Leadership for Introverts: Building an AI Company When You Can't Sell Yourself

Leadership for Introverts: Building an AI Company When You Can't Sell Yourself

You can be brilliant at what you do and still feel like the kid no one picked — and starting a business doesn't always fix that. In this episode of Naked at the Top, Gabriele Sanguigno, founder of Tooth Fairy AI, shares what it takes to compete with the biggest names in tech as a self-described introvert who'd rather be coding than selling. He opens up about the cost of the dream — running a company on the other side of the planet from his family, the mask he puts on every time he speaks publicly, and why he stopped trying to be liked and started leaning on what he knows he's good at. You'll learn: - Why being good at the work and being good at the room are two different skills, and what to do when you only have one - How to hold your nerve and your vision when bigger players are working against you - Why chasing people who've already made up their minds about you is a losing game - The line between leaning on your strengths and forcing yourself to become someone else - What the 3am moments of clarity cost a founder, beneath the highlight reel - Why staying focused and bootstrapped can matter more than landing the big funding round By the end, you'll have a more honest picture of what it costs to back yourself when you're not the loudest person in the room — and permission to build your way instead of someone else's. Thanks to YourHR for sponsoring this episode. YourHR works with 100s of businesses to cut the jargon, simplify the systems, and build workplaces where people genuinely want to be.  Find out where your business stands with their free HR Health Check in minutes: 🔗 https://www.yourhrsystem.com/health-check/ 💼 https://www.linkedin.com/company/your-hr-team-and-system/ — Don't forget to like 👍, comment 💬, and subscribe (it's completely free!) 🔔 for more honest leadership stories. Click the bell to stay updated on new episodes. (00:00) Cold open (01:05) Welcome — meet Gabriele of ToothFairy AI (01:13) New Clothes: the last time he felt naked (01:28) A stroke, a continent away, during COVID (04:34) "I think Lara wanted to tell me to look after my wife" (05:26) Starting ToothFairy AI as everything was crumbling (06:00) When your co-founder stops believing in you (07:11) The vision: democratising AI, protecting privacy (09:15) "I'd never have started if I knew what it took" (09:35) Staying on course while competing with giants (11:57) Confidence vs. being the quiet guy in the corner (14:37) Mirror Mirror: a voice note from Dian, his CMO (16:05) "It's true, and it hurts" — not the founder caliber VCs want (17:40) Why a company competing with the giants gets no support (19:10) What victory looks like in five years (20:23) The upside of being misunderstood since childhood (22:50) "Better to be disliked for who you are" (24:17) Between the Lines (25:15) Q1 — Pizza or pasta, and the carbonara crime (26:54) Q2 — Military school at 14: the lesson and the one he'd erase (28:48) Six months "disassociated" — no one allowed to speak to him (31:44) Q3 — The mouthful of mud he's chewing right now (34:23) When the people meant to back you don't (35:48) Q4 — How much of the day is spent wearing the mask (38:20) Q5 — The thoughts he shuts down at 3am (40:53) The gamble, the sacrifice, and the family overseas (41:41) Where to find Gabriele + ToothFairy AI TOOTHFAIRYAI: https://toothfairyai.com/en https://www.linkedin.com/in/gabriele-sanguigno/ https://www.linkedin.com/company/toothfairy-ai/ STORIES FOR BUSINESS NEWSLETTER: https://storiesforbusiness.substack.com/ FOLLOW NAKED AT THE TOP Instagram: https://www.instagram.com/nakedatthetop/  LinkedIn: https://www.linkedin.com/company/naked-at-the-top/  Facebook: https://www.facebook.com/nakedatthetop/  🎥 YouTube – https://youtube.com/@NakedAtTheTop?sub_confirmation=1 [https://youtube.com/@NakedAtTheTop?sub_confirmation=1] 🍎 Apple Podcasts – https://podcasts.apple.com/gb/podcast/naked-at-the-top/id1822169203 [https://podcasts.apple.com/gb/podcast/naked-at-the-top/id1822169203]  🎧 Spotify – https://open.spotify.com/show/1lCQJthCpq39LkWXDlkwCf?si=9ef0f76a91cd4bd0 [https://open.spotify.com/show/1lCQJthCpq39LkWXDlkwCf?si=9ef0f76a91cd4bd0] CONNECT WITH ALEYX LinkedIn: https://www.linkedin.com/in/aleyxward  Instagram: https://www.instagram.com/aleyxfward/

