Some of the world's biggest industries sell products that we all need...but don't want to think about. That's what drew Jennifer Fitzgerald to insurance: she wanted to help people understand the often bewildering world of protecting themselves in case of emergencies.

In 2013, she and her partner Francois de Lame left their stable and lucrative consulting jobs to create Policygenius, an online marketplace for insurance that lets consumers compare rates and learn everything they need to know to make informed decisions about their financial future.

At the beginning, Jennifer couldn't convince investors to take a chance on the company, and faced rejection after rejection as she tried to hold on to a handful of customers. But by building a relationship with the financial blogging community—and leaning in to a few well-placed financial technology puns—Policygenius got a foot in the door.

By 2020, Jennifer and her team had raised over $100 million, and the company now has more than 30 million users.

Show Notes:

2:44 - Intro
6:35 - Jennifer’s childhood
9:50 - College
10:48 - Going into the Peace Corps
15:30 - Getting a job at the world bank
16:33 - Working for McKinsey Consulting
18:26 - Starting in insurance
22:08 - Thinking about improving insurance
25:48 - The idea
30:26 - Quitting McKinsey
34:04 - Focusing on disability insurance
38:00 - Generating customers
40:43 - Trying to raise money from investors
47:28 - Figuring out a new way to raise money
51:43 - Launching the company
53:12 - Changing the name
54:29 - Getting attention
56:16 - The content
60:37 - Getting featured in the New York Times
63:22 - Having to raise money again
65:43 - Competitors
67:40 - Rolling out other products
68:30 - Life insurance
70:38 - How to sell something that isn’t sexy
72:30 - Becoming a big player in insurance
76:01 - The future of the company
78:15 - Reflecting
80:00 - Luck vs. hard work
80:55 - Stand-up Comedy

Selected links:

Policygenius
Jennifer Fitzgerald
Michelin Guide
Hubspot.com
Intothegloss
Expedia
Francois de Lame
Bluefield, West Virginia
Peace Corps
Santa Barbara, Honduras
The World Bank
McKinsey & Company Consulting
The Affordable Care Act
The Lean Startup - Eric Ries
Disability insurance
Zenefits
Fincon
Policygenius New York Times feature