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’?

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:

• (2:33) — When did Abdur’s passion for computers begin?
• (4:40) — How did Abdur find his way into cave diving?
• (6:59) — What was Abdur’s transition from education to the workplace like?
• (8:00) — Why did Abdur leave the world of academia for a professional role in the tech industry?
• (10:00) — What makes a good entrepreneur?
• (12:20) — How does Abdur support and inspire his daughter to find her own path in life?
• (14:20) — What prompted Abdur to start his own school?
• (16:58) — How did Abdur become the “Father of Trending”?
• (20:36) — After merging his company with Twitter and becoming its chief scientist, what came next for Abdur?
• (23:01) — What is the ‘Why’ that drives Abdur to pursue a life as an entrepreneur?
• (24:23) — How does Abdur feed his need to learn?

At the age of three, Ed Hajim was kidnapped by his father, driven cross-country, and told his mother had died.  As his father tried to find work overseas during the Great Depression, Ed spent his childhood in a string of foster homes and orphanages.

Despite these dire circumstances, Ed earned a scholarship to attend the University of Rochester, served in the U.S. Navy, graduated from Harvard Business School and went on to build an extraordinary career on Wall Street.  As a philanthropist, Ed has supported numerous charitable organizations through his family foundation.

In today’s episode, Ed shares his story and life lessons, which you can read much more about in two books he recently published: On the Road Less Traveled and The Island of the Four P’s – a Modern Fable about Preparing for Your Future.

In the episode we will learn:

• (2:13) – Where does Ed’s story begin?
• (6:06) – What does Ed remember about his father’s relationship with him and wealth?
• (8:10) – How important is education to Ed?
• (10:25) – What interested Ed in the financial services industry?
• (13:47) – What, beyond his analytical ability, was the key to Ed’s success in the financial services industry?
• (15:44) – What does Ed mean when he says ‘You should never start anything from scratch’?
• (17:55) – What are some life lessons that Ed has for parents raising children from a position of wealth?
• (21:12) – Why is family so important to Ed?
• (22:44) – What is the “Why” that drives Ed?
• (25:27) – What did Ed find out about his family from a forgotten suitcase of letters?
• (28:24) – How does Ed feel his childhood affected him?
• (29:49) – What does Ed believe to be the four pillars of success in life?

Nikè Anani is the Director of Next Gen Advisory at Northern Trust. She grew up in an enterprising family in Nigeria, where her father, a self-made entrepreneur, founded and ran their family business.   At the age of nine, Nikè relocated to the United Kingdom with her mother and two siblings in search of a better life as her father remained in Nigeria to run the family business.  Sixteen years later, Nikè returned to Nigeria where she learned that her father’s “family business” had grown significantly over the years into a large-scale business enterprise. 

In this episode, Nikè shares how her experience shadowing her father, and ultimately running his family office, shaped her decision to devote her career to helping the next generation of wealth inheritors realize their potential.

What we discuss:

• (2:00) – What was Nikè’s upbringing like?
• (4:09) – What was it like moving from Nigeria to the UK?
• (5:31) – How was life for Nikè in the UK until she moved back to Nigeria?
• (8:18) – How did Nikè transition to working in her father’s business?
• (10:34) – How did Nikè’s involvement in the family business affect her relationship with her siblings?
• (13:07) – What are some of the challenges of being part of a family-owned business?
• (15:11) – If Nikè could go back in time, what would she like to have done differently during her on-boarding to the family business?
• (17:19) – What are some effective strategies for transitioning wealth or business ownership from one generation to the next?
• (20:17) – Why can there sometimes be hesitancy towards having conversations about wealth and legacy between generations?
• (22:10) – What is the difference between the next-gen and the rising-gen?
• (24:27) – Why is it important for the next-gen to form peer groups and communities?
• (26:47) – What is the ‘why’ that drives Nikè?
• (27:23) – What does Nikè’s father think of her new role?
• (28:43) – How have Nikè’s life experiences and her role with Northern Trust influenced the way she teaches her own children about wealth?

Brian Adam is the owner and President of Milwaukee-based Olympus Group, a 120-year-old company that started as an American flag manufacturer and over the years has expanded to become a world-class custom printing business and the largest mascot manufacturer in the U.S.

In this episode, Brian shares how his father bought Olympus when it was on the brink of bankruptcy and later sold the company to Brian. Under Brian’s leadership, Olympus Group has continued to grow, and along the way Brian has built a framework with his father and brother for working together to expand the family’s investments into other start-up businesses in the spirit of building a “family enterprise”.

Learn more in the book that Brian co-wrote with Dave Fellman, Rules Of Engagement: A Guide To Better Communication And Better Relationships With Everyone Who Is Important To Your Business.

In the episode we will learn:

• (2:09) - How did Brian get started with Olympus Group?
• (3:56) – What did the deal between Brian and his father for the company look like?
• (6:44) – How did the sale of the business play into the family’s overall wealth strategy?
• (8:14) – What shaped Brian’s advisory board?
• (9:51) – What kind of people are on Brian’s advisory board?
• (11:17) – What is the why that keeps Brian working hard at Olympus Group?
• (13:53) - How does Brian incentivize his workforce?
• (16:37) – What are some key takeaways from Brian’s book, ‘Rules of Engagement’?
• (18:39) – What are the core values Brian is trying to instill in his own children?
• (20:53) – How did Brian get into the mascot manufacturing game?
• (22:50) – What was Brian’s first mascot-related claim to fame?
• (25:06) – What advice does Brian have for any young entrepreneurs listening?
• (27:28) – How do you cultivate a healthy work culture?