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Using Toys to Teach what Textbooks Can’t with Ilana Ben-Ari

Ilana Ben-Ari was working on a design-school project when she learned there was a huge social and emotional gap between the visually impaired and the sighted community. What began as a university project grew into Twenty-One Toys, which teaches 21st Century Skills with the Empathy Toy and the new Failure Toy.

In this episode:

  • How Twenty-One Toys got started 
  • Ilana’s early days of bootstrapping the company
  • The value of coaching
  • Why it’s important to teach failure to all ages 
  • How the first SheEO Venture cohort divided up the money at the Venture Retreat
  • The challenges of being an entrepreneur
  • Ilana’s favourite ways to take care of herself and how she reminds her team to do the same 

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Show Notes


VICKI: (silence)


ILANA: How are you? Hey.

VICKI: How are you?

ILANA: Good, how are you?

VICKI: Very good. Let’s have some fun!

ILANA: Yeah!

VICKI: Anything you want to talk about specifically?

ILANA: I mean, I’m going to assume that it’s going to be a combo of my story, SheEO, at what point they met me at, and then possibly, I mean, where I’m at mentally in this moment right now is all the Failure Toy. So-

VICKI: Yeah, why don’t you want to just talk about the Failure Toy? Or do you want to talk about everything?

ILANA: I’m open to wherever it goes.

VICKI: We can start now and go forward or we can go back in time and tell the whole shebang.

ILANA: Mm-hmm (affirmative)-

VICKI: Do you have a lot of podcasts out in the universe?

ILANA: I do. Yeah.

VICKI: Yeah?

ILANA: I’ve got a lot. So I do think it’s helpful to frame a little bit of the history of it and I am the most comfortable framing it as the segway into where SheEO… at what stage SheEO met me at. So I’m happy to talk about that. It doesn’t have to be the whole time, but I think that would be some parts that would be helpful.

VICKI: Okay, cool. So let’s do that. Let’s do Sheri Griffiths. Right? Like the bat thing. Just to highlight that. Toys are the new textbooks. I want something around new models, how things are eff-ed up and how we’re… you’re working towards those. I might want to talk about, we’ll see, but maybe maintaining your energy and sort of the ups and downs of entrepreneuring. Not all just sunshine and happiness.

ILANA: Yeah, I mean, that would be-

VICKI: That being hard. Yeah.

ILANA: That would be a good way to meet me where I’m at now. I’m actually in a very positive, optimistic place today. But it’s been an intense summer.

VICKI: Yeah, totally. Okay. So do you want to… I’ll just say, basically start by hi, I’m Ilana. So your name, founder of, and what is it, what is Twenty-One Toys? And then I’ll ask you to go… can you bring us up to date, five minutes or less on how you got here. Then we’ll kind of go from there?

ILANA: Yeah, sure.

VICKI: That cool? Okay. I’m going to do intro outro after. It gets lopped on. So over to you whenever you’re ready to start.

ILANA: Okay, amazing. So I’m explaining what Twenty-One Toys is and how we kind of where we… like our origin story?

VICKI: Yeah. I mean, go back as far as you want. Who are you? I’ll just ask. But so go who you are, founder of whatever, and what Twenty-One Toys is and then I’ll ask you-

ILANA: Got it.

VICKI: … did you want to be a toy designer? And then you can kind of tell your story.

ILANA: Yeah, got it. Great. So I’m Ilana Ben-Ari. I am the founder of Twenty-One Toys and the designer of the Empathy Toy and the Failure Toy. I started Twenty-One Toys, which is a learning and development toy company using toys to teach what textbooks can’t.

VICKI: Amazing. Welcome. I’m so glad to have you here today. I can’t wait for the world to know more about your story. So tell us a little bit about how you happened upon this. Did you step back and think, “I want to start a business,” and you did market research and figured it all out or… What’s your story?

ILANA: Definitely not that path. So typically I’m not linear, but especially with the birth of Twenty-One Toys, I like to joke that it was a series of escalating dares. So my story starts when I was studying design in university and I had my thesis year of industrial design, which is product design. I was tasked with designing a product initially for the visually impaired community. The project just transformed so well. It started off with this idea that I would design something that would be the brief set and navigational aid for the visually impaired community.

ILANA: I ended up changing the brief, but continuing its core elements where I started talking to and meeting with people who had visual impairment and their friends and family, what’s known as empathic research, and discovered very quickly that I could make a Blackberry with really big buttons or a lot of tech solutions, but at the core it really showed up in the conversations that I had that there was just a huge social and emotional gap between the visually impaired and the sighted community that is even more exacerbated at a very young age. So when you’re a really young kid.

