Podcast Summary: The Foundr Podcast with Nathan Chan

Episode 608: (Solo) Why Short-Term Wins Can Quietly Kill Your Business
Release Date: November 25, 2025
Host: Nathan Chan

Episode Overview

In this solo episode, Nathan Chan explores why an excessive focus on short-term wins can quietly undermine a business’s potential for lasting success. Drawing from over a decade of entrepreneurial experience and interviews with top founders, Nathan articulates the key differences between “winning shallow” with immediate, superficial results and “winning deep” by building foundations for meaningful, long-term growth. He offers hard-earned personal anecdotes, a candid reflection on past mistakes, and actionable guidance for founders eager to escape the “hamster wheel” of constant, reactive activity.

Key Discussion Points & Insights

The Trap of Short-Term Thinking

• Founders’ Mindset Early On
  • When starting out, founders often pursue rapid, tangible wins—sales spikes, marketing hacks, flash promotions.
  • This cycle can become never-ending, with each month’s “big win” immediately replaced by the next short-term push.
  • Nathan’s words:

    “Before you know it, you get caught up in this hamster wheel… and you can be caught up for years in that hamster wheel winning shallow.” [04:10]

• The Problem with Winning Shallow
  • Short-term victories feel good temporarily but don’t create sustainable momentum.
  • Constant “What’s next?” thinking leaves founders exhausted and their teams uncertain.

Learning from Costly Mistakes

• A Painful Example:
  • Nathan recalls a period when their Facebook ads strategy failed, resulting in a loss of nearly half a million dollars in a single month.

    “We lost a lot of money, like very, very quickly… like close to half a million dollars in one month. It was crazy.” [08:05]

  • A knee-jerk reaction followed with serial promotions to “patch the hole”—a classic short-term fix.
• Shift in Perspective:
  • Panic-driven tactics yield fleeting relief but distract from long-term planning.
  • “What I wasn’t doing was, it snapped me out of this long-term thinking.” [09:53]

The Power of Long-Term Strategic Moves

• What Winning Deep Looks Like
  • Assess foundational questions: What should our products look like? Who should we partner with? What strategic moves matter in 6–12 months?
  • Example: Investing significant resources into upgrading Foundr’s course platform and building a subscription model, knowing returns may not materialize for six months or more.

    “We’re upgrading our whole founder course platform… it’s going to take us at least six months of work… but when it launches, it’s going to pay its weight in gold.” [12:02]

• Intentionally Choosing Strategic Bets
  • Not everything can be a deep, long-term play—identify two or three major bets for the next 6–36 months.
  • Quantify expected impact over time, not just immediate boosts.

Personal and Team Development as Deep Wins

• Winning Deep with Team Development
  • Leveling up the team, leadership coaching, and forming a clear vision and shared values.

    “Looking at your team… leveling up your team, looking at coaching, having a clear vision, values, a clear strategic plan, and getting buy-in…” [15:48]

• Podcast Example:
  • Growing the Foundr Podcast itself is a strategic, long-haul commitment that builds trust and connections—no instant ROI.

Getting Closer to the Customer

• Shift from Assumptions to Insights
  • Nathan admits he lost touch with customer needs and relied too much on assumptions.

    “I wasn’t close enough to the customer… only through getting close to the customer and really looking at the intent… that’s when I realized, okay, we need to win deep, not shallow.” [19:27]

  • Speaking directly with customers led to better alignment and focus on long-term value.

Notable Quotes & Memorable Moments

• On the Hamster Wheel of Shallow Wins:

  “You can be caught up for years in that hamster wheel winning shallow. Like, oh, I did this awesome Black Friday launch… but then you realize, okay, what’s happening next month?”
  — Nathan Chan [04:25]

• On Having to Slow Down to Speed Up:

  “As a founder, I know this is a difficult thing to hear, but… sometimes you have to slow down to speed up. You really do.”
  — Nathan Chan [22:13]

• On Strategic Deep Plays:

  “I’m looking to win deep, not shallow. And that is something that Gary, one of my leadership coaches and mentors… taught me. How do you win deep, not shallow?”
  — Nathan Chan [14:36]

• On Clarity and Adaptation:

  “Pausing before you ship a product to really understand what customers are telling you, fixing what’s not working in your backend… Is this still working or is it still aligned? And if it’s not, let it go.”
  — Nathan Chan [23:42]

• Final Takeaway:

  “Constant motion isn’t the same as progress. The founders who win long term are the ones who are willing to pull back, reset and aim with intention.”
  — Nathan Chan [24:11]

Timestamps for Key Segments

• [03:00] – The cycle of short-term wins and why it’s so seductive
• [08:05] – The Facebook ads “disaster” and how it skewed decision making
• [12:02] – Committing to a platform overhaul: an example of a long-term bet
• [15:48] – Developing team, vision, and values as long-haul strategies
• [19:27] – Rediscovering the customer and its strategic impact
• [22:13] – The necessity of slowing down to speed up
• [23:42] – Reflection and aligning action for the long game
• [24:11] – Wrap-up and core message

Key Takeaways

• Short-term “wins” are seductive but keep founders stuck in a reactive loop.
• True, sustainable growth comes from strategic, long-term investments—even when results aren’t immediate.
• Founders should intentionally select a few big “deep” plays rather than trying to win everywhere at once.
• Elevate your team, develop vision and values, and stay close to your customers for clarity.
• Constant activity isn’t progress—periodic reflection and long-range planning are essential.

This episode acts as both a confession and a roadmap, urging founders to pause, zoom out, and commit to building something of lasting value, even if that means embracing patience and uncertainty along the way.