Many entrepreneurs dream of taking the stage, sharing their message with audiences as a public speaker. And a book not only acts as a brilliant companion to this strategy for back of the room book sales, but also acts as a foot in the door to unlock such speaking opportunities that might not otherwise be available.
In this episode of The Entrepreneur to Author Podcast, your host Scott MacMillan speaks with Will Greenblatt, co-founder of OutLoud Speakers School and author of Transform Your Speaking Skills: How to Gain Confidence, Captivate Audiences and Advance Your Career about his entrepreneur to author journey and how he teaches business people how to communicate powerfully and effectively in every speaking situation.
Buy Will's book Transform Your Speaking Skills: https://www.amazon.ca/dp/1989737803/
Guest BioWill Greenblatt has been acting professionally since he was seven years old, initially starring in The Homecoming with Academy Award Winner Anne Bancroft. He graduated from the National Theatre School of Canada in 2010, but the toxic environment of the program left him jaded, so he quit acting. He moved to Spain where he discovered his love for teaching English, and then dived into the world of entrepreneurship, co-founding the Executive Coaching company Westgroup Ltd. in Hangzhou China. After exiting, he co-founded OutLoud Speakers School, an agency of actors teaching public speaking & communication skills to entrepreneurs and executives. He has repeatedly spoken and coached at Google, Wayfair, TechStars, Boston Dynamics, and Ericsson, as well as providing coaching to over 4500 individuals virtually worldwide. OutLoud’s clients have won numerous pitch competitions and raised over $200 million USD in investment. When he’s not running OutLoud, he is also a performing and recording musician, with his album Borden Street available on all streaming platforms. Will speaks 4 international languages, including Mandarin Chinese and is currently learning his
5th, Urdu/Hindi, to speak with his wife’s family.
CONNECT WITH WILL
Website – http://www.outloudnow.com
Instagram – @willgreenblatt
Twitter – @outloudschoolTikTok – @williamgreenblatt
CONNECT WITH SCOTThttps://entrepreneurtoauthor.com
Scott on LinkedIn (@scottmacmillan): https://www.linkedin.com/in/scottmacmillan/
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Scott on Medium (@scottamacmillan): https://scottamacmillan.medium.com
Please note: The transcript is produced by a third-party company from an audio recording and may include transcription errors.
This is SSN.
(Story Studio Network)
You're listening to the Entrepreneur to Author podcast.
Welcome to the Entrepreneur to Author podcast, the podcast that brings you practical strategies for building authority and growing your business. And now, here's your host, Scott McMillan.
Will Greenblatt is the co-founder of OutLoud Speaker School and author of Transform Your Speaking Skills, How To Gain Confidence, Captivate Audiences, and Advance Your Career. He graduated from the National Theater School of Canada and has been acting professionally since he was seven years old. Will has repeatedly spoken and coached at the likes of Google, Wayfair, Techstars, Boston Dynamics, and Ericsson, as well as providing coaching to over 4,500 individuals worldwide. What's more? He speaks four international languages and he's currently learning his fifth. Will, it's so great to have you on the podcast. Thanks so much for being here.
Thanks for having me, Scott. It's really nice. I haven't done one of these in a while, so it'll be really fun I think.
Wonderful. So to start, I'd love if you could share a little bit about your journey, your entrepreneurial journey for our audience so they can get to know you a little bit better.
For sure. So as you mentioned in the intro, I started as an actor since I was seven years old. So I fell into the business through my parents who were both... My dad was an actor, my mom was a writer and director, and my dad had an agent. So through that sort of nepotism, I got the same agent that he had and I ended up booking the first film that I auditioned for at seven years old, which was a complete fluke, I happened to be perfectly right for this part and it was a big American-Canadian co-production and it kind of launched this child acting career that could have gone a bunch of ways, but I think very wisely, my mom refused kind of the calls to go to LA and try to do that whole thing. She, with me and my decision-making as well, we decided to kind of try to live a normal life as much as possible while having this child acting career.
So I would do these TV shows and films, but I'd also go to school and just live a sort of normal life as much as possible. But I loved it. I loved being on film sets and I loved doing TV shows, learning scripts and playing these different characters. Even at a young age, I just really enjoyed it. I loved learning my lines and seeing how well I could memorize them and stuff. And so when I graduated high school, I had in my mind this image of, well, I've figured out my career. There's no more soul searching to do because I know it already. I've been doing it since I was seven. And then I decided to go to theater school to get that kind of conservatory style, rigorous education.
