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:

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

This is episode is brought to you by the snack geniuses at SnackNation.

SnackNation is a healthy office snack delivery service that makes healthy snacking fun, life more productive, and workplaces awesome.

To try a free SnackNation discovery box (featuring 15 delicious snacks your team will love), visit get.snacknation.com/ao. You'll also receive a complimentary copy of the 2016 Ultimate Guide to Creating An Awesome Office.

When faced with adversity, some people crumble.

Andres Izquieta is not one of those people.

Andres is a fashion designer, serial entrepreneur, and the CEO and co-founder of Five Four Club, an online men’s clothing subscription service. 

In 2008, Five Four (then a retail and wholesale outfit) was on the brink of failure. The worldwide credit crisis that gave birth to the Great Recession was decimating the retail industry, and it looked like Five Four might not survive.

But Andres and his business partner had other ideas. They brought the company back into the black by pivoting to a men’s fashion subscription service.

The strategic shift paid off. Today Five Four Club has more than 70k active monthly subscribers, and is about to launch several new verticals before the end of the year, including a formalwear accessory line, an athletic wear label, and a shoe brand.

On top of that, Andres is the host of Weekend Fix on the Esquire network, and recently launched vegan eatery Fala Bar, which has two locations in Los Angeles, including one on the ultra hip Abbot Kinney Blvd.

In our interview, Andres traces this comeback story to the grit, determination, and drive to be the best that was instilled to him by his immigrant parents. The experience of being a first generation American both sparked his interest in fashion, and has given him an edge that, according to Andres, helps account for much of his success. 

Andres’ fashion tips: what every professional male should have in his wardrobe.

Key Takeaways

• Andres shares the origin of the Five Four name.
• Andres tells us why his nickname is “Pablo,” and why he considers himself more Picasso than Escobar.
• Why Andres’ admires Allen Iverson, and why he feels AI is a bit misunderstood. 
• Why Andres believes that failure is the best force to shape you into the person you need to become.
• How to make your relationship with your business partnership last through the inevitable ups and downs of entrepreneurship. 
• What the experience of having immigrant parents instilled in Andres, and how this mindset has been an asset his entire life.
• Why the feeling you get from dressing well is the key to understanding fashion.
• What we lose from the “anti-fashion” Silicon Valley culture, and why emulating Steve Jobs isn’t always a great idea.
• Andres’ shares his and his business partners’ lowest moment, and how they were able to pivot their model and find success. 

Links

• FiveFour Club 
• Fala Bar
• AndresIzquieta.com
• Weekend Fix
• Views by Drake
• Life of Pablo by Kanye West
• Isse Miyake 
• Allen Iverson

This is episode is brought to you by the snack geniuses at SnackNation.

SnackNation is a healthy office snack delivery service that makes healthy snacking fun, life more productive, and workplaces awesome.

To try a free SnackNation discovery box (featuring 15 delicious snacks your team will love), visit get.snacknation.com/ao. You'll also receive a complimentary copy of the 2016 Ultimate Guide to Creating An Awesome Office.

• Tony shares what it’s like being in business with his two childhood best friends, and why sometime you can’t help someone just by giving them a job.
• How the business evolved from selling stuff online to wholesaling for online retailers.
• How a series of knee surgeries led to a debilitating addiction to pain killers and alcohol.
• How Tony found a renewed purpose after being on the brink of suicide.
• Why leading with a servant heart was so essential to Tony’s recovery.
• The importance of asking for help, and why that’s a part of ShipOffers’ culture.
• Why ShipOffers hires quickly and throws new hires in the mix to see what they can do.
• How Tony freed himself from email.
• How anyone can find their unique ability.

Links

• Entrepreneur Unplugged Podcast

This is episode is brought to you by the snack geniuses at SnackNation.

SnackNation is a healthy office snack delivery service that makes healthy snacking fun, life more productive, and workplaces awesome.

To try a free SnackNation discovery box (featuring 15 delicious snacks your team will love), visit get.snacknation.com/ao. You'll also receive a complimentary copy of the 2016 Ultimate Guide to Creating An Awesome Office.