The Road to 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:(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'?

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?

Scott O'Neil is one of the most innovative executives in the entertainment and sports industries.  As CEO of Harris Blitzer Sports & Entertainment, Scott oversaw the company's portfolio including the Philadelphia 76ers and the New Jersey Devils.  Scott has also served as President of Madison Square Garden and was Alternate Governor for the NBA and NHL for over a decade.Last year Scott made a significant career change, moving to London to become the CEO of Merlin Entertainments, the world's second-largest visitor attraction operator, overseeing attractions such as Madame Tussauds, The London Eye, and LEGOLAND.In this episode, Scott shares some of the principles he lives by both at home and at the office and how he and his wife are instilling those values in the next generation.Learn more about Scott's story in his book Be Where Your Feet Are.We'll also find out: (2:08) – How did Scott's upbringing shape the person he is today?(8:44) – How did culture and innovation fuel the success of Harris Blitzer Sports & Entertainment?(9:55) – How did the 76ers turn struggle into success during Scott's tenure?(13:40) – How do Scott and his wife instil values in their three daughters?(15:30) – Why does Scott view failure as a good thing?(19:34) – Why is it important to “assume positive intent” in business and in life? (21:12) – What is Scott's “WMI”?(22:34) – Why does Scott believe it is important to “ruthlessly prioritize”?(24:17) – What impact did Scott's mentor, the late NBA Commissioner David Stern, have on his life?

In 1999, Tiffany Taylor and Leon Chen started a business delivering hot-from-the-oven cookies out of Leon's college apartment in Austin, Texas. Today, Tiff's Treats has 90 stores across the U.S., 1,800 employees and continues to grow. But their road to success wasn't exactly easy. In this episode, Tiffany and Leon discuss the challenges they encountered as they built Tiff's Treats over the past 20 years, the importance of embracing failure as a tool for growing your business, and insights into teaching your children about hard work and perseverance. Learn more about Tiffany and Leon's story in their bestselling book It's Not Just Cookies.  We'll also find out: (1:50) – How did Tiff's Treats start? (5:16) - What were some of the failures Tiff and Leon encountered (and learned from) along the way to success? (7:07) - Why is it important to be open about your failures as well as successes? (8:16) - How did Tiff and Leon's upbringings shape their career paths? (10:09) - What are some of the values Tiff and Leon want to impart to their children? (11:34) – What are Tiff and Leon's core family values? (15:51) – Why were Tiff and Leon initially hesitant about appointing a board of directors and how has their board helped them grow? (18:20) – What are Tiff and Leon's thoughts about life after Tiff's Treats? (21:04) -  What is the ‘why' that motivates Tiff and Leon to put the hard work into their business? (23:32) – What's it like being in business with your spouse, and how do they deal with conflict successfully? (26:16) – What advice do Tiff and Leon have for young entrepreneurs starting out on their own business journey? (28:30) – What inspired Tiff and Leon to write their book, It's Not Just Cookies?

Twenty years ago, entrepreneurs Vanessa Troyer and Chris Farentinos founded Architectural Mailboxes on the conviction that a small online company by the name of Amazon would one day deliver packages to doorsteps across America. In this episode, Vanessa and Chris share how they built their business and redefined their industry through creativity and grit, their decision to sell the business after two decades of growth, raising grounded and motivated children, and using the sale proceeds to create a legacy for future generations, among other topics.We'll also find out:(1:49) - What inspired Chris and Vanessa's parcel receptacle idea? (2:57) - How did Chris and Vanessa begin creating a design for their parcel receptacle, and how did the design evolve? (4:47) - How did the transformation and evolution of online shopping impact the design and creation of the Oasis product line? (5:48) - How did Vanessa formulate a plan to scale the business, and how did they connect with the market's leading vendors? (12:29) - How did Chris and Vanessa's partnership play into the company's dynamic, and what were the challenges and benefits of running the business as a couple? (16:02) - What ultimately provoked Chris and Vanessa's decision to sell their company, and how did they prepare an exit strategy? (20:19) - What advice would Chris and Vanessa give to business owners contemplating the sale of their company? (21:42) - What have Vanessa and Chris been working on since the sale of the business? (24:54) - As business owners, how were Vanessa and Chris able to approach having a conversation with their children about money, work, and pursuing their passions? (27:53) - How did Vanessa and Chris find their passion in building mailboxes, and what did they gain personally from the work? (29:49) - What does 'legacy' mean to Vanessa and Chris, and how have they created a lasting impact through their business? 

As President of Nickelodeon, Gerry Laybourne turned a tiny children's network into a multi-billion dollar television empire. Later in her career, Gerry was inspired to co-found a new network for women, Oxygen Media. Join us on the season premiere of The Road to Why, where we learn how understanding the perspectives of the younger generation helped to shape the trajectory of an entire industry.  Gerry speaks about her innovative approach to leadership at Nickelodeon, raising entrepreneurial children, and giving kids a voice in family discussions on wealth and philanthropy. She also discusses her “joyous work-life imbalance,” being a female senior executive in the 1980s, and her current focus as co-founder of Day One Early Learning Community, among other topics. We'll also find out: (2:56) — What were some of the key influences in Gerry's upbringing that helped shape her values?(5:10) — How influential was early television on Gerry's career?(6:09) — What led Gerry to work in television?(12:02) — How did Gerry change the culture at Nickelodeon?(14:08) — How did Gerry create programming that kids of the '80s could relate to?(15:47) — How did Gerry's partnership with Oprah develop?(20:19) — How did Gerry's career influence the professional lives of her children?(23:45) — What drives Gerry to build, create and inspire others?(25:52) — What was Gerry's experience in the television industry as a woman in the '80s?(27:54) — What are ‘Global Women's Mentoring Walks,' and how did Gerry found the initiative?(29:52) — How did Gerry make the transition from children's television to children's education?(32:40) — In Gerry's view, what makes a good board member?(34:55) — How does Gerry approach conversations on wealth and legacy with her children?

Join our host, Eric Czepyha, Director of Business Services at Northern Trust, as he speaks with business owners, entrepreneurs and visionaries about business, family, wealth and legacy and shares advice and life lessons from those who have found success in ways expected and unexpected.Coming soon.