When's the last time you actually looked at your bank account without cringing?  Amanda Goetz sits down with Haley Sacks (a.k.a. Mrs. Dow Jones), the internet's favorite financial expert, New York Times best-selling author of Future Rich Person: The New Rules for Building Wealth, and the woman behind the over two-million-strong community Mrs. Dow Jones. Haley built her entire brand on making money feel less shameful and way more accessible. And in this conversation, she gets into exactly how she did it (and how you can too). They cover why most of us were never actually taught how to manage money (spoiler: it's not your fault), why "deprivation" is the worst financial advice, the money beliefs we absorb before we even turn seven (!!), and why looking rich and being financially powerful are two very different games. Haley also gets real about her own money trauma, her parents' complicated relationship to wealth, and the "aha money moment" that changed everything for her. Key Takeaways: People can inherit money, but nobody inherits financial literacy, which means anyone can build it from zero. There's a floor to how much you can cut from your spending, but there's no ceiling to how much you can earn. Money dates are Haley's monthly ritual of sitting down with her finances—credit card statements, invoices, upcoming spending—and it's how she stays in control. Money is a relationship like any other—and you can't grow it if you avoid it. If you never actually sit down with your finances, don't expect it to get stronger. A “future rich person” has control over their time, their relationships, their choices, and their ability to leave situations that no longer serve them.Timestamps: [00:00] Intro [04:50] The origin story of Mrs. Dow Jones [06:09] The messages girls absorb about money growing up [08:08] Frictionless finance and doom-spending [11:09] Growing up with a "Wall Street father"  [15:23] Why women still feel embarrassed talking about money [18:25] Looking rich vs. being financially powerful [20:12] What is financial helplessness [22:21] Haley's monthly "money date" and the 50/30/20 rule she swears by [25:08] Why negotiating is the most underrated money move [28:14] Where women unknowingly give away their financial power  [30:13] What to do if you feel like you're behind financially  [31:45] Rapid fire questions [36:48] What "future rich person" really means to Haley GUEST LINKS Instagram: https://www.instagram.com/mrsdowjones/ TikTok: https://www.tiktok.com/@mrsdowjones Website: https://www.mrsdowjones.com/ Book: https://bookshop.org/a/116169/9798217090907  FOLLOW THE PODCAST IG: https://www.instagram.com/girlboss/  TikTok: https://www.tiktok.com/@girlboss  Amanda Goetz: https://www.instagram.com/theamandagoetz/  https://girlboss.com/pages/ambition-2-0-podcast  SIGN UP  Subscribe to the Girlboss Daily newsletter: https://newsletter.girlboss.com/   For all other Girlboss links: https://linkin.bio/girlboss/  ABOUT AMBITION 2.0  Powered by Girlboss, Ambition 2.0 is a podcast where we'll be exploring what it really means to "have it all" in work, family, identity, and self… and if it's actually worth it. Each week, you'll hear from hardworking women who've walked the tightrope of ambition. They'll share their costly mistakes, lessons learned, and practical tips for how to have it all and actually love what you have. Learn more about your ad choices. Visit megaphone.fm/adchoices

What if "having it all" didn't mean climbing a single corporate ladder but building a whole web of work that fits your real life? An ecosystem of offers, clients, and projects fueled by your network and reputation, where you can tap into different opportunities at different seasons of life. This week, host Amanda Goetz sits down with Anna Mackenzie, a startup advisor, writer, and author of the newsletter Anna Mack’s Stack, who traded the corporate dream for a self-designed portfolio career. They get into how to diversify your income, why articulating your value is harder (and more important) than selling it, and how to start building on the side without burning out or quitting your day job. From the sunk cost fallacy that keeps you stuck to the 30-minutes-a-day rule that changed Anna's life, this episode is your friendly reminder to stop forcing your career into a straight line. Key Takeaways: A portfolio career is multidimensional and diversified by design—many income streams, projects, and identities at once. A full-time job can absolutely be part of a portfolio. It's not all-or-nothing. Your salary can fund the experimentation. Start