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Intentional Integrity | Business with Purpose Podcast EP 221: Rob Chesnut

Intentional Integrity | Business with Purpose Podcast EP 221: Rob Chesnut

Intentional Integrity | Business with Purpose Podcast EP 221: Rob Chesnut

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  • Intentional Integrity | Business with Purpose Podcast EP 221: Rob Chesnut
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I think we can all agree that creating a culture of integrity in our workplaces in important. We want to be able to trust the people we work for and work with. We want to know that the company we are representing as an employee or as an owner is one that people can trust; that the brand has a certain amount of ethics behind it. That doesn’t just have to be regarding just manufacturing, but the fact that a company strives to have integrity on the whole. My guest today is creating and leading a revolution of ethical companies that hold integrity as a top priority. Rob Chesnut if the former Chief Ethics Officer for Air B&B, and the author of the new book, Intentional Integrity: How Smart Companies Can Lead An Ethical Revolution. Rob is a graduate of Harvard Law School and The University of Virginia. He worked for 14 years with the US Justice Department, where he prosecuted bank robberies, kidnapping, murder, and espionage cases. He joined eBay in 1999 as the company’s third lawyer where he led eBay’s North American legal team and later founded its Trust and Safety Team. Rob subsequently spent six years as the general counsel and first attorney and digital education leader, Chegg, where he helped take the company public in 2013. He joined Air B&B as general counsel in 2016, where he grew the legal team from 30 to over 150 legal professionals in 20 offices around the world. His team led initiatives to promote home sharing and address regulatory issues with local governments and landlords around the world. As Chief Ethics Officer, Rob developed a popular interactive employee program, Integrity Belongs Here, to help drive ethics throughout the company. He lives in San Francisco, and his website is intentionalintegrity.com. I will tell you that this was a fansicnating conversation. Rob has so much experience and knowledge and is the type of person I’d love to sit down with for dinner and ask 7 million questions. I asked him about half of those here today. 😉 You are going to absolutely love this conversation with Rob Chesnut! 

5:58 – The Rob 101 

  • Rob is an author, tech general counsel, and has been a federal prosecutor. He enjoys the idea of variety and being tough to label! He started his career as a lawyer in Virginia. After some time in that role, he felt like he was presiding over a lot of negativity. He started to feel pulled to do something positive and uplifting. He believes business has the power to transform the world in a positive way, even more than government, which is often pulled apart by partisan politics. 
  • Rob started looking for companies doing good things in the world. While working as a prosecutor in northern Virginia, he received calls from other prosecutors wanting records about a company called America Online (AOL). (This is when you still received a disk and needed dial up for the internet). 😉 It struck Rob that the internet may have staying power, and he started using a few sights like eBay. 
  • Most companies at that time did not need (or didn’t think they needed) a federal prosecutor, but Rob contacted eBay regarding the potential problems they might run into with illegal items, fraud, regulations, and more. eBay called Rob back the next day. He was asked to start eBay’s “Trust and Safety” department and Rob grew the team to more than 2,000 employees who helped maintain order and prevented fraud on the site. 
  • Later in his career Rob moved onto Chegg and then Air B&B. Air B&B is in the Trust business. There need to be rules and order so that people can connect over their common interests. That has been a theme throughout Rob’s career. 

9:00 – Intentional Integrity 

  • While Rob was the general counsel at Air B&B, it really struck him that the world was changing. Everywhere he turned, Rob saw companies in trouble and being called out for bad behavior. At that time, the level of feedback and public criticism was really something new. People want leaders and companies to step up. 
  • Rob sat down with Air B&B founder, Brian Chesky to talk about how to drive integrity into the culture of a company. They had no idea how to start, but both agreed they needed to try it. They started developing a program that encouraged Air B&B employees to treat each other with integrity, and the employees truly embraced the program.
  • Rob’s wife, who works in publishing started (strongly) encouraging him to write a book about it. No one else was doing it at the time and she knew it was important for the world. Rob, however, was not at all interested in writing a book. Rob’s wife convinced him by offering to find a co-writer and a major publisher. 
  • Rob thought he had all the knowledge on the subject, but the more he engaged with the writing process, the more he realized he still had a lot to learn. Rob discovered the writing was really a journey of knowledge. The book is called Intentional Integrity: How Smart Companies Can Lead An Ethical Revolution. It includes a wide range of perspectives from well-known artists and industry professionals. 

