Bobby Hobert is a lifestyle design coach and host of It’s The Bearded Man Podcast, but he wasn’t always a successful entrepreneur with a podcast — he started out as a full-time Uber driver.
Now I know how clickbait-y that sounds, but it’s true. Five years ago at the time of writing, Bobby was a full-time Uber driver right out of college. After being disillusioned by the idea of working in corporate America, he decided to pursue content creation. Uber subsidized his first podcast, called Purpose in the Youth, which was focused on unfolding stories of passionate young people.
The rest of the story takes a couple of left turns before Bobby ends up doing what he does now, which is coaching and hosting a different podcast. He had plenty to share about his journey — all of it very inspiring — that I want to dive into here.
Uber was Supposed to be Temporary
Bobby didn’t always want to be a creator, but after an internship in his junior year of college showed him that he definitely didn’t want your standard, corporate 9-5, he knew he had to find something else to pursue.
He started listening to the OG podcaster Lewis Howes' School of Greatness Podcast, and got really inspired by all of the stories that were shared, but also felt like he could never be as successful as the people Lewis interviewed.
So, he became even more interested in figuring out what his passion and purpose were. He laughs and notes that one thing he learned from business school was how to survey the market. And if you see something that doesn’t exist, you create the product to fill that gap in the market.
He decided to create a podcast that focused on young passionate people and how they got to where they were — he wanted it to be similar to the School of Greatness pod but for younger people in their twenties. He hoped his guests would feel more approachable than some of the heavyweights Howe has on.
When he started driving Uber full-time, he thought that it would be for maybe a few months and then he would “magically find a way to make a living full-time as a podcaster and creator.” Little did he know he would spend the next three and a half years driving before taking on a full-time job that wasn’t in the content creation industry at all.
The First Twist and Turn
One of the people he interviewed on Purpose in the Youth was the founder of a little company called Liquid I.V. — the founder was so impressed with Bobby that he decided to hire him. Bobby ended up working for the company for four years before re-pivoting as a full-time creator for his personal brand and podcast and as a lifestyle design coach.
When he was offered the job with Liquid I.V., he already felt like he had grown out of his first podcast. He decided to really go all in on working full-time, but right before the pandemic hit, says that he “got that creative itch again” and decided to start his current podcast, It’s The Bearded Man as a part of a larger personal brand he hoped to build.
I had to ask: why did he decide to cancel a podcast that was already doing well and start a different one? Conventional wisdom would say, if you’re working on something, keep doing it. If you keep pivoting, you’re not letting anything compound. There's a lot of psychological stuff at work where most people wouldn’t want to give up on something they tried to do for a long time — most end up brute forcing it, even if it doesn't feel right. At least, that’s how I felt when I decided to pivot my old podcast, Be Remote Local, to my new one, The Freedom Formula.
Bobby says that he did question himself a lot, and wondered if he was just giving up too early. But, looking back he’s so happy that he gave himself the time and space to slow down and make that pivot, even though at the time he wasn’t sure. He says that now, he’s practiced pivoting so much that he often makes big changes in his life without even thinking about it. “It’s like building a muscle — there’s going to be resistance, but the second or third time it gets easier,” he adds.
Going Out on His Own Again
That’s why Bobby’s most recent pivot wasn’t that scary. After four years at Liquid I.V., he says with full transparency that he started to feel a lot of resentment as his role and responsibilities kept growing. Yes, he was making six figures at this point, but was he aligned with what he was doing?
Bobby says no, which is why he decided to quit and go all in on himself and his new ideas. He also notes that he didn’t take a break or a vacation — he woke up the next day ready and raring, went right back to work, and hasn’t missed a beat since.
Now, in addition to his podcast, Bobby is focused on building out his lifestyle design coach offerings. When talking about it, he also insists on the difference between a “life coach” and a “lifestyle design coach.” He isn’t here to tell folks how to live their lives; rather, he’s there to help people design their lives to align with their goals and priorities.
His biggest goal is to help people be intentional with every moment of every day that there is purpose through his coaching program, social media, podcast, courses, etc. It’s not about hustling or grinding or being “productive” — it’s about creating a life that brings inner peace.
One thing he isn’t doing is working 60, 70, 80-hour work weeks as he builds his business. That’s the antithesis of what he teaches his clients, and he feels strongly that he wants to practice what he preaches.
It’s something that even I have to be careful about not falling into, and my conversation with Bobby was a great reminder of it.
This article was written by Neel from MaidThis Franchise, a remote-local franchise opportunity for people looking to escape the rat race and reach financial freedom. Learn more here.
