Crazy Entrepreneurial Advice That Actually Isn’t

Why you shouldn’t keep your options open, don’t need a business plan, and other advice that may sound crazy but isn’t.

Crazy Entrepreneurial Advice That Actually Isn’t
[Photo: Flickr user Scott Anderson]

“If people aren’t calling you crazy, you aren’t thinking big enough,” says Linda Rottenberg, cofounder and CEO of Endeavor, a nonprofit organization supporting high-impact entrepreneurs in emerging markets. She defines high-impact entrepreneurs as people with “the biggest ideas, the likeliest potential to build businesses that matter, and the greatest ability to inspire others.”


Everyone has a dream, but many people don’t give themselves permission to follow it, or they get stuck, she says. We spoke with Rottenberg about her forthcoming book Crazy Is a Compliment: The Power of Zigging When Everyone Else Zags, and what she’s learned over the past 20 years of helping 1,000 entrepreneurs get unstuck. Here are her three tips:

Give Yourself Permission To Take Risks.

Rottenberg’s advice to entrepreneurs is the same advice she gives to Fortune 500 companies and parents at her daughters’ school. “The biggest barriers to success are not structural or cultural–they are mental and emotional,” she says. In other words, the biggest barrier is you.

Not that long ago, Rottenberg notes, the term “entrepreneur” was a rarefied, exclusive term used to refer to the fastest growing businesses, often in Silicon Valley, whose leaders were men. Now, Rottenberg says, the term refers to anyone making a bold move, and entrepreneurial skills can be taught to anyone – whether you’re starting a neighborhood initiative, creating an app, or launching your own business.

Entrepreneurs need to become comfortable with chaos because it disrupts the status quo, she says. “Make chaos your friend,” Rottenberg suggests. “Stop planning, and start doing.” People get caught up thinking they need to have a business plan to launch a successful business, but Rottenberg says it’s not required. With options like crowdfunding, Rottenberg says, today there are more ways to find out whether people want to buy what you want to sell.


Learn To Close Doors.

One of the worst pieces of advice, Rottenberg says, is to keep your options open. You need to learn to close doors. While it’s true that sometimes it’s not possible financially to quit your day job, too often people try to hedge their bets by having a full-time job and trying to launch on the side.

The founder of Liquid Paper, Rottenberg notes, started out as a secretary and later switched her focus to selling and marketing the product full-time. “We live in a world where no one wants to close doors,” she says. “At some point, [you] have to psychologically commit and move on.”

Create A Business Pre-Nup.

While nobody wants to think about legal issues or shareholder agreements at the start of a business relationship, Rottenberg says having one in place is critical to the success of a new business, citing it as the number one cause of failure.

It often happens where one person wants to create a lifestyle business, while the other partner wants to “go big,” she says. Without a shareholder agreement, there’s no roadmap for handling the misalignment of goals.

Linda Rottenberg will appear at Chicago Ideas Week on October 16.

About the author

Lindsay LaVine is a Chicago-based business and lifestyle freelance writer who's worked for NBC and CNN. Her work has appeared online in,,, NBC News, MSNBC, Yahoo, Business Insider, and Fox Business.