Ryan Choi (Edition # 14)

Ryan Choi (PM & Engineer at Y Combinator)

If you are interested in reading more interviews, just like this one, with founders, operators, and investors from today’s leading startups / companies, feel free to subscribe below!

Some of our other popular interviews: Joshua Browder (Founder & CEO at DoNotPay), Jeff Morris Jr. (Founder & Managing Partner at Chapter One), Ashley Brasier (Partner at Lightspeed), Domm Holland (Co-founder & CEO at Fast), Lori Coulter (Co-founder & CEO at Summersalt).

(Ryan Choi, PM & Engineer at Y Combinator)

We are excited about today’s Edition of The Takeoff. Today’s interview is with Ryan Choi, PM & Engineer at Y Combinator. He focuses on YC’s Work at a Startup, a site to help students and full-time engineers find great roles at YC companies, from 2-5 person startups to larger ones like Instacart and BREX.

Y Combinator is a startup accelerator that invests in a large number of startups twice a year. Companies selected to participate in one of Y Combinator’s batches receive $150k in exchange for 7% equity. Notable companies to go through Y Combinator include Stripe, Airbnb, Cruise, Coinbase, DoorDash, Flexport, Instacart, Dropbox, and Brex, among others.

Prior to joining Y Combinator, Ryan was Lead Product Manager at Lyft, Head of Partner Engineering at Twitter, Head of Product at StyleUp (YC W13), and the 7th engineer at Salesforce.

The interview took place via a call between Ryan and Michael Spiro (Founder at The Takeoff) in early May.

You can see open roles at https://www.workatastartup.com and find Ryan on Twitter @rchoi.

We hope you enjoy today’s Edition.

Michael: To start, could you discuss a bit about your background and how you got to your current role at Y Combinator?

Ryan: Absolutely. I’m an engineer by training — I went to UC Berkeley for undergrad and studied CS. Right out of college, I got to be an early engineer at Salesforce, and it was incredibly satisfying to build things that had a direct impact on the business. 

Later in my career — at Twitter and Lyft — I ended up getting into management, and I’ve learned, in the same way, that you can build a team to help grow the business. And, you can also help people accelerate their careers, which is tremendously rewarding. 

Somewhere along the path, I also started a YC company that didn’t do so well. That brought me into the YC network, and when they reached out about this hybrid product/eng role, I was super excited. They already had a website called Work at a Startup, where hundreds of YC companies were looking for engineers, product managers, and designers.

I run that now, and I also spend a ton of time coaching founders on how to hire — to recruit, do outreach, interview, compensate, and anything they need to get them going and help build teams. Hiring people is one of the most difficult and, in some ways, most game-changing things that founders can do early on. So getting it right is pretty important. 

Michael: Awesome! What is the most rewarding aspect of helping and coaching founders in the early days of their companies?

Ryan: Not only do I get to help founders hire great people, but I also help people find their dream job. There are over a thousand YC companies, and if somebody tells me what they’re looking for, there’s usually a YC startup in that space. 

While you can do research on what jobs are out there, there’s bound to be a few you miss. In those cases, I get to be a matchmaker, making introductions to founders. I had somebody from my MIT network reach out with a background in Mechanical Engineering, and the founder hired them a few weeks later. That was tremendously gratifying. 

Michael: What opportunities exist for students to get involved with YC companies through the Work at a Startup program? I know there is also the internship program, but can you maybe discuss a little bit more about some of the opportunities that exist for students?

Ryan: Yeah, the internship program was pretty fun last year — we had about 60 students find summer jobs at YC companies. You can see the companies still hiring for this year at https://www.workatastartup.com/internships/. They’re looking for engineering, design, and even a few product roles, and there are even more founders who are opportunistically looking, if they see somebody on the platform. 

If you’re looking for an internship, I would also recommend being very proactive. Companies don't know what you can do, and it often helps by lowering the bar for them to decide — by suggesting projects, contributing to open source libraries, and making yourself and your skillset more apparent. By doing so, you're going to get a lot more responses. 

In the event that those don't hit, you can ask for referrals at companies that you think might be a good fit. It might sound like a strange strategy, but founders know other founders. There are communities of founders and maybe one specific founder is not hiring, but there is another one that is. So, being able to have that dialogue is something that I recommend.

Michael: Any other tips you recommend?

Ryan: Oh, one other pitfall I see is that people use the same resume to apply to a lot of different jobs. I suggest tailoring your resume to the role that you are applying to. Your resume should tell a story about why you’re a perfect candidate for a job. It’s unlikely that there’s one resume to tell that story for twenty different roles. 

Often, I see people who put everything and the kitchen sink on their resume, hoping that a company will bite. Sometimes that has the opposite effect because it looks like you don’t know what you want, and people are less likely to engage with you. 