How to actually make it safe for your team to fail — Authentic Leadership, Risk & the "Insurance Policy" Rule

Everyone tells you to "just be yourself" at the top — but nobody warns you how exposed that can leave you, or how lonely it gets being the one who's supposed to have the answers. In this episode of Naked at the Top, Leadernomics author, keynote speaker and 25-year Air Force veteran Seung Paik strips back the polished version of leadership and shares what it looks like behind closed doors. He makes the case that "authentic" might be the most dangerous word in leadership, opens up about the cost of looking unprepared, and walks through the "insurance policy" rule that makes it safe for your team to take risks — including the forty cleanup calls he made so one young officer would never know the mess she'd caused. You'll learn: - Why telling your team "it's safe to fail" means nothing until you've done the one thing that proves it - The "insurance policy" rule for empowering risk-averse people — and the forty cleanup calls behind it - Why "authentic" might be the most dangerous word in leadership, and the word Seung uses instead - The difference between authenticity and consistency — and why being your "honest self" in a bad mood isn't honesty - How sunk cost, ego and reputation trap leaders in decisions they know are wrong - The early warning sign of burnout that shows up in your attitude long before anything else - Why the most humble thing a high-achiever can do is build a small circle who'll tell them the truth - What goes through his head alone in a hotel room after a keynote — and why praise is harder to take than criticism By the end, you'll have a more honest picture of what leadership costs — and a few specific moves you can use the next time your team needs cover, or you catch your own ego making the call. Don't forget to like 👍, comment 💬, and subscribe (it's completely free!) 🔔 for more honest leadership stories. Click the bell to stay updated on new episodes. Follow Seung Paik: https://www.instagram.com/leadernomics/ https://www.leadernomics.org/ https://www.linkedin.com/in/seung-paik-leadernomics/ (00:00) Intro (00:45) Welcome Back — Our First Repeat Guest (01:00) New Clothes: The Last Time He Felt Naked (01:15) Flip-Flops at a Five-Star Wedding in Okinawa (06:07) "It Gets Worse" — Handed the Mic for a Speech (08:44) Why He Couldn't Shake It: What He Thought They Were Thinking (11:24) Mirror Mirror: A Voice Note from His Son, Micah (13:07) "Doing It the Right Way" — Hearing It Back (15:49) When the Right Way Means Cutting Corners: Leadership vs. Compliance (19:13) Risk, Reward, and Being Your Team's Insurance Policy (23:21) "Go Crazy" — The Lieutenant Who Blew Up His Inbox (28:40) Cleaning Up the Mess Without Killing the Courage (30:30) Between the Lines (31:06) The Leadership Word That Should Scare You ("Authentic") (36:22) The Excuse He Manufactures (and the Yard Work Behind It) (39:36) Talking Yourself Out of the Right Thing (40:31) Four Months on Book Tour: Sunk Cost, Pride, and Ego (45:30) Alone in the Hotel Room After the Keynote (50:30) Where to Find Leadernomics + Seung (52:11) How Did That Feel? -- Thanks to YourHR for sponsoring this episode. YourHR works with 100s of businesses to cut the jargon, simplify the systems, and build workplaces where people genuinely want to be.  Find out where your business stands with their free HR Health Check in minutes:  🔗 https://www.yourhrsystem.com/health-check/  💼 https://www.linkedin.com/company/your-hr-team-and-system/ STORIES FOR BUSINESS NEWSLETTER: https://storiesforbusiness.substack.com/ FOLLOW NAKED AT THE TOP Instagram: https://www.instagram.com/nakedatthetop/  LinkedIn: https://www.linkedin.com/company/naked-at-the-top/  Facebook: https://www.facebook.com/nakedatthetop/  🎥 YouTube – https://youtube.com/@NakedAtTheTop?sub_confirmation=1 [https://youtube.com/@NakedAtTheTop?sub_confirmation=1] 🍎 Apple Podcasts – https://podcasts.apple.com/gb/podcast/naked-at-the-top/id1822169203 [https://podcasts.apple.com/gb/podcast/naked-at-the-top/id1822169203]  🎧 Spotify – https://open.spotify.com/show/1lCQJthCpq39LkWXDlkwCf?si=9ef0f76a91cd4bd0 [https://open.spotify.com/show/1lCQJthCpq39LkWXDlkwCf?si=9ef0f76a91cd4bd0] CONNECT WITH ALEYX LinkedIn: https://www.linkedin.com/in/aleyxward  Instagram: https://www.instagram.com/aleyxfward/

