Christina Cacioppo never fit Silicon Valley's picture of a tech founder. She didn't grow up coding, spent two years in venture capital before teaching herself to program, and sold her first startup for $20,000 after none of its products found a market. Today she is the co-founder and CEO of Vanta, the compliance automation company that raised a $150 million Series D at a $4.15 billion valuation and, as of April 2026, has passed $300 million in ARR. Vanta now serves more than 16,000 organizations, including Snowflake, Duolingo, Ramp, Cursor, and Harvey, with just 1,000 employees across five offices.

In this episode, Ruffin traces Christina's path from running a Beanie Baby business on eBay at age 11, to meeting hundreds of founders at Union Square Ventures, to learning how real product teams work as a PM at Dropbox. The episode walks through the ideas that didn't work, including a voice assistant for lab biologists with a market "the size of my thumb," and the customer discovery rule that finally led Christina to Vanta: no code until you truly understand the problem. You'll also hear how Vanta started as a SOC 2 consultancy run out of a spreadsheet, won its first 600 customers without a real website, and waited until $10 million in ARR, ten times the usual benchmark, to raise its Series A from Sequoia.

It's a story about resilience with discernment: staying committed to the ambition without getting attached to the wrong idea.

I hope you enjoy!

This episode is brought to you by Vanta. Get $1,000 off at https://vanta.com/ruffin

More on Christina Cacioppo:

LinkedIn: https://www.linkedin.com/in/ccacioppo

X: https://x.com/christinacaci

More on Vanta:

Website: https://www.vanta.com

More on Host Ruffin Mitchener:

https://beacons.ai/ruffin

About Brydge Club:

Brydge Club, hosted by Ruffin Mitchener, aims to bridge the $1.7 trillion financing gap for female founders. Every Wednesday, the show features in-depth interviews with industry leaders and innovators, educating and empowering women in venture capital and entrepreneurship. Through insightful discussions, Brydge Club seeks to inspire listeners to break barriers and achieve success in the business world.

Jenny Duan is the CEO and Co-Founder of Clair Health, the world's first wearable for continuous hormone monitoring. She started Clair as a junior at Stanford after a class on the women's health ecosystem showed her how little data women actually have about their own bodies. While studying abroad at Oxford, she worked nights and flew to the US three times in ten weeks to pitch investors and build out the team. Clair has since raised an $11 million seed round led by Khosla Ventures with participation from a16z speedrun and Brydge Club, built a waitlist of 25,000 women, taken 6,000 preorders, and signed early B2B contracts with fertility clinics.

In this episode, Jenny explains how Clair infers hormone levels from the wrist using ten novel sensors and machine learning models trained on female physiology, and why blood draws and daily urine tests leave such a big gap. She breaks down why most wearables filter out female body data as noise, what Clair is already seeing in its own data around perimenopause and cycle phases, and what goes into the Harmony clinical study and the path to FDA clearance. She also shares how the team is protecting sensitive women's health data, what the Mayo Clinic partnership unlocks for their research, how they created early demand almost entirely through community and word of mouth, and why she believes all of healthcare is women's health.

I hope you enjoy!

This episode is brought to you by Vanta. Vanta's Agentic Trust Platform takes the manual work out of your security and compliance process and replaces it with continuous automation, whether you’re pursuing your first framework or managing a complex program.

Go to http://vanta.com/ruffin for $1,000 off Vanta today!!

More on Jenny Duan:

LinkedIn: https://www.linkedin.com/in/jennysduan

Instagram: https://www.instagram.com/jennysduan

Website: https://wearclair.com/

More on Host Ruffin Mitchener:

https://beacons.ai/ruffin

About Brydge Club:

Brydge Club, hosted by Ruffin Mitchener, aims to bridge the $1.7 trillion financing gap for female founders. Every Wednesday, the show features in-depth interviews with industry leaders and innovators, educating and empowering women in venture capital and entrepreneurship. Through insightful discussions, Brydge Club seeks to inspire listeners to break barriers and achieve success in the business world.

