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23 November 2021
Startup Founders, this is the only good reason to raise money
Unsplash © Kelly Sikkema

Startup Founders, this is the only good reason to raise money

In over 20 years of doling out startup advice, I try really hard not to tell people when to raise money and from whom. But I have no problem jumping into the “why.”

Here’s how I look at that “why.” Imagine, if you will, a bell curve of startup founders. On one end of that curve are the Elon Muskites, the ones who are just hell-bent on VC-as-a-metric and, to them, the amount of money raised means more than the value of whatever ill-fated product their startup is hawking.

On the other end of that curve are the Scientists, the ones who don’t care about the money at all. They’re just spending long nights trying to push an idea into reality, even if that idea is just batshit insanity disguised as a Rube Goldberg machine.

Most entrepreneurs fall in the middle, of course. And most of those entrepreneurs already know the dangers of handing over huge chunks of equity and control of their dream to someone they (let’s face it) barely know.

So on one shoulder, you’ve got the devil screaming “Raising money is the only way to succeed” and on the other you’ve got the angel whispering “Raising money is a treadmill to failure.”

Or maybe those roles are reversed.

The truth is raising money should only be for a land grab

A startup founder is a conqueror, and the empire they go to war over is a defined market. Like any good conqueror, they start with something small, maybe an island, and plant their flag on that island in terms of market share.

Then they look at the next island on the horizon. They should go conquer that.

But maybe that island is much bigger than the one they just claimed. Maybe it’s the shoreline of a continent. Maybe there’s an ancient empire already established there, with armies of its own.

When the conqueror can’t simultaneously defend their own domain and also expand their empire with only the resources they can muster on their own, they need outside funding — preferably funding that comes with added experience and connections — definitely funding that adheres to a well-thought-out battle plan.

And the lack of battle plan is where most entrepreneurs fail to raise.

What does that look like in the real world?

Again, I’m not going to tell you when to raise and from whom, but with every single startup I’ve either raised money for, helped raise money for, or helped fund (and I don’t invest anymore), I’ve learned that there are basically two directions in which those ships should sail.

Vertical expansion: You’ve found your market, you have paying customers, you’re solving a problem for them. Now go solve more problems for those same customers in that same market.

Those problems should be bigger, bolder, more expensive problems to solve. That requires research, experimentation, and longer sales cycles, so it requires a “war chest” of funding.

Horizontal expansion: You’ve solved a nagging problem for paying customers in a certain market. Now go solve the same problem a little differently for new customers in a new market.

Those markets should be lucrative markets, which means they’ll already have incumbent players (armies) that won’t take kindly to you invading their territory. Thus, you’ll need the war chest again.

What about all those other reasons to raise money?

Well, sure, most of those reasons can be valid if you want them to be. But here’s the thing. Raising money isn’t just about the pitch and the term sheet.

Venture Capital investment is a perpetual cycle of raise-and-conquer. If for whatever reason you raise and don’t conquer, the chances of your startup raising again are dramatically lowered. And you still have armies to feed and equip.

And that’s where most startups fail to scale.

Before you ask yourself: “Can we raise the money to accomplish this goal?” ask yourself, “Do we need to raise money to accomplish this goal?”

If the goal isn’t additional market share, and a lot of it, and the answer isn’t a definitive “yes,” then it’s probably not time to get on that treadmill of perpetual raise and conquer just yet.

Hey! This post comes from an answer to a question from a real, working entrepreneur. If you’re looking for startup answers and advice, try Teaching Startup for free. The paid version has hundreds of answers for just $10 a month, or less than 1% of the cost of a traditional advisor.

This article was originally published on Medium by Joe Procopio

Joe Procopio is a multi-exit, multi-failure entrepreneur. He is the founder of startup advice project and is the Chief Product Officer of mobile vehicle care and maintenance startup Get Spiffy. You can read all his posts at