What Working With Nike, Adidas and Global Agencies Taught Me | Christopher Asahara

Belonging, identity, power, and the courage to build something new. In this episode of Naked at the Top, Aleyx sits down with Christopher Asahara for a deeply honest conversation about growing up between cultures, being told you are not quite one of “us”, and learning how to turn difference into advantage rather than disadvantage. Christopher shares what it feels like to be an outsider in certain rooms, how global perspective reshapes the way you see leadership, and why narrow “America First” thinking often fails in a world built on connection, collaboration, and cultural intelligence. From community building and leadership during moments of social tension, to speaking up, taking risks, and trusting your own judgement, this episode explores what it really means to lead with both confidence and conscience. The conversation moves through entrepreneurship, imposter syndrome, redundancy, reinvention, and the responsibility that comes with influence. There are stories of starting again, building teams, protecting people, and staying calm when everything around you is moving fast. At its core, this episode is about identity, voice, and learning to stand comfortably in your own power — not by dominating, but by serving, listening, and building communities that last. STORIES FOR BUSINESS NEWSLETTER: https://storiesforbusiness.substack.com/ FOLLOW NAKED AT THE TOP Instagram: https://www.instagram.com/nakedatthetop/  LinkedIn: https://www.linkedin.com/company/naked-at-the-top/  Facebook: https://www.facebook.com/nakedatthetop/  🎥 YouTube – https://youtube.com/@NakedAtTheTop?sub_confirmation=1 [https://youtube.com/@NakedAtTheTop?sub_confirmation=1] 🍎 Apple Podcasts – https://podcasts.apple.com/gb/podcast/naked-at-the-top/id1822169203 [https://podcasts.apple.com/gb/podcast/naked-at-the-top/id1822169203]  🎧 Spotify – https://open.spotify.com/show/1lCQJthCpq39LkWXDlkwCf?si=9ef0f76a91cd4bd0 [https://open.spotify.com/show/1lCQJthCpq39LkWXDlkwCf?si=9ef0f76a91cd4bd0] CONNECT WITH ALEYX LinkedIn: https://www.linkedin.com/in/aleyxward  Instagram: https://www.instagram.com/aleyxfward/

