Nadia Rawlinson and Michael Alter are co-owners of the WNBA team, the Chicago Sky.

Nadia was the Chief People Officer at Slack Technologies when the company was acquired by Salesforce in 2021 for $28 billion. She is an advisor for Google Ventures, serves on the Stanford University Board of Trustees and is on the Board of Directors for J. Crew and Vail Resorts.

Michael is President of the Alter Group, which was founded by his father and has become one of the largest private commercial real estate developers in the country. He is also the founder and a board member of the non-profit organization City Year Chicago.

In today’s conversation, we will learn:

(1:05) – What were Michael and Nadia’s formative years like?

(4:16) – How and why did Michael join the family business (Alter Group)?

(8:39) – How did Nadia define her career path after the Slack acquisition?

(12:23) – What makes for a good board member?

(15:12) – What do entrepreneurs get wrong when building a business?

(16:43) – Why did Michael decide to buy Chicago Sky?

(21:08) – What does being a good “steward” of the Chicago Sky mean to Nadia?

(24:35) – How does the organizational structure of a sports franchise work?

(29:01) – What life lessons have Nadia and Michael brought home from Chicago Sky?

(33:15) – What are Michael and Nadia’s “why’s”?

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“I think when a lot of business leaders hear me talk about play and fun, they think well, of course you would do that, you're a toy company. But I think it's so important that every culture, every team, every organization has play incorporated into their culture.”

Robert Pasin is Chief Wagon Officer (otherwise known as CEO) of Radio Flyer.

Robert’s grandfather, an Italian immigrant, started the company out of his garage in 1917, and over the past 100 years and three generations of leadership, Radio Flyer has become an iconic American brand.

Today we’ll hear Robert’s story, including how he revived the brand and built a thriving culture at Radio Flyer.

(0:47) – What was Robert’s upbringing like?

(2:09) – How did a tour of his father’s factory change everything?

(5:13) – How did Robert’s grandfather start the business over a century ago?

(7:45) – Did Robert’s father expect him to take over the family business one day?

(9:37) – What does Robert do to balance continuity with innovation at Radio Flyer?

(12:38) – How does Robert bring in fresh perspectives and ideas?

(15:02) – Why is culture so important to Robert? And how does he build a good culture?

(18:49) – Why is play important?

(20:24) – How is Robert talking about succession with his own kids?

(22:49) – What is Robert’s ”why”?

“And that's when this flood of clarity came in, and I was like, I'm going to use chocolate as a medium for storytelling.”

Katrina Markoff is founder of the Chicago-based Violet Flame Chocolate.

Prior to her new venture, Katrina founded Vosges Haut-Chocolat in 1998, which expanded our understanding of what chocolate could be.

Katrina has been named one of Fortune Magazine’s “40 Under 40”, Bon Appétit has named her Food Artisan of the Year, and Food & Wine has called her “the innovator in chocolate to lead the U.S. through the next 30 years.”

We follow Katrina’s journey from pre-med student at Vanderbilt, to attending culinary school in Paris, to working at El Bulli (one of the best restaurants in the world), and finally finding her calling as an entrepreneur and chocolatier.

(1:06) – What was Katrina’s upbringing like?

(4:30) – How did Katrina make the change from pre-med student to culinary school?

(9:13) – What was Katrina’s experience working at El Bulli with Ferran Adrià like?

(12:47) – What attracted Katrina to working as a chocolatier and founding Vosges Chocolat?

(16:40) – What led to Vosges’ huge success?

(19:13) – Why did Katrina start Violet Flame Chocolate, and what is she doing differently this time around?

(23:03) – What is the “why” that drives Katrina?

(24:46) – What do entrepreneurs get wrong when they first start out?

(26:20) – Why is failure important?

(27:51) – What’s the best way to enjoy chocolate?