I was like, well, I've been doing it but I've never had any training, so why don't I go get some training? And then once I got to theater school, it just was not the experience I was expecting. It was a lot more, let's say, it was emotionally abusive, maybe without meaning... Without the teachers intending it to be that way. It was really hard on the kids who were in the program. There was a lot of mental health issues, kids dropping out with nervous breakdowns and eating disorders and all sorts of stuff. It was just a very unhealthy environment in general. And I really suffered through that time as well mentally, I was not having a good time and so when I graduated I just needed some kind of change because of how awful this kind of experience was. And I sort of started to realize, I don't know if I want to be an actor.
So I ended up running away to Europe and I started teaching English in Spain. I realized, oh wow, teaching's really fun and you can use some of these skills that I've learned as an actor. I can use them to keep the attention of a class and to help people understand concepts with just the power of my voice and the words that I'm choosing to use and how to explain things and my hands and body language and all that. And then from there it was sort of a natural progression to start a company where we taught those skills to people. So my first company was in China where I was doing that sort of mixing English education and business coaching. And then the next venture was back in Canada, which is the current one OutLoud Speaker School.
And through that I kind of learned what it meant to be an entrepreneur and to be the head of a business and figure out all the pieces that need to be worked on in order to build a business. And then also how to take what I know as an actor and package that into services and product-based, services-based products, that is to say, to people who need it. And so right now we work with a lot of entrepreneurs and also enterprises to help people with their public speaking skills. So it's a very long answer. I hope it's not too long winded, but that's how I got from there to here and that's the basis of the work we do now.
Yeah, that's wonderful. That's exactly what I was hoping to get a flavor of because what I find so interesting about your path is that, you started in what for many, is a very creative, performance driven craft, let's call it. And you loved that aspect of it. And what I find so interesting is how you've carved out the parts of it that you enjoyed so much and layered that into your business. So that's really fascinating. I think a lot of people can learn a lot from that. And so this past year you wrote and published your book, Transform Your Speaking Skills. Could you share a little bit about the book? And who's it written for and what's your goal for your reader?
Yeah, I really, really loved trying to figure out that exact question and it's still, I think a work in progress as I'm sure it is for a lot of entrepreneurs, especially at this stage of their career, if they're thinking about writing their first book or trying to get their thoughts down in a way that would merit a book and then thinking about what that target audience is. But this book was really for entrepreneurs and professionals looking to advance their careers, that's in the subtitle, Advance Your Career. That's really the goal that I want the reader to come away with, is the confidence that you gain from learning your public speaking skills, the relationships that you're able to cultivate once you do get a sense of how people like to be spoken to and how stories get told in a way that people remember them and want to act on the information being shared. That's the kind of thing I'm hoping to convey.
And so the point of the book is to give a sense of the kind of stuff that we do in our public speaking training courses, but in a lot more of an intimate way by mixing my story in there as well. So a lot of the stuff I sort of covered in the answer when you asked about my story is in the book and then a lot more stuff there too because I don't believe you can separate an individual from the entrepreneur. That person, the skills that they have, the way that they view the world, the kind of a boss they'll be, the kind of a partner they'll be, the kind of a practitioner they will be, is informed by their life experience. And for you to share that with your audience, really who you are and the events that made you that way and the way you see the world, the more you can share that in a cohesive and compelling way, it's like a gift that you give to the audience that has a great ripple effect, which is that they love you and they trust you and they want to know you and they want to work with you.
Sharing your personal story opens up a vulnerability in the minds or the brains or the listener or the reader. And so this book, I thought it was really, really important to try to practice what I preach. I always tell people to share their personal stories, so I share a lot of personal stories. It's probably overshare for most people, but to me, it's the relevant points in my life, the traumas, the hard times, the weird little moments where I had a realization, the books that I read, the relationships I had, the ones that went well, the ones that didn't go well and all of that brought me to where I was.
So trying to find the most relevant narrative and the relevant through line that brought me from there to here and sharing that with the audience and then why those experiences led me to do the work I do now and what those practical techniques are. So I learned this thing in Spain while I was living there and it taught me this exercise that I taught my students there that still works to this day. So I would tell the story of that moment in Spain and then I would give the exercise and the practical explanation of how to do it. So I hope that by giving the story, it provides some context to make the person want to do the exercise and also remember it and remember the concept because it's connected to a story.
