Episode 218: Sell Sooner, Not Sorer: The Entrepreneur’s Guide to a Smart Exit

🎙 Episode 218: Sell Sooner, Not Sorer: The Entrepreneur’s Guide to a Smart Exit Episode Description What’s the best time to sell your business? Hint: It’s not when you’re burned out. In this exclusive segment from Smart Marketer’s Smart Business Exit course, Ezra Firestone is joined by Brad Wayland and Chris Moore of Quiet Light to break down why successful businesses are more attractive to buyers—and how to position yours for maximum value, even if you never plan to sell. “You want to run your business like you're always going to sell it, but you're never going to sell it. You got to love it.” – Chris Moore Whether you’re planning an exit or just want to build a more scalable and sellable company, this is a must-listen episode packed with honest advice and deep experience. ✅ You Will Learn: Why selling out of boredom leads to missed opportunities (and lower multiples) The #1 pitfall that ruins business sales (and how to avoid it) How to build operational systems that make your company transferable When to let go—and how to know if you're truly ready to exit The mindset shift that helps you scale beyond burnout How great businesses become great acquisitions Why the best time to sell is before you feel done 🔗 Links & Resources: Smart Business Exit : Smart Business Exit - Full Course Smart Marketer AI Tools: ai.smartmarketer.com Quiet Light (Buy/Sell Online Businesses): quietlight.com Ezra Firestone – Smart Marketer: smartmarketer.com Brad Wayland – Quiet Light Advisor: quietlight.com/advisors/brad-wayland ⏱ Timestamps (Key Moments Only): 00:01:21 – The #1 Mistake: Trying to Sell Without a Plan 00:02:51 – Shiny Object Syndrome: How Distraction Hurts Valuation 00:04:37 – How to Replace Yourself (and Why It Can Make the Business Grow) 00:07:36 – When Is the Right Time to Sell a Business? 00:10:21 – The “Anvil on the Chest” Test: Are You Still Fired Up or Burning Out? 00:12:38 – “Good Businesses Always Sell”: Why Market Timing Doesn’t Matter 📢 Your Engagement Matters! If you loved this episode, help us grow: ⭐ Leave a 5-star review on Apple Podcasts → Click Here 📲 Share on social media & tag us with #WeOutHere 💬 Send feedback to [email protected] Serve the World Unselfishly and Profit! 🚀

🎙️ Episode 217: John’s DTC Brands to Watch – Whym and the 5-Step Formula for Better Offers Episode Description ✨ “Nobody cleans their room to make it not smell bad. They clean it so they can get that sense of a good smell.” – John Grimshaw This episode is a deep dive into how Whym, a mystery travel company, revitalized an "outdated" industry by wrapping a brilliant offer around a simple service. John Grimshaw unpacks how surprise, novelty, and personalization create viral, high-converting experiences—and he shares his 5-part offer formula that you can use in any business. If you’re tired of bland messaging and weak conversions, this one’s for you. Learn how to build offers that actually move people to buy. 💡 You Will Learn: The 5 elements every great offer needs to connect and convert Why personalization + identity = performance gold in DTC How Whym makes “travel agents” cool again (and highly marketable) Why transformation matters more than features or price How to add surprise & delight to any offer—no matter your niche 🔗 Links & Resources: 🌐 Whym Travel 📈 HYROS Attribution Tool 🎓 Smart Marketer 📲 @smartmarketer on Instagram 🧠 Connect with John Grimshaw ⏱️ Timestamps (Chapters): 00:00 – Welcome & Intro (Anthony + Molly) Anthony tees up the episode and Molly shares a must-have attribution tip for paid ads. 02:13 – John’s Segment: What Makes a Brand Worth Watching Why Whym stood out—and why studying good offers beats copying funnels. 04:28 – What Is an Offer? Why It Matters More Than Creative John defines the concept of an offer and explains why it drives growth more than ads ever could. 06:08 – Step 1: Define the Product or Service Clarify what you're actually selling and why it matters to your customer. 06:55 – Step 2: Create Relevance – The “Why Now?” Make it matter. Relevance helps your audience feel seen and ready to act. 08:22 – Step 3: Identify Your Audience Targeted messaging only works when you know who you're speaking to. 09:45 – Step 4: Give a Reason to Act Now From urgency to incentives, here's how to overcome inertia and spark conversions. 11:57 – Step 5: Sell the Transformation Forget features—focus on how your customer’s life improves after buying. 16:55 – Case Study: Whym’s Irresistible Offer Strategy A breakdown of how Whym made surprise travel feel fun, personal, and Instagram-worthy. 23:36 – Identity, Novelty & Why Whym Nails It How Whym plays into millennial identity and experience collection to win hearts (and wallets). 28:40 – Key Takeaway: Add Novelty to Win in DTC John explains why uniqueness beats polish—and how surprise drives performance. 🙌 Your Engagement Matters! If you enjoyed this episode, here’s how to support the show: 📢 Leave a 5-star review on Apple Podcasts – Click Here 📲 Share this episode, tag @smartmarketer, and use #WeOutHere 💌 Feedback or guest ideas? Email [email protected] Serve the World Unselfishly and Profit 🚀

