Jill Barber is President of CYMI Holdings, which serves as the family office for the Mathile Family. Jill joined CYMI in 1999 just prior to the family’s sale of Iams Pet Food Company to Procter & Gamble.

With more than two decades of experience advising three generations of the Mathile family, Jill has become a widely respected voice in the global family office community. 

On today’s episode, we do a deep dive into family offices – how they work, how they evolve, and how they support the needs and legacy of the family.

(0:51) – Where did Jill grow up?

(2:17) – How did Jill find her way into the family office space?

(4:00) – What questions should families ask if they are thinking of setting up a family office?

(8:11) – How should family offices decide which services to build in-house and which to outsource?

(10:46) – How does the family office engage with younger generations of family members?

(13:24) – How do you approach governance in a family office?

(17:14) – How has the family office evolved over the years?

(20:52) – Do family offices have a “culture”?

(23:35) – What are some defining moments during Jill’s career at CYMI?

(25:22) – What questions are top of mind for family offices today?

(28:12) – What is the “why” that drives Jill?

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”?

© 2025 Northern Trust Corporation. Head Office: 50 South La Salle Street, Chicago, IL 60603. Incorporated with limited liability in the U.S. Member FDIC.

“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?

John Onderdonk is a fourth-generation cattle rancher and the head of Northern Trust’s Agricultural Properties Group which manages farm, ranch and timber assets as trustee and executor for Northern Trust clients.

In our episode, John will discuss the growing popularity of ranches among wealthy families and the challenges and opportunities of owing (or inheriting) these assets.

(1:03) – How did John’s family get into cattle ranching?

(3:46) – What role did the ranch play in John’s early years?

(5:02) – How does John help ranch owners in his role at Northern Trust?

(8:29) – What’s driving the growth in ranch ownership?

(11:43) – What challenges should people look out for when they’re either inheriting or looking to buy a ranch?

(14:30) – What are some of the opportunities or innovations that could help ranch owners stay profitable?

(17:13) – How does John build credibility for himself among other ranch owners?

(19:21) – How similar is Yellowstone to the realities of running a ranch?

(21:01) – What does John love—and not love—about running his own ranch?

(23:07) – What is the ‘why’ that motivates John?

© 2025 Northern Trust Corporation. Head Office: 50 South La Salle Street, Chicago, Illinois 60603 U.S.A. Incorporated with limited liability in the U.S. This information is not intended to be and should not be treated as legal, investment, accounting or tax advice and is for informational purposes only. Readers, including professionals, should under no circumstances rely upon this information as a substitute for their own research or for obtaining specific legal, accounting or tax advice from their own counsel. All information discussed herein is current only as of the date appearing in this material and is subject to change at any time without notice. The information contained herein, including any information regarding specific investment products or strategies, is provided for informational and/or illustrative purposes only, and is not intended to be and should not be construed as an offer, solicitation or recommendation with respect to any investment transaction, product or strategy. Past performance is no guarantee of future results. All material has been obtained from sources believed to be reliable, but its accuracy, completeness and interpretation cannot be guaranteed. Farmland investment return data was sourced from Nuveen, “Investing in farmland.”

In 1955, Jane Blain Gilbertson’s parents started Blain’s Farm & Fleet in Janesville, Wisconsin.  Today the business has grown to 45 stores across four states.

Jane shares how over the past 40 years she took over the business from her father, consolidated ownership, welcomed her two daughters into the business, and is now passing the CEO baton to the next generation of leadership.

In our episode, Jane will discuss:
(1:10) – What was Jane’s upbringing like? 

(2:43) – How was Jane first introduced to the family business? 

(5:21) – Was there an expectation for Jane to join the company? 

(7:52) – What was the process of growing within the company and taking on more responsibility like? 

(12:49) – Why are advisory boards so important? 

(15:31) – How did Jane’s daughters come to join the family business? 

(21:35) – What has Jane learned from watching her daughters grow in their roles? 

(24:14) – What are Jane’s thoughts on succession and the future of Blain’s Farm & Fleet? 

(27:05) – What are Jane’s plans now that she’s stepping back from day-to-day operations? 

John Gabbert is founder and chairman of Room & Board, a home furnishings business headquartered in Minneapolis with over 1,100 staff members nationwide.

As a young man, John joined his father's furniture business. In 1980 at the age of 27, John left the family business to start his own furniture company which, over the past forty years, has helped to redefine the industry.

