642 - How to Fix Brand Messaging That Isn't Converting (Even When the Offer Is Good)

Kimberly Roy knows that getting booked on podcasts isn’t about sending more pitches—it’s about sending the right pitches.In this episode of Crush the Rush, Holly sits down with Kimberly Roy, founder of Pitch with Kim, to break down the strategy behind podcast pitching that actually creates business growth. Kimberly shares her three-part framework of angle, fit, and proof, why she prioritizes quality over quantity, and why entrepreneurs may want to stop chasing the biggest podcasts they can find.Kimberly also explains why a great podcast pitch shouldn’t start with a bio, how personal stories can become a powerful visibility advantage, and why researching the host and audience matters before ever hitting send.The conversation goes beyond simply getting booked. Kimberly shares how entrepreneurs can approach podcast guesting as a relationship-building strategy, follow up without feeling pushy, and use visibility to create aligned opportunities, referrals, leads, partnerships, and clients.00:00:00 — Meet Kimberly Roy and the podcast pitching strategy behind her 30%+ booking rate00:01:30 — Building a life-first business through “time leadership”00:04:45 — How loss, grief, and finding her voice led Kimberly from banking to podcasting00:07:30 — Why sharing your story is one of the most powerful ways to stand out00:10:30 — Moving past vulnerability and getting comfortable with visibility00:11:30 — Why Kimberly doesn’t recommend relying on podcast pitch templates00:12:45 — The three-part podcast pitching framework: angle, fit, and proof00:15:00 — Why audience alignment matters more than podcast size00:17:30 — How to research podcasts before sending a pitch00:21:45 — Podcast research tools, Listen Notes, and using AI strategically00:25:30 — Kimberly’s #1 rule: a podcast pitch isn’t really about the person pitching00:27:00 — Why collaboration and promotion can help a pitch stand out00:28:00 — Quality vs. quantity and the problem with chasing bigger audiences00:30:00 — How many times to follow up after sending a podcast pitch00:33:00 — Using breathwork to manage the vulnerability of putting yourself out there00:34:45 — How to connect with Kimberly and learn more about her visibility auditsConnect with Kimberly:Website:  https://pitchwithkim.com/ Instagram: https://www.instagram.com/pitchwithkim/Visibility Audit - Book your free call here: https://pitchwithkim.myflodesk.com/visibility-auditBook your free call here: https://pitchwithkim.myflodesk.com/visibility-audit🔗 LINKS MENTIONED:🤝 2027 Collective Co-Op - www.hollymariehaynes.com/coop🎯 Access to the Backstage Pass 2027: www.hollymariehaynes.com/backstagepass🌎 Website → hollymariehaynes.com📲 Instagram → @thehollymariehaynes🗨️ Chat with Holly → hollymariehaynes

Planning season is about to start, and everyone is going to sell you a prettier document. In this episode I'm making the case that the December planning day is neither the reason your year works nor the reason it doesn't, walking through the seven numbers we track every week inside The Collective Co-Op (only three of them have a dollar sign), and reading a real member scorecard on air so you can hear what those numbers say when they sit next to each other. The January 2027 waitlist is open now at hollymariehaynes.com/coop. 00:00:00 — Why a year-end planning day won’t make the year successful00:01:30 — Holly’s corporate strategy background and the missing piece for entrepreneurs00:03:00 — Why business plans lose to the demands of an ordinary Tuesday00:03:48 — Why Holly recommends 90-day plans instead of 12-month plans00:04:30 — Why revenue is one of the least useful numbers to watch by itself00:05:10 — Leading vs. lagging indicators and what they reveal00:05:35 — New sales committed vs. cash actually received00:06:15 — Why expenses and profit matter more than celebrating revenue00:06:45 — Tracking individual offers to see what is actually selling00:07:20 — The power of five genuine business connections each week00:09:00 — What missed content goals reveal about capacity and planning00:10:00 — Tracking email list growth and open rates00:10:50 — Using a business scorecard to identify gaps and make adjustments00:11:25 — How accountability works inside the Collective Co-Op00:13:30 — The question every entrepreneur should answer before closing their annual plan🔗 LINKS MENTIONED:🤝 2027 Collective Co-Op - www.hollymariehaynes.com/coop🎯 Access to the Backstage Pass 2027: www.hollymariehaynes.com/backstagepass🌎 Website → hollymariehaynes.com📲 Instagram → @thehollymariehaynes🗨️ Chat with Holly → hollymariehaynes

