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The Marketing Play That Got Millions to Finally Write a Will
Why Humor Is the Secret Weapon in Fintech Marketing...
What if the most effective way to get people to do the thing they have been avoiding is to make them laugh first?
In this episode, Roland sits down with Trust & Will CEO Cody Barbo to unpack how one fintech company took one of life’s most serious and uncomfortable topics, estate planning, and turned it into a high-performing, humor-driven growth engine.
From viral commercials and memorable characters to a brand strategy built on being approachable instead of intimidating, Trust & Will is proving that humor is not just a creative choice. It is a conversion strategy.
We break down:
•Why laughter creates trust faster than logic
•How Trust & Will built a category-defining brand in a space with no clear leader
•The role of partnerships with banks and fintechs in driving massive distribution
•Why giving away wills for free can actually increase AUM and retention
•How AI is reshaping the future of estate planning and what it means for fintech
•The behind-the-scenes startup grind, including printing thousands of wills in a coworking space
If you are building in fintech, marketing to consumers, or trying to stand out in a “boring” category, this is a masterclass in turning tone into traction.
Timestamps
00:00 – Intro and how Trust & Will’s ads first caught attention
00:37 – Making estate planning funny (yes, really)
01:49 – Why humor works in a traditionally serious category
02:34 – The origin of their marketing strategy
04:40 – Super Bowl ambitions and brand positioning
05:26 – Why banks and fintechs are key partners
08:40 – Estate planning as a retention and AUM strategy
10:34 – The power of co-branded distribution
14:14 – The origin story of “Trust & Will”
16:32 – Early startup days and finding product-market fit
20:34 – Scrappy operations (the “unlimited printing” hack)
21:56 – AI’s impact on the business
23:51 – Rebuilding the company AI-first
25:36 – Will creation in the age of AI
28:39 – Navigating compliance with financial institutions
29:47 – The surprisingly tricky question: who gets the kids?
TL;DR: In fintech, the brands that win are not always the most serious. They are the most memorable. And sometimes, the shortest distance between a customer and action is a well-timed joke.
Want to work with Propagate Fintech? Fill out a contact form at www.propagatefintech.com
View all episodes
By Roland HowardWhy Humor Is the Secret Weapon in Fintech Marketing...
What if the most effective way to get people to do the thing they have been avoiding is to make them laugh first?
In this episode, Roland sits down with Trust & Will CEO Cody Barbo to unpack how one fintech company took one of life’s most serious and uncomfortable topics, estate planning, and turned it into a high-performing, humor-driven growth engine.
From viral commercials and memorable characters to a brand strategy built on being approachable instead of intimidating, Trust & Will is proving that humor is not just a creative choice. It is a conversion strategy.
We break down:
•Why laughter creates trust faster than logic
•How Trust & Will built a category-defining brand in a space with no clear leader
•The role of partnerships with banks and fintechs in driving massive distribution
•Why giving away wills for free can actually increase AUM and retention
•How AI is reshaping the future of estate planning and what it means for fintech
•The behind-the-scenes startup grind, including printing thousands of wills in a coworking space
If you are building in fintech, marketing to consumers, or trying to stand out in a “boring” category, this is a masterclass in turning tone into traction.
Timestamps
00:00 – Intro and how Trust & Will’s ads first caught attention
00:37 – Making estate planning funny (yes, really)
01:49 – Why humor works in a traditionally serious category
02:34 – The origin of their marketing strategy
04:40 – Super Bowl ambitions and brand positioning
05:26 – Why banks and fintechs are key partners
08:40 – Estate planning as a retention and AUM strategy
10:34 – The power of co-branded distribution
14:14 – The origin story of “Trust & Will”
16:32 – Early startup days and finding product-market fit
20:34 – Scrappy operations (the “unlimited printing” hack)
21:56 – AI’s impact on the business
23:51 – Rebuilding the company AI-first
25:36 – Will creation in the age of AI
28:39 – Navigating compliance with financial institutions
29:47 – The surprisingly tricky question: who gets the kids?
TL;DR: In fintech, the brands that win are not always the most serious. They are the most memorable. And sometimes, the shortest distance between a customer and action is a well-timed joke.
Want to work with Propagate Fintech? Fill out a contact form at www.propagatefintech.com