
Billion Dollar Moves™ with Sarah Chen-Spellings | Global Venture Capital
Lead, build, and invest better.Join award-winning entrepreneur and investor Sarah Chen-Spellings as she travels across the globe in search of what she calls the 'unexpected leader'.Every week, we deconstruct the Billion Dollar Moves of unicorn founders & funders; many of them underestimated long before they became iconic.Many of them, unexpected leaders, just like you.This show is about unfiltered conversations about success, failure, fear, and courage in the pursuit of the next big thing in tech and venture.Billion Dollar Moves is proud to be part of the Hubspot Podcast Network with 10 million downloads a month as a group.
Latest episodes

Jun 26, 2025 • 41min
[REPLAY] Melinda French Gates $1Bn for Women | Erin Harkless Moore, Pivotal Ventures
Named one of Forbes’ Most Powerful Women, Melinda French Gates needs no introduction. Over the last twenty years through her work at the Bill & Melinda Gates Foundation, one thing has become clear to her: If you want to lift a society up, you must invest in women.
This week's replay featured Erin Harkless Moore, Senior Director of Investment for Pivotal Ventures, a Melinda French Gates company created to do exactly that. To accelerate social progress in the U.S by investing in women’s power and influence. As a member of Pivotal’s Executive Leadership Team, Erin leads the organization’s fund, and direct investment decisions, overseeing a diverse portfolio of investments that drive breakthrough innovations and drive impact for people in the US.
With nearly 20 years of investment experience, building customized portfolios for endowed institutions and family offices, serving most recently as Managing Director at Cambridge Associates, we talk about everything from challenging the status quo to her investment strategy. You don’t want to miss this!
TIMESTAMPS:
00:00 - Intro
02:04 - Erin's career, passion, profit, purpose
05:53 - The premium of 'track record'
07:58 - Investment in diversity initiatives under attack
10:53 - Where does the resistance come from?
12:30 - The role of consultants
16:01 - Melinda French Gates' point of impact
18:20 - Investing in women is not charity
24:24 - Getting to a 'yes' as an LP
30:22 - Cracking the patterns of history
Pivotal Ventures | A Melinda French Gates Company
Investing | Pivotal Ventures
Breaking With Tradition | Pitchbook
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PODCAST INFO:
Podcast website: https://billiondollarmoves.com
Watch on Youtube: https://tinyurl.com/sarahchenglobal
Join the community: https://sarah-chen.ck.page/billiondollarmoves
FOLLOW SARAH:
LinkedIn: https://linkedin.com/in/sarahchenglobal
Instagram: https://instagram.com/sarahchenglobal
X/Twitter: https://x.com/sarahchenglobal

Jun 19, 2025 • 52min
Scaling with Purpose: Antler’s Global Thesis on Intentionality & Outlier Returns w/ Rosalind Bazany
In this episode of our mini series #MeritInMotion, we’re joined by Rosalind Bazany, Head of ESG and Impact at Antler, one of the world’s most active and selective early-stage VCs. As a pledge partner of Beyond The Billion, Antler has helped deploy capital into nearly 3,000 women through its founder residencies—without any diversity quotas.
From her childhood to managing hedge funds through the global financial crisis, Ros brings systems-level thinking to investing in outliers. We explore how Antler is rewriting the rules of venture by backing overlooked markets and underestimated founders across 27 offices and six continents—with a third of its capital going to women-led startups.
Timestamps / Key Takeaways
0:00 - Intro
02:11 - Ros’ global roots that shaped her adaptability & curiosity; joining Antler
06:21 - Inside Antler’s highly selective global model: 160,000+ applications annually, 27 offices on 6 continents, 1500+ investments made
08:03 - Antler VS Y Combinator; backing PEOPLE before ideas: commercial viability and adaptability as key early traits
12:55 - Female founders with real returns under Antler’s portfolio; driving returns with intentionality, not hard quotas nor mandates
24:22 - Impact ≠ Concessionary Returns
27:46 - Exits and long-term view with liquidity on horizon
30:19 - Sustainability as strategy: backing the outliers; leveraging Antler’s global programs to source the best of the best
39:35 - Looking ahead for Antler
42:26 - Gender lens is not a filter but a strategic aperture
46:07 - Billion Dollar Questions
About Rosalind Bazany
Ros Bazany is Head of ESG and impact at Antler and currently based in Singapore. Ros is responsible for leading the overall strategy design and implementation of Antler’s ESG and impact proposition to deliver long-term value for Antler’s stakeholders. This includes oversight of firm level practices, founder engagement and investment decision making processes.
