Charles Bern is a serial entrepreneur because he finds a little bit of excitement in everything. Whenever something tickles his fancy, or whenever it ignites a passion in him, he gets the itch to get involved. After all, the idea of entrepreneurship was engrained in him when he was very young.
“My dad was also an entrepreneur, and I used to read the business section after he was done with it. And so, in my head, I’m like, ‘Oh, when I grew up, I’m gonna start my business, I’m gonna run my business,” he says. “I think for a lot of it, it’s just mixing your passions with the mentality of being like, I want to start something and run something.”
That mentality has helped Bern dip his toes – or dive in, head first – to various industry pools. He started a speed dating company when he was 22, and briefly held a record for the biggest speed dating event in the world. He’s helped produce films. He started a human-centered design agency. He raised over $200 million in the cannabis industry. And he’s worked with iconic brands like HBO, Chanel, Spotify, and Google. And in terms of what’s next, he’ll know when he feels that spark, that fire that means he’s connected to a specific vision.
“I tend to start with a goal and work backwards. So if I am changing channels, I know what the North Star is, and I set that goal. I find I do much better work when I’m like, ‘Okay, this is what I’m planning to do.’ And then everything before that is just figuring it out,” he says. “It’s a journey of self-discovery in a lot of ways, and sometimes you don’t know until you try it. Then you realize, ‘Oh, this isn’t for me’ or or sometimes you try it and there’s parts of it where you think, ‘Oh, this was amazing. This was incredible.’”
It’s what Bern calls “a little bit of ADD,” or the idea of being “a generalist,” that allows him to cast such a wide entrepreneurial net, but it’s also taught him some valuable lessons. Bern values the input of experts, and he’s always keen to ask for help and input. “You have to develop your principles what’s going to be your guiding lens for making decisions. And I think everybody has different a different lens on things,” he says. “Being humble and asking a lot of questions, I do find as a generalist, really helps in some areas. But also you have to be willing to ask the questions where specialists that you trust can answer them.”
That concept of sharing skills, Bern says, is critical in an entrepreneur’s success. “There are a lot of moments as an entrepreneur where you’re very problem-focused and solution-oriented,” he says. “Whether it’s a big problem or a little problem, you’re like, how can I figure this out? And, from what I’ve seen, the biggest key to success for an entrepreneur is just being determined. It’s like, okay, we’re gonna try this. Maybe it doesn’t work, but we’re gonna try this, even if it doesn’t work. And if I do something and I’m not good at it, or I don’t like doing it, what are within my resources to figure out a different way to get this to work?”
All of those obstacles Bern has overcome, all of the things he’s figured out, are what really drive him. “Obviously, it’s nice to be able to measure success in terms of monetary outcomes. That’s just the world we live in. And it’s a much easier thing to measure. But you also have personally fulfilling projects, the projects that I can look back on and be like, ‘I’m really proud of this. I’m very happy I did this,’” he says. “Success is also like taking things, taking something with you from a past project that helps you either with momentum or with your personal brand. Success is very much learning.”