If your business feels more complicated than it needs to be, adding another offer probably isn’t the answer.In this episode of Crush the Rush, Holly sits down with her longtime friend Shannon Matson, founder of The Social Bungalow, to talk about what’s actually working in the online business space as they head toward 2027.Shannon knows this conversation firsthand. After building six different courses over the years, she made the decision to retire them and center her business around one signature offer. The result? A simpler business, clearer marketing, and the ability to exceed the revenue she had previously generated across multiple offers.They are breaking down why being known for one core transformation can make your marketing and sales easier, how to create a lower-ticket offer that builds an audience of buyers, and why simplifying your front-end offers doesn’t mean limiting your revenue potential.Shannon also walks us through her approach to VIP tiers, continuation offers, backend memberships, and her alpha-beta-scaled model for launching a signature offer without feeling like you need everything figured out before you sell.00:00:00 — Why simplifying your business model matters heading into 2027 00:01:30 — Shannon’s definition of building a life-first business 00:03:00 — How Shannon built three very different businesses 00:06:00 — Going from corporate marketing to entrepreneurship 00:09:00 — Why Shannon retired six courses and built one signature offer 00:12:00 — Why one clear offer can speed up the path from follower to buyer 00:13:30 — The low-ticket “step zero” strategy for Q4 00:16:30 — How VIP tiers increase revenue without adding another core offer 00:18:00 — The missing continuation offer in many customer journeys 00:21:00 — Shannon’s alpha → beta → scaled signature offer model 00:24:00 — Why one front-facing offer makes annual planning simpler 00:27:00 — How to identify the right audience and topic for your signature offer 00:30:00 — What’s changing with webinars, masterclasses, and launch events 00:31:30 — The “espresso shot” strategy for getting more from your webinar replay 00:33:00 — Shannon’s favorite productivity tool + where to connect with her CONNECT WITH SHANNON:Instagram:  @thesocialbungalowWebsite: thesocialbungalow.comWTF is Happening in the Online Space Podcast:  An unfiltered breakdown of the 2026 attention economy - what’s changing, what’s working now, and an insider look at how 6- and 7-figure businesses are keeping demand high. 🔗 LINKS MENTIONED:🎯 Access to the Backstage Pass 2027: www.hollymariehaynes.com/backstagepass🌎 Website → hollymariehaynes.com📲 Instagram → @thehollymariehaynes🗨️ Chat with Holly → hollymariehaynes

What if the reason your messaging isn’t landing has nothing to do with your content strategy and everything to do with whether your brand actually reflects who you are?In this episode of Crush the Rush, Holly is joined by  Luna Battalia, founder of Caru Creative and creator of Animist Branding, to talk about a completely different way of approaching personal branding, messaging, and marketing.Instead of constantly trying to reach, convince, and sell to your ideal clients, what if you created a brand world they naturally wanted to step into?They dive into the psychology behind how people experience your brand, why traditional marketing strategies can start to feel disconnected, and the four areas Luna recommends auditing when your messaging isn’t attracting the right people.They also get into one of the biggest conversations happening in business right now: AI and authenticity. Luna shares how she uses AI as an organizational and creative support tool without allowing it to replace the human voice, perspective, and originality that make a personal brand powerful.Plus, they talk about nervous system capacity, why constantly switching strategies may be holding you back, and how to build a business and brand that actually feel sustainable.00:00:00 — Why your messaging might not be the real problem 00:01:30 — Building a life-first business with more space and creativity 00:04:30 — How psychology changed Luna’s approach to branding 00:06:00 — Why buyer behavior and marketing have changed 00:07:30 — Creating a brand world instead of chasing customers 00:10:30 — Brand archetypes and separating yourself from your brand 00:12:00 — Why messaging should come before visual design 00:13:30 — The four-part framework for auditing your brand messaging 