Work Less, Earn More

In this episode, I challenge the glamorous myths surrounding the "laptop lifestyle" and reveal a more attainable truth about making money online. I want to reassure you that success doesn't require advanced coding skills or influencer charm but can still be quite lucrative without high barriers to entry. With the increasing demand for online business support today, anyone with basic computer skill...

In this episode, I chat with Sarah Noked, CEO of OBM School, about expanding teams in the digital business realm. Sarah shares her journey from OBM (Online Business Manager) to academy leader, highlighting key moments for hiring support. Key highlights include: When to Hire: Signs that indicate readiness for an OBM or virtual assistant, focusing on achieving consistent revenue around $10,000 a mon...

In this episode, I'm diving deep into an essential question for aspiring entrepreneurs: What should your membership program actually include? Inspired by questions from dedicated listener and Startup Society member Cheryl Kosner, I'm providing valuable insights for those considering launching or enhancing their own membership offerings. I start with my own journey of creating a successful membersh...

In this episode, I talk with Shay Brown, co-founder of Bucket List Bombshells, about building a multi-seven-figure business while embracing a four-day workweek. Shay shares insights on achieving professional success without the hustle and how her business has empowered over 10,000 women globally through efficient business practices. Key highlights include: Four-Day Workweek Benefits: how this shif...

In this episode, I'm joined by success coach Gabe Cox to talk about the upcoming Start-Scale-Succeed virtual conference, scheduled for October 21-23, 2025. Designed for entrepreneurs aiming to break the $100,000 revenue milestone, the conference promises actionable strategies for a sustainable work-life balance. Gabe shares insights into the diverse agenda featuring 18 expert speakers focused on t...

In today's episode, I'm tackling a common challenge for aspiring YouTubers: choosing the right channel type. This decision can often feel overwhelming, but I'm breaking it down into four distinct methods tailored to different personalities and thinking styles, empowering you to begin your channel with confidence. First, we explore the **Intersection Method**, a visual approach using a Venn diagram...

In this episode, I chat with Prerna Malik, co-founder of Content Bistro, about the future of email marketing in 2025. We discuss the challenges of inbox saturation and the importance of authenticity in communication as consumer behavior evolves. Prerna shares key strategies for creating engaging "Nurtured for Sales" newsletters that connect with non-buyers through storytelling, and she explores ne...

In this episode, I'm speaking with Pinterest marketing expert Heather Farris about optimizing Pinterest for your business in 2025. We discuss the impact of AI on the platform and why you need authentic, creator-generated content to stand out from the tidal wave of lazy AI content. Heather shares vital insights on adapting to Pinterest's algorithm changes, the importance of engaging visuals, and pr...

In this episode, I'm sharing my journey of building a successful online business while raising my (now SIX) children! I'm disclosing the effective strategies that have allowed me to thrive as both a mother and an entrepreneur. Let's dive into my business model, struggles, lessons learned, and how I have managed transitions along the way. I'll also tell you the tech and tools that have supported ou...

When you’re just getting started with your business, it can be so tempting to spend time on all the “fun” things like designing the perfect logo, building a fancy website, or posting every day on social media. But here’s the thing: those tasks don’t actually move the needle when it comes to making money. In this episode, I’m sharing the common mistakes I see new entrepreneurs make that end up wast...

If you’re running an online business, you already know how important it is to have systems that actually work—not just ones that look good on paper. But turning audience attention into revenue? That can feel a lot trickier. In this episode, I’m joined by business strategist Jordan Gill , the founder of Systems Saved Me. Jordan and I dig into the most common mistakes entrepreneurs make with sales c...

Choosing the right legal structure for your business can feel… overwhelming. Sole proprietorship, LLC, S corp, C corp… what do all these terms even mean ? And more importantly, how do you know which one is right for YOU? When I was first starting out, I had so many questions about business structures. I didn’t want to mess up something that could affect my taxes, my liability, and my long-term gro...

