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In Startup Talk episode 13 I speak with Will GreenBlatt co-founder of OutLoud Speakers School on going to acting school, traveling and teaching in Spain and China, and how an injury turned into starting OutLoud Speakers School and training executives and entrepreneurs on pitching, selling, and public speaking.  Will teaches TechstarsDMZ, and TorontoStarts Startup Launch Accelerator co-horts preparing to pitch to and meet with investors and can be found at Toronto’s Startup Drinks giving advice and feedback.

Direct from the six, world renowned, Canada’s largest city, with Canada’s biggest thinkers, visionaries and hustlers. This is Startup Talk episode 13 featuring the founders, funders, innovators and community leaders who’ve led Canada’s startup ecosystem right here in Toronto. You’ll hear the challenges, the failures, the successes. Toronto’s startup podcast gives you the full story direct from the entrepreneurs and influencers who’ve made a difference. Now, the host of Startup Talk episode 13, the founder of TorontoStarts, the Startup Coach.

Startup Coach: Hey, it’s the Startup Coach here and I’m here today with Will Greenblatt from OutLoud Speakers School. Welcome Will.

Will Greenblatt:  Thank you. Thanks for having me.

Startup Coach:  So we’ve worked together for a little bit now but I’m sure most of our audience don’t know who you are. So first of all why don’t we tell us about Will. Where did you come from? Where did you go to school? What happened to Will?

Will Greenblatt:   Sure. I guess it kind of all started when I fell into child acting when I was seven years old. I started doing film and TV. My family was in the business and I kind of just, yeah, very much walked into it. I had an agent through my father and through my sister and got this kind of big feature film right at the age of seven. That sort of launched me before I even knew what was going on. Then I just kind of worked pretty consistently throughout my childhood and then slowed down a little bit in high school because my mom wanted me to have a sort of normal social life, which I hadn’t up to that point.

Will Greenblatt:   Then I thought, “Okay, well I’ll perfect my craft and go to theater school.” Because I never really had any formal training. I’d just been doing film and TV. So I went to the National Theater School of Canada in Montreal and I just hated it. I could not have hated it more really. It was a really toxic environment. It was 12 of us and we spent every day together, 13 hours a day, 6 days a week, very militant teaching style. There was emotional breakdowns. There were eating disorders. It was really, really bad. The main thing was they didn’t seem to care who we were or to explain anything to us. They just kind of treated us like young children who needed a spanking and who weren’t intelligent enough to understand why we were doing anything.

Will Greenblatt:  I quit acting shortly after that because I was so jaded by that experience. Then I knew I wanted to travel so I got my teaching certificate in Toronto and I went to Spain looking for work. I found some work and spent a year and a half in Spain learning Spanish and teaching English. I discovered I liked teaching. Then some other English teachers, friends of mine from Toronto, came up with this idea. We all got together and thought of starting a school in China, like a school for children. That didn’t quite work out but we ended up starting a ESL, English as a Second Language, and business coaching agency called West Group in Hangzhou China. I spent a year and a half there.

Will Greenblatt: Then I came home and I kind of put everything together in OutLoud Speakers School, which is basically like the English teaching, the acting skills and then everything I’ve also learned as a language learner and a traveler. So to help people how to communicate and speak in public.

Startup Coach:  Wow. So what was the difference, just because I’m here, between Spain and China and teaching?

Will Greenblatt:  There were some notable differences. Like in Spain it was an interesting mindset that a lot of the students had, which was why do we need to learn English? This doesn’t matter, Spanish is the best language ever and this is stupid and I don’t need to do this. It was kind of interesting, there was a lot of struggle to get people to even care about what I was teaching them. Then in China, it couldn’t have been further from the truth. Most people really understood the need for English or at least they felt they needed it. There is a stereotype about Chinese kids but it’s true that they’re very well behaved in class and they’re very studious. I have to say as a teacher, that’s really nice.

