Around the time my first book Building a Second Brain came out in June 2022, I started looking for a speaking coach.

I had just delivered my first keynote to a large audience at World Domination Summit, followed soon thereafter by my Google Talk. These experiences had been not only fantastic promotional opportunities but fulfilling and meaningful for me personally as well.

There is nothing quite like standing on stage and delivering a message you deeply believe in to an enthusiastic, roaring crowd.

At the same time, I could see clearly that “winging it” wasn’t a sustainable strategy for future speaking gigs. I’d been lucky to be offered a couple of valuable opportunities, but I wanted to start pursuing speaking more purposefully, as a skill and a craft that could serve me for decades.

I always like to start new projects by listing my intentions, and this time was no different. I decided I had six of them:

  1. To build a world-class speaking business based on my BASB message
  2. To use speaking to promote sales of both my book and our course
  3. To connect with people on a human level and inspire them to greatness
  4. To generate a new source of revenue for the business
  5. To connect with like-minded thought leaders and learn from them
  6. To master all the major elements of speaking

In other words, I wanted to use my new book as a springboard to launch a full-fledged speaking career, both to grow the business and for personal enrichment.

After interviewing several candidates, I decided to work with Michael Gendler, co-founder of Ultraspeaking. I liked his attitude and philosophy toward speaking, admired the education business he’d built around that philosophy, and the fact that he lived nearby in Los Angeles was icing on the cake.

Here’s what I learned and how I changed as a result of that collaboration.

Speaking as self-expression

I came in hot and heavy myopically focused on learning how to book corporate keynotes, nail big speeches, and maximize my profitability per hour. Like any good coach usually does, Michael quickly pumped the brakes and started asking me some basic questions about what I truly wanted.

I’ve often said in the past that the main job of a consultant is to repeatedly ask “So what are you really trying to accomplish here?” since much of the time we tend to be deep in the weeds on one narrow pursuit.

This turned out to be a fruitful question because depending on what I was trying to accomplish, there were usually far better ways of accomplishing a given goal. Looking at my list of six intentions above:

  • If my goal was to promote sales of my book and course, it would be far more efficient to create online content that serves that purpose day and night, rather than flying to far-flung locations and talking to small groups of people.
  • If my goal was to connect with people and inspire them, I could do that much more easily via local meetups, doing my own coaching, or simply hosting workshops on Zoom.
  • If my goal was to grow the business and increase revenue, there are many other ways of doing that that don’t require trading my time for money.
  • If my goal was to connect with other thought leaders, grabbing coffee with them is probably more effective than speaking on stages.

This exercise revealed something I’ve often noticed about setting intentions: if you have too many of them, no single one is important enough, which means none of them end up being fulfilled.

The intention that couldn’t be fulfilled any other way, and that stood apart, was to master all the elements of speaking. But that isn’t an end in itself. Michael and I spent a good amount of time digging into the root of that desire. The answer we arrived at was obvious as much as it was surprising: self-expression.

Michael’s philosophy, as embodied in the Ultraspeaking courses, is that speaking in public isn’t just about delivering corporate keynotes. It’s about self-expression, a much deeper and broader need that everyone can benefit from, whether it involves speaking up in a meeting of three people, communicating confidently over a group dinner, or simply being able to spontaneously share what you’re feeling in a conversation with one other person.

Ironically, self-expression is also at the root of my work. The reason I believe that curating and organizing and synthesizing information is worth doing is because of what it allows you to express: a message, a story, a cause, an idea. We came full circle and realized that my desire to improve at speaking was rooted in the same core desire that drives all my work: to communicate and connect with people more deeply and authentically.

With this clarified, much simpler intention in mind, we created an action plan with six main elements:

  1. How to make public speaking an opportunity for me to become an amplified version of myself
  2. How to bring playfulness, silliness, and humor into my speaking
  3. How to make my speaking more variable and dynamic
  4. How to speak more spontaneously, with minimal notes or preparation
  5. How to structure prepared speeches for larger, more formal audiences
  6. How to identify the main points of my message, and illustrate them with personal stories

My default approach to speaking is to be overly prepared, which tends to make me too rigid, caught up in my head, and obsessed with hitting every single point. Our action plan was designed to make the whole experience much more spontaneous, and thereby both reduce the burden of preparing my talks while also allowing me to connect with my audience as a human being.

Identifying my main ideas

We met for each session in the studio at my house, and in our second meeting, we began to identify the main messages that I wanted to communicate.

You might think that I already knew exactly what my message was, but the problem with being immersed in a subject every day is that it’s almost impossible to avoid losing the forest for the trees. The idea of a “Second Brain” is so expansive and multi-faceted that I could potentially address any one of a dozen different aspects of it.

We did a live brainstorming session, with Michael repeatedly asking me questions and prompting me to expand on certain points while he took notes. The result was a fascinating brain dump of ideas that could serve as takeaways from any talk I gave. Here is a page from Michael’s notes, which he shared with me afterward:

A page from Michael's notes

Seeing my own thoughts reflected back to me through another person’s perspective was tremendously helpful, allowing me to notice that certain subtle and complex topics I found interesting were unintelligible to others, while others I found basic and obvious were eye-opening.

