Why You Should Remove the Word “Bootstrapping” from Your Vocabulary

“Pull yourself up by your bootstraps.” It’s an idiom we’ve all heard—one that evokes images of grit, determination, and self-made success. But have you stopped to think about where this phrase comes from and whether it accurately captures its modern-day meaning? Here’s the twist—it doesn’t. And if you’re a small business owner or entrepreneur, I’m going to argue that it’s time to remove the word “bootstrapping” from your vocabulary entirely. 

The Origins of “Pulling Yourself Up by Your Bootstraps” 

Surprise, surprise—when this phrase originated in the late 1800s, it wasn’t a motivational mantra. It was sarcastic. Or at least it became sarcastic pretty quickly. 

The earliest recorded use is in a physics schoolbook, which posed the playful question, “Why can not a man lift himself by pulling up on his bootstraps?” At the time, it was a metaphor for something utterly ludicrous, akin to trying to push a wheelbarrow while sitting in it.

It was either scientifically impossible or impossible at the time due to technological barriers. Soon after, the phrase entered common speech as a way to mock the notion of achieving the impossible. 

As a matter of fact, I tried to create an AI-generated image for this article, trying every prompt I could think of, but the AI couldn’t even fathom what I was trying to say. If AI can’t imagine it, then how can a person? I’m kidding. Kinda.

But as time passed, the sarcasm got lost in translation. By the 20th century, “pull yourself up by your bootstraps” was no longer a way of describing impossibilities—it became shorthand for self-determined socioeconomic mobility. 

In all actuality, it was a way for wealthy people to clown poor people (who were tired of their socioeconomic situation and had the audacity to speak up about it) without coming across like a total jackass. And now that you know this, you can call them out on being that jackass. I know I do.

This shift in meaning carries weight, especially in the business world. Many of us have attached a new definition to the idea of “bootstrapping,” and it’s time to dissect how it’s perceived today—correctly and incorrectly. 

Misconceptions Around Bootstrapping 

Some people think bootstrapping means you can’t raise VC funding. That it’s like Plan B for when investors say no.

Wrong. Dead wrong. And this is where the misconception lies. 

Too often, bootstrapping gets framed as a fallback, a grudging admission of failure to attract venture capital money. But in reality, many founders choose to bootstrap their businesses—not because they lack options, but because they have sharply defined priorities. 

Bootstrapping can give you control, focus, and a sustainable growth path—three things that make an entrepreneur’s life much easier in the long run. And that’s a valuable lesson to learn for anyone starting or running a business. 

The Real Merits of Bootstrapping 

Sure, bootstrapping isn’t for everyone. For some startups—especially those with significant R&D, long ramp-up times, or hardware needs—VC funding is almost mandatory.   

But for many businesses, bootstrapping has a beauty of its own. Here’s why I believe it’s a model worth understanding and, in the right circumstances, choosing deliberately. 

1. Total Control = Total Freedom 

When you bootstrap, you own your company outright. No investors breathing down your neck, dictating quarterly targets, or pushing for strategies that don’t align with your vision. 

This freedom lets you play the long game. Want to invest in product quality instead of quick wins? Go for it. Need to pivot because of a market shift? You don’t have to ask permission. 

Founders who bootstrap often find that this autonomy lets them innovate more effectively and adapt more quickly—huge advantages in today’s fast-changing business landscape. 

2. It Teaches Financial Discipline 

Bootstrapping forces you to stretch every dollar. And while this might sound grueling, it’s actually a blessing in disguise. 

Here’s why. With no VC-backed safety net to fall back on, you have no choice but to focus on profitability from day one. Every decision—from hiring to product development—prioritizes sustainable growth. There’s no room for frivolous spending or vanity projects. 

Even better, this financial discipline naturally aligns your business with market needs. You’re not burning cash chasing speculative ideas. You’re building products and services that solve real problems for real customers—because your revenue depends on it. 

3. Long-Term Resilience 

Bootstrapped companies are built differently. They’re leaner, smarter, and more focused on cash flow than their VC-backed counterparts. 

During economic downturns, this gives them a huge advantage. While bloated startups scramble to secure their next funding round, bootstrapped businesses that have mastered profitability can continue to weather the storm. 

And when it comes to acquisition deals or exit strategies, bootstrapped businesses have another edge—a clean cap table. With no complex equity structures, they’re more attractive to buyers and can negotiate from a position of strength. 

Why It’s Time to Ditch the Word “Bootstrapping” 

Given all the benefits above, why am I suggesting we remove “bootstrapping” from our vocabulary? The problem doesn’t lie with the act itself—it lies with the word. 

“Bootstrapping” still carries the weight of its origins. It implies struggle, scraping by, and doing it all on your own. But in reality, this approach to business isn’t about being stubborn or going solo—it’s about being strategic. 

More than anything, it implies that your company is doomed to fail by trying to do something that’s impossible. And a self-funded company is anything but.

When you bootstrap, you’re not refusing help. You’re choosing independence. You’re not taking the “hard road” for the sake of pride—you’re making decisions that align with a sustainable and long-term vision. 

Many modern entrepreneurs and small business owners have already started reframing how they think about bootstrapping. It’s not a backup plan. It’s an intentional choice—one driven by strategy, not scarcity. The word itself, though, doesn’t do justice to this mindset. 

A Better Way to Talk About Business Funding 

What’s the alternative? Instead of categorizing businesses into “bootstrapped” and “VC-funded,” it’s time we use language that reflects the diversity of entrepreneurial journeys. 

Rather than saying you’re bootstrapped, maybe you’re “independently funded”, “self-funded” (my personal favorite), or even “customer-driven”. These phrases better capture the essence of what this model truly represents. 

Ultimately, the goal isn’t to glorify one path over another. Some businesses thrive with external funding; others thrive without it. What matters is understanding your options and making the right choice for your unique needs. 

RIP Bootstrapping 

Whether or not you ditch the word “bootstrapping”, and I sincerely hope you do, I want this post to inspire you to rethink how you approach funding decisions. 

Don’t fall into the trap of thinking VC funding is the only marker of success. And don’t undervalue the independence and resilience that come with forging your path. 

At the end of the day, building a successful business is about aligning your values and priorities with your strategy. Call it what you want—just make sure it’s intentional. 

*Drops mic with the word “bootstrapping” written on a piece of masking tape wrapped around it and kicks it across the room.*