building on the side before you leap. Ask past bosses and colleagues what you're good at. You can't always see your set of skills or offers clearly. Break big scary goals into the smallest achievable unit of effort—what Amanda calls the “KitKat” method. Structure your portfolio career around three tiers: core, secondary, and experimental income. You don't need a perfect strategy. Experiment your way to a plan that fits your life. (00:00) Intro (02:16) How ambition changes over time (04:20) What a portfolio career actually is (06:42) Signs a portfolio career might be for you (08:55) What keeps people stuck (11:41) Why the traditional path feels narrow for women (13:42) The first step: knowing your value (16:04) Starting when you're too drained (20:04) Side hustle vs. portfolio career (21:18) Building your flywheel (24:30) Deliberate experimentation (29:16) Rapid fire GUEST LINKS Anna’s new 6-week accelerator, The Portfolio Career Build Method: https://www.annamackenzie.com.au/portfoliocareerbuildmethodSubstack: Anna Mack’s Stack  Website: https://www.annamackenzie.com.au/ Instagram: https://www.instagram.com/annaclmack/  TikTok: https://www.tiktok.com/@annaclmack  LinkedIn: https://www.linkedin.com/in/annaclmack/  FOLLOW THE PODCAST IG: https://www.instagram.com/girlboss/ | TikTok: https://www.tiktok.com/@girlboss  Amanda Goetz: https://www.instagram.com/theamandagoetz/  https://girlboss.com/pages/ambition-2-0-podcast  SIGN UP  Subscribe to the Girlboss Daily newsletter: https://newsletter.girlboss.com/   For all other Girlboss links: https://linkin.bio/girlboss/  ABOUT AMBITION 2.0  Powered by Girlboss, Ambition 2.0 is a podcast where we'll be exploring what it really means to "have it all" in work, family, identity, and self… and if it's actually worth it. Each week, you'll hear from hardworking women who've walked the tightrope of ambition. They'll share their costly mistakes, lessons learned, and practical tips for how to have it all and actually love what you have. Learn more about your ad choices. Visit megaphone.fm/adchoices

We’re told that we can have it all if we time it right: build your career first, then start a family. But what does the medicine actually say? Amanda Goetz sits down with Dr. Lucky Sekhon, a double board-certified reproductive endocrinologist at RMA of New York and author of the USA Today bestseller The Lucky Egg. Dr. Lucky busts the biggest fertility myths (no, your fertility doesn't fall off a cliff at 35), explains why so-called "fertility checks" are mostly marketing, and breaks down the real difference between freezing eggs and freezing embryos. She also flips the script on a part of the story we tend to ignore—male-factor infertility, which accounts for roughly half of cases—and why family building is a team sport. Women shouldn’t carry all the burden! It's an honest, science-forward, and surprisingly reassuring conversation about the fertility knowledge gap—and how it’s okay to not have it all figured out in your 20s. . This episode gets into both the emotional and physical considerations of fertility treatment, and we think it's a worthwhile listen, regardless of what stage of life you might find yourself in—and even if you're undecided on the whole kids thing. Key Takeaways: Fertility doesn't fall off a cliff at 35. It's a gradual continuum, and many women conceive naturally into their 30s and 40s. AMH measures egg count, not fertility, and a low number shouldn't cause panic. Most pop-in or at-home "fertility checks" are marketing. No single test can predict whether you'll struggle to conceive. Start paying attention in your 20s by understanding your cycle and spotting red flags like PCOS or endometriosis. And pay attention to your family history. Freezing eggs and freezing embryos are different—eggs offer more flexibility and stay solely yours, while embryos give clearer answers but need both partners' sign-off. When choosing a clinic, ask about its actual thaw and IVF success rates, not just whether you like the doctor. Male-factor infertility is something we need to talk more about. Every day stress doesn't cause infertility, but insulin resistance is an under-recognized and treatable driver worth checking. (01:20) Intro (03:30) Dr. Lucky's personal journey (08:49) The misinformation problem and why absolutes are a red flag (10:22) The "cliff at 35" myth and the continuum of fertility (11:03) When to start paying attention (hint: your 20s) + birth control myths (15:28) Amanda's PCOS diagnosis (18:31) Family timing, privilege, and perfectionism (21:46) Feeling "behind," the knowledge gap, and giving yourself grace (24:56) Egg freezing: when it should enter the conversation (27:14) All about eggs vs. embryos  (32:12) Men and male-factor infertility (36:00) Rapid fire (44:00) Inside The Lucky Egg GUEST LINKS Read The Lucky Egg https://www.instagram.com/lucky.sekhon/  https://theluckyegg.com/  FOLLOW THE PODCAST IG: https://www.instagram.com/girlboss/ | TikTok: https://www.tiktok.com/@girlboss  Amanda Goetz: https://www.instagram.com/theamandagoetz/  https://girlboss.com/pages/ambition-2-0-podcast  SIGN UP  Subscribe to the Girlboss Daily newsletter: https://newsletter.girlboss.com/  For all other Girlboss links: https://linkin.bio/girlboss/ ABOUT AMBITION 2.0  Powered by Girlboss, Ambition 2.0 is a podcast where we'll be exploring what it really means to "have it all" in work, family, identity, and self… and if it's actually worth it. Each week, you'll hear from hardworking women who've walked the tightrope of ambition. They'll share their costly mistakes, lessons learned, and practical tips for how to have it all and actually love what you have. Learn more about your ad choices. Visit megaphone.fm/adchoices

Most leadership advice was written by and for a generation that thought "work-life balance" meant leaving the office before 9 p.m. and checking emails on weekends. Amanda Litman is here to set the record straight. As co-founder of Run for Something—the organization that's helped elect over 1,600 young leaders across the U.S.—and author of When We're In Charge, Amanda has spent years studying what actually makes the next generation of leaders different. She sat down with Amanda Goetz to get into the stuff no one says out loud, like why "bring your full self to work" is actually setting you up to fail, why return-to-office mandates disproportionately push moms out of the workforce, and what it really means to lead with authenticity without accidentally trauma-dumping on your team. 🙃 Plus: the surprisingly effective thing she did every Saturday in 2025 to fight loneliness; the case for the four-day workweek; and a rapid-fire round of who’s most likely to: workplace edition (Gen Z, millennials, or Gen X). If you've ever wondered whether you can lead a team, build a career, and have a full life—without becoming the kind of boss you swore you'd never be—this one's for you. 01:17 Intro 02:37 The biggest lie in leadership 07:43 "Bring your full self to work" is setting you up to fail 10:15 The three-question framework for showing up authentically without oversharing 13:43 Personal branding for leaders who grew up online 17:11  How to use your platform without blowing up your career 19:32 Return to office, paid family leave, and why flexible work isn't a perk 25:40 The loneliness of leadership, and two solutions 32:28 The one thing first-time leaders need to let go of (hint: it's being liked) 33:18 Rapid fire who’s most likely to: Gen Z vs. millennial vs. Gen X KEY TAKEAWAYS Responsible authenticity is about bringing the best version of yourself to serve your team, not your unfiltered 3 a.m. thoughts. Your employees are not your friends. Friendship is a relationship between equals, and a boss-employee dynamic is not that.  If you can't manage a remote team, that's a “you” problem. The four-day workweek forces better prioritization, and the research backs it up. The sooner you let go of needing to be liked, the sooner you can actually lead—trying to please everyone is a fast track to pleasing no one and resenting yourself. GUEST LINKS IG: https://www.instagram.com/amandalitm/  Read When We're in Charge Learn more about Run for Something https://www.amandalitman.com/  FOLLOW THE PODCAST IG: https://www.instagram.com/girlboss/ | TikTok: https://www.tiktok.com/@girlboss  Amanda Goetz: https://www.instagram.com/theamandagoetz/  https://girlboss.com/pages/ambition-2-0-podcast  SIGN UP  Subscribe to the Girlboss Daily newsletter: https://newsletter.girlboss.com/  For all other Girlboss links: https://linkin.bio/girlboss/ ABOUT AMBITION 2.0  Powered by Girlboss, Ambition 2.0 is a podcast where we'll be exploring what it really means to "have it all" in work, family, identity, and self… and if it's actually worth it. Each week, you'll hear from hardworking women who've walked the tightrope of ambition. They'll share their costly mistakes, lessons learned, and practical tips for how to have it all and actually love what you have. Learn more about your ad choices. Visit megaphone.fm/adchoices

