Why entrepreneurial teams are the fastest path to personal growth
Shannon Waller has a degree with a title so long she admits it took three years just to get through it, a Bachelor of Arts in Administrative and Commercial Studies with a specialization in Social Organization and Human Relations. Translation: how do people work together? She's been answering that question ever since, and her answer keeps coming back to the same place. "The best place to learn and grow is a company, especially an entrepreneurial company." Unlike academia or corporate hierarchies, entrepreneurial companies give you immediate feedback. You find out on the 15th and 30th of every month whether what you did created value. That feedback loop, Shannon argues, is what makes entrepreneurial teamwork the fast track for both professional and personal development.
What real leadership looks like in a networked economy
The old model of leadership, I say, you do, worked on assembly lines. It doesn't work now. Shannon is direct about it: "If you cannot care deeply about the people with whom you work, you would not be welcome in my company." She and Dan Sullivan are co-authoring a book called Growing Great Leadership, and the core argument is that leadership in the networked economy requires genuine relationship skills. That means being invested in someone else's success, not just their output. Shannon has worked with Kathy and Jodet at Strategic Coach for 23 and 25 years respectively. "I love them," she says, without any hesitation. That's not a soft statement, it's a strategic one.
Curiosity as a survival mechanism for entrepreneurial companies
Shannon came back from Abundance 360, Peter Diamandis's exponential technology conference, the night before this conversation. She was struck by how the smartest people in the room were also the most intensely curious, about material science, AI, digital currencies, everything. Her take: curiosity and intelligence travel together. But she's also clear that curiosity isn't a personality trait reserved for a few, it's a natural human state that gets covered up. Exhaustion covers it. Fear covers it. Boredom covers it. The leader's job isn't to install curiosity in people; it's to stop suppressing it. And the framework for that is simpler than most expect: stay open to new ideas. If you shut down what your team brings, they stop bringing it.
Trust, love, and the non-obvious ingredients of high-performing teams
Ben asked Shannon for the non-obvious umami ingredients of a great team, the ones that are in the recipe but easy to miss. Her first two answers: love and trust. She traces the love piece back to motivation science. Kolbe's framework breaks the mind into three parts: cognitive (IQ), affective (motivation, preference, heart), and conative (instinct, will, action). "Everything starts with motivation. You are not motivated to learn something if you don't care about it." Motivation lives in the heart. That's where love comes from. Combine someone who's technically skilled with someone who's technically skilled and loves what they do, and the second person wins every time. On trust, Shannon shares her personal rule: "I trust people to the degree that I think they know themselves." She tests for this by asking questions and watching whether people reflect on their experience, whether they seem curious rather than judgmental, and whether they're willing to put language to their own uniqueness through profiles and self-assessment tools.
The Gap and the Gain: how to anchor your team in progress
One of the most practical frameworks in this conversation is the Gap and the Gain, which Shannon traces back to a moment she witnessed firsthand. Dan Sullivan was talking to a client who'd just had his best quarter ever, biggest client, biggest contract, and the client came in saying things were terrible. Dan drew a line on a flip chart. Here's where you are. Here's your ideal. The gap between them is permanent, like a horizon that moves as you run toward it. Measuring yourself against the ideal always leaves you short. But if you turn around and measure from where you started, you see your actual progress. That's the gain. Shannon used this framework the day before this episode recorded, coaching a team showing signs of burnout. She had them map their momentum, their motivation, their multiplier projects, then anchor in their Clifton Strengths. "One person said, 'I now know myself better.' That was her win." The result: shoulders dropped, energy returned, and people started talking about what they were capable of instead of what they were failing at.
Investing in your team as the highest-return leadership decision
Ben is direct about his own experience: "The number one asymmetrical return that I've ever had has been investing into my team, hands down." He flew his whole team to Toronto multiple times. He ran them through Working Genius, Kolbe, Clifton Strengths. He asked them how they'd improve processes, what their vision was, what they needed. Shannon's observation from the outside: the message that sends is enormous. People who feel seen, heard, and understood don't just stay, they bring their whole brain to work. And the ones who aren't the right fit often opt out on their own. You don't have to do the heavy lifting. The investment itself does the sorting.
