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Ep. 32 - From Cold Emails to $1 Billion: Building Big and Knowing When to Leave

39 min · 9 de jun de 2026
Portada del episodio Ep. 32 - From Cold Emails to $1 Billion: Building Big and Knowing When to Leave

Descripción

This week I got to sit down with the co-founder of Chief - a venture-backed, $1.1 billion valued community for women executives - and we're going deep. Lindsay shares what it was like to build this from scratch: from cold emailing strangers and hitting $1M in revenue before the company even launched, to the moment she realised it was time to step back and hand over the reins to someone with fresh energy. We talk honestly about achieving big things, burnout, and the career lessons she wishes someone had told her earlier. WE COVER: * How to stop doing a good job and start having real business impact * What community actually means (and why it's your biggest career tool) * The unglamorous reality of building a venture-backed startup * How to take feedback without losing yourself in the process * What to unlearn on your way to the top CHAPTERS: 1:06 – Intro + welcome 5:37 – What Chief is and why it needed to exist 12:44 – The founder story: from cold emails to $1M pre-launch 19:29 – Feedback is not a gift — it's a vitamin 23:13 – The real paths to being a founder (no glamour) 30:36 – Burnout and knowing when to step back 38:27 – Lindsay's best advice MY LINKS: Ellie's LinkedIn: https://www.linkedin.com/in/elliedewit/ [https://www.linkedin.com/in/elliedewit/⁠] Ellie's IG: https://www.instagram.com/elliedewit_/ [https://www.instagram.com/elliedewit_/ ] MOXIE: https://www.getmoxie.io [https://www.getmoxie.io] MOXIE IG: https://www.instagram.com/getmoxie.io/ [https://www.instagram.com/getmoxie.io/] MOXIE TikTok: https://www.tiktok.com/@getmoxie.io [https://www.tiktok.com/@getmoxie.io] EPISODE LINKS: Chief: https://chief.com [https://chief.com] Bullish (consumer VC + agency): https://www.bullish.co [https://www.bullish.co] Lindsay on LinkedIn: https://www.linkedin.com/in/lindsaykaplan/ [https://www.linkedin.com/in/lindsaykaplan/] 📚 The Likeability Trap - Alicia Menendez: https://www.amazon.com/Likeability-Trap-Break-Free-Worth/dp/0062838768 [https://www.amazon.com/Likeability-Trap-Break-Free-Worth/dp/0062838768]

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34 episodios

episode Ep. 34 - She's helping 400,000 people use AI as their executive assistant - here's how with Megan Lieu artwork

Ep. 34 - She's helping 400,000 people use AI as their executive assistant - here's how with Megan Lieu

