Behind the Business with Michelle Toh

Arum Kang, co-founder and former longtime CEO of Coffee Meets Bagel, is our guest this week. She's one of three Korean sisters who, back in 2012, were fed up with how online dating often felt dejecting and demoralizing — especially for women. Their solution? To create a serious dating app. From the start, it billed itself as a platform for serious daters, boldly calling the app “the anti-Tinder.” This meant that instead of giving users a sea of endless swipes to go through, it sent them just one curated match each day. Together, the Kangs have turned Coffee Meets Bagel into a household name. But not without plenty of tears, workshopping, sisterly "bickering" and key leadership lessons along the way. The company reports that 91% of its users are looking for a serious relationship — and have no time to waste. Meanwhile, the Asian American community, along with users in the Asia Pacific region, have become the app’s biggest drivers of growth. We discuss: | 00:00:00: Introduction  | 00:04:51: Growing up between South Korea and Hawaii, and the fear of being “ordinary” that fueled her ambition  | 00:07:41: Lessons from Harvard Business School and conceiving the idea for Coffee Meets Bagel  | 00:13:13: Convincing her sisters to leave their high-paying jobs to start the company together  | 00:16:13: Building early traction through a minimum viable product (MVP), testing, and word of mouth in the online dating space  | 00:20:55: Working with family  | 00:24:36: The pressure of juggling life as a working mom and shifting her perspective on leadership  | 00:28:11: Lessons from early hires and building company culture around trust and candor  | 00:32:31: Advice to female and minority founders on fundraising and navigating bias in venture capital  | 00:35:23: Choosing profitability over hypergrowth  | 00:38:36: Navigating crisis, mass resignations, and leadership lessons  | 00:46:01: Why “hi” isn’t enough — fixing the small-talk problem in online dating  | 00:47:13: Differentiating Coffee Meets Bagel from Tinder, Bumble, and Hinge  | 00:49:26: Outlook for Coffee Meets Bagel — doubling down on the Asian American market and expansion into Asia Pacific, the company’s biggest source of growth  | 00:51:26: Product evolution — tackling ghosting, improving safety, and using AI to foster real connections  | 00:54:16: How to stay motivated when your company no longer feels like that “shiny new dream”  | 00:56:35: The endgame for Coffee Meets Bagel — thoughts on potential exits, IPO, or long-term independence  | 00:57:40: Saying no to a surprising proposition from Mark Cuban on Shark Tank  | 00:59:53: Energy management, founder burnout, and implementing a four-day workweek  | 01:04:59: Building relationships with investors  | 01:06:41: Audience question — advice to young entrepreneurs on fundraising strategy  | 01:07:10: Rapid-fire round  | About Behind the Business: Behind the Business is a video series and podcast hosted by Michelle Toh, CNN and Fortune alum, that explores the decisions and philosophies behind today’s most influential leaders. Recorded in person across the US, the show is grounded in the belief that business is in fact personal, providing the backstories of founders, corporate leaders, investors and creators and how they push through to make the most of both work and life each day. What’s the worst day you’ve faced at your company? How do you cope with crisis or rejection? Or what’s a pinch-me moment you’ll never forget? In each episode, guests get into it all. New episodes every Thursday.  About Michelle Toh: Michelle Toh is an award-winning international journalist. She has covered some of the top stories in global business and tech, most recently as a reporter based in Hong Kong appearing across CNN’s digital and television platforms. Before joining CNN, she was an associate editor of Fortune Magazine, and her reporting has appeared in TIME, USA Today, and the South China Morning Post. Follow for episode clips and updates:Instagram: https://instagram.com/bymichelletoh TikTok: https://www.tiktok.com/@behindthebusinessshow #BehindTheBusiness #Podcast #BusinessLeadership #Entrepreneurship

Vivian Tu is the founder and CEO of Your Rich BFF, a leading financial education brand helping millions learn how to build wealth and make smarter money decisions. She left Wall Street and a lucrative career in media sales to become one of the biggest voices in the creator economy, earning over $7 million by age 31 and gaining about 10 million followers across social media. Known online as “your favorite Wall Street girly,” Vivian teaches financial literacy lessons you never got in school — from understanding the economic cost of war and the impact of interest rate cuts to mastering budgeting, investing and paycheck management. A former JPMorgan trader, Vivian transitioned from finance to media sales before becoming a full-time content creator and entrepreneur. Today, she runs a seven-figure business that includes a book, podcast, major brand partnerships, and a growing portfolio of content designed to make personal finance simple, relatable and empowering. In this conversation, we get into: | 00:00: Introduction | 01:41: Wall Street & BuzzFeed beginnings | 04:25: How immigrant parents shaped her relationship with money | 05:44: The three money rules everyone should know | 06:15: “The most important financial decision" you'll ever make | 07:32: Working with today's job & stock markets| 09:02: Getting started on Wall Street and how it shaped Vivian's path | 12:46: Experiencing bad bosses & injustice in the workplace | 13:50: The story behind the term "Your Favorite Wall Street Girly"  | 16:57: Life-changing mentors | 18:00: From Wall Street to BuzzFeed making up to $625k/ year in sales| 19:15: "I rake it up" - Vivian's deal song | 20:41: The viral video that changed everything — and moment she decided to bet on herself  | 26:02: Dealing with the social pressure when leaving the "traditional path" | 31:17: Time boxing & structuring her schedule as a new founder  | 33:15: The team behind the business of "Rich BFF"  | 34:05: Breaking down her workflow & revenue streams to earn $7M/ year | 39:30: Becoming a millionaire at age 27 | 41:04: Being open with your audience & sharing personal stories | 44:34: Handling judgment & internet negativity - "Crabs in a bucket" | 47:34: Upcoming projects & roadmap | 48:03: Long-term vision: becoming the face of finance| 50:33: Managing finances in uncertain times | 52:21: Investing, wealth building & shifting your mindset  | 53:41: Audience question from new parents on teaching kids about money | 55:21: Rapid-fire insights: trends, tips & personal habits | About Behind the Business: Behind the Business is a video series and podcast hosted by Michelle Toh, CNN and Fortune alum, that explores the decisions and philosophies behind today’s most influential leaders. Recorded in person across the US, the show is grounded in the belief that business is in fact personal, providing the backstories of founders, corporate leaders, investors and creators and how they push through to make the most of both work and life each day. What’s the worst day you’ve faced at your company? How do you cope with crisis or rejection? Or what’s a pinch-me moment you’ll never forget? In each episode, guests get into it all. New episodes every Thursday. About Michelle Toh: Michelle Toh is an award-winning international journalist. She has covered some of the top stories in global business and tech, most recently as a reporter based in Hong Kong appearing across CNN’s digital and television platforms. Before joining CNN, she was an associate editor of Fortune Magazine, and her reporting has appeared in TIME, USA Today, and the South China Morning Post. Follow for episode clips and updates:Instagram: https://instagram.com/bymichelletoh TikTok: https://www.tiktok.com/@behindthebusinessshow #BehindTheBusiness #Podcast #BusinessLeadership #Entrepreneurship | Many thanks to our fantastic partner for this season of Behind the Business: Factor! Use code BTB50OFF to get 50% OFF your first Factor box plus free breakfast for 1 year at bit.ly/BTB50OFF  | The views and opinions expressed in this episode are for informational purposes only and do not constitute financial, investment or other professional advice.