You've probably had one. Maybe you even have one right now. And if Glassdoor data is anything to go by, you're far from alone—mentions of "toxic boss" in workplace reviews have surged 6.7x since 2018. 🤯 This week, Amanda Goetz sits down with Mita Mallick—bestselling author, workplace culture expert, and self-described recovering people pleaser—to talk about the bad bosses we've all worked for, the ones we've quietly become, and how to tell the difference.  Mita's new book, The Devil Emails at Midnight, breaks down 13 archetypes of bad bosses (yes, they all have nicknames), and this conversation goes deep on the ones you'll recognize immediately—and the ones that are dangerously easy to miss. They get into why bad bosses are made, not born; what the midnight email really signals about a leader's psychology; and why toxic positivity might actually be the sneakiest trap for high-achieving women.  Over 70% of workers say they've quit a job because of a bad boss. This episode is for everyone who has—and everyone who's still figuring out whether they should. Key Takeaways Bad bosses are made, not born. The sneakiest toxic boss, The Cheerleader.  Demanding excellence and coaching excellence are not the same thing. Apologies are the most underutilized tool in leadership. Trauma from a bad boss follows you to the next job if you don't deal with it. Context matters. Not every bad boss is a reason to quit. Self-awareness is the non-negotiable foundation of good leadership.02:30 Intro 04:49 The 3 moments toxic leadership shows up  13:18 Why toxic positivity is the hardest boss to spot  17:25 What The Devil Emails at Midnight title really means  20:24 Why companies keep tolerating bad bosses  25:43 Mita was a micromanager too  29:08 Where to start if you have a toxic boss right now 31:14 How to survive without burning out when leaving isn't an option  33:05 The post-toxic-boss trauma nobody talks about  35:42 What the best bosses do differently  37:20 Rapid-fire questions GUEST LINKS IG: https://www.instagram.com/mita_mallick13/  LinkedIn: https://www.linkedin.com/in/mita-mallick/  Read The Devil Emails at Midnight: https://bookshop.org/a/116169/9781394316489  Read Reimagine Inclusion: https://bookshop.org/a/116169/9781394177097  FOLLOW THE PODCAST IG: https://www.instagram.com/girlboss/ | TikTok: https://www.tiktok.com/@girlboss  Amanda Goetz: https://www.instagram.com/theamandagoetz/  https://girlboss.com/pages/ambition-2-0-podcast  SIGN UP  Subscribe to the Girlboss Daily newsletter: https://newsletter.girlboss.com/  For all other Girlboss links: https://linkin.bio/girlboss/ ABOUT AMBITION 2.0  Powered by Girlboss, Ambition 2.0 is a podcast where we'll be exploring what it really means to "have it all" in work, family, identity, and self… and if it's actually worth it. Each week, you'll hear from hardworking women who've walked the tightrope of ambition. They'll share their costly mistakes, lessons learned, and practical tips for how to have it all and actually love what you have. Learn more about your ad choices. Visit megaphone.fm/adchoices

If you've ever wondered what actually gets discussed behind closed doors when companies are hiring, promoting, or handing out pink slips, this episode is like a backstage pass. Amanda Goetz sits down with Deepali Vyas, a veteran executive recruiter and career coach who’s spent 25 years in the boardrooms on Wall Street. She’s also one of the most followed career experts on the internet.  She's advised Fortune 500 CEOs, hedge funds, and private equity firms on their most senior hires—and she's here to spill everything they never told you. The timing couldn't be better. Between mass layoffs, rapid AI expansion, and an unpredictable job market, navigating your career right now feels harder than ever. Deepali breaks down exactly what's changed, what still works, and what you need to stop doing right now—from the resume mistakes that get you filtered out in six seconds (!!!), to why loyalty to a company is not the flex you think it is, to the 5-5-3 networking rule that actually moves the needle when you're on the market. We're also getting into the closed-door conversations that decide who gets laid off, the one move that makes hiring managers want you more, and the corporate truth that might sting a little: your manager is not your mentor. If you've been playing checkers with your career, this is your invitation to start playing chess. Tune into the episode to find out how. Key Takeaways Talent alone won't get you promoted—visibility will.  Your manager is not your mentor.  