If you're using AI but feel like you're barely scratching the surface - and everyone else seems to have it figured out - this episode is for you. Megan Lieu is a former data scientist turned content creator, top 1% LinkedIn creator in the US, and one of the most followed voices on AI and careers with 400,000+ tech professionals in her community. She's here to break down how to move from using AI as a chatbot to using it as a executive assistant, why your personal brand is the one thing AI will never replace, and the exact workflow she uses that acts as her chief of staff. If you've ever felt like AI is making everything easier for everyone except you - this episode is going to change that. WE COVER * Why feeling behind on AI is completely normal right now * How to move from “knowing” to “doing” with AI (the real unlock) * The AI workflow that acts as Megan’s chief of staff * How to use AI in your job search — and exactly where not to * Why personal brand is the competitive advantage AI can never touch * The weekly wins archive and how AI helps you track it * The best advice: follow the rules first so you know which ones to break CHAPTERS 1:06 – Intro + welcome 3:17 – You don’t have to do it alone 6:23 – You’re not as behind on AI as you think 9:22 – From knowing to doing: the real power of AI 13:16 – How LLMs actually work (explained simply) 16:47 – The AI features you’re not using (but should be) 21:06 – Connecting your apps: AI as your chief of staff 28:40 – How Megan built an app using vibe coding 34:33 – AI in your job search — what helps and what doesn’t 37:50 – Why personal brand is the one thing AI can never replace 40:20 – The weekly wins archive 43:00 – Mentor moments (not mentors) 47:32 – The best advice Megan’s ever received MY LINKS Ellie’s LinkedIn: https://www.linkedin.com/in/elliedewit/ [https://www.linkedin.com/in/elliedewit/] Ellie’s IG: https://www.instagram.com/elliedewit_/ [https://www.instagram.com/elliedewit_/] MOXIE: https://www.getmoxie.io [https://www.getmoxie.io] MOXIE IG: https://www.instagram.com/getmoxie.io/ [https://www.instagram.com/getmoxie.io/] MOXIE TikTok: https://www.tiktok.com/@getmoxie.io [https://www.tiktok.com/@getmoxie.io] EPISODE LINKS Megan on Instagram: https://www.instagram.com/meglovesdata/ [https://www.instagram.com/meglovesdata/] Megan on LinkedIn: https://www.linkedin.com/in/meganlieu [https://www.linkedin.com/in/meganlieu] Megan on YouTube: https://www.youtube.com/@meglovesdata [https://www.youtube.com/@meglovesdata] Megan’s website: https://portfolio.meganlieu.com/ [https://portfolio.meganlieu.com/] WE COVERCHAPTERSMY LINKSEPISODE LINKS

Ayer39 min
episode Ep. 33 - How To Quit Your 9-5 (Without Blowing Up Your Life) artwork

Ep. 33 - How To Quit Your 9-5 (Without Blowing Up Your Life)

If you know your job isn't it anymore - but every time someone asks "so what do you actually want to do?" your mind goes completely blank, this episode is for you. Maggie Blackburn is a portfolio career strategist who helps multi-passionate women redesign their careers from the inside out - and left her own decade-long tech career to prove it's possible. She walks you through the exact exercises to figure out what you actually want, how to rewire the money mindset keeping you stuck, and how to start experimenting on the side before you ever have to quit. If you've been ignoring that voice for a while now - this episode will help you finally do something about it. WE COVER: * How to figure out what you actually want (when you have no idea) * How to know if it's your job — or something much bigger * How to rewire a money mindset that's keeping you stuck * How to start building on the side without quitting first * How to deal with the fear of what people will think of you CHAPTERS: 1:06 – Intro + welcome 4:53 – Maggie's story: from corporate burnout to portfolio career 6:44 – "I know this isn't it" — what to do next 10:22 – Rewiring your money mindset 20:51 – What's really holding you back (it's deeper than you think) 25:02 – How to experiment without quitting your job 34:24 – Maggie's best advice MY LINKS: Eline's LinkedIn: https://www.linkedin.com/in/eline-de-wit/ [https://www.linkedin.com/in/eline-de-wit/] MOXIE: https://www.getmoxie.io [https://www.getmoxie.io] MOXIE IG: https://www.instagram.com/getmoxie.io/ [https://www.instagram.com/getmoxie.io/] MOXIE TikTok: https://www.tiktok.com/@getmoxie.io [https://www.tiktok.com/@getmoxie.io] EPISODE LINKS: Maggie's website: https://www.maggie-blackburn.com [https://www.maggie-blackburn.com] Maggie's newsletter (Feeling Free): https://maggieblackburn.beehiiv.com [https://maggieblackburn.beehiiv.com] Maggie on LinkedIn: https://www.linkedin.com/in/maggieblackburn/ [https://www.linkedin.com/in/maggieblackburn/] Maggie on Instagram: https://www.instagram.com/maggieblackburn/ [https://www.instagram.com/maggieblackburn/] To Be Magnetic (program + podcast): https://tobemagnetic.com [https://tobemagnetic.com] 📚 Designing Your Life — Bill Burnett & Dave Evans: https://www.amazon.com/Designing-Your-Life-Well-Lived-Joyful/dp/1101875321 [https://www.amazon.com/Designing-Your-Life-Well-Lived-Joyful/dp/1101875321] Kristin Neff — self-compassion research: https://self-compassion.org [https://self-compassion.org] Anna Mackenzie's Substack (portfolio careers): https://annamackstack.substack.com [https://annamackstack.substack.com]

