“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.

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?