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.

Netflix shouldn’t have survived.

In 1997, Blockbuster owned home entertainment—9,000 stores, a business fueled by late fees, and a brand that felt untouchable. Netflix was a scrappy DVD-by-mail experiment that almost sold itself off to stay alive.

So how did Netflix win?

In this conversation, Reed Hastings breaks down the behind-the-scenes decisions that helped the business thrive: the uncomfortable leadership choices, the culture blueprint that surprised corporate America, and a near-catastrophic misstep that could have blown the whole thing up.

Reed also talks about what shaped him long before Netflix: being a late-bloomer, teaching in the Peace Corps, learning humility from a former boss, and the painful management mistakes he made while building his first company.

This is a masterclass in: challenging the status quo, choosing a culture on purpose, and making big bets without pretending you’re always right.

What you’ll learn: 

• Why Netflix’s early “obvious” advantages weren’t enough—and how close it came to dying
• The leadership lesson Reed learned from a CEO who was admirable… but strategically wrong
• Why Reed says the best companies are like championship sports teams: if you can’t perform at peak, leave
• The “keeper test” and how it changed corporate culture
• The Qwikster fiasco: what went wrong, and how Netflix moved to prevent future missteps
• Building a House of Cards: How Netflix made the leap to original content
• Reed on the media landscape: The remote-control moment of truth, rival streamers, and the rise of AI

Timestamps:

• 00:08:06 — “I was a late bloomer.” Reed on why no one saw greatness coming
• 00:09:30 — Peace Corps in Swaziland, and the moment he nearly quit
• 00:11:23 — An unforgettable lesson learned from the CEO who washed Reed’s coffee cups
• 00:14:39 — Building his first company in a cold cabin—no internet, just obsession and proof of concept
• 00:16:48 — Reed’s early struggles as a manager: “Too busy chopping wood to sharpen the axe.”
• 00:24:11 — Blockbuster’s late-fee pain and an early bet on DVDs
• 00:44:47 — The dot-com crash… and the $50M LVMH round that saved Netflix (barely)
• 00:47:12 — A possible Blockbuster buyout: “We probably would’ve taken any offer.”
• 00:56:18 — The Netflix culture deck: “We’re not a family,” and why that shook people up
• 01:05:07 — The Qwikster crisis, and the backlash that humbled Reed
• 01:19:33 — The competition: Netflix is just <10% of TV viewing—and the real threat is YouTube

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 and researched by Sam Paulson with music by Ramtin Arablouei. It was edited by Neva Grant. 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.

Plus, Jon’s take on why now is a good time to start a business — in spite of market uncertainty.   

Today’s callers: Dan from Washington considers new offerings beyond his core loose leaf yerba mate product. Then, Mike from New Hampshire wants to expand his woodworking business beyond his basement, without taking on debt. And Maggie from Georgia wonders how to respond to rising customer acquisition costs for her soccer-themed dog brand.

Thank you to the founders of Heretic Yerba, MTS Woodworking, and Floofball for being a part of our show.

If you’d like to be featured on a future Advice Line episode, 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 Betterment’s founding story as told by Jon on the show in 2018.  

This episode was produced by Noor Gill with music by Ramtin Arablouei. It was edited by John Isabella. Our audio engineer was Kwesi Lee.

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.

In the late 2000s, two French mountain athletes set out to build a running shoe that captured the feeling of flying. 

Jean-Luc Diard and Nicolas “Nico” Mermoud had spent decades inside the innovation engine at Salomon—where product was obsession. In 2007, as Nico recovered from a brutal ultramarathon around Mont Blanc, the founders fixed on a problem that Big Footwear didn’t care about: downhill running was destroying bodies. Their solution: make the shoe bigger, softer, and shaped like a rocker.

At first, their prototypes looked like clown shoes. Runners who preferred minimalist footwear laughed at them. Retailers said no. But the founders kept doing the one thing that they knew could reverse things: they made people try them.

HOKA went from under $3M in sales in 2012 to more than $2B a year—and in this episode, you’ll hear how it happened: the risky design, the early cash crunch, and the strategic partnership that helped them win the U.S. market.

What you’ll learn:

• How to think of a shoe as a machine, not just a piece of apparel
• The go-to-market weapon that worked: relentless demo-ing 
• Why outside money can’t always solve a cash flow bottleneck (and what does)
• How HOKA used performance proof to avoid being dismissed as a gimmick
• Why HOKA partnered with Deckers—and why it wasn’t just about capital
• How to keep a “rebel” mindset as competitors start copying you

Timestamps:

(Timecodes are approximate and may shift depending on platform.)

