In today's episode, I’m sharing a conversation with content strategist Jana Osofsky all about how to simplify your content marketing strategy while increasing conversions. Jana explains her “capsule blog library” approach — a system built around creating a small collection of intentional, evergreen content that helps your audience feel ready to buy. We discuss why repetition matters more than constantly creating new content, how to repurpose long-form content effectively, and why blogging can still be one of the most powerful low-lift marketing tools for digital entrepreneurs.

Listen to the full episode to hear:

• Why creating 12–20 intentional blog posts can outperform constantly publishing new content
• How to repurpose long-form content into emails, social posts, collaborations, and sales assets
• The biggest mistake entrepreneurs make with content marketing — and what to focus on instead
• Why repetition and clear messaging help you become known for your expertise faster
• How creating content helps refine your offers, messaging, and overall business strategy

Want to quit your job in the next 6-12 months with passive income from selling digital products online?
Check out Startup Society:
https://startupsociety.com

Have you already started your business, but it isn’t generating consistent income?
Schedule a free, 30-minute strategy session with our team to get unstuck!
https://gillianperkins.as.me/?appointmentType=57013246

FREE Resources to Grow Your Online Business:

• Grab our free course: Small Business 101: https://gillianperkins.com/free-training-small-business-101
• Learn “The $100K Method” with our free audio course: https://www.gillianperkins.com/100k-method-signup

Work with Gillian Perkins:

• Apply for $100K Mastermind: https://gillianperkins.com/100k-mastermind
• Get your online biz started with Startup Society: https://startupsociety.com
• Learn more about Gillian: https://gillianperkins.com
• Instagram: @GillianZPerkins

Is your online business making as much as you hoped it would?
If not, listen to my free private podcast series:
👉 Stuck at Zero: Why Your Online Business Isn’t Making Any Money (And What to Do About It)
🔗 https://gillianperkins.com/stuck

Want to grow your business without a massive personal brand or a big ad budget? Chandler Bolt did it — to the tune of $75 million — and in this episode, he breaks down exactly how.

Chandler is the founder of Self-Publishing School, which has helped over 7,000 authors publish their books and has done over $75M in gross revenue. His secret? Books and partnerships. In this conversation, he shares the full strategy — including how one book has generated $7 million in the last 12 months alone.

Listen to the full episode to hear:

• Why a book is the new business card — and why giving it away for free actually makes you more money, not less
• The 5 Ps of the 8-Figure Profit Bridge — Chandler's framework for thinking through every stage of business growth (paying customers → product market fit → profit → people → process)
• The $6–8M partnership playbook — how Chandler's team does 40–70 speaking events per year and runs webinars with partners to drive the majority of their revenue
• The 4 Ps of a bestselling book — person, pain, promise, price — and why getting clear on these before you write a single word changes everything
• The 30-day rough draft challenge — write 1 hour a day for 30 days, and you'll have most of your book done
• Book vs. paid program — why writing a book on the same topic as your course won't cannibalize sales (book = strategy; program = tactics)

Work with Gillian Perkins:

• Apply for $100K Mastermind: https://gillianperkins.com/100k-mastermind
• Get your online biz started with Startup Society: https://startupsociety.com
• Learn more about Gillian: https://gillianperkins.com
• Instagram: @GillianZPerkins

Learn “The $100K Method” with our free audio course - https://www.gillianperkins.com/100k-method-signup

Is your online business making as much as you hoped it would?
If not, listen to my free private podcast series:
👉 Stuck at Zero: Why Your Online Business Isn’t Making Any Money (And What to Do About It)
🔗 https://gillianperkins.com/stuck

If you've built any kind of following on Instagram — even a small one — you've probably noticed the same pattern: people like your posts, watch your stories, maybe even comment. But when it comes time to sell? Crickets. In this episode, I explain exactly why that's happening and share the strategy I use to bridge the gap between Instagram engagement and actual revenue.

In This Episode, I Cover:

• The three reasons your Instagram followers aren't buying — low engagement on sales posts, followers who aren't ready to buy yet, and the friction created by the infamous "link in bio"
• Why common fixes don't work — posting more consistently, upgrading your content quality, chasing more followers, and rewriting your sales page all miss the root problem
• The fix that actually works — using Instagram comment automation (via ManyChat) to turn engagement into email subscribers, without a link in bio or a hard sell
• Why I close 90% of my sales via email — and why converting Instagram followers into subscribers is the highest-leverage move you can make on the platform
• Two specific ways I use this strategy — to fill free webinars and workshops, and to grow my email list from every single post

Want to get more out of your Instagram following? Get 30 days of ManyChat free → https://manychat.com/creators?utm_source=influencer&utm_medium=cold&utm_campaign=GillianPerkins&utm_content=YT — use code GILLIANPERKINS at checkout.