In this episode, I’m joined by leadership strategist and operations expert Jillian Dolberry to talk about how you can build a reliable system for making smarter decisions in your business. We dive into why reactive management can hold you back, how to make sure your choices align with your core values, and the daily habits that keep operations running smoothly. Jillian also shares practical tips f...

Ever feel like there’s just too much to do and not enough time to do it all? In this episode, I’m sharing the exact weekly planning process I use to keep my business running, homeschool my kids, and still have time to breathe. I’ll walk you through how I prioritize what actually matters, set boundaries that protect my time, and build in flexibility so my week doesn’t feel overwhelming. I’ll also l...

Ready to try Melio for yourself? You can get started with no monthly fees using their Melio Go plan, or upgrade for advanced features like batch payments, approval workflows, and W9/1099 tax tools. https://go.melio.com/gillian2025 In this episode, I’m talking about how AI is reshaping content creation, for better or for worse. While it’s easier than ever to churn out low-quality work, there’s also...

In this episode, I’m joined by Dr. Dave Heath , founder of Human Focus AI, for a conversation about how entrepreneurs can use AI to run their businesses more efficiently. Dr. Heath shares why now is the time to start integrating AI, comparing it to the early days of the internet, and how adopting it early can give you a major advantage. We dive into practical ways to use tools like ChatGPT for con...

In this episode, I’m sharing a challenge that nearly every aspiring entrepreneur faces at some point: how do you choose the right product to create and sell? I’m walking you through the five-step framework I use to help my students make this decision strategically so they can confidently create a product that sells, even if they have a small audience or feel uncertain about their expertise. Whethe...

In this episode, I’m joined by my friend and fellow entrepreneur, Tara Wagner. Tara is an accredited small business consultant who has been through a lot in recent years, navigating chronic health challenges and long COVID while still running a successful business. We had a really honest conversation about what it looks like to build a sustainable, profitable business when life throws you curvebal...

AI has changed the game, making it easier than ever to create more content but also raising the bar for quality. In this episode I talk about what’s working right now, from story-driven videos and long-form interviews to the growing shift toward video and podcasts as preferred content formats. We’ll dive into why building trust and creating personal connections is more important than ever and how...

In this episode, I'm excited to share a conversation I had with Gabe Cox during the Grow Your Business Without Social Media Online Conference. We talked all about how to grow your business with content marketing in a way that’s both strategic and sustainable. I shared why YouTube is my favorite platform for long-form content and how I use it to attract leads and build trust with my audience. We al...

In today's episode, I’m diving into a topic that every entrepreneur needs to understand: how to protect your business legally without spending a fortune. I may not be a lawyer, but after years of building and running multiple businesses, I’ve learned a lot about the legal steps small business owners need to take to stay protected and profitable. I’m sharing what I’ve learned about choosing the rig...

As I get ready for the arrival of baby number six, I’ve been deep in preparation mode, not just at home but inside my business too. In this episode, I’m sharing exactly how I’m setting my business up to run smoothly while I step away for maternity leave. I walk you through the behind-the-scenes projects I’ve been prioritizing, like creating content in advance, planning upcoming launches, and onboa...

See what AI can do for your website with a custom Website Re-Write: https://startupsociety.shop/products/website-rewrite-client-attracting-messaging (Use coupon code WORKLESS when you check out for 40% off.) In this episode, I’m joined by copywriting expert Jason Benfer to talk all about how to write better, more strategic sales copy, especially with the help of AI. We dive into why so many entrep...

You can get started for free with Melio Go, or upgrade to one of their paid plans if you want even more advanced features: https://go.melio.com/gillian2025 If you’re a stay-at-home mom dreaming about starting your own business, I recorded this episode just for you. I’m sharing the story of how I started one of my very first online businesses, a digital product business that gave me the flexibility...

In today's episode, I’m continuing the conversation I started over on the Online Business Podcast with Kwadwo Sampany-Kessie. We’re diving deep into the inner workings of my YouTube-based evergreen sales funnel from how I generate consistent traffic, to the way I’ve optimized conversion rates and structured my email sequences to be both effective and ethical. I’m sharing the behind-the-scenes of h...