What Four Exits Have Taught Me About Achieving Success

In my 16 years as an entrepreneur, I’ve learned that repeatedly doing the same things can lead to the same outcome: success. So how can my accomplishments inspire your own? Start by following my tried-and-true rules:

1. Go deep on research

Whenever I think I’ve discovered a market opportunity, I put in the effort to confirm I’m right. It may sound daunting, but doing some initial market research couldn’t be easier. 

Thanks to Google, it’s a cinch to find relevant articles, case studies, market analyses, and more. You can also use a service like Momentive to collect responses from those you know. To poll those you don’t know, Google Surveys works great. With the latter, you can screen for responses by including a couple of filter questions. They’ll help you get closer to your target market. I honestly prefer responses from outside of my network because I’m not being told what someone thinks I want to hear. 

Another good way to collect unbiased data is to use the Keywords Planner within Google Ads. After setting up a free account, you can search phrases related to your idea. The keyword planning tool will show you how many times those terms have appeared in searches on any given day. To get a sense of overall volume, you can also view historical search trends. 

2. Pack your team with people who are smarter than you

Once you’ve validated an opportunity, you’ll want to think about the skills you’ll need to seize upon it. Surround yourself with those that complement your abilities and fill gaps. This could be technologists, marketers, lawyers, etc. In the early days, you may not be able to hire this expertise outright. That’s why it’s critical to build out an advisory network, which you can create through cold outreach, your personal network, or even a community group.

When I ran a company that brought AI-based solutions to the business of space, I joined The Planetary Society. It’s an organization that bridges the gap between the scientific community and the general public. Through my membership I met the organization’s CEO Bill Nye — yes, that Bill Nye — and he agreed to become an advisor, providing my company with his unique perspective and expertise. 

Whether your team is a group of employees or advisors, you’ll need to allow them to demonstrate why you brought them in. A sign of good leadership is setting your team up for success and then getting out of their way. Treat them like the subject matter experts they are and let them apply their skills and knowledge in ways that will strengthen the company (and yourself). 

3. Create a brand that gets employees fired up

Successful companies have strong cultures. When I think about culture, I’m not focused on having beer on tap or foosball tables. Those things quickly became obsolete during the pandemic anyway. I’ve always believed culture is rooted in a company’s branding and messaging. Clear positioning, and an understanding of what your company is about, helps Day 5 employees be as inspired as someone who’s made it to day 500. 

When your team understands and embraces your brand, they can expertly explain how your company creates value for customers. Those intending to duke it out with other businesses in a talent war will see those free lunches and gym memberships erode profitability. However, when you use brand purpose and values to build culture, you’ll have the benefit of a workforce that’s focused and aligned.

4. Don’t be afraid to take (multiple) risks

Taking risks can feel weird for many people, especially the first few times you do it. But you just have to go for it. Fortunately, research from the Wharton School of Business found that entrepreneurs are more comfortable with uncertainty than others. 

If you’re not there yet, incorporate challenges that feel a little scary into your daily routine. The more “risky” things you do, the more comfortable you’ll become in situations where you’re not feeling completely confident. Soon you’ll become accustomed to uncertainty and will excel at tackling whatever comes your way. And don’t worry if you get a sinking feeling in the pit of your stomach. That just means you’re doing something right.

Also, it’s important to remember that if a risk doesn’t pay off, that’s a teachable moment. Failure is an opportunity to learn from your mistakes. Simply analyze what you did and adjust accordingly. As the saying goes, “If at first you don’t succeed, try, try again.”

Plan for success, don't just expect it
Speaking from experience, success isn't something that just happens. Success requires the right idea, the right people, and the right approach. So do your homework, check your ego, build a brand that excites employees, and don’t be too conservative in your habits.