Is It Time to Quit Your Startup? Ask Yourself These 3 Questions First

The day you decide to start your business, the future looks bright, clear, and hopeful. Every day after that, there are a million reasons to turn back: Your inbox will be stuffed with investor rejection letters. Maybe you’ll raise the money, but you’ll burn through it faster than you can say convertible note. Somehow, you will always be running out of time or motivation or both.

Roadblocks are one thing. Titanic-sinking icebergs are another. As a founder, you have to decide which is which—and whether to stay the course or abandon ship.

First, ask yourself these three questions:

Do People Care About The Problem You’re Solving?

You don’t need expensive Facebook ads to tell you this. You don’t even need a full-fledged product. In fact, I answered this question with no budget at all: Every day, I would sit in front of Twitter, stalking anyone who made the slightest mention of roommate trouble in New York City. Then, I’d gently direct them to a Tumblr page with apartment listings and a Google Forms application tacked on the end.

It wasn’t pretty, but it worked. During the toughest times of my business, when I owed money to everyone and their mother, when I couldn’t get an investor for nine straight months, this was the truth that kept me going: There were, at the time, 20,000 users who had a problem with shared housing. There were 20,000 people counting on me to help them solve it.  

Be honest with yourself: Are you gaining traction? More importantly, are you gaining traction without paying for it? If you are, good. Let this be your motivation to press on—because even if nothing else seems to be going right in your business, you know, at the very least, you’re solving a problem that’s important to someone.

And if you can’t get users? If organic demand is non-existent and even paid traffic isn’t converting? It’s time to revisit the lifeblood of your business: Find a new problem that’s

1. One you struggle with.
2. One people around you struggle with.
3. One that impacts the world.

Does Your Product Solve That Problem?

Or as investor Marc Andreessen puts it: Do you have “a product that can satisfy that market?” Satisfy is the key here; we’re not talking about email subscribers or app downloads. There’s only one real benchmark of success: Are you getting your users from Point A to the finish line?

This, my friends, is product-market fit—and you know it’s happening when users can’t wait to tell you their success story. That’s why my team and I maintain #success Slack channel, filled with anecdotes of Roomi users actually moving in together: When I see that channel growing, I know we’re on the right track.

If, on the other hand, product-market fit isn’t happening for you, turn to your users first. Where are they getting hung up? Explore, pivot if you have to, and iterate until you have a product that satisfies your market with the least amount of effort.

Which Way Is Your Arrow Pointing?

Positive momentum is a vote of confidence from the market. Negative momentum lets you know something’s broken. And no momentum? That’s the real kiss of death.

It happened to me twice, when I was in my late teens and didn’t know any better. With no money for marketing, my dev shop and my classifieds site stagnated. We had enough organic traffic to keep going indefinitely, but I didn’t just want to build a business that could survive. I wanted to build a business that could scale. Stuck in a rut, I lost my drive and shuttered both companies.

Don’t make the same mistake. If you’ve hit a ceiling and can’t seem to break through, find someone who can, ideally an advisor in your industry. Plateauing is like suffering from a mystery illness—you can either stay at home, hoping it’ll magically fix itself, or you can find a doctor to diagnose you and prescribe the cure.
Ultimately, I think most founders who quit, quit too soon. I’ve been guilty of the same. Next time you find yourself stuck in that weird, uncertain limbo phase, remember this: If you have a problem worth solving, a solution worth using, and positive momentum, you’re already halfway there. After that, the difference between the founders who go down in history and everyone else comes down to just one thing—your will to soldier on.

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