Everyone has skills. What separates people is proximity. BLUF: Bottom line up front. Build your external brand while you're still employed.  Why you should leave your job when you’re winning.  When you're job searching, use the 5-5-3 rule: five texts to people in your network, five days a week, and aim for three meetings. 00:00 Intro 03:12 Deepali's career origin story 05:41 Being underestimated as a superpower 06:13 Talent alone isn't enough: visibility & access matter most 08:14 Managing up & the power memo 13:58 Checkers vs. chess: playing the long game 15:57 Leave when you're winning 17:30 Behind closed doors: what hiring really looks like 20:06 Resumes, layoffs & career resilience 22:54 The 5-5-3 rule 26:46 Becoming indispensable vs. high impact 32:21 Rapid fire: resumes, LinkedIn & interview tips GUEST LINKS IG: https://www.instagram.com/the_elite_recruiter/ TikTok: https://www.tiktok.com/@elite.recruiter Subscribe to Deepali's newsletter: https://eliterecruiter-newsletter.beehiiv.com/ FOLLOW THE PODCAST IG: https://www.instagram.com/girlboss/ | TikTok: https://www.tiktok.com/@girlboss  Amanda Goetz: https://www.instagram.com/theamandagoetz/  https://girlboss.com/pages/ambition-2-0-podcast  SIGN UP  Subscribe to the Girlboss Daily newsletter: https://newsletter.girlboss.com/  For all other Girlboss links: https://linkin.bio/girlboss/ ABOUT AMBITION 2.0  Powered by Girlboss, Ambition 2.0 is a podcast where we'll be exploring what it really means to "have it all" in work, family, identity, and self… and if it's actually worth it. Each week, you'll hear from hardworking women who've walked the tightrope of ambition. They'll share their costly mistakes, lessons learned, and practical tips for how to have it all and actually love what you have. Learn more about your ad choices. Visit megaphone.fm/adchoices

Amanda Holden spent years working 13-hour days at a male-dominated finance firm—helping rich men get richer—before she made a bold exit. She saved aggressively, sold her car, and walked away without a plan. That scrappy chapter even earned her the cute nickname “Dumpster Doggy.” 🙃 But it also gave her something most people never get: the space to figure out what she actually wanted. The answer? Teaching women how to invest. In this episode of Ambition 2.0, Amanda Goetz sits down with Amanda Holden—financial educator, founder of Invested Development, and author of How to Be a Rich Old Lady—to unpack why investing still feels so overwhelming (even for smart, ambitious, high-earning women). Spoiler: it’s not you. The system was designed to gatekeep this information from women. Amanda breaks down the biggest lies women have been told about money, why the Roth vs. traditional debate is more distracting than helpful, and what a 401(k) actually is (hint: for our millennial listeners, think of it like Caboodles from the ‘90s). If you’ve ever looked at your retirement account and thought, “I should probably figure that out someday,” this episode is for you! In this episode: Why ambition isn't just about winning the man's game anymore How Amanda went from finance bro to financial feminist The Caboodles analogy that will change how you think about your retirement account Why the Roth vs. traditional debate is the wrong conversation What a fee-only financial planner actually does (and when you need one) The #1 first step if you feel behind on investing Why "go get your match" is the most important money advice for employees The trad wife economy and the financial risks women need to understand 00:00 Intro 03:59 What drew her to finance and what made her leave  09:29 The mindset shift that helped her walk away from her finance job 11:02 Her scrappy, "Dumpster Doggy" era (which allowed her to quit her 9-5)  13:10 The TL;DR on Invested Development, Amanda’s financial education platform  16:12 Why investing feels so hard, even for smart women  21:01 The biggest lies women have been told about investing  23:49 Roth vs. traditional: why it's the wrong debate  25:13 The Caboodles analogy that explains your 401(k) perfectly  29:28 The first step when you feel overwhelmed by money  30:39 Do you actually need a financial planner?  