507: Jim McKelvey—A Square Peg in a Glass Hole
The Way I Heard It with Mike Rowe
Hosted by Mike Rowe
- 1h 11m
- Transcript
Summary
Written by a model from the transcript; not yet reviewed.
This episode features a conversation between the host and entrepreneur Jim McKelvey, recorded live at Brush Creek Lodge in Wyoming. The discussion centers on McKelvey's accidental path to co-founding Square, his background as a professional glass blower, and his theories on innovation as detailed in his book, The Innovation Stack. Throughout the episode, the two explore the parallels between artistic endeavors and building world-changing technology, the challenges of self-promotion, and the looming threat of artificial intelligence replacing genuine human effort.
- When building something truly innovative that has never been done before, traditional business playbooks do not apply and failure is part of the process. 41:50
- Perfectionism can be a convenient excuse that stops entrepreneurs and creators from ever releasing their work into the real world. 40:36
- Mastery in physical crafts like glass blowing depends just as much on precise timing as it does on correct technique. 1:09:18
Chapters
- 0:04Introduction and Square Origin
Mike Rowe introduces Jim McKelvey and explains how the payment device Square was born from a glassblower’s frustration with American Express.
- 1:16The Birth of Square and Market Gap
Jim explains how a $2,000 missed sale led to the idea of a mobile card reader, the founding of Square, and the unmet need in small‑business payments.
- 3:02Personal Story of Glassblowing and Innovation
Jim recounts his background as a glassblower, the challenges he faced, and how those experiences shaped his approach to product development.
- 46:53Authenticity in the Age of AI
Jim and Mike debate authenticity versus artificiality in art, music, and business, highlighting the challenges posed by AI-generated content.
- 50:08Closing Reflections and Takeaways
The episode concludes with final thoughts on innovation, authenticity, and the future of technology, leaving listeners with actionable insights.
- 50:55Media Training and Unplanned Interviews
The conversation opens with a reflection on spontaneous media encounters and the lack of a prepared agenda, setting a tone of candidness.
- 52:29The Power of End-First Thinking
The speakers discuss a design philosophy that starts with the desired outcome and works backward, citing a famed hotelier as an example.
- 53:03Imposter Syndrome in High-Profile Settings
They share feelings of self-doubt when attending elite gatherings, highlighting the tension between expertise and humility.
- 57:04The Innovation Stack and Herb Keller’s Influence
Jim recounts his research on innovation, his meeting with Herb Keller, and how Keller’s insights shaped the narrative of his book.
- 1:00:32From Graphic Novel to Real-World Narrative
Jim explains the evolution of his book’s format, moving from a graphic novel to a grounded story that honors real innovators.
- 1:05:07Luck, Timing, and the Nature of Innovation
The dialogue turns to the role of serendipity in success, with Jim emphasizing that timing and partnership often outweigh skill alone.
- 1:08:01The Lino Glass-Blowing Lesson on Timing
A vivid anecdote illustrates how precise timing, not just technique, is crucial in creative endeavors, drawing parallels to business innovation.
Highlights
- 7:54
The guest explains how the original guru who built Square's data centers was pulled from a top porn site because they already knew how to handle massive web traffic.
- 10:08
Glass Blower to Technologiststory
The guest recounts how quitting a startup run by a crook left him broke, forcing him to rely on his college glass-blowing hobby to make rent.
- 13:29
The Power of Trustinsight
The guest shares an insight from glass blowing about teamwork, explaining how working with a trusted assistant allows him to focus without wasting mental energy.
- 28:08
Building a Personal Paywallstrategy
The guest explains his strategy for fighting AI spam by developing Mail Wall, a personal paywall that charges senders a tiny fee to reach his inbox.
- 42:00
Failing Fast and Iteratinginsight
The guest explains that when operating outside of known human knowledge, your only resource is the ability to fail fast and iterate.
- 57:04
Cold Calling Herb Kelleherstory
The guest describes cold-calling Southwest Airlines founder Herb Kelleher to test his unorthodox theories on innovation against a living legend.
- 1:07:44
The Master Glass Blower's Lessonstory
The guest shares a story about studying with master glass blower Lino Tagliapietra, who taught him that success depends on timing rather than just technique.
Quotes
“Jim McKelvey invented Square, the payment mechanism that basically turns your iPhone into a credit card reader.”
Mike Rowe · 0:34 “I got pissed off, picked up my iPhone and called Jack and I said, "Hey, I want my iPhone to magically turn into a credit card machine."”
Unnamed speaker · 8:51 “The idea's been told, or the story's been told a lot, which is that I was working as a glass blower, selling stuff nobody needs, lost a sale because I couldn't take an Amex card.”
