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With inTheir20s, Landon Campbell gets execs, athletes and more to dish on their 20s

The podcast has interviewed the founders of Twitter, Bonobos, Apple and more on advice they have for people in their 20s


Landon Campbell - Headshot
inTheir20s creator Landon Campbell
Landon Campbell

What do Apple co-founder Steve Wozniak, former NBA star Tim Hardaway, and Miami Mayor Francis Suarez have in common? They all want to talk about their 20s with Landon Campbell.

Campbell, a Chicagoan and DePaul University grad, is the creator of inTheir20s, an interview podcast in which business leaders, celebrities, and other influential folks talk about what life was like in their 20s and lessons learned during that pivotal decade.

Campbell and his cohost, Michael Holmes, launched the podcast in June 2020. With the Covid-19 pandemic raging, and more business professionals at home and adjusting to Zoom calls, Campbell and Holmes quickly began landing A-list guests.

Beto O'Rourke, a former congressman who is running for governor of Texas this fall, was on episode 11. Hardaway, who will soon be inducted to the NBA Hall of Fame, appeared on episode 18. Early shows also featured the editor-and-chief of the Chicago Tribune, the head of Google for Startups, and the co-founder of Boka Restaurant Group.

But in April 2021, tragedy struck when Holmes died from a rare form a brain cancer that he was diagnosed with just one month prior. He was 22 years old.

"I felt like I had two potential paths," Campbell said. "Stop the podcast, or keep this thing we created together going and really take it further. I chose the latter." 

Campbell, who uses Holmes' microphone in his honor each episode, continued to land big-name guests who were eager to talk about their early career endeavors and offer advice to those currently in their 20s.

He booked investor Jason Calacanis, Twitter co-founder Ev Williams, Bonobos founder Andy Dunn, and NFL kicker Roberto Aguayo, along with the aforementioned Woz and Suarez.

Screen Shot 2022 06 17 at 10.48.17 AM
Landon Campbell interviewing APple co-founder Steve Wozniak
Landon Campbell

The podcast has now delivered more than 100 episodes, with Silicon Valley investor Tim Draper set to appear on an upcoming show.

The show is targeted toward "high-achieving 20-somethings," Campbell said. Early career professionals who want to learn how people before them found success. Campbell, who sits squarely in his podcast's demographic at 24 years old, said one major takeaway after interviewing dozens of business leaders is there isn't one path to a successful career.

"I think a lot of 20-somethings have it completely wrong," he said. "We're told we need to go on one specific path in order to find success, happiness and joy. 'You need to go to college or you need to hang around these people. You need to make a certain amount of money, or need to not prioritize your mental health in your 20s.' I hate hearing things like that. I'm showing clearly on my show that none of these guests really went on a traditional path."

Another main lesson? Don't be afraid to fail.

"Thats something big a lot of my guests say. We don't take a leap of faith because we're sacred we’ll fail, which in itself I think is failure," Campbell said. "If you don't do something because your are fearful of failure, you have failed. I'd love to see more 20-somethings fear failure less."

The podcast has also been a networking experience for Campbell, who through his conversation with Calacanis landed a job as the executive of virtual media at Inside.com, Calacanis' business-focused media company. He hosts another podcast for Inside where he interviews VCs.

Campbell said he's learning more about the venture capital ecosystem and has considered even launching his own fund some day. But for now, he's focused on helping young people navigate their 20s, one interview at a time.

"You don't have to follow what Woz did. You don't have to follow what Ev Williams did," Campbell said. "But I want people to listen to each interview and pick and choose what works for them."


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