What if everything you've been told about sustainable fashion is actually impossible? Dr. Christina Dean, who's been fighting this battle for 20 years, doesn't sugarcoat the truth: fashion and sustainability are fundamentally at odds, yet she's built two organizations dedicated to proving change is possible. 

**Ready to love your Mondays? Buy 'Work That's Worth It' now - Amazon, B&N, Bookshop.org. OR, need more convincing? Get the first chapters FREE here.** 

In this raw conversation, Christina shares the brutal financial reality of building a social enterprise (spoiler: she couldn't pay her kids' school fees from this work), why she thinks starting your own nonprofit is usually a mistake. Plus, her strategy for real change: getting into the boardrooms of the 20 fashion giants that control 97% of the industry. 

If you've ever wondered whether sustainable fashion is just marketing hype or want to understand what it really takes to create systemic change in a $2 trillion industry, this episode will give you the unvarnished truth from someone who's been in the trenches for two decades.

Key points:

• The global fashion industry is dominated by just 20 fashion brands and groups that control 97% of total revenue, while hundreds of thousands of SMEs share the remaining 3%.
• Fashion and sustainability are fundamentally at odds - fashion encourages buying more while sustainability requires consuming less.
• Consumer behavior research is misleading - people say they care about sustainability but don't act on it when purchasing, even after major disasters like Rana Plaza.
• Christina's Art Collective specializes in recycling complex luxury materials with distinctive prints, logos, and IP that carry high brand reputational risk.
• Building sustainable change requires significant financial cushioning - Christina couldn't pay her children's school fees from her sustainability work alone after 20 years.
• The best advice is often NOT to start your own organization - some of the greatest change makers work unnamed inside the biggest, "dirtiest" companies.
• Luxury brands are ideal partners because they have the most to lose from reputation damage and can absorb recycling costs relative to their brand value.
• Real systemic change requires reaching the highest levels - getting all CEOs of the top 20 fashion companies "in a room" to solve problems collectively.
• Christina's next goal is influencing policy through industry associations and eventually joining fashion company boards.
• The complexity of the fashion sustainability problem has kept Christina engaged and fascinated for 20 years - her father advised choosing something "so monumentally huge you'll never get there."

Resources:

• The R Collective

What if everything you've been told about following your passion is actually holding you back from finding truly meaningful work? Jeremy Schifeling from Khan Academy completely flips the script on career advice, revealing why he hires people based on what they can DO, not what they're passionate about—and why starting with passion is just like chasing a big salary.

**Ready to love your Mondays? Buy 'Work That's Worth It' now - Amazon, B&N, Bookshop.org. OR, need more convincing? Get the first chapters FREE here.**

In this eye-opening conversation, he shares his journey from being a "thoroughly mediocre" kindergarten teacher in Brooklyn to becoming a marketing leader helping millions access free education, proving that your biggest career pivots often come from unexpected layoffs and trial-and-error discovery.

Jeremy's contrarian take on mentorship, his "portfolio career" philosophy, and his brutal honesty about figuring out your strengths will challenge everything you think you know about building a meaningful career.

If you've ever felt stuck trying to force yourself into the "right" path or wondered how to actually discover what you're good at, this episode will give you permission to experiment your way to work that's worth it.

What happens when a CEO who helped build Old Navy from a startup into an $8 billion company decides to flip venture capital on its head? Dawn Dobras reveals the shocking truth: 93% of venture capital goes to men, and she's built a fund that's 70% female investors to change that.

**Ready to love your Mondays? Buy 'Work That's Worth It' now - Amazon, B&N, Bookshop.org. OR, need more convincing? Get the first chapters FREE here.**

In this episode, Dawn Dobras exposes why most startup founders get ghosted by VCs (hint: it's not your pitch deck), shares the brutal math behind venture funding (1,000 deals reviewed, only 1-3 funded), and reveals exactly what she looks for beyond the typical metrics.

Plus, she drops game-changing advice on how students are breaking into VC right now without connections or trust funds - including the "shadow portfolio" strategy that's getting MBAs hired.

If you're interested in VC, micro-investing as an Angel investor, or working at a women-led start-up -- this is your episode as Dawn will give you the inside scoop.


