February 28, 2011
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When you want to quit because it’s just not worth it

Are you crying in the shower because you can’t handle it anymore? Beyond Impostor Syndrome: Complete melt-down? Well, at least you’re in good company.
T-Shirt that says "I never finish anyth"

I’ve been there too. It sucks.

Most startups fail “only” because the founders stop working on them, and often it’s because it’s emotionally draining. I don’t care who you are or how strong your ego is, you will have these moments—perhaps a continuous stream of moments—when you can’t take it anymore.

I cannot remember the number of times I was so overwhelmed at Smart Bear that I almost threw in the towel. Close the bank accounts, close the doors, turn off the website, bounce the email, and just…


Sounds dramatic, but it’s no exaggeration. You’ll hit these walls too. I know you will because this is what people admit in little rooms with other people who truly understand and won’t name them publicly, and also there’s a steady stream of people saying it out loud on Twitter, many times per day.

Maybe a little commiseration will help you get through it.

You expect these moments to happen at the beginning of startup life—when you’re least confident, have the worst product, and the least knowledge about your customers and the market. Paul Graham and Trevor Blackwell captured it pretty well:

The pain is not limited to the beginning of the venture. It’s still there years later, despite real revenue, profitability, customers arriving every day, and a great team.

Since that is not obvious, I’d like to share a personal story.

Four years into Smart Bear I had several employees getting paid decently (which at a bootstrapped startup is hard to do!), a product that people were buying, and we were doing around a-million-a-year. Life was good!

I was negotiating my first true “Enterprise sale.” This was going to be our biggest order to date—something like $200,000. (Yes, one-time revenue. It was a simpler time.) Actually “negotiating” is the wrong word because I don’t believe in price negotiation, even with enterprise sales (an area that most people claim must include automatic discounting.)

The person with whom I was negotiating wasn’t the end user, nor the boss, nor the boss’s boss, nor anyone in that chain of command. See, big companies have entire departments devoted to dealing with vendors like you and me, and when it comes to negotiating, these departments harbor terrorists with titles like “Procurement Manager” or “Strategic Sourcing Manager.”

I say “terrorists” because they use fear tactics to get their way, yet they have no power other than fear. Imagine the worst stereotype of a salesman, except instead of selling you something, their job is beat a discount out of you.

Now to be fair, many vendors do take advantage of large companies—overcharging (because “They can afford it!”), or promising one thing to the users and sneaking something else into the invoice.

But mostly it’s because of the traditional enterprise sales dance, reminiscent of the lumbering mating dance of the great blue whale. The vendor asks for too much money; the client is astonished at the price. Both calmly explain that this is a deal-breaker. Then the vendor capitulates 30% but only if the client signs a three year maintenance contract (which they wanted anyway). The deal is struck.

This tradition continues because of perverse, wasteful incentives. The vendor’s salesman likes this because sometimes she gets away with a high price which pads her commission check. The Procurement Manager likes this because he can show his superiors how much money he’s “saved” the company.

So big companies need a Defender of Evil Vendors, I get that. But that’s not enough for these guys; it feels to me like an attack, not a parry.

This is how the conversation went:

PM: What kind of discount are you offering?
Me: We don’t discount; instead we put our pricing on our website so there’s no misunderstanding.
PM: Well I’m going to need some kind of discount. How about 30%?
Me: As it says on our website, we don’t discount.
PM: But I’m buying 400 seats!
Me: Yes, and we already provide a nice discount for bulk orders, which is already included on the invoice and documented on the website.
PM: You don’t understand, I always get a discount. I’ve done business with 47 other vendors and all of them give me at least 20% off.
Me: There’s always a first!

So far it’s actually OK—I’m the one refusing to plod through the mating ceremony, wanting to skip right to the wedding night. I expect push-back.