ILANA: So that led me to design a toy which is now known as the Empathy Toy. But as the story goes, I designed it in my studio, I would test it during the day with visually impaired students and at night, tested it with sighted adults in my studio. That’s when I realized that the toy was just as challenging and rewarding for multiple ages and abilities. So that’s when I got the first spark that I said, “Look, this toy is actually allowing for some really rich and really deep insights into how you deal with stress, how you deal with patience, but also how you creatively communicate.” So putting yourself into another person’s shoes to solve this complex challenge. But the adults are having just as much of a challenge as the students.

ILANA: So I realized it wasn’t exclusive, it was inclusive. The toy ended up winning this best in show design award. So I did what any designer would do at that stage, which was I said, “Great, this toy won an award. Which business do I sell it to?” Then luckily no one was interested in starting an Empathy Toy company. So after a few years of just paying off student loans and I kept kind of going back to it, I thought, “You know what? I want to start my own toy company.” And it’s not your typical sort of toys. It’s really about looking back at my own experiences in education, which was the idea that I worked really really hard to get good marks and I was one of those what you call an A student. But being good at school had almost nothing to do with being good at life or work for that matter. That made me both furious, but also gave me that passion to say, “Well, what could we be teaching? What aren’t we teaching?”

ILANA: That’s where I thought, “We need to be teaching skills like empathy, failure. And we aren’t going to be able to teach that with textbooks.” So that was the first dare.

VICKI: Right. I mean, it’s so interesting because I’ve heard this from a couple of ventures in our community, specifically Be, when I think about the [Linker 00:08:22], and how it’s literally… She doesn’t like it when someone says this is for this certain group of people, right? In fact, by using this, you start to actually get more emotionally in touch with other people and how they’re not included. So that’s just such a cool insight. So toys are the new textbooks you had said way back in the day. I don’t know if you still talk about that, but I love that framing. This whole experiential approach, right? Which when you go through an experience, you have a chance to sort of rewire and rethink things.

VICKI: So I know that you are now at another stage, which we’re so excited about. You’re about to launch a whole new thing. Do you want to talk a little bit about that?

ILANA: Yeah. So I joke. I call it Twenty-One Toys. It stands for 21st Century skills. But a lot of people think it’s because I have 21 toys. So the two in 21 is silent at the moment, so we’re being a one toy company for a really long time. When we first heard about SheEO, I had gotten some amazing traction. We’re about three years in to the Empathy Toy. But I’ve always wanted to create an entire launch, like a whole line of toys, and the Failure Toy has always been the next step. So many of our conversations about empathy lead to conversations about failure and vice versa, so many conversations about failure lead to empathy. So just in the next, like any minute now, we’re about to launch the Failure Toy, which has been about three plus years in the making. So it is I am both terrified and incredibly excited right now.

VICKI: So let’s step back a bit into the creative process around this and then we can talk about the business piece after. But failure is such a huge thing. Like I personally don’t even love the word, right? It’s like everything is learning and failure is feedback and all that kind of stuff. So why is this important? Why is it important to actually practice failure with a toy?

ILANA: Yeah. Well, it’s kind of a multi-layered answer. So where I would start with, and it’s the same for empathy as it is with failure, we can all acknowledge that those are skills that we need to learn. They’re like the future job skills, not just to be a good human, but just to be a good worker, colleague, inventor. You need to really understand what those skills are. But I think when we talk about empathy and then also with failure, it’s not about just be super empathic. All you do is be really empathic. And the same with failure, especially in the startup community, we’re saying, “Fail fast, fail often,” which in certain contexts, you get the sentiment, but it’s actually quite tone deaf. And at the most, it’s actually quite dangerous.

ILANA: I like to say that I’m on a lot of entrepreneurship panels where they’ll say, “It wasn’t until I had my fourth business that that one worked.” And I was like, “I can’t afford to try three businesses and then have my fifth one work.” I think that we are just working on exchange right now. So rather practicing what I like to say is failure abstinence, which is we’re just not talking about it in school and fingers crossed, everyone’s going to figure it out on their own, to the more extreme which is we’re being asked to be innovative, creative designers and fail fast, fail often. There’s no middle ground conversation about the fact that failure means something different to everybody. It’s entirely based on context. We react to things in completely unique ways and there’s not one right way.

ILANA: So I like to say that we need to start at failure 101 and failure education. Where that starts is with self-awareness. So understanding how you deal with risk, how you deal with competition, how you deal with things like perfection. It doesn’t have to all be negative. It’s just I might, when presented with a new challenge, just dive right in and do zero planning. I might work really hard to build something and then I’m being told, “Okay, now you can restart.” I’m like, “But I don’t want to restart. I love it. I don’t want to touch it. I just figured this thing out.” There’s so many different ways that we navigate creating and inventing and iterations. And then not just do I need to understand myself, but then I need to understand the people I’m working with and then the larger context of things.

