Breaking into startups: three practical examples

Advice for landing a job at a great startup

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Here’s an email we received last week from someone interested in getting a job at a hot startup:

Hi! My name is [Redacted]. I am interested in working at [Redacted] startup, and already sent a cold e-mail to the CEO. They did not respond. What do you think I am doing wrong?

My reaction is that I do not think this person did anything especially wrong but I do think there are things this person could do that would greatly increase their probability of getting hired. In this essay, I give you a bunch of practical/real examples that you can use to similarly improve your odds of getting hired at a hot startup.

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Quick disclaimer/perspective for you—I have said this before but I’ll say it again:

There is one clear path to increase your odds of being hired by a startup: try much harder than anyone else who applied. This sounds obvious. Yet practically nobody does it. That’s because trying harder than any other applicant is, by default, not easy. It’s going to take some work. But the payoff is that you get to take more control over the future of your career and life, and we think that’s worth it.

Consider the base case: most people just apply to jobs by sending their resume and cover letter.

If you really really really want the job, we suggest you try 10x harder than those people. That’s not an exaggerated number—we mean 10x. Trying only 2x harder, for example, might mean you just send a short email to the founder when you apply, letting them know that you applied and that you’re interested. That’s okay. But you can do a lot better.

So what does that look like in practice?

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Extremely practical advice for getting hired at a startup

Reminder by the way that when you’re cold emailing people to be kind. They don’t owe you a response.

Scenario 1: You stumble upon Netic (an AI revenue engine for essential services businesses). You see they recently raised $43 million from Founders Fund and others, and that they have this job posting for an “Agent Product Manager.”

What are some ideas that could help you get hired?

I would look into Netic’s customers and see they already serve a few industries: home services, pest control, roofing, and more. I would start by going on Reddit and looking into small business advice. I would go to r/SmallBusiness, a forum with hundreds of thousands of weekly visitors.

I would search for details about running a Pest Control business and read through a bunch of posts/comments and keep a document open with all of my observations. Figure out what people like and dislike about their jobs. Perhaps vibe code an agent that helps you summarize the trends. Or do it manually. I would probably quickly do both.

Next, I would go to a platform like OpenMart, a database of local/small businesses, and generate a list of pest control businesses in my area. I would then call up several of the businesses and see if they would be open to a quick user interview, to learn more about how they run their businesses today. I would even consider paying them an amount of money if they would let me come shadow them for a day. Again, I’d add all of my learnings to my document. This doesn’t have to take a long time. Could be just 15 minutes.

I would then turn my list of insights into a presentation (perhaps using something like Gamma or just Google Docs and Slides is fine). In my presentation, I would try to generate ideas for new agents Netic could consider building, and make the case for why they would solve important problems for the sample customers you’ve spoken with. I would then record a Loom video of myself going over the presentation. And then I would send a simple (human!) cold email to Melisa Tokmak, the founder of Netic. I would figure out what to email after watching a video of Melisa speaking, but in general I would keep it concise and human. I would follow this guide:

The guide to getting a job with cold email

I think the above strategy is probably already something they rarely see. But you can try harder. Let me know what you come up with :).

Scenario 2: You see Next Play’s recent newsletter that Bryant Chou, the former founder/CTO of Webflow (multi-billion dollar startup) is starting a new stealth company, and is looking for a chief of staff.

What are some ideas that could help you get hired?

Well you’re in a bit of a tricky situation. All you know is that he’s hiring a Chief of Staff, but you don’t know specifically what type of company he is building.

The first thing I would do is do some research on my own. I Googled Bryant’s name and found his personal website. He has two old essays (one about wanting to start a cognitive bias newsletter and one more general advice about building startups). He also has a few interviews just on the internet that you could read here and here.

Now that you’ve done that, you have a few options.

One path is to read the comments on his Linkedin announcement, and pay attention to who is commenting. It looks like Eric Bahn knows what Bryant is up to, as he said he’s investing in this next venture.