Here’s where it gets nasty. I remember sitting there on the phone getting lambasted for my intolerable ignorance about the Way It Works. I was told, and I quote, “You have no business selling anything to anyone.” My obstinate ignorance is a deal-breaker for the entire sale because of what it implies about my company in general—after all if I don’t even understand the purchasing process there’s no chance in hell my software’s going to work! Furthermore, despite my ignorance, I’m unwilling to listen to the rules, unwilling to learn, which means there’s no hope for me.

I’ll never forget how this ended:

PM: OK that’s it, you give me no choice. I absolutely cannot approve this deal, and furthermore I’m recommending that we never work with your company in any capacity. At this point, even if you gave me a discount I would still reject it.

Here’s where I’m supposed to unleash my intellectual fortitude. I won’t capitulate, will I? I won’t let this guy insult and bully me, will I? C’mon, I’m the strong-willed confident entrepreneur with the stoic well-argued voice of reason, whereas he’s the sleezeball with the tedious day-job—surely I’ll laugh as his words roll off me like water off an oiled duck’s back.

Just the opposite. I felt like throwing up. He’s right, who do I think I am? I’m a baby geek playing in the adult’s house and I don’t know what the hell I’m doing. I have these naïve ideas about how the world should work and how people should treat one another, and it’s all just incredibly silly and ignorant. And it shows. And now this guy is going back to those other folks at the company whom I actually like, and worked hard to earn their trust, as they laugh together over can-you-believe-how-dumb-he-is and we-can’t-possibly-do-business-with-them.

It’s over. They’ve seen through me. It’s just a matter of time before others do too. That’s the end of deals like this.

Why am I doing this anyway? This is supposed to be fun and fulfilling but at this moment as we say in Texas I feel like ten tons of shit in a two-ton bag. What I like is writing code—why am I even trying to play this sales game? Why not just go get a job where I only worry about whether or not I can write code—because I sure as hell can do that—and let the natural salesmen do all this crap?

Is the money worth it? What money, we’re still bootstrapping and I still don’t get a regular salary. Is the promise of money worth it? Worth these feelings of inadequacy?

After days (yep, days) of fretting like this, it converted from despair to anger. Who the hell is this guy? Some asshole who isn’t good enough with money to be an accountant, not even slimy enough to sell cars, this guy whose only skill is to be a jerk, some guy who has never had to make payroll or take a risk or put himself out there, this schmuck is going to tell me I’m the one who isn’t good enough, I’m the one who has no business selling software?

Worst of all, I’m letting him make me feel like a pile of shit!

Well if you’re waiting for the big moment where intellectual reasoning finally defeats weak, irrational emotions, I’m sorry to disappoint you, because that moment never came. I know it’s dumb and illogical, but there it is. It’s trivial and baseless but I still carry that experience in a corner of my thoughts. That’s how emotions work.

By the way, this guy turned out to be totally full of shit. He had, in fact, no power to stop the deal. When I finally got my main buying contact from that company on a conference call with the PM, the conversation was this short, and as close to word-for-word as I can recall:

My Guy: So, what’s holding up procurement’s approval?
PM: Nothing, just some paperwork, we’ll have it done by Friday.

All of that angst for nothing. Son of a bitch!

Years later I was on-site at this company and I finally met this guy face to face.

I still felt small.

Want to say I’m weak? Or he’s strong?

Who cares, the point is: Getting through this slog of a thing that’s a startup—or anything difficult and worthwhile—doesn’t require that you’re always confident or stoic or smart or right or wise. You don’t need to match the emotional stability you see from the big bloggers. (Which is mostly a façade anyway.)

It’s not even about “overcoming.” Maybe you don’t overcome, you just get through.

It’s about sticking through the tough parts, whatever your foibles and weaknesses.

Living through it, not beating it. I never have, to this day, “beaten” that PM, not emotionally, not if I’m being truly honest.

Welcome to your crucible.

I’m not saying tenacity is all it takes. Just that without it, you’ll stop.

It’s so easy to stop.

There’s so many reasons to stop.

And that—stopping—is how most little startups actually fail.

P.S. Since writing this article in 2011, I was able to avoid burn-out and tame these thoughts with a framework that I detail in this article from 2022.

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