CAREERYAP

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]

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]

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/]

Ep. 29 - How To Become a Great Manager (From Day One)

This one's for the managers! Whether you're a brand new manager, an aspiring one, or you have some years under your belt — this episode will help you become a great one! I'm sitting down with Lisa Lie — founder of Learna, a micro-learning app that teaches the people skills your job actually requires, and an organisational coach who has helped a lot of people navigate the jump from IC to manager. She breaks down how to know if management is right for you, what to actually do in your first 90 days, and how to give feedback without dreading the conversation for three days first. If you've ever been handed a manager title and thought "okay but now what" — this is exactly what you needed to hear earlier. WE COVER: * How to know if management is actually right for you * How to build manager skills before you even have the title * How to set up your first 90 days so nothing blows up * How to give feedback without feeling like a mean boss * How to manage someone more senior or experienced than you CHAPTERS: 1:06 – Intro + welcome 5:52 – Management is a career change, not a promotion 7:44 – How to know if management is right for you 12:35 – How to build manager skills before you have the title 19:58 – Your first 90 days: what to do and say 28:41 – How to give feedback in the moment 38:54 – Managing someone more senior than you 42:42 – Lisa's best advice MY LINKS: * Eline's LinkedIn: _https://www.linkedin.com/in/eline-de-wit/_ * MOXIE: _https://www.getmoxie.io_ * MOXIE IG: _https://www.instagram.com/getmoxie.io/_ * MOXIE TikTok: _https://www.tiktok.com/@getmoxie.io_ * EPISODE LINKS: * Learna (app + website): https://learna-app.com * Lisa on LinkedIn: https://www.linkedin.com/in/lisa-lie-42b705a1/ * Lisa on Instagram: https://www.instagram.com/lisa.lie_learna/ * Lisa on TikTok: https://www.tiktok.com/@lisa.lie_learna

Ep. 28 - Portfolio Careers: Why the Smartest People Are Ditching Traditional Jobs

Feeling like there's more in life than your current job but not ready to quit and leave it all behind? This is the episode for you! In this episode Anna uncovers portfolio careers — building multiple income streams without burning your life down to do it — and dives into exactly how to get started. Anna Mackenzie has built a portfolio career with five income streams from scratch — consulting, advisory, mentoring, digital products, and an accelerator — and has been documenting the whole journey publicly on Substack. You'll walk away with a clear first step, a framework for figuring out what you can actually monetize, and the exact moves Anna made to go from one fractional client to a full multi-income career. If you've ever felt too big for your job title — this episode will show you what's on the other side. WE COVER: * How to start building your portfolio career while still employed * How to figure out which of your skills people will actually pay for * Why a portfolio career is less risky than a single salary * How to build a network before you even have an offer * The "Shoot Your Shot Wednesday" ritual that wins real clients CHAPTERS: 1:06 – Intro + welcome 9:10 – What is a portfolio career, exactly? 16:28 – 3 pillars to start building now (while still employed) 25:32 – How to find your most marketable skills 37:20 – Anna's 5 income streams, broken down 55:02 – Shoot Your Shot Wednesday 59:05 – Anna'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 TT: https://www.tiktok.com/@getmoxie.io [https://www.tiktok.com/@getmoxie.io] EPISODE LINKS: * Anna's Substack: https://annamackstack.substack.com [https://annamackstack.substack.com] * Anna's website: https://www.annamackenzie.com.au [https://www.annamackenzie.com.au] * Anna on TikTok: https://www.tiktok.com/@annaclmack [https://www.tiktok.com/@annaclmack] * Anna on Instagram: https://www.instagram.com/annaclmack [https://www.instagram.com/annaclmack] * Anna on LinkedIn: https://www.linkedin.com/in/annaclmack/ [https://www.linkedin.com/in/annaclmack/] * The Brick (phone-locking device): https://getbrick.com [https://getbrick.com] * 📚 The One Thing — Gary Keller: https://www.amazon.com/ONE-Thing-Surprisingly-Extraordinary-Results/dp/1885167776 [https://www.amazon.com/ONE-Thing-Surprisingly-Extraordinary-Results/dp/1885167776]