Breakthrough Speaker Mastermind

A Curated Peer Support Group for Keynote Speakers

The best way to increase your speaking fee and take your craft to the next level, is to spend more time with other speakers.

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About Breakthrough Speaker Mastermind

Join a curated group of 10 professional keynote speakers for a 6-month journey to grow your speaking business, increase your fees, and amplify your impact.

  • Connect and build powerful relationships with a small, invite-only group of other successful Keynote Speakers, curated by Smiley.

  • Surround yourself with other talented, professional speakers to improve your craft, help you find you more speaking gigs, and connect with agents and industry professionals.

  • Spend 2 intensive training days learning about the business of speaking and workshopping your keynote, followed by 6 months of deep work investing in growing your speaking business.

  • Get a new and improved speaking reel: a professionally edited 2-minute video, to book more gigs.

  • Get personalized feedback on your story, your speaking business, your keynote, your website, your reel, and your marketing materials.

  • Get 1-on-1 coaching support from Smiley.

  • Have an Accountability Buddy to work with throughout the Mastermind and help you achieve your speaking goals.

  • Connect with special industry guests (including main-stage TED speakers, top corporate speakers, speaker agents, conference organizers, meeting planners, etc.)

  • Gain access to a private Breakthrough Speaker Mastermind Facebook group to stay connected during and after the Mastermind; discover new speaking opportunities, share resources and ideas, ask questions and get feedback.

What’s Included

  • 2 days of in-person training, with personalized feedback on your keynote from your Mastermind Group

    2-day (16-hour) training in San Francisco Bay Area (travel not included). Day 1 we will learn about the business of speaking; Day 2 we will workshop your keynote presentation.

  • 6 90-minute Monthly Zoom Video Meetings with Smiley and your Mastermind Group

    All Zoom video calls are recorded in case you miss one.

  • 2 60-minute 1-on-1 coaching sessions with Smiley

    1 60-minute video coaching call with Smiley at the beginning of the program, 1 at the end.

  • 1 Accountability Buddy from the Group to connect with weekly in-between Zoom meetings

    Your Accountability Buddy is specifically assigned to you after your first coaching session; to match you with a speaker based upon your topic, speaking experience, goals, and potential for collaboration.

  • 1 new Speaker Reel

    At the end of the 6-month Mastermind, get a new and improved version of your 2-minute speaker highlight reel, professionally edited and optimized for you to book more gigs. All footage and material must be provided by the speaker, we’ll handle the editing!

  • Personalized feedback

    Receive feedback on your brand, keynote, speaking reel, and website, from Smiley and other Mastermind members.

  • Weekly homework assignments

    You’ll receive practical exercises, videos to watch, recommended reading + podcasts, etc. to do every week in between our meetings.

  • Special industry expert guest appearances

    On some Zoom calls, we’ll welcome top keynote speakers and industry experts to share their wisdom. We’ll also be joined by experienced speaker agents and conference organizers to teach us what event planners are looking for when booking a speaker.

  • 2 signed copies of Smiley’s book: The Breakthrough Speaker

    One for you, one for a friend.

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What You’ll Learn

  • 2 intensive days of deep work: Build meaningful relationships with 10 other professional speakers, share knowledge, get real-time direct feedback on your keynote and action steps for the next 6 months of the program.

  • 6 months of professional growth: Personalized feedback to identify your speaker strengths vs. speaker blind spots (growth areas to focus on in your speaking business). Improve your story, your keynote, your website, your speaking reel, and your marketing assets.

  • Keynote design: Write, practice, and perfect a keynote that gets you booked again and again.

  • Speaker agents: Book gigs without a speaking agent, find a speaking agent, build fruitful relationships with multiple speaking agencies + bureaus so that they’ll always want to work with you.

  • Speaker marketing: Improve your speaker website, make a successful speaker reel, use social media to book more gigs.

  • Speaker platform: establish yourself as an expert, invest in thought leadership, learn how to write a book that will help you book more gigs, how to get a book deal and publish a book.

