Off the beaten track with Sahil Bloom

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This week’s article is a deep-dive into the strategies and tactics of one of the most successful content creators and educators in the personal finance and investing space.

Sahil Bloom was an investment banker managing over $2.5 Billion in assets, making Vice President in his twenties, set for what seemed like a lucrative track in Private Equity. Then when everything was going great… He quit. Since then, Sahil has gone on to share his knowledge of investing, personal finance, and wisdom publicly on Twitter, building a following of 912,000 followers in less than three years. His Curiosity Chronicle newsletter is packed with wisdom.

I got the chance to sit down with him and ask him a few questions about how he managed to rise to the top of the corporate ladder so fast, why he quit, what he considers the North Star of his life now – and to round it off, I asked him 10 key questions to figure out his philosophy for life. These are insights that you could practically apply to your life regardless of the career track you work in.

Sahil entered the world of Private Equity in his early 20s, right after graduating from Stanford – and he became a Vice President by the age of 27. By any standards, that seems like a rapid pace of progress. When I asked Sahil, how he climbed the corporate ladder so fast, a few of his tips intuitively made sense: First impressions mattered a lot, working hard at the start went a long way, and being a team player made people comfortable around him.

But two of his insights were especially valuable, and can be applied by anyone in any career track:

The Private Equity firm that Sahil worked for focused on mid-market businesses. Sahil’s initial expectation was that he would be sitting at his desk grinding out numbers on Spreadsheets, but the things he had to say “yes” to got quite outlandish at times. Once, he had to fly to Louisiana to inspect the conveyor belts in a catfish farm that his firm was considering investing in. At another time, he was driving through Midland Texas, inspecting pump jacks in open fields. He even helped one of their retail partners fix store signage in Fargo, North Dakota!

When you’re fresh out of Stanford, this isn’t the kind of work you have in mind, but those experiences were so rare and invaluable. They also gave Sahil a sense of what the real problems at the ground level were – He got a peek into the processes of companies, saw how businesses were run, and helped them find things they could improve. The most important knowledge is the stuff you can’t pick up from a book.

Undergraduates from top schools have a peculiar problem that could put a damper on their growth without them even realizing it. A lot of the analysts in the PE firm had to talk to mid-market business owners, but armed with stats and concepts and jargon, the analysts would sometimes talk down to the business owners. These businessmen were talented individuals with millions of dollars in revenue and profit, and obviously, being talked to in this manner didn’t sit well with them.

Sahil avoided this pitfall because of an unlikely advantage – He was a baseball player in his college days. Talking about baseball and sports and “keeping it real” made him relatable to business owners. They didn’t feel like they were being lectured on their own expertise, and they trusted Sahil, helping him grow faster. His athletic training also made him seek out feedback immediately and he would turn to more experienced colleagues for their advice on how he had done.

No matter which field you work in and regardless of your technical skills, the value you can provide is determined by how well you help people. Sahil notes how young college graduates don’t talk down to others to show off – it could stem from an insecurity that they need to demonstrate their value to the other person, but it ends up being counterproductive. If you really want to add value, say yes to as many opportunities as you can, listen carefully to the other person, and solve their problems.

Despite being immensely successful at his occupation, Sahil had a nagging feeling that this was not the kind of life he wanted long-term – especially because he wanted to spend more time with his newborn son. It came to a peak when Sahil had a conversation with a friend who told him bluntly that he was living somebody else’s life – and that triggered a panic attack. The next morning, Sahil found himself face down on the floor, with his chest constricted, unable to move. He decided that he’d had enough and had a serious rethink about how to live his life.

Sahil talks about this as a metaphor in terms of climbing mountains. Sometimes, you start climbing a mountain and realize halfway through that you are climbing the wrong mountain, and you can see another peak in the distance which suits you better. But to climb the right mountain, you would have to go back down, undoing all the progress you made over the years. Most people choose to continue climbing the wrong mountain… But it could be essential to take that step back for real success.

When you have a family depending on you, a secure career track, and a comfortable lifestyle you’re used to, making a sudden change can be difficult – But the panic attack was a reality check for Sahil, and he decided to quit his job and move to the East Coast. The question still remained... What was the life change Sahil needed to make? How did he re-orient his life purpose to find more happiness and make more money than he ever did with Private Equity? What daily practices does Sahil follow?

Read on to find out.

After quitting his job, Sahil had two options before him which he described to a friend: “I can either find a job at another investment fund in the East Coast and continue as an investment analyst, or I can double down on myself, continue to build businesses, and follow this path of content creation…” The friend’s response was “It looks like you’re trying to pick between something that sucks and something that you find really fun – why is there even a decision to be made here?” That shifted Sahil’s perspective.

