Breaking Precedent

What does it take to walk away from a business that’s working, because you know it will never be great?

On Breaking Precedent, Leah Solivan talks with Jean-Denis Greze, co-founder of Town, about a path that took more than a decade to find. He started coding as a teenager to play dial-up BBS games for him while he was at school, moved to Florida in eighth grade as a French kid still learning English, and went from engineering to grad school to Harvard Law. He recounts the “terrible week” of 2008 deal work that made him quit law, how a Hack Week visit pulled him to Dropbox, and what he learned watching Dropbox and Plaid scale before becoming a founder himself.

Jean-Denis explains why he and his co-founder, Tony, shut down an AI tax business that was approaching $1 million in revenue: it looked like an “okay outcome” for the founders and a bad one for the team. They pivoted to Town, a personal AI assistant that learns how you work and offers to automate it. He breaks down Town’s “anti-FDE” approach, why the brand is deliberately whimsical, why Town would rather say it can’t do something than make things up, why he thinks AI pessimism is misplaced, and why he’s most excited about AI in drug discovery and the physical world.

Key Insights

• You can just do things. You can uproot, quit, and start over, even when it isn’t the obvious career move.
• Put a decision point on the calendar and be honest about whether you’re climbing the wrong hill.
• The worst outcome isn’t failure. It’s the company stuck in between that can’t hire, raise, or exit.
• Experience makes it easier to say no. The challenge is keeping the energy of your 20-year-old self.
• Mainstream users don’t buy capabilities. They want something simple they can trust.
• AI earns trust when it explains what it did and makes mistakes easy to undo.
• Building a better future starts with believing we can.

Timestamps

00:00 Welcome and How Leah Uses Town
 01:45 Icebreaker: The Moves That Shaped Him
 06:30 A French Kid in Eighth-Grade Florida
 10:25 Seeing Every Side of an Argument
 13:05 Coding Since the BBS Days
 16:30 From Engineer to Harvard Law
 18:40 The Terrible Week That Ended His Law Career
 22:40 Finding His Way Back to Code
 24:00 What Law Taught a Founder
 26:45 Why Become a Founder
 30:25 What Experience Teaches, and What It Costs
 33:50 Killing a Tax Business That Was Working
 40:45 Town: An AI Assistant That Learns You
 41:15 The Anti-FDE Approach
 47:35 Why the Brand Is Whimsical
 50:10 Trust: Conservative by Design
 54:30 The AI Belief He Thinks Is Wrong
 57:10 When Townies Work Together
 58:55 The Biggest Missed Opportunity
 01:00:05 Competition and Margins in AI
 01:02:20 Building in the Physical World
 01:04:00 The Precedent to Break
 01:05:45 Closing Reflections

Thank you to our Precedent Breaking Partners!

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Squared Away: gosquaredaway.com/breakingprecedent?utm_source=breakingprecedent&utm_medium=podcast&utm_campaign=breakingprecedent&utm_content=podcast

Leah Solivan is the host of Breaking Precedent, a podcast that explores the stories of innovators who are pushing societal boundaries and setting new precedents in their fields. Leah Solivan is General Partner at Fuel Capital, where she invests in early-stage companies across consumer technology, hardware, education, marketplaces, and retail. Leah Solivan has 15 years of experience building and creating technology products that have reached millions of people around the globe. She started her career at IBM as an engineer in the software group, working on Lotus Notes and Domino. In 2008, Leah Solivan founded TaskRabbit, the leading on-demand service marketplace in the world.

Connect with Leah Solivan:

Website: breakingprecedent.com
Instagram: https://www.instagram.com/leah_solivan/
X: https://twitter.com/labunleashed?lang=en

Why do we accept broken systems as normal?

On Breaking Precedent, Leah Solivan talks with Heather Fernandez, co-founder of Solv, about a career spent questioning the systems everyone else accepts. It started in elementary school, when she asked the monsignor at her church why she couldn't be an altar girl. The daughter of immigrant parents, Heather bought a one-way ticket to Washington, DC after graduating from Cal and landed her first job as deputy press secretary for a freshman congressman from Arizona, where she learned that even the people with the most power are figuring it out as they go. From there she moved into tech PR, Stanford Business School and Morgan Stanley before joining Trulia when it was 12 people in a room. Over ten years she went from marketing to running sales to owning Trulia's core B2B business, through its $2.5 billion acquisition by Zillow.

Heather explains why she walked away from the obvious next move to start Solv as a healthcare outsider, built around three simple questions: Where should I go? When can I be seen? How much will it cost? She and Leah dig into urgent care as everyday healthcare for millions of Americans, why the industry was so unhelpful to newcomers, how naming users like Mary the mom and Faith at the front desk shaped the product, helping power COVID testing sites during the pandemic, and why she believes not knowing what care costs will soon seem absurd.

