What’s the worst that could happen? For Rob Katz and Kevin Boehm, a four-hour conversation over coffee turned that question into the beginning of Boka Restaurant Group.

This week, Rachel and Jeana welcome restaurateur Rob Katz for his first podcast interview—and a candid, funny conversation about taking chances, building trust, and making people feel seen. From arriving in Chicago with $1,200 to discovering hospitality during an unexpected bartending shift, Rob shares how relationships shaped his path and why a lasting business partnership starts with complementary strengths.

We talk about why the customer isn’t always right, how Rob maintains close friendships without social media, and the unexpected joy of finding a new crew later in life. Plus: raising thoughtful, hardworking kids, asking questions even when you feel inexperienced, and a few memorable encounters with very famous restaurant guests.

Before the interview, Rachel and Jeana reflect on the risks that changed their own lives. Afterward, Jeana brings The Five Star Weekend to show-and-tell, sparking a conversation about girls’ trips, blending friend groups, and remembering who you’re there to support.

Media:

• Rob Katz’s official bio
• Boka Restaurant Group
• Gingie — the restaurant Rob specifically invites listeners to visit.

• The Five Star Weekend on Peacock
• The Five-Star Weekend by Elin Hilderbrand — the book behind the adaptation.

A diploma doesn’t come with instructions for making friends, navigating workplace expectations, or walking into a room full of strangers. So where do we learn those things?

This week, Rachel and Jeana welcome Heather Redisch, creator of Adulting 101 Masterclass, for a conversation about building confidence and connection through the everyday experiences that stretch us. Heather shares what she’s learning from coaching Gen Z, why managers should say the unwritten rules out loud, and how parents can help their kids build independence without smoothing away every challenge.

We talk about giving yourself time to settle into a new city or job, why one meaningful connection makes a networking event worthwhile, and how small, uncomfortable moments become opportunities to grow. Plus, Rachel and Jeana reflect on advice they’d give their younger selves—and share why ordinary errands are better with friends and putting our phones away can help us be more present.

Whether you’re starting your adult life, raising someone who is, or navigating a transition of your own, this episode is a reminder that you don’t have to have everything figured out to take the next step.

Media mentioned in this episode:

• Adulting 101 Masterclass
• Heather's Instagram: @adulting101_masterclass
• Heather's Adulting 101 Masterclass podcast
• the book Anxious Generation
• Priya Parker's new book, The Art of Fighting
• Everything is better together - The American Time Use Survey
• The University of Chicago's Train Study
• Read Phoebe Bridgers' phone-free event policy here

What’s the difference between collecting contacts and building real relationships?

Award-winning communications executive—and lifelong super-connector—Jon Harris joins us to share what more than three decades of bringing people together has taught him about curiosity, generosity and the relationships that remain long after jobs and titles change.

Jon opens up about the difficult childhood that shaped his commitment to helping others, why he believes the best networkers give without keeping score and what he has learned about asking for help during a professional transition of his own. He also introduces us to the Truffle Club, the trusted community of communications leaders he created during the pandemic, and reminds us why we should never let someone’s title stop us from saying hello.

Plus, Jeana and Rachel debate the increasingly popular wedding-day Irish goodbye and reflect on Dolly Parton’s legacy of generosity, joy and making the world a little brighter.

This episode is sponsored by Eventually. Visit eventuallyticketing.com/the-connection-code and use code CONNECT10 for 10% off your first year.

Media:

• Jon Harris: LinkedIn and Instagram @jonjayharris

• Dolly Parton’s Imagination Library: Learn about the book-gifting program
• Coyote vs. Acme: Official movie site and trailer
• Dare to Serve by Cheryl Bachelder here
• SocialWorks: Chance the Rapper’s Chicago nonprofit