Six months ago 500 women radically changed my business, and put one more crack in the glass ceiling

Ilana Ben-Ari
7 min readNov 22, 2016


Photograph of the SheEO Radical Generosity 2016 recipients: Abeego, LunaPads, Skipper Otto, MagnusMode, and Twenty One Toys

Six months ago I was one of five winners of the SheEO Radical Generosity Fund. You can read “What fighting in the woods for $500,000 taught me about supporting female entrepreneurship” to get the whole story, but the shorter version is that 500 women took a gamble on me and my company (and 4 other female-led businesses) to prove that we need to change the ways in which we support female entrepreneurs.

Led by Vicki Saunders, SheEO is on a mission to support female-led (and female-identified) companies dedicated to making the world a better place. In late 2015, SheEO’s initiative saw 500 women (known as Activators) donate $1,000 each, creating a pool of $500,000 to lend to 5 businesses through an interest-free five year loan. This year SheEO is looking to match or exceed that number; for every 100 Activators who donate, another female-led venture can be supported.

A bit about me

I started my business, Twenty One Toys, four years ago. Wedesign toys and workshops to teach empathy, failure, and other 21st century skills in schools and offices worldwide. When I applied to be a SheEO venture, our Empathy Toy was already in over 1000 schools, 100 offices, and 43 countries. The team consisted of me, two full-time staff members and one part-time contractor. I’ve been bootstrapping since Day One, so all of our successes have been thanks to pre-orders and sales made through word of mouth, a ton of hard work, and a combination of award loans and my personal lines of credit.

I saw SheEO as an opportunity to grow our team, help with the (already huge) financial strain of our high cost of production, and allow me to better strategize and dream big(ger) — a difficult task to achieve when cashflow is a constant stress, you live with 6 roommates, you still borrow friends’ clothes for speaking events, and you’re working 16–18 hour days.

Now six months after our Radical Generosity win, I’ve finished our 4th production run, hired another full-time staff member, expanded our business model to teach empathy via online training to businesses around the world, and most recently received an honour from the mayor of Winnipeg for the work our Empathy Toy is doing to reduce racism and bullying in high schools.

Where I was when history wasn’t made

With so many successes to celebrate thanks to the support of these 500 women — who have made such a difference to my business without having even met me — it seemed bittersweet to see the events unfolding after the most recent US election. No matter where you live in the world, or stand politically, many of us in this space were expecting to see a historic event on November 8th with the election of the first female US President. Seeing a woman in that position of leadership would have been a huge symbol of our progress, hopefully normalizing the image of women in positions of power, independence, and authority.

Only a few hours after the election results came in I happened to be on a panel at a Women’s Entrepreneurship conference hosted by the Government of Canada — and coincidentally, moderated by SheEO founder Vicki Saunders.

That morning, the conference was one of the more surreal places to be. As an event organized to celebrate and support women, I’ve never felt such a mixture of anger, grief, unity, and determination. Most of the attendees and speakers were sleep-deprived, having spent the night unable to turn off the TV as they watched the results come in. I stayed up until three in the morning, which was just long enough to know the outcome. I spent my prep time in the green room watching the beginning of Hillary’s concession speech on Vicki’s smartphone.

Being there with Vicki, six months after joining this community — a community she created only one year ago — I was overwhelmed with this feeling of resilience. What we’re all trying to do is really hard. Not just everyday hard; more like put-everything-on-the-line-don’t-sleep-for-months-smile-and-take-criticism-and-feedback-and-still-get-up-everyday-and-try-to-make-the-impossible-possible hard. I’ve had days where I’ve woken up to a huge contract with a school, followed by a manufacturing emergency, with 30 minutes to prepare before a keynote presentation, and then at the end of my 16 hour day, all I can think about is whether the coffee stain on my shirt was visible from the stage. Photographs from the event seem to indicate that yes, yes it is visible.

Starting a new business is one of the hardest things you can do. It’s hard to create, it’s hard to finance, it’s hard to convince others to come for the ride, be your first customers and supporters, and it’s hard to have everyone watching you while you’re doing it. It’s even harder when you’re not what people expect a founder and CEO to look like.

