Olivia: Alright Jackson, I'm going to say the title of a business book, and you give me your brutally honest, one-sentence roast. Ready? From Start-Up to Grown-Up. Jackson: Sounds like a parenting guide for people whose baby is a company with a questionable burn rate. Olivia: That is... surprisingly accurate. And it perfectly sets the stage for the book we're diving into today: From Start-Up to Grown-Up: Grow Your Leadership to Grow Your Business by Alisa Cohn. Jackson: I’m sensing this isn’t your typical business-school-jargon kind of book. Olivia: Not at all. Alisa Cohn is one of the most sought-after executive coaches in the world. We're talking about the person who has been in the trenches with the founders of companies like Venmo, Etsy, and DraftKings as they were scaling. She's been named the Top Startup Coach in the World for a reason. Jackson: Okay, so she's seen it all. The good, the bad, and the ugly of startup life. Olivia: Exactly. And what makes her perspective so unique is her background. She's a former startup CFO and, get this, an amateur rap artist. Jackson: Wait, a CFO who raps? Now I'm listening. That’s a combination of skills you don't see every day. It suggests she's not afraid to be a little unconventional. Olivia: And that's the perfect word for her core argument. She starts the book with a very provocative statement, one that a founder she was coaching said to her in a moment of pure exasperation. He said, "Leadership is an unnatural act." Jackson: Huh. I like that. It’s not something you hear in a motivational poster. It feels real. It feels like something someone would say after a very, very long Tuesday.

Olivia: It’s so real. Because what he meant was that the things you have to do as a leader—have difficult conversations, make unpopular decisions, constantly manage your own emotions—they go against our basic human instincts for comfort and harmony. Jackson: Right, nobody wakes up excited to give critical feedback or fire someone. That’s the stuff you procrastinate on. Olivia: Precisely. And Cohn argues that the first and most difficult part of this "unnatural act" is realizing the sheer weight of your own words. She tells this incredible story about a founder named Anna. Jackson: Okay, let's hear it. Olivia: Anna runs an agriculture supply company. One year, they have their Christmas party at a venue near the office. Afterwards, she's chatting with her team and makes a joke. She says, "The only way for that to be more convenient is to hold it in our parking lot!" Everyone laughs, it's a funny, off-the-cuff remark. Jackson: A classic throwaway line. I've probably made a dozen of those today. Olivia: Exactly. Except a year goes by. The next holiday season is approaching, and Anna's assistant comes to her with a serious question: "For the Christmas party in the parking lot, did you want us to rent a tent?" Jackson: You're kidding. A whole year later? They took a joke as a direct command? Olivia: They did. Because Anna was the CEO. And this is what Cohn calls the "CEO Megaphone Effect." Every word a founder says, whether it's a joke, a musing, or a complaint, is heard by the team as if it's being blasted through a megaphone. It's perceived as a directive, an order, a statement of company policy. Jackson: Wow. That’s actually terrifying. It means you can never just… think out loud. Your brain's rough drafts become someone else's finished blueprint. Olivia: That's the unnatural part. You have to constantly self-censor and manage your impact. There's another great story about a CEO named Tony, who runs a factory robotics company. He's brilliant, passionate, and full of energy. Jackson: I'm sensing a "but" coming. Olivia: A big one. In executive meetings, someone on his team, say the COO, would flag a potential risk. Tony, agreeing with her and wanting to solve it, would jump in with a fifteen-minute, high-energy monologue detailing exactly how they were going to tackle it. He thought he was being helpful and decisive. Jackson: And what actually happened? Olivia: Complete silence. The meeting would just die. He had sucked all the air out of the room. By providing the entire solution, he had unintentionally communicated, "Your input is no longer needed. I've got this." He took ownership away from his team, even though he was trying to support them. Jackson: Okay, but isn't this just about learning to be a better communicator? Why frame it as 'unnatural'? It feels like a skill you can learn. Olivia: It is a skill, but it's unnatural because it requires you to fight your own instincts. Tony's instinct was to jump in and solve the problem. Anna's instinct was to make a casual joke. A leader has to learn to pause, to ask questions instead of giving answers, to consider the megaphone effect before they speak. It’s a constant, conscious override of your normal, spontaneous human behavior. And that, for most people, feels deeply unnatural.

