Founders aren’t the only ones who need to be comfortable with ambiguity. In the early years, everyone in your company must be ready to shoulder risk. Not just in their initial decision to join your unproven startup. They also need to be comfortable taking risks in the ways they do their jobs, especially when you’re still trying to figure out what the product is and how the business model should work. If your company’s culture doesn’t encourage taking calculated risks—trying out unproven features, or innovative marketing strategies, or unconventional pricing ideas—you’ll never grow 10x in the short amount of time you have to work with.

Here are six practices that will help you build a successful risk-taking culture:

1. Hire for entrepreneurial mindsets (at least among the first hundred employees). If the first 10 employees define a company’s culture, the next 90 solidify it. Of course, the bigger you get, the more you’ll start bringing in people who are psychologically more conservative. But the culture created by those first hundred hires will live on as your headcount grows to 500, 1,000, and beyond. The more entrepreneurial those first folks are, the more that ethos will be baked into your company’s culture.

2. Let your teams know that you know a project is risky. One year, Minted launched a new business around personalized handbags. “I told the team, ‘I don’t know if this is going to succeed, but let’s just go have fun with it,’” Mariam Naficy says. Her people tackled it with confidence, knowing that even the boss knew the project might not live up to her hopes. That gave them courage to run with it. “Nobody was saying, ‘Oh, God, we have to be perfect, so I don’t want to be on this team.’”

3. Make it fun. “Fun” as in playful, open-ended, and adventurous. Research has shown that the more playful a person’s mindset is, the more creative breakthroughs they have. When you task people with trying something new, you emphasize exploration and discovery, rather than producing a specific result.

4. Don’t “punish” employees whose projects fail. A culture where failure is penalized makes a founder’s job harder. People will start hiding bad news out of a reasonable concern for self-preservation. If a team fails at something, “Don’t come down on them too hard,” Box’s Aaron Levie says. And be mindful of what project you give them next. Putting “failed” teams on backwater projects sends a dangerous message. “People are going to start to think they should only work on high-profile, low-risk projects that are assured of success,” Aaron says. Then, over time, “the company is going to stop doing really innovative, interesting things.”

5. Set guardrails. The risks you and your teams take need to be proportionate. The size of a project should be appropriate to the experience of the person or team. Don’t ask someone to climb Mount Everest before they’ve summited a hill in their backyard. Establish guardrails regarding the size of the project, the budget, and/or the timeline. Set milestones for reporting on the progress they’ve made and what they’ve discovered. And define parameters for the circumstances under which you should kill the project.

6. Do postmortems and celebrate learnings. A “failed” project isn’t over until your team has studied what worked and what didn’t—and they’ve extracted insights that the rest of the company can learn from. Then break out the champagne. That’s what they used to do at Google X, which was launched by Sebastian Thrun before he went on to found Udacity and then Kittyhawk. “We always wanted to tell people that failure is about learning. When you learn something that gives you an important insight, that’s great,” he says.

Contributed to Branding Strategy Insider by: Frederic Kerrest, excerpted from his book, Zero to IPO: Over $1 Trillion of Actionable Advice from the World’s Most Successful Entrepreneurs

The Blake Project Can Help: The Brand Strategy Workshop For Startups

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1. The ability to thrive in ambiguity. Running a startup means never having near as much information as you’d like when it comes to making important decisions. Forget about taking 30 data points and running a regression analysis. You’ll be lucky to have three. You’ll effectively be guessing most of the time. Are you comfortable with never knowing anything for certain?

2. A knack for salesmanship. You’re going to be selling every moment of every day. Not just to customers. Also to investors: Why should they back you? To talent: Why should they abandon their secure jobs to come work for you? To vendors: Why should they give you favorable terms? And don’t forget your spouse or partner (if you have one): Why should they agree to let you imperil your family’s future with this crazy dream of yours?

3. Equal parts EQ and IQ. Most great founders aren’t the stereotypical socially awkward geeks. They’re actually great with people. They know how to inspire and motivate. They can put their egos aside and listen to their teams, advisors, and investors. So be sure your EQ (emotional intelligence) rivals your IQ.

4. Organization and discipline. When you’re the boss, no one is going to get on your case if you’re disorganized or slack off. You have to be your own backstop. Do you naturally create plans and knock things out on your own? Can you keep track of the big picture while also figuring out what needs to move forward in any given week or month?

