Business Lunch Podcast: "Lessons from Failure: A Path to Growth"

Host: Roland Frasier with co-host Ryan Deiss
Date: January 29, 2026

Episode Overview

In this candid and insightful episode, Roland Frasier and Ryan Deiss dive into the invaluable lessons they've learned from failures and setbacks over the previous year. Framed as a "year in review," the conversation is both introspective and actionable, centering on how embracing and analyzing failure has led to substantial business and personal growth. Ryan shares his top five lessons, supported by Roland’s relatable anecdotes and probing questions, offering a practical playbook for entrepreneurs aiming to avoid costly mistakes and accelerate success in the coming year.

Key Discussion Points & In-Depth Insights

The Value of Reflecting on Failure (00:14–00:56)

• Ryan’s “Annual Ritual”: Ryan describes his process of looking back at the year's failures and regrets, extracting lessons, and then mentally “turning the page.”

  • Quote: “For me, it actually is [cathartic]. I don’t enjoy it, but it’s cathartic. And you learn the most from failure.” (00:47 - Ryan)

• Success vs. Failure as Teachers: Both hosts agree that failure is the best teacher, far surpassing success in the depth of its lessons.

Reality vs. Metrics: When a "Good Year" Feels Hard (01:48–02:09)

• Despite growth in revenue and profitability, the year felt difficult due to layoffs, project closures, and uphill battles—a reminder that outward metrics don’t always match the internal journey.

Lesson 1: Distributions Are the Ultimate Sign of a Healthy Business (02:09–09:19)

• Shifting Focus from Growth to Distributions: In facing stalled growth, Ryan reframed meetings with the question: “What needs to be true to just be able to distribute $50K next month?”

  • This radically changed decision-making, emphasizing financial health over vanity metrics (like revenue or NPS).

• Distribution vs. Reinvestment: Roland probes the tension between distributing profit and “leaving money in for growth.” Ryan explains that businesses find ways to spend whatever is left in, often inefficiently. Taking money out forces rigorous capital allocation.

  • Quote: “The optimistic entrepreneur’s ability to spend will always, always, always outpace our ability to earn.” (05:21 - Ryan)
  • Quote: “If you take that money out... you’re going to think a lot harder about it.” (06:37 - Roland)

• Lessons Learned: The failure was tolerating a lack of profit and not adhering strictly to a “profits first” model.

Lesson 2: You (and Your Team) Can Only Do One Thing at a Time (10:15–13:20)

• Ryan recounts overcommitting to 17 initiatives in one quarter for a single company—with only two completed (and those being “stupid little things”).

  • Quote: “So much of this is just breaking our own rules.” (12:30 - Ryan)

• In the most productive quarter, the team chose five initiatives, completing them sequentially or by delegating to distinct teams.

Lesson 3: Show Me Your Calendar and I’ll Show You Your Priorities (13:20–14:46)

• Personal Productivity Audit: Ryan notes periods where his calendar was “wide open” led to unproductive months, as other people’s priorities filled the void.
  • Quote: “If we don’t claim our calendars, they get taken by somebody else.” (14:41 - Ryan)
• Action Point: Block out time intentionally for key initiatives; otherwise, important projects stall.

Lesson 4: Good Content Compounds—But It Takes Time (14:54–16:20)

• Compounding value from producing high-quality content is a long game. Their content strategy, started at the year’s beginning, only produced notable impact by Q4, at which point they could turn off paid traffic without hurting growth.
  • Quote: “The things that are the most valuable take the longest to build. If it happens quickly, it’s probably not going to be as valuable.” (15:46 - Ryan)

Lesson 5: The Excuse is the Reason (16:20–18:30)

• Ryan identifies a recurring pattern: when he rationalized avoiding hard decisions due to “reasonable” excuses, those were, in fact, the very reasons TO take action.
  • Examples: Not firing a “critical” team member, not sunsetting a legacy product.
  • Quote: "If we’ll flip it and make the excuse the reason... it’s much better advice." (17:45 - Ryan)

Memorable Quotes & Moments

• On the Psychology of Distributions:
  Roland: “When you take the money out and it’s your money... all of a sudden, we’re asking a lot more questions than we were when it was just leaving it in there.” (08:09)

• On Overcommitting:
  Ryan: "We kind of started all 17, but got none of them to any point of completion. So many half-built bridges, so much wasted time.” (13:18)

• On Calendar Management:
  Ryan: "If you say you don’t have time for something... is it on your calendar? If it’s not, you have to acknowledge it simply isn’t as important...” (19:16–20:03)

• Summary Laugh:
  Ryan: “At some point, mistakes start being worth millions of dollars.” (21:12)

Timestamps for Key Segments

• 00:14: Ryan describes his annual “failure and regret” review
• 02:09: Shift from growth thinking to focus on distributions
• 04:34: Roland challenges the distribution vs. reinvestment mindset
• 10:15: The consequences of trying to do too many things at once
• 14:46: How priorities are revealed and hijacked through calendar audits
• 15:46: The long, slow payoff of good content
• 16:20: The practice of flipping excuses into reasons for action
• 18:38–20:26: Quick review of all five key lessons

Actionable Summary of the Five Lessons

1. Distributions = Health: Focus on building a business that can generate and distribute real profit, not just grow revenue.
2. Single-tasking Wins: Limit priorities for yourself and your company to maximize impact—do fewer, bigger things sequentially.
3. Calendar = Priorities: Your calendar is a mirror of what truly matters. If it’s not scheduled, it won’t get done.
4. Content Compounds (Slowly): High-value content efforts pay off, but only with patience and consistency.
5. Excuses Reveal the Path: The reason you’re avoiding an action is often the very reason you need to do it. Invert your excuses into action steps.

Final Thoughts

Roland and Ryan’s honest review of failure reframes it as an essential part of achieving lasting business growth. Their five distilled lessons, drawn from real setbacks, serve as a potent checklist for anyone hoping to convert last year’s regrets into next year’s breakthroughs.

Key Takeaway:
"Every million dollars helps." (21:33 – Roland) — Don’t let learned lessons go unheeded; each one has the potential to save or make millions.