Ambition 2.0

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

In this episode of Ambition 2.0, Amanda Goetz sits down with psychotherapist and Toxic Productivity author Israa Nasir to unpack why so many high-achieving women feel constantly behind, overwhelmed, and unable to rest—even when they’re doing “everything right.”

Israa explains how productivity often becomes a coping mechanism for shame, fear, and feeling “not good enough,” and why no system, planner, or habit hack can fix that. Together, they talk about the early warning signs of toxic productivity (including resentment and the phrase “I just need to get through next week”), how unhealed wounds show up at work through perfectionism and feedback sensitivity, and why rest isn’t a reward—it’s a requirement.

They also talk about how convenience culture and “main character energy” are quietly eroding community, why boundaries shouldn’t be rigid walls, and what it really takes to build a sustainable, values-aligned relationship with ambition.

In this episode, you’ll learn:



Why productivity is often emotional avoidance, not motivation



The earliest signs your productivity has turned toxic



How reparenting shows up in your career (feedback, perfectionism, taking up space)



The 7 types of rest (and no, scrolling doesn’t count)



Why convenience is costing us connection and how to build community again

00:00 Intro

04:17 When productivity becomes toxic

09:07 Reparenting at work

15:11 Boundaries 101

18:16 Hyper-optimizing “self-improvement”

26:21 Contentment vs complacency (and the “both/and” mindset)

28:06 The 7 types of rest

31:42 Convenience vs connection

38:28 Rapid-fire questions 

GUEST LINKS

IG: https://www.instagram.com/well.guide/ 

Subscribe to Well Guide: https://israanasir.substack.com/ 

https://www.israanasir.com/ 

Read Toxic Productivity: https://bookshop.org/a/116169/9781962305358 

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