Key Insights

• Even the people with the most power are figuring it out as they go. Seeing that early takes away the intimidation.
• Startups let you try on hats no one else would hand you. Heather went from marketing to running sales by asking for the job.
• Equity changes who gets to take risks. Trulia's cap table is what let Heather start Solv, and why Solv opened its Captain Marvel SPV to women.
• In healthcare, start with a real problem you can solve and a clear path to expand it.
• You can't fix the patient experience without reducing friction for the front desk and the clinic.
• The next decade will reward the doers.

Timestamps

00:00 Cold Open
 00:43 Welcome
 02:08 The Altar Girl Question
 03:25 Candor and Immigrant Grit
 07:45 A One-Way Ticket to DC
 11:10 Everyone Is Figuring It Out
 11:20 “Even the people with the most power are figuring it out as they go.” — Heather Fernandez
15:28 From Politics to Tech
19:05 Finding Trulia
22:45 From Marketing to Running Sales
26:05 Equity and the Captain Marvel SPV
27:25 Why Healthcare
32:35 Where, When, and How Much
35:10 Urgent Care Is Everyday Healthcare
38:28 Proximity to Power
41:20 Start Small, Create a Wave
43:25 Complexity as a Moat
46:45 Mary, Faith, and Olivia
50:50 COVID Stress Test
54:15 What Stuck After COVID
56:25 Price Transparency Is Next: Zero or $800
59:25 Why She's an AI Optimist
01:04:10 Misconceptions About Scale
01:05:32 The Next Decade Belongs to Doers
01:07:55 Rapid Fire
01:08:55 Stop Waiting for Permission
01:09:55 Closing

Resources Mentioned

Solv: https://www.solvhealth.com/
Heather Fernandez on LinkedIn: https://www.linkedin.com/in/heatherfernandez

Thank you to our Precedent Breaking Partners!

Squared Away: gosquaredaway.com/breakingprecedent?utm_source=breakingprecedent&utm_medium=podcast&utm_campaign=breakingprecedent&utm_content=podcast
TaskRabbit: taskrabbit.com/?utm_source=breakingprecedent&utm_medium=podcast&utm_campaign=breakingprecedent&utm_content=podcast
Justworks: justworks.com/?utm_source=breakingprecedent&utm_medium=podcast&utm_campaign=breakingprecedent&utm_content=podcast

Leah Solivan is the host of Breaking Precedent, a podcast that explores the stories of innovators who are pushing societal boundaries and setting new precedents in their fields. Leah Solivan is General Partner at Fuel Capital, where she invests in early-stage companies across consumer technology, hardware, education, marketplaces, and retail. Leah Solivan has 15 years of experience building and creating technology products that have reached millions of people around the globe. She started her career at IBM as an engineer in the software group, working on Lotus Notes and Domino. In 2008, Leah Solivan founded TaskRabbit, the leading on-demand service marketplace in the world.

Connect with Leah Solivan:

Website: breakingprecedent.com
Instagram: https://www.instagram.com/leah_solivan/
X: https://twitter.com/labunleashed?lang=en

What happens when the kid who scored his first basket on his own team becomes an NBA champion, and then has to start over again?

On Breaking Precedent, Leah Solivan talks with former Golden State Warrior Festus Ezeli about a journey nobody could have scripted. Festus grew up in Benin City, Nigeria, finished high school at 14, and moved alone to Yuba City, California, to live with his uncle and chase a dream of becoming a doctor. Strangers kept asking the 6'4" teenager if he played basketball. He didn't, until he scored his first basket on his own team and got cut from his high school team. With a mentor who believed in him before he believed in himself, he embraced being a beginner, turned down Harvard for Vanderbilt, switched from pre-med to economics, and became a first-round NBA draft pick. He shares what he learned from Steph Curry's early-morning work ethic and a Warriors team where nobody cared who got the glory.

Then came the injury: early retirement and six months in a wheelchair, a year after playing in the NBA Finals. Festus opens up about his mom's lesson on moving mountains, finding his voice again in media and storytelling, and the work he's building now: schools in Nigeria and Sacramento, leadership and basketball camps in Africa, Festus Feasts and The Vision Table supporting local restaurants, and his push to rewrite what life after sports can look like.