16 de jun de 202636 min
episode Ep. 32 - From Cold Emails to $1 Billion: Building Big and Knowing When to Leave artwork

Ep. 32 - From Cold Emails to $1 Billion: Building Big and Knowing When to Leave

This week I got to sit down with the co-founder of Chief - a venture-backed, $1.1 billion valued community for women executives - and we're going deep. Lindsay shares what it was like to build this from scratch: from cold emailing strangers and hitting $1M in revenue before the company even launched, to the moment she realised it was time to step back and hand over the reins to someone with fresh energy. We talk honestly about achieving big things, burnout, and the career lessons she wishes someone had told her earlier. WE COVER: * How to stop doing a good job and start having real business impact * What community actually means (and why it's your biggest career tool) * The unglamorous reality of building a venture-backed startup * How to take feedback without losing yourself in the process * What to unlearn on your way to the top CHAPTERS: 1:06 – Intro + welcome 5:37 – What Chief is and why it needed to exist 12:44 – The founder story: from cold emails to $1M pre-launch 19:29 – Feedback is not a gift — it's a vitamin 23:13 – The real paths to being a founder (no glamour) 30:36 – Burnout and knowing when to step back 38:27 – Lindsay's best advice MY LINKS: Ellie's LinkedIn: https://www.linkedin.com/in/elliedewit/ [https://www.linkedin.com/in/elliedewit/⁠] Ellie's IG: https://www.instagram.com/elliedewit_/ [https://www.instagram.com/elliedewit_/ ] MOXIE: https://www.getmoxie.io [https://www.getmoxie.io] MOXIE IG: https://www.instagram.com/getmoxie.io/ [https://www.instagram.com/getmoxie.io/] MOXIE TikTok: https://www.tiktok.com/@getmoxie.io [https://www.tiktok.com/@getmoxie.io] EPISODE LINKS: Chief: https://chief.com [https://chief.com] Bullish (consumer VC + agency): https://www.bullish.co [https://www.bullish.co] Lindsay on LinkedIn: https://www.linkedin.com/in/lindsaykaplan/ [https://www.linkedin.com/in/lindsaykaplan/] 📚 The Likeability Trap - Alicia Menendez: https://www.amazon.com/Likeability-Trap-Break-Free-Worth/dp/0062838768 [https://www.amazon.com/Likeability-Trap-Break-Free-Worth/dp/0062838768]

9 de jun de 202639 min
episode Ep. 31 - She Taught 30,000 Women How To Use AI - Here's How To Get Start artwork

