Will Pemble: Death by Winning

Will Pemble

How Will Pemble's Greatest Success Nearly Killed Him - and What That Taught Him


Entrepreneur and executive coach Will Pemble has been founding and growing businesses of all shapes and sizes for over 25 years.

Video Will Pemble

Death By Winning

He said that web.com was growing consistently already, but then their customer acquisition shot through the roof – around 2,000 new customers per day. Just like how Factory Records lost money on each copy of New Order’s Blue Monday single, which became the best-selling single ever at that time; web.com’s growth through loss-leaders started to sink the startup through exponential infrastructure costs.

“Everything went to hell in a bucket,” he said. “When you just scale something up, it doesn’t work predictably. Nothing about scale is straightforward!” With a grin he asked, “How can you screw up with a name like web.com?!”

He thought the problem was that he couldn’t rack servers fast enough or hire enough customer-service reps.

Nope: “The stuff that got you to the success you have right now will not get you to the next level.”

Instead of buying more technology, Pemble’s team worked on what they could best work on: themselves. “Everyone who’s been in a bad relationship knows that it can’t be fixed in a day,” he said: it took web.com four years to dig the hole it was in, and it would take time to climb out.

He learned that there were only three things that his team had to worry about in terms of business killers:

1. Communication

When you reach the limit of being able to express what you need, your business will stop, stall, or die.

2. Delegation

As a leader, your ability to get things done without doing them yourself is critical.

3. Time management

No matter how great a boss you are, there are only 24 hours in a day.

So Pemble changed the work culture at web.com… because that’s all they could afford to change. They identified five core values by which to move forward:

  • Teamwork
  • Hard work
  • Communication
  • Delegation
  • Time management

“You really, really, really need to find yourself a true differentiator,” said Pemble, “and it’s always gonna be your people!”

About Will Pemble

He is

  • a certified stockbroker,
  • flight instructor,
  • product manager,
  • technical trainer,
  • commercial instrument pilot,
  • behavioral analyst,
  • and forklift operator;
  • and he builds real-life roller coasters in his backyard.

As the founder of web.com, he never had the same amount of funding as the big dogs, so he had to empower his team, turning them into his secret weapon – and that inspired his executive coaching career.

Pemble founded web.com in 1999, getting his foot in the door of the hosting and domain business.

“We had a couple of differentiators,” he said in his CloudFest keynote, “but, you know, mainly our domain name was kinda good!”

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