Alex Kouts | Getting Hired at a Startup (Episode 455)

Alex Kouts | Getting Hired at a Startup (Episode 455)

Alex Kouts | Getting Hired at a Startup (Episode 455)

Alex Kouts (@akouts) returns to The Art of Charm to talk about how to get hired at a startup (and if the startup life might — or might not — be a good fit for you).

The Cheat Sheet:

  • What is a startup?
  • How does a startup find a sustainable product/market fit?
  • What kind of person chooses the potentially unstable startup life over the safer options their parents keep nagging them to consider?
  • The startup life is not a get rich quick scheme — if you choose it, you’ll probably work harder than you ever have before (but with the potential rewards to match).
  • Why aren’t you getting any startup job offers even though you’ve submitted your resume dozens — or hundreds — of times online?
  • And so much more…


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Episode 455 of The Art of Charm marks Alex Kouts’ third visit to the show. In the past, he’s taught us how to negotiate, and he’s given us pointers for how to speak in public. This time around, he’s here to teach us how to get hired at a startup. If what they say is true — that the third time’s a charm — this should be Alex’s most charming visit yet!

We’ll talk about what startups are, why they’re unique, why their atmosphere of high ambiguity suits certain people (and doesn’t suit most of us), how to get into certain roles (and what those roles might be), some stories of successful startup hires that are highly unusual, and how to get meetings, ask for meetings, and suggest meeting times. Even if you’re not thinking about getting hired at a tech startup, you should find some interesting takeaways from this episode.

More About This Show

All startups are young companies, but not all young companies are startups. In fact, it’s probably easier for the layman to define what a startup isn’t (e.g., you and your brother-in-law consulting from a basement “office”) than what a startup is. Here’s Alex Kouts’ take:

“It’s a really tough thing to define, right? It’s kind of like, ‘What is a star, really?’ Startups are basically very young companies. Things are very mushy. There’s a lot of things going on at any point, but in reality, they haven’t really figured out what they want to be when they grow up. So it’s kind of a combination of a lot of people that may or may not have a business plan. And with some type of idea for a product and a user, although they may not be fleshed out really, yet, but they’re in the early stages where things are moving very quickly and breaking very fast.”

Alex says there are a couple of features that help differentiate startups from the big companies they aspire to be:

  1. Limited resources: At a big company, there are probably multiple departments — like personnel, sales, marketing — that have their own staff and budget allocations. A startup may consist of two or three people who run everything from one room — and their roles probably intertwine rather than being dedicated to one particular task. The hours are long. The rewards are probably few.
  2. An environment of high ambiguity: As a startup, you don’t know what your product or service will bloom into when (if) it “grows up.” You’re still feeling out your product/market fit, which is a term explained by investor Marc Andreessen as, “being in a good market with a product that can satisfy that market.” A big company has already found its footing and probably has a good idea how to keep itself sustainable through its market’s fluctuations.

The startup with a chance at succeeding probably has some kind of compass in place that’s guiding it toward a decent product/market fit. Either the startup’s founders are trying to create something unique that people want but aren’t getting (like, say, cracking the secret to eternal life), or they’re trying to do a job in an existing niche better than anyone else can do it (as the Facebook model of a social network quickly prevailed over the MySpace model that once seemed unstoppable).

Another element of the startup that separates it from bigger companies, says Alex, is that “every situation in a startup demands a very high level of ownership for the things that need to happen.”

“In a corporation,” he explains, “if I don’t do my job, there’s a likelihood that somebody else may do it. Which means that there’s some element of it that I don’t really own because eventually someone will do this or it will get done. In a startup, if a specific task needs to be done, you’ve got to do it, or no one’s going to do it, because there’s nobody else.”

But this is also one of the things that might be appealing to someone who chooses the potentially unstable startup route over working for a tried-and-true company that’s been around for generations. Sure, the pay may not be great to start with, and the risk of failure may mean you’re looking for a new job around this time next year. But if you’re passionate enough to take ownership over your role in a startup, it could very well be your calling.

Geography can also play a big part in a startup’s culture and how well someone who aspires to work there might fit into it. Even within the same country, it’s surprising how all the little variables between one place and the next can add up. The way things are done, the topics that are discussed, the political climate, the weather, and the overall pace can make the same city Heaven for some and Hell for others. A person who could thrive in the environment of a Silicon Valley startup loft may not do as well in VaynerMedia’s Chattanooga office (and vice versa).

“Everybody [in Silicon Valley] is a zealot,” says Alex. “They really believe that what they’re doing is going to change the world. We’ve been eating bananas like monsters for the past 250 years; now, there’s a better way to do it. One of the best pages ever on Amazon is this product that slices bananas. And if you look at the reviews of it, that type of tone is the best possible way to describe what it feels like to be in a startup…”

“People are like, ‘Oh, my God! I don’t know what I’ve been doing with my life until this thing came around! It’s literally changed everything!’ There’s the world before and after the banana slicer!” (As an aside, the BIC pen reviews are comparably hilarious.)

Humor notwithstanding, the ideal startup candidate has to be passionate about what it is they’re working with. The startup life is not a get rich quick scheme. “There were months and months and months on hand where I [would] work a hundred hours a week,” says Alex. “I didn’t take a vacation for three-and-a-half years. And I mean, like, working on weekends, every day…because that’s what it took to get the company to where it needed to be. And unless you have that type of dedication, and unless that’s something you want, it’s going to be a tough place to be. But it’s rewarding on the other side of it because you do really get to build something and see it evolve every day as a direct result of the things you’ve done — which is amazing and hard to find.”

If we haven’t yet scared you away from pursuing a path in the world of startups, listen to this episode of The Art of Charm in its entirety to learn more about what you can expect on the bumpy road ahead, why networking and connecting with others is 80% more likely to get you a job than submitting resumes online, how to use LinkedIn messaging to get real life meetings with people who are hiring, and many more strategies that will help you get hired at a startup!


Resources from this episode:

Alex Kouts’ website
Alex Kouts | The Art of Negotiating (Episode 326)
Alex Kouts | The Art of Public Speaking (Episode 393)
Alex’s classes with General Assembly
The Art of Charm bootcamps

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