
Training for Speakers, Entertainers & Entrepreneurs ~
The #1 complaint I get from anyone in this business is that they don’t have enough bookings.
Ready for the truth?
Numbers don’t lie. Time to be very candid with you my friend.
I am going through some crazy weird stuff myself.
Over the past 6 months we have seen a huge and surprising drop in confirmed bookings from The Promise web site and videos. As I make a living from bookings as a Keynote Speaker this has been a very sobering experience and financially challenging.
15% conversion rate when an event planner and potential buyer watches my videos or visits my web site. That is not good.
And yet we are constantly revered by those that have had me at their events, told by 90% of event planners I am the highest rated speaker they have had in years, or ever. So what is happening?
Time for some truth finding and quick adjustments!
Question is: What are your numbers and are you doing something about it?
Here’s our plan and what you can do, too:
- Keep Everyone in Place – This is not an issue of whether I have the right people working with me. They are the best I’ve ever found. The challenge is on the content creator, and that is me. I could blame anyone and everyone, but it all comes down to what I say goes on the site, on the video, etc. It’s up to me to deliver great content when on stage and make sure it’s captured…sadly we are finding I haven’t done that as effectively as I should. Sure, I still get standing ovations, but that’s because I know how to generally will people to get out of their seats when I’m in front of them in person! Yet in an unedited, ready for YouTube video, that just isn’t captured because the way I deliver it doesn’t convert as well to video! How the web site is written comes from me, even if I run it past editors and designers, it’s all on me. So, we keep the great team in place, and move forward to make things better. It all comes down to me and my willingness to own what’s going on and what I’ve done to myself. Who is on your team and can you…
- Be Honest with Yourself – As I have researched where my events are going, who I’m “losing” out to, essentially it comes down to my web site and videos all being about one person: ME. They don’t scream what the Client will receive if they hire me. While the web site is up you should go look at it, because by the end of August we’re planning on having it completely revamped, but look at how much it shines the spotlight on me rather than the result. Same with the videos – although we just fixed the banner at midnight, so check out how cool it looks. Although they are good videos, they are about me, not the ROI of having me speak at that event. This is very typical of someone like you or me coming from the Entertainment world and the challenge of transitioning to the Speaking corporate market. How honest can you be about your products when you look at them through the eyes of the buyer?
- Ask The Right People For Advice – When I found out who is getting the events instead of me (easy to track, just look at the web site and meeting agenda of the gig you just lost), I began studying the web sites of those speakers like a crazy person. And then I literally contacted their web site designers, video editors, as well as asked very pointed questions to those who are trying to sell me but haven’t had success. Perhaps they were surprised to hear from me, but when you realize there is a leak in the boat, you either jump out and hope for rescue, or you do everything you can to fix the leak! I am in troubleshoot mode, and getting advice from those I trust is incredibly frustrating (to realize my ego is now going to be hit by truth), but equally liberating to know others have my back and will tell me like it is.
- Get Down To Business – Currently, I am digging through footage that has long since gone un-utilized in terms of video. Why didn’t I use it before? I don’t know. I have reached out to my friends, colleagues, and people who are way smarter than me, asked their advice, even requested what the web site might say, and truly miracles and blessings of their kindness are coming my way. But it comes down to work. Work on every aspect needing improvement. It’s not going to change itself. I spent 18 hours the past 5 days cranking on things I’ve avoided for months, even years. I apologized to my family but gave them a heads up – “hey, here’s what’s happening in our family business…if you are bleeding come get me, otherwise, I need to put my head down and get working”. They understand and life goes on. Do the work.
- Invest Wisely While Downsizing – This one is tricky but works. Investing in improvements to our backyard at this time and season of down bookings would not be wise, rather putting money into client retention gifts, marketing efforts, and taking business a bit more serious is where your money needs to go. As I was looking at our spending as a family and business I realized some things could go: The gym membership we rarely use (we have a home gym and a community one for free), the cost of an epic RV trip each summer (this year we are sticking around home), lunches and dinners outside of the home for both family and clients (kids would rather eat at home, and I don’t love taking the time to meet clients for lunch because I am often stood up…so I have cut those out of my life and instead funnel them to phone calls or Zoom/Skype). Sadly, the downsizing affects our family life and enjoyment, but in truth we aren’t missing out on much, just facing the facts. Instead we are investing in things I haven’t done for years: purchased LinkedIn Premium (to find all the people that seem to have switched jobs since they entered our CRM), subscribed to the Wall Street Journal (this has helped me see what buyers in the corporate market read and think about, thus my blogging for them has shifted), invested in a better selfie stick and camera (as I’m not comfortable with the challenge I face in doing 39 takes with a video guy shaking his head at me in disapproval, so I prefer to do this solo til I get it right). All of these investments are helping me get closer to my promise to have a great career and create a wonderful life for my family. Where can you downsize and invest instead?
I wish you the best in your efforts and hope you know I’m going through it, along this path with you, too. That’s the beauty and the disturbing reality of a career from the stage – even those we see as having the lights shining brightest on them are going through some deep, troubling things, all while being celebrated for all to see. It’s some bizarre highs and lows. Why is it that people acclaimed on stage have in their dark times relapses with addictions, or turn to doing things that drastically affect their lives? Because mostly we are in this alone. Realize you’re not alone, at least not as long as I’m around to share what I’m going through with you.