Welcome to the Brydge Club podcast! I'm your host, Ruffin, and today I'm going solo to break down one of the most misunderstood startup stories of the last decade: how Payal Kadakia built ClassPass.

Fewer than 1% of funded startups reach $1 billion. Only 7% of unicorn founders are women, and women of color lead even fewer. Payal is one of them. But the ClassPass we know today, with 100 million hours of workouts booked across 30,000 partners in 28 countries, is not the company she set out to build.

In this episode, I trace the full arc: from an MIT grad and lifelong dancer who couldn't find a single ballet class in New York, to spending $500,000 on a booking product that generated about ten reservations a month. I get into why the "OpenTable for fitness" thesis was built on a false parallel, the five distinct business models ClassPass cycled through, the $99 unlimited era that grew 50x while quietly bleeding money, and the decision to kill it in 2016 and lose 10% of the user base overnight.

I also dig into the part of the story that matters most to me: the rooms full of male VCs who sat in silence after every pitch, the fellow South Asian woman who wrote the first meaningful check and told her to bet on herself, and what that representation gap actually costs when you measure it in billions.

I hope you enjoy!

This episode is brought to you by Vanta. Vanta's Agentic Trust Platform takes the manual work out of your security and compliance process and replaces it with continuous automation, whether you’re pursuing your first framework or managing a complex program.

Go to http://vanta.com/ruffin for $1,000 off Vanta today!!

More on Host Ruffin Mitchener:

https://beacons.ai/ruffin

About Brydge Club:

Brydge Club, hosted by Ruffin Mitchener, aims to bridge the $1.7 trillion financing gap for female founders. Every Wednesday, the show features in-depth interviews with industry leaders and innovators, educating and empowering women in venture capital and entrepreneurship. Through insightful discussions, Brydge Club seeks to inspire listeners to break barriers and achieve success in the business world.

Eve Halimi and her co-founder Anam wrote a 100-page business plan on Saturdays while working full-time on Wall Street. Today, Alinea Invest, the AI-powered investing app they built, is used by roughly 1% of the U.S. population. In between: a Y Combinator acceptance won on founder-market fit alone, two years of iteration before anything worked, a $10 million Series A led by Play Ventures, and a $20 million cohort-financing facility that fuels their growth without touching equity.

In this episode, Eve breaks down the onboarding rewrite that took Alinea from near-zero to $80K in a single month, and the founder-led TikTok strategy that turned one 60-second story video into 50,000 downloads in a day. She gets specific on the mechanics of debt financing for consumer apps, why they waited far too long to charge for the product, how "Gen Z messaging" ended up converting 40-year-old construction workers, and what an AI investing companion that "thinks and acts for you" actually looks like.

I hope you enjoy!

This episode is brought to you by Vanta. Vanta's Agentic Trust Platform takes the manual work out of your security and compliance process and replaces it with continuous automation, whether you’re pursuing your first framework or managing a complex program.

Go to http://vanta.com/ruffin for $1,000 off Vanta today!!

More on Eve Halimi:


LinkedIn: https://www.linkedin.com/in/eve-halimi

Instagram: https://www.instagram.com/genuine.jew/?hl=en
Website: https://www.alinea-invest.com/

More on Host Ruffin Mitchener:


https://beacons.ai/ruffin

About Brydge Club:


Brydge Club, hosted by Ruffin Mitchener, aims to bridge the $1.7 trillion financing gap for female founders. Every Wednesday, the show features in-depth interviews with industry leaders and innovators, educating and empowering women in venture capital and entrepreneurship. Through insightful discussions, Brydge Club seeks to inspire listeners to break barriers and achieve success in the business world.

Welcome to the Brydge Club podcast! I'm your host, Ruffin, and today I'm joined by Laura Modi, Co-Founder and CEO of Bobbie, the infant formula company she started after a moment of shame in a pharmacy aisle. Laura built her career at Google and Airbnb before leaving tech to take on one of the most highly regulated, capital-intensive industries in America. Bobbie has since raised nearly $150 million, surpassed $160 million in revenue, and bought its own manufacturing facility in Ohio.