Will Greenblatt:  In Spain they were not as disciplined. They were not as well behaved. They were not as studious. So I felt like I sort of got thrown into the deep end in Spain, but it was good. I feel like I built up a lot of resistance to how crazy students can be.

Startup Coach:  So you went to acting school, you’d done your acting bit, you found your teaching bug traveling abroad, so how did that lead to OutLoud Speakers School?

Will Greenblatt:  I came home from China, it’s a whole other story, but I was really badly injured. I had a herniated disc and I had to come home to take advantage of the Canadian healthcare system that we have. I was sort of injured and unable to work for the better part of a year because I was bedridden. I didn’t know what I was going to do. I was like, “Should I go somewhere else or should I go back to China?” I wanted to continue with the company but then it became clear that I couldn’t. So my acting mentor, who is my co-founder Nicky Guadagni, she invited me to this course that she was doing at UFT. She said, “I’m working with these science students and I’m helping them with their research pitches.” She was like, “Why don’t you come check it out maybe you can sub for me?”

Will Greenblatt:  I went and I saw what she was doing with them, the way she was getting them to enunciate and use their face and their hands and their body language and look for the different ways of breaking down their story and all that. I went, “That’s what I do in my English classes and my conversation classes.” It was amazing watching her to this because I was like, “That’s exactly what I do.” All the teaching methods that I had learned that I thought were my own, we started to realize after talking, that it just kind of came from acting. Acting common sense and acting classic theater training. All these principles are pretty similar. Then we found out that we also had similar theories on education and how to help people and how to reach people.

Will Greenblatt:  So I just kind of said, “I think there’s a business here.” So we launched in July, 2017 and we’ve been working ever since.

Startup Coach:  That’s fantastic. I understand you work a lot of executives and how do they find out about you and what are they looking for when an executive approaches you and says, “I want your help?”

Will Greenblatt:  I missed the last part of your question.

Startup Coach:   Sorry.

Will Greenblatt:  No, that’s all right. When an executive approaches you and says?

Startup Coach: And says, “I want your help.” What kind of benefits are you…

Will Greenblatt:  So usually, very often it comes when people are either being told by their colleagues that they’re having trouble with their communication or they themselves are just petrified at public speaking. So it usually comes from a pretty, it can come from one of two places. One is like a deep fear and wanting to really work so that they can stop feeling so scared. Then the other is like they come a little more resentful because other people have given them the feedback.

Will Greenblatt:  But it’s always the same. It’s that they… When most of us get into a public speaking situation, what happens is our primal instinct tells us that, “Oh this is really important with everybody looking at you, it’s so important that you impress people and you make people trust you and you prove your worth to your tribe.” Because our evolutionary psychology tells us that our tribe could kick us out if we don’t make an impact. We don’t show our worth. So that’s a huge stake situation. But of course, it’s not that big a deal in modern day times. We don’t understand those mechanisms though. Most of us don’t understand what’s going on in our brains, why we get so nervous, why we can’t remember anything or we don’t understand that the way that we present ourselves, is not how we feel on the inside.

Will Greenblatt: So somebody who’s kind of boring to watch and flat and is not able to make their words come to life, they just think they’re speaking at a totally fine level of energy. They’re actually going, “So everyone hears my presentation.” But nobody can really say it to them without offending them. What we do is just give them permission to be bigger and show them what they’re doing, what it’s communicating and getting them interested in that. Then all of a sudden, they start coming to life and they start noticing more deals that they’re closing and they do better in their pitches. Some of our clients have won pitch competitions. We work with Techstars and the [inaudible 00:08:35] last year. They had their best pitch day they’ve ever had in their history.

Will Greenblatt:  So it really is just a matter of looking at your habits and your speaking style and figuring out how can you make your story sing and come to life. That’s what we help them with.