Prior to this, she worked at the global asset manager Schroders for over 10 years, working with institutional and retail clients, including on a number of strategic ESG initiatives, across Europe and Asia. She started her career at the hedge fund BlueCrest and holds an MSc in Chemistry.
She is passionate about making ESG and impact a tool to create value for our founders, Antler and the industry more broadly.
Read more about Antler’s 2024 ESG and Impact Report: https://www.antler.co/sustainability
Follow Ros & Antler:
https://www.antler.co/
https://www.linkedin.com/in/rosalind-bazany-a225275/
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PODCAST INFO:
Podcast website: https://billiondollarmoves.com
Watch on Youtube: https://tinyurl.com/sarahchenglobal
Join the community: https://sarah-chen.ck.page/billiondollarmoves
FOLLOW SARAH:
LinkedIn: https://linkedin.com/in/sarahchenglobal
Instagram: https://instagram.com/sarahchenglobal
X/Twitter: https://x.com/sarahchenglobal

Jun 12, 2025 • 38min
From Viral Videos to Brain Chips: The Future of Human-AI Evolution w/ Taryn Southern
What happens when a viral creator becomes a deep tech investor—and then starts working on brain chips?
In this episode, we go beyond the hype with Taryn Southern—early YouTube pioneer, Emmy-nominated filmmaker, and now a leading voice in neurotechnology and AI. From releasing the world’s first AI-generated music album to working at the frontier of brain-computer interfaces with Blackrock Neurotech, Taryn opens up about redefining creativity and investing in future-defining tech.
You’ll walk away with a practical AI prompt framework, hard truths about what it takes to bet smart on deep tech—and a powerful reminder of what it really means to be human in an age of machines.
Timestamps / Key Takeaways
0:00 - Intro
01:43 - From Anthropology to youtube stardom—then diving into AI & Neurotech
07:04 - The first artist to release a full AI-generated music album: why AI enhances creativity, not threatens it
12:45 - Upskilling for the AI era; The G.R.I.P.E. framework: How to prompt ChatGPT like a pro
16:18 - The science and reality behind BCI; Blackrock Neurotech’s critical technologies for ALS patients, funding and capital
26:47 - The future of AI for women; AI investment advice & the questions you should be asking
32:24 - Billion Dollar Questions with Taryn Southern
About Taryn Southern
"Deeply thoughtful yet boundlessly optimistic."
Taryn Southern is an award-winning storyteller and creative technologist exploring the intersection of emerging tech and human potential. Her groundbreaking creative experiments offer unique insights into how technology can help us unleash creativity, joy, wellbeing and productivity.
Originally from Kansas, Taryn’s first foray into entertainment began at 17 when she competed in the semi-finals of American Idol. In 2007, after obtaining degrees in journalism and anthropology, Taryn uploaded her first video onto YouTube.
Ten years and 750 million views later, this early YouTuber produced more than 1500 internet videos, at the forefront of the online content revolution. In 2007, she hosted and produced a TV series documenting her travels to meet her MySpace friends and uploaded her first viral video to YouTube.
Over the next decade, she created over 1500 videos garnering more than 1 billion views, served as an early advisor to YouTube, Google VR and Snapchat product teams, and consulted for companies like Conde Nast and Marriott on digital content strategy and narrative design.
FOLLOW TARYN
https://tarynsouthern.com/
https://www.instagram.com/tarynsouthern/
https://www.youtube.com/TarynSouthern
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PODCAST INFO:
Podcast website | Watch on Youtube | Join the community
FOLLOW SARAH:
LinkedIn | Instagram | X/Twitter

Jun 5, 2025 • 27min
Why 8 in 10 LPs Still Don’t Back Women—And What Ankita’s Doing About It
Venture capital is changing—and so is India. In this episode, we dive deep with Ankita Vashistha, the trailblazing investor behind Saha Fund and Arise Ventures.
From building Singapore’s first government-backed fund to leading a ₹500 Crore gender-lens powerhouse, Ankita’s story is one of grit, foresight, and redefining alpha. With 5 unicorns, 50+ investments, and a global accelerator reaching 5,000+ founders a year—this is more than investing. It’s revolution.