ILANA: So there’s so much room for us to have just conversations and acknowledgements and just the different ways that each person reacts to things and that’s where I think we need to start the conversation because what I hear when I hear fail fast is suppress all your emotions and feelings, don’t talk about all the awful things that you’ve gone through and just tell us about that time you failed once you have this amazing success story. That’s what I hear.

VICKI: And it’s also like the ultimate privilege, right?

ILANA: Yeah.

VICKI: It’s like, well, I just fail, fail, fail. You’ll raise more money, you’ll do the next thing. And it’s… yeah.

ILANA: Yeah. So I think some people really go, “Yeah, fail fast. That’s amazing.” And other people go, “Not for me. That’s ridiculous.” And then they just shut down the conversation. Whereas where I’m hoping and what I’m seeing with the toy that the space that we live is an in-between, in the gray zone of all of that. So we’re not saying this is the one silver bullet, this is the answer. The goal is for you to just better understand yourself when you’re under certain circumstances and there’s certain challenges and behaviors that come out.

VICKI: Okay, cool. So let’s step back to now you’re on your second toy, but let’s go back to [inaudible 00:13:45] for a sec and talk about… So you had created this thing. You had sort of tested it out. You applied to SheEO, you had already had customers, you were in a bunch of countries. How did you go to market and how have you grown that business?

ILANA: So when I first started Twenty-One Toys and with the idea of the mission, I didn’t even consider getting investors or even wanting to go down that route for so many reasons. One of them being I didn’t need someone in a suit to tell me why this wasn’t going to work. I was like, “I’m good.” So my goal from day one was I need to go direct to the consumer. I need to go direct to my user and hopefully they’ll become my customer. So the idea of toys are the new textbooks is a really good reflection of how in the first few years, it was really bad education and just about schools and education. Now we’re expanded beyond that.

ILANA: But I would take the prototypes of the empathy toy and I would essentially volunteer or break into education conferences. I would leave a toy on a table, I would walk away, and then I would just see who showed up and would say like, “Who’s toy is this? What is this?” And that would invite a conversation. That ended up getting me introduced to the superintendent of a school board in Ontario and they put in their first order. So from day one, I was bootstrapping and I was paying for production with a combination of people who paid and waited. So when that first school order came in, I said, “Great, I’m going to need you to pay upfront in full and I think it will be ready in about six months,” which I didn’t even think was a hard negotiation tactic. I was just telling them the facts. It was like yeah.

ILANA: I had some money. I had a few thousand dollars saved up for the company, but I ended up using that trying to launch it in the U.K. and then in Helsinki. So when that didn’t work out and I ended up in Toronto, I think I had like $1000 left in my bank account. So this was a moment of if this is going to work, it needs to work in the next six months. So I was at that moment when I was breaking into education conferences. I was sleeping on my best friend’s couch. I was really, yeah, really being quite scrappy. Then when I got that first order, the timing worked out that that happened at the exact same moment that we needed up I won the Spin Master Innovation Award, which was a five year award loan, which also gave us mentorship with Spin Master Toys. That just so happened to be a toy company just by coincidence. Then we started winning kind of award loans. Side note, the joke was some of the award loans, some people said their accountants looked at it and said, “You won this?” So ups and downs.

ILANA: But eventually at the point where I heard about SheEO was about three years in and I had… We had been getting a lot of traction. We went into our first mass production after our first year by doing a Kickstarter campaign. That’s how we got into over 30 countries. We got some amazing press. So Time Magazine called the Empathy Toy one of six new technologies shaping the future classrooms. So they’re saying it’s like a future technology. Then we just got international customers. So we started to get a lot of traction. Where it got really interesting was that we expanded beyond just selling toys directly. We started selling workshops. So there was traction to sell professional development workshops, not just in schools, but in HR and in towns and learning departments and also to provide training for those that wanted to embed the toys into larger programming.

ILANA: So there were all these options, but I was on maybe zero sleep. Cash flow, I had run way. Every month, I was just eating what I killed. I just had an incredibly loyal team that had stuck with me as contractors that were waiting for the next big step or big win so that I could just put them on payroll. But when I applied for SheEO, we were at such an important moment in time where I… Every time I’ve gone into production before, I had emptied my entire bank account and then just fingers crossed, holding my breath, hoping that we make that money back as quickly as possible because no factory is going to start production without a 50% deposit.