Startup Coach:  You jumped the gun on me here which is great. I was going to say, how does this relate to entrepreneurs? You mentioned you work with Techstars, I know you’re working with DMZ, if not now, soon. I know you’re working with several other investing companies and you work with a lot of people in our community. You work with the FFCON, Fintech and Funding Conference pitch finalists and we’re going to be working with the pitching companies in Toronto for the Fundica Roadshow. How does what you do translate to pitching and talking to investors because it’s not the traditional pitching coach style that people think of?

Will Greenblatt:  The way that we think about it, one of our core principles, two core principles, is knowing your audience and understanding your intention and building your intention and staying true to it. For our entrepreneurs when they’re pitching to investors or when they’re pitching to impossible clients, they have to really think about, “Okay, what do I want from this particular situation? How do I want to affect the person that I’m talking to? What parts of the story will be interesting to the person I’m talking to?” That takes a lot of active awareness. You have to really think about that.

Will Greenblatt:  We suffer from what Steven Pinker calls the curse of knowledge which is that when you know something, it’s really hard to put yourself in the shoes of people who don’t know it. Which is basically everybody else who’s not part of your company. So when you’re pitching something, you have to think from their perspective. Okay, what’s interesting to them? What would be interesting to them? What is irrelevant to the situation that I’m in right now? What is extra information? What kind of fact can I trim from my pitch? How could I use my face and my voice and my body to really impact them in a way that’s going to reach, you know you talk about the crocodile brain, in a way that’s going to reach through their crocodile brain and get up to the neocortex, which is where all the high level decisions are made.

Will Greenblatt:  Getting them to really think about who their audience is and what their intention is, is really important for entrepreneurs and as we’ve noticed, it really helps them when they start to think in these terms.

Startup Coach:  It’s amazing when they actually start to think of the terms. Entrepreneurs are always too close to their product to actually make a really good pitch. It takes a while to get that out of them. That’s interesting. I’ve seen you in action. I’ve seen people give you rave reviews, some of my past students and whatnot. From saying you’re completely different than other pitch coaches and they’ve seen it all before and you kind of give them advice and take them to the next level. How do people translate? One thing is when you’re pitching on a stage to whoever. But when you are meeting with investors, how do you, what’s your tip for entrepreneurs to communicate that confidence and that passion? What advice are you giving them when you’re not there when they’re in that room sitting with those investors?


The golden rule of speaking, You have to make them understand and you have to make them care.

Will Greenblatt – OutLoud Speakers School

Will Greenblatt:  I have what I call the golden rule of speaking, which is something that you can apply to every conversation that you want to have an impact with. That is that you really only have two jobs. You have to make them understand and you have to make them care. That’s the golden rule of speaking.

Will Greenblatt:  When you’re on stage, there’s a lot of craft to consider about the way that you are standing, your body language and the range of your voice, that you have enough projection. There’s things that we work with which we call the speech settings, like volume, pitch, pace, etc. But when you’re one-on-one, a lot of the performance and the art has to fall away so that people feel like you’re really speaking to them in that moment. The number one tip is just the golden rule. Make them understand, make sure they’re following you. A lot of that comes from mindfulness and being present.


The number one tip is just the golden rule. Make them understand, make sure they’re following you. A lot of that comes from mindfulness and being present.

Will Greenblatt – Outloud Speakers School

Will Greenblatt: I tell every single one of my clients, if you don’t know anything about mindfulness, start researching it and start practicing it. There’s three minute things on YouTube, Guided Mindfulness Meditations. There’s a great app called Ten Percent Happier, from Dan Harris, who helps it’s called Meditation for Fidgety Skeptics, so people who don’t think that they will take to it. It’s just a really important thing to remind yourself where you are, what you’re doing, who you’re talking to and what you’re trying to communicate. Because we get wrapped up in our own heads, our anxious thoughts trying to throw us off kilter.

