Bold Ask Led to Steve Jobs Meeting

Turning Bold Asks into Opportunities: Andrew Wilkinson's Steve Jobs Encounter

As a teenager running a tech news website, Andrew Wilkinson demonstrated how audacity and positioning can create unexpected opportunities, even when the initial request seems impossible.

Situation

• Andrew was a 17-year-old running a tech news website called Mac Teens
• Steve Jobs was his absolute hero - "he is my Jesus" in Andrew's words
• Apple was conducting a store tour at Macworld in New York around 2003-2004
• At this time, no other Apple stores existed yet

Actions

• Made the bold request: Andrew emailed Apple PR directly asking to interview Steve Jobs
• Accepted the alternative: When PR laughed off his request, he accepted their counter-offer of a store tour
• Positioned himself strategically: Arrived early and positioned himself first in line for the tour
• Seized the unexpected moment: When Jobs unexpectedly arrived in a black SUV, Andrew was perfectly positioned
• Stayed close and engaged: Rather than freezing, Andrew stayed at Jobs' side throughout the tour
• Asked questions continuously: Despite being "a quivering mess," he continuously engaged Jobs with questions

Results

• Andrew got a personal introduction and handshake from Steve Jobs
• He managed to have an extended conversation with Jobs throughout the store tour
• While not a formal interview, he was able to ask numerous questions about Apple products
• The experience became a memorable life moment that reinforced a powerful business philosophy

Key Lessons

• "Ask big and maybe you'll get something great": Even if you don't get exactly what you ask for, bold requests can lead to valuable alternatives
• Position yourself for opportunity: Being first in line literally put Andrew in position to meet Jobs
• Preparation meets luck: The encounter wasn't purely luck - Andrew created the conditions for it to happen
• Overcome intimidation in the moment: Despite being starstruck, Andrew pushed through his nerves to engage
• Accept the alternative path: When your original goal isn't possible, the alternative might still be valuable
• Strategic persistence pays off: Andrew didn't get the formal interview, but by staying close during the tour, he effectively created an informal one

This approach of "asking for amazing" and being ready to accept "something great" became a foundational principle in Andrew's business philosophy, demonstrating how audacity combined with flexibility can create unexpected opportunities.