In this episode of Pitch Please, Mike Thibodeau teams up with Will Greenblatt, co-founder of OutLoud Speaker School, to unpack the art of pitching that takes founders from an elevator pitch to a successful exit. Will, with a background in acting and coaching startup founders, has helped companies raise millions by honing their storytelling and delivery skills. In this episode, he shares insider tips on how to captivate investors, build confidence, and avoid common pitching pitfalls.
Will’s insights come from years of experience working with entrepreneurs in top accelerators like Techstars and Founder Institute, where he's helped founders raise over $350 million in funding. This episode breaks down the elements of a perfect pitch and how to develop stage presence that gets results.
In This Episode, You’ll Learn:
• Creating a Compelling Founder Story: How to craft a personal story that resonates with investors and creates emotional buy-in.
• The Perfect Pitch Structure: What information you should include in your elevator pitch, and how to expand it for longer investor presentations.
• Body Language and Vocal Tone: How your physical presence and vocal delivery can influence an investor’s decision.
• Answering Investor Questions: Strategies to handle tough questions and maintain control during the Q&A session.
Takeaways
• Not all pitches are crafted equal; understanding this is crucial.
• A pitch should be a conversation, not a monologue.
• Your voice, face, and body must tell the same story.
• Investors are often investing in the founder, not just the idea.
• Simplicity is key; avoid overwhelming your audience with information.
• Your unique story is your greatest asset in pitching.
Chapters
00:00 - Introduction to Crafting Successful Pitches
03:05 - Will's Unique Journey to Entrepreneurship
06:43 - The Art of Pitching: Teaching vs. Acting
08:32 - Key Components of a Powerful Pitch
10:23 - The Importance of Delivery in Pitching
12:10 - Engaging Your Audience: The Role of Energy
13:28 - Building Connection Through Storytelling
16:29 - The Founder Story: Why It Matters
19:43 - Investors and the Human Element
23:31 - Common Pitfalls in Pitching
27:30 - Preparation and Presentation: The Day of the Pitch
34:19 - Overcoming Stage Fright and Building Confidence
39:51 - Audience Engagement Techniques
42:36 - Handling Q&A: The Importance of Authenticity
53:58 - Final Thoughts and Key Takeaways
About Will
Will Greenblatt started acting in film and TV at the age of seven, starring in The Homecoming with Oscar® 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 a startup in China. He founded OutLoud Speakers School in 2017, teaching public speaking & communication skills to entrepreneurs and executives. He has repeatedly spoken and coached at Google, Wayfair, Boston Dynamics, TechStars, Founder Institute and Ericsson, as well as providing coaching to over 4500 individuals virtually worldwide.
Will’s clients have won numerous pitch competitions, got deals on Dragon’s Den, and raised over $350 million USD in investment. He’s also a nominee for both “Newcomer of The Year” by the Speaker Awards & “Highest Rated Mentor” (Global Startup Mentor Awards) and he was called “Canada’s best pitch coach” (Jordan Jocius, Founder Institute Waterloo).
About Speaking Heroes (OutLoud)
Speaking Heroes (formerly OutLoud) is a community for solopreneurs to develop their storytelling & communication skills with expert coaching, homework assignments, & peer feedback.
Want to Get Involved?
Speaking Heroes community: https://www.skool.com/speakingheroes/aboutWill's LinkedIn: https://www.linkedin.com/in/willgreenblatt/Will's newsletter The Greenblast: https://greenblast.beehiiv.com/