Tailoring your resume and crafting a story takes more work than just sending your resume to a company. It’s a skill you should work on now and will benefit you throughout your career. And if you want a couple of pointers on your resume, shoot it to me: ryan@ycombinator.com.

One caveat: I tend to be very honest, so if you are very sensitive and don't like that, let me know beforehand and I'll just tell you how good it is. But you might not actually learn anything. 

Michael: Really great advice there. We’ll do a bit of a lightning round here; maybe 60-second or so responses to each question if that’s possible.

What are some of the key skills that students who want to work in product should develop while in school?

Ryan: The thing that I think is most helpful is being analytical. Being analytical is the first stage of understanding what you're trying to do, and what metric to measure to know you’re making progress towards your goals. If you’re not analytical, you can have a lot of activity but still not know if you’re making any impact. 

The second is prioritization. At Lyft, you have a million things you could build or do, but you have to prioritize what could have the biggest impact. And at what level of effort. Everything in Product is a game of trade-offs, and the key is making the right ones with the limited resources you have on hand.

Michael: Say a student has two internship offers: one at a high-growth startup and another at a well-known, more established tech company; both offers in product or engineering roles. How should that student go about evaluating those two opportunities?

Ryan: It fundamentally goes back to, “Where do you want to learn?” Do you want to learn at a startup, roll up your sleeves, and learn to build and ship stuff over the summer? Or do you want to be at a larger company, learn a bit more of best practices and big company operations, but maybe not actually ship anything? I saw a lot of the latter at larger startups like Twitter and Lyft. 

In college, you get three or four chances to try something new each summer. You don't really get that flexibility after you graduate. So make the most of the opportunity to figure out what you like and don’t like about different roles and companies, and hopefully that will inform what you’d want to do after you graduate. 

Michael: In terms of maximizing learning, would you recommend students do a different internship every summer so that they are able to kind of see three different types of businesses, three different roles, and three different organizational cultures?

Ryan: I did when I was in college. I worked at Lockheed, at Sapient (which is a consulting company), and then I worked at a tech incubator. Those experiences helped me learn what I liked about writing software, and what kinds of environments and people I liked working with.

Michael: Amazing advice there! I know that some of our subscribers are interested in one day starting a company. How helpful is Y Combinator for first-time founders?

Ryan: I’m obviously biased, but I think it’s a game-changer. At a minimum, it is a very practical, pragmatic experience of how to start a company. Our partners have learned as founders of their own companies, as well as by guiding thousands of founders on their own journey. During the batch, they share their insights and mistakes and tips, so you learn faster and avoid those same pitfalls. 

As a founder, you only see some of these problems once during the life of your company. The partners see them repeatedly and coach and advise you through it. I'm not saying that every time you should follow exactly what they [our partners] say, but what they say is coming from experience that they have gained and can help shortcut a lot of decisions. 

You obviously still have to be a great founder to build a great company, but why not benefit from the network of advice and experience and so many other things that YC offers.

Michael: We are obviously going through a crazy time right now with COVID and everything that is going on around that. Have you seen any big changes in the startup landscape so far as a result of COVID? 

Nearly every company has been forced to go remote, and I know that the YC summer batch will be remote, too. Have you seen any changes that you think will stay or certain things that are only really short-term?

Ryan: People have always been talking about remote work being the next big thing, and maybe there wasn't as much of a reason for all of us to learn how to do it until now. I'm hoping that in the long-run, we do find the right ways, mechanics, and social dynamics to make remote work a success.

We've seen a lot of tools and innovation focused around making remote work… work. There is a company called Tandem that is building an amazing product for remote work — not necessarily trying to replicate what an office looks like, but to make tools that are unique in themselves. YC is seeing a lot of this type of thinking, and it’s pretty exciting to help out there. 

Opening up remote work also means that we’re going to be able to have talent contribute from anywhere. There are great self-taught developers in Python and Rails in other countries, and being able to unlock those individuals and give them more opportunities is something I am incredibly bullish on, longer-term.


** Please note that our interviews may be edited for length, content, and clarity **

Moderator: Michael Spiro (Founder at The Takeoff. Junior at Washington University in St. Louis. Summer Analyst at JMI Equity.)

I’m on Twitter @mspiro3 👋

Enjoy The Takeoff? Help us grow and expand our impact by sharing our Substack.

If you enjoy The Takeoff, why not help us grow by sharing The Takeoff with your family, friends, coworkers, etc? Sharing The Takeoff with even one person means a lot to us (compound growth!), and we thank you in advance :)

Share The Takeoff

Also, be sure to check us out on LinkedIn and Twitter to stay up-to-date on relevant news and information related to The Takeoff.