ILANA: So when I first heard about SheEO, I thought, “This would be just amazing to help with cash flow as well as I can start actually keeping my contractors, putting them on a payroll. And amazing, actually have somebody help me with following up on the traction and the corporate market while we continue to keep the momentum going with education.” What I didn’t expect was just the incredible community that I was invited into. Not just the other ventures, but the SheEO Activators. I was lucky enough that early stage experimentations, we were like the first year ventures. So we had absolutely no idea what we were getting into. But that plus the mentorship and all of that combined, it completely just changed our trajectory.

ILANA: Oh, sorry. I think it’s muted, Vicki.

VICKI: Sorry. I think-

ILANA: No, it’s okay.

VICKI: Yeah. I think one of the things that we learned from you that was so exciting, like when I was first conceiving of this idea was there are all these women out there that have a ton of experience and expertise and network connections and influence who are not connected with entrepreneurs and there are all these entrepreneurs who need to get plugged in. So this kind of two-sided marketplace idea was just that, an idea, and fingers crossed that connecting people into relationship would actually really transform things. I remember that you were one of the first ventures where people saw what you were doing and we had one of our Activators, Colleen from [Bustlers 00:19:56], came along, Colleen Morehead. She took the toy and she sent it out to five different law firms, right? And she’s like, “You guys need this. You need to figure out how to do this.” And it started to lead to things, right?

VICKI: And then one of our other Activators came along and maybe you can talk about her, Sheri Griffiths, she’s so special, and how that kind of helped you with the first monster-sized contract.

ILANA: Yeah, one of the big things when you’re running a business is I’m head down in the office. So the opportunities to actually get out there and connect with people is really challenging. So I was introduced to Colleen, who’s amazing. We connected with a number of Activators. Sheri Griffiths saw the huge opportunity for us to create an incredible impact at the Institute for Learning at the Bank of Montreal. So she was able to make a connection to [Tar 00:20:52] and Gina who are running IFL at that time and the timing couldn’t be more perfect because a lot of financial institutions talk about empathy and empathy was starting to get traction at that point. But the Bank of Montreal had actually embedded empathy into their Being BMO documents. Like this was something that they truly believed in, that they were embedding and trying to embed into all their leadership programs. But one of their challenges was how do we make Being BMO come to life? How do we bring it to life?

ILANA: What the Empathy Toy did was that it took something that they’re already trying to teach, but it make it stick and it made it resonate and it made it personal to each individual person. So right after, Sheri made the intro, but also Julie, Julie [Bergomerts 00:21:45], took a risk and said, “Yes,” to bring us in to do a workshop with very C-level people at BMO. They loved the workshop, gave it their thumbs up. So after we were introduced by Sheri to the IFL, we got a call I think within a week that said, “Can you do a 200 person, 90 minute workshop in a week?” And we said, “Yes,” and we leaned into it. That sped up. Our facilitator team went from one. We’re now at 15 people. We have a 15 person facilitation team. That not only launched us to grow out our facilitator team, but at its most, we were running six workshops not just in Canada, but the U.S. for within that… just for that one client. So they were using it so much and they were saying that it was an empathedic. Empath… We’re trying to figure it out. Like an empathy virus? Like an empathdemic or something?

VICKI: Epidemic.

ILANA: Yeah. So when I was talking with their legal department because we needed… okay, we need to rush the legal, let’s get the MSA in. They were saying how this is like a virus because they couldn’t keep track of how many people were hearing about it and then calling us.

VICKI: That’s so good.

ILANA: What that ended up leading into is by the end of that year, we had started a real conversation about, “Look, we can go in and we can run a workshop. I didn’t start this company so I could run a workshop company. I started this because I want to create the world’s first global community of toy educators and facilitators. What would it look like if we put the toys in the hands of your facilitators? We certify them and they ran workshops?” So they have reached, I think to date in just their first year, at least 5000 of their employees with the team and we haven’t run any of those workshops. Their own people have been running those workshops. So the impact that we’re going to have, it’s now a multi-year opportunity. That wouldn’t have been possible without that initial introduction and for Sheri to take that risk with us.

VICKI: Well, and this to me is really that the message underneath what we’ve done is reorganizing the resources that we have out there, right? Many people with lots of connections are not in relationship with entrepreneurs and like we’re not of the same DNA, right? All the entrepreneurs hang out with each other and are super positive about everything. It’s going to take three weeks, got it covered. And then you’re like, “Oh, holy crap. That took three months. What?” I sit with corporate people in our network and they’re like, “Oh my God, you entrepreneurs, you always… You’re so optimistic. It’s crazy.”