Key Insights

• Being a beginner can be a superpower when it makes you listen and do whatever it takes to improve.
• Sometimes you have to believe in someone else's belief in you until yours kicks in.
• Greatness lives in small daily habits that nobody sees.
• It's amazing what can be accomplished when nobody cares who gets the glory.
• A career-ending injury doesn't have to be a life-ending one. The skills transfer.
• Privilege comes with a responsibility to create opportunity for others.

Timestamps

00:00 Cold Open: “God Gave You Your Mountains”
 01:10 Leah’s Introduction
 02:40 Welcome and Reunion
 03:10 Ballet Night Backstage
 04:20 Bread and Tea in Nigeria
 05:55 Growing Up in Benin City
 08:15 The Tortoise and the Hare
 09:40 The Meaning of Ifeanyichukwu
 11:10 Moving to America Alone at 14
 15:40 “Do You Play Basketball?”
 17:20 Scoring on His Own Team
 18:40 The Mentor Who Believed First
 20:40 Being a Beginner as a Superpower
 22:40 Turning Down Harvard for Vanderbilt
 24:45 Choosing Basketball over Medicine
 26:40 Two-Time Most Improved
 27:45 Trusting Your Intuition
 28:40 Steph Curry's Work Ethic
 31:05 Nobody Cares Who Gets the Glory
 32:00 Injury and Early Retirement
 32:55 Finding Joy in Storytelling
 36:15 Six Months in a Wheelchair
 37:10 “This life is short, and it's our job to take advantage of the moment while it's here.” — Festus Ezeli
38:50 Mom's Mountain Lesson
40:55 A Podcast About Comebacks
41:45 Schools and Camps
44:50 The Kid Who Showed Up Early
47:10 The Ripple Effect
49:25 Festus Feasts
52:25 The Vision Table
54:15 Rewriting Life After Sports
54:50 Why Kids' Education Is Urgent
55:35 Women's Sports
58:30 Legacy and Final Takeaways

Thank you to our Precedent Breaking Partners!

Justworks: justworks.com/?utm_source=breakingprecedent&utm_medium=podcast&utm_campaign=breakingprecedent&utm_content=podcast
Squared Away: gosquaredaway.com/breakingprecedent?utm_source=breakingprecedent&utm_medium=podcast&utm_campaign=breakingprecedent&utm_content=podcast
TaskRabbit: taskrabbit.com/?utm_source=breakingprecedent&utm_medium=podcast&utm_campaign=breakingprecedent&utm_content=podcast

Leah Solivan is the host of Breaking Precedent, a podcast that explores the stories of innovators who are pushing societal boundaries and setting new precedents in their fields. Leah Solivan is General Partner at Fuel Capital, where she invests in early-stage companies across consumer technology, hardware, education, marketplaces, and retail. Leah Solivan has 15 years of experience building and creating technology products that have reached millions of people around the globe. She started her career at IBM as an engineer in the software group, working on Lotus Notes and Domino. In 2008, Leah Solivan founded TaskRabbit, the leading on-demand service marketplace in the world.

Connect with Leah Solivan:

Website: breakingprecedent.com
Instagram: https://www.instagram.com/leah_solivan/
X: https://twitter.com/labunleashed?lang=en

What does it take to quit your job, skip venture capital entirely, and build two seven-figure businesses on relationships alone?

On Breaking Precedent, Leah Solivan talks with Stephanie Cartin, co-founder of Socialfly and Entreprenista, about the day she and co-founder Courtney quit their jobs, May 4, 2012, after ten months of building a social media agency on nights and weekends. Stephanie traces the thread from performing as a child actress in the Washington, DC area, to a Disney Vacation Club presentation at age 11 that led her to Cornell's hotel school and a career at Marriott, to spotting social media's business potential as an early Facebook user. She explains how one networking group, mentor Carrie Kerpen, and the book Built to Sell shaped a fully bootstrapped, all-women agency that grew to seven figures without outside funding.

Stephanie then shares why she split from the agency in 2021 to build Entreprenista into a media company and membership community, the Entreprenista League, now 4,500 members strong, focused on connection, resources, and visibility. She and Leah dig into what still holds women founders back, alternative paths to capital, why AI is leveling the playing field for small businesses, and why she believes real human connection, and in-person community, is the opportunity AI can't replace.

Key Insights

• A calculated leap is different from a reckless one: Stephanie and Courtney built for ten months on the side and made a plan before quitting.
• Relationships compound. A contact from age 11, a friend's mom's old client, and one networking group opened nearly every early door.
• You don't need to be the smartest person in the room. Learn from people who have already built businesses, even in other industries.
• Bootstrapping is a real strategy. Most women-owned businesses are not venture-funded, and debt can work when it funds real growth.
• Build a sellable asset, not just a job for yourself.
• AI can level the playing field on operations, but it can't replace human connection.

