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:

• (2:01) – How did Sam’s upbringing influence his work ethic?
• (3:15) – How did Sam catch the entrepreneurial bug?
• (5:27) – What did Sam’s parents do to help him on his business journey at the age of 12?
• (7:35) – What was the journey like from Sam’s early business ventures to setting up Claim?
• (10:29) – What problem does Claim solve?
• (13:12) – What’s the long-term opportunity for Claim?
• (14:46) – How does Sam approach team building and leadership?
• (16:09) – What would Sam change if he could turn back the clock?
• (18:06) – What advice does Sam have for entrepreneurs looking to raise capital?
• (21:01) – What insight does Sam have on Gen Z spending habits?
• (23:35) – What kind of impact does Sam want Claim to have on the world?
• (25:56) – What is the why behind Sam's entrepreneurial mindset and work ethic?

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:

• (03:13) - How did growing up on a farm shape Johnson's view on work?
• (06:26) - What differing money stories did Johnson and his co-founder have?
• (08:43) - How did Johnson's entrepreneurial journey start and evolve?
• (11:34) - What mistakes did he make as an entrepreneur?
• (14:38) - Why are some families reluctant to talk about financial education?
• (18:14) - How does Greenlight facilitate family money conversations?
• (21:07) - How does Johnson raise entrepreneurial and appreciative children?
• (24:13) - What is the bigger purpose behind Greenlight?
• (26:07) - What are Johnson's long-term plans for his entrepreneurial journey?

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:

• (2:06) — How did growing up in Silicon Valley influence Pat's entrepreneurial spirit?
• (3:33) — What inspired Pat's early desire to become a venture capitalist?
• (5:07) — What was Pat's journey from college to founding Spindle?
• (7:57) — What problem was Spindle trying to solve and what was the process of selling it to Twitter like?
• (10:16) — What lessons did Pat learn from the sale process with Twitter?
• (12:05) — How did a frustrating notarization experience lead to the founding of Notarize (now Proof)?
• (14:35) — How did Pat and his team navigate regulatory challenges to scale Proof?
• (17:03) — What qualities does Pat believe are important for a CEO leading a pioneering team?
• (19:37) — What common mistakes do young entrepreneurs make?
• (23:51) — What values does Pat want to cultivate in his children as they grow up?
• (26:14) — What drives Pat to continue working hard in his business and personal life?
• (29:08) — What does the future have in store for Pat?

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:

• (2:22) – How did the Kiolbassa Provision Company begin?
• (5:20) – How did Michael find his way into the family business?
• (7:33) – How did Michael’s experience as a credit analyst help him find his footing in the company?
• (9:55) – How did the company evolve when Michael came on board?
• (13:41) – What did Michael do to address the challenges facing the business
• (16:21) - What values are important to Michael both in business and personally?
• (19:01) – What is Michael doing to prepare the company for the next generation?
• (22:11) – What advice does Michael have for young entrepreneurs?

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:

• (1:52) - How did John's childhood help shape him into the person he is today?
• (2:52) – What were some important lessons John learned from his parents?
• (6:28) – What were some of John’s childhood business ventures?
• (8:28) – What does John think entrepreneurs get wrong
• (10:01) – Why isn’t John a big believer in five-year plans
• (11:36) – What’s John’s number 1 rule about phone calls?
• (13:05) - What does he look for when interviewing people to join his team?
• (16:39) – How is John helping to cultivate the entrepreneurial spirit within his own children?
• (19:19) – How did John’s children get involved with the family business?
• (21:20) - Why is hiring family so important to John?
• (22:51) – What does John mean when he says he provides veto power to his family?
• (25:19) – How do John and his wife, Deanna, manage their professional and personal lives alongside their entrepreneurial spirits?
• (27:15) – what is the ‘why’ that motivates John?
• (28:41) – What are John’s top tips for hosting memorable dinner parties?

So many of our clients ask us the age-old question, “How much is enough?”

• How much of my wealth should I give to my children?
• At what age should I share my estate plan with my family?
• How do I prepare my children for the responsibility of the wealth they will inherit?

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:

• (2:48) - What makes Northern Trust qualified to write the book on wealth?
• (5:30) – How can the secrets in this book impact how families approach their wealth planning
• (7:20) – How can the book help to answer some of the tough questions that families have concerning wealth and legacy?
• (9:01) – What does Pam’s money story look like?
• (11:22) – What do we mean by the term ‘enterprising’? And why is it something that a family might aspire to be?
• (14:25) - What are some of the questions that this book helps to answer?
• (17:46) - Why is it important for families to define what wealth means to them?
• (21:17) – Have there ever been any objections from families that have tried to implement some of the secrets in the book?
• (24:47) – Why is the book structured the way it is?
• (26:45) - Are the insights in the book mainly for the older generation who created the wealth? Or are they also relevant for younger generations?
• (28:47) – Has Pam implemented any of the secrets from the book with her own family?
• (31:45) – What is Pam’s ‘why’?