Diversity & Inclusion

The Purpose-Driven Entrepreneur

Rob Chesnut is a distinguished gentleman.

Rob Chesnut Headshot

“Their passion for the subject of integrity was a great sign that it wasn’t just about financial success for them.”
Rob Chesnut, former Chief Ethics Officer turned Advisor at Airbnb

His career highlight reel includes a string of senior leadership roles such as Assistant U.S. Attorney, Deputy General Counsel at eBay and, more recently, General Counsel and Chief Ethics Officer turned Advisor at Airbnb. Rob is the author of ‘Intentional Integrity: How Smart Companies Can Lead an Ethical Revolution.’ Most recently, he was a mentor for the Mentorship Circle program at the Nasdaq Entrepreneurial Center, focusing on ‘ethical leadership.’

In our interview (which has been edited and condensed for clarity), Rob discusses:

  • The reciprocal (and ubiquitous) nature of mentorship;
  • The corporate paradigm shift from an exclusive focus on shareholders to inclusion of Black community stakeholders; and
  • His three-pronged test to determine whether founders are purpose-driven or profit-driven.

Do you have (or have you had) a mentor(s) and, if so, what impact has this relationship(s) had on the trajectory of your professional life?

RC: Certainly, people invested in me and took extra time with me to help me grow. I could probably name 50, so I’ve been extremely fortunate.

To me, the word ‘mentor’ implies a one-way relationship, but I don’t look at it that way. Whenever I spend time with someone, I usually come away having learned something. I get inspired, too.

You can learn from anybody. Everybody you meet is a potential mentor, even people who are junior to you. You don’t know everything, so you can learn a ton from people who have been through it all and made mistakes along the way.

What attracted you to the Mentorship Circle program?

RC: I love opportunities to talk to young people.

Nasdaq is a particularly attractive place because I love working with entrepreneurs. That’s what Nasdaq stands for. So, the fact that they were running a program specifically to help Black entrepreneurs was a great opportunity to give back and meet young entrepreneurs.

What are your expectations of a mentee?

RC: Questions that come to mind include: ‘Are they passionate?’ ‘Are they committed to getting better?’ and ‘Are they open to sharing with me?’

Mentoring is a two-way street though. So, bring your passion, curiosity, enthusiasm and gratitude and I’ll try to do the same.

What are the biggest obstacles facing Black founders?

RC: A lot of the world revolves around who you know, so I think it’s a lack of connections. Connections aren’t essential, but they can certainly help.

Too many young Black people don’t have connections to venture capital and they don’t have enough role models in leadership. If there aren’t enough Black people in positions of authority in business and they’re not in venture capital, where can young Black people go in order to form these connections?

What is one thing that must be changed immediately?

RC: In business, we need to move away from the old school philosophy, which says that it’s all about shareholder value. This shift is happening, but not quickly enough.

Companies have obligations to their shareholders, employees, customers and to the communities in which they do business. But we’ve got to move to a world where companies have bigger obligations to a broader, more external group of stakeholders that includes the Black community in general and specifically young Black people.

We’ve got to move to a world where companies have bigger obligations to a broader, more external group of stakeholders that includes the Black community in general and specifically young Black people.

In addition to mentorship, what else is critical to an entrepreneur’s success?

RC: Finding something to do that you’re passionate about and being endlessly curious about it.

Work doesn’t feel like work when you’re driven to do something that is bigger than yourself and you feel that what you’re doing is good for the world, that’s a powerful combination.

When you’re driven to do something that is bigger than yourself and you feel that what you’re doing is good for the world, that’s a powerful combination.

What was your favorite moment of the program?

RC: On the program, I talked about integrity.

Oftentimes, entrepreneurs only want to make money and get rich. So, what I loved about the program was how engaged the founders were, the number of questions they asked, the stories they told and how many founders were eager to share.

Their passion for the subject of integrity was a great sign that it wasn’t just about financial success for them. There was a lot of passion for doing sustainable, long-term business in a way that feels right. That resonated with me.

Did you reap any unexpected benefits or face any unexpected challenges and, if so, what were they?

RC: Going into the program, I questioned how the founders were going to connect with me. I don’t look like them, plus I’m three times their age!

I always tend to worry a bit before giving these talks. I wonder if the younger entrepreneurs are thinking: ‘here comes this old guy talking about morality.’ But over time, I’ve learned that these talks actually resonate with young people. They don’t often hear talks about values so, when they do, it tends to strike a chord with them.

How did the experience differ from any previous mentorship programs you may have been involved in?

RC: The fact that it was specifically focused on helping Black entrepreneurs as opposed to helping entrepreneurs generally.

Most people feel that the Black community has been so underserved. So, it was gratifying to do something that helps the Black entrepreneurial community instead of a room where there’s just one or two Black entrepreneurs in it.

What advice (if any) did you give your mentees on the last day of the program?

RC: My key questions to the founders were: ‘why is your company good for the world?’ ‘what is your North Star?’ and ‘what is your purpose?’

While profit is important, entrepreneurs must articulate to potential employees, customers and prospects why what they’re doing is good for the world. They also need to say what their North Star is that will guide them in their decision-making. And they must outline what their purpose is. Profit isn’t purpose. Entrepreneurs must nail these three things down from the beginning.

What excites you most about this new class of founders?

RC: In many ways, my generation hasn’t done a lot of good for the world – especially the climate. My hope is that we’ve got a new generation that is inspired to help fix some of the things that my generation screwed up.

I’m motivated to help in any way I can, particularly because my generation was too focused on wealth creation and not focused enough on doing the right thing. I feel the tide is now turning.

The views and opinions expressed herein are the views and opinions of the author and do not necessarily reflect those of Nasdaq, Inc.

Kieron Johnson

Kieron Johnson is a content/communications consultant to emerging and established brands.

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