13:19 – A Major Shift

  • The Internet and social media have truly changed how we interact with brands and organizations. We seem to be on the cusp of an ethical revolution. Up until even just a few years ago, most companies operated under a mantra of “shareholder value.” Anything was ok as long as it increases shareholder value. 
  • Shareholder value worked for a few decades, but parts of it did not work. It did increase short-term focus but may have hurt the planet in the long run, used slave labor in other parts of the world, and not offered employees health benefits. The world started to realize the mantra was also causing problems and was no longer working.
  • Shareholder value is now being rejected as the way companies should operate. It’s been replaced with stakeholder principles. Now companies need to operate with the best interest of all of its stakeholders. Air B&B must consider not only its investors, but their employees, guests, hosts, and the communities where it operates. Companies are beginning to realize they have a broader obligation to do good in the world. 
  • The key is to think about it holistically across all stakeholders. It should not be all about profit, but profit is important for companies to be able to fulfill their purpose. When a company is perceived to be operating ethically with its business model, with the way that it treats people, it actually outperforms the market and outperforms competitors. It’s not a tradeoff. It gives companies that operate this way a wind in their back. It helps them operate and be more successful as a business. 
  • Employees are holding their own companies accountable and customers are jumping in as well. They both care about where their money is going. If they feel a company is not ethical, they’ll move their money elsewhere and they’ll share on social media to spread the word about unethical practices. Government will jump in too if they see consumers feeling this way.

23:51 – Leveraging the “6 Cs”

  • Rob talks about leveraging the 6 Cs to foster and manage a culture of integrity at work. The first is for “CEO.” You can talk about integrity all you want, but your CEO has to be following that and setting an example. All things are possible if the CEO is on board. 
  • The second C is for a “Code of Conduct.” Having a Code of Conduct isn’t enough. Any company can do that and follow compliance rules. It must be intentionally created with values that reflect what the company is about, and clearly communicated and followed with appropriate channels for feedback and transparency. 
  • The third C is to “Communicate Your Code.” It’s important to proactively prepare and have the message communicated from the top. Consequences are necessary for when rules are violated. Rules must apply to everyone, from the bottom to the top. There must be a clear reporting structure with fair consequences. 
  • Stay tuned to hear more about the 6 Cs and intriguing examples of how they relate to human behavior! 

49:05 – Getting To Know Our Guest

  • Find out what song Rob has to sing along to when he hears it, someone who has really impacted him with the way he approaches business, what his favorite TV show was growing up, and more! Be sure to stay tuned to hear Rob’s answer to our all important question of what it means to him to run a business with purpose.

Memorable Quotes

8:45 – “I think that’s been a theme throughout my career. Trying to promote good in people and promote human connections through providing a little bit of structure and order to enable the best behavior.” 

10:37 – “Where you work is such a reflection of who you are. The brands of the companies where you work become your brands…I think we all want to be proud of where we work. We want to feel as though we are a part of something that is doing good in the world.” 

16:20 – “The world started to realize that ‘shareholder value’ mantra was causing a lot of ethical corner to be cut, and it wasn’t working. Not that shareholders aren’t important, but why should shareholder thing be the only thing that matters?”

17:35 – “Why shouldn’t a company also be thinking about what’s good for the broader communities where it operates? And I think that part of this revolution is an understanding that we need companies to think and act differently, and I’m glad that companies are embracing this new idea of stakeholder principle. 

18:51 – “You need a purpose as a company. Profit is not purpose. I think you need a ‘North Star’ to kind of guide your actions. I think you have to be solving a problem in the world or doing something good for the world. I actually think profit is critical. Profit is what funds your ability to accomplish your purpose.”

~19:45 – When a company is perceived to be operating ethically with its business model, with the way that it treats people, it actually outperforms the market and outperforms competitors. It’s not a tradeoff. It gives companies that operate this way a wind in their back. It helps them operate and be more successful as a business.”

~23:45 – “You can’t operate as a 20th century company in the 21st century.” 

Thank you to our partners of the show:

Ammas Umma 

Did you know I have an ethical brand directory? That’s what Chelsea used to start finding products for her boutique almost four years ago! Now, Amma’s Umma carries over 50 intentionally sourced brands and is the perfect one stop shop for all your gift giving needs. As a thank you to the Still Being Molly community, she is offering 20% off with code SHOPWITHMOLLY. Head to shopwithmolly.com for all the details.

GOEX

At GOEX, we believe in the power of purchase. We use a simple t-shirt to connect our customers with their apparel makers. GOEX customers sustain fair wage jobs that liberate workers from poverty and empower them in their families and communities. We are proud to be a verified member of the Fair Trade Federation. Shop sustainable, eco-friendly t-shirts and sweatshirts with purpose today at goexapparel.com.

