Podcast Summary: Travis Makes Money

Episode: "INTERVIEW | Make Money by Removing Friction and Scaling with Empathy"

Guest: Chris Kaufman (Co-founder & Former CCO of StockX, Author of Empathy at Work)
Date: March 6, 2026
Host: Travis Chappell

Episode Overview

This episode features a deep-dive conversation with Chris Kaufman, Detroit-based entrepreneur, creative leader, and co-founder of StockX. Chris recounts his entrepreneurial journey from childhood hustles to founding a multi-billion dollar marketplace and shares insights about making money by removing friction and leading with empathy. The discussion covers lessons from early jobs, the founding and scaling of StockX, the timing of cultural shifts in collectibles, and the vital role of empathy in high-performing teams.

Key Discussion Points & Insights

1. Early Hustles & The Entrepreneurial Itch

(01:06 – 07:08)

• Chris’s First Taste of Earning: At age 10, Chris operated a newspaper route, learning time management, discipline, the difficulty of manual labor, and “how much work goes into making a dollar.”

  “When you’re delivering a newspaper all month … you’re certainly not getting that whole $3. Right. You learn how much labor goes into that.” — Chris Kaufman (02:35)

• Learning to Think About Scalability: Chris identified the limitations of labor-for-money and wondered about easier or more scalable ways to make money—an early entrepreneurial mindset.
• High School Side Hustle: Capitalized on his unique access to digital tools and graphic design skills by making fake IDs for classmates (mid-90s), earning $50 per ID in about 10 minutes—a realization of the potential for higher profit, less effort.

  “There are better ways to make money than delivering papers in sweltering heat or frigid cold.” — Chris Kaufman (07:04)

2. Education and Threading Art Into Business

(07:19 – 12:13) [Main content resumes at 10:34]

• Education: Chris pursued a degree in fine/studio art with a focus in graphic design. He relished the blend of “fine and conceptual art with the rise of computer graphics” in the 90s.

  “I really started thinking about how art, business, and design intersect at a relatively early age.” — Chris Kaufman (11:09)

• Early Business Lens: Even academic projects were approached with a view toward scalability and real-world application.

3. Building Skills & Discovering Product-Market Fit

(12:13 – 19:09)

• Internship at Quicken Loans: Chris started with UX/UI research, but quickly began proactively solving problems by designing better user flows and interfaces.

  “Instead of just… taking notes…I would create a design mockup that solves some of the problems.” — Chris Kaufman (12:48)

• Transition to Product Design: Became Interactive Design Director; environment fostered autonomy and risk-taking.
• First Startups: Launched Quizzle (financial management tool; acquired by Bankrate), then co-founded a future-centric social calendar app (UpTo) that attracted millions but plateaued.
• Pivotal Moment: Facing an acquisition by Yahoo, Chris’s key investor Dan Gilbert convinced the team to stay in Detroit—offering funding on the basis of faith in the team’s abilities, even absent a clear product idea.

  “You build it, I’ll fund it.” — Dan Gilbert, recounted by Chris Kaufman (17:38) “We showed up… and started working on what eventually became StockX.” — Chris Kaufman (18:52)

4. The Birth and Scaling of StockX

(19:09 – 29:41)

• The Core Concept: “What if you applied stock market mechanics to a secondary retail market?” — the principle of transparency, anonymity, and authenticity.
• Category Focus:
  • Initial research suggested 70% of sneakers sold in the secondary market were new-in-box.
  • Chose sneakers first: simplified listings, removed effort for sellers (no photos, no descriptions), allowed one product page per model.

  “They literally just had to come on StockX, create an account, and click a sell button… That was a really powerful part of the platform.” — Chris Kaufman (26:24)

• Lessons in Expansion:
  • Hindsight: would have gone deep (not broad) on sneakers, then added streetwear and collectibles—capitalizing on overlapping audiences for efficiency and stronger community.

  “If we had a do-over… the next vertical, 100% should have been streetwear. Same customer base, tons of overlap.” — Chris Kaufman (27:23)

• Launch Timeline: Started building in early 2015, launched first version in 2016.

