Mastering the Art of Rejection and Making People Remarkable with Guy Kawasaki

We just launched Season 4 of the Inspired Execution podcast and I had the privilege of ​​speaking with someone who has greatly impacted my professional career – Guy Kawasaki. He’s a successful venture capitalist, NY Times bestselling author, podcaster, and Chief Evangelist at Canva. I absolutely loved our conversation and will definitely be implementing some of the ideas Guy shared in the way I operate as a leader. 

Beautiful accidents

After welcoming Guy to the podcast and having my fanboy moment, we kicked things off by talking about his career journey. He studied psychology at Stanford University, which has served him well throughout his roles in sales, evangelism, speaking, writing, and podcasting. But this wasn’t part of any master plan for Guy. 

“If I wanted to reinvent history and indicate how smart I was and how I planned all this and how I was executing on my life goals, I would say yes,” he said. “But the truth is much closer to the fact that at the time I was at Stanford, psychology was one of the easiest majors. That's why I picked it.” 

Like many of the leaders I’ve spoken with, Guy’s career path has not been a straight line. Most of us don’t plot the course we walk. These are beautiful, accidental steps we take that help us become who we are along the way. 

Embrace rejection

Interestingly, Guy’s first job was in fine diamond and jewelry sales. He learned two big lessons from this experience. This first was the importance of empathy. If you’re trying to sell something (and, by the way, we are all in sales in some way or another. Think: getting your kids to pick up their dirty clothes), you first have to understand what the customer wants and what they’re trying to get out of your product. And secondly, Guy highlighted the value of grit. 

“One of the most important lessons of a young person's experience with sales is rejection because life is full of rejection. And the more you get used to it, the better you will be,” he said. 

Evangelism – the purest form of sales

What truly changed the trajectory of Guy’s career was getting a job at Apple, with the help of his former Stanford roommate. At Apple, Guy got his start in the world of software evangelism. 

“Evangelism comes from a Greek word, meaning bringing the good news. I brought the good news that Macintosh enables you to make the kind of software you always wanted to make for a market you could never reach,” he explained. 

Now, Guy is bringing the good news about Canva, a free graphic design platform that lets anyone create and edit images without prior design experience. Guy called evangelism the “purest form of sales.” He made sure to note the difference between sales and evangelism, though. Where sales, at some level, has your own self-interest in mind, evangelism is inherently about benefiting the person you’re “selling” a product or idea to.

Remarkable people

Somewhere between sales, evangelism, and writing 15 (!!) books, Guy also found time to be a serial entrepreneur. I asked him what is the one thing entrepreneurs and intrapreneurs should spend a lot of time on. 

He said, “By far, I think the purpose of an entrepreneur is to create customers. How do you create a customer? Duh, you have to finish your product. So the bulk of your effort should be getting a product to market.” 

Speaking of purpose, Guy shared that at the age of 67 he has finally found his true calling. He is on a mission to make people remarkable, and he’s doing just that with his podcast Remarkable People. In a sense, Guy’s entire career has been preparing him for this moment. With decades of experience at startups and large companies, he’s met the right people and gathered enough data to be able to ask the right questions of his podcast guests – questions that uncover how phenomenal leaders like Jane Goodall, Neil deGrasse Tyson, Steve Wozniak, and Kristi Yamaguchi, to name a few, got to be remarkable. (Oh, and if anyone knows Stacey Abrams, kindly introduce her to Guy Kawasaki. He would love to interview her!)

Guy joked that if he could give his younger self a piece of advice, it would be “DON’T QUIT APPLE.” But in reality, he’s enjoyed the journey and appreciated the breadth of knowledge he’s gained through different experiences. Each step has led him to where he is now – following his passion through podcasting and taking the occasional break from surfing to work. 

At the end of the podcast, Guy left us with one parting piece of advice: Never ask someone to do something you wouldn’t do. 

“Always think about… Are you asking your customers to do something that you would not do? Are you asking your vendors? Are you asking your employees? Are you asking your kids? I think that’s one rule of thumb I hope people would incorporate.”

Thank you for reading this week’s Inspired Execution podcast recap. You can find the episode and show notes here, or listen anywhere you get your podcasts. Don’t forget to tune into our next episode featuring HackerOne’s CEO Marten Mickos.