Umbrella? Check.

3 ways being a PM didn’t prepare me for starting a company

Paul Koullick
The Startup
Published in
4 min readFeb 21, 2019

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I’ve been a product manager for five years. In that time, I launched features, product lines, and even entire apps from inception to scale… and I totally drank the whole CEO of the product and wearer of many hats Kool-Aid. So much, that three months ago I quit to start a company and become an actual CEO (of nothing!).

Very quickly, I learned that being a PM prepares you to be a startup founder in much the same way that running track prepares you for surviving in the wilderness. Not really. Here’s a list of reasons why.

#1 user acquisition

Holy moley… this one’s first for a reason.

As a PM, I was accustomed to worrying about retention, signup conversion, NPS, and so on. But not user acquisition. The users always came. Whether it was hitting the company email list, or simply adding a tab on the dashboard, there was always a straightforward way to get people into my product. “At worst, you can just spend money on ads”, I remember thinking.

As a startup founder, nobody cares about your product. Actually, no, it’s worse than that: everyone is actively disinterested in your product.

…it’s worse than that: everyone is actively disinterested in your product.

Your customers are bombarded with so many ads and false promises every day that their croc brains will actively filter you out even before reading, let alone considering, your proposition. As a startup, you don’t have brand recognition or distribution channels.

In short, user acquisition is hard. The whole word-of-mouth / virality trope is nowhere as easy as it looks from the outside. Startups are incentivized to pretend like their companies took off on their own. The reality is that companies take off because the founders make them take off.

So how did I get over it? It’s a journey. For starters, I read Traction, which helped in the same way that a stranger telling you “Yes, this totally sucks for everyone” helps: psychologically, but only a little bit.

Lots still to learn here.

#2 coding & other actually useful skills

As a PM, I always prided myself in defining the Why and the What but never the How. I was great at it! So good in fact, that I never actually learned how to do anything useful (like coding, designing, or marketing). Specialization is for insects, right?

Wrong. As a startup, you’re too poor and too early-stage to attract great talent to do the “busy” work. All you really have is passion and work ethic, and money can’t buy that.

As a startup, you’re too poor and too early-stage to attract great talent to do the “busy” work.

Also, you can’t get away with the level of quality that larger companies have. You can’t hire a contract developer and expect them to check their own edge cases. You can’t hire a content writer and expect them to pour their heart into a blog post. You can’t hire a salesperson who’s going to follow up 8 times until the user either buys (or dies), like you’ll need. In the beginning, it has to be you.

#3 psychology

As a PM, I always had external validation. If my product wasn’t doing well, there was always a long list of confounding variables and external factors I could point to. Whether it was HIPPO, or simply company politics, I always had a psychological escape hatch.

As a founder, you have none of that. Everything wrong with your startup is your fault, and nobody cares about why. Every day, you paddle against the current of your startup turning into a shrug and a dinner party story. The only thing that can stop that is you.

Everything wrong with your startup is your fault, and nobody cares about why.

I’ve had mood swings unlike anything I’ve ever experienced in a job. To survive psychologically, I think you have to be doing it for a reason besides venture-capital-sized return. You have to actually believe in your mission. It’s the only thing that’ll pull you through.

Jokes aside, I love building Keeper. If you’re a PM considering taking the plunge, I hope this was a helpful perspective.

This story is published in The Startup, Medium’s largest entrepreneurship publication followed by +427,678 people.

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Paul Koullick
The Startup

Founder & CEO at KeeperTax.com | Previously, a happy product manager, and before that a miserable long-distance runner.