Key points:

• Dawn spent 30 years as an operator running companies, including transforming Old Navy from a startup with less than $1M in sales to an $8 billion company, before transitioning to venture capital.
• Only 7% of venture capital check writers are male, with less than 3% of funding going to all-female founding teams and only 2% of healthcare funding directed toward women's health.
• Women invest in venture capital at half the rate of men, largely due to structural barriers including high minimum investments ($500K-$2M) and lack of access to information about the asset class.
• Capital F Fund has over 70% female investors, which is virtually unheard of in venture capital and creates a powerful mentorship network for portfolio companies.
• The fund focuses on three areas where technology shapes women's lives: women's health, digital commerce, and AI enablement, specifically targeting companies with valuations under $12 million.
• Dawn emphasizes that venture funding is extremely selective - they review about 1,000 deals annually and invest in only 1-3, meaning rejection doesn't reflect on the business quality.
• Key investment criteria include emotional resilience and ability to take feedback, as startups face constant challenges and founders must remain open to new ideas and counsel.
• Archive Resale, a portfolio company enabling brands to host resale on their websites, exemplifies the "triple threat" of female founder, climate impact, and tech growth potential.
• Women's health investments include Hey Jane (telehealth abortion care), Stardust (period tracking app designed by women), and Zella Health (AI-powered reproductive health diagnostics).
• For those seeking venture capital careers, Dawn recommends building a track record through shadow portfolios or small angel investments and developing deal flow by networking with founders.

Resources:

• Capital F Fund
• The Council
• Archive Resale
• Forerunner Ventures

What if ending homelessness wasn't actually that complicated? Amy King, co-founder of Pallet, isn't just building a social enterprise; she's proving you can tackle massive societal problems while building a profitable business that attracts serious investors.

**Ready to love your Mondays? Buy 'Work That's Worth It' now - Amazon, B&N, Bookshop.org. OR, need more convincing? Get the first chapters FREE here.**

In this episode, she breaks down why most world-changing ideas never get off the ground (hint: people make them too complicated), reveals her "sphere of influence" strategy for turning big dreams into actionable plans, and shares how she built a powerhouse team of mentors.

Amy's approach to visionary thinking combined with grounded strategy will completely shift how you think about your own 90,000 hours and what's actually possible when you find your one word to guide your career.

Ever feel frustrated watching friends chase high-paying jobs while ignoring meaningful impact? You're not alone. In this candid solo episode, I tackle the question that keeps coming up at every speaking event: "How do I convince my peers to prioritize purpose over just salary?"

**Ready to love your Mondays? Buy 'Work That's Worth It' now - Amazon, B&N, Bookshop.org. OR, need more convincing? Get the first chapters FREE here.**

Drawing from a powerful conversation at Stanford and my three-phase judgment framework, I'll reveal why trying to change others' career choices is actually counterproductive—and I will share what actually works.

If you've ever wondered whether you should speak up about friends' career choices or just focus on your own path, this episode will completely shift your perspective.

Resources:

Poly Market
OECD Research
The OpED Project
LinkedIn
Instagram

From caddying for golfers at age 12 to managing a 1,000-person team at Citi Bike and now co-founding a climate-focused venture capital fund, Laura Fox's career journey exemplifies what's possible when curiosity drives your decisions instead of fear.

**Ready to love your Mondays? Buy 'Work That's Worth It' now - Amazon, B&N, Bookshop.org. OR, need more convincing? Get the first chapters FREE here.**

In this captivating conversation, Laura shares how she transformed Citi Bike into a +$100M business while making sustainable transportation accessible to millions, before pivoting to invest in groundbreaking climate solutions for urban environments.

Drawing wisdom from her grandmother's appreciation for life's small wonders, Laura reveals why the "forest path" approach to career building—following your interests rather than a straight line—has allowed her to make both meaningful impact and financial success throughout her journey.

Whether you're considering business school, wondering how to evaluate career pivots, or curious about the climate tech investment landscape, Laura's refreshing perspective on embracing challenges will inspire you to approach your own 90,000 hours with renewed purpose.