00:16:30 — Storytelling and the relationship between your brand and audience 00:18:00 — What to do when you're saying the “right” things but attracting the wrong people 00:19:30 — A simple way to get honest feedback on your personal brand 00:21:00 — How Luna uses AI without sacrificing originality 00:22:30 — Why AI may make human creativity even more valuable 00:24:00 — Marketing strategy, stress, and nervous system capacity 00:27:00 — Why you shouldn't abandon a strategy too quickly 00:28:30 — The branding rule Luna completely disagrees with 00:30:00 — Taking control of how people experience your personal brand CONNECT WITH LUNA:Website: lunaloveleadership.comInstagram: @lunabattaliaFree 5-part Audio Training (Private Podcast) (open 8/3 onwards) https://www.lunaloveleadership.com/fullsend🔗 LINKS MENTIONED:🎯 Free Quiz: What's Standing Between You and Consistent Business Income? → hollymariehaynes.com/quiz👉 Download the Anti-Social Shift Private Podcast → hollymariehaynes.com/shift💡 Download the SEO / GEO Audit Skill → hollymariehaynes.com/seoaudit🌎 Website → hollymariehaynes.com📲 Instagram → @thehollymariehaynes🗨️ Chat with Holly → hollymariehaynes

Does your marketing ever feel like a constant cycle of creating, posting, and starting all over again?In this episode, Holly is joined by Ashley DiBiase, founder of Dash of Social, to break down her content marketing trifecta and how social media, blogging, and email marketing can work together instead of competing for your time.Ashley shares why she recommends starting with long-form content and repurposing it across your marketing ecosystem, how to turn the questions your clients are already asking into valuable content, and why your best-performing ideas shouldn’t disappear after one post.They also dive into an often-overlooked growth strategy: partnership marketing. Ashley shares practical ways to collaborate with complementary businesses -  from webinars and events to co-created blog content so you can get in front of new, highly relevant audiences without constantly chasing more reach.And if you’ve been hesitant to put yourself at the center of your brand, they talk about why personal branding and thought leadership are becoming even more important in an AI-driven content world.00:00:00 — Why doing more isn’t necessarily the answer to better marketing 00:01:30 — Building a life-first business and batching meetings for more focused work 00:03:00 — How Ashley turned blogging into a career in marketing 00:06:00 — Why relying on social media alone limits your marketing potential 00:07:30 — Blogging, Substack, email marketing, SEO, and GEO opportunities 00:08:15 — The content trifecta: social media + email + blogging 00:09:00 — How your marketing channels can move leads through your funnel 00:10:30 — Why your best content should be repurposed instead of used once 00:12:00 — Using Descript and Riverside to turn long-form content into short-form clips 00:13:30 — Partnership marketing and reaching new, targeted audiences 00:15:00 — An easy co-created blog strategy using expert contributions 00:16:30 — How to choose the right business partners and collaborations 00:18:00 — Why personal branding matters even more in the age of AI 00:19:30 — Thought leadership content that builds trust and authority 00:21:00 — The marketing task business owners need to stop overcomplicating 00:22:30 — Ashley’s three-hour weekly content batching workflow 00:24:00 — Video marketing, business growth, and learning to trust your gut Connect with Ashley:Instagram:  @dashofsocial Website: www.dashofsocial.com🔗 LINKS MENTIONED:🎯 Free Quiz: What's Standing Between You and Consistent Business Income? → hollymariehaynes.com/quiz👉 Download the Anti-Social Shift Private Podcast → hollymariehaynes.com/shift💡 Download the SEO / GEO Audit Skill → hollymariehaynes.com/seoaudit🌎 Website → hollymariehaynes.com📲 Instagram → @thehollymariehaynes🗨️ Chat with Holly → hollymariehaynes

