The best founders are learning machines. They are constantly pushing and trying to learn more.

By Adam Sylvain

When wikiHow founder Jack Herrick T’97 landed his first post-MBA role at McKinsey in 1998, he didn’t expect to be there long. Nearing the height of the dotcom boom, it was only a matter of time before his entrepreneurial ambitions led him down a different path.

“Like many of my peers during that era, I was working on a lot of startup ideas,” says Herrick, who co-founded his first venture, BigTray, a year later in 1999. He went on to build a second successful startup, Luminescent Technologies, and orchestrated the turnaround of early internet giant eHow before launching wikiHow in 2005.

There are few analogs for wikiHow’s subsequent rise from self-funded passion project to the largest how-to resource on the planet. Today, the website provides trustworthy instructions for people anywhere in the world seeking to learn how to do basically anything, from surviving an avalanche to baking banana bread.

From the beginning, Herrick envisioned wikiHow as a hybrid organization that uses the power of a for-profit business to accomplish a social mission. He has never wavered from that vision.

“Whenever we’re building anything, we’re asking ourselves, ‘How is this going to help people learn?’” says Herrick. “We’re thinking about that 40-year-old person who is trying to cook for the first time, or the teenager who lands on wikiHow for help with their algebra homework.”

His decision to forego outside investment with wikiHow was motivated by a desire for the business to be a long-term, independent project he could build over time. Herrick’s first two businesses, e-commerce restaurant supplier BigTray and semiconductor technology company Luminescent Technologies, were both backed by venture funding.

“Most venture-backed startups have a much shorter runway,” explains Herrick. “Putting wikiHow on that kind of growth schedule would have been like giving it steroids. It would have pumped up a bunch of muscle and made it look great for a while, but it would have been unhealthy for the business in the long term.”

As an angel investor in more than 100 early-stage companies, Herrick is quick to point out that taking outside investment is not bad. It all depends on the market need and the founder’s goals for the business.

“When I started Big Tray in the late nineties, you couldn’t launch an e-commerce company without outside capital,” he says. “If you take venture funding and have a product and a business that you really want to control and shape into something, it’s important from day one to make sure your investors are on board with your vision.”

An Innate Curiosity

Becoming an entrepreneur was always the goal for Herrick, dating back to the car wash business he ran as a kid in his Palo Alto neighborhood. He went on to study history at Stanford, the result of an innate curiosity he also possessed from an early age. It’s a quality successful entrepreneurs often share, says Herrick: “The best founders are learning machines. They are constantly pushing and trying to learn more.”

After graduating from Stanford, Herrick spent two years rock climbing in the Yosemite Valley and across the Southwest. One of the few possessions that traveled with him was a milk crate of assorted books he called his “knowledge box.”

It was his love of the outdoors and the school’s intimate scale that drew him to Tuck in the mid-90s. Herrick was still set on starting a company, though he admits he had no good ideas about what to do or how to do it at the time. Gaining a strong foundation in the fundamentals of business was at least a step in the right direction.

He cites legendary accounting professor John Shank as someone who helped reframe and sharpen his thinking. More than anything, Herrick says the Tuck experience helped him build and maintain lasting relationships, an essential skill for any entrepreneur or investor.

While management consulting was never the end game, Herrick also credits his brief stint at McKinsey for providing the time and experience needed to take his first steps as an entrepreneur. He co-founded BigTray in 1999, and just as the company was building momentum, the dotcom crash happened. With capital drying up fast, he had to sell the business for much less than it was worth—an experience that taught a valuable lesson.

“In the late 90s, businesses were selling for way more than their true value,” says Herrick. “Then in 2001, that flipped, and suddenly you had businesses being sold for much less than they were intrinsically worth. That was a big learning moment and something I filed away in my brain.”

His next venture was Luminescent Technologies. Although it never became a household name, the company co-developed a semiconductor design technology that’s still widely used today, including in many mobile phones.

Perhaps the most pivotal moment in Herrick’s entrepreneurial journey came with the launch of Google AdSense in 2003, which revolutionized the way ad-supported businesses could make money online. Herrick and his business partner, Josh Hannah, saw an opportunity to buy and resurrect eHow, a darling of the early internet that had been languishing.