In this episode, Laura talks about the emotional reality behind Bobbie's founding story, what she learned about sugar and formulation by cold-emailing 20-30 experts a night, and the FDA labeling issue that pulled her product off shelves for 18 months when she had only 100 customers. She explains why she turned off new customer growth during the 2022 national formula shortage against investor advice, how she convinced her board she'd been wrong about owning manufacturing, and what responsibility every formula brand carries when a recall hits the industry. Laura also shares how the Molly Baz Times Square billboard came together, why she hires the atypical candidate, the work Bobbie for Change is doing on federal paid leave and the Black maternal mortality crisis, and the moment with her daughter that finally loosened her grip on mom guilt.

I hope you enjoy!

This episode is brought to you by Vanta. Vanta's Agentic Trust Platform takes the manual work out of your security and compliance process and replaces it with continuous automation, whether you’re pursuing your first framework or managing a complex program.

Go to http://vanta.com/ruffin for $1,000 off Vanta today!!

More on Laura Modi:

Instagram: https://www.instagram.com/lauraclairemodi/

Website: https://www.hibobbie.com/

Bobbie for Change: https://www.bobbieforchange.org/

More on Host Ruffin Mitchener:

https://beacons.ai/ruffin

About Brydge Club:

Brydge Club, hosted by Ruffin Mitchener, aims to bridge the $1.7 trillion financing gap for female founders. Every Wednesday, the show features in-depth interviews with industry leaders and innovators, educating and empowering women in venture capital and entrepreneurship. Through insightful discussions, Brydge Club seeks to inspire listeners to break barriers and achieve success in the business world.

Welcome to the Brydge Club podcast! I'm your host, Ruffin, and today I'm joined by Amy Moussavi, angel investor and advisor at Malo Partners. Amy took an unconventional path into venture. After studying cognitive neuroscience, with no background in finance, she was early at Snapchat, spent years inside a top-secret product group at Apple, and became an investor at a multi-billion-dollar VC fund before building her own portfolio of nearly 20 personal angel investments.

In this episode, Amy breaks down how she wrote her very first angel check (and the one category Apple would let her invest in), how she developed a thesis around "building for humanity of the future," and how she evaluates founders from pre-seed to Series A. She shares why she passed on Liquid Death, the speed and precision she looks for in breakout founders, how she works backwards from exit math on market sizing, and the categories she's most excited about now: women's health, longevity, AI hardware, live shopping, and Gen Alpha. Amy also gets candid about why fundraising can feel like "asking for charity" for women founders, the gotchas of stacked SPVs in today's AI-hyped market, and the advice she ignored for a decade: that in venture, relationships are everything.

I hope you enjoy!

This episode is brought to you by Vanta. Vanta's Agentic Trust Platform takes the manual work out of your security and compliance process and replaces it with continuous automation, whether you’re pursuing your first framework or managing a complex program.

Go to http://vanta.com/ruffin for $1,000 off Vanta today!!

More on Amy Moussavi:

LinkedIn: https://www.linkedin.com/in/amy-moussavi/

Pitch her: [email protected]

More on Host Ruffin Mitchener:

https://beacons.ai/ruffin

About Brydge Club:

Brydge Club, hosted by Ruffin Mitchener, aims to bridge the $1.7 trillion financing gap for female founders. Every Wednesday, the show features in-depth interviews with industry leaders and innovators, educating and empowering women in venture capital and entrepreneurship. Through insightful discussions, Brydge Club seeks to inspire listeners to break barriers and achieve success in the business world.

Morgan Zanotti built Primal Kitchen from a scrappy, bootstrapped mayonnaise brand into a $50 million business, then sold it to Kraft Heinz for $200 million just three and a half years after launch, signing the deal weeks after having her first baby at 32 weeks pregnant. After five years running the brand inside a multi-billion-dollar portfolio, she walked away to start again, this time as a solo founder building Waay, a clear whey protein isolate beverage created for women who are tired of choking down chalky shakes.