What if growing your business didn’t require more content, more platforms, or more hours?In this episode, Holly is welcoming Stephanie Gass back to the podcast to talk about how she’s built a multi-seven-figure business with podcasting at the center—without relying on social media or ads.And now that AI is changing the way people search for and discover content, podcasting may be becoming even MORE powerful.They are digging into how to make your podcast more searchable in the AI era, why clear titles and keywords matter, and how to decide whether repurposing your content is actually worth your time.Stephanie also shares what her life-first business looks like behind the scenes, including how she plans 12 months ahead while working just 15–20 hours a week.One of Holly's favorite parts of this conversation is Stephanie’s reminder that you don’t constantly need to create a new “fire” in your business. Sometimes the smartest strategy is figuring out what’s already working—and pouring fuel on it.00:00:00 — Why podcasting could become even more powerful in the AI era00:01:30 — What a life-first business looks like while working 15–20 hours a week00:03:00 — How Stephanie plans her business 12 months in advance00:04:30 — Why “rinse, repeat, and optimize” beats constantly starting something new00:06:00 — Why AI search validated Stephanie’s long-term podcast strategy00:07:30 — Podcast SEO: searchable titles, keywords, and descriptions00:09:00 — How established podcasts can improve searchability without rebranding00:10:30 — Should you use AI to repurpose your podcast everywhere?00:12:00 — Why your capacity and data should determine your content strategy00:13:30 — How Stephanie turns one specific podcast listener into a qualified lead00:15:00 — Simplifying your lead-generation funnel and using podcast PR strategically00:16:30 — The “one apple, a thousand ways to cut it” content strategy00:18:00 — Why staying focused on your core calling makes saying no easier00:19:30 — The podcast analytics that matter beyond downloads00:21:00 — Why Stephanie doesn’t recommend podcasting breaks—and why authenticity wins00:22:30 — The tool Stephanie uses to manage her podcast workflow and business00:24:00 — The Profitable Podcast Bootcamp + free VIP access with code HOLLYWant the written playbook on getting found by AI? Read GEO for coaches: how to show up in AI search.CONNECT WITH STEFANIE:Website: stefaniegass.comInstagram: @stefaniegassPodcast: GOD-LED BUSINESSProfitable Podcast Bootcamp VIP checkout link - ThrivecartProfitable Podcast Bootcamp - use code HOLLY Listen to Stephanie's previous podcast: 586 - Building Consistent Income Without the Scroll: Stefanie Gass’s No-Social Podcast Strategy with Stefani Gass🔗 LINKS MENTIONED:🎯 Free Quiz: What's Standing Between You and Consistent Business Income? → hollymariehaynes.com/quiz👉 Download the Anti-Social Shift Private Podcast → hollymariehaynes.com/shift💡 Download the SEO / GEO Audit Skill → hollymariehaynes.com/seoaudit🌎 Website → hollymariehaynes.com📲 Instagram → @thehollymariehaynes🗨️ Chat with Holly → hollymariehaynes

What happens when your business looks successful on paper—but behind the scenes, something feels completely off?In this episode, Holly sits down with Laura Schoenfeld to talk about what happens when the business you’ve built no longer fits the person—or life—you have today.Laura knows this firsthand. She was bringing in close to half a million dollars a year, yet she wasn’t keeping enough of that revenue to make the business feel worth it. Eventually, she made a decision most entrepreneurs would be terrified to make: she shut down her multi-six-figure program and rebuilt her business.Today, Laura has intentionally designed her business around her strengths, her season of life, and the work that actually energizes her—all while raising two young daughters and working under 25 hours a week.She talks about why there is no one-size-fits-all business model, how to recognize when you’re following a strategy that was designed for someone else, and how to diagnose the real structural issues in your business instead of continually trying to fix the symptoms.Laura also shares a simple 30-minute exercise you can do this week to uncover what’s working, what’s draining you, and where your business may be asking for a change.00:00:00 — Laura Schoenfeld’s journey from a multi-six-figure program to rebuilding her business around her life00:01:30 — What building a life-first business means while raising two young children00:04:30 — Why an evergreen business model looked perfect on paper but ultimately didn’t fit Laura00:07:30 — The danger of copying someone else’s successful business model00:09:00 — Creating a personal decision-making framework instead of blindly following business trends00:12:00 — Using personality assessments, Human Design, birth charts, and AI to understand how you work best00:15:00 — Why there’s no one-size-fits-all business model00:16:30 — The inside-out framework Laura uses to diagnose what’s actually broken in a business00:19:30 — Why your natural communication style should influence your content strategy00:22:30 — Is your strategy