VICKI: But to get in this network and be radically generous with each other and create that support, it lifts everybody. Right? So you get what you need, they feel like they’re helping someone who’s starting out early. They have this need as well. And when you can find that perfect win-win, it’s just delicious. So thank you for that because it was one of the… being the first cohort, you really helped us to create a story of what was possible. We didn’t really know that was going to happen. It was just amazing. I guess one of the things to mention to people listening is that the Activators in our network who contribute capital are the ones who vote. So they vote for things they’re really excited about and therefore more likely to help.

VICKI: So you got into BMO, you started to work with, obviously, lots of other people in the community. Can you talk a little bit about the coaching and that sort of guided development support and how that helped with the structure as well?

ILANA: Yeah, I mean, coaching just felt, for better or worse, so inaccessible. When you’re trying to just keep your company afloat, the idea of spending additional money on someone to talk to just was a hard thing for me to be convinced. What I loved was that you knew that… the way that SheEO is designed was you knew that going in. So we got coaching for the year and now I have hired now the coaches because it’s now invaluable to me. So having somebody that’s in my corner is huge. Having someone I’m accountable to. But also there’s so many things I just don’t know and I don’t have experience with. So anything from how do I scale my team? So how do I empower my team to be independent and accountable? To I’m having a really bad day and I need just a pep talk that I’m not completely inept.

VICKI: I know.

ILANA: Or, on the other note, I made a really big mistake, how do I recover from that? There’s just so many things that happen even just within one day, within a startup, that having somebody that you can meet with on a regular basis and continue moving to go forward, it allows you to take a step back and just reflect on where you’re at because so often you can just… it’s so easy to get immediately overwhelmed. Then things start feeling possible, which is one of the worst things. Like your greatest trait is being curious and optimistic and sleep deprivation and an insane amount of operations, logistics, like all the things that especially happen when you’re dealing with a physical product, especially, it’s having that mentor, that coach, was huge.

ILANA: In addition, that was happening at the same time that I was getting introduced to BMO and other clients as well. So just also getting a bit more insights into what our different ways that we can start conversations with companies that we don’t know or conversations that companies are excited about what we’re doing, but how do we start that conversation? So at every stage, the coaching was exceptional and there’s no way that I would have thought to get that if it hadn’t been presented.

VICKI: So I haven’t talked about this with anyone on the podcast yet, but you have such a really funny blog post you did about going to the retreat, going out into the woods with a bunch of women. So one of the things that people probably don’t know is how the capital gets divided up in our network is all the ventures get together, they meet each other for the first time, and they go away for the weekend, meet their coaches, and they divide up the money themselves. Can you talk a little bit about… You were the first group through, so there’s nobody else to tell the story.

ILANA: I am-

VICKI: [inaudible 00:28:00] let people in a little bit on that crazy thing.

ILANA: Yeah, I think we’re close enough now that I can say it without your being… So at that stage in the business, I was both very tired but I also, for better or worse, we being really lucky, I won a number… Like we’d won enough awards that I’d kind of been introduced to companies or organizations that wanted to support entrepreneurs. But I was also being introduced to organizations that, for lack of better words, I called B-roll organizations. So they just want me so they can get B-roll and get smiling, happy people and look how much they’re helping social entrepreneurs. So it created a bit of pessimism for me, which was, “Okay, I’m going to apply for this award and hopefully we’ll get money. And if they can support me or help me with some good advice, that’s great.” I kind of lowered the bar a little bit with my expectations of it.

ILANA: So when I applied for SheEO, I was going in it being like, “Okay, this sounds maybe too good to be true. What’s the catch? I don’t understand.” Then when we found out that we had won, I was both very excited, but one has a very different meaning when the way that it worked was that in that first year, $500000 had been raised and we were one of the five ventures across Canada that won access to the $500000 interest-free loan. But how it was divided was yet to be decided. So all I knew was that I was going into the woods to stay at a cabin with four competitors, for lack of better words, to fight about money was the frame I went into it with. Because I just thought, “Oh, okay, this is like a reality TV show. They’re going to get us to wrestle for this.”

ILANA: So in the lead up to it, I was so guarded because I really didn’t know what I was going into. When I met the ventures, everyone was really nice, but the joke… Maybe, I don’t know if I wrote this in the article, but when I speak about it more in conversation, I’ll say like, “We all arrived and everyone was so nice to each other.” Like they were so nice to each other to a point where I was just like, “What’s going on?” Like, “What’s the strategy? What’s everyone’s…” Everyone was being like, “Oh, this tea is delicious,” or, “This cabinet is gorgeous.” And I was like, “Everyone’s just being like, ‘Please like me, please like me,’ because we’re about to go into a really intense weekend with complete strangers.”

ILANA: Then we were taken through trust exercises where in the lead up to it, we were asked to fill out these surveys that asked about our risk profile. I think it was Lauren and MJ, but Lauren was the one that had it on a poster and she literally showed everyone in the group. They were like, “You’re really aggressive. You back down.” And I was like, “What are you doing?”

