Social Impact Heroes: Why & How Brian Weisfeld of The Startup Squad Is Helping To Change Our World

Yitzi Weiner
Dec 11, 2020 · 9 min read
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Leadership to me is setting a course, empowering and inspiring a team, and removing obstacles in their way. I’ve been fortunate to work with CEOs of companies from startups to publicly-traded companies. The CEOs I supported were able to make the leap from startup founder to IPO because of their ability to transition their role from do-er to leader. They set a course for the company, hired great people, and provided those people with the responsibility to run their teams while helping them overcome any hurdles.

part of my series about “individuals and organizations making an important social impact”, I had the pleasure of interviewing Brian Weisfeld, Founder and Chief Squad Officer of The Startup Squad.

Brian Weisfeld has been building businesses his entire life. As a kid, he bought gummy bears, sorted baseball cards, babysat, and sold mixtapes. As an adult, he helped build well-known, billion-dollar companies including IMAX Corporation and Coupons.com. But after watching his oldest daughter struggle to sell Girl Scout cookies and getting frustrated at the lack of empowering influences for his girls, Brian decided to create a movement to inspire girls to open their first businesses and to empower them with an entrepreneurial mindset. Brian is the Founder and Chief Squad Officer of The Startup Squad, an initiative dedicated to helping girls reach their potential and follow their dreams, whatever their passions, and is the co-author of The Startup Squad, a Macmillan-published children’s book series. Brian lives in Silicon Valley with his wife and two daughters.

Thank you so much for doing this with us! Can you tell us a story about what brought you to this specific career path?

ve spent my career helping entrepreneurs scale and build their businesses. I was part of a three-person team that bought IMAX Corporation in the early 1990’s and helped to transform it into the company that it is today. I moved from New York City to Silicon Valley in the late 2000s to be the COO of Coupons.com and helped build it from a 100-person startup to a 500-person IPO-ready company.

After I left Coupons.com, I watched my then eight-year-old daughter attempt to sell girl scout cookies and run a charity bake sale with far more enthusiasm than knowledge about how to market and sell a product. A few months later, I was reading books with my girls and found myself wishing that there were more empowering influences for them (I had been forced to read my girls one too many pink, princess, fairy, unicorn, rainbow books!). At that moment, I was struck by the inspiration to create The Startup Squad, a novel series and movement to inspire and empower girls through entrepreneurship.

Can you share the most interesting story that happened to you since you began leading your company or organization?

I’m a business person, not a writer, but I knew I wanted to launch this brand and movement with a novel series for kids. Learning how to write for kids was the hardest and most humbling thing I ever did in my career.

Early in the process, I had the opportunity to submit the first ten pages of my manuscript for a critique from an editor at a publishing house. I knew deep down that meeting the editor was going to lead to a book deal. I excitedly walked into the meeting with high expectations but the critique was brutal. The editor pulled no punches whatsoever. Referring to the dialogue I had written between two of my girl characters, she said the dialogue was so unrealistic that she was surprised to learn that I actually had children! She was, in a very direct way, telling me I had no business trying to write a book and that my goal was unachievable. Well, few things motivate me more than being told that it can’t be done so I redoubled my efforts, training, resources, and dedication and was ultimately able to sign a three-book deal with Macmillan.

The punchline is that a year before my first book came out, I met that same publisher at another event. I re-introduced myself to her by thanking her for giving me the kick in the pants I needed at the exact time that I needed it. She was extremely embarrassed to be reminded that she had been so direct. But I explained to her that I was truly thankful for her directness as it was a wake-up call that I needed. She asked how it was going and when I told her about my publishing deal, she gave me a high-five and seemed truly happy that I had overcome all the rejections and naysayers (including her!) to make it happen.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I shared an early version of my manuscript with a number of beta-reader girls to get their feedback. One eleven-year-old-girl pointed out a grammatical error that I had made over one hundred times in the manuscript. She schooled me! The lesson learned was that as I entered the uncharted waters of a new field I was going to need a lot of help. I had to be comfortable accepting help from anywhere and anyone. Even a fifth grader.

Can you describe how you or your organization is making a significant social impact?

The Startup Squad has started a movement to inspire girls to open their first lemonade stand or other business and to empower them with an entrepreneurial mindset. Girls across the country have been inspired to start their first businesses as a result of our efforts.

We want all girls to develop an entrepreneurial mindset, so we’ve worked with a number of charities across the country to instill an entrepreneurial mindset into girls who might not otherwise have access to it.

We worked with a community center in Kingston, NY to create an entrepreneurship pilot program for their underserved girls. A local female entrepreneur led a group of eight-to-ten-year-old girls through an entrepreneurship program in which the girls developed their own line of t-shirts. Each week the girls were visited by other local female entrepreneurs who described their profession to the girls while reinforcing the business topics discussed that week.

We partnered with Girls Inc of NYC to develop a program as part of their economic literacy efforts. We raised enough to donate ten thousand copies of our first book to their girls, 65% of who come from families with a household income of $30,000 per year or less.

