The Hardest Thing for Founders To Be Comfortable With

Being comfortable being cringe is actually a secret weapon for founders.

Why?

It communicates that you have confidence in the thing you’re building (and selling). You’re all in on it. You believe it can make a difference.

But it’s hard to reach that comfort especially if you’ve never done sales or marketing before.

For many founders it’s the hardest part of building and growing a startup.

It’s natural. I had to overcome it too.

Let me show you how!

Founders & Cringeyness

What Is Cringe?

You might think about being cringe as something like being awkward.

There’s a good (short) book by Adam Kotsko about how the predominant driver in pop culture humor morphed in the early 2000’s from irony to awkwardness. The switch is best explained as the difference between the mid 90’s, Larry-David-written Seinfeldian humor and later-career Larry in Curb Your Enthusiasm.

They’re not the same.

You know this because of how each makes you feel.

Awkwardness gives you a general feeling of discomfort about being present for something, whereas witnessing cringe gives you a more personal and specific I’m-embarrassed-for-you feeling.

So what is cringe?

In a world where everyone keeps their options open in everything from who to date to who to invest in, cringe is refreshingly single-minded.

It’s a willingness to go all-in on something you believe in, no matter how it makes you look.

For founders being cringe is shamelessly shilling your product to anyone who might get value from it. Not because you’re trying to trick them into paying you, but because you genuinely believe you can help them.

Cringe does whatever it takes.

It’s me posting a fourth founder bio thread on X in a little over a week because the first three added $2,000 in MRR to Megaphone:

Even when your friends troll you:

Overcoming the Fear of Cringeyness

Understanding cringe is one thing, but how do you overcome the fear of looking cringey yourself?

I notice this in a lot of founders going after new markets — not just first-time founders.

IMO there are four ways to handle it:

Start Noticing Cringe

Cringe is everywhere. The world runs on it.

Once you internalize this by keeping a conscious eye out for it in the ways people behave and companies sell things, you start getting more comfortable with it.

You can turn it into a system — “company x” did a cringe thing that a ton of people would have seen, and I admire their product, so I can do something equally cringe.

I’ve never done this, but you could even start writing down the cringey things you see online and IRL somewhere.

Ironically, doing that is actually pretty cringe too so maybe it’ll help you get over it faster?

Consider it a Necessary Evil

You’re the founder, so eventually you might have a marketing team that handles the cringeyness for you.

But to get something off the ground you have to lead the way.

No one believes in your startup more than you do. You need to will it into existence.

You don’t need to like being cringe, but being willing to do it will help.

Make It Fun & Lean Into It

If you’ve been reading this and thinking “what’s wrong with being cringe?” then this is for you.

One benefit is that fully committing makes you impervious to criticism. If you’re always cringe then you won’t have to deal with backlash for making a cringey post.

But being always cringe isn’t always the right strategy.

Experiment with the level of cringeyness that works for your ICP. What gets them most excited about the product?

It’s (thankfully) not true that more cringe = more success in every market, but in some markets it is true. Knowing whether this is true for you comes down to how well you understand the way your ICP perceives your brand.

Get Reps & Accept

My Latin teacher used to say “repetitio est mater studiorum” — aka repetition is the mother of all learning.

And it’s true. Something you do more often lets you feel more ok with it, since bad things don’t happen as a result of it.

If none of the above are working then my advice is to simply persist.

Lean into it where you can, and over time you may find you gradually become more comfortable.

A Last Resort

If you’re really uncomfortable with all of it, get a cofounder who isn’t.

It’s ok to not be the salesperson.

Divide and conquer.

💡