10 Things I Wish I Knew in College Part 2

A short playbook on success for those kicking off the new semester

For those reading today 9/12! I’ll be hosting an office hours for a16z speedrun with Henry Shi, founder of Super.com ($200M annualized run rate), today 9/12 at 5PM PT. These are live interactive Q&A sessions with top founders and investors to give anyone access to the secrets of how they made it. This is something I would’ve loved to have more of in college as I was trying to figure out how to be a founder or break into tech / investing, which is why I started this series.

Link to signup here, and follow me on X/LinkedIn/Substack for more of these office hours with future luminary founders.

And with that on to the essay!

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Most of what you’re learning in college classes right now is useless, and you know it.

That introduction to science class? That sociology paper you need to finish tomorrow? Probably not the best way to spend your time. The truth is, if you want to learn how to build products people want, create content that matters, or identify who to befriend and date, these are all skills you can develop now outside the classroom.

What taught me the lessons I know now was getting rejected from hundreds of jobs, building products that didn’t ship, surrounding myself with the right people, and forcing myself to stay curious. It was all the stuff outside of classes that taught me the things I know today. Given college is kicking off again this semester, I thought it would be a good time to consolidate the advice I’d give to my younger self.

In Part 1 I covered the philosophy of navigating college and mental models to do so: understanding the system around you, that getting lost is a feature not a bug, and that status is a tool not a trophy. So Part 2 will be the tactical playbook I wish someone gave me when I was 20, sitting in Butler Library grinding on p-sets for problems I’d never see again.

Prepare for a fun little rant with a lot of personal anecdotes.

Learn how to build or sell (what to do)

There are two roles that generate the most value: building and selling. This is what I realized working throughout my time in tech and consulting. At McKinsey the core of what we were selling was: brand (get the McKinsey stamp of approval), knowledge (we’ve done this a hundred times), and manpower (we have a smart team that will work 80 hours for you).

If you’re a consultant, lawyer, or banker, you’re selling knowledge and services. If you’re in tech, you’re creating code and selling code. If you’re in the arts, you’re creating and selling emotions, stories, and beauty. With how our society is structured, we often start with building (essays, decks, code, paintings, products) and move into selling as you get more senior (visions, products, teams, projects, yourself).

A lot of what I learned at McKinsey was how to build trust. How do you make a strong first impression, how do you always overdeliver, how do you understand their incentives so that you’re not just helping the company but the individual person, how do you relate to them on a personal level even if their background is very different to yours. That’s really at the core of selling, is having the other person believe in you and the value you bring.

But you can learn a lot of these skills in college. I used to be the social chair for my fraternity, and I remember curating lists, creating CRMs, tracking open rates, understanding referrals, all techniques that I still use now when understanding app metrics. Digital spaces mirror what happens in real IRL spaces. For some clubs, I went door to door to each restaurant to sell them advertising placement. The key insight there was going further downtown, where foot traffic for Columbia students wasn’t as strong and figuring out ways (like referral codes) to properly attribute lead generation.

Or, I remember my senior project was creating an automatic stroke detection device with a wearable photoplethysmogram. The idea was to detect blood pressure changes in stroke victims, which was one of the earliest signs of stroke. It didn’t quite work during the demo day, but the lessons I learned coding the Arduino and writing signal processing algorithms are still relevant today.

Get leverage on your work (how to do it)

I don’t believe in work life balance. If you want to win and be great at something, you have to put in more hours. It just comes down to priorities. But I grew up in New York, and in New York there’s a lot of work that keeps you busy but not productive. Email work. Appendix slide work. Random memo work.

The thing I didn’t appreciate in college was the concept of leverage. How do you create compounding effects? How do you do 10x with what you currently have? There’s a few forms of leverage:

• Human capital - Convince three friends to go work on a side project with you

• Debt capital - Raise some small dollars for a student venture / fund

• Software - Write code that’s infinitely extensible

• Content - Find your niche and scale your content

• AI - Create automations, search through knowledge, and use software as labor

• Knowledge - Understand and specialize in a sector deeply

This is the leverage I understand now and wish I knew then. I could have started writing and publishing earlier. I could have built and shipped more apps. I could have been more risk seeking and gone deeper in on crypto during the 2017 wave. I could have assembled some friends to go on a great startup adventure.

And even though I chose a specific sector to work on and compound my knowledge, I pivoted several times, from biotech to gaming to AI software. I actually wanted to be on the fast track and had a strong thesis for each new direction, but sometimes you don’t have all the data when you make a bet and you change as a person as you get older.

For me, the bet on biotech was because I loved science, but then I realized how slow moving the pharmaceutical industry truly was and the work that was actually involved. There wasn’t really any science in the day to day, unless you were in the wet lab. The bet on gaming was to be closer to a product I loved. And to this day I still love games. But the bet on AI software was because I simply believe this is the most generational change for the next decade. Consensus to say at this point but it takes a while to fully, deeply appreciate it. And I’ve come to understand with the wisdom of years that these market waves do not happen very often, and they happen extremely quickly.

Anyways the best thing you can do now is choose. Choose a direction and go compound. If it doesn’t work, that’s ok, at least you tried and didn’t stay still.

Find your people (who to do it with)

You may have seen that many of the greats met in college. Larry Page and Sergey Brin (Google) met as PhD students at Stanford. Reid Hoffman (LinkedIn) and Peter Thiel (PayPal) were classmates and philosopher buddies. Bill Gates lived down the hall from Steve Ballmer at Harvard. Why does this happen?

