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3 scrappy CEOs who bootstrapped their way to the big leagues

Posted by Grace Townsley

November 28, 2022

Bootstrapping refers to launching and growing a company with nothing more than the resources you have available, without leaning on investors or debt. It’s all about leveraging what’s in your hands to create a successful business, from the ground up. 

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In today’s article, we’ll look at three CEOs who bootstrapped their way to incredible success. 

Bootstrapping takes exceptional creativity, problem-solving and an attitude of persistence 

Building a business with abundant resources, ample time and a solid team is hard enough. But when it comes to making something from nothing, it takes a special kind of entrepreneurialism to be successful.

As you’ll discover in the real stories below, bootstrapping a business to a multimillion dollar valuation — or more — isn’t easy. But for committed founders with a good idea and a willingness to do what it takes, anything is possible. 

ButcherBox’s bruised founder bootstrapped his way to $600M in revenue

Mike Salguero, CEO and co-founder at ButcherBox, a meat delivery company, is no stranger to entrepreneurialism. But his first major venture was more crash-and-burn than to-the-moon. 

That early company raised $30 million in venture capital but went bankrupt within a few years. Days after leaving the failed company, Salguero launched ButcherBox, and this time he was determined to make it without taking on debt.

He partnered with an experienced leader in the meat delivery industry and leveraged equity in the new company to get help with branding and marketing. Then the entrepreneur launched a successful Kickstarter campaign, raising eight times his goal during the pre-order period.

Using that funding, Salguero expanded the company by partnering with influencers, bloggers and nutritionists across the country. In 2015, ButcherBox generated $275,000 in revenue. In 2022, it’s expected to bring in over $600 million.

How Jiggy Puzzles’ three-person team bootstrapped their way to 250,000 puzzle sales in three years

Our second example of go-for-broke entrepreneurs who bootstrapped their way to incredible growth involves a woman, a puzzle and the pandemic. 

At the end of 2019, Jiggy Puzzles’ CEO and founder Kaylin Marcotte started a small direct-to-consumer frameable puzzles company. As a first-time female founder, she simply aimed to turn her passion for puzzles into a fun pastime that didn’t rely on phones or TV screens. 

With $25,000 from her own savings, Marcotte began to find unique artists with eye-catching designs — the kind of art pieces puzzle-doers would want to frame. She set up a profit-sharing program with these artists so they had a stake in the game, too. 

As a bootstrapper with little experience, Marcotte quickly partnered with other entrepreneurs in similar industries. They helped her navigate the complexities of product packaging, shipping and supply chains, especially when the pandemic disrupted her suppliers and triggered a massive boom in her sales. 

Today, Jiggy Puzzles enjoys a 31% customer retention rate and $1 million in annual sales. And all with a simple three-person team at the helm. 

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Cloudinary is the ultimate bootstrapper’s success story, with a $2B valuation

Our third bootstrapping success story is about a unicorn, a privately held startup company valued at over $2 billion. That makes Cloudinary a unicorn, twice over. 

In 2012, three developers grew tired of the tedious process of sifting through, editing and posting digital media. So they developed an artificial intelligence tool that completely transformed the way over 10,000 brands handle their digital assets. 

Cloudinary CEO Itai Lahan says they aren’t anti-capital, they just didn’t see a need for it in the early stages of their business. In fact, Cloudinary made a conscious decision to focus on its customers and employees at every stage of business, rather than chasing investors or short-term financial goals. 

Instead of pushing to grow as fast as possible, Cloudinary aims to develop solutions at the speed of need. And because the company didn’t have external investors expecting specific growth or revenue goals, or unrealistic timelines, Cloudinary’s founders have enjoyed making their own growth path along the way. 

Today, over a million developers use Cloudinary’s technology, but the company has no plans of leaning on their financial partners any time soon. 

Whether you’re a new entrepreneur or in the thick of bootstrapping your own business, let these stories be an encouragement

As a bootstrapping founder, you’ve got full control over how your company is run. You’re in the driver’s seat, and you call the shots. 

You’ve got a unique opportunity to carefully guide every aspect of your company, from how you spend each dollar, to the direction you go in this quarter and the next. And without the risk of bankruptcy, creditors and disappointed investors looming over you, you’re free to grow your business at the pace you see fit. 

In short, make the most of this bootstrapped season. It’s a rare opportunity to discover just what you’re capable of — and maybe even surprise yourself.

Want more? Escalon’s one-and-done Essential Business Services can help your business scale up faster while saving you money with our outsourced finance & accounting, HR and business insurance services. Talk to an expert today.

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Grace Townsley
Grace Townsley

As a professional copywriter in the finance and B2B space, Grace Townsley offers small business leaders big insights—one precisely chosen word at a time. Let's connect!

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