When you are Larry Ellison’s handler, you need to be prepared for anything. I mean anything. The strategic planning time alone for one of his speaking engagements could be up to a year and a half.

Take into consideration the due diligence, evaluation process a request goes through, internal endorsements within the organization and onto the final confirmation. That’s just the beginning. Then, the planning process of all the business and media activities around his Keynote and the logistics and briefing documents.

Oh, and take into account this is for one of the most exuberant CEO’s of all time who expected a level of seamlessness and perfection every.single.time.

You are probably not reading this article for the job description so let’s get to the good stuff!

Storytime ~ get cozy.

It was mid 2000 and I was in my late 20’s. I arrived at the St. Regis in Aspen, Colorado for Larry’s post lunch Keynote at an Oracle customer’s conference. It was my first (and last) time in Aspen and I don’t think I’ve ever seen such a beautiful sky or breathed in such crisp air. Those leisurely 10 minutes were memorable.

As usual, I flew in the day prior to meet with the conference organizers, get familiar with location, find walking routes and make sure everything from audio/visual to security was ready to go when he arrived.

It had to be seamless from Larry’s perspective. He was taking his own plane and flying himself. I coordinated with his driver on where the car would arrive and walk with Larry to the green room while briefing him for a meet + greet, and then he would take the stage.

Sounds straight forward, right? Nope. That morning, I learned he didn’t leave on time. The customer’s staff wanted to know the exact time Larry was arriving. In all truth, I didn’t know. I got a call from his assistant telling me there may be mechanical issues. Deep breath. I knew it was going to be a very intense day.

Finally, I was relieved to hear he was in the air, about 60 minutes later. It was a half hour prior to his Keynote and he had not arrived yet and by not arrive, I mean his plane was still in the air.

By that point, I had Larry’s 2 security guards, who I knew well, standing by relaying information like “turbulence,” “winds are strong” and other reasons why he was going to be late. It was comforting, yet unnerving to have Larry’s security feel nervous for me. We pulled together as a team knowing there was no solution other than to wait it out.

What could I do? I had prepared for everything within my control but I couldn’t make him get to the conference any faster. That’s when a group of 3 Executives came over and started raising their voices to me, “Where is he? Why is he going to be late? Who are you, anyways? What time did he leave?” Their agitation and questions were fiercely coming at me.

That’s when I owned it. I said something to the effect, “Yep, he’s gonna be late. There is nothing you or I can do to get him here faster. Let’s focus on the solution and what we can do. Your attendees are finishing lunch. Can someone from your company provide them an update, speak for 15 minutes about something? Our team will let you know the minute he is in the car.” Just like that, 3 still agitated executives, began to make a plan.

Here is what I really learned and it was more about myself that day. I was intimidated of these types of situations but knew I had to get over my insecurities and do my job. That was the day I stepped up … the day I moved from self-doubt to confidence in my role and when I learned to use my voice. Here’s how it prepared me for entrepreneurship.

Entrepreneur Takeaways

1. Be Prepared + Then Wing It

As a Handler, the day of the event, my role shifted from the strategic planning phases to the tactical operation of a few hours.

As an entrepreneur, you aren’t going to be in that exact situation, however, you will need to be prepared for when you do meet with your first customer, your first major account, your first media interview. Do this strategically by writing out the possible scenarios. Being prepared will give you a sense of confidence walking in the door.

When I walked through the outdoor seating area where Larry was going to present, his security and I looked at all the potential ways he could get to and from the stage and ultimately created a plan 1 and plan 2. We talked to the hotel security, checked for other events going on at the hotel and nearby and looked at all the angles someone could potentially harm him.

Prepare for what is in your control, then wing it. Being flexible and able to change your direction at a moments notice is critical in any business. When you are an entrepreneur, you are constantly changing direction, trying new ways to attract customers until you figure it out.