34:57 The beginner investing move that builds real confidence  40:05 What it actually means to be a rich old lady  43:00 Rapid fire: earning vs. investing, money myths, and more GUEST LINKS IG: https://www.instagram.com/dumpster.doggy/  Read How to Be a Rich Old Lady Check out the Invested Development course: https://amandaholden.podia.com/invested-development FOLLOW THE PODCAST IG: https://www.instagram.com/girlboss/ | TikTok: https://www.tiktok.com/@girlboss  Amanda Goetz: https://www.instagram.com/theamandagoetz/  https://girlboss.com/pages/ambition-2-0-podcast  SIGN UP Subscribe to the Girlboss Daily newsletter: https://newsletter.girlboss.com/ For all other Girlboss links: https://linkin.bio/girlboss/ ABOUT AMBITION 2.0 Powered by Girlboss, Ambition 2.0 is a podcast where we'll be exploring what it really means to "have it all" in work, family, identity, and self… and if it's actually worth it. Each week, you'll hear from hardworking women who've walked the tightrope of ambition. They'll share their costly mistakes, lessons learned, and practical tips for how to have it all and actually love what you have. Learn more about your ad choices. Visit megaphone.fm/adchoices

Dating in 2026 can feel… bleak. Everyone is analyzing “red flags,” burned out on dating apps, and building emotional walls to stay safe out there. Sound relatable? In this episode of Ambition 2.0, Amanda Goetz sits down with relationship expert Amy Chan—founder of Renew Breakup Bootcamp, bestselling author of Breakup Bootcamp, and author of the upcoming book Unsingle: How to Date Smarter and Create Love That Lasts—to talk about what’s actually going wrong in modern dating (especially for ambitious women) and how to date smarter. Amy breaks down why high-achieving women can accidentally bring “CEO energy” into their love lives—turning dating into a project, over-functioning, and doing 90% of the work. You’ll learn how to stop over-giving, create space so someone can show you who they are, and why it’s not your job to coach someone out of their insecurity.  Plus, Amy shares her “dating funnel” framework (lead generation → evaluation → commitment) and the underrated stage most people skip: the evaluation phase (a.k.a.: dates 3–20, where character is revealed). If you’re dating right now—or you want a smarter path to partnership—this episode is for you. You’ll learn:  Why modern dating feels broken—and how hyper-fixating on red flags is blocking connection How “CEO energy” can sabotage dating and what to do instead Why it’s not your job to fix or coach a partner out of insecurity What emotional wealth really means (and why it matters more than money) Amy’s “dating funnel” framework and why dates 3–20 are crucial How “ick culture” keeps people single How to reopen your heart if dating has made you guarded, burned out, or distrustful  00:00 Intro 03:22 Women’s standards are rising—and “survival coupling” is over 05:04 What is the “CEO energy” problem? 07:26 How to leave space and let them show who they are 10:12 Emotional wealth > financial flex: what men can do differently now 14:50 Amy’s dating funnel framework 21:08 The internet’s worst dating advice GUEST LINKS Instagram:  www.instagram.com/missamychan TikTok: https://www.tiktok.com/@missamychan Read Breakup Bootcamp: https://bookshop.org/a/116169/9780062914743  Pre-order Unsingle: https://bookshop.org/a/116169/9781419779848  www.renewbreakupbootcamp.com  www.missamychan.com www.hearthackersclub.com  FOLLOW THE PODCAST IG: https://www.instagram.com/girlboss/ | TikTok: https://www.tiktok.com/@girlboss  Amanda Goetz: https://www.instagram.com/theamandagoetz/  https://girlboss.com/pages/ambition-2-0-podcast  SIGN UP Subscribe to the Girlboss Daily newsletter: https://newsletter.girlboss.com/  For all other Girlboss links: https://linkin.bio/girlboss/  ABOUT AMBITION 2.0Powered by Girlboss, Ambition 2.0 is a podcast where we’ll be exploring what it really means to “have it all” in work, family, identity, and self… and if it’s actually worth it. Each week, you'll hear from hardworking women who’ve walked the tightrope of ambition. They'll share their costly mistakes, lessons learned, and practical tips for how to have it all and actually love what you have. Learn more about your ad choices. Visit megaphone.fm/adchoices

Repeat after us: You can love your job and still be a workaholic. In this episode of Ambition 2.0, Amanda Goetz sits down with Dr. Malissa Clark, a professor at the University of Georgia, Director of the Healthy Work Lab, and author of Never Not Working: Why the Always-On Culture Is Bad for Business—and How to Fix It, to break down what workaholism can look like in real life (spoiler: it’s not just about working long hours). They get into the sneaky “working light” tasks that we tell ourselves don’t count as work (like sending emails while watching TV or checking Slack between errands), how leaders accidentally create always-on teams, and so much more.  