Fast Company/Jenna Abdou: I’ve Interviewed Over 300 Entrepreneurs–Here’s Their Most Counterintuitive Advice

Fast Company

    08.24.17 9:00 am

I’ve Interviewed Over 300 Entrepreneurs–Here’s Their Most Counterintuitive Advice
This podcast host shares four of the most surprising things she’s learned by speaking to hundreds of startup founders.
I’ve Interviewed Over 300 Entrepreneurs–Here’s Their Most Counterintuitive Advice
[Photo: George Coppock/iStock]

By Jenna Abdou5 minute Read

Three years ago I started a startup podcast because I thought founders were crazy. Why would a sane person willingly endure such intense risks? Part of my curiosity was personal: As a recent college grad just setting out to navigate the workforce, I wanted to understand how they coped with levels of uncertainty that felt to me, anyway, like a bag of bricks on my chest.
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More than 300 interviews later, I’ve learned that the most successful entrepreneurs’ real strengths aren’t necessarily their product visions or executional abilities. Those certainly matter, but their habits and mind-sets might carry even more weight. And as I’ve discovered through all my conversations, those aren’t always what you might expect them to be. Here are four of their best, yet counterintuitive, bits of advice.
1. Specialize In More Stuff Than You Think You Have To

When Packagd founder and Kleiner Perkins partner Eric Feng seeks inspiration, he looks to tennis legend Roger Federer. “The thing I love about Federer is that there is nothing he doesn’t do well,” Feng told me. “He plays on all surfaces. He can serve, volley, hit a strong forehand and backhand.” That observation has inspired Feng to develop skills outside his cut-and-dried job description as a technical founder and the former CTO at Hulu and Flipboard.

“I don’t want to have a weakness–something I have to avoid because I can’t do it,” he says. “My day job at Flipboard was leading the engineering team, but I think the biggest contribution I made was working as an account manager on our Samsung partnership,” which he notes was a much more specialized undertaking.

Related: Five Habits Of The Most Creative Entrepreneurs

Founders are eventually advised to stop wearing so many hats, to delegate so they can spend more time making strategic decisions. But Feng has never stopped immersing himself in new fields–identifying skill sets he lacks and devising clear plans to develop them. That may seem like a misuse of energy, but he’s found it has real hidden value. “It’s particularly important to be an all-court player in startups because you never know how your company will change or where the biggest opportunity will lie,” Feng explains. That’s not just a temporary, early-stage thing, he believes, it’s a key part of the overall experience. “If you’re only specialized in one domain, you might miss it.”

So rather than sitting in on a design meeting, mock up a design and present it. If you’re trying to make some strategic decisions about your company’s customer support, respond to support emails for a month. The goal isn’t to observe a skill. It’s to practice it enough so, that if needed, you can perform it.
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2. Share What Annoys You, Then Have Your Team Do The Same

Since her founding days at Gilt, Fitz cofounder and former Glamsquad CEO Alexandra Wilkis Wilson has kept going back to one key exercise with her team: Everyone completes the statement, “Here’s what you need to know about me to influence me: . . .” It’s a trick she learned from executive coach Barry Carden for creating “an opportunity to share professional pet peeves with one another and say, ‘Look, if we are going to work together this is what you need to know: This is what I respect. This is what drives me nuts. This is what I will deliver, to you and what I expect you to deliver in return.'”

A company’s cultural values usually dictate what successful communication looks like. But those rarely get deep or personal enough to expose what employees actually dislike about their work experiences or personal interactions. And as Wilkis Wilson sees it, addressing those head-on is the greatest way to decrease friction. “When you’re working in a high-stress environment you have to be honest with each other,” she says. “You can’t make assumptions, because everyone is coming from a different place.”

Try this exercise with your team and start with your own statement. Urge everyone to be as honest and descriptive as possible. It may feel uncomfortable at first, but it might be a great way to promote trust and collaboration faster.

Related: 8 Entrepreneurs On The Magic Moment When They Knew Their Startup Had Made It
3. Forget Your Competition

“Competition doesn’t matter,” Andy Rachleff, who cofounded both the fintech company Wealthfront and the VC firm Benchmark Capital, told me. “The only way to win is to delight the customer. You can’t better delight the customer by paying attention to your competition.”

It’s human nature to think about competitors, so as a leader it can be hard to get your team to switch their focus. But the next time your competition comes up, Rachleff advises shifting the conversation toward a concrete action you can take to improve your product.
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Since Rachleff’s return as CEO last November, Wealthfront has aimed to widen the gap with its competitors by launching seven new features, with an eighth forthcoming, he explains, not to mention a complete brand redesign. According to Rachleff, clients responded by depositing more money and referring friends to the service, leading Wealthfront to see about $12 million a day in new capital.

“As a leader, it is imperative that you help your followers understand that reacting to your competition won’t get you to the leadership position. You’ll only lose less quickly,” Rachleff says. “I love to joke that I come from the Ricky Bobby school of management: If you’re not first, you’re last. You can’t become first by doing a better job of what your competition does.”
4. Stop Making Things Happen

Jennifer Rudolph Walsh is the head of the Worldwide Books Department at WME, where she represents authors like Oprah Winfrey and Sheryl Sandberg; she’s also the founder of an event series called Together Live. You’d never question her ability to get stuff done.

“I was so busy hustling, making things happen and making them right in my 20s and 30s. Then, in my 40s,” Rudolph Walsh says, “I discovered this magical place of making things happen and then letting them happen. That’s the secret space for me: Trying a little easier. Listening a little more. Not rushing to get to the end of the story or control the outcome. Just living inside of it.”

This state of mind can feel unrealistic managing a team and hitting deadlines. It might strike some entrepreneurs as too passive or laid-back. But as Rudolph Walsh sees it, it isn’t a mandate to leave things to chance. It’s a conscious decision to make room for serendipity, revealing opportunities that are right in front of you but hidden by tunnel vision.

Without this mind-set, she explains, it’s a lot harder to turn small ideas into meaningful outcomes. “As a result of the work I’ve done around this, I’m as happy as I’ve ever been,” Rudolph Walsh explains. “The level of peace I can have in the middle of a storm amazes me.”

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