Dave Gilboa is co-founder and co-CEO of Warby Parker, the eyewear brand that started with a pair of lost glasses while he was studying at Wharton Business School. In 2010, he and three friends pooled their savings and bought the company’s URL for $9. Almost everyone they spoke to said the idea would not work. Dave joins us to talk about the brand’s early days, being so frugal they practically refused to buy pens, experimenting with retail, handling rejection, raising more than half a billion dollars before going public, and staying focused on mission and purpose. He also shares new details about Warby Parker’s partnership with Google to develop AI-powered eyewear, and why he believes smart glasses may finally become a reality.  Topics discussed: | 00:00 – Introduction | 02:14 – Dave Gilboa’s early life: from Sweden to San Diego | 03:10 – From pre-med to management consulting at Bain | 04:57 – Working in finance and realizing he wanted more meaning | 05:44 – Losing his glasses and discovering a billion-dollar idea | 07:32 – Turning frustration into the Warby Parker startup | 08:45 – Why glasses are overpriced and ripe for disruption | 11:14 – How “Warby Parker” got its name from Jack Kerouac’s journals | 14:49 – Bootstrapping with friends and pooling $120K in savings | 16:13 – Spending every dollar wisely: the three-spend rule | 18:16 – Launch week chaos and the 20,000-person waitlist | 25:36 – Rejection at Wharton and early pushback on pricing | 32:29 – Fundraising journey: from seed round to Series G | 32:58 – Taking Warby Parker public through a direct listing | 34:06 – How to raise capital the right way and keep control | 36:12 – Protecting the mission by walking away from wrong investors | 37:43 – The “Buy a Pair, Give a Pair” program: 20 million glasses donated | 40:24 – Home Try-On and inviting customers into their apartments | 41:14 – The yellow school bus pop-up tour that drove national buzz | 44:11 – Scaling brick-and-mortar retail across the U.S. and Canada | 45:13 – Expanding into contacts, exams, and full-service vision care | 45:48 – Partnering with Google to build AI-powered smart glasses | 46:57 – Why Dave believes smart glasses will finally go mainstream | 48:27 – How to grow a brand with no marketing budget | 50:45 – Rapid-fire round: habits, hiring, and advice on focus About Behind the Business: Behind the Business is a video series and podcast hosted by Michelle Toh, CNN and Fortune alum, that explores the decisions and philosophies behind today’s most influential leaders. Recorded in studios across the US, the show is grounded in the belief that business is in fact personal, providing the backstories of founders, corporate leaders, investors and creators and how they push through to make the most of both work and life each day. What’s the worst day you’ve faced at your company? How do you cope with crisis or rejection? Or what’s a pinch-me moment you’ll never forget? In each episode, guests get into it all. New episodes every Thursday. About Michelle Toh Michelle Toh is an award-winning international journalist. She has covered some of the top stories in global business and tech, most recently as a reporter appearing across CNN’s digital and television platforms. Before joining CNN, she was an associate editor of Fortune Magazine, and her reporting has appeared in TIME, USA Today, and the South China Morning Post.. Follow for episode clips and updates:Instagram: https://instagram.com/bymichelletoh TikTok: https://www.tiktok.com/@behindthebusinessshow #BehindTheBusiness #Podcast #BusinessLeadership #Entrepreneurship

Welcome to Behind the Business, a new podcast and video series hosted by CNN and FORTUNE alum Michelle Toh that aims to explore the decisions and philosophies behind some of today’s most influential leaders, such as the founders of Warby Parker, Coffee Meets Bagel, "Your Rich BFF" and more. Recorded in studios across the U.S. as a special interview series, the show is grounded in the belief that business is in fact personal, providing the backstory of founders, corporate leaders, investors, and creators and how they push through to make the most of both work and life each day. What’s the worst day you’ve faced at your company? How do you cope with crisis or rejection? Or what’s a pinch-me moment you’ll never forget? In each episode, our guests get into it all. Coming out Fall 2025. New episodes Thursdays.