Timestamps

00:00 Welcome To Breaking Precedent

00:47 Meet Leah And Stephanie

02:59 Broadway Dreams To Hospitality

05:01 Disney Spark And Cornell Path

07:09 Spotting Social Media Early

10:29 Gut Instinct And Trend Timing

11:40 Theater Skills In Business

13:39 Going All In On Socialfly

16:01 First Clients Through Networking

18:30 Bootstrapping And Women Led Agency

20:36 Mentorship With Carrie Kerpen

22:56 Selling Socialfly Tease

23:17 Building to Sell Mindset

24:49 Why EntrepreNista Started

25:47 Pandemic Pivot and Split

27:32 League Solves Founder Gaps

29:31 Writing a Credibility Book

32:13 What Still Holds Women Back

36:47 AI Tools and Human Connection

39:54 Future Vision and IRL Growth

43:38 Next Gen Rules to Break

45:52 Closing Reflections 

Resources Mentioned

Entreprenista: entreprenista.com

Thank you to our Precedent Breaking Partners!

TaskRabbit: taskrabbit.com

Justworks: justworks.com

Squared Away: gosquaredaway.com/breakingprecedent

Leah Solivan is the host of Breaking Precedent, a podcast that explores the stories of innovators who are pushing societal boundaries and setting new precedents in their fields. Leah Solivan is General Partner at Fuel Capital, where she invests in early-stage companies across consumer technology, hardware, education, marketplaces, and retail. Leah Solivan has 15 years of experience building and creating technology products that have reached millions of people around the globe. She started her career at IBM as an engineer in the software group, working on Lotus Notes and Domino. In 2008, Leah Solivan founded TaskRabbit, the leading on-demand service marketplace in the world.

Connect with Leah Solivan:

Website: breakingprecedent.com

Instagram: instagram.com/leah_solivan

X: twitter.com/labunleashed

How do you keep going when your biggest success comes with losing almost everything along the way?

On Breaking Precedent, Kass and Mike Lazerow discuss their book Shoveling Shit: A Love Story and what happens when entrepreneurship and marriage collide, especially while raising three kids. They recount their early entrepreneurial roots, meeting in the mid-’90s internet era, and building Golf.com. They sold it to Chipshot during their honeymoon period, lost access to everything when Chipshot ran out of money, then rebuilt and ultimately sold Golf.com to Time Warner amid Tiger Woods’ rise.

They describe starting Buddy Media in 2007 while juggling a newborn, scaling it, and selling to Salesforce for $745M, yet feeling strained, unhealthy, and disconnected afterward. Now investors, they outline their “Go Gauge” framework for evaluating ideas, argue there’s no perfect time to start, push back on bias against married co-founders, and emphasize embracing the “shoveling” reality while using AI to stay competitive.

Key Insights

• Entrepreneurship is less about avoiding failure and more about learning to keep moving when things fall apart.
• The hardest parts of building a company often happen in the messy middle, when uncertainty, sacrifice, and setbacks become part of the journey.
• Success can look very different behind the scenes, especially when professional achievements come with personal and family costs.
• Complementary strengths between partners can become a powerful advantage when building a company together.
• Setbacks can become turning points when entrepreneurs keep working through the problem instead of staying focused on what went wrong.
• There may never be a “right” time to take the leap.

Timestamps

00:00 Welcome 

02:49 On the Entrepreneurial Journey

07:24 Early Hustles And Roots

10:45 Mike Learns Freedom

13:17 Meeting In Web One

18:17 Golf Dot Com Crash

22:24 Shoveling And Lucky Breaks

26:03 Buddy Media Sacrifices

27:53 Credit And Co Founder Balance

31:42 Exit Aftermath Feelings

33:26 Health Wake Up Call

35:31 Writing The Real Story

36:52 From Founders To Investors

39:25 Go Gauge Framework

43:11 Messy Middle Mindset

44:55 AI As Operating System

48:33 Rethinking Venture Rules

51:09 Venture Capital Reset

55:12 Legacy And Precedent

59:57 Closing Thanks 

Resources Mentioned

Shoveling Shit: A Love Story: https://www.shovelingshit.com/

Golf.com: https://golf.com

Salesforce: https://www.salesforce.com

Warner Media: https://www.warnermedia.com

Thank you to our Precedent Breaking Partners!

