I make my living speaking. It’s a family business.

I remember the first time I noticed my mom was depressed, and that depression was a thing. The first time I registered that my mom’s friends Karsen and Charly were cool, whatever cool was. I also remember, at the age five, people acting differently around my father. They would gaze into his eyes, nodding and then laughing. Women would touch his arm, laughing, and men, when they saw him, would yell at “Tommy,” genuinely happy to see him. He was great with a turn of phrase, funny and clever (i.e., British). The cocktail of articulate, irreverent, and smart chased with a Scottish accent made my dad attractive to women and employers.

My mother explained it to me: “Your father is charming.” At gatherings, inevitably, a semicircle forms around my dad, and he tells jokes and shares his take on things ranging from space (if it never ends, everything has already happened) to management (the key is a good job description). This charm sustained, for a decade, an upper-middle-class lifestyle for him, my mom, and me as he roamed the western United States and Canada, maintaining, in 15-minute spurts, pseudo-friendships with the managers of the outdoor and garden departments at Sears and Lowe’s. In exchange for his company, my dad’s 200 friends would over-order bags of shit … as he was selling fertilizer from O.M. Scotts, an ITT company.

In his late fifties, after the marketplace made it clear a recently laid-off middle manager from ITT was no longer welcome in the Fortune 500, he began giving seminars, open to the public, at a local community college. Cheap fluorescent lighting made the room feel like an operating room in an East German hospital. There were six rows of eight folding chairs, an overhead slide projector, transparencies with smudges, and a table at the back with half-empty two‑liter bottles of Dr Pepper, Sprite, and Tab, and lemon squares my stepmom had baked. Around 15 people, most in their fifties and sixties, would attend. My dad would speak for 90 minutes, breaking halfway through so everyone could venture to the hall and have a cigarette. I attended a few times as a teen. At that age, I found everything involving my parents lame, but this felt especially sad … depressing even. In exchange for imparting his wisdom on other mostly unemployed smokers, my dad had to pay $10–20 for gas and treats. My dad reflects on these seminars as the happiest he’s ever been. He was where he was meant to be, in front of a group of people speaking and teaching.

Charm Skips a Generation

I did not inherit my father’s charm. In fact the opposite of charm — being offensive is something I’ve developed a knack for. Not a “speak truth to power” kind of offensive, but a tone-deaf, saying exactly the wrong thing at the exact wrong moment kind of offensive. I regularly say things and write emails that make good people feel bad, and I know it. No excuse. Because I’m successful, people often recast it as honesty, or even leadership. No, it’s just being an asshole. Working on it.

However, my father did pass the ability to hold a room of people, as long as it’s a windowless boardroom or conference hall on the 55th floor of a midtown building or in the basement of a hotel. While most people become increasingly uncomfortable as the group grows, I experience the inverse. One-on-one I’m an introvert, insecure even. But as the room grows … other skills kick in. In front of dozens, crisp insights find me. In front of hundreds, humor and warmth. And thousands, a rush of adrenaline and the confidence to reach beyond my grasp and be inspiring. I may be wrong, but my heart is in the right place. I can look each person in the eye and claim I believe what I’m saying to be true. I’m blessed with not having to sell anything, and have no mercy nor malice for the firms or people referenced in my 30–60‑minute diatribes. Most people who speak at conferences are there to sell something and, most importantly, not offend anybody, as they may be selling to them the next day.

Market Dynamics

A mentor, Todd Benson, taught me that market dynamics trump individual performance. The wind of our society’s obsession with big tech is at my back, running over my vocal chords. My domain expertise, big tech, is white‑hot, and the economy is strong. These skills, coupled with proprietary data that dozens of overeducated twentysomethings at L2 collect and distill into insight, and a world-class creative team that designs imagery and charts, shot on the screen behind me, all sing like Pavarotti.

As I write this, I’m in the back of a windowless conference hall at the InterContinental Boston about to address the 600 gold-circle brokers and managers from a large real estate management firm. I haven’t seen the presentation I’m about to deliver, but am fairly certain this will be the highest-rated session of the event, and the team that booked me will feel the $3K/minute fee for 30 minutes was a great value. Last month, we were offered five times the usual fee for me to speak the the annual meeting of an Australian telco. Problem is, something about the jetlag of crossing the date line triggers something in my amygdala, and I become moderately depressed. (Note: I say “moderately,” as I’ve been around severely depressed people and don’t pretend to know the suffering they endure.) I end up pacing, unable to sleep, on the 88th floor of some six‑star Asian hotel wondering what series of bad decisions led me there. The distance from home starts to seriously fuck with me. I begin imagining I’m in a different world, unable to get back to the world where my kids live, sequestered from the only people who love me (see above: depression). In sum, we declined the offer.


