How I Built This with Guy Raz

Today’s callers: Jess from Washington seeks counsel on structuring a collaboration between her sympathy cards company and a pet products brand. Then, Caroline from Colorado wonders if she should build an in-house production team or outsource manufacturing for her decorative garland company. And Sayuri from California is looking to drive sales of her Japanese tatami mats through a unique approach to yoga practice.
Plus, Alexa shares how Paperless Post is responding to advancements in AI and the prevalence of post-pandemic loneliness.
Thank you to the founders of Five Dot Post, The Creative Garland Company, and Sumo Yoga for being a part of our show.
If you’d like to be featured on a future Advice Line episode—where Guy and former show guests take questions from early-stage founders—leave us a one-minute message that tells us about your business and a specific question you’d like answered. Send a voice memo to [email protected] or call 1-800-433-1298.
And be sure to listen to Paperless Post as told by Alexa and her brother James on the show in 2024.
This episode was produced by Rommel Wood with music by Ramtin Arablouei. It was edited by John Isabella. Our audio engineers were Debbie Daughtry and Cena Loffredo.
You can follow HIBT on X & Instagram and sign up for Guy's free newsletter at guyraz.com and on Substack.
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Most entrepreneurs think the hardest part of building a company is the product.
For Jim McKelvey — co-founder of Square — the hardest part was the system around the product.
Because Square wasn’t just competing with other startups …
It was competing with regulations, middlemen, entrenched networks, and monopolies designed to keep outsiders out.
In this episode, Jim shares the mindset and tactics that helped Square go from a tiny card reader that processed credit card payments … to a company—now known as Block— that generates over $10 billion in gross profit.
What You’ll Learn:
Why the market is often “locked” on purpose
How a simple hack can solve a seemingly complex problem
How candor can sway investors more than confidence
How Square survived by building something Amazon couldn’t copy
Timestamps:
00:12:26 – Engineering and art: Balancing an IBM job with glassblowing
00:15:46 – The family trauma that rewired Jim
00:36:26 – Losing a $2,000 sale — the moment Square was born
00:43:06 – Breaking into the credit card club: “We were violating 17 rules”
00:48:31 – The headphone jack hack that sidestepped Apple’s control
00:58:03 – The “140 reasons we might fail” pitch that won over investors
01:06:26 – The taxi ride that convinced Jim he had product-market fit
01:09:28 – Amazon attacks, and why copying doesn’t always work
01:13:18 – The founder’s job after success: choosing hard problems
***
Hey—want to be a guest on HIBT?
If you’re building a business, why not get advice from some of the greatest entrepreneurs on Earth?
Every Thursday on the HIBT Advice Line, a previous HIBT guest helps new entrepreneurs work through the challenges they’re facing right now. Advice that’s smart, actionable, and absolutely free.
Just call 1-800-433-1298, leave a message, and you may soon get guidance from someone who started where you did, and went on to build something massive.
So—give us a call. We can’t wait to hear what you’re working on.
***
This episode was produced by Alex Cheng with music composed by Ramtin Arablouei. It was edited by Neva Grant with research help from Katherine Sypher. Our engineers were Patrick Murray and Robert Rodriguez.
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Today’s callers: Yadi from New York thinks through an expansion strategy for her college campus-based empanada business. Then, Zachary from New York looks for ways to break into big retailers with his fresh-made frozen pies. And Josh from Indiana wonders how to go all-in on his small mouth bass lifestyle brand without overhauling his family’s lifestyle.
Plus, Pete and Rashid reflect on the ‘protein-ification’ of our food, and how a scare last year reaffirmed the importance of doing right by the customer — no matter the cost.
Thank you to the founders of Yadi’s Artisanal Empanadas, Noble Pies, and Achigan for being a part of our show.
If you’d like to be featured on a future Advice Line episode—where Guy and former show guests take questions from early-stage founders—leave us a one-minute message that tells us about your business and a specific question you’d like answered. Send a voice memo to [email protected] or call 1-800-433-1298.
And be sure to listen to Chomps founding story as told by Pete and Rashid on the show in 2023.
This episode was produced by Kerry Thompson with music by Ramtin Arablouei. It was edited by John Isabella. Our audio engineer was Jimmy Keeley.
You can follow HIBT on X & Instagram and sign up for Guy's free newsletter at guyraz.com and on Substack.
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Before Spinbrush became the top selling toothbrush in the U.S—and before Procter & Gamble paid $475M for it—John Osher was a teenager selling earrings for $4.99.
In this episode, John walks through the strange, scrappy, but disciplined path that led to one of the fastest consumer-product breakouts ever: from a six-year stint in a commune (where he learned plumbing and carpentry), to selling baby products and battery-powered spinning lollipops. Finally, the big bet: a $5 electric toothbrush that was cheap enough to compete with manual brushes, and good enough to become a best-seller.
You’ll hear the make-or-break moment that many founders can’t survive: the decision to scrap 400,000 defective brushes before they hit the shelves. And then, the stealth move that turned a “licensing pitch” into a buyout —with one perfectly timed bluff.
What you’ll learn:
Why pricing is about what the market will pay, not what your product costs
The hidden power of packaging (How “Try Me” changed everything)
How to recover from “entrepreneurial terror”
Why scrapping inventory can be the most important decision you’ll ever make
The acquisition formula: you get a lot more money when they want to buy… than when you want to sell