Work with Gillian Perkins:

• Apply for $100K Mastermind: https://gillianperkins.com/100k-mastermind
• Get your online biz started with Startup Society: https://startupsociety.com
• Learn more about Gillian: https://gillianperkins.com
• Instagram: @GillianZPerkins

Learn “The $100K Method” with our free audio course - https://www.gillianperkins.com/100k-method-signup

Is your online business making as much as you hoped it would?
If not, listen to my free private podcast series:
👉 Stuck at Zero: Why Your Online Business Isn’t Making Any Money (And What to Do About It)
🔗 https://gillianperkins.com/stuck

In today's episode, I’m breaking down the best free and affordable online course platforms in 2026. Teachable used to be the clear winner for new course creators, but with its free plan gone and prices rising, it’s time to look at better options — especially if you’re trying to launch lean.

Listen to the full episode to hear:

• Why Teachable may no longer be the best starter option for course creators
• How to use tools you already pay for — like Squarespace, Wix, Shopify, WordPress, SamCart, ThriveCart, Kit, or MailerLite — to host your course
• The best truly low-cost options, including YouTube memberships, Patreon, Skool, and Gumroad
• Which dedicated course platforms are still relatively affordable, including Thinkific, Zenler, and Kartra
• How to choose the right platform based on what you already have and what you’re trying to build
• Why building an audience matters more than choosing the perfect course platform

Work with Gillian Perkins:

• Apply for $100K Mastermind: https://gillianperkins.com/100k-mastermind
• Get your online biz started with Startup Society: https://startupsociety.com
• Learn more about Gillian: https://gillianperkins.com
• Instagram: @GillianZPerkins

Learn “The $100K Method” with our free audio course - https://www.gillianperkins.com/100k-method-signup

Is your online business making as much as you hoped it would?
If not, listen to my free private podcast series👉 Stuck at Zero: Why Your Online Business Isn’t Making Any Money (And What to Do About It)
🔗 https://gillianperkins.com/stuck

In today's episode, I’m sharing the one simple thing you should do right now if you dream of starting your own business someday. Even if you’re months or years away from launching, getting your email list set up today can give you a huge advantage and make growing your business so much easier when the time comes.

Listen to the full episode to hear:

• Why having even a tiny email list puts you far ahead of most aspiring entrepreneurs
• How to quickly set up a free email list using Kit (formerly ConvertKit)
  (Get it here: https://gillianperkins.com/kit)
• The difference between a landing page and a form — and which one to use first
• Simple ways to customize your signup page to start attracting subscribers
• How to create a free resource that encourages people to join your email list

Work with Gillian Perkins:

• Apply for $100K Mastermind: https://gillianperkins.com/100k-mastermind
• Get your online biz started with Startup Society: https://startupsociety.com
• Learn more about Gillian: https://gillianperkins.com
• Instagram: @GillianZPerkins

Learn “The $100K Method” with our free audio course - https://www.gillianperkins.com/100k-method-signup

YouTube has changed more in the past year than in any year before it — and it's mostly because of AI. Not just creators using AI to make content, but YouTube itself using AI to power the algorithm. That means a lot of the advice you've been following? It's already outdated.

In this episode, I'm breaking down the 7 biggest shifts happening on YouTube right now and exactly how to adjust your strategy so you can grow your channel — even if you're starting from scratch.

Here's the thing: yes, there are more creators on the platform than ever. But there are also more viewers than ever. And if you know how to work with the new algorithm, this might actually be the best time to grow.

In This Episode, I Cover:

• Why subscribers matter less than ever — and what actually signals to YouTube that your content is worth promoting
• The new algorithm trifecta — click-through rate, retention, AND viewer satisfaction (this third piece is changing everything)
• Why specificity is winning — how to stop chasing broad appeal and start creating content that speaks directly to one person
• The smart way to use Shorts — why going all-in on Shorts is a mistake, and how to use them strategically to grow your long-form channel
• YouTube as TV and podcast — what this shift means for video length, format, and why audio quality is now non-negotiable
• Why AI slop is getting deprioritized — and how to use AI as a tool without losing the authenticity that actually drives views
• Trust as a ranking factor — why your real stories, specific numbers, and honest opinions are more powerful than ever

Supercharge Your YouTube Strategy:
Watch my free one-hour masterclass on how the YouTube algorithm works and how to build a channel strategy that gets results: https://creatorfasttrack.com/workshop-registration

Connect with Gillian:

• 🌐 Website: gillianperkins.com
• 📸 Instagram: @gillianzperkins
• 📺 YouTube: Gillian Perkins

Enjoying the show? Screenshot this episode, share it to your Instagram Stories, and tag @gillianzperkins — it helps more entrepreneurs find the podcast. And if you love Work Less, Earn More, leave a review on Apple Podcasts to help even more people discover it.

