When Millionaires Make Mistakes

Passion is Everything.

Jeff Clark

Max Mullen knew he wanted to launch a startup, even if he wasn’t fully enthusiastic about the idea. In 2010, he introduced a social networking tool called Volly. The business failed within a year.

“I didn’t have a passion for it,” he admits. “Passion drives a sense of urgency and tenacity; without it, when you reach a stumbling block, you give up. It made me realize that if I’m not passionate about something, it’s not worth doing. I’m passionate about Instacart, and that has driven its success.”

Successful Businesses Can Rise From The Ashes of Failure.

Natalie Brasington

“I was working on a startup for about a year and a half,” says Taso Du Val. “It didn’t go very well. It went nowhere. No one believed in the idea. No one believed in me. No one would give me any money. It was rock bottom.”

However, he persevered. He worked on the popular art startup Art.sy, putting together an angel round with former colleagues from social media company Slide, where he had served as a lead engineer. While doing so, he “stumbled across” the opportunity for Toptal, his successful staffing business.

“What I’ve learned looking back is that no matter how hard times are, and personally, they were hard—my father was dying, I had no money and no one would fund me, people didn’t believe me—looking at that, it’s like, ‘Well, I’ve been there. How does it get worse from here? I’ve already dealt with these horrible situations, and I’m past it.’ Getting past those really challenging situations makes you a stronger person.”

Staffing and Managing Are Learned Skills.

Ewan Burns

Few people are born leaders; most entrepreneurs learn on the job how to get the best results out of their staffs. Glossier’s Emily Weiss admits that at age 30 she’s not the most experienced CEO. “Managing is not what I thought it was going to be,” she says. “I always thought managing was about putting people in their place—finding the perfect fit for them. But I’m learning it’s better to get people out of their place. That’s where they’re more productive and useful.”

As a young entrepreneur, she has come to realize that evolving companies have evolving personnel needs. “I also learned to take the short view on hiring, making sure to hire for the next 18 months, instead of looking for that person who’s going to have the job for the next three years. We’re going to be a totally different company by then, and who I need in the future is different than who I need right now.”

Rushing to Market Rarely Succeeds.

Jude Edginton

Austin McChord learned this the hard way.

“We’ve succeeded through a string of failures. There have been an enormous number of challenges, especially when the business was really small,” says the founder of data recovery business Datto. “We pretty much made every imaginable mistake out there. At one point, a competitor released an updated product … so we created a new product very quickly that we thought could compete. We ended up making a huge mistake and created a product that didn’t work very well. That was an incredible learning experience of everything not to do. The pain we put some of our early customers through with that product was immense and almost put us out of business.”

McChord and his team managed to regroup and create a successor to that failed product that was “incredibly reliable and allowed us to continue to grow much more than with anything we’d built before. That was our Siris product line, which now represents north of 80 percent of our sales.”

What did he learn? “It’s really important that everything we do is tested thoroughly and that the product is reliable, because people absolutely depend on it, and your reputation is everything. When you ship a product that is not reliable, it’s incredible how much you can damage your brand and reputation, and how fast that can happen. Nothing can make you fall out of favor more than having a tarnished brand, so you have to work really hard to make sure your products live up to the promises that you make.”