Lessons in selling from a Girl Scout dropout

There are plenty of things I remember loving about being a Girl Scout. I loved the mother/daughter sleepovers, the craft badges and the dance parties, to name a few. But, my overwhelming memory of Girl Scouts is how much I hated selling the cookies. Nothing was emphasized more every year in my time as a Girl Scout Brownie (heck, even the title is a reminder of the pressure to sell desserts) than cookie sales. Every year I strained myself to reach the minimum required sales level. I’m pretty sure my parents were the only reason I sold any cookies at all. They would take the order forms to work and save me from the absolute horror of personally knocking on someone’s door to sell them cookies. I never wanted to ask someone of their time and money. I felt bad selling the cookies – like it was terrible to use my youth and pity-value to convince someone to actually buy my product (which is actually pretty illogical because everyone loves Girl Scout cookies). Most of all I was pretty shy and self-conscious at that age, and I feared rejection. So I became what I’ll call a Girl Scout dropout after fifth grade. Pretty rebellious, I know.

When Diana Kander challenged me to sell people something last week, I once again felt like a terrified 11 year old, doomed to never earn a cookie badge. Kander challenged me and student Kara Tabor to turn $1 into as much money as we could in one hour. I was worried. First of all, I have no skills that easily translate into a product. I can’t sing or dance or play guitar. Secondly, I just didn’t want to bother people with whatever product I could come up with. After all, I didn’t want to bother people with cookies, which I already noted, is illogical.

After a lot of brainstorming, Kara decided we should sell haikus to strangers. Both of us can count syllables on our hands and we can write fairly well. We thought maybe people would pity us. It turns out pity is not a good business model. We only made $2.37, but I also gave a homeless man $2 for a sandwich, so we really only made 37 cents (So far I have only lost money on these challenges like last week when I gave away $5). But, I am happy to say that I learned an incredible amount from the hands-on experience and talk with Kander afterward. I can’t say that I will ever allow my daughter or any future generations of mine to participate in Girl Scouts anytime soon (I’m mostly joking), but I am much less intimidated by the selling process. Here are some of my top takeaways from the conversation with Kander:

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Kara Tabor and I set out to make as much money selling haikus as we could in an hour last Friday, May 2. My favorite haiku from Kara reads,”You are sweeter than a baby panda eating tons of Nutella.”

1. Your skills don’t matter

One of the most insightful things Kander explained post-challenge is that it is most important to focus on what people want when selling a product. My approach for this second challenge was to brainstorm all the skills I had and then try to force people to want my “best” skill. However, that approach doesn’t solve a problem for people. People don’t need haikus. Sure, we made some people laugh and we got some pocket change, but profit can’t be made from a product that doesn’t solve a consumer problem. Kander told us that she had seen students make $100 in an hour by focusing on the customer. For instance, students selling back rubs or challenging people to bets solved problems of stress and free time.

2. Don’t convince someone they have a problem

Even if a seller thinks they’ve identified a problem a consumer has, it doesn’t matter if the consumer isn’t aware of it, Kander said. Kander explained that just like there are different intensities of headaches, there are minor and extreme problems. A seller will only be able to sell a product well if the consumer can’t ignore a problem they have. This means that the consumer also has to have the desire to fix the problem. They have to have taken steps to solve the problem, and, better yet, they have to have money set aside to fix that problem. Without the combination of these variables, a product is very hard to sell, Kander said.

3. Your market isn’t everyone

Not every customer will recognize a problem, want to solve the problem and want to pay to fix the problem. This means that inevitably, the target market for a product is not everyone. This also means that consumer problems are incredibly specific and unique, and that marketing to broad demographic groups doesn’t not work. Kander said that the best way to sell a product is to focus on an consumer archetype and sell to a category of people in which 99 percent of the group are potential customers. That is a true target market.

Once again all of these lessons can be applied to journalism as well. I especially think the lesson on target markets would be interesting to implement in a newsroom. What if we talked to a specific archetype of readers before a story pitch meeting and then tried to write a story an extremely high percentage of that niche group would read?

Sneak peak: 

Over the next two weeks I will be interviewing the founder of a young startup about their business. I will ask them all of the hard questions I’ve learned from Kander. Then, I will talk with at least five people they describe as their target market to see if they’d actually buy the product. I’m really interested to see the result of this challenge.

This week I will also be talking to young people about their phone use habits in an effort to see what news companies could be doing differently to solve their problems.

Updates to come!

Sarah Poloroid Two

Proof that I was once a Girl Scout. Here’s me with my lovely mom.



Entrepreneurship Challenge is a new miniseries that will differ from my typical blog posts. In these posts I will experiment with my interest in entrepreneurship in a hands-on way. Over the next few weeks I will blog about every “challenge” given to me by local entrepreneur Diana Kander. Kander and I connected on Twitter, and after further discussions, she offered to give me entrepreneurship challenges and then meet with me to talk about them. I will comment on my experiences and discuss the lessons I learn about entrepreneurship and media entrepreneurship in this series

About Diana Kander:  Kander is a Columbia-based entrepreneur and a Senior Fellow at the Kauffman Foundation. She is also the author of  book called “All In Startup” which emphasizes the importance of teaching students about entrepreneurship through hands-on practice.