Simple Switch

I want to introduce you all to a company I believe in that helps you more conveniently purchase with purpose, SimpleSwitch.org

Simple Switch is an online marketplace for ethical and impactful shopping. They let you shop online for more than 3,000 products ranging from everyday essentials like toilet paper and hand sanitizer, to special gifts like journals or jewelry. Every product has a positive environmental or social impact, like planting trees or fighting human trafficking.

Simple Switch is offering a discount exclusively for our listeners. Check out the marketplace on simpleswitch.org and get 20% off your first order with code PURCHASEWITHPURPOSE at checkout!

The Lemonade Boutique 

This episode is sponsored by The Lemonade Boutique, a women’s clothing with a cause store. Featuring ethically made and fair trade items from over 10 countries, every item is made by women facing extreme challenges such as trafficking, poverty, and more. Your purchase empowers women to take life’s lemons and make lemonade.  Shop at THELemonadeBoutique.com. Listeners of the Business with Purpose Podcast can save 15% by using code PURPOSE15 at checkout.

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Some seasons stretch you in ways you wouldn’t choose, but end up shaping you anyway. Today, I finished my fourth semester of seminary (I`m officially halfway through!) in the middle of a beautiful and hard season... it reminded me that growth doesn’t come from having it all figured out. It comes from showing up, staying connected, and trusting that what’s forming quietly now will matter later.

Grateful for the lessons I didn’t plan on learning. 🤍

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Some seasons stretch you in ways you wouldn’t choose, but end up shaping you anyway. Today, I finished my fourth semester of seminary (I'm officially halfway through!) in the middle of a beautiful and hard season... it reminded me that growth doesn’t come from having it all figured out. It comes from showing up, staying connected, and trusting that what’s forming quietly now will matter later. 

Grateful for the lessons I didn’t plan on learning. 🤍

⭐️ ONE MONTH ⭐️

How is she one month already? Also, why was my pregnancy 753 years long, but she was born five seconds ago. This girl has been the greatest blessing and surprise of our lives and we are obsessed with her.

Her quilt handmade by my dear friend @beakersandbobbins is perfect for this btw. 😭🥹😍 #galileejoy

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⭐️ ONE MONTH ⭐️ 

How is she one month already? Also, why was my pregnancy 753 years long, but she was born five seconds ago. This girl has been the greatest blessing and surprise of our lives and we are obsessed with her. 

Her quilt handmade by my dear friend @beakersandbobbins is perfect for this btw. 😭🥹😍 #galileejoy

Can’t stop won’t stop.

#galileejoy #newbornlife #babyhumor

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Can’t stop won’t stop. 

#galileejoy #newbornlife #babyhumor

Just got our maternity pictures back and I love them so much. And so thankful we got them taken in the nick of time. Grateful doesn’t cut it. 📸 @stellaandbirdiephotography //

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Just got our maternity pictures back and I love them so much. And so thankful we got them taken in the nick of time. Grateful doesn’t cut it. 📸 @stellaandbirdiephotography //

Extra extra thankful this year. Happy Thanksgiving from the fab-5 Stillman crew. 🦃🍁🍽🧡

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Extra extra thankful this year. Happy Thanksgiving from the fab-5 Stillman crew. 🦃🍁🍽🧡

Two weeks with this punkin’ and I’m wondering if there’s some sort of serum we could give her to keep her this precious and tiny forever. Also, this is a Galilee fan account now. #galileejoy

(sweater from her seminary auntie @13buttercreamstreet)

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Two weeks with this punkin’ and I’m wondering if there’s some sort of serum we could give her to keep her this precious and tiny forever. Also, this is a Galilee fan account now. #galileejoy 

(sweater from her seminary auntie @13buttercreamstreet)

On #worldprematurityday, our preemie, Galilee Joy, would like to say: “Already this household is bending to my every will! Muahahahahaha.”

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On #worldprematurityday, our preemie, Galilee Joy, would like to say: “Already this household is bending to my every will! Muahahahahaha.”

World, meet the miracle we never knew we’d witness… our daughter, the best surprise of our lives: Galilee Joy Stillman.

I’ve wrestled with how I’d even begin to write a post like this, but at this point, this is my imperfect attempt. For those that have followed along, in 2018, we lost our sons Elijah and Malachi in back-to-back second trimester losses. After that, we essentially were told we couldn’t have more children and so we’d grieved, but accepted the reality, and trusted God in it all.

