In January 2026 I was invited to be on a panel of UCLA Philosophy alumni in tech. I owe UCLA Philosophy a lot and will never miss an opportunity to give back.
Here are the notes I prepared for the event. A couple caveats:
- I have no idea who’s reading this. Maybe nothing is not applicable to you. If I talk in public, my job is to be opinionated and the audience’s job to decide whether what I say makes sense for them. In other words, your mileage may vary.
- When I say “tech”, I mean the world of pre-seed to series ~D startups.
- I have no experience in “big tech”. If you want to work at Google/Meta/Amazon, etc.., I can’t help you.
You made a great life decision and a mediocre professional decision.
Studying Philosophy was one of the best decisions I made. It gave me intellectual foundations I’ll use for the rest of my life. It does not help your career in the short to medium term. There are a couple reasons why:
- Getting a job, regardless of what you study, is hard. You’re asking someone to pay you tens of thousands of dollars to use your brain. For the past couple of years, you have been paying someone tens of thousands of dollars to use your brain as a student.
- Philosophy is illegible to the outside world. Everyone in this room knows how hard it is to crush Phil 31, write an essay for Burge, argue against Descartes, or track what’s happening in Naming and Necessity. Unfortunately, very few other people in the world do.
- UCLA Philosophy, in particular, is illegible to the outside world. This department is one of the best on the planet. I believe you have been trained by some of the best. Again, very few people know that. To a hiring manager, you’re someone from a good school with a humanities degree. Not bad, but don’t expect the benefit of the doubt.
As a result, you’ll need to work harder and be smarter than your peers. I believe in every single person here’s ability to that, but you have to steel yourself mentally for it.
What are hiring managers looking for?
One of the biggest problems with hiring right now is volume. Clipboard gets literally hundreds of applications for new grad roles. When I’m reviewing submissions, I’m also tired and a little cranky because I save reviews for the end of the day.
When I decide whether to interview a new grad, I’m looking for the following:
- Are you an intelligent, thoughtful human being? (not AI)
- Can you communicate well?
- Are you professional and conscientious?
- Is there evidence you can get things done in the world?
Surprisingly, determining 1 and 2 are the easy parts. At Clipboard, we use case studies that mimic aspects of the job to test those. A lot of companies use case studies now for similar reasons. AI will likley make these obsolete soon, but for now that’s straightforward.
3 is much harder. You’d be surprised at how badly people fumble this. I’ve been ghosted for interviews, promised things I’ve never received, seen unprofessional gmeet/zoom backgrounds, read case studies where “shift” is typo’d as “shit” multiple times in the same sentence, and interviewed people who had very little idea of what Clipboard even is despite wanting to work with us.
4 is the most difficult part. Nobody is hiring new grads to “strategize” or think about stuff. We hire you to do things. The best predictor of someone’s ability to “do stuff” is evidence they have “done stuff” before. Examples can be almost anything, but they must be “extracurricular”. “Research” doesn’t count. Things that do count are:
- Played a sport at a high level (e.g. college, semi-pro, competitive club).
- Played a game at a high level (e.g. >1500 ELO chess, net positive in Hold ’em over thousands of hands, won money playing Magic the Gathering, qualified for world bocci ball championships, etc…)
- Started a company
- Worked a full time job to put yourself through college
- Ran a business
- Managed a team in some extracurricular capacity
- Published a magazine over >6 issues
- Dropped out of college for a year, took a mortgage on a house in Denver, fixed it up, and rented it out to a family of two (my third year roomate did this).
- Ran a podcast with biweekly episodes over the course of a year
- Spent summers in Alaska working in salmon canneries for extra cash
- Worked as a “venture scout” for a VC firm
- Had a previous career as a child actor
- Organized large events
- Danced at a high level (ballroom, hip hop, ballet, etc…)
- Had a YouTube, TikTok, Insta, etc… with hundreds of thousands of likes, views, followers, etc…
- Launched a cubesat into orbit
- Rebuilt an old car and now it’s your daily driver
- Built an “app” with thousands of downloads
- Played in a band with paid gigs
If you nail 1, 2, and 3 I may still interview you. However, 4 gives me confidence you know how to achieve outside an academic context.
How do I stand out?