Timestamps / Key Takeaways
0:00 - Intro
01:50 - #1 From Copycat to Category Creator – The Rise of India as a Global Builder
08:32 - #2 Gender Lens ≠ Charity. It’s Alpha.
17:53 - #3 The Venture Capital Playbook Needs a Reboot—For India
19:42 - #4 From Capital Allocator to Company Builder
21:47 - #5 Be Loud. Be Clear. Be Your Own Champion.
22:47 - Closing Remark:Legacy in Motion
ABOUT ANKITA
With over 16 years of experience in private equity, venture capital, innovation, diversity and impact investing, Ankita is a passionate and visionary venture capital investor and entrepreneur.
Ankita founded and led two pioneering funds, StrongHer Ventures and Saha Fund, that invest in and promote women engagement, empowerment and entrepreneurship through digital technology and now leading her third fund - Arise Ventures.
Ankita also co-authored of the book "Innovation at Scale", which covers how digital is transforming industries and creating opportunities for women.
FOLLOW ANKITA:
https://www.linkedin.com/in/ankitavashistha/
https://www.instagram.com/ankitasvashistha/
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PODCAST INFO:
Podcast website: https://billiondollarmoves.com
Watch on Youtube: https://tinyurl.com/sarahchenglobal
Join the community: https://sarah-chen.ck.page/billiondollarmoves
FOLLOW SARAH:
LinkedIn: https://linkedin.com/in/sarahchenglobal
Instagram: https://instagram.com/sarahchenglobal
X/Twitter: https://x.com/sarahchenglobal

May 29, 2025 • 48min
The Rise of the Solo Capitalist: How One-Person Funds Are Winning Big w/ Itamar Novick, Recursive Ventures
With 25 years across engineering, operating, and venture capital, Itamar Novick knows what it takes to build billion-dollar companies—because he’s done it. From betting his life savings on Life360 (now $4.5B public) to helping 60+ startups raise Series A, Itamar shares the unfiltered playbook on solo capital, Pre-Seed power moves, and why he’s staying small in a mega-fund world.
Tune in for tactical insights on fundraising, AI investing, and VC truths founders should know!
TIMESTAMPS / KEY TAKEAWAYS
0:00 - Intro
02:10 - From Sandhill Road to solo GP: Itamar’s founder-focused philosophy
06:14 - Itamar’s bet on Life360: investing life savings and the $4.5B IPO journey
10:00 - Pivoting framework: ‘Time is money and money is time’
13:42 - The birth of Recursive Ventures
15:14 - Rise of solo GPs: How Tech, AI, & LPs making it more feasible
18:02 - AI’s role in venture — replacing VCs?
21:18 - Pre-Seed investing strategy: Staying small, focused, and lean.
24:44 - Trend of Mega Funds as financial services firms
27:35 - Returning capital before IPOs: Liquidity and Secondaries
33:54 - AI investing deep dive: Infra vs. application layer; importance of Moat
40:14 - Founders’ pitfalls: dilution, anti-patterns, and mispriced valuations
44:03 - Billion Dollar Questions
About Itamar Novick
Itamar is a solo capitalist and the founder of Recursive Ventures, a pre-seed fund focused on fintech, AI and emerging tech startups. Itamar has been on all sides of the startup table: as a founder and executive, an institutional VC, and an angel investor.
He has supported over 50 successful startups, including Deel, Honeybook, Placer, Credible (IPO), MileIQ (acquired by Microsoft), Automatic Labs (acquired by SiriusXM), Tile (acquired by Life360), SafeGraph, and Armory. He’s been recognized by Business Insider as a Top 100 global seed investor. As an operator, he helped take Life360 from Seed to IPO, scaling the business to over $250m in revenue.
Before that, Itamar was a founding team member and head of Product at Gigya (acquired by SAP). He holds an MBA from Berkeley Haas and an undergraduate degree in computer science from the Tel-Aviv Jaffa College.
FOLLOW ITAMAR:
https://www.itamarnovick.com
https://x.com/Itamar_Novick
https://www.linkedin.com/in/itamarnovick/
About Recursive Ventures
Recursive Ventures is a San Francisco based VC fund investing in US Pre-seed and Seed Tech Startups disrupting industries through use of Data and Artificial Intelligence. Recursive is managed by Itamar Novick with support from a seasoned group of Founders, Operators, and go-to-market experts.
