These aren’t my pants — and other ways I’m bootstrapping my way to the top.

Ilana Ben-Ari
9 min readDec 13, 2016

These are photographs of me at various events that I’ve spoken at. None of these outfits are mine. The pants are my sister’s, the shirts my roommates’, and the dresses are my old friend and roommate’s, Akua’s. She’s famous now, so it’s fine.

There are a lot of secrets when it comes to starting a business. The first secret I discovered when I started my own business, designing toys that teach empathy and failure, was that entrepreneurs barely pay themselves for at least the first few years. That’s because we are merely vessels, dare I say, train stations for money. As sales increase, more money comes through your station, but it’s not stopping. It has places to go, people to see, talks to give. You are merely waving to it on its way through your station. Wishing it luck, and hoping it comes back. Maybe it even brings a few friends with it when it returns. Making the train stop when you’re just beginning means it won’t go towards other things. Things that are far away and hard to get to otherwise. So you keep waving at your money, saying hello and goodbye, and working until, one day, hopefully, the train makes a stop at your station.

That day still hasn’t come for me.

When I used to have pants

In 2010 I quit my job as a lighting designer, moved in with circus performers in an old theatre space in Montreal, and got a $1,200 artists grant to make toys and teach myself how to start a business.

I had no idea what I was doing but I was determined. I decided I could make it happen as long as I told every person I met what my plan was: I was going to change education with toys.

A few years earlier — in my thesis year of Industrial Design at Carleton University — I had designed a toy that taught empathy and what I referred to as “creative dialogue”. I had originally designed it as an aid for the Canadian National Institute for the Blind to bridge the social gap between visually impaired students and their sighted classmates and, in the process, I discovered it was just as challenging and rewarding for sighted adults. My blindfolded puzzle game ended up winning Best in Show at a prestigious design competition for recent grads and I pursued the most obvious next step — I tried to find a company to buy the idea.

With the former President of the Canadian National Institute for the Blind, Euclid Herris, at my design graduation exhibit.

That didn’t turn out so well since there weren’t too many companies looking to buy toys that teach empathy. So I shelved it for a few years, moved to Montreal, worked as a furniture and lighting designer, and worked three other jobs to pay off my student loans. The toy, however, kept coming back to me and I couldn’t shake it. At the same time, I was getting more disheartened with my work — I didn’t study design so I could make fancy furniture, I studied design to make the world a better place. I became more and more interested in this term “Social Innovation” and more and more obsessed with the website TED. I especially couldn’t stop thinking about Sir Ken Robinson’s TED talk “Do Schools Kill Creativity?

It resonated with me because growing up in Winnipeg I was a really good student. Mostly because getting a full scholarship was my only way out of Winnipeg, and into what was considered the best Industrial Design program in Canada. So I worked hard, got my scholarship, and then discovered being good at school had almost nothing to do with being good at life — or work for that matter.

Now, four years after officially starting Twenty One Toys, I know the challenge that every school and office is facing with the future of jobs — that in the next 5 years, 35% of the top skills necessary for the workforce aren’t aligned with the skills we’re teaching, or the skills we’re hiring for. Companies like Google don’t even ask for GPA or test scores from candidates anymore… because they don’t correlate at all with success at their company. But I didn’t know that yet, I just knew I wasn’t happy and I wanted to somehow help “fix” education.

So I started searching for work that combined design and social innovation, but it wasn’t simple. Eventually, it dawned on me that I had to start my own social enterprise with design at its core. What I was trying to do with the Empathy Toy in education was so strange and unknown; I knew no one else would understand it enough to make it work — so I designed a company to bring my ideas to life.

I’ve got $1,200 — I’m rich!

The artists’ grant I received in 2010 was for $1,200. It paid for a website where I wrote about my research and answered questions around design, which cost $400, thanks to my friend Anna, who cut me a deal. It was more like a blog of my research and ideas, but what I didn’t realize at the time was that I was building my SEO strategy. I used the rest of the funds to pay for prototypes made at my friend Harvey’s jewelry studio, and the rest went to two conference tickets: one for BitNorth, an unconference in the woods of Quebec, and the other for The Feast in New York. Both conferences not only opened my eyes to the incredible work engineers, designers, and entrepreneurs were doing to make the world a better place — it also was the beginning of my acceptance that I wasn’t just a designer, I was a design-entrepreneur.

My first big break happened thanks to one of the requirements of attending BitNorth — to attend you had to present. So I presented my toy and my vision of what I was trying to build, and one month later, I was lucky enough to get booked as the first TEDx speaker in Montreal.

The day after my TEDx talk I moved to London, UK, to start an internship at a “socially motivated design consultancy” called Design Against Crime, which worked out of Central St Martins College of the University of London. I took the internship to essentially find out what “socially motivated design consultancy” even meant. Working there helped me to discover one model of building a socially motivated company with design at its core. They created design solutions, like bikes with built in locks, so if you break the lock you break the bike — rendering them unusable when stolen. They came to these solutions by talking to both the “users” and the “abusers” — meaning cops and “criminals” — a.k.a: empathy!