Yeah, absolutely. How did you find the writing process? You, as many of us entrepreneurs, have methodologies and approaches and intellectual property that we bring to bear for our clients in the work that we do with them, but it's not always easy to translate those into the written word in a long form format, like a book. How did you find that experience of capturing all of that intellectual property and distilling it down into a manuscript?
Well, first of all, it's really hard and you should be aware of that going in, that it's not going to be as easy as, well, I know all these things and all I got to do is get them down on paper because it's great to get your thoughts down on paper, but of course the editing and the condensing and distillation of those thoughts into something that the reader who is not in your head and has not had your life experience can gain something from, that is really difficult. And I found it difficult but so rewarding. And so it had just also so many benefits for working with my clients as I would write during the day then I'd have a client in the afternoon or a sales conversation in the afternoon and I was so much more clear because I had spent the day thinking, how do I say this part of my work in a really concise, clear way?
And then you come up with things also that you start using in your sales conversations or with your clients in order to help them understand the concepts you do the work as a writer and then you become a better speaker because you've done that foundational work to come up with the best way to say something. So I found it very rewarding in that sense. All that hard work, trying to find time to write for an hour every day. I put it in my calendar, that was one of the things I had to do, said every day from 4:00 PM to 5:00 PM I have to spend an hour writing because otherwise I won't get it done if I don't write every day. And then of course sometimes, you write for more than an hour because you hit the flow state, which is so also rewarding and sometimes you don't and it feels like grinding teeth and you're a marathon runner, right?
That's right, yeah. As are you?
Yes. So I see that in your social media and I feel like it's very similar to that sort of process where it's really difficult and then you reach the finish line, which for the book would be the launch date or whatever, and then the flood of positive emotion that you get from the accomplishment makes all the difficult moments worth it. And then you realize that of course the difficult moments were part of the reward. And that lesson is really, really cool from both I think marathon running and also the book writing is, you don't want to just avoid something because it's hard. In fact, you probably want to lean into that. And so that would be my advice for anyone who is on the fence is, it's hard and well worth it and definitely something to dive into.
Yeah, it's such a great analogy and I've had Nick Muxlow on the podcast, one of our authors who is not just a marathon runner but ultramarathon runner and running coach and he made that same analogy, right? It's a lot of work and a lot of discipline to get to even just a race day. All of the work has to go in before race day or in this case before the launch of the book. So that it's a very apt analogy. And you were writing at the same time that your family was expecting a new baby. So a lot of additional tensions and considerations there. As you submitted your manuscript and you were in the publishing phase where the editing happens and the book design and distribution and publication, what was perhaps surprising about that part of the journey? Whether it was surprising in a positive way or a negative way, what was frustrating? What was maybe exciting?
Well, certainly trying to do a project like this, while life feels overwhelming, is just... I mean, that's the nature of being an entrepreneur, so there's no way to avoid that sort of thing. And I think learning to lean into never feeling you have enough time, never feeling like stuff is as good as it could be before you have to get it out there. But that was one lesson that I learned that I've also learned from making music is learning to be okay with imperfection and letting something get out there even if you feel like if you worked on it for a couple more weeks, it could be better, but just going, it's as good as it needs to be. And if I don't get this out now, it won't happen for another two weeks and then that'll push back the next phase of the project by two weeks.
And then of course once you learn to let go of the need to make it perfect, often that's kind of better because you can definitely overwork stuff. And so my first album that I made, I over edited it, it was overproduced. I spent so much time in the studio with the sound engineer, fixing every little level and trying to fix every part, adding new instruments, taking out instruments and doing multiple takes and never being satisfied. And then I made another record where I just trusted the editor I was working with and I just said, yep, good enough for me. There was moments where I had to push back or moments where I said it's not quite there yet, but in general, learning to let go. And with the book publishing, it was similar with the cover or with the typeface or the font or whatever, and going, you know what?
This is as good as it needs to be and let's just get it out there and then the next one can be that much better and then the next one can be that much better. So taking the longer view. So I was a lot less perfectionist about the publishing aspects of it than I thought I would be. And I'm so glad I was. And now I love it. I love the way the book looks, I'm really happy with it. If I ever see anything where I wish I had maybe worked on it a bit more, I remind myself, nobody's going to know that, nobody's going to care, nobody's going to obsess about it as much as I am. So I was pleasantly surprised by my ability to let go. And I found it a great lesson for just entrepreneurship and creativity. Creative projects in general.