In this conversation, Morgan traces her winding path from accountant to waitress to yoga instructor to CPG operator, and unpacks why she and Mark Sisson kept 95% of Primal Kitchen by refusing outside capital. She breaks down the mechanics of actually selling a company, from the banker "bake off" to the four-day management presentations, and explains why the second time around she raised venture capital from Kate McAndrew at Baukunst instead of mortgaging her own peace of mind. Along the way she gets candid about lifelong imposter syndrome, building all-female teams, the unsexy grind behind a nine-figure exit, and why she believes being a woman in business is a superpower, not a setback.

This episode is brought to you by Vanta. Vanta's Agentic Trust Platform takes the manual work out of your security and compliance process and replaces it with continuous automation, whether you’re pursuing your first framework or managing a complex program.

Go to http://vanta.com/ruffin for $1,000 off Vanta today!!

More on Morgan Zanotti:

LinkedIn: https://www.linkedin.com/in/morgan-buehler-zanotti-31989620/

Website: https://drinkwaay.com/

More on Host Ruffin Mitchener:

https://beacons.ai/ruffin

About Brydge Club:

Brydge Club, hosted by Ruffin Mitchener, aims to bridge the $1.7 trillion financing gap for female founders. Every Wednesday, the show features in-depth interviews with industry leaders and innovators, educating and empowering women in venture capital and entrepreneurship. Through insightful discussions, Brydge Club seeks to inspire listeners to break barriers and achieve success in the business world.

Welcome to the Brydge Club podcast! I'm your host, Ruffin, and today I'm joined by Hilary Coles and Emily Boschwitz, the powerhouse duo behind POCA, a better-for-you coffee syrup that lets people enjoy their favorite café drinks without the sugar crash. Before POCA, Hilary and Emily were on the founding team at Hims & Hers, which they helped scale to a $1.6 billion valuation in just three years and take public. In this episode, Hilary and Emily trace their unlikely paths, from Hilary starting out as an admin and being turned down by nearly every "dream" company, to Emily learning to read in seventh grade and turning dyslexia into a marketing superpower. They break down the early days of Hims & Hers: why they launched with stigmatized products, how men dancing in showers with shampoo bottles became an accidental growth engine, and the channel-diversification strategy that fueled explosive scale. Then they get into POCA, the consumer insight that coffee is "the last allowable vice," how they ran a paint-the-door test before building anything, the food science behind a syrup that actually dissolves in iced coffee, and why brand matters more than ever in the age of AI slop. Along the way, they share hard-won lessons on curiosity as a career strategy, growth marketing, and the AI stack every founder should be using today.

This episode is brought to you by Vanta. Vanta's Agentic Trust Platform takes the manual work out of your security and compliance process and replaces it with continuous automation, whether you’re pursuing your first framework or managing a complex program.

Go to http://vanta.com/ruffin for $1,000 off Vanta today!!

More on Hilary Coles & Emily Boschwitz:

POCA: https://pickpoca.com/

Gossamer World: https://gossamer.world/

Hilary Coles: https://www.linkedin.com/in/hilary-coles-11803b187

Emily Boschwitz: https://www.linkedin.com/in/emilyboschwitz

More on Host Ruffin Mitchener:

https://beacons.ai/ruffin

About Brydge Club:

Brydge Club, hosted by Ruffin Mitchener, aims to bridge the $1.7 trillion financing gap for female founders. Every Wednesday, the show features in-depth interviews with industry leaders and innovators, educating and empowering women in venture capital and entrepreneurship. Through insightful discussions, Brydge Club seeks to inspire listeners to break barriers and achieve success in the business world.

In this episode, I'm breaking down one of the most remarkable stories in modern consumer business: how FIGS went from selling scrubs in hospital parking lots to becoming the first company led by two female co-founders and co-CEOs to go public on the New York Stock Exchange.

