How Tough Can It Be? The Aspiring Speaker Checklist


This past week I received 19 – yes, NINETEEN – messages from friends, business associates, peers, and random strangers asking the same thing:

“Can I take you to lunch and ask a few questions about the speaking business?  I’d like to try my hand at making a career of it and thought you’d be the perfect person to ask.  Let me know when you’re available.”

First off, I’m honored anyone would feel I’ve “made it” to a level they feel compelled to ask me for advice.

Second, I wrote an entire Chapter called “Mentors” in my new book, “The Promise To The One”, and it recalls my attempts to be mentored early in my career by those whom I thought had made it, and how not one of them was willing to help me…so I made it a point to always do what I can to lead those asking down the right path.

Third, perhaps there are some reading this weekly blog that are interested as well?  If so, I hope this helps.  And if the thought never crossed your mind, I would assume this may be of interest to see what it takes, at least from my perspective.  I mean, hey, if you have a story to tell, and want to get on a stage, then maybe speaking is for you?

  • DISCLAIMER: Before writing this post I consulted a few of my dear friends who have made it as Speakers, and my favorite response was from Chuck Gallagher (who speaks on Ethics in the workplace and is incredible) and he said he received this advice when he began over a decade ago:
    • “I would tell them you can either do the Cheap & Slow Path, or the Expensive & Quick Path.  It’s the equivalent of opening a restaurant because you are good at making hamburgers at home.  You go to Costco, buy all of the ingredients, cook them up, then go rent a building, make logos, signs, start getting the word out, run your entire store, put the furniture together, run accounting, seat the customers while cooking, until you can afford employees, clean the place, too, and hope to sell some food, and eventually pray you’ll make some money.  That’s the Cheap & Slow Path.  Or you can do the Expensive & Quick Path and go buy a franchise from McDonald’s.”


The Aspiring Speaker Checklist 

So, you want to be a Speaker?

Here is where you begin – 22 POINTS about to Launch you (if you don’t already have a viral TedTalk, movie made about you, or a best-selling book):

  1. Set aside $20,000 to invest in your new Business
  2. Create your Incredible, Amazing, One of a Kind Keynote Speech that needs to be 45-60 minutes long (you will refine, work, and adjust this for the rest of your career.  On average, this one step, to get it to a 5-figure fee commanding level, can take anywhere from 5-10 years to start, just FYI)
  3. Create or invest in a Web Site that will get you events and convince meeting professionals to hire you (ave. cost is $10k for a good web site and hosting, great site is upwards of $25k)
  4. Create or invest in a Demo Video that will stand out above the Speakers you are going up against (ave. cost is $5k for a good video, upwards of $15k+ for a great video)
  5. Create your Branding, Logos, Marketing strategy, Content, Copy, and all the World will know you for (branding & marketing specialists and strategies can range from $5k to $25k)
  6. Devote Daily to Social Media and sharing relevant content, that is entertaining enough for others to LIKE, Comment, and hopefully Share
  7. Write a BLOG at least once a week, preferably more, in order to establish yourself as the Expert in your Field, and which will help your natural Google listings on SEO
  8. Create a YouTube Channel, Public Facebook Page, LinkedIn Profile, and keep them updated at least weekly with new Videos, engagement and interaction options for Followers
  9. Gather names to subscribe to your Newsletter list in order to send your future offerings their way
  10. Invest in a robust CRM to keep track of requests, your sales efforts, and the confirmed events
  11. Be available 24/7 via Text, Email, Phone, Zoom, ready to answer any questions or needs from inquiries and confirmed clients
  12. Begin writing your Book, which will establish you further as an authority on your subject
  13. Decide whether you will self-publish your book, design, layout, and create it from start to finish, and print copies to store in your home/office, or if you prefer a Publisher and begin making inroads to pitch your book
  14. Join the National Speakers Association and Toastmasters, and attend your local Chapter meetings while learning from every speaker who comes through town and choose which one’s advice to follow
  15. Have a Gifting strategy in place for all referrals, agents, bureaus, and events that have had you speak
  16. Accept every request to be on Podcasts, Interviews, Virtual Summits, and promotional opportunities that can get you on a stage or in front of new potential listeners
  17. Invest in a Speech Coach to fix the speech you created back at #2 (Good Coach: $6-10k, Great Coach: $25k)
  18. Invest in Performance, Acting, Comedy, Speaking, Entertaining Coaching, and Conference/Workshop/Summit Attending (~$25k+)
  19. Buy your own camera equipment and teach your children how to use it, after you’ve invested in #4, and have them create your new Demo Speaking Video
  20. Watch dust gather on your camera equipment as you go back to #4 and look for a new video person
  21. Re-write your web site, rebrand, change your logo, fix your cards, and beg your web site creator to make at least one of the changes you sent every 6 months… (this is normal with a large web site production company)
  22. Go to the bank and get a HELOC due to undershooting the cost suggested at #1, and instead plan on $50-100k+



You can probably tell some of this is funny and feels like a joke.

