What are the Struggles of Bootstrapping?

An article we liked from Thought Leader Geoff Roberts of Outseta:

The Unspoken Hard Bits of Bootstrapping

The challenges that I’ve faced as a bootstrapped founder simply aren’t the ones that are commonly talked about.  

The internet is littered with horror stories detailing the many challenges of entrepreneurship.

We’ve all read the tales of founders wrestling for years to find product market fit, of co-founders squabbling over equity, of the CEO riddled by anxiety as he drains his infant daughter’s college fund to keep his start-up afloat for another month.

Cautionary tales? Sure. But while these circumstances may be relatively common, ultimately they gain notoriety in the tech media simply because they are alarmist and clickbait. 

As I approach year four as a founder of a bootstrapped SaaS start-up, I can’t help but reflect on the hardships that I’ve encountered myself. As I have, I’ve had an overwhelming feeling—the majority of challenges that I’ve faced are by no means unique to me, but nobody is talking about them. This article is about surfacing those common entrepreneurial challenges that are gasping for some air. 

The compatibility of your idea and life circumstances with bootstrapping

The debate over the merits of bootstrapping versus going the venture capital route when building your company rages on—I for one am guilty of fanning these flames. But it strikes me that “bootstrapper” and “hypergrowth” describe paths and decisions that shouldn’t be seen as a part of our identity, or even as something to which we ascribe a personal preference. 

“I think we talk way too much about whether we prefer bootstrapping to raising venture capital, and way too little about which path is compatible with our business idea and life circumstances.”

I’d go so far as to say most entrepreneurial challenges that we hear being bemoaned are a direct result of your chosen path being incompatible with your business idea or life circumstances. When these items are in harmony, entrepreneurship becomes vastly easier.

If you’re building SpaceX, your idea dictates that you go the VC route—it’s too big, too ambitious, and too capital intensive to bootstrap such a company into existence. This is an extreme example, but this is the lens through which we should be assessing our start-up ideas as we decide how to fund them.

Generally speaking, “smaller” products are better suited to bootstrapping. Building a slack notification tool? Great! You can probably launch something like this in less than a month, give the project the opportunity to gain some traction, then make the decision to proceed or not from there. You’d be crazy not to bootstrap such a company.   

But if you’re building a bigger and more ambitious piece of software you need to look closely at the reality that it could take years to bring something of value to fruition. Can you afford a year without a paycheck? How about three years, or five? 

It’s worth noting that this isn’t solely a financial decision or one of product scope, but also one that will impact your...

Read the rest of this article at outseta.com...

Thanks for this article excerpt and its graphics to Geoff Roberts, the Co-founder of Outseta.

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