of your identity. Aka you view labor as a trade off for money
Struggle with authority / hierarchy - unfortunately this does exist in this job, and usually for pretty good reasons
Feel personally hurt or attacked when your work is criticized
Have never competed in anything and/or think competition is dumb - this job is fundamentally about competition, prisoner’s dilemma abound
Don’t believe you can sustainably beat the markets
Have another passion but are being temporarily swayed by money
On the flip side, I think the only meaningful thing I can say is that if you think it’s interesting you should do it.
The economic trade off, especially early on, is great enough that if you’re smart and curious about it, it’s worth your time to try out. The exit opportunities are good enough and broad enough to justify the effort.
What advice would you offer those wanting to go into capital markets or private equity?
Break down your ego.
The best case scenario for you if you haven’t worked in this field is that you’re an awesome analyst / researcher, and you can drive start to finish on the gathering and presentation of facts. That’s step 1 of this job. If this is you, that is valuable, but it doesn’t make you a rainmaker.
Step 2 is pattern recognition, and that can only be built by analyzing hundreds of businesses.
You need to break down your ego because even the least capable analyst on the planet has seen more businesses than you, and has a ton they can teach you. In fact, everyone on the planet knows something you don’t, and learning how to incorporate and interpret unstructured information from various sources requires that you ditch the ego and open your mind.
Learn about Uber’s employment issues straight from an Uber Driver, not a fancy consultant. Learn about PPP from your barber. Chat Nike and sports apparel with your Sneakerhead friend. Ask your parents, not a banker, when they will travel again and on which airline.
For completeness, I’ll mention that Step 3 is psychological — how to deal with losses (including opportunity cost), how to take advantage of market dips, how to stay disciplined in the face of exuberance, etc. Even now, I’ve only begun dealing with step 3 so don’t worry about that just yet.
Before Rajiv shares a few resources, I wanted to plug his Substack — The 20 Minute 5k.
He’ll be documenting his journey towards achieving a personal fitness goal. If you’re interested reading more about his ideas on fitness, mentality and success, head on over to his blog: The 20 Minute 5k.
I could list a lot more but I tried to keep this to only books that I thoroughly enjoyed from start to finish.
For the free spirits: To Shake the Sleeping Self, Jedidiah Jenkins — for people who have become disavowed with working life, don’t turn to a self-help-pick-me-up. Hear it from Jed on what it means to give up your boring corporate life and chase a crazy dream. You‘ll be surprised on how it makes you feel.
For the naturally curious: A Promised Land, Barrack Obama — 20+ hours of Obama taking you behind the scenes on the journey to, and performance of, the most important and difficult job on the planet? Hell yea.
For the creatives / imagineers: The Name of the Wind, Patrick Rothfuss — take a maniacal perfectionist and throw him or her at the world of fantasy fiction and you get The Name of the Wind. This is the only book I’ve ever re-read. My only regret is that I loaned it to my girlfriend. Sorry in advanced for bringing you in to the 10+ year wait for book 3, but masterpieces take time.
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Appreciation & Support
Rajiv — I know you’re incredibly busy yet still took the time to put effort into this partnership. Thank you so much!
For those wanting to connect with Rajiv:
Rajiv has kindly offered to share his details openly here. If you reach out, please be respectful, courteous, and intentional.
To those reading: thank you for taking the time to read this.
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