This is the most important section. If you forget everything about this blog post, my panel, etc…, please remember this. I have two concrete ways to stand out to employers:
- Do your homework
I get messages from college students (and working professionals) that look like this:
Hi Riley! My name is [NAME]. I’m a senior at [SCHOOL] studying [SUBJECT]. I noticed Clipboard’s [JOB] and got really excited about it.
[Words about healthcare, how great Clipboard is]
Do you have a couple minutes to chat soon about the [JOB] and your day-to-day?
These are terrible. There’s no evidence this person cares enough to dig a little about Clipboard or me. People (myself included) are wowed when it’s clear someone did their homework. Examples of this include:
- Asking about an obscure company practice
- Learning some about the industry and asking non-obvious questions about it
- Referencing an obscure piece of press and asking about the implications of it
- Sharing a hypothesis about how the business operates and asking whether it’s true or not
- Sharing a blog post you wrote related to the company / industry
- This was how I ended up working with Dwarkesh Patel
- Thoughtfully referencing something the person wrote online
- Having multiple questions ready at the end of the interview when someone asks “and do you have any questions?”
- You’d be amazed how many people look like a deer in the headlights when I ask this.
- Make a personal website
I have gotten every professional opportunity thus far (and two long-term relationships) through my website. Without exaggeration, writing blog might be the single best decision I’ve ever made.
I think personal websites are effective because you, the author, have complete control over the medium. There are no rules, so you’re not constrained by the conventions of a resume, a case study, portfolio, etc…This means I can get to know someone (professionally) more from their website than nearly anything else. It’s the internet equivalent of going out to dinner.
Rejection and feedback
Be prepared to be rejected hundreds of times. In the leadup to Clipboard, I got rejected from 139 jobs. That’s a low number. I’ve heard of people getting rejected from >250 jobs before they landed one. I won’t defend how the job market works today, but you cannot find work without rejection. The first ~10 hurt. Then your skin thickens.
A word on feedback. You’ve been part of institutions that exist to help you succeed your entire life. These are mostly schools. UCLA, the Philosophy department, your high school, your middle school, etc… When you get a C on an essay, fail a test, etc…, it’s part of their job to provide feedback.
It’s not prospective employer’s jobs to provide feedback to candidates. They should be professional and polite, but they’re not your teachers. The sooner you internalize this, the less strife you’ll have. You can ask for feedback, but do not expect it. If they do give feedback, take it with a grain of salt. Employers have an incentive to soften it.
The best way to sharpen your job-search skills is to find someone who has hired people before and ask them for advice. Tell them not to hold back.
Should I go to business school?
Probably not. Your mileage may vary, but I think it only makes sense if 2 of these are true:
- You get into Stanford/Harvard/Penn, or another school with strong specific industry connections (e.g. UCLA/USC for entertainment, NYU for finance)
- Someone else is paying for it
- You want to start a career in finance/banking/PE/VC/consulting (in this case 1 becomes even more important)
The rationale is business school is expensive and the opportunity cost is high. You will learn much more “business” by working in a business.
What do I want out of my career?
You need a clear answer here. Without one, you’ll be frustrated, confused, and make poor decisions. I speak from experience. Nobody expects you to have it figured out in your 20s. However, I expect all of you, as Philosophy students, to reflect on this question, arrive at provisional answers, and pursue your careers in accordance with your beliefs at the time. As you learn more about yourself and the world, update your beliefs and change your actions. If you can’t do this, what good is studying Philosophy?
Here’s a personal example. Money is only one form of compensation. Teachers are compensated in job security and free summers. Musicians and actors (that work) are compensated in “coolness”, activists in fighting for the voiceless, engineers in building things people use, and writers in barely anything.
After I graduated, I wanted to be compensated in “intellectual stimulation.” I wanted every day to be like school where I learn some new, abstract thing and write about it. I also had the fantasy someone would pay me a lot of money and I would be famous or this.
As I got older, I decided this was wrong for me. The real world is very, very broken, but fixable. The bottleneck to a brighter one is people willing to put in the time and energy to solve unsexy problems. Once I realized I could make hundreds of peoples’ lives better by finding ways to complete paperwork faster, or improving how nurses and facilities communicate, I realized I wanted to be one of those “unsexy” people doing real things. I still get my “intellectual kicks” elsewhere, but that’s not necessarily what I expect from my job.