2. Realize They May Not See What You See...Yet.

Just like the executives pouting, they weren’t focusing on a solution. They were focusing on emotion and that isn’t going to solve anything.

Realize that your friends, family and inner circles may not see what you see...yet. But, that is something you are going to have to move past. Sure, it can be discouraging that not everyone sees how INCREDIBLE it is from the beginning, but let it go. Allow yourself to feel disappointed for a short time frame, then focus on the business.

Focus on your product, your business and seek out entrepreneur meet-ups to meet like-minded people who get it. The entrepreneur community will be your new best friends. They get IT in a way no one else can.

However, if your customers don’t see the value, find out why. That is the one person you need to listen to when starting your business.

3. Try Not To Take It Personally

In my corporate situation, I easily could have gotten caught up in the customer’s hostility towards me. I chose not to react emotionally to their negativity. I took a level headed approach. It was easier to do because I understood their frustration and knew it wasn’t personal.

That is not the case when you are an entrepreneur. When you have an idea and begin to form that into a business, it is very personal. As past colleagues, friends, family give you initial feedback; sometimes its hard to stomach. Comments like...

• Umm, okay so that’s why you quit your awesome job? (that’s what I heard when I quit to start my own business)

• That’s your BIG idea ~ isn’t someone doing it already? How will you compete?

• Sounds great but … then the million questions of how you are going to do it, get funding, publicity, customers and the list goes on and on …

You realize you don’t have ALL the answers and start second guessing yourself. Your confidence takes a slight dip. You feel like you have it all figured out one minute and then the next minute you wonder if you are crazy.

4. It’s Not Glamourous

“Wow, you were Larry Ellison’s handler? That must have been so glamourous.”

Umm, not really.

“But you got to travel and stay at 4 star hotels.”

Yes, that was nice but I was in my room working away, doing walk-throughs or meeting with staff.

It wasn’t a vacation.

Like being an entrepreneur, it looks one way from the outside but the reality is … much more like reality.

These days, being an entrepreneur has cache. It’s sexy now. TV shows are written about it like Silicon Valley and Shark Tank is one of the biggest hits on television.

Did you become an entrepreneur thinking ...

• Heck yeah! I want control over my destiny

• I love running the show and making the decisions

• My product is better than anything anyone has ever seen

Then you realize…

• I’m responsible for every.single.detail.and.decision.every.single.day.7.days.a.week

• I wish I had someone to rely on but can’t afford to pay anyone, let alone myself

• My product is better but no one knows about it

Yep, sometimes it is hard not to get caught up in the “glamour” of what we are doing or how we want to see ourselves or be perceived.

Besides preparing a business plan, think about an emotional plan. How much can you stomach as a person? Can losing an investment from friends and family make you sick? Try to think through as many realities prior to jumping in full-throttle. It can be easy to overlook when you are soo excited about an idea and you just KNOW it will work. Plan for the worst, expect the best.

5. Setting and Meeting Expectations

The Executives’ expectations weren’t met. They expected Larry Ellison to show up on-time as their closing Keynote, WOW their audience. When they thought he might not show, they panicked. It would create a chain reaction. Their audience would be disappointed, too and it would shed the customer in a bad light.

Everyone wanted to deliver but other circumstances prevented it from happening smoothly. It wasn’t lack of intention and that is important to point out.

Although he was late, ultimately all went well. He took the stage and in Larry fashion made a funny joke immediately addressing the delay. He charmed everyone and no one cared he was late.

As an entrepreneur, YOU set the expectations with yourself and your customers. Although you may think you can get your App out the door on x timeline or the product you manufactured and shipped ends up having a defect, things go wrong. All.the.time.

What happens when your customer orders your product but you know he won’t receive it in time?

Communicate each step of the way. People like to be informed and know what is going on. Make them a part of that journey.

When something goes wrong, don’t pretend like everything is perfect, blame someone else or make an excuse. Acknowledge what happened and own up to it. They will respect you and trust you. And so will you.

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