We developed a program to apply the story and lessons of The Startup Squad books to help girl scouts get more excited about and do a better job at selling cookies. We’ve worked with hundreds of girl scouts across the nation including one troop that was made up of girls who live in a homeless shelter in Jamaica, Queens.

Can you tell us a story about a particular individual who was impacted or helped by your cause?

We ran a girlpreneur market and invited 25 girls to sell their wares. One of the girls had a beautiful display; she was selling a wealth of goods that would fit in at a boutique in any major city. She had hand-made candles in glass candleholders, tie-dyed shirts and totes, and much more. I was blown away by the quality and breadth of what this 11 or 12-year-old girl was selling. I asked her if this was her first business and she said, “no, it’s my second.” I asked her what her first business was and she told me that she once ran a lemonade stand. I turned to her mom and asked how her daughter was able to go from a lemonade stand to such an amazing variety of boutique quality products. Her mom said, “you spoke at her school and inspired her to do it.”

Are there three things the community/society/politicians can do to help you address the root of the problem you are trying to solve?

We are trying to create the next generation of female leader. The Startup Squad’s goal is not for every girl to grow up to be an entrepreneur, but rather we believe that girls with an entrepreneurial mindset (who are comfortable with risk and failure, see opportunities instead of problems, have a growth mindset, etc.) will be more successful in life regardless of the path that they choose. We believe that girls with an entrepreneurial mindset will grow up to be better teachers, doctors, parents, CEOs or whatever path they choose to follow.

Three things that will help empower girls are to increase entrepreneurship education in schools so girls and all kids can develop that mindset, provide more opportunities and fewer restrictions for kids to start businesses (amazingly kids’ lemonade stands are still technically illegal in many states including New York and California), and continue to drive the growing movement to invest in, mentor, and support female entrepreneurs.

How do you define “Leadership”? Can you explain what you mean or give an example?

Leadership to me is setting a course, empowering and inspiring a team, and removing obstacles in their way. I’ve been fortunate to work with CEOs of companies from startups to publicly-traded companies. The CEOs I supported were able to make the leap from startup founder to IPO because of their ability to transition their role from do-er to leader. They set a course for the company, hired great people, and provided those people with the responsibility to run their teams while helping them overcome any hurdles.

What are your “5 things I wish someone told me when I first started” and why. Please share a story or example for each.

You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

The U.K. government recently commissioned what has become known as the Rose Review to study female entrepreneurship. The report suggested that up to £250 billion of new value could be added to the U.K. economy if women started and scaled new businesses at the same rate as men. In response, the U.K.government has announced an ambition to increase the number of female entrepreneurs by fifty percent by 2030, equivalent to nearly 600,000 additional female entrepreneurs creating untold numbers of jobs.

While the proportion of women who are engaged in an entrepreneurial activity in the U.S. is roughly three times that of the U.K, a similar movement to promote female entrepreneurship in the U.S. would create countess new jobs and economic benefit to this country and generate a lot of good for a lot of people.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

It’s actually a song lyric from the Grateful Dead song Scarlet Begonias. It reads, “Once in a while you get shown the light in the strangest of places if you look at it right.”

I did a TEDx on the topic of inspiration and I talk to kids about it all the time. You can’t wake up one morning and say, “Today is the day that I will be inspired.” Inspiration doesn’t work like that. But what you can do it put yourself in situations in which you are surrounded by new perspectives and influences while keeping your eyes open for that inspiration. My inspiration for The Startup Squad hit me while I was reading childrens’ books with my daughters in bed on a Sunday morning. It was one of the strangest of places in which to be shown the light.

Is there a person in the world, or in the US with whom you would like to have a private breakfast or lunch with, and why? He or she might just see this, especially if we tag them. :-)

I’d love to break bread with Oprah Winfrey. Oprah has spent her career inspiring and empowering people and her story of rising up from difficult and humble beginnings is an inspiration in itself. The Startup Squad is all about inspiring and empowering girls through entrepreneurship and so I’d welcome the opportunity to share our story and get her guidance and inspiration to help us reach even more girls in the future.

How can our readers follow you on social media?

You can find us @thestartupsquad on all social media platforms.

Authority Magazine

Leadership Lessons from Authorities in Business, Film…

Yitzi Weiner

Written by

A “Positive” Influencer, Founder & Editor of Authority Magazine, CEO of Thought Leader Incubator

Authority Magazine

Leadership Lessons from Authorities in Business, Film, Sports and Tech. Authority Mag is devoted primarily to sharing interesting feature interviews of people who are authorities in their industry. We use interviews to draw out stories that are both empowering and actionable.

Yitzi Weiner

Written by

A “Positive” Influencer, Founder & Editor of Authority Magazine, CEO of Thought Leader Incubator

Authority Magazine

Leadership Lessons from Authorities in Business, Film, Sports and Tech. Authority Mag is devoted primarily to sharing interesting feature interviews of people who are authorities in their industry. We use interviews to draw out stories that are both empowering and actionable.

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