I then ended my European summer in Finland, at a startup accelerator called StartUp Sauna, a program to give startups guidance, without investment or equity, in the woods of Otaniemi. I was one of 2 women in the program, supported by coaches, many from Angry Birds (their office was only a few minutes walk away). My goal while there was to get one of their coveted €15,000 — €25,000 grants to finally launch my business, and in the final week — I got it. Unfortunately, only a few weeks later, unforeseen circumstances meant I had to return to Canada prematurely, and I had to give up the grant.

A typical day at StartUp Sauna in Finland. FYI — Those ARE my pants, shoes and jacket. Purchased before quitting my job.

I don’t have €25k — I’m broke!

I came back to Canada defeated and broke. I’d spent the last of my savings working to win that grant, and now I had nothing. One of my best friends convinced me to move in with her in Toronto. She said I could sleep on her couch, borrow her clothes and sneak into her workplace at the Centre for Social Innovation until I got back on my feet. So I slept on her couch for months, sneaking into every education conference I could, bouncing around between Montreal and Toronto. I gatecrashed more events, kept writing in my blog, and started getting requests to use the toys in youth programs in Uganda and Trinidad. I went back to Harvey’s studio in Montreal, made 8 more prototypes. Sanded them in another best friend’s lab, and sent them on their way.

Then, just a month after publicly announcing the name Twenty One Toys, I made my first official toy sale to a school board in Toronto. Thanks to a consultant I met at one of those unconferences, a school board found my TEDx talk on Twitter and put in a pre-order for 30 toy sets. I nervously asked: “Great! Can you pay in full and wait 5 months for me to manufacture?” They agreed. The following weeks we won 4 awards — The Centre for Social Innovation’s Youth Agents of Change Award (free rent and mentorship!), the C2MTL Emerging Entrepreneur Award (exposure to an incredible community), the Youth Social Innovation Capital Fund (a 2-year $10k loan), and the Spin Master Innovation Award (a joint award between Spin Master Toys and Futurpreneur)(a 4-year $50k loan with mentorship). I bought pants immediately.

Why I’m still not wearing my own pants

That was over 4 years ago. I’ve managed to continue bootstrapping my business through a combination of award loans, pre-orders, my personal lines of credit, and now sales. While 4 years seem like a lifetime, that’s early days for a business; we’ve had plenty of bumps along the way, and lots of moments where I thought we wouldn’t make it. The statistics are scary. Inc. Magazine says it best: “25% of new businesses don’t make it past year one… 50% of all new businesses fail within five years.” But, on the bright side, that same article said “only 10% of the business[es] that make it past year 5 will die off in the following year, and only 6% in the 10th year… Rather than try to go for broke in the early years, consider building your foundation so that you can take greater risk in outlier years when you do have the safety of an established business to fall back on.”

What bootstrapping means to me is that I am still building that foundation, and keeping costs as low as possible. We’ve gone into production 4 times, and the first 3 were through pre-orders, either from a few big customers or a successful Kickstarter campaign. I’ve taken short-term loans from friends, maxed out credit cards to make it past tough months, and — most recently — the SheEO Radical Generosity fund helped us go into our 4th production run early — and we were only out of stock for a month. We’ve won 16 awards to date (you can find some of them here) and our Empathy Toy is now in 45 countries, 1,000 schools, and 100 offices. I have an incredible team and we’re growing! For now, I’m still just a train station for money. Every time we make a sale, we need to make more toys. Every time we grow, we need to hire more people, pay more rent, and buy more insurance. I’m still not on payroll, but getting closer — as in, January of 2017 closer…

“Don’t give up. Beginning is only hard”

Before I started a business, when I heard the term entrepreneur or “businessman” I would picture Robin Williams in HOOK: at his son’s baseball game, on his cellphone, being a bad father.

What I see now is my grandpa, who bootstrapped his own business with my grandmother for almost 70 years. I never called them bootstrapping entrepreneurs, but that’s what they were. They retired just last year and this was the best piece of advice I’ve received:

My grandfather, giving me advice on my growing business: “Don’t give up. Beginning is only hard”

What does bootstrapping really mean? It means it’s YOUR boots and, most likely, other people’s pants. It’s also worth noting that not everyone even has the privilege of borrowing pants. I don’t have investors, but I do have an incredible support system of family and friends, who lend me couches, clothes, and even donate trips and computers along the way.

So the next time you see a bootstrapping entrepreneur, cut them some slack, and maybe buy them a coffee, or lend them a pair of pants, or a couch to crash on while they wait for their train to come in. It’ll make a world of difference.

Want to connect? I’m trying out an experiment where I host a virtual #coffeetawk once a month for people from around the world to connect and ask me anything about business, the design process, and how they might be able to self-finance their own startup.



Ilana Ben-Ari

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