Yeah, beautiful. How are you using the book now? Obviously, as entrepreneurs we write our books not just as a creative outlet, there's a business aspect to it. What were your goals for your book from a business perspective, and how are you incorporating it into your business?
So I think I went into it not expecting to have a big financial return on my investment, both my time and my money investment. I think a lot of entrepreneurs who want to write their first book before they necessarily amass a big following in any way is that you're not going to launch the book and make up the cost of what it takes to publish it. Whether that's a time cost from you writing it or a publishing fee or whatever that is. You're not going to make that up on launch day because you may not have this email subscriber list of 50,000 people or a huge social media following or whatever that is. So I didn't think from the beginning that I would make a ton of money in sales, certainly at first, what I really wanted was a couple things. One was basically a training manual for my coaches.
We hire coaches to run this work. That's how I plan on scaling my businesses. One of the things that really important for me is that I want to create a business, not just a single person or two people. I have a co-founder as well. We want to be able to train other coaches to do the work that we do so we can have more clients and we can spread the work more far and wide. And so a training manual for the coaches, one. The second thing was a way for anyone who might want to work with us to have an entry point into the work because it's so hard to describe what you do sometimes. And this way you can just send somebody a PDF or mail somebody a copy of the book. They look at it, first of all, it looks professional, it's professionally done and laid out.
There's a lot of credibility there, a really nice website. And then if they actually delve into the thing which you hope they do, then it's just like the clouds start to part a little bit and they're like, oh, okay, I get what this person is doing, I thought I knew what it was, but this is something different. And oh, that's a funny story and oh, I know a bit more about this person. And they build a relationship with you. It's a one-sided relationship, but it's still building that. And in general, one of my messages is that human beings work with people who they like and people like who they know. The more about somebody, the harder it is to dislike them. And so the converse is true. Usually the more about a person, the more you like them, the more empathy you have with them and stuff.
So it's a great way, especially if you've written it from that honest, transparent, authentic perspective where you've shared a bit of your story, you are building that trust with any potential customers. So right now I'm using it as a really, really fancy detailed business card and sales tool. And then also I'm hoping to create a bit of a speaking circuit at some point with the book as an added incentive for people to join, people to bring me in to speak. And then it's either something I can share at the beginning where they can get excited for the work or something I share at the end as a freebie and just trying to figure out the best way to do that, business wise. But I always want to try to give it away as much as possible.
That makes a lot of sense that that's my philosophy too. And what I love about your response there was that, you've thought about what your goals are with it because the way that you utilize the book is going to be very different depending on what you're trying to accomplish with it. And it sounds like we have a similar philosophy about the purpose of the book and the value of the book and how to deploy that to best effect. For those who have considered writing a book but haven't done it yet, what advice would you give them?
I would say don't worry about whether or not you can write, just forget about that right away. That's not your job, essentially. That sounds weird, but it really isn't your job to decide whether you are good enough at writing to write a book or not. What is your job is to figure out what in your life and in your work is interesting and to whom, and then trying to get that down in whatever way you can. And so tons of people use ghostwriters. As far as I can tell, there's no shame in that. I love writing, so I wanted to do it myself, but I've always loved writing, it's something I really enjoy and it doesn't feel too much like an awful chore. For some people it might. And for some people they really just don't know how to put words together that well.
That's fine. I mean, I believe you should try to learn and it's a great way to try to learn, but just think about the story rather than the ability to get it down on paper and then get it down on paper in whatever way you can. And again, don't second guess the quality of the product that you're putting out there. Don't second guess, "Oh, this is stupid, nobody's going to care." Just get it down. And worst comes to absolute worst, you spend a bunch of time, you spend a bunch of money, nobody cares and nobody buys it and it never does anything for you. But you will have done such a valuable exercise in condensing, crystallizing, and distilling your thoughts and looking at your own life story and picking out those key moments, that I think it's so worth it because as I said before, you'll use that in your work, you'll use it anytime you talk to anybody that you want to have any business relationship with.
