The Side Hustle Show: "The Ladders of Wealth Creation: A Step-by-Step System to Up Your Earning Power" (Greatest Hits)

Podcast Host: Nick Loper
Guest: Nathan Barry, Founder of ConvertKit
Date: November 17, 2025

Episode Overview

This greatest hits episode dives deep into Nathan Barry's "Ladders of Wealth Creation" framework—a step-by-step guide to building wealth by acquiring entrepreneurial skills in the right order. Nick and Nathan discuss how aspiring entrepreneurs can level up their earning potential, why jumping straight to passive income can backfire, and practical strategies for side hustlers at every stage. The conversation is packed with personal anecdotes, actionable advice, and compelling insights on skill-building, business models, and the importance of choosing goals that force personal transformation.

Key Discussion Points & Insights

1. The Origin and Purpose of the "Ladders of Wealth Creation" Framework

• Nathan noticed patterns in why some wealth-building paths are more effective than others and wanted a clear way to explain them.
• The core concept: Making money is a skill, and business is a collection of a thousand skills, much like playing an instrument.
• The framework structures skill accumulation in sequential "ladders," preventing people from skipping hard-to-learn steps.
• Quote [03:50]:
  "The ladder of wealth creation is this idea of making money as a skill. Business is a skill, really the collection of a thousand individual skills... how can we break it down into something where you actually understand here are the skills that I'm trying to learn in sequence?" — Nathan Barry

2. The Four Ladders of Wealth Creation

Ladder 1: Trading Time for Money (Employment)

• Examples: Hourly jobs, salaried positions (Wendy’s, yardwork, professional careers)
• Pros: Stability, foundational skills (accountability, reliability)
• Cons: Capped income, 100% active income
• Quote [06:25]:
  "You can move up that ladder, but you're going to be capped." — Nathan Barry

Ladder 2: Your Own Service-Based Business

• Freelancing, consulting, agency work; more responsibility, higher earning potential
• Key skill: Self-accountability; shift from external to internal motivation
• Path: Hourly billing → project-based work → building teams/agencies
• Quote [09:03]:
  "Now you have to provide that accountability because you are your own boss." — Nathan Barry
• Notable insight: Most Side Hustle Show guests started with services as an approachable gateway.

Ladder 3: Productized Services

• Packaging services as standardized products (e.g., "SEO audit for $1,000")
• Requires skills in copywriting, web design, e-commerce, automation
• Bridge between custom services and pure products; allows learning new skills profitably and scaling beyond 1:1 work
• Quote [18:10]:
  "We're still selling a service, but we're starting to act like it's a product." — Nathan Barry

Ladder 4: Selling Products (Digital & Physical)

• Books, courses, software (SaaS), templates, handcrafted goods

• Leverage: Make once, sell indefinitely; sales without manual fulfillment

• Increased complexity and risk (e.g., SaaS vs. simple ebooks)

• Quote [23:59]:
  "Software definitely does [count], all kinds of things. Even selling on Etsy..." — Nathan Barry

• Path to biggest outcomes: Building marketplaces and social networks (e.g., Uber, Creative Market)—highest earning potential but hardest to pull off

• Quote [26:12]:
  "What I'd look for early on is a simple product to sell and support so you can learn some of these lessons." — Nathan Barry

3. Why Skipping Ladders Rarely Works

• Skipping ahead means trying to learn too many skills at once; much higher risk of failure, frustration, and burnout.
• All skills must eventually be learned—when, not if.
• "You can jump from one ladder to another... but you still got to learn all the lessons." — Nathan Barry [37:29]

4. Audience-building and Monetization

• Building an audience creates "attention" you can channel into products, sponsorships, memberships.
• Best returns come when you direct attention to products you own substantial equity in (ex: Dr. Dre with Beats headphones).
• "Each step is easier with an audience because you have captured this attention. And then you choose what product you want to channel that attention to." — Nathan Barry [29:36]