VICKI: You’re giving people all of the insight!

ILANA: You’re giving it away!

VICKI: Yeah.

ILANA: So I was just like… really in a bit of a state. And then that was also day Saturday, then we go to know each other, we got to understand each other’s business models all the way until then Sunday started with the negotiation. There was no playbook, like what’s going to happen, so we sat down. Each person went in a circle and said, “Okay, what was the number that you asked for?” There was $500000 on the table. Collectively, our group asked for over $900000. And then I was like, “Okay, is this when we bite?” Instead what happened is we went in a circle and we said, “Okay, what is the minimum? What do you need that will change your business at this point in time?” And the number ended up collectively being under $500000.

ILANA: So then my assumption would be, “Okay, so we’re just going to wrap this up,” but we ended up spending, as you definitely know, hours, because you were waiting in the other cabin, discussing what is the right division. Where my brain just twisted and untwisted and I fully understood why SheEO exists and what the intention of it was, this wasn’t designed for us to fight. This was designed for us to understand that this isn’t just, “Oh, you get $100000. You get $100000. You get…” It’s like how do we get the most out of this incredible gift and how do we make sure that… this doesn’t work if only one venture succeeds. This only works if all five of us succeed. That came out in the most insane way when we went around in the table and everyone lowered their numbers. We had known from the day before that someone in the group backed down very easily and we collectively asked that person, “Are you just backing down?” And encouraged them to ask the real number and she upped her number and we were happy about that. That blew my mind. That was the most insane, crazy moment and I think at that point, I just being… it was so raw.

ILANA: When it wrapped up, I was like, “I just got a yes from four other female founders that I respect and I now love and I’m forever bonded with, that they want me to succeed. They want to get out of my way and they want to support me in every way.” It was the most insanely different experience than I’ve had because there’s always been a catch. There’s always been a, “Okay, we’re going to give you this money, but you have to do this thing,” or, “You have to…” And also, they want me to succeed, but not really. They need me to succeed for as long as that article is posted. This is truly they are happy. Everyone is happy and successful because the rest of us are successful and we have each other’s backs.

ILANA: I don’t know if I told you this, but after that weekend, just the emotional roller coaster, I didn’t even make it fully to my bed. I just dropped my bags and I just cried. Like I just dropped to the floor and I was like, “I am a mess. What just happened?” Yeah, I was… It was just the most insane experience. You took me from being the scaredest pessimist of what kind of insane thing are you going to make me do to just like, “I am on board for this for life. This is insane.” Yeah.

VICKI: Oh, you’ve got me teared up now. Yeah. Because I mean, you really, this whole first cohort… I’m like, “Yeah.” No, but-

ILANA: No, it was-

VICKI: Nobody can see me right now, but I’m crying and you’re crying. It was totally my dream that we can show that you can do things differently. It’s not this scarcity and there’s not enough and you have to fight for whatever you can get. For us it was really 500 women were radically generous and gifted money to you not knowing how you’re going to spend it, who was going to be selected. They just said, “Here. This matters.” And the five of you were really like just… unbelievably perfect first cohort. Right? Just… it worked well.

ILANA: But also I was so amazed at the risk that you and the way that it was designed, the way that SheEO designed the weekend was a risk. You trusted us that we would step into that. I couldn’t imagine what it felt like for you in the other room not knowing how that’s going to be.

VICKI: I just closed my eyes and crossed my fingers. Well, this is what I do though, I trust until I don’t trust.

ILANA: Right.

VICKI: Part of this whole thing is, and you’re a designer so you understand this, it’s you design an experience and you create the conditions that were loving and full of radical generosity. You called it a cabin.

ILANA: [crosstalk 00:35:35].

VICKI: This was a beautiful farm that was… The weekend was gifted to us by Activators in our network. It was their family cabin. One of them’s a chef. She was in the kitchen cooking and making this delicious, nutritious food. You were really well-fed. It was a little uncomfortable because you didn’t know each other and you were sharing rooms and you know. I bared my soul at the beginning and said, “Please, please, please, do the right thing. And I don’t know what the right thing is, but this is our first experiment. This is a global experiment and if we eff this up, we’re done. But no pressure over to you. Have a great weekend.” Yeah. I mean, the transformative experience is like a total dream that that’s possible and then each of these stories starts to create a culture and this is really what it’s all about. So thank you for being an amazing first person and imagine a universe that you are all in on this.

VICKI: So I’d like to talk a little bit about so the emotional thing, which is like the let it go and lose it, which I do daily as an entrepreneur. I wonder if you could share a little bit about how you take care of you? It is so hard to be an entrepreneur.

