In partnership with

welcome back!

Founder of the Week

The Saturday Solopreneur Newsletter

practical tips, revenue strategies, and freedom-focused entrepreneurship delivered weekly

This is a newsletter for the following: aspiring solopreneurs, one-person business owners, and expertise monetizers seeking location and time independence.

It mixes:

no-fluff actionable strategies from building audience to generating revenue (with the mindset shifts required to escape traditional employment)

proven frameworks for content creation, copywriting, and audience building that solopreneurs use to compete with larger businesses

freedom-first business philosophy and mental model shifts to rethink work-life integration and lifestyle design

step-by-step tactical lessons from real scenarios like launching digital products, growing social media followings, transitioning to full-time entrepreneurship, and scaling one-person operations

immediately implementable systems you can execute in under 4 minutes for business growth and personal liberation

Basically: a weekly tactical briefing for knowledge workers making the leap from first-dollar to full-time solopreneur with straightforward advice, proven strategies, and freedom-focused business building.

The difference

While others give you theory, Justin gives you the exact playbook he used to build a multi-million dollar one-person business - delivered in bite-sized, weekend-friendly doses that busy people actually read and implement.

Create how-to video guides fast and easy with AI

Tired of explaining the same thing over and over again to your colleagues?

It’s time to delegate that work to AI. Guidde is a GPT-powered tool that helps you explain the most complex tasks in seconds with AI-generated documentation.

1️⃣Share or embed your guide anywhere
2️⃣Turn boring documentation into stunning visual guides
3️⃣Save valuable time by creating video documentation 11x faster

Simply click capture on the browser extension and the app will automatically generate step-by-step video guides complete with visuals, voiceover and call to action.

The best part? The extension is 100% free

breakdown

Newsletter of the Week

1. Anti-Hustle Content Philosophy + Authentic Positioning

Justin creates content that directly contradicts typical entrepreneurship advice - "I'm not a productivity machine" and "I want to take naps on Monday" - positioning himself against the hustle culture that burned him out in corporate.

This authentic messaging attracts overworked professionals who are tired of being told to "grind harder" and want a sustainable path to freedom.

How to replicate: Share your contrarian take on industry norms based on your personal experience. If everyone zigs, you zag - but make sure it's genuinely aligned with your story and values.

2. The "Beginner-First" Content Strategy

With 80% of his audience being beginners, Justin creates content focused on "first dollar to full-time solopreneur" rather than advanced scaling tactics, making his newsletter essential for people just starting their journey.

This creates a massive addressable market while positioning him as the go-to guide for entrepreneurship beginners.

How to replicate: Identify where 80% of your audience sits in their journey, then create content specifically for that stage rather than trying to serve everyone at every level.

3. Dual-Platform Discovery Engine

Justin posts 2-3 times daily on both LinkedIn and Twitter (500K+ followers each), using these platforms purely for discovery and audience building, then funneling everyone to his newsletter.

His social content teases valuable insights but the full frameworks and step-by-step processes live exclusively in the newsletter.

How to replicate: Pick 2 platforms where your audience lives, post consistently with value-driven content, but always drive traffic back to your newsletter for the complete insights.

4. Newsletter as Revenue Multiplier Hub

His Saturday Solopreneur newsletter serves as the central conversion engine - every issue ends with "whenever you're ready, here's 4 ways I can help you" leading to his product suite.

Plus, he monetizes the newsletter directly through $3,500 sponsorships (2 per week = $364K annually) with zero sales process.

How to replicate: Use your newsletter as both a nurture sequence and direct monetization vehicle. Create sponsorship opportunities and always include soft CTAs to your products/services.

5. The "Freedom-First" Lifestyle Positioning

Justin doesn't just sell business courses - he sells the lifestyle outcome of location independence, time freedom, and escape from corporate constraints, making his content emotionally compelling.

His messaging focuses on what life looks like AFTER you build the business, not just the business mechanics themselves.

How to replicate: Lead with lifestyle outcomes and emotional benefits, then support with tactical business strategies. People buy the destination, not the journey.

6. Social Proof Automation System

Justin uses tools like testimonials to automatically collect and display customer success stories across all his sales pages, creating massive social proof without manual effort.

This systematic approach to social proof collection turns every satisfied customer into a conversion asset.

How to replicate: Set up automated systems to collect testimonials and success stories, then strategically place them throughout your funnel to build trust and credibility.

The Result: Justin's newsletter becomes the central hub of a $5.1M business ecosystem, converting cold social media traffic into warm newsletter subscribers, then into customers across multiple price points - all while maintaining 92% profit margins through systematic automation.

JUSTIN WELSH NEWSLETTER REVENUE

Justin Welsh makes $5.1M a year from his newsletter.

Here's the breakdown that'll blow your mind:

Look, most people think newsletters are just about getting subscribers.

That's honestly where they mess up.

Justin has 25,000 subscribers making him $5.1M annually. That's $204 per subscriber per year.

The average newsletter makes $2-4 per subscriber.

Justin's making 50x more than everyone else. It's almost like he's playing a completely different game.

Here's how the money actually works:

Newsletter sponsorships: $364K per year

  • $3,500 per spot, 2 spots per week

  • Zero sales process - fully automated

  • 92% profit margin

LinkedIn course: $3M+ total

  • Newsletter drives 70% of conversions

  • 20,000 students paying $150-200 each

Content course: $1.5M+ total

  • Cross-sell to existing customers

  • Newsletter nurtures prospects for months

Here's what most people don't understand:

His 25,000 newsletter opens generate more revenue than 1M+ social media impressions.

Newsletter subscribers buy 25x more than social followers.

One newsletter mention = $7,000 in sponsorship revenue for 4 minutes of work.

The crazy part?

When he launches courses, newsletter subscribers convert at 8-12% versus 1-2% from social media.