Will Greenblatt:  We’re talking to someone and we go, “Oh shit. I hope they like me.” Or, “I hope they think I’m cool. Maybe they’re going to think I’m a fraud.” Then we lose track of actually what we’re saying. So bringing yourself back to, “Okay. What is my story here? How can I make sure that they’re with me?” So that’s checking in with them, making eye contact, looking at their face and saying, “Does it seem like they’re understanding me?” Making sure I’m packaging it in a way that is as tight as possible and is also relatable, emotionally relatable. So things that cut to people like family and health and wealth and security and happiness, things that affect everyone and that make us think about the emotional side of life are very important to highlight as well.

Startup Coach: Those are all great tips. From your point of view, what are the biggest areas of improvement for most entrepreneurs?


Give yourself permission to get excited and be big and passionate about your idea.

Will Greenblatt – OutLoud Speakers School

Will Greenblatt: I’d say the biggest area of improvement is, and again, this comes back to giving yourself permission, which is usually what I give to clients. Give yourself permission to get excited and be big and passionate about your idea. I think a lot of us have this assumption that when we’re in a business situation, we have to be credible and serious and authoritative. So we actually just sound boring because the volume goes down, the pitch goes down, we kind of go down here into the low voice and we want to sound mature and serious. But really it just loses any kind of flair and any kind of passion.

Will Greenblatt:  So if you notice now with my voice, my pitch is kind of going up, my pace is pretty quick, but I’m still speaking clearly so that every word can be understood. Hopefully you can hear in my voice that I care about what I’m talking about. Audience members, people listening to you, are pretty pliable. They will take on the energy that you’re giving off. If you seem like you don’t care, it’s very unlikely that they will care. If you seem passionate and enthusiastic and they can hear that in your voice and they can see it on your face and in your hands and in your body language, they will be way more likely to get excited about it themselves.

Will Greenblatt: Too often I see people, really low energy, low pitch, kind of low in the chest, which doesn’t really communicate much excitement. Higher pitch usually communicates excitement and also there’s usually a deadness in the face. There’s no smile and there’s no eyebrow engagement. If you just smile and raise your eyebrows, all of a sudden the face comes to life. The person comes to life. People go, “I don’t necessarily know what they’re saying yet, but I want to talk to that person and I want to work with that person.” You give off this vibe of approachability and passion and warmth and people respond to that.

Startup Coach:  We go back to Dan Harris and mindfulness. You’re getting the entrepreneur in a state of flow, as it were, that they’re in the moment. They’re not thinking about what to say and they’re just doing that. At the same time, intonation, showing their passion on the face, really putting their emotion into it, so that all the things that being in the moment are part of. When we talk about entrepreneurs, I’m really happier when people to what they love and they’re passionate about rather than someone who just comes with an idea.

Startup Coach: I just thought of this thing, “Oh no, I want to do this because of this story in my life or because of this impact or because I really believe these things.” When you can ignite that passion during a pitch and stop them from worrying about stuff, then that really comes across and it really sells well and is authentic. Part of what you say is you like to ignite the passion or communicate the passion in people. How do you get people to do that?

Will Greenblatt:  I was just going to jump in before but that’s the perfect question. For me it usually comes from, because most people aren’t actors. An actor can kind of fake passion but in my opinion, any actor worth their name, is not going to try to fake stuff. They’re going to try to use their imagination to get into their character’s mindset and to get into their character’s emotional being and try to say, “Okay, what motivates this person?” You can kind of use that on yourself. These ways of thinking about your character but you just think about yourself.

Will Greenblatt:  One big problem is you started this company because you had a passion for it. But with all of the pitching, you’re saying the same things over and over again, when we say the same phrases they start to lose meaning, even to us. They just become buzz words and taglines and we just kind of rattle them off. For me it’s like, “Hi, I’m Will from OutLoud Speakers School. We’re a company of actors teaching public speaking and communications.” You just kind of rattle it off because you say it so many times.