5. Energy and drive. You’ve probably heard the expression, “It’s not a sprint; it’s a marathon.” That’s true, except that founding a company is a marathon made up of seven-minute miles. You need to keep moving, at all times.

6. Inspirational leadership. Can you set a vision—and a mission—and get people excited to follow you? This doesn’t necessarily mean pulling off a Henry V on St. Crispin’s Day (though kudos if you can). Inspiring people come in all kinds of packages. It’s not about how you do it. It’s just that you do it.

7. Self-confidence. When I started Okta, I always said I was “betting on myself”— that I had what it would take to grow Okta into a successful company. Sure, that confidence wobbled in our darkest times. But I always believed that if I just kept chipping away at our problems, I would find a way.

8. Resilience. Napster founder and early Facebook president Sean Parker famously said running a startup is like chewing broken glass—to succeed, you need to fall in love with the taste of your own blood. And it’s true. You’re going to get punched in the mouth every day. Are you the kind of person who’ll just keep getting up? Or will it eventually flatten you?

More Skills Entrepreneurs Need To Master

A lot of people think being an entrepreneur is just about coming up with a great idea. (In the tech industry, they often think it’s about having a great idea and being a great programmer.) But taking your idea from zero to IPO involves so many more tasks than simply building out the concept you’ve thought up. Take a look at this checklist, and ask yourself: Can I do that? Am I going to enjoy doing that? Because these things are what your job is actually going to consist of, especially the bigger you get.

• Can you recruit a team, especially people willing to leave safe jobs at established companies, when you can’t pay them as much and you can’t guarantee they’ll have a job a year from now?
• Can you attract investment capital, or at least convince a bank to give you a loan?
• If you’ll be selling to corporations, can you figure out the right executives to approach and convince them to give you time to pitch them?
• Once you have a prototype, can you persuade customers to test-drive it? Or better, to pay you to participate in a pilot program?
• Can you build a financial model, learn to forecast, and manage a budget, cash flow statement, balance sheet, and income statement?
• Are you comfortable with conflict? Can you resolve conflicts between people, such as differences of opinion among senior leaders in your organization who have competing goals?
• Can you tell a compelling story about your company, so that the media will want to cover you?

What do you think? If you were set loose today, could you do all these things? More importantly, would you enjoy doing all these things?

What Makes An Entrepreneur Tick?

Wisdom straight from the founders’ mouths.

Julia Hartz, Eventbrite

Serial entrepreneurs are missing a chip in their brain that says, “This might not work out.” That chip is just not there. They don’t tend to see the ways in which something might fail. They only see possibility. It creates a sort of infectious optimism.

Therese Tucker, Blackline

I like to make decisions. I like to be in control of my own time and life. I don’t answer well to others. I’m confident. I feel like I have the best idea, and everybody should buy into it. It’s completely unfounded, of course, but it carries you through when nothing else does.

Sebastian Thrun, Udacity and Kittyhawk

I live to empower people. When you come across something as powerful as hundreds of thousands of people all around the world all of sudden being able to participate in the gift of great education, there is no way you can’t do it.

Josh James, Omniture And Domo

I remember being in my freshman year in college, and we’d go sit up on top of the mountain and look down over the valley and be like, “Someone’s got to be on top. Why not me?”

Melanie Perkins, CANVA

I really like thinking about the future. I love spending a lot of time imagining what the world would look like.

Fred Luddy, Servicenow

An entrepreneur is somebody who so passionately cares about solving a problem that they will disregard a large percentage of what otherwise might be their life. I’ve had my electricity shut off, I’ve been evicted, I’ve had my car repossessed—not because I didn’t have money but because I didn’t take the time to pay my bills. The bills would come in, and if the envelope wasn’t pink, I didn’t even think to write the check.

Contributed to Branding Strategy Insider by: Frederic Kerrest, excerpted from his book, Zero to IPO: Over $1 Trillion of Actionable Advice from the World’s Most Successful Entrepreneurs

The Blake Project Can Help: The Brand Strategy Workshop For Startups

Branding Strategy Insider is a service of The Blake Project: A strategic brand consultancy specializing in Brand Research, Brand Strategy, Brand Growth and Brand Education

FREE Publications And Resources For Marketers