Eric is a pretty prolific investor who regularly posts on Linkedin. I think chances are high that if you’re able to impress him via cold email, he would respond, and he could then potentially introduce you to Bryant, or some other company in his portfolio that is hiring. So what if you spent 30 minutes figuring out how to prove to Eric that you have high agency and can get things done?

One simple idea: you could look up that Eric helps run something called Hustle Fund. You could go on Hustle Fund’s website and find their portfolio. You’d see that they list some of the companies they’ve invested in in an Airtable.

Airtable is great and all, but I think this resource could be better and more useful to their audience:

• You could use Lovable or Claude Code to vibe code a little mini game that allowed a job-seeker to explore the Hustle Fund Portfolio. Imagine a 2d map where someone could walk their character around, kinda like Pokemon, and can learn about companies that are hiring in the portfolio.

• You could use Claude Code to scrape the jobs pages of every company in the portfolio, and then do an analysis on the types of people/roles/etc. they are hiring for, and even come up with ideas as to how they could help their portfolio companies fill their roles faster.

• You could propose a marketing strategy where you run email interviews with hiring managers in the portfolio as a way to boost brand visibility for the startups and also for the fund.

You could do any of those things, and then send an email or LinkedIn message to Eric. And in the message say you’re looking for a Chief of Staff position, and that you particularly admire Bryant and would love to learn more about what he’s up to.

You could even draft a forward-able message to make the introduction easier to facilitate. The message could look something like this:

My name is X. I am really interested in learning more about your new company. I’ve long-admired Webflow, and am curious what you’re doing next. I am also curious to learn more about the cognitive bias experiment - where did that go?

Quickly on me:

• Impressive thing I’ve done one

• Impressive thing I’ve done two

• Impressive thing I’ve done three

Also here’s a Loom of me talking over this so you know I’m real!

My phone is X. Would look forward to speaking soon.

I think that’s likely to get a response. And if it’s not, I’d consider emailing this sort of thing to other investors of Bryant’s previous companies or other people who engaged in the post.

If none of that goes well, you could of course just email Bryant directly. He may not respond - because not everyone is going to respond - but it’s worth a shot. You could repeat this sort of strategy with several other companies, and I’d bet that within 5-10 of them you’d find someone interested in hiring you.

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Scenario 3: You see that David Litwak from Maxwell Social is building a social club and creative studio in NYC, and that he’s looking for salespeople.

What are some ideas that could help you get hired?

I would start by reading about David and Maxwell Social.

I would read all the articles I could find online. I would look at everyone who works at the company, and see what they are posting about, and what types of events they are running today.

The LinkedIn post did not actually contain a job description, but I would find it by Googling around.

So it looks like a big part of being a good salesperson at the company is being able to generate revenue, ideally using a proactive strategy to help find people/companies who want to book events. How could you prove your ability to do that well?

I would cold email 10 VC funds in NYC and ask them how they do community today. Do they do in person events? I would propose hosting a roundtable event at Maxwell Social, and also tell them you’ll help facilitate the crowd of e.g. future founders. I would then email the CEO of Maxwell and tell him you’re about to close your first deal and you’d like to find a way to work with them on the sales team.

I think that would be a hard email to not respond to.

I would also think about more creative types of events that you could host at Maxwell. For example, I would look at Youtubers and TikTokers in NYC and see if they’d like to host small events with their subscribers. I would see if any musicians wanted to host a music video in the space. I would look at up and coming fashion brands in NYC out of fashion school and see if they would like to do a small mini fashion show in the space. I would look up events happening in NYC on Luma or Partiful, and see which brands are running public events. I would get in touch with those brands and see if they were interested in using the space.

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Now it’s your turn. I want you to try this technique out on two startups you are interested in working at. Not sure where to look? Here are some suggestions:

• 33 fast-growing startups that are currently hiring

• 37 companies that recently raised $10m–$50m and hiring

Let me know how it goes. Email: hi@nextplay.so.

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Was this helpful? Happy to do more of these. My email is hi@nextplay.so if you have any feedback or requests.