“Bootstrapping”: How entrepreneurs can control their own destiny

After meeting in a precollege summer program, Jesse Pujji and friends Chris Amos and Nick Shah launched a social media platform and brainstormed other ventures as college students. “None of our efforts went anywhere, so we all took jobs in consulting and investment banking,” says Jesse. “In my heart, I knew I was an entrepreneur, but my head told me to go work at these fancy companies and see what they were all about. I did, and enjoyed them, but they were not my dream.”

It took them about four years to walk away from their jobs and start the digital marketing firm Ampush (named for the first two letters of each of their last names). They built the business without taking external funding, eventually managing more than $1 billion of digital media spend, growing to over 100 employees, and partnering with brands such as Uber, Stitch Fix, and Hulu. In 2023, they sold Ampush in a mid-eight-figure exit. But Jesse was just getting started.

“There are two types of entrepreneurs,” says Jesse. “The ones who have an idea that they can’t get rid of and they just want to see it exist in the world and the ones who want to be an entrepreneur because they love business and love the idea of being a leader. I am very hard in the second camp.”

He says he was always a “very commercial kid. My mom tells a story about how after Halloween, she got a call from my elementary school principal that I was selling my candy for a quarter a piece. My brother and I saw an ad in Boy’s Life magazine for a catalog of items you could sell to people. We ordered it and went door to door selling tins of popcorn and other stuff. We became really good at it. Then with my brother and some friends, I started a snow-shoveling business in middle school and a DJ business in high school.”

Jesse’s entrepreneurial spirit was ignited by his father’s example. “He came to St. Louis from India in the late 1970s and started his own business from scratch. I remember making copies and answering the phones at his office. One time I said he was busy, and he got mad, telling me you never want to be too busy for the customer. His experience showed me what it was like to be your own boss and control your destiny. It also gave me the desire to create a longer runway to learn and grow the business without external capital.”

By the time he was 25, Jesse had left McKinsey and was working at Goldman Sachs. It was at Goldman that he created the vision for a new company and shared his thoughts with Nick and Chris. “We’d had a lot of good ideas, but hadn’t done anything about them. I said, let’s create a company that builds businesses. It’s going to have ideas and execution. It’s going to attract and retain the best and brightest. It’s going to have great values. In six years it will be a holding company with nonprofit and investment arms. And we’ll do it by building businesses, getting them running, hiring people to lead them, and keep going until world domination occurs.”

Jesse says that vision is an important part of his story because it illustrates that while he had a desired future state, he “had no idea what it took to build a business, to find a customer, to do any of the most basic stuff. I wanted the business, but I didn’t know how to start it.”

What he did know, though, was that he didn’t want to rely on external capital. Ampush would be built by bootstrapping (from the phrase, “pulling oneself up by one’s own bootstraps,” referencing someone who achieves success by relying solely on personal resources and ongoing effort). He had three reasons: “Number one, from my dad’s example I was taught that a real business sells a product or service for more money than it costs to make and deliver, so you earn a profit. Most venture-backed startups are never profitable.

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“Number two is also related to my dad, and he still says it: being an entrepreneur is controlling your own destiny. That’s what Warren Buffett meant when he said Berkshire Hathaway would ‘never depend on the kindness of strangers to stay in business,’ ” says Jesse. The third reason is rooted in his finance background: “I saw businesses that made money and the value of being able to invest or compound their cash flow. This ‘Wharton finance angle’ was very different than that of a Stanford kid who studied computer science. I wanted a business that would generate cash and then let us fund our own growth with it. That was a big part of the dream.

“What we were afraid of was raising $1 or 2 million and then burning through it for 18 months trying to figure something out,” he says. “We didn’t want to take such a big bet. Instead, we wanted to buy time growing organically, so we chose bootstrapping.” Jesse adds a caveat, though, acknowledging that today’s venture capitalists are trying to provide more in terms of guidance and insight to their portfolio firms than he was seeing when they started Ampush.

Jesse and his cofounders were poised to start Ampush, but they had bad memories of starting a social network a few years before without a revenue model. “Since then, we had worked at these fancy companies selling services to very large clients,” says Jesse, “so we knew how to sell and how to present, and we thought we could figure it out. Selling directly to consumers felt too chancy, so we looked for better ideas that would be profitable and also give us more runway to learn and grow as people.

“Our parameters were very unique,” he recalls. “We wanted to be in an industry that’s easy to get into and that we could bootstrap and get to profitability. Then once we get to profitability, we want to start doing other operations. So we started scanning for those criteria, and that’s how we found our way into digital marketing. It was a growing field, and it would help us learn and grow quickly.”

Although their businesses are quite different, Amy Norman and friend and business partner Stella Ma had a brainstorming session similar to Jesse’s before they launched Little Passports, an educational subscription service for children later acquired by education company BEGiN. Amy said she and Stella realized they had a shared passion for global citizenship and agreed that their new business should be bootstrapped. She explains that the media’s current focus on tech and health care unicorns can leave entrepreneurs with other business ideas and concepts of achievement feeling discouraged. “Be clear about your own definition of success,” she counsels. “There are success models outside of this bubble.”

Although Jesse and his partners saw an opportunity in tech, their desire to bootstrap meant they needed a business venture that didn’t require venture funding to start and scale. Soon after launching Ampush, they discovered Facebook’s API, or application program interface, which allowed access to Facebook data to target ads. They created and ran ads for clients including Uber, Madison Reed, and Dollar Shave Club.

Before Ampush was sold, they managed over a billion dollars in ad spend from Facebook. “We were one of the big catalysts driving that whole industry,” says Jesse. “We acquired drivers for Uber in 60 countries, a million subscribers for Dollar Shave Club, and millions of gamers for Clash of Clans. We hired nearly 500 college graduates and trained them like McKinsey or Goldman. We pioneered large-scale marketing and the data-driven version of it.”