"Anyone who tells you to follow your passion is already rich." How Scott Galloway paved his path.

The Path is a video series where I chat with some of the most influential leaders in the world exploring the successes, missteps, and key pivotal moments that shaped their professional paths. It’s through these stories that we can learn how to navigate our own career journeys.

My guest this week is Scott Galloway . Scott is a bestselling author, podcaster, entrepreneur, and professor known for his bold takes on business, tech, and society. This rich collection of talents and skills has made him one of the top advisors to the leaders of the world’s most important companies. But his path was far from assured. 

Scott's beginnings were modest. He was raised by a single mother in LA, "who lived and died a secretary." Family income was never more than $40,000. Nothing would foretell he would become a serial entrepreneur, founding nine companies; that, as Professor of Marketing at NYU’s Stern School of Business, he would be named one of the world’s best business professors by Poets & Quants; that he would sit on a diverse collection of boards, including the New York Times Company, Urban Outfitters, and Panera Bread; that he would reach millions through an array of social media channels.

"People just don't understand when you grow up without money," he told me for The Path. "It's like you have this ghost following you around, whispering in your ear, ‘you're not worthy’, and you start to believe it."

Even Galloway, famous for his advice that following your passion is a fool's errand, didn't see it coming. He told me that "when I was in high school, I thought I was going to make my living as an athlete. And then I got to UCLA, where there were real athletes, and figured out that wasn't going to be in my future."

And, oh yeah: He chose UCLA because it was close to home and inexpensive. He got rejected.

"When UCLA rejected me, I remember coming home one day and literally breaking down," he said. "I just didn't have the confidence or the sophistication to be scrappy and start applying to other colleges. I just thought, okay, the school closest to me has told me I'm not cut out for college. I need to start installing shelving."

Scott actually did get a job installing shelving, for $18 an hour — nothing close to the future he had imagined, but UCLA had second thoughts and gave him a spot. Scott was on his way. He was the first person from either side of his family to go to college.

He was a … mediocre student — "a 2.27 undergraduate GPA and spent the majority of my college years watching Planet of the Apes". But after school he landed a prestigious role at Morgan Stanley. It was his first job. He hated it.  

"The reason I left the corporate world was, I literally recognized, I don't have the skills for this. I was too insecure," he said. "I'm just not good at it. It wasn't because I thought, I'm so awesome. I need to let my, my freak flag of entrepreneurship fly."

It took 10 years, but Scott sold his first company — Prophet, a marketing firm which had landed such clients as WIlliams-Sonoma, Levi’s, and Apple — for $33 million. But it's not a path he counsels his students to take. "We have a tendency to romanticize entrepreneurship," Scott says.

"A ton of kids come to my office hours and they'll say, ‘I have offers from Google and Salesforce, but I really want to start my own business.’ And I'll say, ‘don't be a F…g idiot, go to work for Google,’" Scott said. “The majority of small businesses fail, the highs are very high. The lows are very low.” 

"Are you willing to risk public failure? Are you willing to be emotionally stressed? Are you willing to strain your relationships? Are you willing to borrow money from your in-laws with the prospect you might have to show up at Thanksgiving having lost it? Are you willing to sell everyone all the time?"

Entrepreneurs have put it a number of ways, but perhaps no one as succinctly as Scott: 

"The worst advice the billionaires give is follow your passion. Anyone who tells you to follow your passion is already rich," Scott said. "I applied for 29 jobs. I got one offer. The key to my success is rejection, or specifically my ability to endure it.” 

"Because if you don't get to 'no' a lot of times, you're never going to get to wonderful 'yeses.'"

My takeaways:

Even if you have nothing — maybe especially if — keep showing up

Scott started with no money, no connections, no clear plan. He kept showing up. He tried, failed and still moved forward. But he also learned, all the time. He questioned easy answers. He rejected conventional wisdom about success. He accepted that you don’t need to have it all figured out. You just need the nerve not to let rejection stop you from showing up.

It takes a lot longer than you think to know what you should be doing

"People mistake their hobbies for their professional career," Scott said. “But when you are just starting out your job is to workshop, as he put it. Almost nobody knows what they want — and can — do in their 20's. Getting to the thing you think you can be great  takes time and patience. And that's when — and only when — you get to follow your passion.”