What do I want them to know about me that is compelling and that sparks interest, sparks conversation? That's so important for any kind of sales, any kind of hiring practices, any kind of leadership that you're doing. How do you connect with people, and how do you ask them the interesting things about themselves that you get better at when you write your book? Yeah, I would just say, just think about your story and how it connects to your work and really think about the connections there. What are the moments in your life where you started to become interested in this work? Where were your epiphanies and how did those tie into what you were dealing with as a person? And I would really stress, as I do to all my clients, the emotional side of things, the experiential side of things, how things relate to family and love and introspection and personal emotion. Not necessarily just things like facts and figures and dates and times, but how were you feeling at certain points in your life and then how does that connect to the work now and the values that you have and all that. So I think that's the main thing and that's a hugely beneficial exercise to spend months pouring over.
Yeah, it really is. And you've made comparisons a couple of times between the work that you do, helping people communicate and the act of communicating through a book. And I know for a fact that there's a great deal of overlap between those entrepreneurs who become authors and those that want to expand their public speaking. What are a few tips that you might share kind of as an expert in this area for those that have written a book and are keen to translate that into a speaking career?
Again, I would say becoming crystal clear on your own story, because if you think about it from a pitching perspective, to pitch a potential event manager or program director who's going to book you to come speak, what is the little blurb that they're going to share with their guests that's going to make people want to show up and sit down? So a lot of people would think, oh, it's just the topic, but there's a bunch of people who will talk about the same topic as you. So what is your connection to that topic, and why are you an interesting person and a different voice in a sea of voices about that topic? Chances are whatever you talk about, there's 15 other people who would also be covering it. So becoming clear on your little niche as an individual, and I mean, I think in general, your niche comes from your personal story, but it could also come with something particular that you've done or invented or thought of, but also that personal thing and that's what's going to draw people there.
And then, yeah, who is it for? That's the thing I still struggle with, but I know that the more and more I think about that and figure it out, the more speaking gigs I'm going to get is, who am I trying to speak for and why do they need to hear what I need to hear? And then again, what are their problems? What problems are you solving with your talk? Is it just you getting to talk about how great your company is? Well, who's going to want to go see that? There has to be some sort of problem that you are solving for your audience or some kind of message that you can give them that will make their lives better. And so getting crystal clear on that I think is also really, really important. And then in terms of structuring the talk, don't overfill it with content from your book.
Pick one lesson that you hope the book achieves, and then maybe make three points on that lesson over the talk and restrain yourself as much as possible. As you can probably tell, I have a difficulty restraining myself from overexplaining, that's my work all the time. Say less. Say less, and you'll say more. And so come up with, I have a little thing I teach called the Problem Solution Prize Structure. Come up with a problem your audience has, what's your solution to that problem? And then what's the prize the audience gets when they implement your solution to their problem? And if you can sketch that out on a piece of paper under the Heading Problem Solution Prize, if you can do it in three sentences, then you've got the structure of your talk and then you can fill it out as needed.
But if you come up with the problem solution prize and for whom, who is that for? Then you've got a talk. And the clearer you can make that in your communications with event managers, your communications with program directors, communications with heads of learning and development at companies, depending who you want to speak in front of, then they'll understand the value of it and be much more likely to hire you.
That's gold. Wonderful. Will, how can people get in touch with you to learn more about the work that you do and perhaps how to work with you?
Yeah, so our website is www.outloudnow.com, and you can also email me at firstname.lastname@example.org for any inquiries. And the other place to find me is on social media, most particularly is LinkedIn, Will Greenblatt and Instagram @WillGreenblatt as well. I try to post daily speaking tips and motivational quotes or whatever it is that will help keep people on track to keep the way they communicate at top of mind. That's really important for me is my message to the world, is to keep the way you communicate at top of mind. Yes, you need to work on what it is that you actually do, but you also constantly need to think about the way you're communicating. And the more you can do that, the more you can cultivate a curiosity in people. So yeah, not to go off on another tangent, but @WillGreenblatt, LinkedIn and Instagram and yeah, those are the places to go.
Awesome. Well, we'll put those in the show notes for sure. And I can back up that the videos that you do on social media are fantastic. And in particular, I'm so impressed at how disciplined you've been at continually showing up and adding value for your audience. So thank you again Will for giving generously of your time and expertise. It's incredibly helpful for our audience to learn more about how business owners like you have journeyed from entrepreneur to author, and also your expertise around communication in general has been invaluable. So thank you so much.
As we wrap up this episode of Entrepreneur to Author, remember this, now is the time. Time to write, time to publish, and time to grow. I'm Scott MacMillan, until next time.