Another worldview-changing moment was when Sahil talked to his wife about quitting his job and going full-time on content creation. In his head, it was a crazy idea because he was thinking from the perspective of leaving something safe and secure for the uncertainty of starting from scratch. But his wife reframed it for him: “Well, you don’t really like this thing you’re doing and you’re already making a bunch of money doing this thing you love just on the weekends. Imagine if you did it full-time!” That was another revelation that made him take the leap.

Sometimes we’re so stuck in our own vision of the world that an external perspective can show us things about ourselves that we miss – it’s important to have friends, confidantes, and mentors who can spot these for you.

One of the most striking things about Sahil’s approach to life is its simplicity. He doesn’t have a bunch of rules or constraints to figure out what he should do. Instead, he has just one North Star to orient all his decisions, which sounds absurdly simple: Sahil wants to coach his son’s Little League team.

But then, he unpacks how this impacts all areas of his life. To achieve this North Star,

Instead of setting an arbitrary goal like “I want to make X dollars by age Y”, Sahil has oriented his life around one thing that is important to him which will ensure that all areas of his life will be set in order. There’s an actionable tip here: Imagine your ideal life situation based on what is important to you and let that guide you, instead of letting social standards dictate your actions.

Setting a vision is hard, but becoming the kind of person who can achieve that vision is a tactical matter. Sahil spoke about how one habit of his has helped him face difficult challenges in the last few years – He wakes up early in the morning, and regardless of what the weather is outside, he plunges into a barrel of ice-cold water in the morning for anywhere from 3 to 7 minutes. If that sounds easy, let me tell you, cold water can make seconds feel like an eternity.

There’s a ton of scientific evidence backing up the benefits of a cold plunge, but Sahil said that the crux of his habit is psychological: By doing one incredibly hard thing that he doesn’t want to do immediately after he wakes up, every challenge that he faces later in the day seems trivial in comparison. And even if he doesn’t accomplish anything noteworthy through the rest of the day, his morale is still maintained because of the hard task he did in the morning.

Try incorporating one hard task into your routine, and it could change the way you approach challenges in the rest of your day.

Finally, I asked Sahil ten questions which revealed some precious (and fun) insights into stress-free productivity and optimizing for a life of well-being:

1. If you lost all your skills today, what is the first thing you would do to get back to where you are now?

If I lost all my skills, I would really focus on building back that foundation as fast as possible. Given it would be difficult to become the most skilled (working from behind), I’d likely focus on building a foundation there and then really prioritize relationships. Getting in the room with smart people and providing value for them in any way would be where I would spend most of my energy.

2. What's a business philosophy that you feel is under-appreciated?

Working hard isn’t overrated. It has become trendy to say that working hard is overrated and that working smart is all that matters. Working hard early in your career sets you up to know where to work smart later.

3. What do you wish you had spent more money on?

I’ve always spent quite freely on things that matter to me (and skimped on things I don’t care about, like watches, cars, etc.). I don’t really have anything that I wish I spent more on.

4. What do you wish you had spent less money on?

I probably wouldn’t have bought my 7th-grade girlfriend that ruby ring, because she broke up with me a few weeks later and kept it.

5. What was your most significant failure, and what did you learn?

I gave up a grand slam on ESPN to lose the super regional championship game in 2012 while I was pitching at Stanford. This was a public failure on a level that most cannot comprehend, but it really shaped who I am today. Bouncing back from that pitch to get the next batter out is the lesson I remember today.

6. What do you wish you could have done differently, knowing what you know now?

I would have been a kinder human being in my insecure teenage years. I tried to cover up my insecurity by puffing myself up and taking on an arrogant persona. This is embarrassing to me in hindsight, and I wish I had just confronted my own insecurities and developed a confidence in myself and my core values.

7. How much of your success do you attribute to luck?

I believe that 90% of where we are is due to factors completely outside our control (where we were born, who we were born to, etc.), but that the last 10% is all up to us. People who focus on the 90% will never make it. Those who focus on the 10% are destined to win.

8. What is one skill/process you have invested in that has given you the highest returns?

Daily walks where I can just think have been the biggest unlock for my life. I don’t listen to podcasts or audiobooks, I just walk. It’s where I have all of my best ideas now.

9. What's currently holding you back, and how do you feel you can best overcome that?

My desire to do more is usually the biggest blocker to my progress. I need to embrace a less but better mentality.

10. Do you think it's more important to spend less or make more?

I think the most important thing you can do is find your version of “enough” and embrace it.

That’s it for this week! Let me know in the comments which insight resonated with you, and whose strategies for success you would like me to break down next.

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You can check out Sahil’s writing on Twitter and in his newsletter.

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