The most talented people that you see around you now are also going to be the most talented people in thirty years. The only thing that separates you from them is time and choices. When I was growing up, I thought there was an enormous gap between the people you read about and the people around me. But as I got older, I realized that the smartest folks around me were going to be the greats of the future. We are the new generation.

A lot of the folks around me now that I used to sit in math class with and go drink beers at the local pub are now researchers at OAI, exited founders, quant hedge fund savants, small VC GPs, etc. Those people you look up to are the same as the people around you, they’re just further along.

But there’s one key in finding the best people. You need to find the right environment. Get to the right city, to the right school, to the right company. Keep pushing until you’re not the smartest person in the room. That’s when you’ll know you’re in good company. Even in my life, I didn’t feel fully satisfied at Columbia, at McKinsey, at Riot, until I landed here at a16z and met some truly top 0.001% people at what they do. The reason there are “mafias” (Paypal mafia, Uber mafia, etc.) is because great people gravitate towards one another.

This might be a weird take, but imo it’s also so important to go on some crazy adventures with those people once you find them. As they say, an interesting person is only born of an interesting life. Ray Dalio road tripped through Latin America after college; Steve Jobs had several spiritual retreats to India. Some of my most memorable experiences were a result of meeting great people and making great memories: hiking Mt. Fuji in the pouring rain, powdery ski descents in Colorado, or late night drives through the hills of LA.

Date (also who to spend time with)

Can’t write a college post without talking about dating. After all, college is a bundle of products and services: credentials, academics, career development, community, and dating. Nowhere else will you meet so many likeminded people, for work, friendship, and for romance. The variance of who you meet will go up after college and your free time will go down. And you’ll likely have to spend a lot more time sifting through noisy signals (aka, swiping left a lot on apps).

It’s also a period where everyone is exploring and finding themselves. As important as it is to cultivate your professional life, your personal life and maturing as an individual are equally valuable. You’ve probably seen the graph of who you spend time with after college, so understanding how to pick the right partner is really important. If you apply the secretary problem strategy to dating, then you must get enough data points to form a reasonable baseline. But I would contend understanding yourself is as important as knowing how to pick a good partner.

A few things I learned about myself through my college dating life as an example:

• Trusting my gut: Easy to say, hard to do. Subconsciously I always knew whether a relationship was going to end, whether one had potential, and whether they liked me back or not. But sometimes I just didn’t act on that feeling. I would often rationalize the situation, convincing myself that it’ll never work out even though I liked her, when really I was just afraid of rejection. Or I would be too infatuated with the idea of somebody to recognize the reality that she didn’t like me back. Either way, I think I intrinsically knew what was going on but didn’t listen to my subconscious.

• Fear of rejection: I hate disappointing people, both by being rejected by others and rejecting them myself. It’s meant that I will procrastinate decisions I know I have to make (breakups) and not take risks because I’m afraid they’ll tell me no (lost chances). The principle I apply to myself now is: the more I want to put off a decision, the more important it is to make it happen right now.

• Hyper-rationality: I’m an extremely rational person and approach many things as a problem to be solved. But in relationships, and especially during emotional moments, what the other person wants is to be heard more than anything else. Having empathy for others and listening well - truly listening and not just waiting for your turn to speak - are both important skills that I had to learn to stop my natural tendency to problem solve.

• The right way to communicate: Words carry a lot of power and should be chosen carefully. You might have good intentions but if said in the wrong way or the wrong tone, they will not come across. Even if you say the same thing, different people will react differently to it. Understanding the right thing to say to the right person in the right way is something I’m still trying to master to this day.

I’m sure you’ll get relationships wrong sometimes, and I’m sure it’ll be painful. But dating in college was very helpful for me to understand what kind of partners I work well with, who I am, and how I handle things.

Take the leap

I was a pretty risk averse person growing up. I think it comes with my Chinese culture; my parents didn’t need me to be a doctor or lawyer but my mom works in risk / AI and my dad’s a professor. Pretty stable career professions. We’re a family of engineers, very pragmatic and EV maximizing. I was afraid of losing in golf so I never competed. I was afraid I wouldn’t get into Stanford so I never tried. I was afraid of losing money in college so I only invested in very stable securities. I was afraid of committing to startups so I went to consulting. So what I’m saying is, I’m really the last person to be giving advice about risk taking.

When I talk with my friends - most of whom just turned 30 so we’re having the “omg we’re 30” moment now - the biggest throughline and regret is not giving it a shot. Asking the guy or girl out, giving it your all for a job, stepping off the golden path, moving new cities. When they say time is short, it takes some time to appreciate really how short it is. There’s cognitive time dilation as you get older, since less experiences are new and each year is a smaller proportion of your memories.

If I had stayed in New York, stayed consulting for big pharma companies, I’m sure I’d still be doing well. But I’d be asking myself what if, what if I moved to California, what if I took the jump to chase after something new. I’ve resolved to never ask myself what if, and just make it happen with conviction. Not all of it has shaped up how I’d like it - it was very lonely in Los Angeles, the gaming market took a turn for the worse, I miss my family - but I have no regrets.

The mentality I’d like to leave you with is, we grow up with many choices made for us: where we live, where we go to school, what we study. And as you get older, the most important skill you can develop is to make your own choices with conviction. No one else is looking out for you. So you better damn well figure it out yourself. The irony is that by the time you have the wisdom to know what you should have done in college, it's too late to do it. That’s why I tried to leave some here. The only question is: will you do it?