Until next week — stay focused and take action.

In this episode, Gillian Perkins breaks down her real-world experience trying over a dozen different online business models—sharing what worked, what didn’t, and which ones are actually worth your time today.

From affiliate marketing and dropshipping to courses, memberships, and YouTube, she walks through the pros, cons, and earning potential of each model based on years of hands-on experience—including multiple seven-figure successes and a few costly failures.

As you listen, you’ll gain clarity on which business models are best for beginners, which ones scale, and how to choose the right path based on your strengths, goals, and personality.

Ready to finally turn your business idea into real sales? Our 8-week accelerator program Validate helps students launch and earn their first revenue, and we're gearing up to run it again this spring! Put your name on the waitlist to be the first to know when enrollment opens: https://gillianperkins.com/validate

FREE Resources to Grow Your Online Business:

• The $100K Method Podcast Series: https://www.gillianperkins.com/the-100k-method
• Grab our free course, Small Business 101: https://www.gillianperkins.com/101
• Write a Profit Plan for Your Business : http://gillianperkins.com/free-profit-plan

Want to quit your job in the next 6-18 months with passive income from selling digital products online? Check out Startup Society.

Have you already started your business, but it isn’t generating consistent income? Schedule a free, 30-minute strategy session with our team to get unstuck!

Work with Gillian Perkins:

• Apply for $100K Mastermind: https://gillianperkins.com/100k-mastermind
• Get your online biz started with Startup Society: https://startupsociety.com
• Learn more about Gillian: https://gillianperkins.com
• Instagram: @GillianZPerkins

Timestamps:
00:00 Introduction: Businesses I’ve Tried (Wins & Failures)
01:27 Affiliate Marketing (Pros, Cons, Earnings)
04:01 Coaching (High Income, Low Scalability)
06:40 Etsy (Creative but Competitive)
07:56 Dropshipping (Time-Intensive & Risky)
09:02 Courses (Scalable & Highly Profitable)
10:50 Memberships (Recurring Revenue Model)
13:17 Validate Program Mention
16:02 Print on Demand (Flexible but Quality Matters)
18:19 Freelancing (Hard to Differentiate)
20:02 Agencies (Scalable but Not for Everyone)
21:37 Shopify Stores (Powerful but Requires Marketing)
23:31 Blogging (SEO-Driven & Competitive)
26:02 YouTube (Best Growth & Revenue Driver)
27:53 Podcasting (Indirect Monetization)
29:18 Which Online Business Should You Start?

An audience is the #1 thing that will make or break your business's success... but do you have one? If not, check out this early release video (not yet available on YouTube) about the biggest reasons your audience might NOT be growing: https://gillianperkins.com/early-access/

In today's episode, I’m sharing an *interesting* conversation with entrepreneur and coach Moe Choice about rebuilding after setbacks, redefining success, and creating a business that supports the life you actually want to live. Moe opens up about his journey through multiple businesses, personal reinventions, and why he ultimately chose a simpler, freedom-focused approach to entrepreneurship over traditional hustle culture and constant scaling.

Listen to the full episode to hear:

• How Moe rebuilt his life and business after major personal and financial setbacks
• Why solopreneurship and high-ticket consulting became more appealing than traditional business growth
• The mindset shifts that helped Moe redefine success around freedom and fulfillment
• Practical strategies for using LinkedIn outreach to land consulting and coaching clients
• Why simplifying your business can lead to more meaningful and sustainable success

FREE Resources to Grow Your Online Business:

• Get early access to my latest YouTube video (free!): https://gillianperkins.com/early-access
• Grab our free course: Small Business 101 - https://gillianperkins.com/free-training-small-business-101
• Learn “The $100K Method” with our free audio course - https://www.gillianperkins.com/100k-method-signup

Work with Gillian Perkins:

• Apply for $100K Mastermind: https://gillianperkins.com/100k-mastermind
• Get your online biz started with Startup Society: https://startupsociety.com
• Learn more about Gillian: https://gillianperkins.com
• Instagram: @GillianZPerkins