  • All things money: Increase your speaking fee, practice negotiation tactics, know what to charge for speaking fees for keynotes, panels, fireside chats, workshops; and how to price yourself for corporate clients, non-profits, colleges, and other events.

  • Lead generation and sales: Find more gigs, convert leads into gigs, have successful sales calls with potential clients, close high-paying gigs at Fortune 500 companies and trade associations.

  • Relationship building: Always make your client happy, get referrals and repeat bookings, learn what conference organizers and meeting planners are looking for when they book speakers, master your Q&A, know what to do when shit goes wrong.

  • Speaker lifestyle: Self-care rituals and habits for speakers, how to take care of yourself on the road.

  • Business tools: Run your speaking business like a professional: travel tips, contracts, accounting and legal, apps, tools, etc.

  • Understanding the industry: Increase diversity in public speaking, add interactive elements to your programs, anticipate the future of conferences and experience design.

  • Speaker Best Practices: Learn tricks of the trade, and lessons from the trenches from your peers.

These are just *some* of the topics we’ll be covering


Investment: $5200

Dates: January - July, 2020

  • 2-day Intensive Training: January 11-12, 2020 in SF Bay Area

  • 6 Monthly Zoom Meetings: February 2020 - July 2020

Cohort Size: 10 people

The 2020 Cohort is limited to 10 people to ensure an intimate group with personalized attention and customized programming. Space is on a first-come first-served basis. To reserve your spot: please fill out an application. Selected applicants will be sent payment information.

About You: You are an experienced speaker looking to take your speaking business to the next level

You are a seasoned public speaker/coach/trainer/facilitator ready to find a supportive community of peers to share knowledge, contribute your zone of genius, share your gifts, offer and receive mentorship, and do the deep work required to advance your speaking career.

You’re not new to the speaking industry, you’re not still figuring out your message, you’re not still looking for your first paid gig. You regularly book paid speaking engagements, have done a TEDx talk or delivered keynotes or workshops at major conferences or companies, spoken in front of 100+ people, and want to increase your speaking fees to $15,000 and higher.

Why a Mastermind?

I’ve been a professional speaker for 5 years. I love speaking, but I’ve found that the hardest part of my job is that so much of what I do is done ALONE. Writing my talk alone, practicing my talk alone, rehearsing my talk alone, traveling alone… it adds up to countless hours spent, well, ALONE.

I wanted to create a group where speakers could come together on the same team. To support each other and learn from each other. To share wins, admit defeats, learn new tools, ask questions, get feedback, and improve their craft.

I realized that what I really was lacking, what I was really missing, was being in the company of other speakers. So, I’m hosting the Breakthrough Speaker Mastermind for a small group of speakers to share knowledge, connect in weekly video chats, get personalized coaching, and have weekly 1:1 check-ins with an accountability buddy.

Breakthrough Speaker Mastermind is about curating a group of exceptional high-potential speakers who will show up fully, teach each other, and create a long-lasting community of accountability, mentorship, and professional growth.

“Getting to the top of your field is a challenge, but it’s easier with the support of a strong peer network.”

-Dorie Clark, Harvard Business Review

About Your Host


Adam Smiley Poswolsky is a millennial workplace expert, keynote speaker, and bestselling author of The Quarter-Life Breakthrough (Penguin Random House) and The Breakthrough Speaker.

Smiley helps companies attract, retain, and empower millennial talent, and he has inspired thousands of professionals to be more engaged at work, through speaking at companies like Unilever, IDEO, Salesforce, Genentech, Deloitte, SAP, Pinterest, MailChimp, and TED. An internationally renowned motivational speaker, Smiley speaks about millennials, employee engagement, and intergenerational collaboration at Fortune 500 companies, business conferences, leadership trainings, and universities. Smiley is regularly paid $10,000-$15,000 for his keynote presentations. His TEDx talk has been viewed over 1 million times, and he has done hundreds of speaking engagements, reaching over 50,000 people in 15 countries.

