How To Be A Successful Entrepreneur: Just Ask

Successful Entrepreneur Just Ask
Learning How To Be A Successful Entrepreneur

My first job out of school was working as a consultant at Bain & Company. When I joined I didn’t know anything. I was greener than green. After becoming a serially failing founder in college I thought a job as a consultant would teach me a few things. Maybe I’d get closer to learning how to be a successful entrepreneur.

After a month of business boot camp, I was assigned to join my first project. Bain at the time was helping DHL reboot its US operations. Interestingly, while DHL was actually founded in San Francisco to help expedite the customs paperwork of ships coming into harbor, the business had become dominant internationally and very weak domestically.

The Opportunity

The courier business is all about scale. The more packages you pack onto a plane or truck the lower the average cost per package and the more profitable the company is. They call that delivery density. And the US arm of DHL didn’t have much of it.

Bain was brought it to put their thumb in an enormous leak in the US business. They were bleeding money. The team at Bain was pretty sharp and well suited to help. It was a multi-year project, and while I left before it wrapped up, I assume Bain had a big impact.

My Learnings

While I was there I learned a few things. The first was that I noticed DHL US had a sales-driven culture to a fault. The company had promoted sales folks into every field of management. While there’s nothing wrong with sales people, business takes all types of disciplines. It was like a high school where every subject was taught by a math teacher. The good news is that with some hiring that was correctable.

Not coincidentally, the other lesson I learned was a sales lesson from one of the salesmen turned senior executives. During the course of the project this senior executive had taken to me. I think he saw an opportunity to mentor a beginner.

He was the type of dude you’d expect to meet at a tailgate. And he had a personality that consumed the room and probably intimidated his counterparts in business. One night after work he took me out for beers and told me a story that I’m sure he’d told every chance he got.

“Mark,” he said, “I’m not a good looking guy. But I married a Lakers cheerleader. The key to life is ‘just ask.’ Worst case somebody says ‘no’ and you’re no worse off. But a lot of the time people will say ‘yes.’ I was way out of my league, but I asked her out and now she’s my wife.”

Key Take Away: Just Ask

It’s hard to ask people for things. While the fear of rejection seems to affect folks differently, I was afraid of it when I was younger. The “just ask” mantra stuck with me though. So – taking his advice – I kept asking and I got more of what I wanted and it got easier over time.

It’s a simple lesson, but a powerful one that overtime can transform your career and maybe your life.