I digitized those notes and, on my own, bolded the points I thought were substantial enough to support a talk. These became an “idea bank” I can turn to any time I need to deliver a speech.

My idea bank note

Michael also helpfully summarized what he thought were my most salient and unique ideas in a follow-up email. Again, this is a priceless window into how someone not fully immersed in this topic views it:

Note with feedback from Michael

Practicing spontaneous speaking

Once we had a set of ideas that I knew enough about to speak on, I was surprised that Michael wanted to go right into spontaneous practice. I tend to follow rather thorough, overly detailed processes when creating new things, so going straight to delivery felt like an uncomfortable leap.

Michael set a timer for three minutes, asked me to pick any idea from our list, and before I knew what was happening, he said “Go” and I found myself talking. Without an idea where I was going and absolutely no outline or structure in my mind, I was pleasantly surprised that I could still make it engaging. In fact, I could quickly tell that it was more entertaining than if I had been sticking to a strict outline.

Michael set the timer again for one minute, and I went again, preserving some of the phrases and anecdotes that I sensed from the prior round had resonated the most. Finally, he set a timer for 30 seconds and had me do it one more time…and I almost instantly broke into tears.

With 30 seconds you don’t have time to plan, strategize, or even think. There is no room for narrative, logic, or reason. There isn’t even a beginning, middle, and end. It’s enough time to say one thing. One thing to leave an impression on your audience, to have them walk away different than how they walked in.

I wasn’t just repeating my talk; I was distilling it. Each round the energy and emotion I was trying to convey got condensed into a shorter, more compressed space. By the time we got down to 30 seconds, I was shocked to hear the following words erupt from my mouth like a long-dormant volcano:

“I am so tired of you fucking perfectionists!!!!!”

What I discovered in that moment was that there is a tremendous anger lying close to the heart of what I do. It’s anger at all the brilliant, unbelievably talented and creative people I interact with every day who are stuck endlessly organizing and optimizing their systems. To me, this is the greatest wasted resource on the planet – all the people who could contribute such amazing ideas and life-saving solutions to our world but can’t get out of their own way.

I initially got in touch with that anger in my first experience with anger work at a week-long course called Groundbreakers. Back then, it had come out messy, a new reservoir of energy being tapped for the first time. This time it was much cleaner, the rage flowing smoothly into a determination to do everything in my power to help people get over the fear and perfectionism stopping them from pursuing their creative dreams.

I don’t know if I will ever use this 30-second, anger-fueled, tearful style of speaking in the business world, but that wasn’t the point. The point was to remember that I have all the emotions flowing through me at all times, like a subterranean river, and that I can tap into any one of them whenever I need to. And that it is the emotion I am tapping into – in myself and therefore also in my listeners – that people will remember, not concepts.

Creating a Speaking HQ

After our three in-person sessions together and a couple Zoom calls to check in, I was ready to converge on all this experimentation and arrive at a final product. If you know me, you know I always try to arrive at a final product – a concrete artifact that distills the work I’ve done so that it lives on and remains accessible in the future.

The format of talks that Michael introduced me to was remarkably simple. It had only two elements – messages and stories – with each message having one or more stories to support and illustrate it. A short talk could constitute as little as one message with one story, or it could have multiple like this:

  • Message 1
    • Story
    • Story
  • Message 2
    • Story
    • Story
  • Message 3
    • Story
    • Story

What I like about this format is that it is simple enough to easily keep in your head, can be expanded or contracted as needed, and it’s always obvious what comes next. I created a new note with two headings, and in a single page summarized everything we had identified:

Note "BASB Speaking HQ"

I add “HQ” to the title of any note that I know will serve as an important hub for new projects in the future. This screenshot captures almost the entirety of its contents. I’ll add to it over time, but it already fills me with a tremendous sense of confidence knowing that I can hop in here and have a customized talk ready for any occasion in minutes, based on material I know like the back of my hand.

This is such a stark contrast to my previous process: spending many hours creating meticulously designed slides, avoiding outlining and practicing my talk until the last possible moment, realizing too late that I have too many slides and most aren’t necessary, and then rushing to fix it in a panic, leaving me in a stressed and anxious state of mind on the eve of my performance, while failing to practice more than once or twice.

I’m moving into a new season where my communication around BASB isn’t about conveying precise technical details. We now have multiple channels for that that are much more effective. 

My role is to give people an impression – to express a feeling or an experience of what life is like with such a powerful force at one’s disposal. To share how much it means to me, what it enables and allows in my life, and what might be possible for them if they were to embrace it as well.

I wrote this article to integrate my own learning, but also to offer that same opportunity to you: if anything I’ve shared resonated with you, and it’s something you want for yourself, the next cohort of Ultraspeaking is now open for enrollment. I’ve asked Michael to make a special offer to my followers: You’ll get $100 OFF with the code TIAGO100. This is the most accessible, social, playful approach I’ve ever encountered for learning how to express yourself authentically.

If you’re interested in hiring Michael Gendler or his co-founder Tristan de Montebello for 1-on-1 coaching as I did, you can also inquire by emailing [email protected].

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