Over the past four years, I’ve interviewed thousands of candidates and extended offers to about 40 people.
I’m 27 years old and to this day, I have never been on the other side of the job interview.
Instead, I’ve started two companies and successfully raised venture capital for both. Learning how to hire has been the biggest unlock for us.
How to think about hiring
2026 feels like the year of layoffs. Coinbase, Meta, Snap, Oracle have collectively laid off tens of thousands of people. Many point to efficiency gains from artificial intelligence as the reason for less personnel.
As an AI startup founder, I can tell you that strategically building a team is the only way you can move in days instead of months. The first principles I’ve learned are:
- Hire the people who are spending their nights and weekends working on the same things.
- Find people near your network. Friends of friends, online, cold outreach to people doing interesting work in your space. Do not outsource this part.
- You will get what you optimize for. If you want to have a team of ex-Meta engineers, you’ll be able to find five people matching that credential. But, typically it’s the person who rejected their Meta offer and spent a year going from zero to 50,000 users who’ll fit your culture better.
Hire people who are already doing the work
Three years ago, I hired an 18-year-old to be a community ambassador. The role was simple and required about five hours of work per week. The person we hired was already spending 20-30 hours on our app building community for us.
In three months, he outgrew that role and became our Head of Community. He grew our Discord server to over 200,000 members and increased the number of creators on our platform fourfold.
Since then, he’s been a founding engineer and our lead mobile app developer. He’s only 21! And he still spends his free time on Shapes. Hire someone who is already doing the work: That way you can spend time dreaming and executing with them instead of persuading them to work.
Skip the recruiter
It seems everyone has a recommendation for a recruiter that runs an agency but “is a good one.” We fell for it and spent more than $100,000 on it. Until your team is 50 people, it doesn’t make sense to work with a recruiter.
Why? A few reasons:
- Recruiters run in cycles of quarters, not weeks.
- If you work with a recruiter, you lose the first two months just calibrating on the company’s mission and culture fit.
- Recruiters are biased to make any hire (that’s how their fee structure works!) and to pattern match candidates with credentials. Even if you don’t tell them what to pattern match for, they’ll ignore obscure talent.
Your role as a startup is to invest in early talent. The only person who can do this is you. Some of the best hires I’ve made have come from anonymous anime profile photos on Twitter. The worst hires I’ve made have come from job boards like AngelList and LinkedIn, and credentials like former Amazon.
Hire the obsessed
In any industry, the most obsessed people treat their skillset as a craft. An art to be refining constantly by trying new paintbrushes, painting styles, subjects, etc. This applies to technology directly.
If you hire the person who aces LeetCode, you’re optimizing for someone who obsesses over landing a job. If you hire someone who lands that big tech role, you’re bringing someone on who’s obsessed with the prestige. The issue with both those types of obsessions is that it ends. There is a finish line to the obsession.
Hire someone who is always obsessed. This type of deep obsession doesn’t stop when someone gets a new job, a pay raise, or a new teammate. It tends to carry itself into all aspects of their life: obsessed with the best way to grill picanha or building a huge 50,000-plus subreddit on the side.
We’ve hired people who have just joined us for a nine-to-five job, and it never works out. You can’t justify missing time with family, putting in insane hours, showing up over weekends if you’re not passionate about the problem you’re solving.
It never ends
Hiring is also bittersweet; most people don’t stay on the team. The best advice I can give here is to always hire people who are good at heart. They know your company secrets and your biggest fires, and if you end on good terms, you may be able to work with them in the future. One of our first hires left us after a year, spent a year traveling and working at another startup, and then returned.
Over the course of my journey I’ve hired hundreds of people but I’ve also parted ways with hundreds of people. Circumstances change and people move. It may be that the company is in a different place or it may be that the person is in a different mindset. So you always have to be recruiting. The worst case that I have run into is when you put all your eggs in one basket and you have just one person who is responsible for everything, and then tomorrow they wake up and decide to leave.
If you work with people you trust and take informed bets on people, you’ll be able to assemble the most talented group of people attacking your industry. And, you’ll get to have fun while doing it!