Timestamps:
07:01 - A pricing lesson that John used forever: The 19-cent earrings that sold for $4.99.
12:04 - Six years in a commune and the unexpected skill stack: plumbing and construction.
22:09 - “Entrepreneurial terror” and a lifeline from Toys R Us
29:11 - Spinning lollipops lead to a $166 million Hasbro exit.
35:54 - What’s the real competition: $80 electric toothbrushes, or cheap manual ones?
38:42 - The design breakthrough: fixed + oscillating bristles.
55:43 - P&G admits: “We’ve bought three companies like yours… and ruined them all.”
58:07 - The earnout problem: What happens when Spinbrush performs much better than expected?

Hey—want to be a guest on HIBT?
If you’re building a business, why not get advice from some of the greatest entrepreneurs on Earth?
Every Thursday on the HIBT Advice Line, a previous HIBT guest helps new entrepreneurs work through the challenges they’re facing right now. Advice that’s smart, actionable, and absolutely free.
Just call 1-800-433-1298, leave a message, and you may soon get guidance from someone who started where you did, and went on to build something massive.
So—give us a call. We can’t wait to hear what you’re working on.

This episode was produced by Katherine Sypher, with music composed by Ramtin Arablouei.
It was edited by Neva Grant, with research by Rommel Wood.
Our engineers were Patrick Murray and Kwesi Lee.
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Today’s callers: Mia from Germany wants to know how to balance her pottery business between an online shop and a YouTube channel. Then, Jen from Connecticut is looking for ways to reach more families with her print magazine for tweens and teens. And Anagha from California wonders how to convince people to embrace the time required for her globally-inspired baking kits.

Plus, Julia reflects on Eventbrite’s recent acquisition announcement, and how in-person events can help brands and creators build community in today’s digital world.

Thank you to the founders of Pottery to the People, Anyway Magazine, and Aunty Misri for being a part of our show.

If you’d like to be featured on a future Advice Line episode—where Guy and former show guests take questions from early-stage founders—leave us a one-minute message that tells us about your business and a specific question you’d like answered. Send a voice memo to [email protected] or call 1-800-433-1298.

And be sure to listen to Eventbrite’s founding story as told by Julia on the show in 2020.

This episode was produced by Chris Maccini with music by Ramtin Arablouei. It was edited by John Isabella. Our audio engineer was Cena Loffredo.

You can follow HIBT on X & Instagram and sign up for Guy's free newsletter at guyraz.com and on Substack.
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.