Unpacked with Casey Armstrong

ShipBob
  • 5.0 (3)
  • Entrepreneurship

Unpacked is where the truth behind starting and growing a brand comes out. Casey Armstrong, Chief Business Officer at ShipBob, sits down with the founders and CEOs who have built the new age of household name brands and asks the questions you wish you could. What broke. What did they get wrong. What would they do differently. And what drives them to do what they do. Every founder and business has a story. Most of them never get told. New episodes drop weekly. Subscribe wherever you listen.

Episodes

  1. 5d ago

    Greg Taylor (Step One) - Starting with $800 and Couch Surfing to 30M Units Sold and IPO

    On this episode, Step One Clothing CEO and Founder Greg Taylor joins us to unpack:  Starting with $800 to his name and living on a friend's couch, and the moment a billionaire's friend told him his underwear idea had a "0.1% chance" of ever making a dollar Why Greg flew to China's Canton Fair with no brand, no samples, and no name, and got laughed out of factory after factory before one agreed to work with him The "cup sizes for men" idea that seemed absurd to manufacturers but became the breakthrough behind Step One's anti-chafe design How Greg ran quality control on shipping containers from Australia during Covid, without ever setting foot in the factory, by weighing boxes over video call Why the "pair for a pair" referral campaign spiraled out of control, with customers destroying their old underwear on camera in increasingly unhinged ways What it actually felt like to ring the bell at the Australian Stock Exchange as the sole shareholder, with no outside funding, no co-founders, and no debt, and why the real moment happened a week earlier Why Greg compares being a public company to everyone being able to see exactly how much money is in your bank account The out-of-the-blue LinkedIn message from John Lewis that turned Step One into a UK retail brand almost overnight Why Greg says the single hire that most changed the business wasn't in marketing or ecommerce, but a chief legal officer How fatherhood forced Greg to put rigid boundaries around his time, and the "be the dumbest person at the table" philosophy behind how he hires Why Greg believes AI is about to drive the biggest shift business has seen in a hundred years New episodes of Unpacked with Casey Armstrong drop weekly. Subscribe wherever you listen to podcasts.

    Greg Taylor (Step One) - Starting with $800 and Couch Surfing to 30M Units Sold and IPO

  2. Aug 26

    Harley Finkelstein (Shopify) - Building a 100-Year Company & the Future of AI Commerce

    On this episode, Shopify President Harley Finkelstein joins us to unpack: Why Harley says entrepreneurship is "the greatest equalizer," and how watching his refugee father and his grandfather's egg stall shaped how he thinks about starting a businessThe research Shopify did into why the average tenure of an S&P 500 company has dropped from 30 years to under 20, and what that taught Harley about building a "100-year company"Why Shopify deliberately ships features before they're fully baked, and which parts of the platform, like checkout and payments, are never allowed to breakWhat happened when Harley typed the same request into ChatGPT and Google looking for a screen-free phone for his daughter, and why one sent him to Best Buy and the other sent him to a small independent brandThe eye-opening stat Harley shared on Shopify's earnings call: over 70% of orders coming from AI agents are for products outside Shopify's top 100 categories, and what that means for small merchants versus big box retailersWhy Harley believes agentic commerce is the first truly "merit based" discovery tool, and what separates lasting celebrity brands like Emma Chamberlain's coffee company from one-hit-wonder influencer launchesThe story behind Fire Belly, the seven-figure tea company Harley started during the pandemic with his best friend, and why running his own Shopify store makes him a better product leaderWhy Harley calls himself and Shopify "spiky, not well-rounded," and how knowing exactly what you're good at shapes how he spends his time as presidentThe "cha-ching" sound that Harley calls the secret handshake of the Shopify merchant community, and the story of hearing it in a random airport

    Harley Finkelstein (Shopify) - Building a 100-Year Company & the Future of AI Commerce

  3. Aug 19

    Ben Diamond (True Classic) - Scaling to $1B, Surviving Tariffs, and the Costco Playbook

    On this episode, True Classic CEO Ben Diamond joins us to unpack: Why landing a plane on Catalina Island can feel like flying off a cliff, thanks to a runway optical illusion most pilots never see comingBen's 3-part hiring filter (wisdom, intelligence, attitude) and the interview questions he uses to find out if someone actually has gritWhy 2025 was the hardest year of Ben's career...and the most rewarding oneWhat a Foreign Trade Zone is and how it nearly fixed True Classic's cash flow problem overnightWhy True Classic built its customer relationship online first, years before it ever touched retail or wholesaleHow Ben splits inventory across the website, Amazon, Costco, and True Classic's own stores without one channel cannibalizing anotherThe customer story Ben tells at every single All Hands, and what a father-son trip to Costco taught him about the limits of digital adsWhy Ben calls "work-life balance" a myth and time-boxes his day instead, from 5am starts to protected hours with his daughtersWhy Ben says AI already makes him a 1,000x CEO, COO, and CMO, and why he thinks even that's underhypedWhy Ben doesn't care about the CEO title, and the Elon Musk comparison behind what he's actually chasing

    Ben Diamond (True Classic) - Scaling to $1B, Surviving Tariffs, and the Costco Playbook

  4. Aug 6

    Welcome to Unpacked with Casey Armstrong

    Every founder and business has a story. Most of them never get told. Unpacked with Casey Armstrong is coming soon. New episodes drop weekly. Subscribe so you don't miss Episode 1.

    Welcome to Unpacked with Casey Armstrong

Trailer

Ratings & Reviews

5
out of 5
3 Ratings

About

Unpacked is where the truth behind starting and growing a brand comes out. Casey Armstrong, Chief Business Officer at ShipBob, sits down with the founders and CEOs who have built the new age of household name brands and asks the questions you wish you could. What broke. What did they get wrong. What would they do differently. And what drives them to do what they do. Every founder and business has a story. Most of them never get told. New episodes drop weekly. Subscribe wherever you listen.

Information

  • Creator
    ShipBob
  • Years Active
    2026
  • Episodes
    4
  • Rating
    Explicit
  • Copyright
    © Copyright 2026 ShipBob, Inc. All Rights