Smiley’s work has been featured in The New YorkerThe Washington PostUSA Today, Fast CompanyForbesInc.EntrepreneurCNN, and the World Economic Forum, among many others. He is on the faculty at Esalen Institute and General Assembly, a mentor for StartingBloc Institute for Social Innovation, and a camp counselor at Camp Grounded: Summer Camp for Adults.

In 2017, Smiley launched The Women Speaker Initiative, a community that aims to increase the number of women and people of color speaking at conferences and companies, as well as ensure that women and POC speakers are paid competitively as compared to their colleagues. The group now has over 2,000 members.

Smiley’s Speaking Clients


“Not only is Smiley a memorable, energizing, and engaging speaker on stage, but he teaches his step-by-step methodology for creating and advancing your speaking career. Run, don’t walk, to work with Smiley!”

-Amber Rae, speaker and bestselling author of Choose Wonder Over Worry

“I've been calling Smiley my Best Friendtor (friend + mentor) for years, as his guidance and support has been beyond invaluable to my speaking career. What sets Smiley apart is his combination of extensive experience and genuine caring—not only does he share excellent and concrete advice about how to level up as a speaker, but he also believes in people and will have your back. I can't recommend him more highly to anyone who wants to take their speaking career to the next level and beyond.”

-Dr. Emily Anhalt, psychologist, speaker, founder

“Smiley is known as a speaker, but truly he's a world class teacher. Whether on stage, in a classroom, or on a phone call overseas, I have been able to apply his lessons to become a 6-figure speaker myself. His energy, enthusiasm, and clarity of purpose is contagious. He's quirky, inclusive, and ambitious. A true pioneer of our time, I'm just glad he's finally launching this mastermind!”

-Cam Adair, speaker and founder of Game Quitters

The Breakthrough Speaker is a practical and powerful guide for anyone who wants to build their personal brand and grow their speaking career.”

-Dorie Clark, adjunct professor at Duke University's Fuqua School of Business, contributor to Harvard Business Review, author of Entrepreneurial You

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Chris Butsch

Mastermind Application

(Please note: this application asks for personal information about your speaking business. This is so I can build a cohort of speakers, with similar levels of experience, who are best positioned to support each other. If you would prefer not to answer a question, that is okay. Your application information will be kept confidential.)

Name *

The Women Speaker Initiative

As part of my work as a professional keynote speaker, I am committed to helping increase the number of women and people of color speaking at conferences and companies, as well as ensuring that women and POC speakers get paid competitively as compared to their colleagues.

I am committed to ensuring that at least 50 percent of every Speaker Mastermind is made up of women, people of color, or otherwise underrepresented speakers.

If you are interested in learning more about The Women & POC Speaker Initiative and our community of 2,000+ members, please join us. It is free to participate. Anyone who supports increasing opportunities for underrepresented speakers is welcome. Please join The Women Speaker Initiative to get involved.

Frequently Asked Questions

Wait, aren’t there 8 more pages of bullshit sales copy and a 94-step email marketing funnel convincing me to sign-up?

Nah. Not my style. If this is for you, awesome. If it’s not; awesome, I still love you.

If you’re ready to make a serious investment in your speaking career that should pay itself back in one speaking gig (if you do the work), then I can’t wait to support you.

I want to work with Smiley, but I don’t have time to do a Mastermind. Do you offer 1-on-1 coaching?

If you are interested in working with me 1-on-1, but can’t make the time commitment for the Mastermind, check out my Speaker Coaching offering.

I can’t invest in this. Can I pick Smiley’s brain?

Over the past 5 years, I’ve spent hundreds of hours supporting my community and offering free advice and coaching to people I believe in and want to support. Nothing gives me more joy than helping others—I’m a Enneagram Type 2 (Helper/Giver). Yet, I’ve learned that if I don’t charge competitively for my time, it keeps me from creating new material, it keep me from doing my best work; and even worse, it makes me resentful of people I’m giving my time too. I’ve reached a point in my career where I can no longer offer my time for free. However, I’ve invested countless hours of time in some incredible free or almost-free resources that will help you build your speaking career (scroll down).