🎙 Episode 216: Why Now Is the Best Time to Start an Ecom Business Episode Description "This is the best time, I think, better than when I got into the industry over 15 years ago to get started in e-commerce." – Ezra Firestone In this special episode, we’re pulling back the curtain on an exclusive session from the Smart eCommerce course. Ezra Firestone is joined by Laura Paladino and Kurt Elster to talk about the evolution of ecommerce—and why there’s never been a better moment to dive in. From Laura’s journey working four jobs (including Cracker Barrel) to becoming Director of Retention at an 8-figure brand, to Kurt’s eBay hustle during the Furby craze, you’ll walk away inspired—and armed with strategic advice on how to grow in this booming industry. You Will Learn: Why ecommerce has the lowest barrier to entry right now How to avoid overwhelm and choose the right learning path What “Shopify nerds” have known for years (and you should too) Real stories of career transformation through ecommerce Why marketing is all about making the backend prettier for the frontend Where to find trustworthy, high-impact education (and what to avoid) Links & Resources 🎓 Smart eCommerce Course 🧠 Kurt Elster – The Unofficial Shopify Podcast 📈 Hyros – Advanced Attribution Tracking 🌐 Smart Marketer Timestamps 02:17 – Ezra shares why this is the best time to start in ecommerce 02:24 – Meet Laura and Kurt 03:31 – Kurt on getting started with eBay 05:03 – Laura’s journey from Cracker Barrel to Boom 06:17 – What surprised Laura most about marketing 08:41 – Advice for new ecommerce learners: avoid overwhelm 09:27 – Don't be afraid to use Shopify’s powerful documentation  10:21 – Laura’s framework for learning in a noisy space 11:14 – Ezra’s advice: Follow the course and focus Your Engagement Matters! Thanks for tuning in 🙌 If this episode brought you value: 🌟 Leave a 5-star review on Apple Podcasts 📲 Share it on social and tag us — #WeOutHere 💬 Got thoughts? Email [email protected] Serve the World Unselfishly and Profit 🚀

Episode 215 – Smart Marketer Show Winning Ad Creative: What Works Now & How to Measure It Episode Description What makes an ad actually perform in 2025? In this episode, John Grimshaw and Ben Bennett pull back the curtain on the creative process that drives real sales—from emotional resonance to performance metrics. You’ll learn why good creative starts with empathy, how to identify your strongest hooks, and which numbers really matter. Plus, we introduce a brand-new metric (yes, we named it), and show you how AI is changing the creative game—without replacing your team. “If your ad doesn’t have a heart, it will not perform well.” —Ben Bennett You Will Learn The 3 key metrics that reveal if your ad creative is working How to identify and fix poor-performing ads (without guessing) Why emotional hooks beat flashy tactics every time How to use AI image tools like ChatGPT to speed up creative The “thumb stop ratio” metric you should be tracking (and how) A 30-minute Action of the Month to sharpen your creative instantly Links & Resources smartmarketer.com/hyros – Hyros attribution tool Smart Marketer Free Resources – smartmarketer.com/free-resources Smart Marketer Agency – smartmarketer.com/agency Timestamps (Chapters) 02:05 – Meet Ben Bennett: Creative Director at Smart Marketer 03:15 – Top 3 Metrics That Matter for Ad Creative 07:24 – Metric 1: Unique Link Click-Through Rate 11:54 – Metric 2: Conversion Rate & Ad Scent 15:51 – Metric 3: Thumb Stop Ratio 19:00 – How to Set Up and Benchmark Your Thumb Stop Ratio 21:07 – AI for Ad Creatives: How ChatGPT-4 is Changing the Game 26:32 – Action of the Month: Add Heart to Your Hooks 27:27 – The Heart Behind Your Creative 29:30 – If Your Ad Doesn’t Have a Heart, It Won’t Perform 30:33 – The Hook and the Hand: A Smart Marketer Analogy 34:01 – Making Facebook Ads People Don’t Hate 36:24 – Hooks vs. Heart: What's Missing in Most Ads 40:57 – A Simple Exercise 42:56 – The Nine Motivators That Move People 45:12 – Building Visual Hooks Around Real Situations 45:39 – How to Think About Hooks, and How They Fit Into Existing Ads 48:08 – How to Create Really Good Problem Hooks 56:48 – Here's How to Copy This Win Call to Action Enjoyed this episode? Leave us a review, share it with a marketer who needs better ad creative, and don’t forget to subscribe for weekly insights from the Smart Marketer team.