5. Cultural Impact and Timing of Collectibles

(28:41 – 33:16)

• Market Shifts: Discussed how the collectibles market is cyclical—huge boom in 1980s, followed by a sharp decline after the rise of the internet revealed overproduction and lack of scarcity.

  “We always assumed there were far fewer of almost everything than there really were.” — Chris Kaufman (30:40)

• The StockX Effect:
  • Provided accuracy, transparency, and democratization to collectors—“expedited” a movement already under way but made it more accessible.
  • Turned scarcity back into a visible (and valuable) commodity, especially for deadstock sneakers.

  “With something like StockX, you’re actually tracking these things. You can see the sales volume, … pretty accurate idea of how many products are actually floating around in the world.” — Chris Kaufman (32:46)

6. Empathy at Work: Leadership and Team Building

(33:16 – 34:44)

• Motivation for the Book: “Empathy at Work” stems from Chris’s MS in Learning & Organizational Change (Northwestern) and career revelations about empathy’s concrete business value.
  • Empathy increases innovation, reduces attrition, and strengthens long-term organizations.
  • The book serves as a “guidebook” for new leaders and team-builders to define their leadership style and team culture.

  “Leading with empathy is a really powerful tool. Not only is it good for morale, but it leads to improved innovation, increased creativity, reduces attrition … it’s good for the long-term sustainability of the business.” — Chris Kaufman (33:40)

Notable Quotes & Memorable Moments

• “When you’re delivering a newspaper all month … you’re certainly not getting that whole $3. Right. You learn how much labor goes into that.” — Chris Kaufman (02:35)
• “There are better ways to make money than delivering papers in sweltering heat or frigid cold.” — Chris Kaufman (07:04)
• “I really started thinking about how art, business, and design intersect at a relatively early age.” — Chris Kaufman (11:09)
• “You build it, I’ll fund it.” — Dan Gilbert, as recounted by Chris Kaufman (17:38)
• “They literally just had to come on StockX, create an account, and click a sell button… That was a really powerful part of the platform.” — Chris Kaufman (26:24)
• “If we had a do-over… the next vertical, 100% should have been streetwear. Same customer base, tons of overlap.” — Chris Kaufman (27:23)
• “We always assumed there were far fewer of almost everything than there really were.” — Chris Kaufman (30:40)
• “With something like StockX, you’re actually tracking these things. ...You can see the sales volume, ... pretty accurate idea of how many products are actually floating around in the world.” — Chris Kaufman (32:46)
• “Leading with empathy is a really powerful tool. Not only is it good for morale, but it leads to improved innovation, increased creativity, reduces attrition … it’s good for the long-term sustainability of the business.” — Chris Kaufman (33:40)

Timestamps for Key Segments

• 01:06 — Chris’s first entrepreneurial experiences and paper route lessons
• 06:27 — High school side gig making fake IDs
• 10:34 — College: Fusing art & design; early thinking about business application
• 12:26 — Quicken Loans internship; transition to product design
• 17:01 — The up-to social calendar startup; near Yahoo acquisition and Dan Gilbert's intervention
• 18:52 — StockX’s inception
• 24:50 — Why sneakers were chosen as the launch category
• 26:50 — “Removal of friction” and platform design philosophy
• 28:41 — Timeline: StockX first launch (2016)
• 29:41 — Collectibles market cycles, the impact of the internet and StockX
• 33:32 — Empathy at Work: book overview and leadership philosophy

Tone & Language

The conversation is candid, practical, and inspiring—reflecting both Travis’s curiosity and Chris’s willingness to share concrete lessons, not just victories but pivots and mistakes. The focus stays on actionable entrepreneurial insights, team-building with empathy, and creating value by reducing friction—for customers and for teams.

Further Resources

• Chris Kaufman’s Book: Empathy at Work — “A companion guide for leaders and teams to foster trust, innovation, and sustainable growth.” (33:32)
• StockX Story: Deep-dive into how transparency, authenticity, and frictionless UX turned a secondary market into a global force.

For anyone interested in unconventional ways to generate wealth, scalable business models, leadership, or the intersection of tech/design and commerce—this is a must-listen episode filled with actionable wisdom.