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PODCAST INFO:
Podcast website: https://billiondollarmoves.com
Watch on Youtube: https://tinyurl.com/sarahchenglobal
Join the community: https://sarah-chen.ck.page/billiondollarmoves
FOLLOW SARAH:
LinkedIn: https://linkedin.com/in/sarahchenglobal
Instagram: https://instagram.com/sarahchenglobal
X/Twitter: https://x.com/sarahchenglobal

May 22, 2025 • 17min
[BITE] The Big Bet Mindset: Building Bold, Lasting Change w/ Dr. Raj Shah, The Rockefeller Foundation
Summer’s almost here—and with it, a moment to reflect on what it really takes to spark lasting, meaningful change. In a world where progress often feels slow and the stakes impossibly high, Dr. Rajiv Shah has spent his career proving that bold, system-shifting bets can work.
From leading global vaccine efforts at the Gates Foundation, to reshaping food security policy at USAID, to now powering innovation at The Rockefeller Foundation—Raj’s story is one of grit, vision, and conviction.
This conversation is a masterclass on making big bets: how to build unlikely alliances, act with urgency, and stay grounded in optimism—even when the odds feel stacked.
If you’re a leader wondering “Where do we go from here?”—this one’s for you.
Let’s dive in.
Timestamps / Key Takeaways
0:00 - Intro
01:32 - Key Takeaway #1: The 3 key elements of big bets:
04:38 - Key Takeaway #2: It is realistic to be optimistic about grand-scale changes.
09:22 - Key Takeaway #3: Keep taking the risks, keep reinventing.
12:05 - Key Takeaway #4: Crossing boundaries IS part of the process
15:08 - A powerful reminder: every billion-dollar move starts with conviction, clarity, and courage.
About Dr Rajiv Shah
Dr. Rajiv J. "Raj" Shah was born to Indian immigrant parents who settled in Ann Arbor, Michigan in the late 1960s. He joined the Bill & Melinda Gates Foundation in 2001, serving in a range of leadership roles including Director of Agricultural Development, Director of Strategic Opportunities, Deputy Director of Policy and Finance and Chief Economist. During his time in Bill & Melinda Gates Foundation, he was also responsible for developing the International Finance Facility for Immunization, which raised more than $5 billion for the Global Alliance for Vaccines and Immunization (GAVI).
Throughout Obama administration, Raj was nominated to serve United States Department of Agriculture (USDA) and United States Agency for International Development (USAID). As Administrator of USAID, he restructured $2.9 billion of global health investments to focus on cost-effective ways to save lives of children under the age of five in priority countries.
On January 5, 2017, Raj Shah was sworn to serve as the 13th president of the Rockefeller Foundation, continuing the mission of the foundation to improve the lives of humanity around the world.
In 2023, he authored the book "Big Bets: How Large-Scale Change Really Occurs,”, offers insights into some of his experiences in philanthropic and public service work, as well as the lessons he has learned throughout his career on how to drive transformational change through a big-goal mindset.
FOLLOW DR. RAJ
Instagram | LinkedIn | X/Twitter
Rockefeller Foundation - Big Bets
https://www.rockefellerfoundation.org/bigbets
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PODCAST INFO:
Podcast website: https://billiondollarmoves.com
Watch on Youtube: https://tinyurl.com/sarahchenglobal
Join the community: https://sarah-chen.ck.page/billiondollarmoves
FOLLOW SARAH:
LinkedIn: https://linkedin.com/in/sarahchenglobal
Instagram: https://instagram.com/sarahchenglobal
X/Twitter: https://x.com/sarahchenglobal

May 15, 2025 • 52min
Breaking VC Stereotypes: Power, Privilege, and Purpose w/ Jesse Draper, Halogen Ventures
Her great-grandfather helped birth the VC industry. Her father, Tim Draper, made game-changing bets on Tesla, Hotmail, and Skype.
But Jesse Draper? She’s carved her own path—first as a Nickelodeon actress, then as the creator of The Valley Girl Show, and now as the founding partner of Halogen Ventures. With over 75 female-founded companies under her belt, Jesse is proving that investing in women isn't charity—it's just good business.
From battling biases in the boardroom to rewriting what venture capital looks like through the lens of the modern family, this episode is Jesse Draper like you've never heard her before. Let’s dive in!