It's almost like having a direct line to people's wallets instead of shouting into the void.

His secret isn't the newsletter content.

It's that his newsletter is a $5.1M revenue distribution system disguised as weekly tips.

Stop thinking about newsletters as content.

Start thinking about them as money-making machines.

The content is just the vehicle. The real product is the relationship.

And relationships pay way better than followers ever will.

week highlight

Newsletter Automation of the Week

Newsletter Growth Automation: Comment → Subscriber Machine

Here's how this Instagram automation converts video comments into newsletter subscribers automatically.

This is a comment → qualification → resource → email capture → newsletter funnel built inside ManyChat for Instagram.

It's designed to turn casual video engagement into qualified newsletter subscribers on autopilot.

1. Trigger: Video Comment Detection

What happens:

  • Someone comments on your Instagram video

  • ManyChat instantly detects the comment

  • Automation fires within seconds

What we see in the flow:

  • Instagram comment trigger at the top

  • Immediate activation (no delays)

Real-life impact:

  • Captures attention while they're actively engaged

  • No manual monitoring required

  • Works 24/7 across all your video content

2. First DM: Following Status Check

What we see:

  • "Send Message" block with: "Hey! Are you following us?"

  • Two response buttons: "Yes" and "No"

Why this works:

  • Feels conversational, not robotic

  • Qualifies engagement level

  • Creates a micro-commitment before the ask

Smart psychology:

  • People who say "Yes" are more likely to take the next action

  • Non-followers get routed differently (or exited)

3. Resource Delivery (Value First)

What happens after "Yes":

  • Immediate value delivery

  • Link to landing page with lead magnet

  • Message like: "Awesome! Here's that [resource] I mentioned in the video"

What we see:

  • "Send Message" block with resource link

  • Clear CTA button directing to landing page

  • No pitch - pure value

Why this converts:

  • Delivers on implied promise from video

  • Builds trust before asking for email

  • Landing page optimized for email capture

4. Email Capture Bridge

The landing page does the heavy lifting:

  • Captures email in exchange for resource

  • Tags subscriber source as "Instagram Video"

  • Automatically adds to newsletter list

Back in ManyChat:

  • 30-second delay after sending resource

  • Follow-up message: "Were you able to grab it?"

5. Qualification Question (The Segmentation Key)

What we see:

  • Question block: "What do you do?" or "What's your biggest challenge?"

  • Multiple choice options:

    • "Building a personal brand"

    • "Growing my business"

    • "Just getting started"

    • "Looking for passive income"

Why this matters:

  • Segments subscribers by interest/stage

  • Personalizes follow-up messaging

  • Improves newsletter relevance

6. Newsletter-Specific Routing

Based on their answer, they get:

Path A: "Just getting started"

  • Message: "Perfect! My Saturday Solopreneur newsletter is exactly what you need"

  • Benefit: "Weekly tips to go from first dollar to full-time entrepreneur"

  • CTA: Direct link to newsletter signup

Path B: "Building personal brand"

  • Message: "You'll love my newsletter - I share exactly how I built 500K+ followers"

  • Social proof: "Join 25,000+ solopreneurs getting my weekly insights"

  • CTA: Newsletter signup with brand-building angle

Path C: "Growing my business"

  • Message: "My newsletter covers the exact strategies I use for my $5M+ business"

  • Value prop: "Practical tips you can implement in under 4 minutes"

  • CTA: Newsletter signup with revenue focus

7. Smart Follow-Up Sequence

What we see:

  • 30-minute delay

  • Condition check: "Did they click newsletter link?"

  • Different paths for clickers vs non-clickers

For non-clickers:

  • Gentle nudge: "Quick question - what's holding you back from starting a newsletter?"

  • Social proof: "25,000+ entrepreneurs are already getting these insights weekly"

  • Final CTA with urgency

For clickers:

  • Thank you message

  • Expectation setting: "Watch for Saturday's issue"

  • Soft pitch for main products

8. Conversion Tracking & Tagging

Behind the scenes:

  • Tags applied based on responses

  • Conversion events logged

  • Integration with email platform

  • Source tracking for analytics

Tags might include:

  • "IG-Video-Commenter"

  • "Beginner-Solopreneur"

  • "Newsletter-Subscriber"

  • "High-Intent-Lead"

🎯 Why This Newsletter Automation Crushes It

Conversion Rate: 15-25% (vs 2-3% typical social to email)

The secret sauce:

  • Immediate response (while attention is hot)

  • Value-first approach (resource before ask)

  • Smart segmentation (personalized messaging)

  • Newsletter-specific routing (not generic email capture)

  • Follow-up recovery (catches missed opportunities)

Real Numbers:

  • 100 video comments → 20 newsletter subscribers

  • Each subscriber worth $204/year (Justin's model)

  • One automation = $4,080 annual value per 100 comments

The Result: Your Instagram videos become a 24/7 newsletter growth machine, converting casual viewers into qualified subscribers who actually want your weekly insights.

It's not just lead generation it's newsletter audience building on autopilot.

end

📧 Ready to Build Your Own Revenue Generating Newsletter?

🎯 No owned audience = you're renting space on someone else's platform Zero recurring revenue = starting from $0 every month

Want Your Newsletter Blueprint?

Pick your $500+ monetization strategy

Set up your first automated revenue stream

Create content that converts browsers to buyers

🔗 Stay Connected:

P.S. Every day you wait is another day your competitors are building their owned audience while you're stuck hoping the algorithm shows your content.

Your newsletter could be earning $500+ by next month.

Catch you later,
Tre

Want to sponsor this and get in front of 500+ people? Get in touch

Was this email forwarded to you? Sign up for free here

Looking for more resources? Listen to my podcast

Want to go deeper? Join my community