Ten Lessons from an Overnight Software Success

(and by overnight, I mean ten years)

At the Limeade 10th Anniversary party an employee asked me: "Can you tell us the top 10 things you've learned in the last 10 years as our CEO/founder?"

Just 10? How do you pack ten years of learning into 10 lessons? Sounds like a challenge. I like those.

Lesson 1 - Take on absurdly big challenges. I call it "relentless denial". Every entrepreneur believes they can overcome obstacles. It's not that we don't see them, lose sleep over them, or even freak out from time to time. Paranoia is de rigeur. It's that - independent of our actual capabilities - we believe we can win. Our big challenge became our mission: measurably improve well-being in the world. An improbable mission brings people together, attracts the right people to your team and focuses an organization.

Lesson 2 - Set short-term goals. With a moon-shot mission, it's critical to have more concrete short-term goals. Make it clear what we need to do today, this month and this quarter to make progress. People are motivated by progress, small steps and palpable wins. Teresa Amabile calls this the Progress Principle and it's a critical part of keeping people motivated. Having a long list of checked-off tasks is also a stress-reducer.

Lesson 3 - Have a chip (on your shoulder). In times of greatest fear and frustration, you need to call on a raw inner toughness. It doesn't matter what puts the chip there (in my case, three older brothers may have played a role). It's the reason we love watching football. It's the unglamorous grit and grind. The annoying attention to detail. Working when others are sleeping - because you want to. It's what the best venture investors look for but don't put in their spreadsheets - some small confirmation that this person will never, ever quit.

Lesson 4 - Never, ever quit. Anything worth doing is worth doing all the way.

Lesson 5 - Family matters. Your colleagues are in many ways family. Try to treat people like people; recognize the importance of employee well-being. We have high expectations of family to improve and grow and be trustworthy. You will work hard, and you must expect stellar results. But in order for us to thrive at work, we have to stay fresh, with lives full of family, nature, art and friends. Help each person find her sweet spot of stress. We know it's important for some parents to log off at three to pick up kids and that's okay. In fact, we encourage it. That's what family does.

Lesson 6 - Embrace conflicting ideas. Ever witnessed an argument like this: "We need to build this system to scale to millions of users" versus, "We need to ignore scale for now - and focus on speed of innovation for our users." The unorthodox answer here is "yes." Whether it's scale v. innovation, culture v. results, top-down v. bottom-up or short-term execution v. long-term vision - conflict is a real, natural part of business and life. It's yin and yang, dark and light, and the answer that works for us is "embrace the conflict." Execute on the A+ initiatives from each side of the conflict. Deep-six the B minuses.

Lesson 7 - Be data-informed. In fast-growing industries with rapidly changing market dynamics (most industries these days), you need business insights to chart your course. You need to collect, manage and ask the right questions of data. Your data, third-party data, big data, unstructured sentiment and the looks on people's wannabe-poker-faces. That feeling in your gut. It's all data. Being data informed is subtly different from being data-driven. Data are the road signs, and you're the driver choosing the roads you take. You need to know when to ignore the signs, get off the dead-end road you're on, or even jump out of the car. Trust your own computers, your brain and your gut.

Lesson 8 - Laugh. Make plenty of room for activities. (Warning: the attached link contains a swear word, a guacamole reference and a healthy reminder to brush your teeth.)

Lesson 9 - Build a brand, not a business. My favorite definition of brand is "what people say about you when you're not around." It's something you can't fake. Invest in something much bigger and more valuable than yourself, let it guide your most and least important business decisions and you will reap the benefits. Just know that it requires relentless and intentional curation, cultivation and reinvention. Most of your competitors won't think this way.

Lesson 10 - Give thanks. To your investors, customers, vendors and friends at work. To the people who empty your trash and serve you drinks on the plane. Most importantly to your family. Thank you.