Timestamps / Key Takeaways
0:00 - Intro
01:52 - Jesse Draper’s early aspirations; family legacy & "Nepo Baby" pushback
05:21 - Starting a Tech talk show — The Valley Girl Show from her parents’ garage
10:16 - Pivoting to venture; early angel investments led to major returns: Laurel & Wolf with 26X return
13:17 - From Valley Girl persona to founding Halogen Ventures
21:28 - Thesis and conviction: Fund 1 raised $10.4M
27:27 - Childcare economy; Halogen doubling down on future of family
34:43 - Challenges with fundraising & biases; advice to women navigating wealth and power
47:50 - Billion Dollar Questions
About Jesse
Jesse Draper is a mother of 3 boys and founding partner of Halogen Ventures. Halogen Ventures is a Los Angeles based Venture Capital firm focused on early stage investing in consumer technology and strategic B2B software companies with a female in the founding team. Draper, the first solo female GP in Los Angeles, is also a 4th generation venture capitalist, the creator and host of Emmy nominated television series, The Valley Girl Show, and host of the MOMumental Podcast.
She is a fierce advocate for investing in women and the opportunity for using technology and innovation to solve some of the biggest issues facing women and families today. Among her 70+ portfolio companies, are theSkimm, Babylist, ThirdLove, HopSkipDrive, The Flex Company, Squad (acquired by Twitter), Eloquii (sold to Walmart) and This is L (sold to P&G).
Selected as one of the top 10 early stage female investors by Business Insider, Draper was also listed by Marie Claire magazine as one of the ‘50 Most Connected Women in America’, nominated by the NRF as a DealMakeHers, Variety’s Holly’s New Leaders, and Refinery29 30 Rising Stars.” Draper has been a contributor to Marie Claire, Forbes, and is a regular investor and tech personality showcased on Cheddar, CNBC, CNN. Following Jesse’s viral Medium piece, Investing in Women Isn’t a F*cking Charity, she’s become a leading voice of women in technology. Draper is also a Kauffman Fellow.
FOLLOW JESSE:
https://www.linkedin.com/in/jessedraper/
https://www.instagram.com/jessecdraper/
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PODCAST INFO:
Podcast website: https://billiondollarmoves.com
Watch on Youtube: https://tinyurl.com/sarahchenglobal
Join the community: https://sarah-chen.ck.page/billiondollarmoves
FOLLOW SARAH:
LinkedIn: https://linkedin.com/in/sarahchenglobal
Instagram: https://instagram.com/sarahchenglobal
X/Twitter: https://x.com/sarahchenglobal

May 8, 2025 • 22min
Leadership Redefined: Inside the Playbooks of AANHPI Founders and Funders
In this AANHPI Heritage Month special, we go beyond the headlines to uncover the real strategies behind extraordinary leaders who happen to be Asian American, Native Hawaiian, and Pacific Islander.
From billion-dollar founders to high-conviction investors, this episode dives into the mindset, grit, and quiet strength that drive lasting impact—not just success. You'll hear unfiltered insights from Melanie Perkins, Canva; Steve Chen, YouTube; Cathy Gao, Sapphire Venture; Kimberly Yao, CloudEats; Lisa Su, AMD; Momei Qu, PSP Partner; and James Rhee, the red helicopter; as they redefine what it means to lead in today’s world.
This isn’t just about representation—it’s about outperformance.
TIMESTAMPS / KEY TAKEAWAYS
0:00 - Intro
0:52 - Key Takeaway #1: Entrepreneurial Grit and Innovation
09:06 - Key Takeaway #2: Leadership Lessons
15:37 - Key Takeaway #3: The Quiet Power of Humility
20:28 - Final takeaway: Treat grit as an input. Identity as insight. And never underestimate the quiet builders.
