Brenda Smola-Foti and Frank Foti are co-founders of The Ground in Willamette Valley, Oregon.
The Ground is a place that almost defies definition – it is a regenerative agriculture farm, but also includes an Inn and Farmhouse where guests can stay, a restaurant, and a farm store. Frank and Brenda host workshops, nature tours, group retreats, guided meditations and a lot more.
The Ground may be different things for different people, but it is tied together by a cohesive set of values that are important to Brenda and Frank, including connection, humility and caring for our planet.
(1:06) – What was Brenda’s upbringing like?
(3:43) – What drove Brenda to go from fashion to farming?
(5:03) – How did Frank find his way into the family business?
(9:34) – What experiences led to Frank joining The Ground?
(11:46) – Why is the theme of connection important to Frank?
(12:30) – What were some of the early issues Brenda and Frank faced while establishing The Ground?
(15:50) – What exactly is The Ground?
(16:45) – How do all the facets of The Ground work together?
(19:26) – How do Brenda and Frank divide and tackle their tasks?
(21:54) – What is Brenda’s “why”?
(22:48) – What is Frank’s “why”?
(24:47) – How are Brenda and Frank thinking about succession?
© 2025 Northern Trust Corporation. Head Office: 50 South La Salle Street, Chicago, IL 60603. Incorporated with limited liability in the U.S. Member FDIC.
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 CEO 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.
Our guest today is on a mission to revolutionize the advertising industry and the way Gen Z spends money and spends time with one another.
Sam Obletz is the co-founder of Claim, which he launched with his classmate Tap Stephenson while at Harvard Business School.
The Claim app seeks to build a new way for friends to connect and for brands to reward their customers. This is done not with more screen time, likes and reposts, but through fostering authentic, in-person connections and experiences among peers around a brand.
And investors have taken notice, including the venture capital firm Sequoia Capital which announced its partnership with Claim last year.
In today’s episode, Sam will dive into Claim and share his insights on entrepreneurship, raising capital, and generational attitudes towards spending, among other topics.
In the episode we will learn:
What if your business could be owned by its own purpose?
In today’s episode, our guests discuss the emerging trend of business owners transferring ownership of their business to a purpose trust. Many business owners have begun to explore this alternative ownership structure as a means of preserving the values of their business, and ensuring that their business is not sold, long after the business owner is no longer around.
Natalie Reitman-White is the principal at Purpose Owned, a consultancy for ownership succession planning. In 2018, Natalie pioneered one of the first purpose trust ownership transitions in the U.S. with Organically Grown Company.
Ari Weinzweig is co-founder of Zingerman's Community of Businesses, which consists of various food-related companies including Zingerman’s Deli in Ann Arbor, Michigan. In 2022, with the help of Natalie, Ari and his business partner transitioned ownership of the Zingerman’s brand to a purpose trust.
In the episode we will learn:
(4:21) – What was the road to Zingerman’s like for Ari?
(7:08) – How did Natalie find her way to Organically Grown?
(10:02) – What interested Natalie and Ari in Perpetual Purpose Trusts?
(17:73) – Why was preserving the legacy of Zingerman’s important to Ari?
(21:32) – How can a business owner generate liquidity when they transfer their business to a Perpetual Purpose Trust?
(26:50) – Can Perpetual Purpose Trusts adapt to changing circumstances?
(29:24) – Who can sit on a trust committee?
(31:49) – What is the process and cost of transferring to a Perpetual Purpose Trust structure like?
(34:20) – Where can business owners start if they want to adopt a Perpetual Purpose Trust structure?
(36:51) – What is the ‘why’ that drives Natalie and Ari?
How do families talk about money together? They usually don’t.
But talking about financial matters with family does not have to be awkward or taboo. In fact, finding small opportunities to discuss money with your kids can build a foundation for having bigger conversations about the family’s wealth and estate plan.
As co-founder of Greenlight, Johnson Cook is helping to build this foundation for millions of Americans. Greenlight is a financial education app and debit card for kids and teens that allows parents to instantly send their kids money, set up chores and allowance, create savings goals, and more.
In today’s episode, Johnson shares his own entrepreneurial journey, as well as insights on how we can empower parents and kids with the tools to learn about, and talk about, money together.
In the episode we will learn:
Pat Kinsel likes to solve big problems. As founder and CEO of Proof, formerly known as Notarize, Pat created the first company that made it possible to legally notarize documents online.
Before Proof, Pat co-founded the technology start-up Spindle, which was acquired by Twitter in 2013. He was also a partner in the venture capital firm Polaris Partners where he helped build companies such as Drizly which was acquired by Uber.
In this episode, Pat shares insights for entrepreneurs young and old on building a company that “stands the test of time”.
In the episode we will learn:
Michael Kiolbassa is CEO of San Antonio-based Kiolbassa Provision Company which was started by his grandfather 75 years ago.
The company makes hand-crafted smoked sausages and bacon and has become the #2 beef sausage brand in the U.S. But the road has not been easy. In fact, each generation has had to reinvent the business in their own way to keep it moving forward.
Michael shares some of the principles and strategies that he and his family have adopted over the years which, in our experience, are common among successful enterprising families.
In the episode we will learn:
John Oppenheimer is the founder and chairman of Seattle-based Columbia Hospitality, which manages over 100 properties across the U.S., including hotels, resorts, golf courses, residential communities and event venues.
In addition to launching Columbia Hospitality in 1995, John has also founded five other successful, hospitality-related businesses.
In this episode, John discusses a broad range of topics from his book, Keys to the Room, including business insights, advice for young entrepreneurs, and how to “let your children be the teachers,” as John puts it.
In the episode we will learn:
So many of our clients ask us the age-old question, “How much is enough?”
Our guests on today’s podcast have spent the better part of their careers answering these questions. Steve Fradkin is President of Wealth Management at Northern Trust.
Pam Lucina lead’s Northern Trust’s Trust & Advisory Practice and is President of The Northern Trust Institute.
Steve and Pam discuss a new book that the Northern Trust Institute recently published titled “Secrets of Enterprising Families” which answers these questions of intergenerational wealth transfer along with many others which we will cover during our discussion.
In this episode you will learn:
This month, we'll be taking a brief hiatus to prepare for Season 2 of The Road to Why.
But we'll be back next month with more stories from business owners and entrepreneurs as they discuss their perspectives on business, family, wealth, and legacy.
So stay tuned for new episodes of The Road to Why, coming March 2024.
We'll see you then.
Abdur Chowdhury is a life-long entrepreneur. Early in his career, he rose through the ranks to become AOL’s Chief Architect. Abdur then went on to co-found Summize, a start-up where he pioneered a way to organize real-time opinions on the internet (and for which the BBC has dubbed him “the father of trending”). In 2008 Abdur merged Summize with another start-up by the name of Twitter and became Twitter’s first Chief Scientist.
Abdur holds over 50 patents and has launched more than 25 commercial products. Currently, he is CEO and co-founder of Aura Frames which specializes in digital photo frames that allow families to share pictures from anywhere.
In this episode, Abdur discusses his journey as an entrepreneur and provides tips for entrepreneurs starting out on their own journey.
In the episode we will learn: