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A big thanks to Jordan Lee of Collections for summarizing yesterday’s session with Maynard Webb. A great read and some outstanding advice:
The West Coast Summer@HIGHLAND teams (with Cambridge video-conferenced in) were treated to lunch with one of Silicon Valley’s most trusted operating executives, a man whose driving impulse is to look for the largest, most important fire burning at any given moment and do whatever it takes to extinguish it.
From the earliest days of his career, when he was working as a security guard and angling for opportunities to advance (such as learning how to program and break systems), Maynard Webb lived by one simple rule: chase down the difficult and unpopular challenges that everyone else seemed to be avoiding and deliver results no one thought were possible. From rescuing eBay from the brink of calamity as its Chief Operating Officer (and then helping it to grow from $140 million in revenue to over $6 billion in seven years), to serving as President and CEO of LiveOps and as a senior executive at Gateway, Quantum, and IBM, Webb has never shrank from a challenge.
Still Chairman of the Board at LiveOps, Webb turned his attention last year to a host of new pursuits. He founded the Webb Investment Network, which together with 75 seasoned affiliates invests in and coaches young entrepreneurs who have transformative ideas. He also recently joined Yahoo’s Board of Directors, underscoring his commitment to tackling the toughest problems around, and recently wrote a book called “Rebooting Work: Transform How you Work in the Age of Entrepreneurship,” which will be published in January.
The teams were held in rapt attention as Webb recounted his improbable personal story and drew lessons from his experience, several of which were especially relevant for us:
- The danger of complacency – As a company grows, founders should never stop asking themselves, “Am I pulling my weight?” It’s not healthy for a company’s leadership, nor for its employees, if founders become complacent or abuse their seniority and free ride on the work of others. Relatedly, Webb also enjoined us to be our own toughest critics to ensure that we’re really contributing our all, and to be careful not to “confuse action for traction.”
- The overriding importance of integrity – Founders face a raft of unique pressures that risk compromising their integrity. It’s important to look forward many years into the future and ask if you’ll be able to live with the decisions you’re making now. Reputation, after all, is as easy to lose as it is difficult to acquire.
- Be brave, bold, flexible, and positive – Nobody wants to work with someone who’s cranky all the time, so keep your attitude in check. And given that change is inevitable, you might as well embrace it rather than resist it. Ultimately, an entrepreneur must be brave and bold enough to see the change they want to see in the world and then work furiously to get there.
At the end of lunch Webb was asked what helped him sort through his many different opportunities and what gave him the conviction to keep going. He paused for a moment and then shared a mental exercise that he would use when he was starting out. Imagine yourself in thirty years on a stage in front of all of the people you admire most in the world. You have to tell them the story of your life, and what you say will be met with one of three reactions. They might deliver faint praise (“well, not bad given the circumstances”), they might be underwhelmed (“that doesn’t quite cut it”), or you could truly knock their socks off so that they’re left scratching their chins in disbelief.
It’s clear that Webb is on track to achieve the third. Hopefully, with a bit of his wisdom adding wind to our sails, we too can strive for greatness.