really not working—or are you expecting results too quickly?00:25:30 — What happens when your expertise evolves but your audience doesn’t00:28:30 — Laura’s 30-minute exercise for identifying business misalignment00:31:30 — The business rule Laura has completely unlearned00:33:00 — Why social media engagement is no longer a metric Laura focuses on00:34:30 — Laura’s advice to her younger self: be careful who you allow to influence youCONNECT WITH LAURA:Website: lauraschoenfeldrd.comInstagram: @laura.schoenfeldPodcast: The Nourished CEOThe CEO Type Quiz — lauraschoenfeld.com/quiz🔗 LINKS MENTIONED:🎯 Free Quiz: What's Standing Between You and Consistent Business Income? → hollymariehaynes.com/quiz👉 Download the Anti-Social Shift Private Podcast → hollymariehaynes.com/shift💡 Download the SEO / GEO Audit Skill → hollymariehaynes.com/seoaudit🌎 Website → hollymariehaynes.com📲 Instagram → @thehollymariehaynes🗨️ Chat with Holly → hollymariehaynes

Email marketing shouldn’t feel like another box you have to check every week.If you’re constantly asking yourself, “What am I supposed to email my list about?” there’s a better way.In this episode, Holly sits down with email strategist and automation expert Cheryl Rerick to talk about how to stop treating email like a broadcast channel and start building an intentional customer journey that works in the background of your business.They dig into how to reverse-engineer your emails from the sale, why your welcome sequence is one of the best places to start with automation, and how segmentation and personalization can make your emails feel like they were written specifically for the person reading them. Cheryl also shares what’s changing with AI—from AI-generated inbox summaries to increasingly sophisticated spam filters—and why sounding more human may be one of your biggest advantages right now.  If you want email to feel less like constant content creation and more like a strategic system that nurtures your audience and drives sales, this conversation is packed with practical ideas you can start implementing now.00:00:00 — Why email shouldn’t be treated like a broadcast channel 00:01:30 — Building a life-first business through automation and leverage 00:04:30 — Turning email into a customer journey that creates sales 00:06:00 — Using voice-of-customer research to plan better emails 00:07:30 — Reverse-engineering your email strategy from the sale 00:09:00 — Planning ahead vs. batch writing your emails 00:10:30 — Three ways AI is changing email marketing 00:12:00 — How AI summaries are changing the way subscribers consume email 00:15:00 — AI, spam filters, and what impacts email deliverability 00:16:30 — Using AI as a thought partner instead of your email writer 00:19:30 — The easiest way to make AI-assisted emails sound human 00:21:00 — Email platforms, automation tools, and personalization 00:22:30 — Using tags and dynamic content to personalize emails 00:25:30 — Email trends: segmentation, clicks, replies, and gamification 00:27:00 — How to use segmentation data to create more sales 00:28:30 — The surprising quick win: clean your email list 00:31:30 — Overwhelmed by automation? Start with your welcome sequenceCONNECT WITH CHERYL:Website: cherylrerick.comInstagram: @cherylrerickmarketing Free Resource: AI Inboxes - How Google, Apple, & AI are judging (and summarizing) your emails - https://cherylrerick.com/ai-inboxes/🔗 LINKS MENTIONED:🎯 Free Quiz: What's Standing Between You and Consistent Business Income? → hollymariehaynes.com/quiz👉 Download the Anti-Social Shift Private Podcast → hollymariehaynes.com/shift💡 Download the SEO / GEO Audit Skill → www.hollymariehaynes.com/seoaudit🌎 Website → www.hollymariehaynes.com📲 Instagram → @thehollymariehaynes🗨️ Chat with Holly → HollymariehaynesContact

If you’ve ever felt like you’re doing all the things for your health—eating well, exercising, trying to manage stress—and somehow still feel exhausted, overwhelmed, or like you’re constantly starting over, this conversation is for you.In this episode, Holly is joined by Courtney Townley, a health and self-leadership expert with more than three decades of experience in the wellness industry. Courtney is challenging the traditional wellness playbook and sharing why lasting health isn’t about more willpower, stricter routines, or another protocol.It’s about learning how to lead yourself.They talk about the hidden stressors that impact your health, why midlife requires a different approach to wellness, and how to stop treating every detour like a complete failure. Courtney