It is…and, well, it isn’t.

As in, not at all.  I’m shooting straight here, so just take it for what that’s worth.  This is not an easy side hustle kind of situation, this is an ALL-IN kind of career.

If you do what I’ve written above then you are doing it the Cheap & Slow Path.

I am not exaggerating.

Ask ANYONE who has made it in this business and – with rare exception – I haven’t embellished many of the steps above.

Do you want a Cheaper Path?  You can do that, and yes, you can bootstrap and learn how to edit video, create a web site yourself, do your own photos, speech writing, editing, copy, not attend meetings with peers to see how to improve and collaborate with others, or invest in coaching, and you could make it…but I don’t know anyone who’s done it that way.



If you want the other option of Expensive & Quick Path here are the following 5 Steps: 

  1. Set aside $100-200k to invest in your new Business
  2. Create your Incredible, Amazing, One of a Kind Keynote Speech that needs to be 45-60 minutes long (invest in speech, messaging and performance coaching of $25k minimum)
  3. Create or invest in a Web Site that will get you events and convince meeting professionals to hire you (invest upwards of $25k)
  4. Create or invest in a Demo Video that will stand out above the Speakers you are going up against (invest $15k+ for a great video)
  5. Create your Branding, Logos, Marketing strategy, Content, Copy, and all the World will know you for (invest in branding & marketing specialists and strategies $25k)

And then make sure, in some way, you do #6-16 as listed above to stay in the game and run your business.

If you think this is SHOW BUSINESS then you are CORRECT!

And as I’ve heard it said, “The word Business is double the length of Show, and you need to work on the Business that much harder than the Show”.


“What if I’m already kind of a Celebrity?” you ask yourself, while snapping another selfie for Instagram…

Ok, say you had a TedTalk that went VIRAL, wrote a NYT Best-Seller, had a movie made about your life, won a Gold Medal in the Olympics, Summited Mount Everest, or some other variation on celebrity/fame…

First of all, good for you and…LUCKY!

Your list will be shortened and easier, but it still includes doing everything from 1-16 listed above, with the exception of needing to choose who your agent and talent management will be and ensuring they’re doing good work for you.


“What if I’m just wanting to be a Speaker and don’t want to do everything listed above?”

Truth is, ANYONE can be A SPEAKER.  It’s not THAT tough.  It’s just whether or not you want to be a GREAT Speaker and have a GREAT CAREER.

The most successful Speakers I know have invested upwards of $250-500k in their businesses – just like any other startup – and it has afforded them a beautiful and wonderful life.  But one that takes EXTREME work, consistency, and development.

I have aspiring speakers ask me every day how they can “make it” without the financial investment I’ve outlined up above, or the amount of work such as is required for a new business to take shape, and I just can’t say there’s a simple way.

If there were we’d all have done it.

I even let them know that I can’t meet for lunch until they’ve proven they’re willing to invest even a small portion in themselves by BUYING MY ONLINE COURSE of 6 hours of video and a 60+ page workbook for $197… and most won’t even do that for themselves.  They just want to talk.  And that tells me immediately they’re not going to do anything with what I’ll tell them at lunch.

If they want me to Coach them, I’m happy to on a per project basis.

If they want me to Mentor them, I have created these resources listed above in order to help mentor them to find the right path.  Many other writings, including an ENTIRE Blog devoted to this career which I maintained for 2 years, answering the most pressing questions you will have along the way.

But I can only MENTOR those who have been in the Business and taken it seriously for at least 5 Years.  5 Years tells me they’re on their way.  Few exceptions.


So, the question I have for you, if you are STILL an aspiring Speaker after reading all of that:

Is it Your PROMISE to Become a Speaker?  Because if it is, then you’ll make it happen.


Leadership Expert * Author * Speaker Hall of Fame

The Promise

Ready to become a better Speaker for your next Presentation?  Let Jason show you how click here

Share this post

6 thoughts on “How Tough Can It Be? The Aspiring Speaker Checklist”

  1. I once had the opportunity to attempt to get into the New York ballet. I had been dancing since I was 3 years old, I was 18 at the time, and I loved it. I was told that I would have to train full time for two years to be able to audition. After some soul searching I decided against it. I loved dance, but not enough to put in the hard work (I haven’t regretted it). My point is that no matter what it is, even if you love something, are good at it, and have connections to the right people, you still need to put in the time and the work in order to succeed. Thank you for that reminder.

  2. Thomas Cantrell

    Nice! Way to go Raptor Man ~ Yes, once again, you’ve hit it on the nail head in a Jason Hewlett sort of way — meaning brilliant, funny, and so very much quite true (this is National Superlative Week). I’m grinning from ear to ear at the humor, irony, and truth in all you have said. ox

Leave a Comment

Your email address will not be published.

Latest Tweet