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Confronting imposter syndrome as a startup founder

by Josh Pigford. Last updated on November 27, 2023

Yesterday morning, my alarm went off at 5:45am and I proceeded to break my cardinal rule of checking email immediately. The first email I had was from someone letting me know of negative comments on Hacker News about Baremetrics. I went and tracked down the thread they were referring to and proceed to read half a dozen comments from people who weren’t fans of us.

I then spent the next hour getting kids to the bus and me out the door to the gym, but the entire time my mind was distracted by those comments. It was just eating away at me and it got me thinking about something I’ve been feeling for the past 12–18 months.

Something that a lot of founders feel, but rarely talk about: imposter syndrome. It’s that little voice in the back of your mind that tells you, despite any clear successes you’ve had, that you’re not good enough.

Honestly, it feels a little whiney to even talk about it. “Awww poor little Joshy and his little million dollar business, it must be sooo hard. Boohoo.” But alas, here we are.

A mental game

If I’ve learned anything over the past 15 years of business it’s that it’s mostly a mental game. Yes, there are an infinite number of product, team and company decisions to make, but the more your business grows, the more the role of the founder/CEO changes to a mental game.

What’s been interesting to me is that the mental pressure has actually become greater as our business has grown. “Making more money” has not equated to “having less stress” or even “feeling more successful”…it’s equated to the opposite, actually.

The suggestion is generally to “fake it ‘til you make it” but when have you “made it”? I’ve been trying to wrap my head around this a lot lately, primarily by defining what “success” means to me, but I’m not fully there yet.

Most of this is self-inflicted. The large majority of customers and onlookers are supportive. But that doesn’t make the negative stuff sting any less.

I wish I had some superhuman level of drive and focus that allowed me to not internalize negative feedback (however off-base it is), but that’s a skill I’m still working on.

What to do about it?

On a practical level, what does one actually do about imposter syndrome? Clearly I haven’t figured it all out yet, but I think there are a few things you can do to help mitigate the feeling.


One of the biggest helps has been having a small community of other founders that I can talk openly about this stuff with. Being a founder is a lonely place and I think simply knowing you aren’t the only one that feels that is really helpful.

Get out of the echo chamber

I wrote an entire article about this a few weeks ago. When you’re neck-deep in startup culture, you can’t help but compare yourself to other companies and your brain is constantly chewing on all the things you should be improving and fixing about your company. Take a step out of that regularly to get better perspective.

Talk to customers

The more your company grows, the easier it is to get caught up in “running the company”, which many times means you don’t hear directly from customers all that often. When you step out of having regular customer interactions, you inadvertently filter out most of the positive interactions and are just left with the fires you need to put out.

Spend time reaching out to customers for no other reason but to see how things are going and see how you can help. You’ll be surprised at how encouraging that exercise is.

Calling it what it is

Most days I feel pretty confident in my ability to not run the ship in to the ground. Heck, a lot of days I’m probably overly confident. But every now and then, like when someone questions our success, or there’s a whole thread of negative comments on Hacker News, or our competitors are taking advantage of scaling issues from two years ago to use as marketing collateral…those days are tough.

And I think calling the tough days for what they are is much more therapeutic and healthy than brushing them under the rug and faking it until you do or don’t make it.

If you ever need to vent or want to talk about any of this with someone, always feel free to reach out at or @Shpigford.

Josh Pigford

Josh is most famous as the founder of Baremetrics. However, long before Baremetrics and until today, Josh has been a maker, builder, and entrepreneur. His career set off in 2003 building a pair of link directories, ReallyDumbStuff and ReallyFunArcade. Before he sold those for profits, he had already started his next set of projects. As a design major, he began consulting on web design projects. That company eventually morphed into Sabotage Media, which has been the shell company for many of his projects since. Some of his biggest projects before Baremetrics were TrackThePack, Deck Foundry, PopSurvey, and Temper. The pain points he experienced as PopSurvey and Temper took off were the reason he created Baremetrics. Currently, he's dedicated to Maybe, the OS for your personal finances.