Why Great Leaders Stop Asking “How” | Damien Gooden

sterclass in human-first leadership, honest business building, and why caring is not a soft skill — it’s a strategic advantage. Aleyx Ward sits down with Damien Gooden, CEO of HR Central, to unpack what it really takes to build a business where people stay, trust grows, and leadership doesn’t hide behind titles. From accidentally becoming a CEO to navigating COVID, firing customers, and building deep loyalty inside teams, Damien shares real stories from two decades in business. The conversation moves beyond textbook leadership and into the messy, human reality of running companies. Damien explains why subscription revenue nearly stalled growth, why referrals beat control, and why focusing on outcomes — not micromanagement — is the only way to scale without burning out. There are powerful reflections on parenting, culture, authenticity, and mental health, including phone-free dinners, getting teenagers to talk, and why men need spaces where it’s safe to open up. Damien also breaks down Radical Candour with real-world examples that every leader will recognise. If you’re building a business, leading a team, or trying to be a better human while doing both — this episode is for you. STORIES FOR BUSINESS NEWSLETTER: https://storiesforbusiness.substack.com/ FOLLOW NAKED AT THE TOP Instagram: https://www.instagram.com/nakedatthetop/  LinkedIn: https://www.linkedin.com/company/naked-at-the-top/  Facebook: https://www.facebook.com/nakedatthetop/  🎥 YouTube – https://youtube.com/@NakedAtTheTop?sub_confirmation=1 [https://youtube.com/@NakedAtTheTop?sub_confirmation=1] 🍎 Apple Podcasts – https://podcasts.apple.com/gb/podcast/naked-at-the-top/id1822169203 [https://podcasts.apple.com/gb/podcast/naked-at-the-top/id1822169203]  🎧 Spotify – https://open.spotify.com/show/1lCQJthCpq39LkWXDlkwCf?si=9ef0f76a91cd4bd0 [https://open.spotify.com/show/1lCQJthCpq39LkWXDlkwCf?si=9ef0f76a91cd4bd0] CONNECT WITH ALEYX LinkedIn: https://www.linkedin.com/in/aleyxward  Instagram: https://www.instagram.com/aleyxfward/

The Business of Comedy | Morry Morgan

What does it look like when an entrepreneur applies business discipline to comedy – and comedy thinking to business? In this episode of Naked at the Top, Morry Morgan shares the unconventional path that took him from an only-child upbringing and global travel, through China’s fast-moving business culture, and into building one of the most unexpected ventures in Australia: a comedy school and conference that shouldn’t exist – but does. This conversation is about preparation, courage, and following ideas all the way through. Morry unpacks how five minutes on stage became the turning point for an entirely new career direction, why breaking comedy’s rules unlocked commercial opportunity, and how creating something niche can actually grow the wider economy. We explore the reality of fast-speed living, the mental cost of always being “on”, and the resilience required when momentum disappears overnight. Morry speaks candidly about burnout, anxiety, fasting, and the mindset shift that turned a breakdown into a breakthrough. If you’ve ever wondered whether your strangest idea might actually be your most viable one – this episode will challenge how you think about preparation, energy, and commitment. This is a conversation for founders, creatives, and leaders who don’t fit neatly into one box – and don’t want to. STORIES FOR BUSINESS NEWSLETTER: https://storiesforbusiness.substack.com/ FOLLOW NAKED AT THE TOP Instagram: https://www.instagram.com/nakedatthetop/  LinkedIn: https://www.linkedin.com/company/naked-at-the-top/  Facebook: https://www.facebook.com/nakedatthetop/  🎥 YouTube – https://youtube.com/@NakedAtTheTop?sub_confirmation=1 [https://youtube.com/@NakedAtTheTop?sub_confirmation=1] 🍎 Apple Podcasts – https://podcasts.apple.com/gb/podcast/naked-at-the-top/id1822169203 [https://podcasts.apple.com/gb/podcast/naked-at-the-top/id1822169203]  🎧 Spotify – https://open.spotify.com/show/1lCQJthCpq39LkWXDlkwCf?si=9ef0f76a91cd4bd0 [https://open.spotify.com/show/1lCQJthCpq39LkWXDlkwCf?si=9ef0f76a91cd4bd0] CONNECT WITH ALEYX LinkedIn: https://www.linkedin.com/in/aleyxward  Instagram: https://www.instagram.com/aleyxfward/