
Former Tech Execs Amy Wilson and Meg Bear share the stories, insights and practical advice to navigate today's challenges.
We had so much fun doing Season 1 of The Meg & Amy Show. From our first moments wondering if our friendship would survive our different work styles... to filming with extraordinary leaders like Jill Popelka, Laszlo Bock, Yamini Rangan, Jen Morrow, John Wookey, and Dave Lu, who reminded us what's possible in leadership.
We learned the old CEO playbook is dead (thanks Gustavo Alba), that shipping containers explain AI transformation (Sangeet Paul Choudary), why NewCos have an unfair advantage over LegacyCos (Usman Sheikh), the pitfalls of blindspotting through incredible storytelling (Dr Kirstin Ferguson AM) and that Universal Basic Income has 100s of proof points showing it's not utopian—it's realistic (Scott Santens).
We formulated our AI transformation theses with Kieran Snyder, Kyle Poyar, Angela LE MATHON, and Seth Wylie. And, had a blast reiminiscing with Jason Averbook, John Sumser and Maksim Ovsyannikov!
What we learned along the way: We started this show wondering if our friendship could survive our wildly different work styles - and 500 text messages a day from Meg. Turns out, those differences made us better. We learned that building something together—imperfectly, publicly—is way more rewarding than waiting for perfect. And we learned that when you create space for real conversations, extraordinary people show up.
Here are my top 20 moments from Season 1. Watch them, share the ones that resonate, and tell us in the comments which moments hit home for you. [Full playlist here]
👉 Help us grow in 2026: If a clip resonates, drop a comment and share it. Your engagement helps us reach more leaders who need these conversations.
🧽 I catch Meg off guard when I call her a sponge (which is a compliment) in our very first episode! https://youtube.com/shorts/_0J52HfZIAE?si=WEvmayL_nzVdfWao
🥹 Laszlo Bock (Former CHRO, Google) dares us all to stand up to tyranny as leaders. https://youtube.com/shorts/IjP27hp6lRw?si=u_t1p9XWumA-jakb
🔥 Yamini Rangan (HubSpot CEO) doesn't ask "am I ready?" ... she imagines a future and then goes after it. https://youtube.com/shorts/89foMAAMGs4
💪🏼 Meg throws down the gauntlet and states that there's a new leadership prestige in town (and it's not how big your org is). https://youtube.com/shorts/iPXVcSgv9GU?si=PFQ2KlDI_87DDp6e
🥇 John Wookey (ERP Senior Executive) reminds us that first principles thinking is always the right way to go - even in AI hysteria. Gosh, I could listen to him all day! https://youtube.com/shorts/mJzP555lO-E?si=s9qROx5cjL4hRptw
🩸 Kyle Poyar (AI Pricing Guru) drops the brutal reality that those AI costs that were supposed to lower, just aren't. https://youtube.com/shorts/7u2oV6K56zs?si=Yl4Hy0upTBbbwW_z
💩 I get to share my "everyone's full of shit" wisdom! https://youtube.com/shorts/1Wan_VI5yjU?si=KWijCKQJ_hUASu0J
📈 Jen Morrow (President/COO of ExtensisHR)shares her greatest gift with us - the genius of creating a winning business case. https://youtube.com/shorts/szXplVaPcTY?si=UNzvhJKYYGpVYP4a
👶🏼 👧🏽 Scott Santens (UBI Expert) shares just how big an impact Universal Basic Income has on kids - like crazy good! https://youtube.com/shorts/Cm9M_urCPgA?si=u_GCglD8cNs5WVeF
🎤 Seth Wylie (AI Transformation "Mad Scientist") sings live on the show! https://youtube.com/shorts/v9xMZGNPdnU?si=uxUo3AQ1q5slHSiN
💻 Meg shares a life lesson that when people questioned (her) technical skills, it was about their insecurity, not her capability - giving us all a masterclass in changing the narrative in our heads. https://youtube.com/shorts/v2JSRmD50Sc?si=jHpOCZ4f2X1k0FfK
👨🏻💻 Maksim Ovsyannikov (SugarCRM CPO) predicts the future of product: outcomes and no UX! https://youtube.com/shorts/Z25lq7fuOBA?si=2qQd0P8ENkBdY6sf
💗 Jason Averbook (HR Tech Leader, Mercer) shares that though mindset and skillset are important, we must never forget heartset when it comes to making it happen. https://youtube.com/shorts/9zneWV4eMGg?si=cli_dA2_Qk8SRVMz
🙃 Meg makes fun of Amy's "diplomatic" style. https://youtube.com/shorts/e2UAxc0_bAs?si=0Jon0XE2BFpyUJ7w
🙊 Sangeet Paul Choudary (author of "Reshuffle") states his "true, but utterly useless" take on most AI fodder. https://youtube.com/shorts/H4tPYkHOvYk?si=Oywu0Dn_I5mxjOs-
🥸 I share my biggest secret: I was an undercover man! https://youtube.com/shorts/-3OSRd_Xegg?si=MPyCLIlRPUrCP2Lx
🌍 Usman Sheikh (High Output Ventures) lays out the stark contrast between LegacyCo's scaling with people and NewCo's scaling without. His theses helped to form so much of our understanding of the world and how to navigate it this past year. https://youtube.com/shorts/7uxJaXj9UXM
✅ Meg reminds us that you're probably doing something right if others are trying to sabotage you. https://youtube.com/shorts/mNErrD2p-yc
🤣 John Sumser jokes about the crazy FUD around AI - "best marketing ever" https://youtube.com/shorts/4yJLek5m8-E?si=FzEy_Ap-EPFZrOjs
🌺 Our very first guest, Jill Popelka, shows us all what it means to be human. every. damn. day. https://youtube.com/shorts/bGDWaqIk5k0?si=p0hJRHOx0d9v-Jco
What's next? Season 2 launches in March 2026. We're lining up even more incredible conversations about AI transformation, organizational design, investing in women and leadership in the age of ambiguity.
👉 Join us: Subscribe to the show, submit your Leadership Corner questions, and keep sharing the moments that matter. The more you engage, the more leaders we reach.
What was YOUR favorite moment from Season 1? Please do share - we would sure appreciate it!