Episode 214: Strategy Meets Soul: What 2024 Taught Us About Marketing, Mindset & Staying Human in 2025 Episode Description 2024 was a year that tested every marketer’s resilience—and in this vulnerable, insight-packed interview, Molly Pittman sits down with Alex Cattoni from the Copy Posse to share what she learned from the trenches. From managing over $600M in ad spend to navigating the emotional highs and lows of leadership, Molly pulls back the curtain on what’s really working in 2025—and how to stay human in the age of AI. You’ll walk away with tactical strategies to boost your ad performance and a renewed sense of purpose and confidence as a marketer, creator, or entrepreneur. "You will always outperform other advertisers—even [those] that are tactically better than you in the platform because you understand the psychology, and you are not just selling a product or service in the news feed." – Molly Pittman You Will Learn Why 2024 was one of the hardest (and most transformational) years in marketing How to use AI without losing your voice, creativity, or soul The 3 biggest ad strategies working right now (based on $600M of data) The #1 mistake most people make when writing ads—and how to fix it How to sell connection, not just conversion Why being “for someone” is the key to standing out in 2025 How to reframe fear and uncertainty into opportunity and clarity Episode Sponsor – Hyros Hyros is the AI-powered ad tracking platform trusted by top marketers and agencies. It shows you exactly which campaigns are driving results—so you can scale without wasting ad spend. If you’re tired of guessing and want brutal, data-driven truth in your marketing, Hyros delivers the clarity to grow. Learn more at smartmarketer.com/hyros Links & Resources Smart Marketer – smartmarketer.com Molly Pittman – mollypittman.com Copy Posse / Alex Cattoni – copyposse.com Launchpad Season 6 – click here to join Smart Marketer Free Resources – smartmarketer.com/free-resources Instagram – Molly Pittman – @mollypittmandigital Instagram – Smart Marketer – @smartmarketer Instagram – Alex Cattoni – @alexcattoni Instagram – Copy Posse – @copyposse Timestamps 00:30 – Intro: What You’ll Learn and Why It Matters 02:27 – Molly's Journey: From Bartender to VP to CEO 12:15 – Why Right Now Is the Best Time to Start 16:40 – AI vs. Copywriters: What’s the Real Impact? 25:15 – What $600M in Ad Spend Says About Winning Ads 36:37 – How to Write Ads That Actually Convert 37:49 – The Biggest Mistake Marketers Make (And How to Fix It) 40:43 – The Mindset That Will Keep You Relevant in 2025 Call to Action If this episode hit home for you, do us a favor: Leave a 5-star review on Apple Podcasts Share it with your community and tag us using #WeOutHere Got thoughts or questions? Email us at [email protected] Serve the world unselfishly and profit!

This week, Molly Pittman and Brett Curry are pulling back the curtain on what’s working right now in digital marketing—and what’s not. From creative hooks and audience targeting to offer structure and AI-powered platform changes, this episode is stacked with real-world strategies to help you stay profitable and ahead of the curve. As marketing shifts and tracking becomes trickier, it’s more important than ever to get your data right. That’s why we’re proud to have Hyros supporting this episode—a platform built to give marketers crystal-clear attribution so you can stop guessing and scale with confidence. If you’re serious about understanding what’s actually driving your sales, Hyros is the tool that gives you the truth you need to win. “If you don’t know what’s working, you can’t scale. The best brands are doubling down on the right hooks and smarter systems.” – Molly Pittman You Will Learn: • How to track your top-performing creative hooks and scale with confidence • The #1 variable that drives success on Meta (after analyzing $1B+ in ad spend) • Why engagement is more powerful than conversion when testing new messages • A practical system for mapping hooks, angles, and campaign goals • How to use your creative to replace targeting as AI takes over • The “system vs. product” strategy that instantly boosts AOV and LTV • Real examples of creative that doubled revenue and unlocked new markets • Why Flewd’s bath brand is one of the smartest DTC models to study right now Episode Sponsor – Hyros Hyros is the AI-powered ad tracking platform trusted by top marketers and agencies. It shows you exactly which campaigns are driving results—so you can scale without wasting ad spend. If you’re tired of guessing and want brutal, data-driven truth in your marketing, Hyros delivers the clarity to grow. 👉 Learn more at Hyros.com Links & Resources: • Smart Marketer – smartmarketer.com • Molly Pittman – mollypittman.com • Follow us on Instagram – @smartmarketer • Smart Marketer Live Tickets – smartmarketerlive.com • Flewd Stress Care – flewdstresscare.com • Recovery Labs – recoverylabs.com • Hyros – hyros.com Timestamps: 00:36 – Pickles & Platforms: The Wild World of DTC 00:02:56 – Codifying Hooks For Scalable Growth 00:06:21 – One Message, Big Risk 00:14:48 – The Power of Engagement Over Attribution 00:31:38 – Don't Sell A Product, Sell A System 00:36:28 – Skittle Nails & The Power of Regrame Your Engagement Matters! Thank you for tuning in! If you got value from this episode, we’d be so grateful if you’d: • ⭐ Leave a 5-star review on Apple Podcasts – Click Here • 📲 Share this episode and tag us @smartmarketer • 💬 Got feedback? Send us a note at [email protected] Serve the World Unselfishly and Profit! 🚀  