ILANA: Right?

VICKI: It is a crazy choice.

ILANA: It is. It is crazy and also… I also find that I need to retreat and only talk to other entrepreneurs because you’re not going to necessarily get a lot of sympathy for people. Like I’ve had people be like, “But you chose this.” And I’m like, “Okay, I can’t talk to right now. I’ll talk to you later.” But it is so intense and I would never claim that I’ve, in any way, figured out. Like I’m figuring it out. But my circumstances have been really, really, now the more that I reflect on it, really interesting. Like just the reality of the first few years, it was three years in, I was living below the poverty line. I made it work. I lived with six people in a shared house. I was Airbnb-ing my bedroom two weekends so then my rent was only a few hundred bucks so then I had money for food. And I was like, “That’s it.” I got a free bike from my sister’s friend. I was like, “Really, I need to just make this work.”

ILANA: But the emotional toll on that, in just being under that much stress and pressure, then reflects on the fact that… I remember in the first few years, people were saying, “It’s just about time management.” And I was like, “It’s not time management, it’s guilt management. It’s just how many people am I going to disappoint? How many people am I going to have to cancel on or can I not commit to?” It’s definitely gotten better, but in the early years, the only metaphor I can have and this might be completely inappropriate because I don’t have any children, but I can only compare it to, I used to run a daycare, to having an infant. It’s like I can’t leave this infant alone right now at this stage. It needs to be fed every few hours and I need to be there. Eventually I can take some time off. Eventually there’s a baby sitter. Eventually they’re going off.

ILANA: But in the early stages, the amount of just needing to keep it as close as possible and to be available can take so much out of you that, for me, the biggest change is just being surrounded by a community of entrepreneurs both in working. I love co-living, so I do live with a number of people who happen to be entrepreneurs and artists. But also just really getting in touch with myself and understanding now that I have a bit of breathing room, if I’m just not feeling it today and I’m so stressed out and I can see that I’m bringing the stress into my team, I let myself bail for quote, unquote. I let myself leave. That sometimes is one of the most important things because I, especially as a designer and a business person, you pride yourself on all the different things you can do and how hard you can push.

ILANA: Sometimes that’s necessary and I’m definitely pushing very hard right now with this launch, but at the same time, giving myself the ability to just take a break, go for a walk. I have a lot of friends with condos and they have saunas and that’s one of my favorite things to do ever. So I have a friend who had a condo on Carleton Street and I called it the Schitz Carleton. Then it got out of hand. Like I would bring people to the Schitz Carleton. But I know the things that I need for me to reset. But there’s no way that I would be mentally as okay as I am if I didn’t have just other people that were going through it with me.

VICKI: Yeah, I think this staying alone is so hard. Staying isolated is a real challenge. One of the tools that MJ showed me years ago, which I use all the time is this extend and restore. Out of 1 to 10 on how are you extending yourself this week and how are you restoring? And I remember she gave me this physically, mentally, emotionally, and spiritually.

ILANA: Spiritually, yeah.

VICKI: How do you extend yourself and how do you restore yourself? And the first time, I’m like, “Extend: 10! 10! 10! I extend the crap out of myself every single week. I give everything I’ve got until I’m a puddle on the weekend.” And then she’s like, “Okay, great. And how do you restore yourself.” And I was like, “What? What do you mean? How do I restore myself?” I had the hardest time. I remember sitting there thinking, “I have a bath. I have a bath.” Like literally, that’s all I had. I have a bath. Work out, whatever. Because even my physical, I would blow myself at the gym or something. It was extending. It wasn’t restoring. So I just love to know what entrepreneurs do and I love the fact you said you just bail if you need to. I do the same thing too and it also then models that behavior for your team, which is like I know I can get stuff done in five minutes when I’m on and when I’m not, I can sit there and stare at my computer for three hours. Why would I sit there and stare? I’m an entrepreneur, I created my own rules.

VICKI: I see that a lot with entrepreneurs. We think we have to work 24/7. We have to always be on. But it really is a true sign of maturity, shall I say, if you can sort of step back and do. So Schitz Carleton is a thing, got it. Do you have any practices at your business for your team to remind them to take care of themselves?

ILANA: I think we’re at a really interesting place where I don’t feel like we actually practice as much as we teach right now. So we talk about play, we talk about taking care of yourselves, but I think one of the challenges I actually have is that I think I model a bit too much of the working really, really hard that I do think that… One thing that we’ve been working on this year especially is making sure that everyone is taking their vacation, but also making sure that we make time for play. So Fridays, we’ll, not every Friday, but we were doing this for a while and now that it’s the end of the summer, we’ll try to bring things back, but we have a lot of board games. We have a lot of games that we play and we’ll bring in food or something. Also just having team hangouts.

