The hardest part of starting a career in tech – of starting any career, really – is getting your foot in the door.
There is no one right way to find your first internship, but I’ve found that the baseline path – sending in applications to every internship job posting that you can find – is pretty ineffective. Even if you have a near-perfect GPA at a top school, it’s really difficult to stand out from the stack of applications, particularly with no experience. Despite having product management internships on my resume at VC-backed startups, I still can’t even get an interview when I apply to PM intern job postings as just a 1-of-n cold application. When I started looking for an internship with basically a blank resume, I didn’t stand a chance. Campus career centers can’t really do much to help you. By definition, they give mainstream advice, and you’ll never stand out if you follow the same advice as everyone else.
The first step to finding your first internship is figuring out what you want to do. For me, that meant some combination of talking to my friends going into tech, and consuming every publicly-available resource on startups and roles within startups that I could find. I probably spent at least six hours per day for five months learning about startups before I even tried working at one. I spent a lot of time reading books and newsletters, listening to podcasts, and talking to people who worked in or were interested in tech. A five month exploration period is probably not necessary, you can move a lot faster than my timeline before you start sending cold emails. I became really, really interested in startups before I realized that I wanted to spend my life working on them. Plus I was on a gap year, so I had nearly-endless time to explore my interest – that won’t be the case for everyone, but it helps to build a base of relevant knowledge. Once you’ve learned about the ecosystem and familiarized yourself with some of the frameworks, lingo, and ethos of the startup world, you might be a lot more hirable than you think.
If you’re spending a ton of time reading and thinking about startups, you’re going to come across a whole bunch of startups that you find cool. Start making a list of startups you might want to join and people you want to work with. One really cool thing about the internet is that, when you admire someone, you can just…reach out to them. Sometimes they answer! Sometimes they even hire you! If you find someone you want to work with, send them a well-written, well-researched, and concise email. You’ll get a lot more responses than you think.
When I email founders about potential internships, I get about a 40% response rate. And that rate was the same before I had any relevant experience. The first summer I started a cold email campaign, back when I had no idea what I was doing, I sent 79 emails to founders of cool VC-backed startups. I wound up receiving 30 responses, which ranged from quick rejections to incredible words of encouragement to interview invitations. Some of those responses came within minutes, some founders took weeks to get back to me. Even among startups that ultimately offered me an internship, there’s a wide range of response times – don’t read too much into it. Of the 30 responses, I met with 11 of those startups over the course of the spring, and received one offer, from a series A startup called Convictional (they’ve since raised a series B, have an incredible team and a ton of momentum, and still respect a good cold email).
One other note on my first opportunity with a startup: I had a little line on my resume about the long-form blog I was occasionally writing on Substack. I wrote 10,000 words across three posts, and it gave a little insight into how my brain works, but I didn’t really expect anyone to actually read it. I just wrote it for fun. Writing on the internet is one example of a bet with asymmetric upside, one that is often worth making. Convictional’s founder and CEO took the time to go read my writing (which still amazes me, as a random 19-year old with no experience who sent him a cold email) and was impressed enough that by the time we hopped on Zoom to meet, he was ready to hire me. We crafted a role as a product intern, they created an incredible amount of scope and autonomy for my first internship (in a way that only an early-stage startup can), and I had an awesome summer and became shockingly hirable going into my sophomore year. Beyond the potential benefits to your career trajectory, working at a startup can just be a ton of fun. I can’t possibly recommend it enough.
I’ve helped a few friends with their own cold email campaigns, and the process isn’t always so straightforward. Sometimes you have to A/B test email templates before striking the right chord and getting positive responses. While I use a template, I definitely customize most of the emails I send. Parts of the email where I describe myself are pretty universal, but it helps to show a unique understanding, interest, and passion for the founder’s startup. Explain why you’re interested in their market, traction, and/or product. If you identify with something they said in a podcast or have thoughts on a blog post they wrote, use those insights to differentiate your email in a crowded inbox. More than focusing on what you’ve done or the skills you have, focus specifically on the ways that you can help them this summer. Startups constantly have more problems than they have people to address these problems. The best way to convey your value is to be explicit about the ways you’ll make everyone’s lives easier.
The quality of the writing and the clarity of your message are really important. Founders are really busy, and they don’t want to waste time reading a crappy email from a college kid. But they’re also in “hiring mode” 100% of the time, and the one really cool thing about the startup world is that people are constantly looking for undiscovered young people with high potential. If you might be one of those people, and you can communicate that in email form, you’ll get access to opportunities that you never could have imagined. Incredible founders are not out of reach for talented, ambitious, hard-working young people.
One important note is that you don’t need to email founders of startups who have already publicly posted an intern role. Actually, I think you’re better off reaching out to startups that aren’t looking for interns in your desired role. If you apply to an established program, a well-written cold email can help you stand out from the crowd. But if you apply to a program that doesn’t even exist, you won’t be 1-of-n candidates, you’ll be the candidate. Of my three internship searches, I’ve still never been offered a role that actually exists – if you impress people, they’ll create a role for you. That way, your summer can most closely align with your skill set and unique value-add, and align with the things you’re looking to learn during your internship.
Recap: Tips for sending cold emails to startups
- Communicate how you can add value to their startup at this stage. Nobody wants to babysit an intern for three months. Everyone wants a talented person to take stuff off their plate. Always strive to be the latter. I suppose that’s career advice, too.
- Explain why you’re interested in their startup, specifically. Think product, market, team, traction, etc.
- Keep it concise and easy to read. If you’re writing long paragraphs, consider whether you can turn them into bullet points. I like to write two or three short paragraphs, one longer paragraph about my background and my interest in startups, and 5-6 bullet points about things I can help with during my internship.
- Go for it. The worst thing they will do is delete your email. Cold emails are the ultimate embodiment of an action with asymmetric upside. The only downside is that you might waste some time writing the email. The upside can be life-changing. Email someone who seems like they would never answer, they might surprise you. Always be ambitious.
- If you’re passionate about something, let that shine through in your email, but keep your responses short, simple, and sweet
If you’re interested in going deeper on tactical advice, or if you start sending out your own cold emails, I would love to hear from you at casey.kline@dormroomfund.com. I really nerd out about this stuff and I love meeting other people who get passionate about both startups and cold outreach.
Written by DRF content associate Casey Kline. More updates on our Twitter, Medium, and newsletter. Founders, apply for an investment from us. 🚀