To hone their craft, comedians do stand-up at clubs. For me stand-up is class, where I hone the craft of speaking every Tuesday night for three hours in front of 170 kids — second-year MBAs. I’m much more focused, and put more effort into the class, than in front of any board or gathering of gold-circle commercial real estate brokers. I make much less, about $1K, per podium hour (note: this sounds like more than it is, as you spend several hours, for each podium hour, outside of class prepping or meeting with students). In addition, the amount of bullshit you endure to get to this platform — advanced degrees, department chairs — is substantial.

My market value, like all things, will fade. People will tire of my topics, and I won’t have access to the resources that make my stuff great, vs. just good. Or more likely, my creative juices will just stop flowing. Working with young, creative people and having access to the best and brightest thinkers in business is for me what heroin was to Ray Charles. Once it’s gone, no more hits.

Off the Rails

Over the last five years I’ve given about 400 talks, and around 2% of the time, it all comes off the rails. I become anxious, start sweating, and my voice starts to shake. I begin gulping for oxygen and feel as if I am going to throw up and pass out. My talk “The Four Horsemen,” at DLD15 in Munich, went viral (for an academic anyway) and set in motion a bunch of great things for L2 — a book deal, inbound inquiries, increased awareness of the firm. I now give the opening address each year at DLD. Three years ago, out of nowhere … an attack. I came close to passing out on stage, and had to lean over with my hands on my knees for 30 seconds. The folks at DLD, uber nice, wanted to take me to the hospital, as they were convinced I was having a cardiac event. Good stuff.

This week, I was set to appear on Fox to discuss Trump’s attacks on Amazon and received an email that the president’s recently appointed chief economic adviser, Larry Kudlow, would be interviewing me. I started to get anxious. I then noticed my outfit. For some reason I had put everything in my closet on my person, including a hoodie, and was wearing about 11 layers.

Fight‑or‑flight set in, and I began strategizing on how to head this feeling off at the pass. “I know, I’ll have a drink … it will calm my nerves.” I’m pretty sure this is what most clinicians call alcoholism. It wasn’t my fear of digressing into full‑blown substance abuse that stopped me from shotgunning one or two Lagunitas IPAs at the nearest deli, but the prospect of somebody seeing me downing beers at 9:45 in the morning in midtown. In short, I didn’t and was ok. I took beta‑blockers for a while, which appeared to cure it. However, I don’t want to become reliant on any substance to perform. Unless, of course, it’s Lunesta, caffeine, Cialis, Chipotle, or cannabis. Or as I refer to them, the five food groups. If I wasn’t an atheist, it would be reasonable to think it’s God reminding me I’m just not that cool. However, as an atheist I’m pretty sure these are panic attacks whose source I’ll figure out … never.

Two Things

My dad will only get on a plane for two things, and they aren’t to see his grandkids or spend time with friends. He will only get on a plane to see the Toronto Maple Leafs play, or watch his son teach. He sits in the back row of the classroom. At the beginning of class we ask any visitors to introduce themselves — we get half a dozen curious undergrads or applicants in almost every class. My dad waits until they’re done and then, really dialing up the accent, says:

“I’m Tom Galloway, Scott’s father.”

There’s a pause then sustained applause. I see my dad riveted on my every word and movement for the next three hours. I wonder if, at 87, he looks at me and feels disappointment he didn’t have the opportunities to reach his full potential as a speaker, or if he feels the reward of evolutionary progress, seeing himself, but version 1.1. Seeing my dad in class reminds me the difference between bribing people to listen to you with lemon squares, and being paid $2K/minute is not talent — my dad has more. The difference is being born in America, and the generosity of California taxpayers, who give the children of secretaries the chance to attend world-class universities. The mix of my dad’s talent and the confidence garnered from the abundant love of his second wife gave his son the skills and opportunity to stand in front of people, look each in the eyes, and say, “I believe this to be true.”

Life is so rich,

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