Will Greenblatt:  But reminding yourself, why did you get into entrepreneurship in the first place? What freedom has this given your life that is so amazing, that is so much better than that nine to five that you fucking hated and left? What are the amazing benefits that you have in your life because of this? Now this particular business. Why did you start it? What about it makes you excited that you can talk about it for hours, that you’re going to keep working on it like 14 hours a day and do all the work that it needs to grow it and make it into a self-sustaining business?

Will Greenblatt:  A lot of that just comes from reminding yourself. Just taking a second and doing a meditation of sorts and going, “Okay. What does this company mean to me? What are all the hours of work that I’ve put in? What are some of the amazing ups and downs that I’ve gone through?” I call it imaging. It’s where you sit, you close your eyes and you think about images and stories and sights and sounds and smells like where was I when my co-founders and I came up with the name and the logo? Were we sitting around at a coffee shop or were we in someone’s living room? How exciting was that. Reminding yourself of specific moments with details is really good for infusing emotion into what you talk about.

Will Greenblatt:  It’s a constant practice, I say. You have to remind yourself all the time. This is exciting, this is exciting. They’ve never heard it before. It’s the millionth time I’m saying it but it’s the first time they’re hearing it. That’s really important. Try to put yourself in that excited passionate mode of the first time you thought about this or the early days of your project.

Startup Coach:  That’s very good advice. As you work with a lot of entrepreneurs and you’re staying up on these things, is there any books you’d recommend for people who read?

Will Greenblatt:  Yeah for sure. The Storytelling Animal by Jonathan Gottschall is amazing. It’s all about storytelling as the title suggests but it’s about the human brain evolutionary psychology which, as you can probably tell, is a big influencer on the way that I approach this work. It talks about how human beings form this desire for story and where it came from in the way that we used to communicate in tribes. How we are affected by story and emotion and how memory works and how imagination works. It’s really, really good for understanding all of these things.

Will Greenblatt: Also, Pitch Anything is great. I think you reference that. I think there’s a lot of really strong, practical ideas. It talks about the brain and what goes on at the level of the brain. Also, I just say anything you can do… In the Storytelling Animal he mentions Keith Oatley, who wrote a book in which he compares reading fiction to a flight simulator for human life. Which means that the more fiction you read, the more you start to understand what goes on between people. You actually can improve your social skills by reading fiction because you’re kind of putting yourself in the character’s mind and going, “What does saying something like this, how does that affect somebody else? What did they do because of that? How did their words affect?” You start to really get a good sense of that.

Will Greenblatt:  Keith Oatley, his book is called Our Minds, Our selves. That’s another great one. Then just any fiction. Right now I’m reading, or I just finished reading, The Corrections by Jonathan Franzen. It’s just all about people and emotions and stuff. It’s very character driven and not so much plot driven. So when you read stuff like that and you think about the characters, you just become a more empathetic human being and you find out that you’re better able to reach people and figure out what interests them. You can create and deliver your pitch a lot more effectively.

Startup Coach:  All interesting reads. Some of them I haven’t read, so I’ll have to put them on my list. One I’ll add, just because I’m reading it now, is Influence The Psychology of Persuasion. I’ll put the link in the show notes because it’s really talking about the minds. How our mind works and some of the mental biases we have and how to take advantage of them or avoid them, depending on where you are. So very interesting.

Will Greenblatt: Any book like that, that is about psychology or behavioral economics, I should also say Thinking, Fast and Slow by Daniel Kahneman. Every, every entrepreneur should read that. Any book that is about bias and psychology and the way the brain works, is just gold for communication skills.

Startup Coach:  Fantastic. Is there any blogs or other resources you would suggest people check out?

Will Greenblatt:  Yeah. I would say listen to podcasts. Two that I really like are the Joe Rogan Experience and Russell Brand, Under the Skin, because again, they just kind of talk. They have these two hour, three hour long form podcasts. You just listen to how people get into ideas and unravel them and sometimes they argue and sometimes they agree. You see where things start to break down. Both of those podcasts are really good for that. They also just expose you to some really interesting thinkers who talk a lot about psychology and human achievement. They also very often have some great entrepreneurs on there. Tim Ferriss’s podcast. I think most of your listeners will probably already be aware of it. Tim Ferriss’s podcast is great for entrepreneurs.

