Help Wanted (Money News Network)

Episode: The One Predictable Thing In Business

Release Date: November 13, 2025
Hosts: Jason Feifer & Nicole Lapin

Episode Overview

In this episode of Help Wanted, Jason Feifer dives deep into a powerful and recurring pattern in business, culture, and life: the continuous cycle of bundling, unbundling, and rebundling. Drawing on insights from entrepreneurs, media experts, and his own experience, Jason reveals how understanding this pattern can help you anticipate change, spot opportunities, and take charge of your career or company. The episode offers concrete examples from tech, media, the creator economy, and even personal identity and relationships.

Key Discussion Points & Insights

1. The Bundling/Unbundling/Rebundling Pattern

[04:28 - 06:30]

• Jason introduces the episode’s main theme:

  "Everything bundles, unbundles, and rebundles. Today I'll show you how it works, why it matters, and how to use it to your advantage."

• He attributes the insight partly to a conversation with Ivan Zhao, CEO of Notion. Zhao references the novel Romance of the Three Kingdoms:

  "The empire long divided must unite. Long united must divide. Thus it has ever been."

• This cyclical pattern repeats across industries and eras.

2. Tech Example: Productivity Tools

[06:30 - 08:15]

• Ivan Zhao (Notion) observes:
  • 1990s: Microsoft Office is a "bundle" (Word, Excel, etc.).
  • Cloud era: “Unbundling” as users adopt specialized apps (Trello, Google Docs).
  • Now: Overwhelmed by specialization, people seek simplicity—a “rebundle” (Notion combines everything again).
• Insight: Spotting when people desire more integration or specialization signals opportunity.

3. Media Example: Newspapers & NYT

[08:15 - 10:30]

• Cites Ezra Klein’s observation (“Search Engine” podcast):
  • Newspapers were bundles—news, sports, recipes, etc.
  • The internet unbundled those.
  • "And that left newspapers to primarily sell the news, which is expensive to produce, hard to sell ads against, and not what most of its prior readers wanted anyway." (Jason, 08:55)
  • NYT succeeds by "rebundling"—offering games, cooking, sports, podcasts, and events.
• Memorable image:

  “In 2020, games were just a small part; by 2023, people spent more time on games than news—'literally dwarfing the news'."

4. The Creator Economy: The Next Media Bundle

[10:30 - 12:15]

• Traditional media brands (Inc., Fortune, Forbes) lose audience to individual creators.
• The emerging cycle:
  • Bundle: Media brands aggregate voices.
  • Unbundle: Creators cultivate their own audiences.
  • Rebundle: Creators become mini-media companies, launch their own brand umbrellas (e.g., Steven Bartlett’s company launching podcasts under his brand).
• Steven Bartlett acknowledges Jason’s insight on LinkedIn with a "heart and fist bump emoji."

5. Why The Cycle Never Stops

[12:15 - 13:45]

• Netscape co-founder Jim Barksdale famously said:

  "Gentlemen, there are only two ways I know to make money: bundling and unbundling." (Jason recounting, 12:30)

• Bundles offer convenience but force unwanted extras.
• Unbundling gives choice but can lead to overwhelm (“decision fatigue”).
• Social and personal applications:
  • We bundle/unbundle friends, careers, even aspects of our identity.
  • “No direction is set forever. No path is straight and linear. New things are just new versions of old things.”

6. Actionable Takeaways & Broader Life Applications

[13:45 - 14:30]

• Once you recognize the pattern, you'll see change as part of a natural cycle.
• "If you want to make a change—go for it. Feeling left behind by a change? Watch closely, because opportunity will loop back around."
• Personal and professional growth revolves around continuously creating new bundles.

Notable Quotes & Memorable Moments

• Ivan Zhao, via Jason:

  "Notion is in the bundling business... The empire long divided must unite. Long united must divide. Thus it has ever been." (06:00)

• Ezra Klein (via Jason):

  "Before the Internet, newspapers were bundles... Then the Internet unbundled those topics... The New York Times... rebuilt the bundle with games, food, sports, podcasts, and events." (08:45)

• Jason’s Prediction:

  "The creator economy will literally become the traditional media that it is currently challenging.” (11:40)

• Jim Barksdale’s quote (via Jason):

  "Gentlemen, there are only two ways I know to make money: bundling and unbundling." (12:30)

• Jason’s Closing Guidance:

  "We live in a cycle, and that cycle is ours to shape and ride." (13:57)

Important Timestamps

• 04:28 – Introduction to the episode’s main pattern
• 06:00 – Ivan Zhao/Notion example
• 08:15 - 10:30 – Media industry and NYT case study
• 10:30 - 12:15 – The creator economy’s rebundling phase
• 12:30 – The Jim Barksdale story & why the cycle never ends
• 13:45 – Actionable outlook on change in business and life

Summary: Why This Matters

Understanding the cycle of bundling and unbundling enables you to:

• Predict industry shifts
• Design products or strategies that ride or lead the next wave
• Embrace change in your personal and work life
• See disruption not as chaos but as a signal that opportunity is about to appear—again and again

Jason’s core message:

“New things are just new versions of old things. Are things changing? Go with it... Opportunity will loop back around."

Stay tuned for more practical strategies and career insights from Jason and Nicole on Help Wanted.
For early access to Jason’s weekly newsletter, visit onethingbetter.email.