Ep. 31 - She Taught 30,000 Women How To Use AI - Here's How To Get Start

If TikTok makes you feel like AI is the easiest thing in the world - but every time you sit down to try it, the results are just not there - this episode is for you. Maggie Love is the founder of SheFi, the global community that has taught over 30,000 women how to take financial agency through crypto and, now, AI. She's here to break down exactly how to start using AI in a way that actually lands - from building context and connecting your tools, to automating your inbox, to vibe coding your first app with zero coding experience. If you've ever felt like everyone else has figured out AI and you're still stuck at the starting line - this episode is going to change that. WE COVER * How to give AI the context it needs to stop sounding like slop * What connectors are and why they turn AI from a chatbot into a real assistant * How Maggie automated her email inbox — 3 levels, no coding required * What vibe coding is and how to build your first app without writing a single line of code * Why talking to AI instead of typing is the unlock most people are sleeping on CHAPTERS 1:06 – Intro + welcome 1:44 – Ask for what you want — from your boss, your AI, everyone 3:53 – How SheFi started 13:36 – Why Maggie moved into AI 18:45 – Give AI context + connect your tools 29:10 – Email automation + vibe coding 55:11 – Best piece of advice: build your brand now MY LINKS * LinkedIn: https://www.linkedin.com/in/eline-de-wit/ [https://www.linkedin.com/in/eline-de-wit/] * MOXIE: https://www.getmoxie.io [https://www.getmoxie.io] * Instagram: https://www.instagram.com/getmoxie.io/ [https://www.instagram.com/getmoxie.io/] * TikTok: https://www.tiktok.com/@getmoxie.io [https://www.tiktok.com/@getmoxie.io] EPISODE LINKS * SheFi: https://shefi.org [https://shefi.org] * Maggie on LinkedIn: https://www.linkedin.com/in/maggielove07/ [https://www.linkedin.com/in/maggielove07/] * SheFi on Instagram: https://www.instagram.com/shefiorg/ [https://www.instagram.com/shefiorg/] * Maggie on Twitter/X: @MaggieLove_ * SheFi Newsletter: https://newsletter.shefi.org/ [https://newsletter.shefi.org/] * Whisper Flow: https://whisperflow.app [https://whisperflow.app]

2 de jun de 202650 min
episode Ep. 30 - Blow It All Up: Mallory Contois on Quitting, Reinventing, and Finding Your People artwork

Ep. 30 - Blow It All Up: Mallory Contois on Quitting, Reinventing, and Finding Your People

If your gut is telling you it might be time for a change - but you don't feel ready, or don't even know what to change yet - this episode is for you. Mallory Contois is a startup growth leader (Lovable, Maven, Mercury, Pinterest and more), founder of the Old Girls Club, and the writer behind Good Work - a Substack with tens of thousands of subscribers. She's here to talk about following forward momentum over plans, running tiny experiments to find what you're actually built for, why everything is sales, and the wildly calculated decision she made to blow up her entire life in 2019. If you've ever felt like you're doing everything right and still can't seem to get unstuck - this episode is going to flip that. WE COVER: * Why your plan might be holding your career back * How to run tiny experiments to find what you're actually built for * The "cool signal" - the moment that tells you where to go next * Why blowing it all up is the most calculated move you'll ever make * Why everything is sales - yes, even dating * How to find your fun at work (even when work is hard) * Why no one ahead of you will ever judge you for trying CHAPTERS: 1:06 – Intro + welcome 2:24 – Fuck the plan: following forward momentum instead 7:04 – Community as your career superpower 12:04 – How Mallory got senior so fast 16:27 – Blowing it all up: cancer, a called-off wedding, and starting over 22:02 – How you show up is who finds you 27:40 – Sharing online without becoming an influencer 34:51 – Everything is sales 37:46 – Find your fun: from 2% to 15% 39:10 – The best piece of advice Mallory's ever received MY LINKS: * El’s LinkedIn: https://www.linkedin.com/in/elliedewit [https://www.linkedin.com/in/elliedewit] * El’s IG: https://www.instagram.com/elliedewit_ [https://www.instagram.com/elliedewit_] * MOXIE: https://www.getmoxie.io [https://www.getmoxie.io] * MOXIE IG: https://www.instagram.com/getmoxie.io/ [https://www.instagram.com/getmoxie.io/] * MOXIE TikTok: https://www.tiktok.com/@getmoxie.io [https://www.tiktok.com/@getmoxie.io] EPISODE LINKS: * Mallory's website: https://www.mallorycontois.com/ [https://www.mallorycontois.com/] * Good Work Substack: https://www.readgoodwork.com [https://www.readgoodwork.com] * Old Girls Club: https://www.jointheogc.com [https://www.jointheogc.com] * Mallory on LinkedIn: https://www.linkedin.com/in/mallorycontois [https://www.linkedin.com/in/mallorycontois] * Mallory on Instagram: https://www.instagram.com/mallorycontois/ [https://www.instagram.com/mallorycontois/]

26 de may de 202635 min