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The founders of Salesforce and Udacity share advice on staying fresh at work

Entrepreneurs spend a long time navigating the ups and downs of building a business–here’s how they keep themselves motivated.

The founders of Salesforce and Udacity share advice on staying fresh at work
[Photo: Kurt Cotoaga/Unsplash]

For the fortunate entrepreneurs that have the opportunity to grow their companies from two to 200 or 20,000 employees, they’ll likely encounter a unique challenge–keeping the entrepreneurial spirit alive at every phase. You might have successfully navigated many long and winding roads, and now face miles of open road ahead. How do you stay excited and continually bring new ideas to the table?

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On the latest episode of Zero to IPO, Keeping It Fresh, we talked with four experts who have done exactly that. Here’s their advice:

1. Trust your momentum

Sebastian Thrun is a jack of all trades. He’s an adjunct professor at Stanford, founder of Google X, cofounder of Udacity, and now CEO at Kitty Hawk. Based on his track record, it’s safe to say he knows how to keep work interesting. His secret? He’s allowed the momentum of small steps to lead him to bigger moves, driving him from one successful opportunity to the next.

While running Google X, he was still teaching a few classes at Stanford and decided to put his AI class online, free of charge for students. After reaching a peak of 160,000 enrollments, approximately 16,000 students completed the course, and Thrun realized that the 412 top-ranking students weren’t even enrolled at Stanford. He didn’t set out to build a new company–but the success of putting that one class online ultimately inspired him to make a bigger move: building a new company, Udacity, to bring education to the masses.

2. Master the art of reinvention

As companies grow, leaders are under pressure to continue to bring new ideas to the table. Parker Harris, CTO and cofounder of Salesforce.com, has not only reinvented himself over his 20 years at the company, but also helped revamp the entire company’s development process and strategy.

In Salesforce.com’s early days, Harris saw production and communication problems creep into the engineering culture. Delays on software releases caused team members to feel like they were spinning their wheels on development and not actually building the future of the cloud. But two engineers approached him with an idea that completely changed the way they structured and delivered products–switching from “waterfall” to “agile” development cycles. That reinvention served as the foundation that transformed Salesforce.com’s development culture, and fueled its long-term growth and success.

3. Embrace the startup model

As CEO and founder, Melanie Perkins enjoyed Canva’s startup phase so much that she’s still embracing it today. Instead of having a few teams handle everyday business operations, she created a structure of 17 teams, or “startups,” that function more autonomously. The employees in each startup agree on goals together and even create pitch decks to keep everyone on the same page. It not only creates unity, but Perkins also feels that Canva has kept the entrepreneurial fire from “the old days” burning bright.

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What I found most compelling about Perkins’s unique approach is her philosophy that success isn’t finite. Instead of viewing success as a pie where everyone fights for one small piece, she highlights how the pie actually gets bigger with every win, which creates more opportunities for more people to be successful. In her eyes, when everyone is contributing their unique skills, there’s more pie to go around, and that’s better for the team and company in the long run.

4. Take a step back to see the bigger picture

Founders can sometimes fall into a rut as they struggle to manage their never-ending to-do list just to keep things running. But entrepreneur and venture capitalist Marc Andreessen will tell you that taking a step back to look at the big picture is the only way to keep things fresh.

Andreessen and his partner Ben Horowitz were early investors in my company, Okta–and they bet on us at a time when many were still skeptical about the future of the cloud. Andreessen and Horowitz believed in our vision, and their foresight and market knowledge enabled them to look past our terrible PowerPoint deck and see our potential. Startup founders can do the same by stepping back from the tactical day-to-day, anticipating where their industry is heading, and building the services that will help them meet future demand.

A metaphor that Thrun shared during our discussion stuck with me: He recently spoke to someone who climbed Mount Everest. The man spent six months training and preparing for the climb, and spent less than five minutes on the summit. For him, the climb was more rewarding than the view–and most entrepreneurs would agree. After building a company, they don’t sit back and enjoy their successes. They find new summits by exploring how their product can evolve, and ways the team can innovate and better serve their customers.

The love of the climb is a crucial trait to have, because it keeps entrepreneurs driven and excited about discovery–which is exactly what sets them on their journeys in the first place.

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Frederic Kerrest is the COO and cofounder of Okta. You can listen to the full episode, Keeping It Fresh, wherever you get your podcasts. Tune into Zero to IPO every Tuesday and check back here each week to read about the discussion on each episode.

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