Lessons on Life, Entrepreneurship, and Impact with Maynard Webb

Episode Summary From a young security guard at IBM to a white-hat hacker to a titan of technology in Silicon Valley, Maynard Webb has digitally done it all.  Serving on the boards of some of the biggest players in the digital corporate world, Maynard has seen the industry rise and evolve and he’s still helping to make the world a safer, better, and more inclusive place.  Maynard and Syd discuss how the COVID pandemic has affected the workspace, the insidious effects of systemic racism, and the journey he’s on to be more informed, in this episode of The Sydcast. Syd 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.    Maynard Webb Maynard Webb is a 40-year veteran of the technology industry.  As an active leader in the technology and business community, Maynard serves as a board member, investor, philanthropist, and mentor to young entrepreneurs.  As the founder of the Webb Investment Network (WIN), a seed investment firm dedicated to nurturing entrepreneurs, Maynard brings his experience developing and leading high-growth companies. Maynard currently serves on the boards of Salesforce and Visa.  Previously, Maynard served as Chairman of the Board of Yahoo!, CEO of LiveOps, COO of eBay, and held executive roles at Gateway, Bay Networks, and Quantum. In 2004, he and his wife created the Webb Family Foundation, which provides underprivileged, motivated young individuals access to quality education and supports individuals who are struggling against the odds to make a positive impact on the world through innovation and hard work. Maynard is the author of two bestsellers, Rebooting Work: Transform How You Work in the Age of Entrepreneurship and Dear Founder: Letters of Advice for Anyone Who Leads, Manages, or Wants to Start a Business. Insights from this episode:Benefits and drawbacks to living in the digital age on personal, business, and political levels.Reasons why cybercrime has recently become such a huge issue including better criminals and poor products.How Salesforce pivoted during the pandemic to help people get back to work and into the workplace.Details on the company culture in the technology industry; how it used to be, how it is now, and the direction it is heading.Strategies for going beyond affirmative action to create a truly diverse workplace and details on Visa’s plan to tackle the diversity problem.  Quotes from the show:On being a hacker: “I have to say it’s quite fun because it’s like solving a big puzzle with how do you actually get into something.”  – Maynard WebbOn cybercrime: “I think it’s a consequence of how successful we’ve been in digitizing everything.”  – Maynard WebbOn the benefits of video conference: “It’s a lot better to have a conversation when you can see somebody.”  – Syd Finkelstein“The bad guys are the most innovative folks in the world and they change every week, every day, there’s a new threat.  Yet, our biggest threats still are from sloppy behavior.  People not patching systems that leave them open.”  – Maynard Webb“It’s a different organizational system that has been created in the world of cybercrime that seems to be beating us who are following a more traditional and ‘sophisticated’ way of organizing and managing.”  – Syd FinkelsteinOn COVID changing the relationship between employees and businesses: “I think that the whole work relationship is going to change and where people live and I think there’s a lot of ramifications still to come from this.”  – Maynard Webb“What you don’t want to lose is some of the magic that comes from being in person but maybe we don’t need to be in person, together, all the time.”  – Maynard WebbOn operating a business during COVID: “The need for effective communication is really through the roof and transparency is critical.”  – Syd FinkelsteinOn networking: “You want to have a following but you want to be inclusive of new thoughts as well.”  – Maynard WebbOn systemic racism: “I don’t think it’s enough anymore to feel bad; we have to take action and we have to do things that are going to make a meaningful difference.”  – Maynard Webb Resources Mentioned: www.work.com by SalesForce Brotopia: Breaking up the Boys’ Club of Silicone Valley by Emily Chang Stay Connected:   Syd Finkelstein Website: http://thesydcast.com LinkedIn: Sydney Finkelstein Twitter: @sydfinkelstein Facebook: The Sydcast Instagram: The Sydcast   Maynard Webb Website: www.maynardwebb.com LinkedIn: Maynard Webb Twitter: @maynard Subscribe to our podcast + download each episode on Stitcher, iTunes, and Spotify. This episode was produced and managed by  Podcast Laundry (www.podcastlaundry.com)