Startup Wisdom from Jeff Bezos — and My Cleaning Service

How to successfully enter a crowded category

Sandra Lewis
Published in
5 min readJun 9, 2017

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I had coffee last month with my friend Jane, who runs a video production company. Jane employs 14 people — engineers, designers, and production specialists — and hires freelance crews for shoots. But she told me that one of her toughest management challenges had nothing to do with overseeing staff, finding clients, or producing stellar video content.

“For the longest time,” Jane said, “I couldn’t keep our office clean.”

Jane tried three well-established cleaning services, but none built a track record of reliability, punctuality, and great service. Then, one morning as she arrived at work, she noticed a colorful flyer advertising cleaning services. “Oh right, another one,” Jane thought. But she was desperate, so she dialed the phone number.

A woman named Debbie answered. Debbie had just started her company, so she had no website, and, unlike more established vendors, no fleet of logo-clad automobiles.

“All I have is my hard work,” Debbie told Jane, “and my desire to build a business people will love.”

Three lessons every entrepreneur can learn from Debbie

Today, Jane’s office is spotless. Of course, I asked for Debbie’s number, and now Debbie’s staff cleans our offices. As a client, I’m beyond thrilled.

And as an entrepreneur, I’m intrigued by Debbie’s success. After all, when I founded Worldwide101, the market for virtual assistants already had several well-heeled players, so our predicament was not unlike Debbie’s.

The more I’ve learned about Debbie’s approach to business, the more I realized it was similar to what had worked not only for Worldwide101, but for other upstart competitors I know who have successfully conquered crowded markets:

1. Make the most of your “Day 1” advantage by uncovering new customer pain. Unlike other cleaning services, which seem to take offense when you give them feedback, Debbie checks in every few months to ask if there’s anything her team can do better. She does that consistently, even if the feedback has been good and there is seemingly no need to check in.

That reminded me of Jeff Bezos’s recent annual letter to Amazon shareholders, in which he wrote that he tries to instill the idea that it’s always “Day 1,” meaning that everyone, to some degree, acts as if Amazon is a brand-new startup. As he says, established players become vulnerable when they slip into “Day 2” mentality:

“Day 2 is stasis. Followed by irrelevance. Followed by excruciating, painful decline. Followed by death. And that is why it is always Day 1.”

When we first founded Worldwide101, unlike Debbie, I hesitated to press our Day 1 advantage, and it almost cost us our growth. Back then, I was our only virtual assistant. If clients needed more support, I would subcontract the work, but everything flowed through me.

One day, a prospect demanded to meet every single person who did work for his company. I told him to trust me to hire good people; he told me to take a hike.

At first, I wrote him off as difficult. But more and more prospects were soon asking for the same thing: “You seem great, but if others are going to do the work, can I meet them first?” Eventually I realized that saying yes to that question could be a differentiator — the first virtual assistant company that would be fanatical about taking the time to find the right match between clients and virtual assistants. That change has become one of the big reasons clients love us, and a huge contributor to Worldwide101’s growth.

2.Tell customers how they can help you. Another driver of Debbie’s success is that she asks for help when she needs it. For example, the time of day she was cleaning certain clients’ offices became inefficient given her small crew and the distance between jobs. So she asked some clients if they could accommodate a different schedule. Given her flock of happy clients, most were happy to oblige.

At Worldwide101, my initial reluctance to do what Debbie did nearly killed us. During our first year in business, we would invoice clients at the end of each month for services they had consumed. As you can imagine, we had the problem that so many businesses have: some clients would pay late, leaving us unsure, month after month, if we’d be able to make payroll.

In year two, I began to understand that most of our customers not only loved us, but wanted us to thrive. That gave me the confidence to start asking new clients to pay us in advance of services rendered, with a satisfaction guarantee. I braced myself for the angry backlash, but it never came: not one client challenged the request.

3.Sweat the details. Cleaning, like many jobs, is about details. For example, there’s a huge sofa in our office where we — and our dogs — love to relax. The upholstery isn’t horrible at hiding dirt, but Debbie was the first cleaner to actually vacuum it!

Sweating details is one of the values that I’ve always tried to instill in my company, because customers do indeed notice them. Early on, we used email and spreadsheets to communicate with customers and keep track of billing. But we realized as we grew that we were spending hundreds of hours each month on manual and repetitive tasks. So we built a proprietary dashboard, with interfaces for our clients and our team. It’s a small thing that has revolutionized the way we interact with our clients, saving us time so we can concentrate on bigger things. (Bonus: It has also yielded incredibly valuable data about how we can better serve customers.)

So if you’re an entrepreneur, follow Debbie’s lead. And if your office is a mess, hire someone like her to clean it. There really is something fabulous about working in a clean office. It brings sunshine in on a cloudy day, and makes everyone more productive. I would share Debbie’s number, but she asked me not to — she’s got so much business from word-of-mouth that she’s now booked to capacity!

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Sandra Lewis is the founder of Worldwide101, a premium virtual assistant company connecting demanding founders and executives with highly skilled, meticulously matched help. You can connect with her on Twitter or LinkedIn.

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