Key points:

• Laura Fox is co-founder and managing partner of a venture capital fund focusing on the intersection of cities and climate, targeting early-stage B2B companies in mobility, logistics, buildings, energy, waste, water, and adaptation.
• Her non-linear career path has included working at Morningstar, museums in Qatar, urban strategy in Bangladesh, NYU business school, Boston Consulting Group, Sidewalk Labs (Google subsidiary), and as general manager of Citi Bike at Lyft.
• Laura attributes her success to curiosity and a willingness to embrace challenges rather than following a straight career path.
• Her grandmother was a significant influence, teaching her to appreciate both big-picture thinking and small everyday details, fostering a lifelong beginner's mindset.
• Working as a golf caddy for seven summers taught Laura valuable skills in connecting with people from different backgrounds and learning through asking questions.
• At Citi Bike, Laura grew it from a $30 million to $120+ million revenue business, making it the 20th largest transportation service in the US.
• When evaluating companies to invest in, Laura focuses on businesses solving real problems with significant impact potential, like Ryzm (climate risk mapping for infrastructure) and Public Grid (reducing utility costs for renters).
• Understanding customer pain points is crucial - at Citi Bike, environmental benefits ranked low (#15) compared to immediate benefits like saving time, money, and improving physical/mental health.
• Laura advises that starting a VC fund is best later in career when you have financial buffer and relevant experience to provide value beyond funding.

Resources:

• NYU Stern
• Boston Consulting Group
• http://www.sidewalklabs.com/
• City Bike (Lyft)
• Climate Tech VC Resources
• Ted Talk

Are you chasing your purpose, or just a paycheck? Elspeth Jones had it all — a lucrative law career, financial stability, and a future that looked perfect on paper. Until one day, she started to question the true value of her work.

**Ready to love your Mondays? Buy 'Work That's Worth It' now - Amazon, B&N, Bookshop.org. OR, need more convincing? Get the first chapters FREE here.**

In this episode, she shares why she finally walked away and how that pivotal decision led to alignment, growth, and real-world impact at ClientEarth. We discuss the common struggle of choosing between financial security and meaningful work, the risks of waiting too long to make a change, and the freedom that comes with purpose-driven work.

Tune in to discover how meaning and success can still go hand in hand when you focus on the contribution you want to make in the world (versus the income you are chasing)!

Today's guest is Rebecca Van Bergen, founder of Nest, a nonprofit organization that champions the handworker economy and supports artisans around the world.

**Ready to love your Mondays? Buy 'Work That's Worth It' now - Amazon, B&N, Bookshop.org. OR, need more convincing? Get the first chapters FREE here.**

Rebecca exemplifies what happens when someone takes an early leap into meaningful work, building a business that authentically reflects who she is. Twenty years ago, as a fresh social work graduate, Rebecca won a business plan competition that provided seed capital to start Nest. Rather than following a traditional career path, she immediately began creating a platform that helps women artisans build sustainable businesses across 123 countries.

Recognized as a PBS Changemaker, World Economic Forum Young Global Leader, and Ashoka Fellow, Rebecca offers invaluable wisdom on building a purpose-driven enterprise that challenges traditional business models while creating economic opportunities for women worldwide.

Her story offers powerful insights into creating an enterprise aligned with your values and finding fulfillment through supporting others' creativity and economic independence.

Key points:

• Rebecca founded Nest after graduating with a social work degree, inspired by Muhammad Yunus winning the Nobel Peace Prize for microfinance in the same year.
• Rather than focusing solely on providing debt for women entrepreneurs, Nest creates supportive environments for craft enterprises through training and market access.
• Nest's Artisan Guild connects craft enterprises globally, with members in 123 countries and all 50 US states, providing e-learning and business development resources.
• Nest partners with major brands and retailers like Etsy, Target, Patagonia, and Williams-Sonoma to connect artisans with markets and ensure ethical sourcing.
• The Uplift Makers program with Etsy has helped bridge the digital divide for cultural communities, including Native makers, Gee's Bend quilters, and Gullah Geechee basket weavers.
• Nest developed a seal of ethical handcraft for globally produced artisanal items, ensuring fair pay and no child labor for home-based producers.
• Craft has historically been marginalized as "women's work" despite being a major income driver for women globally and providing flexible work options.
• The organization focuses on active listening to makers' needs and willingness to iterate programs based on feedback.
• As technology advances, consumer demand for handcrafted items has grown as people seek an antidote to digital life.
• Rebecca built her business skills through learning-by-doing and seeking mentors, maintaining a financially conservative approach to ensure sustainability.
• Nest runs a volunteer program connecting professionals with makers who need support in areas like web design, sales strategy, and logistics.
• Rebecca emphasizes the importance of building confidence to overcome imposter syndrome, which she reframes as "pioneer syndrome" when doing innovative work.