Squared Away: gosquaredaway.com/breakingprecedent?utm_source=breakingprecedent&utm_medium=podcast&utm_campaign=breakingprecedent&utm_content=podcast

TaskRabbit: taskrabbit.com/?utm_source=breakingprecedent&utm_medium=podcast&utm_campaign=breakingprecedent&utm_content=podcast

Justworks: justworks.com/?utm_source=breakingprecedent&utm_medium=podcast&utm_campaign=breakingprecedent&utm_content=podcast

Leah Solivan is the host of Breaking Precedent, a podcast that explores the stories of innovators who are pushing societal boundaries and setting new precedents in their fields. Leah Solivan is General Partner at Fuel Capital, where she invests in early-stage companies across consumer technology, hardware, education, marketplaces, and retail. Leah Solivan has 15 years of experience building and creating technology products that have reached millions of people around the globe. She started her career at IBM as an engineer in the software group, working on Lotus Notes and Domino. In 2008, Leah Solivan founded TaskRabbit, the leading on-demand service marketplace in the world.

Connect with Leah Solivan:

Website: breakingprecedent.com/

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

X: https://twitter.com/labunleashed?lang=en

What happens when a $648 billion market goes uncounted, and who decided it wasn't worth measuring in the first place?

This episode follows Erin Harkless Moore from the breakfast table in San Antonio, through Goldman Sachs, Cambridge Associates, and Princeton's endowment, to Pivotal, the organization founded by Melinda French Gates, where she builds an investment program aimed at the people and markets capital has overlooked. It's a conversation about who gets funded, who gets to decide, and what changes when you start measuring what finance has ignored.

Leah Solivan interviews Erin about starting her career in a Goldman Sachs group with no female partners, earning the CFA so no one could question her technical credibility, and cold-emailing Harvard Business School alumni to find her way to the allocator side of the table. She shares the index card her husband pushed her to write, a single line about changing how capital is allocated and who is in the room, and how it led to a job she half-thought was a prank, interviewing virtually as Seattle became an early COVID epicenter.

Erin explains why reframing the bar isn't the same as lowering it, using the example of GP commitment requirements that can screen out fund managers who don't come from wealth. She walks through Pivotal's approach of using investing, philanthropy, and advocacy together, how DEI headwinds are showing up in fundraising right now, what she has learned from watching Melinda French Gates prepare for every meeting, and where she sees the next overlooked markets, from women's health to women's sports.

She closes with what she'd write on the index card for the next generation of women building where capital hasn't looked yet.

Key Insights

• Reframing the bar isn't lowering it. It's asking whether you're measuring the risk you actually care about.

• A market nobody has measured is easy to dismiss. Sizing it can make it undeniable.

• Diligence rules like large GP commitments can screen out strong managers who didn't start with wealth.

• Writing a one-line purpose down makes it easier to say no to the wrong opportunity.

• No single tool moves a big problem. Investing, philanthropy, and policy work better together.

• When data alone doesn't change minds, a better story often has to.

• Conviction backed by homework and data is what carries you through the doubt.

Timestamps

00:00 Welcome to Breaking Precedent

02:09 Her Grandma’s Index Card

04:20 San Antonio Roots

08:15 Breakfast and Family Rituals

12:40 Math to Wall Street

17:37 Women in Finance Reality Check

22:29 Writing the Career Index Card

26:35 The Call From Pivotal

29:37 Betting on the Care Economy

31:21 Choosing the Leap

34:30 Sizing the Care Economy

37:33 Reframing the Bar

39:41 Living the Thesis

42:16 All Tools Strategy

45:36 DEI Headwinds Returns

49:41 Lessons From Melinda

51:51 Next Invisible Markets

55:21 Breaking Precedent Legacy

57:13 Conviction for Builders

Resources Mentioned

Pivotal Ventures: https://www.pivotalventures.org

Magnify Ventures: https://www.magnifyventures.com

Cambridge Associates: https://www.cambridgeassociates.com

Thank you to our Precedent Breaking Partners!

Justworks: justworks.com/?utm_source=breakingprecedent&utm_medium=podcast&utm_campaign=breakingprecedent&utm_content=podcast

Squared Away: gosquaredaway.com/breakingprecedent?utm_source=breakingprecedent&utm_medium=podcast&utm_campaign=breakingprecedent&utm_content=podcast

TaskRabbit: taskrabbit.com/?utm_source=breakingprecedent&utm_medium=podcast&utm_campaign=breakingprecedent&utm_content=podcast

Leah Solivan is the host of Breaking Precedent, a podcast that explores the stories of innovators who are pushing societal boundaries and setting new precedents in their fields. Leah Solivan is General Partner at Fuel Capital, where she invests in early-stage companies across consumer technology, hardware, education, marketplaces, and retail. Leah Solivan has 15 years of experience building and creating technology products that have reached millions of people around the globe. She started her career at IBM as an engineer in the software group, working on Lotus Notes and Domino. In 2008, Leah Solivan founded TaskRabbit, the leading on-demand service marketplace in the world.