In this exclusive live session from Smart Marketer Live, Molly Pittman and John Grimshaw dive into the biggest challenges businesses face in 2025 and, more importantly, the strategies you need to stay ahead. From rising ad costs to shifting consumer behavior and increased competition, this episode is packed with insights on how to adapt and thrive. “We’re in the middle of a major shift. The businesses that succeed in 2025 are the ones that pivot fast, embrace change, and double down on what works.” – Molly Pittman You Will Learn: • Why ad costs are rising (and what you can do about it) • How to adjust your marketing for the new “messy middle” of consumer behavior • The importance of identity-based marketing over interest targeting • How AI is disrupting eCommerce and what that means for your business • Why building a hybrid brand (content + community + commerce) is the key to long-term growth • Actionable steps you can take today to increase engagement, conversions, and brand loyalty Links & Resources:  • Smart Marketer – smartmarketer.com  • Molly Pittman – mollypittman.com  • Follow Us on Instagram – @smartmarketer  • Smart Marketer Live 2025 Super Early Bird Tickets – smartmarketerlive.com     Time Stamps: • 00:00 – Introduction: The 2025 Marketing Shift • 00:00:44 – Why 2024 was a “difficult year” for marketers & entrepreneurs • 00:02:15 – Rising ad costs: The real numbers & why they matter • 00:04:09 – Attention spans are shrinking: How to stand out in a distracted world • 00:06:19 – The messy middle: Why customers now need 15-30 touchpoints before buying • 00:09:16 – Meta’s interest targeting is disappearing. What’s next? • 00:11:00 – The AI disruption: What business owners need to know • 00:15:59 – The Hybrid Brand Model: The key to success in 2025 • 00:21:30 – Building customer loyalty & brand trust in a saturated market • 00:45:57 – Expanding a Brick-and-Mortar Business with Digital Strategies • 00:47:48 – Final Thoughts & Key Takeaways Your Engagement Matters! Thank you for tuning in! Your support keeps this podcast thriving. If you enjoyed this episode, please take a moment to: • 📢 Leave a 5-star review on Apple Podcasts – Click Here • 📲 Share this episode on social media and tag us @smartmarketer • 💌 Have feedback? Email us at [email protected] Serve the World Unselfishly and Profit! 🚀

Are you still tracking Customer Lifetime Value (LTV)? If so, it’s time for an upgrade. In this episode, Molly Pittman and John Grimshaw dive into Customer Value Velocity (CVV)—a smarter, more actionable metric that helps businesses scale faster and make better marketing decisions. Learn how top brands are using CVV to increase revenue, improve monetization, and acquire the right customers. “If you’re only tracking LTV, you’re missing the full picture of how revenue is really flowing in your business.” – John Grimshaw You Will Learn: Why LTV is outdated and what to track instead. How Customer Value Velocity helps you scale revenue smarter. The key difference between acquisition and monetization (and why they must work together). Why tracking speed of revenue matters just as much as total revenue. The most important monetization strategies to increase repeat sales. How top brands like Starbucks optimize customer value for faster ROI. Links & Resources: The Smart Marketer Show – smartmarketer.com/smart-marketer-show Smart Marketer – smartmarketer.com Instagram – @smartmarketer Molly Pittman – mollypittman.com Instagram – @mollypittmandigital John Grimshaw – @grimslaw Timestamps: 00:00:00 – Introduction: Why LTV is Outdated & What to Track Instead 00:00:45 – Meet John Grimshaw: Monetization & Acquisition Expert, CMO of Smart Marketer 00:02:07 – The flaw in traditional LTV tracking 00:03:47 – Numbers Don't Lie 00:24:01 – This Just In 00:30:20 – Action Of The Month 00:49:47 – Copy This Win Your Engagement Matters! Thank you for tuning in! Your support keeps this podcast thriving. If you enjoyed this episode, please follow, review, and share with fellow entrepreneurs and marketers. 📢 Leave a 5-star review on Apple Podcasts: Click Here 📲 Share this episode on social media, tag us, and use #SmartMarketerPodcast 💌 Have feedback? Email us at [email protected] Serve the World Unselfishly and Profit! 🚀

