Crossroads for an Entrepreneur, with John Pepper

The Sydcast

Episode Summary

John Pepper is a restaurant entrepreneur, angel investor, and a hands-on advocate for the rights of low-wage workers. He’s been an Uber driver, confronted small-town Vermont politics, and turned a banned college fraternity house into a shared work space for startups. Motivated by social justice, sustained by business, he shares his story, on this episode of The Sydcast.

Sydney Finkelstein

Syd Finkelstein is the Steven Roth Professor of Management at the Tuck School of Business at Dartmouth College. He holds a Master’s degree from the London School of Economics and a Ph.D. from Columbia University. Professor Finkelstein has published 25 books and 90 articles, including the bestsellers Why Smart Executives Fail and Superbosses: How Exceptional Leaders Master the Flow of Talent, which LinkedIn Chairman Reid Hoffman calls the “leadership guide for the Networked Age.” He is also a Fellow of the Academy of Management, a consultant and speaker to leading companies around the world, and a top 25 on the Global Thinkers 50 list of top management gurus. Professor Finkelstein’s research and consulting work often relies on in-depth and personal interviews with hundreds of people, an experience that led him to create and host his own podcast, The Sydcast, to uncover and share the stories of all sorts of fascinating people in business, sports, entertainment, politics, academia, and everyday life.

John Pepper

John is co-founder and Chief Worker Advocate of Boloco, a New England-based restaurant chain and Certified B Corp founded in 1997 serving Modern Mexican-inspired food and beverages. He is also co-founder of Worthee, an early-stage software project/platform focused on helping hourly workers receive the information they need to rise and thrive. Pepper also co-founded B. Good which grew to 80 units before he and his partners sold it in 2017.

Pepper has been an angel investor since 2014, with investments in more than 30 start-ups focused on workforce-empowering technology, restaurant-facing technology, and a few special consumer businesses like Athletic Brewing, Spindrift, Free Rain, and Starbird.

Pepper graduated from Dartmouth College in 1991 and received his MBA from the Tuck School in 1997 (where he presented the first Boloco business plan). He was elected to the Selectboard of Norwich, VT in 2017 and was Chairman from 2018-2020.

His wife Maggie and their 3 kids live in Hanover, NH.

Insights from this episode:

• Insights into Boloco and how it became successful
• How the branding of his restaurant to Boloco was done
• Pepper’s strategies for running a restaurant
• Insights into successfully raising capital
• Pepper’s lessons from being an Uber driver
• Insights into how Worthee came about
• What’s next for Boloco
• Effects of COVID-19 on restaurant business
• Pepper’s rehabilitation of Dartmouth College

Quotes from the show:

• “I am always curious about what’s ticking behind any business, and frankly any job” -John Pepper [3:15]
• “The first thing I had to do when I got back was to realize that we don’t know what we are doing and we need to hire talent: We need to hire someone better than us” -John Pepper [9:52]
• “Their [investors] main objective was to transform me from an entrepreneurial CEO, they said, to a professional CEO” -John Pepper [16:51]
• “I became an Uber driver back in Boston and it informed me a lot about the work I have done since” -John Pepper [23:19]
• “I did come away with a sense that flexibility was going to matter for workers. And we’ve got to figure out how to include people who are stuck in rigid low-paying jobs; put them into flexible jobs so that they’ll find time for better education, skills development and a way to get out of low paying jobs” -John Pepper [29:52]
• “People just don’t get regular feedback in any way that helps them understand their strengths and that led me to start thinking what can we do to solve that problem” -John Pepper [34:34]
• “Our goal has always been, and this is not a high bar, to be the number one highest wage payer in the industry” -John Pepper [40:08]
• “It’s all about work-from-home habits that are not temporary; they are here to stay. Yes, people will move back to the office, but I don’t think we will move back to 100% of what it was in 2019” -John Pepper [48:45]
• “I think that small businesses right now we don’t have the technology. I am investing in technology that does allow businesses like ours to compete with the big chains” -John Pepper [50:14]
• “I do use Boloco today as a petri dish for interesting new technologies. I aggressively implement things that aren’t always so good for our business, but inform us on what is good for the business but also help me in making investment decisions” -John Pepper [53:20]

Stay connected:

Sydney Finkelstein

Website: http://thesydcast.com

LinkedIn: Sydney Finkelstein

Twitter: @sydfinkelstein

Facebook: The Sydcast

Instagram: The Sydcast

John Pepper

LinkedIn: John Pepper

Website: johnpepper.com

Boloco's Website: Boloco

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This episode was produced and managed by Podcast Laundry.