Connect with Leah Solivan:

Website: breakingprecedent.com/

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

X: https://twitter.com/labunleashed?lang=en

What happens when you turn down an early job at Netflix, back when it was still just an idea about mailing DVDs, and then spend the next decade proving that work doesn't have to happen in an office?

This episode follows Gary Swart from running a parts middleman business in New Jersey to leading oDesk for nearly ten years, the company that later merged with Elance to become Upwork. He explains the criteria he now uses for big career decisions, why weighing the people differently might have sent him to Netflix, and how oDesk made hiring talent anywhere feel normal long before the pandemic forced the issue.

Leah Solivan interviews Gary Swart, now an investor at Polaris Partners, about the forks in the road that shaped his career. Swart recounts auditioning for a sales job at Reed Hastings' Pure Software without knowing how to use a mouse, the "battlefield promotions" that followed, and leaving IBM for a startup so low on cash that he refused to mislead a customer about whether it would survive. He explains how a Sigma Partners investor sent him to oDesk, where he went from COO to CEO within weeks and had to pick between staffing firm and marketplace.

Swart shares the frameworks he still leans on: reversible versus irreversible decisions, people, PowerPoint and Excel for evaluating founders, and hiring for personal characteristics before skills. He walks through cutting oDesk's take rate from 30% to 10%, guaranteeing work quality, and Reed Hastings' warning that 90% of CEOs are under-focused. He also looks ahead at a future of work that is atomized, more specialized, and augmented by AI, including the app he built himself in an afternoon.

And at an age when many of his peers are winding down, he explains why he's still looking for uncomfortable positions, starting with writing a book.

Key Insights

• If a decision is reversible, make it. Waiting for certainty usually costs more than being wrong.

• The people matter more than the title. Swart says he would take a demotion to work with the smartest people he knows.

• Two directions is no direction. A company pulled between two business models has to declare a major.

• Customers who won't recommend you because you're their "secret weapon" are telling you something good.

• Short-term revenue pain, like cutting a take rate, can buy a position competitors can't undercut.

• Hire for personal characteristics first, then motivation, skills, and domain knowledge last.

• Most founders are under-focused. The current market is usually big enough.

Timestamps

00:00 Welcome to Breaking Precedent

02:35 Turning Down Netflix

06:37 Career Decision Framework

09:51 Early Hustle in Manufacturing

11:30 Moving West Into Tech

13:16 Pure Software Baptism

16:19 Frameworks Built From Mistakes

21:50 Finding oDesk and CEO Leap

23:54 Marketplace Versus Staffing

26:38 Remote Work Unlock and Impact

31:59 Tailwinds Behind Remote Work

35:01 Geography and Global Opportunity

36:28 COVID Validation and E Commerce

37:24 Remote Work After COVID

38:49 AI Atomizes Jobs

39:53 Prototyping With AI

41:07 How Investors Decide

43:20 Scrappy Before Scaling

46:07 Pricing Take Rate Shift

49:10 Fixing Marketplace Trust

51:17 Hiring For Traits First

53:52 Backchannel References

55:57 Founder Mistakes Focus

59:26 On Demand Work Future

01:03:06 Breaking Personal Precedent

01:08:12 Closing Reflections

Resources Mentioned

Upwork: https://www.upwork.com

Polaris Partners: https://www.polarispartners.com

Thank you to our Precedent Breaking Partners!

TaskRabbit: taskrabbit.com/?utm_source=breakingprecedent&utm_medium=podcast&utm_campaign=breakingprecedent&utm_content=podcast

Justworks: justworks.com/?utm_source=breakingprecedent&utm_medium=podcast&utm_campaign=breakingprecedent&utm_content=podcast

Squared Away: gosquaredaway.com/breakingprecedent?utm_source=breakingprecedent&utm_medium=podcast&utm_campaign=breakingprecedent&utm_content=podcast

Leah Solivan is the host of Breaking Precedent, a podcast that explores the stories of innovators who are pushing societal boundaries and setting new precedents in their fields. Leah Solivan is General Partner at Fuel Capital, where she invests in early-stage companies across consumer technology, hardware, education, marketplaces, and retail. Leah Solivan has 15 years of experience building and creating technology products that have reached millions of people around the globe. She started her career at IBM as an engineer in the software group, working on Lotus Notes and Domino. In 2008, Leah Solivan founded TaskRabbit, the leading on-demand service marketplace in the world.

