One Year Later: Reflections on Pitch Like a Pro
It has been a year since I first taught the "Pitch Like a Pro" course at St. Mary’s. Between a heavy workload, a new baby daughter, and the holiday season, I never quite found the space to sit down and articulate the deep reflections from that experience—until now.
Here are my core takeaways from a year of deconstructing the art of the ask.
1. The "What Is It?" Red Pill
We use the word "pitch" constantly. We say, "I have a pitch for my startup," or "That was a great pitch," or "Let me help you with your pitch deck." But it’s a massive red pill when you realize no one actually knows what pitching is. We know it’s valuable, but we’re not actually sure what it is or how to do it.
When I asked that question to my friends—founders, investors, and business owners who are objectively elite at this—we collectively realized that this lack of definition is a systemic problem. I was grateful for their contribution as guest speakers so we could solve this mystery in real-time.
2. The High-Performance Preparation Paradox
I noticed that people who are truly great at pitching prepare relentlessly, but they almost never talk about it. Because it’s a technical skill often masked by "charisma," there is an ego-driven myth that it’s just a mystical talent you either have or you don't.
The truth is that while instincts matter, every professional I know with a "natural" style has spent years collecting information and building robust internal models. My friend Tito Bohrt, who runs a massive sales organization, has a literal master slide deck of models and frameworks because he had to teach new employees.
The biggest misconception is that you can just wing it one day and walk out with funding. My friend Margaret Coblentz, a seasoned founder, didn't assume her past success would carry her. When she prepared to raise a new fund, she spent four to six months in deep preparation. She did an independent study at Stanford to understand the LP mindset and even hired a pitch coach to tear her presentation down and rebuild it over and over again.
If you had a short moment to ask someone for millions of dollars, wouldn’t you do the same? Most people don’t…
3. The "Before and After" Reality
The biggest myth in this industry is that the pitch is just a 20-minute meeting with a pretty deck and a trophy story. In reality, the meeting is just a small part. The "pitch" is everything that happens before (the situational analysis, the framing of power dynamics, the pre-wiring) and everything that happens after (when the slides go away and you have to navigate the curveballs and interruptions).
4. Being Smart Can Hurt You: The Right-Brain/Left-Brain Paradox
A striking observation from the course: highly educated people are often the worst at pitching. Doctors, lawyers, and engineers pride themselves on analytical, "left-brain" logic, but the language of influence lives in the right brain—it's about emotion, narrative, and sensories.
When you try to "logic" someone into an emotional commitment, you hit a wall. The tragedy is that this isn't taught in school. Even at elite institutions like Wharton, Stanford, and Harvard, this paradox remains largely unaddressed.
5. Deconstructing the Subconscious System
Pitch Like a Pro was, as far as I can tell, the first college course focused specifically on high-stakes influence system, the stuff that works for $1 or billions. Building the curriculum forced me to articulate what I had been doing subconsciously for years. Articulating it into a system gave me a new level of awareness—it anchored my conversations and gave me a roadmap for how to improve my own performance while helping others do the same.
6. Where the Game is Won: Objection Handling
Most people chase the "perfect" pitch—the one where you say the magic words and everyone nods in silent agreement. That is a fantasy. Professionals know the objections are coming, so they spend the majority of their time preparing for them. Most pitches are actually won during what I've dubbed "the midgame".
We tend to ignore or "smooth over" objections because they feel like rejection. But an objection is actually a gift. It’s a sign of engagement and a roadmap for what the other person needs to hear to get to "yes." The pros don't avoid the fire; they lean into it.
7. The Truth Paradox: Why the Honest Struggle
It turns out the truth… actually has no convincing power.
It makes sense when you think about it. The truth is hard to accept, boring, and complex. Meanwhile, the fruits of high-level influence are often rewarded to the liars, the gaslighters, and the manipulators. So if you are smart, honest, and trying to do the right thing… do you actually have any hope?
This realization hit me hard and has been the subject of deep internal reflection at this midpoint of my career. How do good, honest people overcome this contradiction? It took a while, but I eventually cracked it towards the end of the course.