Change the default

So often I’ll walk into a boardroom, bank, or meeting and people assume that the man standing next to me is the founder and CEO of my business, or at the very least that we’re partners. Just two weeks ago I went to a book launch featuring Twenty One Toys’ story. Two paragraphs in, one of my contracted male employees was credited as my business partner. This is the third time that another man working for me has been given credit for co-founding my business. The default for who is the entrepreneur in the room stills seems to be ‘the guy in the room’. My new strategy to combat this is to start by giving default ownership of a company, not to the man in the room, but to the person who looks the most tired.

Changing our default takes time. It also takes a lot of hard work. Right now the majority of investors look a certain way, and they are more likely to invest in others who look like them. When it comes to Venture Capital, it’s very clear: only 4% goes towards women. SheEO is not just about investing in female-led ventures; it’s also a great starting point to encourage more women of various backgrounds to be investors. By encouraging diverse investors, we change who receives the investment. That’s how we change the default.

“Vulnerability is the birthplace of innovation, creativity, and change”

This is a quote that has stuck with me over the years. First said by Brene Brown, I heard it quoted by my friend Kameelah Mu’Min Rashad, Founder of Muslim Wellness Foundation while we were studying at a Fellowship together.

I always go back to this quote when things are feeling particularly tough (like, trough of sorrow tough). Starting a new business — or, say, running for president — trying to be the “first,” is one of the toughest and most vulnerable things you can do. Putting yourself out there and having the courage to bring others for the ride, it’s easy to lose touch with the bigger picture and feel just utterly defeated when things don’t work the way you expected them to.

For anyone who is trying to do something for the first time, it’s going to be an uphill battle, with a lot of bumps, mistakes, and learning along the way. Some revolutions take a lifetime. A messy, relentless, disappointing at times, and incredibly uncomfortable lifetime. But change does happen — if we pick ourselves up, knock on more doors, crack more ceilings, and hold each other accountable to being radically generous, and radically courageous.

So, while I’m still trying to make sense of current events, I’m planning on doing what I can to put just one more crack in the glass ceiling and change our default. I’m now a SheEO Activator and I’ve handed over my $1,100 to support women who are building companies to help us foster a better world. ’Cause I sure as hell am not waiting for some guy in a suit to do it.

So, if you want to play a small but significant role in the life of a female-led social business, please join us. Deadline to apply and/or become an Activator is November 30th.

Still reading? Want to know how an interest free loan changed my business? Here are the details of what has happened in the past six months:

  • Manufacturing: With a portion of the loan we were able to go into production early, for our fourth production run. Consciously building without investors, our Empathy Toys have been ethically mass manufactured, and delivered to over 45 countries — entirely bootstrapped, with a combination of loans and pre-orders. Using a portion of the funds from SheEO, we were able to double our order, start early, and avoid running out of stock before we could fund another run (as has happened in the past)
  • Growing the team: We hired our new Director of Partnerships and Learning, expanded our reach into schools and organizations and, for the first time, we have someone on the team — other than just me — working and executing on our business development.
  • Expanding our business model: We’ve launched online and in-person training to help educators across the globe design our Empathy Toys into hundreds of curriculums and companies’ training and development departments.
  • Community: 10% of our new clients have come from referrals in the SheEO Activator community ranging from the banking sector and insurance, through to school boards and universities. Activators have made introductions, as well as offered support and advice on anything from legal to marketing to strategy.
  • Financing: After four years, I can finally start talking to banks about getting a business line of credit, getting myself on payroll, and weaning myself off financing the business with personal credit cards and lines of credit.
  • Our impact: With all of these pieces coming into place, we were able to celebrate our impact! Just this month CBC did a feature outlining how MBA programs are now teaching empathy with our toys, and our most recent honour from the Mayor of Winnipeg for the role our toys have played in reducing bullying and racism at schools across Winnipeg.

Want to chat? I host a virtual #coffeetawk once a month where you can ask me anything about my business and design process, and how I’ve been self-financing my own toy startup.



Ilana Ben-Ari

Toy designer turned social entrepreneur, founder of @21Toys and #EmpathyToy #FailureToy inventor —