Molly Pittman is back with another DTC Brands to Watch episode, and this time she’s diving into Plufl, the brand that turned a simple concept—dog beds—into a viral human comfort product. Discover how their innovative marketing, branding, and product expansion have made them a leader in the space. “Plufl took a familiar product and reimagined it. This is a case study in creative branding and audience expansion.” – Molly Pittman You Will Learn: • How Plufl transformed a commodity into a viral DTC product. • The power of niche marketing and expanding to multiple customer avatars. • Why their paid ad strategy on Meta & TikTok is so effective. • The genius behind Plufl’s high-converting landing pages. • How they use promotions, upsells, and email marketing to maximize revenue. • The strategy behind their price increase promotion and how you can use it too. LINKS: The Smart Marketer Show - The Smart Marketer Show Smart Marketer – smartmarketer.com Instagram – @smartmarketer Molly Pittman – mollypittman.com Instagram - @mollypittmandigital Fields of Freedom Dog Rescue – fofdogrescue.com Instagram - @fieldsoffreedomrescue Plufl - weareplufl.com Instagram - @weareplufl   TIME STAMPS: 00:00:00 – Introduction: Brands to Watch – Plufl 00:13:29 – Marketing Strategy: From Ads to Checkout 00:15:21 – Product Expansion & The Hug Pillow 00:16:43 – The Power of Landing Pages & Personalization 00:23:07 - Turning Tariffs into Sales: The Power of Price Increase Promotions 00:28:42 – Final Thoughts & Key Takeaways YOUR ENGAGEMENT MATTERS! Thank you for tuning in! Your support keeps this podcast thriving. If you enjoyed this episode, please follow, review, and share with fellow entrepreneurs and marketers. 📢 Leave a 5-star review on Apple Podcasts: Click Here 📲 Share this episode on social media, tag us, and use #WeOutHere 💌 Have feedback? Email us at [email protected] Serve the World Unselfishly and Profit! 🚀

Episode Description In this powerful episode, Molly Pittman shares her inspiring journey of integrating purpose-driven work into her entrepreneurial career. Recorded live at the Four Rooms Mastermind, Molly discusses how her experience building the Fields of Freedom dog rescue has transformed her business, fueled personal growth, and reinforced the importance of structured generosity. She also reveals actionable insights on how entrepreneurs can create lasting impact while scaling their companies. “Your energy source must go beyond just business—it must come from something deeper, something that fuels you for the long game.” – Molly Pittman You Will Learn: Why integrating service-based work into your business can drive long-term success How Molly scaled her nonprofit to save over 7,500 dogs in three years The five steps to building structured, ongoing generosity in your company How generosity strengthens brand loyalty and community engagement Why balancing heart and strategy creates sustainable business models LINKS:  The Smart Marketer Show - The Smart Marketer Show Smart Marketer – smartmarketer.com Instagram – @smartmarketer Molly Pittman – mollypittman.com Instagram - @mollypittmandigital Fields of Freedom Dog Rescue – fofdogrescue.com Instagram - @fieldsoffreedomrescue TIME STAMPS:  00:00:59 – Molly’s Journey: From Digital Marketing to Nonprofit Leadership 00:02:18 – Why Purpose-Driven Work Creates Sustainable Energy in Business 00:05:12 – The Five Steps to Structured Generosity 00:07:31 – How Fields of Freedom Scaled to Save 7,500 Dogs 00:21:15 – Balancing Business, Impact, and Long-Term Vision 00:28:00 – Final Thoughts: How You Can Take Action Today YOUR ENGAGEMENT MATTERS! Thank you for tuning in! Your support keeps this podcast thriving. If you enjoyed this episode, please take a moment to: Leave a 5-star review on Apple Podcasts – Click Here Share this episode on social media, tag us, and use #SmartMarketerPodcast Have feedback? Email us at [email protected] Serve the World Unselfishly and Profit!