In our digitally connected, multi-screen world, where people hide their true selves behind layers of snark and our deepest emotions are expressed via emoji, conversation seems to be a lost art.

But as this week’s guest attests, conversation is one of the most important skills we possess, both in business and in life.

Michael Rothman is a digital entrepreneur, master conversationalist and storyteller, and all around fascinating guy. A founding employee at Thrillist, his latest venture is Fatherly.com, a lifestyle site for men entering parenthood - and a conversation in its own right (albeit of the digital variety).

Michael shares his point of view on how to create engaging dialogue, both face-to-face and through digital media, and even shares his notes from one of the best communicators in the world - Oprah Winfrey. Turns out, Oprah is a fan of Fatherly, and Michael has had the opportunity to spend time with her and her amazing staff.

On top of all that, Michael shares an amazing story about biking nearly 5,000 miles from New York to Los Angeles to raise scholarship money for his mentee and honor his beloved aunt. The grueling journey taught him a ton of lessons that still inform his life today, most of which were surprising even to him.
Here are a few photos from that epic trek:

Michael's epic beard. Michael and his pal Avi finally make it to the west coast. Michael's view for 55 days.

Key Takeaways

• Michael tells us how he got to know Oprah Winfrey, plus the most unexpected thing about hanging out with her. 3:35
• How to become more disarming in conversations, and why that’s important. 6:17
• Michael tells us who he is at his core, and why it’s important to know yourself. 8:23
• Michael breaks down the art of conversation, and shares how to maximize your networking opportunities. 10:40
• Strategies to drive past surface level questions and get to know people on a deeper level when you meet them. 14:40
• Michael shares the origins of Fatherly, and how it evolved out of Thrillist. 16:30
• Michael describes the “dudes to dads” cultural shift that inspired Fatherly. 17:20
• Michael shares the experiences that qualified him to launch Fatherly despite the fact that he’s not a father himself. 21:10
• Michael shares how he and his team developed the hugely popular piece, “The 50 Best Places to Work for New Dads.” 29:49
• Why Michael biked from New York to LA, and what it taught him about himself and his ability to overcome major challenges. 33:41

Links

• @MJRawth on Twitter
• Fatherly.com
• The Muse

Recommended Reading

• "Bike That Sh*t: Or That Time I Lugged Myself 5,000 Miles Across America" by Michael Rothman
• “The 50 Best Places to Work for New Dads” by Fatherly
• "The 36 Questions that Lead to Love" (New York Times article) by Daniel Jones

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