Podcast Summary: Coffee With Cole – "12 Lessons Learned Generating $20M+ Selling Writing Courses Online"

Podcast: Coffee With Cole: The Digital Writing Podcast
Host: Nicolas Cole (with Dickie Bush)
Episode: 12 Lessons Learned Generating $20M+ Selling Writing Courses Online
Date: January 21, 2026

Episode Overview

In this episode, Cole Schafer (with contributions from Dickie Bush) breaks down the twelve most significant lessons learned from building a portfolio of online writing businesses that have generated over $20M in lifetime revenue. From their early days with Ship 30 for 30, through the expansion into Write with AI and the Premium Ghostwriting Academy, Cole shares tactical advice, mindset shifts, and hard-won truths about scaling digital writing products, running large teams, and staying competitive in an ever-evolving landscape.

The tone is candid, insightful, and packed with "learn it the hard way" advice—ideal for digital writers, course creators, and entrepreneurially-minded creatives.

Key Lessons & Insights

1. Operational Complexity Is the Moat

Timestamp: 01:18

• As businesses grow, operational complexity becomes a powerful competitive moat.
• Early on, Ship 30 was simple: blast out emails, fill a cohort.
• Now, running things like webinars requires complex tracking, CRM cross-referencing, and orchestrating multi-layered promotions.
• Quote:
  • "The larger a business grows, the more the operational complexity ... is the moat." – Dickie Bush (01:40)
• Most competitors drop off because they won’t endure that complexity.

2. Subjectivity Doesn’t Scale

Timestamp: 03:52

• Early reliance on talented individuals making subjective calls works... until it breaks at scale.
• For example: Success coaches responding to course participants in various ways—text, audio, video—created inconsistent experiences.
• The game at scale is about removing subjectivity; systematize everything so actions are clear, repeatable, and measurable.
• Quote:
  • "Subjectivity doesn't scale... the game is actually all about removing subjectivity and making every single action in the business as objective as possible." – Dickie Bush (04:52)

3. Customers Want Outcomes Faster, Not More Features

Timestamp: 06:35

• People don’t want more modules—they want their goal, easier and faster.
• Over-complicating courses makes customers question the direction.
• Ruthlessly cut what’s “interesting” but not essential.
• Quote:
  • "The game of building successful education programs is about removing... Let's get to the heart of what you actually care about, and let's remove every single tangential step." – Dickie Bush (07:35)

4. Desire to Start Something New = Uncertainty About Improving What Exists

Timestamp: 08:58

• Starting something new often signals you’re unsure how to improve your current offer.
• Don’t abandon the winner prematurely; focus breeds breakthrough.
• Once you finally learn how to 10x your old thing, you’re often too split across shiny new projects to capitalize.
• Quote:
  • "Whenever you don't know how to improve something, your impulse is to start or find something new and different." – Dickie Bush (09:30)

5. Entrepreneurs Live in Max Risk; Minimize Personal Risk

Timestamp: 11:26

• Don’t double-down on speculation with your personal cash if your business is already risky.
• Advice from a billionaire VC: Play it safe outside the business.
• As the business and personal obligations grow, prioritize de-risking home life.
• Quote:
  • "If you're an entrepreneur... you live in a constant state of max risk. So the best thing you can do with your personal money is take minimal risk." – Dickie Bush (11:35)

6. Only Pay Commissions to Active Salespeople

Timestamp: 13:06

• Tactical: Do not pay out sales commissions in perpetuity if salespeople leave.
• Keeps contracts clean and incentivizes retention.

7. Expect to “Burn” $1M When Learning Paid Ads

Timestamp: 13:58

• Shifting from organic marketing to paid ads is expensive and a totally different skill.
• Cole estimates they spent $1M “paying down ignorance debt” before seeing meaningful returns.
• Paid ads feel riskier and less predictable, especially up front.
• Quote:
  • "We lit on fire a million dollars learning how to run paid ads." – Dickie Bush (14:22)
• Don’t expect to turn on ads and profit instantly; there’s a long, costly learning curve.

8. What Gets Measured Grows; What Gets Ignored Dies

Timestamp: 16:37

• You can’t set-and-forget in business; neglect leads to decline, not plateau.
• Set up dashboards and “dopamine channels” (real-time notifications when sales occur) for constant feedback and motivation.
• Quote:
  • "Unless you are actively growing something, it doesn't plateau and then just maintain. It dies." – Dickie Bush (17:01)

9. New Marketing Channels Require a Year of Iteration

Timestamp: 17:38

• New initiatives (webinars, low-ticket offers, etc.) don’t work out-of-the-box.
• For each channel, expect to iterate for months.
• Only persistence and repeated testing build the moat here.

10. “Fast and Easy” = Slow, Hard, Expensive

Timestamp: 19:33

• If anyone guarantees a new project will be easy, expect the opposite.
• Cole literally rewires his brain: hears “fast and easy,” translates to “slow, hard, and expensive.”

11. Elevate High Performers or Give Them Entrepreneurial Roles

Timestamp: 20:57

• High-potential team members need fresh challenges and vertical mobility.
• Create new roles or evolve them into “intrapreneurs” leading their own business verticals.
• Keeps top talent engaged and growing within your company’s vision.
• Quote:
  • "Everyone has their own hopes, dreams, ambitions, goals. You have to find a way to make sure that each individual's goals sit inside your broader vision." – Dickie Bush (21:45)

12. Video Content Is a Force Multiplier After $3M/year

Timestamp: 22:47

• At scale, video content offers massive resonance and repurposing potential—should’ve invested earlier.
• Great for leverage, serving as pillar content, and deepening audience connection.
• "If I could go back... once you cross around that $3 million a year mark, I think video is such a high ROI investment." – Dickie Bush (22:51)

Notable Quotes & Memorable Moments

• On Complexity as a moat:
  "There is no competition ... because we've grown through these layers of complexity that are very, very hard for just like a solopreneur ... to rebuild for themselves."
  – Dickie Bush (02:08)

• On scaling advice:
  "The game is it's less, not more."
  – Dickie Bush (06:35)

• On personal finance for entrepreneurs:
  "There is nothing riskier you can do with your money than start and run a business."
  – Dickie Bush (11:45)

• On paid ads learning curve:
  "You should mentally anchor to the fact that you need to light a lot of money on fire before you figure out how to do paid ads well."
  – Dickie Bush (14:50)

• On leadership and vision:
  "You have to find a way to make sure that each individual person's goals sit inside your broader vision for the company."
  – Dickie Bush (21:49)

Timestamps for Key Segments

• 01:18 — Operational Complexity as a Moat
• 03:52 — Subjectivity Doesn't Scale
• 06:35 — Outcomes Over Features
• 08:58 — New Projects Signal Avoidance
• 11:26 — Managing Entrepreneurial Risk
• 13:06 — Commission Policy for Sales
• 13:58 — Paid Ads Ignorance Debt ($1M)
• 16:37 — What Gets Measured, Grows
• 17:38 — Year-Long Learning Curves for Marketing Initiatives
• 19:33 — Fast and Easy? Not So Much
• 20:57 — Elevating and Challenging Team Members
• 22:47 — The ROI of Video Content

Final Thoughts

Cole and Dickie’s reflections offer a rare look behind the curtain at what it truly takes to scale writing-based education businesses beyond seven figures. The episode is a masterclass in both mindset and operations—highlighting the value of complexity, systematization, persistence, and strategic patience, while never sugarcoating the inevitable headaches and hard choices along the way.

Ideal For:
Writers, course creators, solopreneurs, and anyone seeking to build digital education products that scale beyond themselves.