Five Lessons For Starting a Speaking Career

So you want to get into speaking?

Recently, I was invited to speak to a group of individuals exploring how to get on more stages and establish themselves in the speaking world.

I did it by accident, but I have some lessons to share.

By “accident”, I mean that when my first book came out, The Transparency Sale, I wasn’t super confident that people would like it. I’d speak and teach for a few months, then go back to the Advil-consuming world of being a Chief Revenue Officer again.

Eight years later, I’m one of a small group who have earned a CSP® (Certified Speaking Professional), which requires you to have spoken over 250 times (for $) over a 5-year period, along with all sorts of other requirements. My plan is still to do this forever.

Here were my big lessons:

1) Prove It Before You Start:

When I was getting started, a prominent speaker gave me this advice: Find an audience who will host you – and don’t charge them. The only ask is that you have a professional videographer there to capture everything.

Then, use that video to create an initial “speaker reel”, clip it up into segments and post them, and start to show the world that you can command a stage, and won’t make an event planner or sales leader look bad for hiring you.

I called someone who had worked for me in the past, who was now running enablement for a company in Indianapolis. He immediately said “yes”! I hired a local videographer, who was amazing. Once everything was put together, I started sharing. Many other previous peers and co-workers who saw my message and could visualize me in front of their audience, based on the video evidence from that first freebie, formed the foundation.

2) Get Coaching:

I was always pretty good in front of an audience. At most engagements, I was always near the top in terms of scores. However, “near the top” isn’t going to get you more audiences or even pay the bills.

I hired a coach who helped me with stage command, storytelling, refining my message, and becoming associated with something. For me, that was turning transparency into a revenue superpower. 

I also got a lot of value from joining the NSA (National Speakers Association), especially when the world shut down due to COVID. There were and continue to be individuals way out ahead of me, in the places I always want to be. They convene there.

3) Prove It Every Time:

I don’t prospect. I don’t cold call event planners, email them, or market to them. My prospecting involves viewing every single audience member as a potential prospect or referrer.

That means, treat every single engagement like it’s the most important engagement you’ve ever had. Because someone in that audience might just be an event planner or a leader in the future, and think of you first when they need someone.

I gave a talk in early 2019 to a group at 1871 in Chicago. No pay. Not even my target audience…it was just a group of entrepreneurs.

Well, a marketer from a multi-billion-dollar technology company happened to be in the audience. Signed a 16-city agreement to tour the country (and Canada) speaking at a tour they were doing to bring their new solution to market.

Today, every single engagement of mine is via a referral, repeat, someone moving from one company to another, or someone who once sat in the audience years ago and now needs some help for their team.

(In one case, a CMO was in her home on a Zoom discussing a need to find a speaker for their kickoff. Her husband overheard and told her, “Look up Todd Caponi. I heard him a few years ago.”)

4) Commit:

I left my CRO role to write a book. Literally an hour after resigning, I had a conversation with a mentor friend of mine over coffee in downtown Chicago. After telling him what I was doing, he said this to me:

“Todd, look me in the eyes and tell me you are going to say ‘no’ to everything for the next six months.”

After some hesitation on my part, he said, “Look, you are going to get calls for what sound like incredible roles. If you’re only partially in, you might as well not be in at all. If you focus on this business and craft for six months and it happens not to work out, you will be MORE valuable to potential employers, not less.”

Two weeks later, I was offered a CRO role. A lucrative one with an impending exit. I said ‘no’ so fast, and thank goodness I did!

5) Buckle Up:

This type of work is a rollercoaster…with huge ups and downs at the beginning, that eventually start to smooth out over time. Five inbound inquiries in a week, followed by none for two months. But, if you’re good, the more seeds you plant (see #3 above), over time, things will get better. I had another mentor almost shout that at me. “Todd, you’re good at this. Try to relax!” And, sure enough things took off again.

Finally, the common question that comes up – “Do I need a book?”

Well, I’ve written three of them now. However, I don’t think it’s a requirement for success at all.

It helped me get things moving and gave me early credibility. But that’s not the path for everyone. I know plenty of successful speakers who don’t have a book. Oh, and I know a few people who wrote books, and it didn’t do anything for them.

My gut tells me two things about it:

1. It needs to be a “real” book, not a rushed, self-published 50-page brochure
2. It needs to say something different, that you’re putting your stamp on

I’ve seen plenty of books that may do more harm than good for a speaker, that were treated like, “Hey, I wrote a book!” business cards instead of something truly focused on uplifting whatever groups you intend to speak to.

The bottom line is this: There are plenty of ways to establish a speaking business. However, proof seems almost more important in this business than any ROI could ever do. Build that proof immediately, invest in your ability every day, and treat every engagement and audience member like your next client. Aside from the rollercoaster, I’m having the greatest time I’ve ever had in my career.

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Todd Caponi, CSP® fell into sales and fell in love with the decision science and history behind it. He’s held multiple sales leadership roles, helping build one company into Chicago’s fastest-growing, another to an IPO and nearly $3B acquisition, and earning a Stevie Award as Worldwide VP of Sales. Todd is the author of The Transparency Sale, ranked by Book Authority among the best sales books of all time, and the award-winning The Transparent Sales Leader. His latest book, Four Levers Negotiating, was released on January 27th. He now speaks and teaches revenue teams worldwide and hosts The Sales History Podcast.

Reach out (email to info@toddcaponi.com) – for inquiries about speaking at your event or sales kickoff, for programs to upskill your customer-facing teams and leaders, or just to nerd out on sales or sales history.

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