• [07:12] George Salomon’s leadership lesson: the CEO who sought advice from an intern
• [11:11] Nico’s first day at Salomon: testing ski prototypes on a glacier
• [18:42] The ultramarathon race where Nico’s legs crumbled (and why)
• [21:29] A breakthrough insight: performance changes with surface (leaves, lava, snow)
• [31:25] Designing a sneaker as if it were a car: engine, tires, seat
• [40:00] The “clown shoe” prototype—and the first successful run 
• [47:22] Elite runners kickstart the brand 
• [49:02] The hard part nobody glamorizes: factory minimums, bank demands, anemic cash flow
• [53:31] Deckers enters: the minority investment that unlocks the U.S. (without killing the brand)

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 and researched by Rommel Wood with music composed by Ramtin Arablouei.

It was edited by Neva Grant. 

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. 

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Plus, Mark on his most challenging venture yet: revolutionizing the prescription drug market in America.

First we meet Lucy from Washington DC, considering an opportunity to bring her upside-down peanut butter brand into a big box retailer. Then Macy from Utah, wondering if her youth-safe skincare products are better marketed to kids or their parents. Then Dan from North Carolina, looking to reboot his pre-pandemic business selling hand-crafted wooden razors. And finally Kristen from Michigan, questioning if she should expand her children’s winter wear brand with gear for other seasons.

Thank you to the founders of One Trick Pony, Girlyish Skincare, Imperium Shaving, and Northern Classics for being a part of our show.

If you’d like to be featured on a future Advice Line episode, 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 Mark Cuban’s original episode on the show from back in 2016.

This episode was produced by Casey Herman with music by Ramtin Arablouei. It was edited by John Isabella. Our audio engineers were Robert Rodriguez and Jimmy Keeley.

You can follow HIBT on X & Instagram and sign up for Guy’s free newsletter at guyraz.com or on Substack.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

A bright blue guitar covered in orange koi fish vanished from a museum display … and Swifties immediately knew what it meant.

That distinctive guitar—the one Taylor Swift used to record Speak Now—had been a gift. Hand crafted, by the founders of Taylor Guitars. When she brought it back on stage during her Eras tour, the fans went wild.

In this episode, Bob Taylor and Kurt Listug tell the unlikely story behind one of the world’s most respected acoustic guitar brands—how it grew from a tiny San Diego repair shop doing $30,000/year into a global business with nine-figure revenue. And how it survived every challenge that should’ve ended it: a distributor deal that didn’t add up, a brutal market crash in the disco era, and such slow growth that—five years into the business—the founders could barely pay themselves a salary ($15/week).

It’s a story about serendipity, obsession, and the quiet power of a partnership where each person knows their lane—Bob with relentless craftsmanship, Kurt with the discipline to turn it into a massive business.

Plus: the purple 12-string featured in Prince’s “Raspberry Beret” … the MTV Unplugged boom that boosted the business … and why the founders eventually chose to convert the business to 100% employee ownership.

What you’ll learn:

• The operating principle that changed Taylor’s production: one finished guitar beats 10 half-finished ones
• How to make a slow-growth business survivable (and why Bob saw it as “education”)
• How to recognize a bad distribution deal
• The design innovations that drew musicians to Taylor guitars
• Why Bob got a call from Taylor Swift’s dad when she was 14—and the iconic guitar her fans grew to love
• How the business managed demand shocks during COVID
• Why an ESOP can be a founder’s best “succession plan” decision
• What a great partnership looks like in practice

Timestamps:

(Timecodes are approximate and may shift depending on platform.)

• 00:06:39 – The high school moment: “I didn’t have $175 … so I thought, I’ll just make a guitar.”
• 00:07:14 – The American Dream shop: the hippie setup that became a launchpad
• 00:10:20 – The “baseball bat neck” problem with guitars—and Bob’s happy-accident innovation
• 00:11:59 – Buying the shop for $3,700 … then realizing it didn’t include the name (or phone number)
• 00:22:31 – The sentence that changed everything: “Would you rather have 10 half-done guitars or one done guitar?”
• 00:26:28 – The distributor deal that ended in layoffs: good sell job, bad math, and what they learned
• 00:38:30 – Buying out the third partner: why the business doubled when “the brakes were off”
• 00:59:52 – Before Taylor Swift was Taylor Swift: a phone call from a proud dad, and a promotional concert that almost went unheard
• 01:09:36 – The inflation economics of guitar building

***

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 Rommel Wood. Our engineers were Patrick Murray and Maggie Luthar.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.