Last year John announced that Room & Board has transitioned to 100% employee ownership through an employee stock ownership plan (ESOP).

In our episode, John will discuss:
(0:52) – What was John’s upbringing like?
(3:09) – How did John get started in the family business?
(5:01) – How did John’s personality start to shape his father’s business?
(7:26) – What was the experience of breaking away from his father’s business to start Room & Board like?
(9:30) – How did John come up with a new direction for Room & Board?
(12:16) – Where did John’s business values come from?
(13:34) – How did Room & Board rethink the traditional furniture business model?
(17:02) – How is John thinking about succession?
(18:25) – Why did John choose the ESOP model? And how did his employees react to the decision?
(21:41) – How does John see his position evolving at Room & Board over the next few years?
(24:15) – Where does John think entrepreneurs go wrong?
(26:43) – What is the ‘why’ that motivates John?

“To be in the restaurant industry, you have to enjoy being on the precipice of great success or total disaster on an almost minute-by-minute basis.” – Rob Mosher

Sarah Grueneberg is Chef and co-owner of Monteverde Restaurant & Pastificio in Chicago, which has been named one of Food & Wine’s “America’s Best Restaurants,” and one of Bon Appetit’s “50 Best New Restaurants”.

Sarah got her start at the iconic Brennan’s of Houston, where she became the restaurant’s youngest female sous chef.  She earned a Michelin Star for three consecutive years during her tenure as Executive Chef of Spiaggia restaurant in Chicago, and a James Beard Award for “Best Chef: Great Lakes.”  Sarah was also a finalist on Bravo’s “Top Chef: Texas”. 

Sarah is joined today by Rob Mosher, Managing Partner at Monteverde.  After graduating from Columbia University, Rob attended the Culinary Institute of America.  Rob’s path first crossed with Sarah while working as a line cook at Spiaggia.  He later became interested in wine, joining Tenzing Wine and Spirits in 2010.  Eventually, Rob teamed back up with Sarah and friends in 2015 to open Monteverde.

You can check out Sarah's cookbook here.

In our episode, Sarah and Rob will discuss:

(1:33) – What was Sarah’s upbringing like?

(3:26) – What lessons did Sarah take from her early career as a chef at Brennan’s?

(6:11) – What inspired Sarah to move to Chicago?

(9:25) – How did Rob’s family life inspire his entrepreneurial spirit?

(10:39) – How did Rob find his way to culinary school?

(13:10) – What were the early years at Spiaggia like for Sarah? 

(17:00) – What motivated Sarah and Rob to open Monteverde? 

(20:28) – How did Rob and Sarah’s paths cross?

(23:29) – What does it really take to run a successful restaurant?

(26:24) – What is the ‘why’ that drives Sarah and Rob to work in such a high-pressure industry?

(30:09) – What separates a home cook from a professional chef?

Today’s episode was recorded live at New Holland Brewing Company in Grand Rapids, Michigan, where we interviewed New Holland Brewing’s founder and CEO, Brett VanderKamp.

Brett graduated college as a Geology major but soon thereafter found his calling in the craft brewing industry and has grown New Holland Brewing into one of the most recognisable independent brewers and distillers in the country.

We discuss a number of topics with Brett today, including his childhood influences, the values that shape New Holland Brewing, and how Brett is cultivating his children’s entrepreneurial spirit.

What we talk about:
2:41 – What was Brett’s upbringing like?
4:39 – What did Brett study at college?
7:00 – How did Brett’s father and grandfather influence his entrepreneurial spirit?
9:43 – How did Brett develop his business’ purpose and values?
11:57 – What are some of Brett’s reflections on the early days of the New Holland Brewing Company?
14:40 – How are Brett’s children getting involved in the business and what are his thoughts on succession?
19:08 – What is the “why” that drives Brett?
20:54 – How has Brett’s geology background helped him think about the future of his business?
22:47 – What challenges lay ahead for brewers?
25:08 – How do you prepare for the big changes in a business (like succession planning)?
28:09 – How can business owners instill their values in the next generation?
30:26 – How can you pivot when presented with a setback?

This month, we will be taking a brief hiatus as we prepare to launch a new podcast series, Secrets of Enterprising Families, airing in November.
In this series, co-hosts Eric Czepyha and Nike Anani will interview experts on the strategies successful families have used to transfer their values, wealth, and legacy to the next generation.
Join us back in November and December for new episodes of The Road to Why.