also breaks down the four practices behind her Consistency Code framework and shares simple ways to make decisions that move you toward the life and health you actually want.00:00:00 — Why your health struggles may have nothing to do with willpower 00:01:30 — Courtney Townley on creating a life-first business 00:03:00 — Using a “priority filter” to decide what deserves your yes 00:04:30 — The problem with information overload and “info obesity” 00:06:00 — Why stress management is a major part of health 00:07:30 — Unnecessary stress vs. on-purpose stress 00:09:00 — Courtney’s “stress bucket” and the dimensions of health 00:10:30 — How midlife hormonal changes can affect stress resilience 00:12:00 — What self-leadership means and why wellness programs often fall short 00:13:30 — Why transformations don’t last without changing your self-image 00:15:00 — The importance of balancing intense effort with rest and recovery 00:16:30 — Ask yourself: What does health mean in this season of my life? 00:18:00 — How one small decision can move you back toward better health 00:21:00 — How to realign quickly when life derails your plans 00:24:00 — Sleep, wellness trends, and Courtney’s daily self-check-in 00:27:00 — The four practices inside The Consistency Code 00:28:30 — Where to connect with Courtney Townley and find her book CONNECT WITH COURTNEY:Website: graceandgrit.comInstagram: @gracegritPodcast: Grace & GritBook: The Consistency Code🔗 LINKS MENTIONED:🎯 Free Quiz: What's Standing Between You and Consistent Business Income? → hollymariehaynes.com/quiz👉 Download the Anti-Social Shift Private Podcast → hollymariehaynes.com/shift💡 Download the SEO / GEO Audit Skill → www.hollymariehaynes.com/seoaudit🌎 Website → www.hollymariehaynes.com📲 Instagram → @thehollymariehaynes🗨️ Chat with Holly → HollymariehaynesContact

What would change in your business if social media became optional—not essential?In this special crossover episode, Holly sits down with Sophia Parra to explore how entrepreneurs can grow, nurture their audiences, and make sales without relying on constant social media content.After becoming a mom, Sophia reduced her workweek from 60 hours to just 18. That shift forced her to identify which activities were truly moving the needle—and which ones were simply keeping her busy.She shares how she replaced disconnected marketing tactics with a circular visibility ecosystem built around three essential priorities: growth, nurturing, and sales. You’ll hear how low-lift offers, listening tours, strategic collaborations, and stronger boundaries can help you create more conversations, convert warmer leads, and protect your schedule.This episode is packed with real numbers, practical strategies, and honest insights about what works when you stop trying to be everywhere online.00:00:00 — Two different playbooks for scaling without social media00:01:30 — Creating a life-first business after becoming a mom00:03:00 — Reducing a 60-hour workweek to 18 hours00:04:30 — Why Sophia made social media optional in her business00:06:00 — The three marketing priorities: growth, nurturing, and sales00:07:30 — Auditing the role social media actually plays00:10:30 — Building a circular visibility ecosystem00:12:00 — Why content alone does not create meaningful nurturing00:13:30 — How a low-lift offer creates conversations and clients00:15:00 — Using listening tours to grow an email list and build authority00:18:00 — Replacing sales calls while protecting your schedule00:22:30 — Conversion rates from Sophia’s low-lift offer00:25:30 — How collaborations expanded Sophia’s network and audience00:27:00 — Boundaries and mistakes to avoid with low-lift offers00:30:00 — The key to pitching high-profile collaborators00:33:00 — Monetizing your audience like an influencer00:36:00 — Why you need to stop guesting and start hosting00:37:30 — Resources for building your own visibility ecosystemConnect with Sophia:Website: gotocoach.clubInstagram:  @sophiaparraPodcast: Marketing UnfilteredFree Resource: https://www.gotocoach.club/auditShe's A Big Deal Beta: https://docs.google.com/document/d/1iXW0B1s0PSqxJjDVpr0Z2PDrqfRblGj_dHzDO0FeLNQ/edit?tab=t.0🔗 LINKS MENTIONED:🎯 Free Quiz: What's Standing Between You and Consistent Business Income? → hollymariehaynes.com/quiz👉 Download the Anti-Social Shift Private Podcast → hollymariehaynes.com/shift💡 Download the SEO / GEO Audit Skill → www.hollymariehaynes.com/seoaudit🌎 Website → www.hollymariehaynes.com📲 Instagram → @thehollymariehaynes🗨️ Chat with Holly → HollymariehaynesContact