What fighting in the woods for $500,000 taught me about supporting female entrepreneurship.

Ilana Ben-Ari
7 min readNov 22, 2016
SheEO Purple Carpet Event — photograph by Dahlia Katz

Originally published on Yonge Street Media

“Just two weeks ago, Ilana Ben-Ari, founder and CEO of Twenty One Toys spent the weekend with four other female CEOs, in the woods, negotiating for her portion of half a million dollars. Ben-Ari emerged as one of the five winners of the SheEO Radical Generosity Fund, which meant access to a $500,000 interest-free loan, spearheaded by serial entrepreneur Vicki Saunders, and funded by 500 women from across Canada who contributed $1,000 each to the fund.

As we celebrate International Women’s Day and hear about extraordinary women making a dent in the world, here’s a first-person account of what it takes to be an entrepreneur, build a company, and access the resources you need: mentorship, capital, and support. Ilana Ben-Ari agreed to share her thoughts on female entrepreneurship and fighting in the woods for $500,000. “

By: Ilana Ben-Ari, special to YongeStreet

I went into this weekend in the woods with a bit of hope, a lot of pessimism, and my guard up. What kind of strange social experiment was this? After finding out that we were one of the winners of SheEO Radical Generosity back in December, I had two months to prepare for what I assumed would be a battle. I was told I’d be going to the woods for three days in February, meet the other winners, get to know them and negotiate. The twist? We would have to decide how the funds would be divided. It couldn’t be split evenly, and it couldn’t all go to one venture.

Each person I spoke to about this looked at me, confused. Friends asked me, “Why would they make you do that?!” I was equally worried about the possible cage-match that could ensue.

What happened that weekend, and since, has completely changed my outlook towards what negotiation, collaboration, and empowerment can look like.

My weekend in the woods

I met the other winners, Abeego, LunaPads, Skipper Otto, and MagnusMode, in the car ride to the beautiful heritage farm we would be sleeping, eating, and negotiating in. It was a huge relief to get to know the other women, all intelligent, passionate people building companies with missions to make the world a better place, and making money doing it. These were my kind of entrepreneurs. We were also sharing rooms. Terrifying.

When we arrived at the farm we were introduced to Vicki, and our venture coaches, Loren Walsh and MJ Ryan, who would facilitate our weekend and help prepare for our Sunday negotiations. They brought experience, respect, and a wonderful calmness to the process.

SheEO winners en route to their weekend negotiations.

The following Saturday, Loren and MJ ran us through exercises that investigated our leadership styles, business models, and current challenges. We even had a session on negotiating, that included a chart listing our unique negotiation styles based on a survey we had taken weeks before.

Collaboration is the New Competition

We entered into that negotiation room Sunday morning, nervous, optimistic, ready to listen, and prepared to make our case. We opened up our financial statements, revealed our vulnerabilities, and, to my surprise, instead of fighting, we collaborated. Instead of vying for winner-takes-all, we advocated for each other. Instead of taking advantage of each other’s perceived weaknesses, we worked hard to make sure that everyone got what they needed.

When we made our initial asks, the total came to almost $900,000. We paused and one of the entrepreneurs in the room said, “Okay, what is the one thing that would change your business? How much would that cost and what would that bring in?” We ran our numbers again and our total came to under $500,000. In contrast, we also asked one of the participants if she had been completely honest with the total she needed during the follow-up ask. We didn’t take advantage; we pushed her to ask for what she really needed, and she upped her ask.

This negotiation by collaboration completely shook my perception of what competition could look like. We worked hard for our own businesses, but for each other’s as well. This was not a grant, or a charity. This was a serious loan, an investment, and a promise. A promise that we would make ourselves, and those 500 women, proud.

With that money, the projected increased revenues for our five businesses came to 2.5 million dollars in just 12 months. With that money, the ventures will be able able to hire new team members, go into production, launch new products, equip their factories, and reach new markets.

For my company, Twenty One Toys, we were able to get the investment we needed to take our Empathy Toy — already in 43 countries, over 1000 schools, and over 30 post-secondary institutions, — and stabilize our manufacturing, move our contractors to full-time payroll, hire, and start a global initiative to train 1000 educators and corporate facilitators around the world in play-based empathy education, teaching others how to teach empathy, even in boardrooms.

Why My Mother is Proud

I grew up in a very empowered home. Our house was a Barbie-free zone. Both my parents referred to themselves as feminists, my mother kept a “female heroes” scrapbook for me and my sister. She also edited and re-wrote the endings to most of our kids books — In Goldilocks Papa Bear was cooking and Mama Bear was fixing the broken chair. In Beauty and the Beast, Belle recognized she was in an abusive relationship, and instead of fixing the Beast with her “love,” she left.

All of these rewrites gave me and my sister the impression that we could, and were allowed to, do anything. It wasn’t until I started a business, just over three years ago that I realized what being a “woman” in the business world meant. From early meetings, where people assumed any male standing next to me was the founder of my company, or at the very least that we were married. To going to the bank and having the teller flirtatiously comment on the amount of money in my account. These still seemed minor to my own internal struggles. The constant balance of pushing for what I wanted, while still trying to be likeable, respected. As the business grew, I noticed moments where I gave up my power; hints given — small and big — that I should concede:
‘Don’t come off as too pushy. Be sweet.’
‘You’re not experienced enough to speak to business. You’re just being asked because you’re a woman’
‘Don’t let them see you cry’

It wasn’t until I met with other female entrepreneurs that I realized it wasn’t me that needed fixing.


The SheEO Radical Generosity Fund is not a charity, it’s a new model of funding female entrepreneurs. We live in a “speculation economy” where the VC model is to invest in 10 “unicorn” companies, and if one succeeds it’s considered a success. While women are starting businesses at twice the pace of men, venture capital funds less than seven per cent of female-led ventures.

It’s not about changing women’s behaviour, it’s about creating a new way to fund women-led businesses, by using peer-based, collaborative, crowdfunding models. SheEO’s initiative is just the beginning. Vicki has a favourite quote by Buckminster Fuller on this kind of change: “You never change things by fighting the existing reality. To change something, build a new model that makes the existing model obsolete”. Hopefully one day soon we can create and access alternative funding options, for many marginalized communities, regardless of gender.

The single most powerful moment for me came after the weekend. Not only were we receiving this incredible fund, we were now connected to an incredible network of hundreds of women.

The day after the negotiations, we sat in a room with 80 activators, including SheEO partner BMO bank, talking about how we can best support more female-led businesses. We spent our evening at the SheEO gala, where women from across Canada flew in to celebrate and support each other. The weekend culminated with an unconference held at Ryerson’s Digital Media Zone with over 100 women, from every sector, discussing how we can better support other entrepreneurs, not just the five SheEO winners. These women put in their money, time, and brainpower to come up with more ways we could all help each other. Women helping women.

SheEO Unconference

As I sat in that room on the last day of this event sprint, I felt so proud of my mother and all of the work that she did so that I could be in that room. These women, like my mother, are re-writing all the books. They’re rewriting history.

If you’re interested in joining SheEO, please consider becoming an Activator. If you run your own business, please consider applying for the next round of funding.

You might just regain your optimism.

Originally published on Yonge Street Media



Ilana Ben-Ari

Toy designer turned social entrepreneur, founder of @21Toys and #EmpathyToy #FailureToy inventor — https://ilanabenari.com/