ILANA: One of the people on my team has this amazing cabin and he invites us out every summer. So we’ll spend the weekend together, which is quite nice. But I think in the day to day, taking breaks, taking steps, we’re in the process right now where we don’t actually have… our space isn’t big enough for us. So the intention of our new space, the next kind of phase that we’re moving into, is going to be designed around the idea that let’s start eating more communally if we can and let’s have more designed moments of serendipity, if that makes any sense?

VICKI: Yeah, totally.

ILANA: Yeah, because it’s so easy to just walk in, sit down, and just start doing work. And you lose so much and there’s so many missed opportunities to develop your culture and be really intentional about it. So those are some of the really key things. I mean, we do have a swing. I installed a swing a few years ago. So that, I call that my mood swing. So we take a lot of swing breaks on it. But intentionally designing breaks. This is the first year where, other than obviously over the holidays, but our Kickstarter ends on October 13th, which happen to be International Day of Failure. But we are taking the entire week off. It’s pretty much mandatory as much as possible. So we can start making plans now for what I’m going to do that week and how I’m going to rest.

ILANA: But I think it’s an ongoing process. I think I’m going to get much better at it when I get better at it for myself, if that makes any sense?

VICKI: Absolutely.

ILANA: Yeah.

VICKI: Well, and I think, I remember I had this incredible mentor when I was getting started and I said, “If you had your life to live over again, what would you do differently?” And one of the things that they said was take off every Friday and integrate/read. And take off a week every quarter to remind myself that I am not indispensable. Literally, the world will go on without me. So we’re doing sort of a version of that in our [inaudible 00:44:48] too. Like we do three weeks off at sort of Christmas time, holiday time, winter holiday, and then breaks during the year. Then people can take their holidays. But yeah, it’s kind of cool to shut down the whole office. Obviously we’re not in crisis management so we can do that. We’re like, “Yeah, okay.” But depending on what kind of company you have, you can create rules, right, to really take care of people and look after their wellbeing.

ILANA: Yeah, I do encourage it. You don’t want people to feel guilty for taking time off. You want them to be excited to share what they did on their vacation.

VICKI: Yeah, we do have this… Yeah, we have this thing right now which is, in the world I mean, in general, there’s unlimited vacation, but nobody takes vacation when you have unlimited vacation because they’re watching to… Everyone’s out-competing each other to be there 24/7 and they’re-

ILANA: Yeah, the one thing I did want to mention. So I have a friend who’s also a female entrepreneur, Erica Pearson, who started Vacation Fund, which is all about that. So it’s employers matching so that they want their employees to take vacation because they’re finding so much, especially in the startup community, people are not taking their vacation days, even if it’s unlimited.

VICKI: Totally.

ILANA: Yeah.

VICKI: Wow. I need to talk to you about getting more space too because we need more space too.

ILANA: Oh really?

VICKI: So maybe we should collaborate.

ILANA: Yes, let’s talk!

VICKI: Anyone else out there who wants more space, we should talk. So we’re just winding down now. Where can we find out about the Failure Toy because we’re going to pop your podcast in right away so it’ll help with your campaign. So where is the info?

ILANA: So if you write out the URL, you can do 21.toys/failure and we have a failing list. So if you put your email in, we’re going to be going live on September 12th and we are giving some pretty substantial discounts on the toys because it is a pre order. So we have 50 available at 65% off and then after that, we’ve got tiers like 35 to… There’s some pretty significant reasons to also get in first. And it’s not just with the toy, but we’re also going to be including in the pledges full day training both in Toronto as well as San Francisco, which we’re really excited about. So we can already start to create that community of educators and facilitators that want to get trained on the Failure Toy in Canada and the U.S. But if you forgot all of that, you can also just google Failure Toy or Empathy Toy. If you google us, you can find us. And then on social media, it’s @21Toys.

VICKI: @21Toys. Okay, cool. Well, thank you very much, Ilana, for everything you’re doing in the world and we are really proud of you and what you’ve built and can’t wait to see it go global, even bigger than it is.

ILANA: We are absolutely cannot be where we are without the community and they have already expressed so much support and excitement with this next toy. It will forever be part of our history and the one thing I would say is what I didn’t expect to come out of this was how much I am now able to support and encourage other female entrepreneurs to get involved both as radically generous Activators, but also as ventures that sort of can really believe that they can think bigger. Thank you.

VICKI: Well, thank you for paying it forward. That’s the greatest impact that I could have. So thank you. Take care.

ILANA: Cheers.

VICKI: Bye. Thanks, hun.

ILANA: Thank you.



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