In 2012, Heather Hasson noticed a nurse friend stuck wearing shapeless, uncomfortable scrubs and saw an opportunity everyone else had ignored. Meanwhile, Trina Spear spotted the same gap from Wall Street, eventually quitting her job at Blackstone and liquidating her 401(k) to bet on it. Together they drove to hospital parking lots at 7 a.m. shift changes, coffee in hand, selling scrubs out of a car and listening relentlessly to the healthcare workers they served.

I unpack exactly what it took to build a multibillion dollar business: developing proprietary performance fabric designed for grueling shifts, going direct-to-consumer from day one, and engineering a word-of-mouth marketing machine so powerful their customer acquisition costs actually dropped as they scaled. I also dig into the hundreds of no's they heard before landing a $50 million check, the $200 million lawsuit from a legacy scrub giant they fought and won, and the way they brought 60 healthcare professionals to ring the opening bell and opened pre-IPO access to everyday investors.

It's a masterclass in product, distribution, community, and staying close to the people you serve.

I hope you enjoy!

This episode is brought to you by Vanta. Vanta's Agentic Trust Platform takes the manual work out of your security and compliance process and replaces it with continuous automation—whether you’re pursuing your first framework or managing a complex program.

Go to vanta.com/ruffin for $1,000 off Vanta today!!

More on Host Ruffin Mitchener:

https://beacons.ai/ruffin

About Brydge Club:

Brydge Club, hosted by Ruffin Mitchener, aims to bridge the $1.7 trillion financing gap for female founders. Every Sunday, the show features in-depth interviews with industry leaders and innovators, educating and empowering women in venture capital and entrepreneurship. Through insightful discussions, Brydge Club seeks to inspire listeners to break barriers and achieve success in the business world.

Welcome to the Brydge Club podcast! I'm your host, Ruffin, and today I'm joined by Kate McAndrew, Co-Founder and General Partner at Baukunst, a $100 million venture capital fund backing exceptional founders at the intersection of technology and design. Writing first checks of $500K to $2M at pre-seed, Kate was the first institutional investor in Bobbie, the first clean infant formula in the U.S. since the 1980s, and has spent over a decade backing founders long before anyone else believed.

Kate is an "accidental VC" who broke into the industry without an MBA, management consulting, or a finance pedigree. She got her first taste of investing while volunteering at a Habitat for Humanity job site. In this episode, she shares what she really looks for at pre-seed (hint: the team beats the idea every time), why she describes her job to her five-year-old as being a "professional fairy godmother," and the anti-portfolio deal that still haunts her, passing on Mirror before its $500M sale to Lululemon. Kate also opens up about building her fund in public after a year of PR got her nowhere, how short-form video became her secret weapon for deal flow and LP relationships, her take on the "SaaS is dead" and hardware hype cycles, and why she's moving her own workflow toward more values-aligned tools. We close with rapid fire on killing imposter syndrome, the visioning exercise that changed how she shows up, and the legacy she wants to leave for the next generation of women.

This episode is brought to you by Vanta. Vanta's Agentic Trust Platform takes the manual work out of your security and compliance process and replaces it with continuous automation—whether you’re pursuing your first framework or managing a complex program.

Go to vanta.com/ruffin for $1,000 off Vanta today!!

More on Kate McAndrew:


LinkedIn: https://www.linkedin.com/in/kateprestonmcandrew

Instagram: https://www.instagram.com/kate__mcandrew

TikTok: https://www.tiktok.com/@kate_mcandrew


Baukunst: https://baukunst.co/

More on Host Ruffin Mitchener:


https://beacons.ai/ruffin

About Brydge Club:


Brydge Club, hosted by Ruffin Mitchener, aims to bridge the $1.7 trillion financing gap for female founders. Every Wednesday, the show features in-depth interviews with industry leaders and innovators, educating and empowering women in venture capital and entrepreneurship. Through insightful discussions, Brydge Club seeks to inspire listeners to break barriers and achieve success in the business world.