Connect with Leah Solivan:

Website: breakingprecedent.com/

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

X: https://twitter.com/labunleashed?lang=en

What does it take to keep building a workwear brand for a decade after a top VC tells you, in writing, that utility doesn't belong in women's clothing?

This episode traces Sali Christeson's path from a childhood split between a South Carolina farm and her father's rug shop in Istanbul's bazaars to building Argent, the workwear brand she's run for a decade, showing how a VC's rejection, a crisis handled in real time, and a refusal to accept easy either/or choices became the foundation for a company built on her own terms.

Leah Solivan interviews Argent founder and CEO Sali Christeson about building a workwear company outside the traditional venture path after a top-tier VC rejected her pitch in writing with the line that would become fuel for everything that followed: utility doesn't belong in women's clothing. Christeson recounts a childhood shaped by a mother who insisted she build her own career and a father who ran a rug shop in Istanbul's bazaars, an MBA and a rotational program at Cisco that exposed her to gender inequity in real time, and the decision to quit and start a fashion company with no fashion background.

She describes building her own cap table out of values-aligned investors rather than chasing the roughly two percent of venture funding that goes to female founders, being eight months pregnant when COVID hit in March 2020 and closing all four Argent stores within days, and turning a warehouse of unsold hot pink suits into a partnership with Supermajority that sold out in twenty-four hours. Christeson also discusses the decision to pull a planned partnership with Planned Parenthood, finding the right creative partner after years of holding on too tightly, and what a new generation of Gen Z customers is teaching her about Argent's next chapter.

Ten years in, she gives her most honest answer yet to whether anything has actually gotten better for women at work.

Key Insights

• A rejection can be the clearest signal you're onto something: a VC calling an idea overdone often means the market is real and nobody has solved it yet.

• Building a brand as a movement, not just a product, is what keeps customers coming back for a decade instead of a season.

• Being chronically underfunded can sharpen a business by forcing more disciplined decisions than a well-capitalized competitor has to make.

• Fast, decisive action under pressure, like closing every store within days of a crisis, protects the business you're trying to save.

• Timing and story can move product faster than the product itself.

• Knowing when to walk away from a partnership that no longer fits matters as much as knowing when to commit to one.

• Ten years in, the honest answer to "have things gotten better" is rarely a simple yes or no.

Timestamps

00:00 Welcome to Breaking Precedent

00:17 Meet Leah And Sally

02:20 Roots And Style

03:44 Work Ethic And Early Hustles

06:10 Confidence Empathy And Ambition

09:32 Structured Path To Founder

12:18 Cisco Sparks The Idea

15:15 Quitting To Build Argent

17:18 VC Bias And Pocketgate

19:31 Rewriting Fundraising Rules

22:18 World Building The Brand

26:07 Scrappy Funding Advantage

28:50 COVID Shutdown Decisions

31:53 Viral Pink Suit Campaign

33:16 Finding Creative Partner

35:07 Doubling Down Mission

39:01 Gen Z And Community

40:46 Authenticity Over Tradeoffs

42:53 Advice For Women Founders

44:35 Money And Investing Power

46:27 Messy Middle Survival

49:46 Closing Reflections

Resources Mentioned

Supermajority: https://supermajority.com?utm_source

Planned Parenthood: https://www.plannedparenthood.org?utm_source

Thank you to our Precedent Breaking Partners!

TaskRabbit: https://taskrabbit.com/?utm_source=breakingprecedent&utm_medium=podcast&utm_campaign=breakingprecedent&utm_content=podcast

Justworks: https://justworks.com/?utm_source=breakingprecedent&utm_medium=podcast&utm_campaign=breakingprecedent&utm_content=podcast

Squared Away: https://gosquaredaway.com/breakingprecedent?utm_source=breakingprecedent&utm_medium=podcast&utm_campaign=breakingprecedent&utm_content=podcast

Leah Solivan is the host of Breaking Precedent, a podcast that explores the stories of innovators who are pushing societal boundaries and setting new precedents in their fields. Leah Solivan is General Partner at Fuel Capital, where she invests in early-stage companies across consumer technology, hardware, education, marketplaces, and retail. Leah Solivan has 15 years of experience building and creating technology products that have reached millions of people around the globe. She started her career at IBM as an engineer in the software group, working on Lotus Notes and Domino. In 2008, Leah Solivan founded TaskRabbit, the leading on-demand service marketplace in the world.

Connect with Leah Solivan:

Website: breakingprecedent.com/

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

X: https://twitter.com/labunleashed?lang=en

What did Anne Wojcicki see in healthcare that made her leave Wall Street and risk challenging an entire industry to put power back in patients’ hands? 