WATCH THE FULL EPISODES:
Journey after YouTube w/ Steve Chen, Draco Evolution
https://www.billiondollarmoves.com/journey-after-youtube-steve-chen-draco/
Enterprise is Eating The World with Cathy Gao, Sapphire Ventures
https://www.billiondollarmoves.com/enterprise-is-eating-the-world-cathy-gao-sapphire-ventures/
Bite: Evolving as a CEO That Your Company Needs with Kim Yao, CloudEats
https://www.billiondollarmoves.com/bite-evolving-CEO-scaling-company-kim-yao-cloudeats/
Investing with Penny Pritzker and Building a Robust Venture & Growth Practice with Momei Qu, MD, PSP Partners
https://www.billiondollarmoves.com/building-robust-venture-growth-practice-with-momei-qu-md-psp/
CEO Series: Lisa Su, AMD
https://www.billiondollarmoves.com/ceo-series-lisa-su-amd/
CEO Series: Melanie Perkins, Canva
https://www.billiondollarmoves.com/ceo-series-melanie-perkins-canva/
Leading with Kindness: The Power of Goodwill with James Rhee, Owner, Red Helicopter, TEDTalk Speaker
https://www.billiondollarmoves.com/leading-with-kindness-the-power-of-goodwill-james-rhee-red-helicopter/
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PODCAST INFO:
Podcast website: https://billiondollarmoves.com
Watch on Youtube: https://tinyurl.com/sarahchenglobal
Join the community: https://sarah-chen.ck.page/billiondollarmoves
FOLLOW SARAH:
LinkedIn: https://linkedin.com/in/sarahchenglobal
Instagram: https://instagram.com/sarahchenglobal
X/Twitter: https://x.com/sarahchenglobal

May 1, 2025 • 37min
The LP-to-GP Journey: Rewriting VC Playbook With A Marketing Edge w/ Laurel Mintz, Fabric VC
Laurel Mintz is not your typical VC. At just 26, she stepped in to run her father’s Bassett Furniture business — managing 60 employees and learning leadership the hard way. From there, she launched Elevate My Brand, a marketing powerhouse behind hundreds of consumer brands — many of which went on to raise capital.
Today, she’s rewriting the VC playbook with Fabric VC, a seed-stage fund turning marketing into a superpower for picking and growing winners. In this episode, Laurel opens up about her first LP check, flipping the script on fundraising, using proprietary diligence tools, and why investing in diverse founders isn’t charity — it’s a smart business model.
If you’re a founder, funder, or future GP — this one’s a masterclass.
TIMESTAMPS / KEY TAKEAWAYS
0:00 - Intro
02:12 - From lawyer to founder: interim CEO for Bassett Furniture; founded Elevate My Brand
05:19 - 16 years of marketing experience; first LP check into Halogen Ventures’ Jesse Draper
09:56 - Why Fabric VC? The data-backed diversity bet
13:00 - AI hype; secondary diligence layer using marketing listening software
17:27 - Sweat equity + marketing as a VC edge
21:32 - Fundraising lessons: the mindset shift and the rolling raise / rolling deploy strategy
23:31 - Empowering new female LPs & destigmatizing money talk
27:58 - Laurel’s exit strategy philosophy & her bets for the future
31:58 - Billion Dollar Questions
ABOUT LAUREL
As founder of Elevate My Brand, Laurel has spent 16 years turning bold ideas into measurable growth for over 400 powerhouse brands like Verizon, Paw Patrol, Zendesk, Geico and Squishmallows. Their marketing strategies don’t just look good—they drive visibility, profitability, and real results.
In parallel, as General Partner at Fabric VC, Laurel invests in the next wave of consumer-tech, health, and fintech founders. With a marketer’s lens and a strategist’s mindset, she helps visionary startups scale smart and stay seen. Across both roles, her mission is simply described as fuel innovation and impact, elevate bold ideas, and build what’s next.
FOLLOW LAUREL:
https://www.linkedin.com/in/laurel-mintz
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PODCAST INFO:
Podcast website: https://billiondollarmoves.com
Watch on Youtube: https://tinyurl.com/sarahchenglobal
Join the community: https://sarah-chen.ck.page/billiondollarmoves
FOLLOW SARAH:
LinkedIn: https://linkedin.com/in/sarahchenglobal
Instagram: https://instagram.com/sarahchenglobal
Twitter: https://x.com/sarahchenglobal

Apr 24, 2025 • 43min
[REPLAY] Pivot or Persevere? Being a Growth Company CEO w/ Jeff Maggioncalda, Former CEO of Coursera
In this engaging discussion, Jeff Maggioncalda, former CEO of Coursera and Financial Engines, shares insights from his remarkable career. He reflects on pivotal leadership moments, the importance of knowing when to pivot, and how a simple game of Monopoly influenced his journey. Jeff dives into the evolution of AI and its impact on investment and education, revealing how platforms like Coursera reshape digital learning. He emphasizes adaptability in entrepreneurship and the promising yet complex future of AI in the workforce.