5. Nathan’s Personal Journey Up the Ladders

• Worked at Wendy’s, moved to salaried design job, freelanced, moved to products (WordPress themes), courses, then SaaS (ConvertKit).
• Initial products failed—he reflects that stopping at productized services longer might have yielded more profitable learning.
• ConvertKit: From $1,500/month to $2.5M/month by doubling down and compounding small wins.
• "Principle number eight in this essay is: It takes longer than you think. But the results can be incredible." — Nathan Barry [31:59]

6. The Power of Patience and Arbitrary Deadlines

• Importance of setting dates for evaluating progress (“arbitrary quit dates”) to prevent daily second-guessing.
• "He called it his arbitrary quit date. I'm not even going to think about quitting or throwing in the towel until that date..." — Nick Loper [32:50]

7. Choosing Transformational Goals

• Select goals that force you to become a new person by learning new skills and enduring new challenges.
• Nathan’s goal: Grow ConvertKit to $100M, knowing it will require transformation and skill expansion.
• "Choose a goal that's hard enough that you have to become a different person to achieve it." — Nathan Barry [42:45]

8. Marketing Levers and Practical Optimization

• Recent big wins for ConvertKit include optimizing plan defaults (monthly to annual), resulting in massive increases in annual subscriptions and lower churn.
• Conversion optimization can yield outsized results—tweaking the funnel is as powerful as acquiring more traffic.
• "Just in small tweaks, we went in the last year from 4%...to now 28% [annual plans]." — Nathan Barry [48:42]
• Memberships: Pushing annual plans reduces churn and increases revenue stability.

9. Notable Quotes & Memorable Moments

• On skill-building:
  "Learn in a profitable way..." — Nathan Barry [23:18]
• On being okay with incremental progress:
  "If you find satisfaction and fulfillment on ladder one or two, hey, keep at it." — Nick Loper [15:40]
• On being embarrassed by your old work:
  "If what you were doing two years ago doesn't make you cringe, then I'd wonder...are you living this out in a way where you're leveling up significantly?" — Nathan Barry [40:07]

10. Side Projects and Stacking Solutions for the Same Audience

• Nathan builds internal tools for ConvertKit based on user/creator needs (ConvertKit Commerce, Sponsor Network).
• Rather than leaping into new markets, solve more of your core audience’s adjacent problems for deeper engagement and growth.
• "If you've already got something going, you don't necessarily have to find something totally out in left field." — Nick Loper [46:49]

Timestamps for Key Segments

• [02:56] – Origins & philosophy behind Ladders of Wealth Creation
• [05:49] – The importance of starting simple and not skipping ahead
• [08:02] – Service-based businesses and the skills learned
• [11:14] – Why most hustlers start with services first
• [18:10] – Productized Services explained
• [21:15] – Transitioning to true product businesses & the skill leap required
• [23:59] – Types of products and building for leverage
• [29:36] – The value of audience-building and directing attention
• [31:29] – Nathan’s leap of faith with ConvertKit and the principle of patience
• [37:29] – The perils of skipping ladders & necessity of learning fundamentals
• [40:07] – The personal growth that comes from ambitious business goals
• [46:49] – Strategies for stacking business offerings for the same customer base
• [48:42] – Practical marketing tweaks that boost business performance

Final Thoughts & Takeaways

• Side hustles and entrepreneurial endeavors are best approached as sequential skill-building journeys, not big leaps.
• Long-term results often require more patience than anticipated, but incremental progress compounds into outsized outcomes.
• Evaluating your progress at planned intervals prevents burnout and doubt; focus on the work, review and adjust at your pre-set dates.
• Choose goals that require real change and growth—they are both the most challenging and the most rewarding.

Resources

• Nathan Barry’s "Ladders of Wealth Creation" blog post - nathanbarry.com/ladders
• "Billion Dollar Creator" essay - nathanbarry.com/billion-dollar-creator
• Nathan Barry: nathanbarry.com
• ConvertKit: convertkit.com
• Art of Newsletters podcast

Host: Nick Loper [@nloper]
Guest: Nathan Barry [@nathanbarry]
Revisit for actionable ideas—”Hustle on!”