Will Greenblatt:  In terms of blogs, I prefer listening to podcasts, watching YouTube videos and reading books. I prefer that to blogs. But the best blogger I think is Mark Manson. If you go to markmanson.net he’s a fantastic blogger. Talks a lot about psychology in achievement and desires. Yeah, Mark Manson’s great.

Startup Coach:   Yeah, I’ll have to take a look at Mark Manson. Practice makes perfect when it comes to pitching. Is there any places, resources you suggest people go to practice?

Will Greenblatt:  There are all these pitch competitions that you can apply to. If you can find a local Toastmasters, it’s a great starting point, just to start to get up in front of people and get some feedback. It’s a very welcoming opportunity. There’s also York Angels where you can go and pitch. There’s also PitchIt, which I think is in North York as well.

Startup Coach:  There’s a regular PitchItTO one that’s usually done at City Hall as well.

Will Greenblatt:  So if you Google PitchIt, you should be able to find places that do that.

Startup Coach:    PitchitTO.

Will Greenblatt:    Yeah, PitchItTO, that’s right. Then there’s also your startup drinks that you have, where you give everyone the opportunity to get up and give a one minute pitch. People really learn a lot from that. Just that sort of speed, the rapid fire way that they get up and have to capture their ideas into one minute. Then they also get to watch everybody else go. Looking for things like that if they go on Meetup, they should find those. Also, we have, OutLoud Speakers School, is running monthly pitch workshops where they’ll actually get taught how to pitch and then get a chance to pitch and be coached as well at the end of the workshop.

Startup Coach:  Where would people go to find more about OutLoud Speakers School and these workshops?

Will Greenblatt:  We’ll be posting about these workshops on our social media. All our social media is @outloudschool. So that’s LinkedIn, Facebook, Twitter and Instagram. Also, you can follow me on Instagram and Facebook and LinkedIn @willgreenblatt. So if they type in Will Greenblatt into all of those, they should find me. I often post about this stuff as well. Our website is outloudnow.com.

Startup Coach:  You also have a podcast. Where should people find that? What’s the name of it and how do they subscribe?

Will Greenblatt:  Yes. You are one of our best guests on that podcast. It’s called Thinking OutLoud. It’s on iTunes, Spotify and Anchor. So if they search for Thinking OutLoud, Will Greenblatt, then they will be able to find it on Spotify, iTunes and Anchor.

Startup Coach: Fantastic. Any last words for our entrepreneurial community?


don’t be afraid to show your passion and remind yourself of your passion. That’s the big one. Give yourself permission to be enthusiastic, be energetic. That’s what makes an impact on people

Will Greenblatt – OutLoud Speakers School

Will Greenblatt:  I would just say don’t be afraid to show your passion and remind yourself of your passion. That’s the big one. Give yourself permission to be enthusiastic, be energetic. That’s what makes an impact on people.

Startup Coach:  I perfectly agree. Thank you for being on Startup Talk, Will.

Will Greenblatt:  Thanks for having me, Craig. It was fun.

Startup Coach:  This has been Startup Talk episode 13. I’m the Startup Coach, we’ll see you next time.

This has been Startup Talk episode 13, Toronto’s startup podcast. For more exclusive content, the episode vault and to be part of TorontoStarts community, visit torontostarts.com. Get your name on the newsletter mailing list and check out our upcoming events. For more episodes, subscribe now. Please recognize the time and work behind the scenes put into connecting you with the biggest visionaries, entrepreneurs and innovators in Toronto by leaving a five star review. Join us for more next episode from Toronto’s most active entrepreneur and startup community on Startup Talk.

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