Unnamed speaker · 8:41 “Good is the enemy of great, and I believe that.”
Unnamed speaker · 41:15 “Always began at the end. Always know, you don't need to know how you're gonna start.”
Mike Rowe · 52:29 “The only time he didn't win was in Square's case.”
Unnamed speaker · 57:59 “In glass, timing is really important because if the glass is too hot when you drop it, it'll take the shape and then it'll ooze out.”
Unnamed speaker · 1:09:22 “You don't question Lino. When Lino says something, you don't say, oh, maybe it's, no, you just say, yes, maestro.”
Unnamed speaker · 1:09:44
Sponsored segments
- Chapter 4:02–5:35
- BuildFreedom.us 18:07–19:10
- Pure Talk 32:32–33:46
- NetSuite 47:03–48:13
About this episode
Jim McKelvey https://www.jimmckelvey.com/ is an entrepreneur, innovator, computer engineer, and master glassblower who helped build a billion-dollar company. That's not the usual career path, but then, Jim McKelvey isn't your usual entrepreneur. The co-founder of Square, along with Jack Dorsey, McKelvey turned a frustrating experience in his glass studio into a business that changed the way small businesses get paid. Mike talks with Jim about the art of blowing glass, his involvement with TechShop, and why a guy who helped invent the future of payments is downright terrified of AI. They also discuss The Innovation Stack https://www.amazon.com/Innovation-Stack-Building-Unbeatable-Business/dp/0593086732/ref=sr_1_1?crid=16DJ19211DKIM&dib=eyJ2IjoiMSJ9. LnS_XrhCpOKNgztkKIAoXINJkoGeIohbH6oP-jhDEf3obWMxTv-udMTlFvvns4Zjy3cTg0Wk4pgjFbGM2Ng7UD5B0dpk2036U1SisT2ekxl3mhdfabZU9MCJrPiJvzNn9yEZGUhU4tw1z5lwP1pWs91cp65qZT1ajiaWNFRhB6BwM9b7lN6JK5WsUtFl57FyTPDJkwYLk_FNFSn_DPWfo-Gdiw8LTGd0bbjHNvzEmMY. FC6VzBvANDYinQGRIjVSy31pnnFsn9rb_2Kea_cWLkE&dib_tag=se&keywords=Innovation+stack&qid=1791837266&sprefix=innovation+stack%2Caps%2C182&sr=8-1, McKelvey's book about the unconventional thinking that built Square—and why sometimes the best way to solve a problem is to stop doing what everybody else is doing. BuildFreedom.us https://bit.ly/TWIHIxBuildFreedom—The best place to find a six-figure, AI-proof job. Build your future. Rebuild America. PureTalk.com/ROWE https://bit.ly/PureTalkRowe—Switch your phone service today and get UNLIMITED talk, text, data, and 30G hot spot for just $29.95 a month for LIFE! Not your phone's life—your life! NetSuite.com/Mike https://bit.ly/TWIHIxNetSuite—The #1 Cloud ER. If your revenues are at least in the seven figures, get NetSuite's FREE business guide, Aligning for the Agentic Era: How AI is Changing Everyday Work. Chapter.com/MikeRowe https://bit.ly/TWIHIxChapter—Chapter compares every Medicare plan nationwide to recommend the right coverage for you. Call them at 804-CHAPTER or visit chapter.com/mikerowe https://bit.ly/TWIHIxChapter to get free, unbiased Medicare help. Chapter and its affiliates are not connected with or endorsed by any government entity or the federal Medicare program. Chapter Advisory, LLC represents Medicare Advantage HMO, PPO, and PFFS organizations and standalone prescription drug plans that have a Medicare contract. Enrollment depends on the plan's contract renewal. While we have a database of every Medicare plan nationwide and can help you to search among all plans, we have contracts with many but not all plans. As a result, we do not offer every plan available in your area. Currently we represent 50 organizations which offer 18,160 products nationwide. We search and recommend all plans, even those we don't directly offer. You can contact a licensed Chapter agent to find out the number of products available in your specific area. Please contact Medicare.gov, 1-800-Medicare, or your local State Health Insurance Program (SHIP) to get information on all of your options.
Transcript
12,907 words · 7 speakers
Speaker names marked are inferred from speaking time and the show’s known hosts — they are not voice-verified.
Topics
- Square
- Tech Shop
- Innovation Stack
- Mail Wall
- Block
- Jerry
- Southwest Airlines
- Dallas
- Safr Credit.com
Page updated · transcript and summary are machine-generated