Jackson: That makes sense. So if managing your own words is that hard, I can't imagine what happens when you have to manage someone who has just as much power as you do. I'm thinking about cofounders. Olivia: You've hit on the next level of this unnatural journey. Cohn is very clear about this: she says the cofounder relationship is a marriage. It has all the same intensity, intimacy, and potential for toxicity. Jackson: And probably a much higher chance of a messy divorce that takes the whole company down with it. Olivia: Absolutely. She tells this story about two cofounders, Sherry and Jennifer. Sherry, the CEO, comes to Alisa for coaching, and when asked about her cofounder, the floodgates just open. For ten straight minutes, Sherry lists every single one of Jennifer's perceived flaws: she’s lazy, she plays favorites, she’s not intellectually curious, she’s taking credit for work she didn’t do. Jackson: Oh, that sounds awful. It's a bad divorce, but you're forced to see them at the office every single day. The resentment must have been poisoning everything. Olivia: It was. The cancer that eats away at these relationships isn't the conflict itself; it's the unresolved conflict. The little things that are left to fester. And that's why Cohn advocates for what she calls a "cofounder prenup." Jackson: A prenup for a business? What does that even look like? Olivia: It's a series of brutally honest conversations you have at the very beginning. You don't just talk about equity splits. You talk about your values. Your real goals—are you trying to build a billion-dollar empire or a lifestyle business? How will you make decisions when you disagree? What happens if one of you stops scaling with the company? You put all the ugliest possibilities on the table before they become reality. Jackson: So you have the hard conversation when you still like each other, not when you're ready to throw chairs. Olivia: Exactly. Because if you can't navigate that, you'll never survive the other high-stakes relationship: the board of directors. These are your bosses, the people who can fire you from the company you created. Jackson: The dragon's den. Olivia: A perfect description. And the book has this incredible, cinematic story about a CEO named Charlie. His company is missing its financial targets, and a powerful board member, Jesse, is on the warpath. Jesse tells Charlie to his face: "You need to be replaced. If you're still CEO, I'm pulling my firm's investment and resigning from the board." Jackson: That's a kill shot. Game over, right? Olivia: It felt like it. Charlie was panicked. But after coaching, he did something completely counter-intuitive. He realized Jesse didn't have the sole power to fire him; he had support from other board members. So he flew out to meet Jesse in person. Jackson: To fight it out? Olivia: The opposite. He walked in, led with vulnerability, and said, essentially, "You're right. I'm in over my head. I've never run a company this size before. I need help. Will you personally mentor me?" Jackson: No way. He asked the guy who was trying to fire him to be his mentor? That takes guts. What did Jesse say? Olivia: He was so taken aback, he just… agreed. And over the next six months, he actually did it. He became Charlie's ally. When the company was eventually sold, Jesse was the one in Charlie's corner, helping him negotiate the best possible terms. Jackson: Wow. So in both of these impossible situations—the toxic cofounder and the hostile board member—the answer wasn't to fight harder or 'win.' It was to get vulnerable and manage the relationship itself. It's another one of those unnatural acts.

Olivia: That is the entire journey in a nutshell. The path from "Start-Up to Grown-Up" isn't really about learning finance or marketing. The book makes it clear that those are table stakes. The real growth is in mastering the messy, uncomfortable, and deeply human psychology of leadership. Jackson: It starts with you. With realizing your words have the weight of a megaphone and that your internal state—your stress, your passion, your fear—is contagious. Olivia: And then it graduates to navigating these incredibly complex relationships where you can't just give orders. You have to influence, persuade, and sometimes, like Charlie, completely disarm your opponent by asking for their help. It’s a journey from control to influence. Jackson: And it's a journey that takes a huge personal toll. It’s no wonder the book points out that founders are about 30% more likely to experience depression than the general population. The pressure is immense. Olivia: It is. And acknowledging that pressure, acknowledging that it feels unnatural, is the first step to actually getting good at it. It's about giving yourself permission to be a beginner at leadership, even if you're an expert at everything else. Jackson: That’s a powerful thought to end on. It makes me think... for anyone listening who's in a leadership role, big or small, what's one casual comment you made this week that might have been heard through that 'CEO Megaphone'? What joke might have been interpreted as a command? Olivia: That's a great question for reflection. We'd actually love to hear your stories. If you've ever had a "CEO Megaphone" moment or a cofounder story that resonates, find us on our social channels and share it. The more we talk about the real, human side of this journey, the less unnatural it might start to feel. Jackson: This is Aibrary, signing off.