At the time, I was making less than $40K a year and spending $500 or more per month on supplements. I started with my credit card statement and asked myself, “What do I spend a silly amount of money on?” Where did I spend a disproportionate amount of my income? Where was I price insensitive? The answer was sports supplements. To explore business opportunities, I didn’t do in-depth market research.
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I wasn’t sure what to do, but I’d been bitten by the startup bug and intoxicated by Silicon Valley. Rounds of layoffs started and weren’t going to end. In late 2000 and early 2001, I saw the writing on the wall: The startup I worked for was going to implode. #2 - What do I spend a silly amount of money on? How might I scratch my own itch? My last quarter in that job, I outsold the entire L.A. The big boss often picked up the phone directly, and I began doing more experiments with “What if I did the opposite?”: What if I only asked questions instead of pitching? What if I studied technical material, so I sounded like an engineer instead of a sales guy? What if I ended my emails with “I totally understand if you’re too busy to reply, and thank you for reading this far,” instead of the usual “I look forward to your reply and speaking soon” presumptive BS? The experiments paid off. For the rest of the day, I focused on cold emails. What if I did the opposite of all the other sales guys, just for 48 hours? I decided to take a Thursday and Friday and make sales calls only from 7 to 8:30 a.m. Part two: I realized that all of the gatekeepers who kept me from the decision makers-CEOs and CTOs-also worked from 9 to 5. Then, one day, I realized something: All of the sales guys made their sales calls between 9 a.m. For the first few months, I flailed and failed (it didn’t help that my desk was wedged in a fire exit). When I wasn’t driving my mom’s hand-me-down minivan to and from the office in San Jose, California, I was cold calling and cold emailing. In 2000, I was selling mass data storage to CEOs and CTOs in my first job out of college. #1 - What if I did the opposite for 48 hours? Each one is time-stamped, as they entered the picture at precise moments.
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What follows are 17 questions that have dramatically changed my life. If you stress-test the boundaries and experiment with the “impossibles,” you’ll quickly discover that most limitations are a fragile collection of socially reinforced rules you can choose to break at any time.
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“ Whenever you find yourself on the side of the majority, it is time to pause and reflect.”
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