Welcome to the brand new season of Breaking Precedent where Leah Solivan interviews 23andMe founder Anne Wojcicki about breaking medical “gatekeeping” by giving consumers direct access to their genetic information and using that data to drive research and prevention. Solivan shares learning she did not carry BRCA2 while pregnant, and Wojcicki recounts motivations shaped by her mother’s fierce self-advocacy, a Stanford community of inquiry, and an immigrant family history that emphasized purpose over materialism. After Yale (biology and a year of hockey) and a Wall Street career that exposed ethical problems in healthcare, Wojcicki drew inspiration from HIV patient advocates to build a platform for people to advocate for themselves. 

She describes co-founding 23andMe in 2006 with Linda Avey and Paul Cusenza, early public skepticism, the unexpected power of ancestry, medical resistance to broad genetic testing, and how COVID-era telehealth and AI enable new prevention tools. Wojcicki explains buying 23andMe back via a nonprofit to better align incentives, scale research access, and build a subscription product integrating genetics with medical records, self-report data, wearables, and updated insights for personalized risk prediction and guidance.

Key Insights

• Questioning the status quo can become a foundation for leadership and innovation.

• Unexpected experiences can reveal what truly matters and shape a person’s direction.

• Advocacy can inspire people to create systems that empower others to speak for themselves.

• Different perspectives can come together to create a more powerful and holistic idea.

• Breaking precedent often requires challenging assumptions that others accept as normal.

• Innovation requires understanding how people actually respond, not just what founders expect.

• Responsible innovation means considering the ethical consequences of new technology.

• Personal values can become the foundation of a larger mission to empower people and improve systems.

• Purpose becomes more powerful when it extends beyond personal success and creates impact for others. 

Timestamps:

00:00 Welcome to Breaking Precedent 

00:42 Meet Anne Wojcicki

01:58 BRCA Midnight Results

03:27 Ashkenazi Screening Gaps

04:32 Question Everything

06:12 Mom the Advocate

09:17 Rebel Teacher Mindset

12:05 Debate and Free Thinking

14:46 Stanford Community Roots

16:52 Immigrant Purpose Drive

19:42 Yale Hockey and Culture Shock

24:25 Wall Street Detour

26:13 Healthcare Ethics Wakeup

28:21 HIV Activists Inspire

31:24 Founding 23andMe

34:55 Selling Genetics DTC

38:36 Prevention Meets AI

41:45 Nonprofit Mission Shift

43:50 Drug Discovery Reality

46:31 Paying for Prevention

53:00 Closing Reflections

Resources

HIV Activist Movement: https://www.hiv.gov?utm_source=chatgpt.com 

The Michael J. Fox Foundation: https://www.michaeljfox.org?utm_source=chatgpt.com 

23andMe Research Institute: https://www.23andme.org/about/?utm_source=chatgpt.com 

Leah Solivan is the host of Breaking Precedent, a podcast that explores the stories of innovators who are pushing societal boundaries and setting new precedents in their fields. Leah Solivan is General Partner at Fuel Capital, where she invests in early-stage companies across consumer technology, hardware, education, marketplaces, and retail. Leah Solivan has 15 years of experience building and creating technology products that have reached millions of people around the globe. She started her career at IBM as an engineer in the software group, working on Lotus Notes and Domino. In 2008, Leah Solivan founded TaskRabbit, the leading on-demand service marketplace in the world.

Thank you to our Precedent Breaking Partners!
TaskRabbit: taskrabbit.com/?utm_source=breakingprecedent&utm_medium=podcast&utm_campaign=breakingprecedent&utm_content=podcast

Justworks: justworks.com/?utm_source=breakingprecedent&utm_medium=podcast&utm_campaign=breakingprecedent&utm_content=podcast 

Squared Away: gosquaredaway.com/breakingprecedent?utm_source=breakingprecedent&utm_medium=podcast&utm_campaign=breakingprecedent&utm_content=podcast

Connect with Leah Solivan:

Website: breakingprecedent.com/ 

Instagram: @leah_solivan

X: @labunleashed

Season 3 of Breaking Precedent is here.

This season, Leah sits down with founders, athletes, and builders who refused to accept the world as it was handed to them. From a card game that turns into hard business questions, to rewriting the script for life after sports, to reimagining what healthcare could look like if someone actually believed in you — these are conversations about challenging inherited beliefs, collecting skills, and taking your future into your own hands.

Welcome to Season 3.

Connect with Leah Solivan
Website: breakingprecedent.com
Instagram: @leah_solivan
X: @labunleashed