If you’ve ever felt guilty while resting, struggled to stop thinking about work, or worried that your ambition is turning into something unhealthy, this episode is worth a listen.  In this episode, you’ll learn:  00:00 Intro  01:33 What workaholism is (and the four components) 04:32 Early signs your work habits are becoming unhealthy 07:21 What to do if you think you might be a workaholic  11:23 How leaders unintentionally create “always-on” teams 13:26 How to bring boundaries up with your boss 20:46 Redesigning work culture 24:04 Surviving a 40-hour workweek without losing your life 32:56 Rapid fire: urgent emails, Slack, PTO, and commute baths GUEST LINKS Read Never Not Working: https://bookshop.org/a/116169/9781647825096  https://www.malissaclark.com/  FOLLOW THE PODCAST IG: https://www.instagram.com/girlboss/ | TikTok: https://www.tiktok.com/@girlboss  Amanda Goetz: https://www.instagram.com/theamandagoetz/  https://girlboss.com/pages/ambition-2-0-podcast  SIGN UP Subscribe to the Girlboss Daily newsletter: https://newsletter.girlboss.com/  For all other Girlboss links: https://linkin.bio/girlboss/  ABOUT AMBITION 2.0Powered by Girlboss, Ambition 2.0 is a podcast where we’ll be exploring what it really means to “have it all” in work, family, identity, and self… and if it’s actually worth it. Each week, you'll hear from hardworking women who’ve walked the tightrope of ambition. They'll share their costly mistakes, lessons learned, and practical tips for how to have it all and actually love what you have. Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode of Ambition 2.0, host Amanda Goetz sits down with Alexa von Tobel—the founder of LearnVest (where she raised $75M and successfully sold it to Northwestern Mutual) and current founder and managing partner of Inspired Capital—to unpack the resilient mindset that has shaped her successful career, from founder to venture-capital veteran.Alexa dropped out of Harvard Business School and poured her life savings into LearnVest, a multimillion-dollar business idea—despite warnings from nearly everyone around her that she was making a big mistake. She did it in the middle of the 2008 economic recession, no less. Alexa shares why her 90-year-old self (and the fear of regret) fuels her to take big risks, the qualities she looks for when investing in a founder, and practical tips for pitching your business to VCs for the first time. She also shares an unpopular truth: if you’re becoming an entrepreneur for the status or the “quick money,” it’s going to be a rough ride. There’s only one reason why you should start your own business: because you can’t do any other job. Key takeaways Regret is usually about the swings you didn’t take—not the mistakes you made. Raising capital gets easier when you combine mission + proof + obsessive category insight. Feedback is a competitive edge (and ego is the fastest way to lose it). Entrepreneurship shouldn’t be “cool”—it should be inevitable for the person doing it. Sustainable ambition comes from doing what you love + what you’re excellent at, then turning the intensity toward your whole life. 00:00 Intro 02:46 Reclaiming ambition as a positive force 04:11 The LearnVest origin story and dropping out during the economic downturn of 2008 07:53 Raising $75M and the difference between capital vs. “world-class” capital 15:24 What founders get wrong in pitches (and what great answers sound like) 24:20 Identity beyond titles, exits, and the founder doom spiral 33:54 Speed round: The one quality she looks for before investing in founders (and the one that’s a major red flag)  GUEST LINKS IG: https://www.instagram.com/alexavontobel/?hl=en  Listen to her podcast here: https://www.inspiredcapital.com/content/podcasts  Learn more about Inspired Capital: https://www.inspiredcapital.com  FOLLOW THE PODCAST IG: https://www.instagram.com/girlboss/ | TikTok: https://www.tiktok.com/@girlboss  Amanda Goetz: https://www.instagram.com/theamandagoetz/  https://girlboss.com/pages/ambition-2-0-podcast  SIGN UP Subscribe to the Girlboss Daily newsletter: https://newsletter.girlboss.com/  For all other Girlboss links: https://linkin.bio/girlboss/  ABOUT AMBITION 2.0Powered by Girlboss, Ambition 2.0 is a podcast where we’ll be exploring what it really means to “have it all” in work, family, identity, and self… and if it’s actually worth it. Each week, you'll hear from hardworking women who’ve walked the tightrope of ambition. They'll share their costly mistakes, lessons learned, and practical tips for how to have it all and actually love what you have. Learn more about your ad choices. Visit megaphone.fm/adchoices