Yes, the World Wants Your Startup To Fail

No, you can’t do anything about it

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Yesterday, I had coffee with a friend who is the founder of a pretty early startup. Her company is doing well, but still has a ways to go. It’s promising, a little bit past minimum viable, but just short of traction.

As we discussed her plans and progress and problems, it started to become obvious that she was more than a little worked up.

When she started talking about a prospective customer deal that was now some two months between handshake and signed contract, she exploded, angrily taking out the prospective customer, their understanding of her tech, and even their understanding of their own business model.

Then the frustration of a year’s worth of trying to get an inspired business idea off the ground bubbled over into a litany of speculation, accusation, and conspiracy. Everyone was against her.

Been there.

Negative energy is the wrong kind of energy

But while being the underdog can be a huge source of motivation, the fact that you’re never on a level playing field can wear on you over time. Suddenly, that chip on your shoulder turns into a boulder, and moxie and pluck quickly melt into frustration and anger.

Negative energy can be a good thing, right up until the moment it isn’t.

Then it’s regret. Or a setback. Or a lawsuit.

Yes, people are going to dismiss you

OK, I’m being a little over the top there.

But not too far over the top. Without resorting to hyperbole, I can tell you that everyone will always be looking for your next thing — your next sale, your next version, your next milestone, your next raise, your next accomplishment. This never ends.

To realize this is to prepare for it and to use it to your advantage. Let them underestimate, go ahead and underpromise, then overdeliver.

Yes, people are going to take advantage of you

The hell you do.

But every customer and partner and investor will expect this. It might be that you approached them because they were close by and in your network and so they expect a friends and family price. Or maybe they’re big, you’re small, and even though they need what you’re offering, they can stand the pain of passing on you, while you can’t afford not to take their money.

If you’re in the business of giving stuff away, you’re an idiot. And yes, they kind of think you’re an idiot.

Hold your ground. Make any discount contingent on payment in full the moment you show value, or let them know they can walk away with no hurt feelings.

Yes, other people are going to get breaks for the wrong reasons

Startup is probably the closest thing we have to a true meritocracy, but it still has a ways to go. When you think about all the money and opportunity and recognition flowing through not just Silicon Valley, but around startup hubs all over the country, and how much of it goes into bad ideas fronted by charming people with really good connections, startup can seem like a snake oil show.

Look, if the world were fair, it wouldn’t need what you’re doing. You can dwell on that unfairness or you can make it part of your plan. Hell, budget in another 10% just because WeWork messed a lot of things up for a lot of people.

No, people aren’t going to see the value of your product

While I believe people are generally both good and smart, I also believe that customers, partners, and investors are naturally skeptical and resistant to change. Those things are hugely incongruent and the negatives will always skew the positives.

People are going to poke holes in the value of your product, the company you’ve constructed to sell it, and the means by which the product gets into their hands. Even when people do understand and value your product, the first time it does something wrong they will come after your piece of shit product and your company full of morons. Probably on social media too.

Understand why this happens and learn from it. Respond with kindness and maturity or don’t respond at all.

No, people aren’t going to give you points for trying

You get no breaks for that. In fact, you usually get resentment for it, because most of the people you’re selling to think you get all that plus you get to make your own hours and you have no boss.

No, people don’t want a better solution

Some people love the freaking status quo.

If you’ve ever tried something new and then slapped your forehead and shouted “Why didn’t I do this sooner?” you need to understand that there are a lot of people out there who have never had that moment. They just don’t want it.

It’s maddening when you put a solution in front of someone and show them a quantified and qualified benefit — savings of time or money, an increase in efficiency, a marked improvement in something they depend on to do what they do — and they still don’t want it. It’s the most maddening thing ever.

The only way I’ve learned to counter this is to empathize and ask them what I need to do to make it crazy easy for them to give the solution a try, including doing it for them until they lose that fear of change. And that still only works about half the time.

Don’t get mad at the maddening

Don’t let that happen. Be the business assassin, and get revenge quietly with your own success and satisfaction.

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I’m a multi-exit, multi-failure entrepreneur. Building Precision Fermentation & Teaching Startup. Sold Automated Insights & ExitEvent. More at

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