A Wikipedia for How-To

Still at Luminescent, Herrick spent nights and weekends working on the site. Momentum built gradually until, once again, eHow became one of the internet’s most popular websites. While leading this turnaround, Herrick was also following a young company pioneering an entirely new open content model.

“I saw the potential for something much larger than what we could achieve with eHow,” says Herrick. “Wikipedia was not wildly popular at that time, but it was quickly becoming a go-to information resource. The thought was, ‘What Wikipedia is doing for the encyclopedia, I should do for how-to.’”

Fittingly, Herrick launched wikiHow on Wikipedia’s fourth birthday, January 15, 2005. He used Wikipedia’s open-source material, re-writing some of the source code and tweaking it for wikiHow’s purposes. Initially, it was built as a side project within eHow.

“It didn’t take off immediately,” says Herrick. “I think a year went by before anyone noticed anything was happening with wikiHow, but I could look at the numbers and recognize that it was growing well under the hood.”

Herrick soon realized that if he extended those numbers and wikiHow continued at its current rate of growth, it would eventually become much bigger than eHow. At that point, he knew he wanted to sell eHow and invest in wikiHow as a standalone business, but finding a buyer interested in that arrangement was not an easy proposition.

“Most acquirers are not going to want me to keep a business that would be in competition with them,” explains Herrick. “Fortunately, I found someone who really wanted the eHow asset and was willing to let me keep wikiHow without signing a non-compete agreement.”

While somewhat unusual, Herrick says the deal ultimately worked out well for both sides. Following its acquisition by Demand Media, eHow received a surge of capital and eventually went public. Demand Media’s IPO in 2011, valued at over $1 billion, was the largest internet IPO since Google’s in 2004, though eHow’s reputation later declined as major search engines began filtering out the site’s SEO-driven copy.

Instead of relying on a team of writers or freelancers, as eHow had done, wikiHow adopted a “wiki model” in which users of the site collaborate to create and edit content, which is reviewed and approved by other contributors. The site grew steadily. In 2009, wikiHow was receiving more than 20 million monthly visitors. That number reached 100 million by 2016. Before long, it overtook eHow and became the largest how-to website on the planet, and now covers nearly every topic in 19 of the world’s most common languages.

Innovating Along the Way

Among internet businesses, wikiHow’s success and longevity are rare. The site’s independence, mission focus, and deliberate growth strategy have all played a part. As technology and consumer habits have changed, wikiHow has also stayed ready to innovate and adapt along the way.

The transition from contextual to cookie-based advertising, a pivot from desktop computing to mobile phones, and the more recent emergence of artificial intelligence are just a few of the major disruptions. Herrick says mobile phones have fundamentally changed the way people contribute to and consume content on the site, and AI has raised the bar for the depth and quality of information wikiHow provides.

“Search engines are now using their own AI models to read and summarize content, like ours, directly on their search results page,” says Herrick. “We have to assume that a person may have most of the answer to their question by the time they come to wikiHow, and now they’re looking for something a bit deeper.”

“You want to play the long game and seek out true partners for your business.” —Jack Herrick T’97

With more than two decades of experience behind him, Herrick is quick to share what he has learned with the next generation of entrepreneurs and investors. When deciding where to invest, he says nothing matters more than the quality of the founder.

“I’m always excited to meet a founder who is persistent, continually absorbing information, and pushing for what’s next,” says Herrick. “More than anything, the person you are backing matters a huge deal.”

His advice for founders is to be 100 percent truthful about your strengths and weaknesses, avoiding the kind of brash, overconfident “blusterism” that will inevitably attract the wrong kind of investors.

“If you’re honest, you can put the investor in a position to help you work on your challenges,” says Herrick. “You want to play the long game and seek out true partners for your business, not just people who are going to give you capital and walk away.”

Twenty years after founding wikiHow, it’s fair to say Herrick has the how-to playbook written for building a mission-focused startup that lasts.

This story originally appeared in print in the summer 2025 issue of Tuck Today magazine.