Life Lessons For Kids
Raising Entrepreneurial Girls, The Startup Squad News

Three Life Lessons I Wish Every Girl Could Learn — and Why

My oldest daughter was eight when the business world came knocking at her door. She joined the Girl Scouts, and we all know what that means: cookie sales. Then, two months after cookie season, she and a friend ran a bake sale to raise money for the local food bank.

In both cases, her mission as a somewhat shy, funny little second-grader was to sell delicious baked goods. But her method? Well, that was yet undetermined—and that was, in fact, her biggest challenge. She knew she wanted to sell and be successful. She just didn’t know how.

As a business exec who’s had the fortune of helping build several world-class brands and companies throughout my career, I could have stepped in and given her a formal business plan or step-by-step instructions on how to get her fledgling baked goods businesses off the ground—but not only would that have been way too advanced, it was unnecessary. She didn’t need a business plan; she needed basic business skills. Very basic. And I was quite happy to stand back, let my wife be the mentor and watch the situation all unfold.

I knew this selling experience was going to be a significant opportunity for my daughter to begin learning the important things I wanted her to know—lessons I want every young girl to know, really. That it’s okay to fail as long as you try your best and you get back up to try again. That basic business skills will help you succeed in life even if you don’t want to be a business person. That grit and a growth mindset are essential tools for success in life no matter the path you choose.

3 Life Lessons for Kids

We taught our daughter three skills during her first foray into the business world (mostly thanks to my wife) that I would love for every girl to learn, whether she goes on to become an entrepreneur or not. Skills that will serve every child well on her journey.

  1. Life lesson: “Say good morning to get people’s attention.”

    Translation: Have a script to make conversations easier. This was my wife’s advice to my daughter as she stood at the end of our driveway, unsure of what to do while fumbling around with her boxes of Thin Mints, Samoas, and Peanut Butter Patties. She was a little wary of talking to strangers—not necessarily a bad thing, but neither is it conducive to successful selling. Even when your product is cookies. Shyness is common among elementary-age girls, so encouraging them to be bold enough to initiate conversation and prepare in advance what they want to say may be the first step in empowering them to get out of their shell and simply connect with others.

  2. Life lesson: “Look people in the eye when you talk to them.”

    Translation: Be confident. This is a tough one, right? Making eye contact with an adult can feel intimidating to a child. Notice where many kids look when they’re talking to you—at their feet, at their parents, off to the side, maybe at a friend next to them. That’s because making eye contact requires a certain amount of self-confidence, which is something many elementary-age girls lack. But sometimes you have to fake it till you make it. By instructing our daughter to look people in the eye when she talked to them, my wife knew this might feel unnatural at first, but it would help her grow in her ability to communicate confidently and effectively. And speaking from experience, my wife has perfected this skill. Trust me.

  3. Life lesson: “Make sure to tell people the money goes to charity, so even if the customer doesn’t want to buy anything, they may still make a donation.”

    Translation: Know how to appeal to your customers. During her charity bake sale, my daughter wasn’t just selling cookies and brownies; she was selling an opportunity to do good. Positioning your product and appealing to your audience is not a skill that’s necessarily innate for a grade-school kid. But when it’s learned, it can help them not only become entrepreneurs, but also help them succeed in life by knowing how to convince people to buy what they are selling (be it a physical good or a something less tangible, like their point of view).

    It also helps them recognize when others are doing the same to them. It’s about articulating your position and convincing others to do what you want them to do–an essential skill for becoming a savvy teenager: “Mom, you wouldn’t be just buying me a new car. You’d be buying your independence. I’d be getting a car, but you’d be getting your freedom from having to cart me around.” It’s a skill that could work against you—just be aware. But if your child gets so good that they’re able to actually sell you, congrats! Your kid is poised for a successful career.

This experience of watching my daughter fumble around with baked goods, trying in earnest to sell her wares but not actually knowing how, was a big part of my inspiration behind The Startup Squad. She may not grow up to start her own business, launch anything beyond a bake sale, or become a CEO. But the experience of entrepreneurship–learning those basic business skills, knowing it’s okay to fail, and learning the importance of grit and a growth mindset–will help her succeed in life no matter her passions.

These are just a few of the many life lessons I observed watching my daughters run their first businesses. I want to invite you on this journey with me, of empowering young girls to be everything they dream of—and more.

If you want to know more about my background and my vision for The Startup Squad brand, you can read more here. Otherwise, come back often! We’ll be sharing lots of tips, practical advice and valuable info about how you can encourage the young girls in your life to boldly follow their passions and live their lives like they mean business.


  • Yvette Stout

    - June 14, 2018 at 5:26 pm Reply

    Loved reading this! I whole heartedly agree. I grew into my confidence both personally and professionally over time but as a painfully shy young girl, advice and encouragement like this could have set me on my path even sooner.

    • Brian Weisfeld

      - June 22, 2018 at 12:12 pm Reply

      Yvette – thanks for the note and support. I can’t imagine a more confident and successful you – it would be unfair to the rest of us!

  • Lisa Makover Conway

    - June 14, 2018 at 10:51 pm Reply

    Hi Brian,
    I love this! As the mother of three girls and an elementary school teacher for 28 years, this message really goes straight to my heart. You and your wife sound like amazing parents and I wish you much success.

    • Brian Weisfeld

      - June 22, 2018 at 12:11 pm Reply

      Lisa – thanks for the support. I can only imagine the incredible girls that you have raised in your image.

  • Paul Willard

    - June 22, 2018 at 4:45 am Reply

    Love this, thank you for doing it! Like you, I am a double daughter dad, and my oldest just did her first lemonade stand last Fall, so this is close to home right now. Thank you for the reading list, and thank you for the coding framework advice (presumtive, I know :). Let me know if I can help too!

    • Brian Weisfeld

      - June 22, 2018 at 12:10 pm Reply

      Thanks for the support, Paul. And I am excited to hear about the next steps on her entrepreneurial journey and look forward to when she hits you up for her first seed (no pun intended) financing!

  • Lisa levy

    - June 25, 2018 at 3:24 pm Reply

    Not only are these great words of advice, but they are so practical and tangible, making them very effective and useful tips for young and old alike. I love what you are doing!

    • Brian Weisfeld

      - June 25, 2018 at 4:49 pm Reply

      Thanks for the post and support, Lisa. I appreciate it.

  • Sonali Rammohan

    - July 24, 2018 at 9:27 pm Reply

    Great advice Brian! As a mother of 3 kids (2 of which are girls), these tips ring true. Improving entrepreneurial skills will help with so many aspects of their lives as they grow into confident young women. Sonali

    • Brian Weisfeld

      - July 25, 2018 at 2:28 pm Reply

      Thanks, Sonali!

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