Fast forward to April of 2025, and I find myself with the surprise of a lifetime - a positive pregnancy test. We chose to keep the news close to ourselves and just our close friends and family… this pregnancy was not without its complications (pregnant at 40 is NO JOKE 🥴), but God’s hand was in every detail. Also, hiding this from the internet was a challenge! 😂

This past Monday, I went in for a routine OB checkup at 35 weeks and, long story long, ended up in the hospital, diagnosed with severe preeclampsia and sent into an emergency c-section. Our miracle was born at 5:25pm and the sound of her cry filled the room with JOY. We didn’t find out her gender until birth so hearing “it’s a girl!” was such sweet news!

This week has not been without its challenges for us both and we’re not out of the hospital yet, but we’re thankful that God’s been protecting us all along. I’m at a loss for words at how the people in our lives have showed up for us this week and beyond. There aren’t enough thank yous to adequately express our gratitude.

I’ll share her full birth story at some point because it’s a doozy.

For those who pray, we will gladly accept any you would like to send our way.

For now, enjoy a few pics of our Galilee Joy. 💕 #galileejoy

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World, meet the miracle we never knew we’d witness… our daughter, the best surprise of our lives: Galilee Joy Stillman. 

I’ve wrestled with how I’d even begin to write a post like this, but at this point, this is my imperfect attempt. For those that have followed along, in 2018, we lost our sons Elijah and Malachi in back-to-back second trimester losses. After that, we essentially were told we couldn’t have more children and so we’d grieved, but accepted the reality, and trusted God in it all. 

Fast forward to April of 2025, and I find myself with the surprise of a lifetime - a positive pregnancy test. We chose to keep the news close to ourselves and just our close friends and family… this pregnancy was not without its complications (pregnant at 40 is NO JOKE 🥴), but God’s hand was in every detail. Also, hiding this from the internet was a challenge! 😂

This past Monday, I went in for a routine OB checkup at 35 weeks and, long story long, ended up in the hospital, diagnosed with severe preeclampsia and sent into an emergency c-section. Our miracle was born at 5:25pm and the sound of her cry filled the room with JOY. We didn’t find out her gender until birth so hearing “it’s a girl!” was such sweet news!

This week has not been without its challenges for us both and we’re not out of the hospital yet, but we’re thankful that God’s been protecting us all along. I’m at a loss for words at how the people in our lives have showed up for us this week and beyond. There aren’t enough thank yous to adequately express our gratitude. 

I’ll share her full birth story at some point because it’s a doozy. 

For those who pray, we will gladly accept any you would like to send our way. 

For now, enjoy a few pics of our Galilee Joy. 💕  #galileejoy

Six years ago I felt God calling me to go to Seminary. I ignored that call, coming up with excuse after excuse as to why I shouldn’t or why I *couldn’t* do it. Then in 2024, God swung the door to attend @denverseminary wide open to join the Women’s Leadership Cohort and practically shoved me through.

I’m finishing my first full year and just completed my first residency week on campus studying the Epistles and Revelation. I didn’t know what to expect walking into this week, but any expectation I COULD have had was completely blown away.

To study under the brilliant Dr. Joey Dodson (@jrrdodson) and guests like @preston.sprinkle, @madisonpiercephd, @studies_in_revelation, and more was incredible. To learn alongside some of the most brilliant women I’ve ever met was a gift.

I’m leaving with even more questions than I arrived with, but also more assurance that I am PRECISELY where I am supposed to be. I can’t help but smile thinking about the Apostle Paul learning that in 2025 a group of WOMEN are studying the Word of God and how much that would delight him. I pray I steward this responsibility well. #womeninseminary #densem #denverseminary #seminary #densemwlc #womensleadershipcohort

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Six years ago I felt God calling me to go to Seminary. I ignored that call, coming up with excuse after excuse as to why I shouldn’t or why I *couldn’t* do it. Then in 2024, God swung the door to attend @denverseminary wide open to join the Women’s Leadership Cohort and practically shoved me through. 

I’m finishing my first full year and just completed my first residency week on campus studying the Epistles and Revelation. I didn’t know what to expect walking into this week, but any expectation I COULD have had was completely blown away. 

To study under the brilliant Dr. Joey Dodson (@jrrdodson) and guests like @preston.sprinkle, @madisonpiercephd, @studies_in_revelation, and more was incredible. To learn alongside some of the most brilliant women I’ve ever met was a gift. 

I’m leaving with even more questions than I arrived with, but also more assurance that I am PRECISELY where I am supposed to be. I can’t help but smile thinking about the Apostle Paul learning that in 2025 a group of WOMEN are studying the Word of God and how much that would delight him. I pray I steward this responsibility well. #womeninseminary #densem #denverseminary #seminary #densemwlc #womensleadershipcohort

“Let the strength of your passion match the depth of your study.”
-Preston Sprinkle

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“Let the strength of your passion match the depth of your study.”
-Preston Sprinkle
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