- Postscript & Note:
The words in this blog seem to have gone from very practical, immediately implementable business strategies over the past 18 months, to a more philosophical, candid and almost painfully honest resource. If this is something that is helpful to you then we will keep on this path as you come along with me. If you are in search of other issues, needs, or ideas from me, let me know what you’d prefer to read. The amount of comments on these posts are so minimal I’m not sure who is reading, but appreciate thinking it might help one person to know what I’m going through and how I troubleshoot the ups and downs of this type of career, and how you can do it, too. Not looking for comments for some ego boost, rather it helps me know what direction to write. As therapeutic as this blog is for me, it’s also already in my journal as well, so if it’s not helpful and you are in search of something else please let me know.

Jason Hewlett, CSP (Certified Speaking Professional), CPAE Speaker Hall of Fame, is a Keynote Speaker for the largest corporate events in the world. His primary message, The Promise, is essential for Leadership, Management, Sales, Marketing, Direct-Sales Companies, and is a combination of engagement and entertainment meets inspiration. Jason has even received standing ovations from IT guys. He has been acknowledged as life-changing by Conference Attendees, C-Level Executives and Hollywood Elite. jasonhewlett.com

Please click here to learn about how Jason Hewlett, Speaker Hall of Fame, introduces the opportunity for you, or someone you love, to have the gift of learning how to create a Career From the Stage and begin moving toward fulfilling a lifelong dream as a full-time speaker, performer, or entertainer.
I love all the tips in this post. I think we need to constantly evolve and invest into marketing strategies. It’s good to know how you invested in LinkedIn and Wall Street journal. Also the strategies behind your website. Right now I feel my website is a great landing page to give me some legitimacy but now I need to add value and let potential clients know what problems I solve.
Your site is very good, happily send it along to my clients, and grateful to know you read these posts 🙂
I think this post is spot on. I read it after an interesting experience this morning working in my yard and now I’m realizing what a big teaching moment it was for me!
Over the past few months, a tree in my front yard has been dying. I reluctantly decided I was going to spend my time hand watering it, so, for the past few weeks, I’ve spent about 30 minutes a week watering it with a hose. The strange and frustrating thing is that it was clearly visible there was a drip system set up for this tree, but for some reason, I never saw water coming out of it. Other trees and plants in the same area were getting water, so, I concluded that the water source for the dying tree was from my neighbors sprinkler system. So, basically, the life of this tree was subject to whether or not my neighbor’s chose to turn on their sprinklers.
This morning, instead of doing a traditional work out at gym, I dedicated my work out time to shoveling dirt in my backyard to resolve if the source of the water for that tree came from my house or my neighbors.
I started at my source. After about 20 minutes of digging, I verified the source of the water was indeed from my sprinkler system. One pipe branched out from the rest of the system and ran across my yard in the direction of the dying tree. After a few more minutes of digging and scrapping away gravel, I found my problem. The drip system was kinked about 6 inches from the tree. Apparently, when the sprinkler system was being installed, someone folded over a part of the drip system, kinked it with electrical tape, and then forgot about. Maybe for some testing? I’m confused why. Eventually, that part of the hose was buried in gravel and out of site.
Now, the lesson from this could be, “You could’ve saved yourself 30 minutes of digging if you just checked for kinks first.” However, thanks to the intense digging and checking, I now have an understanding of how my entire backyard sprinkler system works. I’m in the process of the landscaping my backyard right now and feel confident in my next steps knowing I already have a pipe that runs through my entire backyard. I could have hired a professional to come check this out and may end up doing that to have an entire system installed, but now, I know that master plan of my yard. Like you said, it comes down to me and my willingness to own what’s going on! And it’s a wonderful feeling when that is being done! How ridiculous would I have been to let this tree die and then put the blame on my neighbor. As I think about it, any time I’ve experienced any type of success on a social media platform or on a stage somewhere, it’s been the result of my willingness to do some digging, do some trial and error, and be okay with whatever I find, be it heaps of treasures, or hoards of hard truths.
This is fascinating as an example. Love it. Thank you for sharing and contributing.
Those who make a living in front of an audience, in any context, can’t help but cater to what we think they want. Being a truth-teller or thought-leader is very different. It often means presenting ideas and concepts in such a way that people are afforded a new perspective or understanding without being made to feel bad, wrong, or stupid.
The difficulty is that we’re all creatures of habit, and even though what’s currently being done isn’t working all that well, or at all, it’s familiar so we stick with it.
Jason, you are becoming a master in this realm. You continue to push forward into uncharted territory – still holding to your core mission of feeding people in such a way that they grow to be stronger, happier, more valuable human beings.
Knowing you, and knowing this about you, goes beyond inspiration or motivation – it goes to provocation.
You provoke me, in such a loving way, to not give up, to try harder and to do better … and I thank you for that!
Means a whole lot that you’d comment and share this Barry. I love to provoke! Need to do it more 😉 Love you man.
I read everything you post. This was very helpful to me in that it showed me that if you have so much work to do, then I don’t even know where to start in getting my speaking back up and running…ugh! I’m not even close! Thank you for the transparency and realistic look at how difficult this business really is. I won’t give up, though!
Don’t ever give up on it. Constantly push, always tweak and improve. I’m grateful you read these blogs, great to know. Please never stop, you are too good to stop! Glad to know you won’t!
An excellent read and good “kick in the pants” for me. Thank you, as always.
Haha! Thank you sir! Good reminder for all of us!