I've been getting a lot of questions on how I got my first job at Harper (YC W25). My answer has been simple: study the founders or decision-makers, and do strategic cold outreach.

To be honest, I sent 12 cold emails—and 5 of them hit. By "hit," I mean I got some sort of response. Out of those 5, I landed 3 interviews. Harper was kind enough to offer me a work trial online. I performed really well, and that turned into an in-person trial, which eventually led to the full-time role. So shoutout Harper for taking a chance on me.

That's a really solid hit rate, and while most of it was luck, most of it came from spending over an hour crafting each piece of outreach.

Preface

just to preface - this whole playbook is just to get in the door. once you're in, its up to you to actually work on getting the position and keeping it.

for me that meant staying late, working my ass off during a two week work trial, taking initiative, working close to the decision makers, making sure i put in my all and really understanding what i was getting into.

i think this is really important because i made this mistake early on - dont think the job is done by getting the interview. the first step is getting the interview, then its getting the job, but the hardest part is consistently working week over week so your value to the company keeps increasing.

every week you should be better than the one before and show consistent growth. if these things aren't there, you are not valuable enough to the company imo. sure this can vary depending on certain things but overall it should be consistent.

and if you aren't improving, you should notice it and fix it by asking the right questions and talking to the right people. cold outreach gets you the opportunity - everything after that is on you to execute.

Why Cold Outreach Actually Works (vs Just Applying Normally)

• It signals initiative: You aren't waiting to be picked. Founders love people who create their own luck—cold outreach is a direct signal of that.
• It bypasses all the noise: You skip HR, algorithms, and application queues, going straight to the decision-maker while others are stuck in Workday.
• It creates asymmetric upside: Even if they're not hiring, showing strong signal can lead to custom roles or internships. Some of my best conversations came from companies that "weren't hiring."
• Tailored = Trust: Showing you've invested time and energy into your outreach builds immediate trust, which is rare.

The Foundation: Studying Founders (This is Everything)

Before reaching out, take time to deeply study the founders and the company. Understand how they think, what they value, and how they communicate—especially the subtle language shifts they use. Founders notice these details, even if unconsciously, and reflecting them builds trust fast.

where to look:

• twitter/X threads (even old ones—this is pure gold)
• interviews on youtube or podcasts
• linkedin + their early job descriptions