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The Thoughtful Entrepreneur

Josh Elledge of UpMyInfluence.com
The Thoughtful Entrepreneur
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  • 2180 - Insights on Modern Advertising Tactics with Unicorn Innovations' Maxwell Finn
    Navigating the Complex Landscape of Modern Advertising: Insights from Maxwell FinnIn this episode of The Thoughtful Entrepreneur, host Josh Elledge sits down with Maxwell Finn, President of Unicorn Innovations. Maxwell shares expert insights into the fast-changing world of digital advertising, the psychological foundations of effective marketing, and how his company partners with brands for long-term, scalable growth. Whether you’re a seasoned business owner or an emerging entrepreneur, this episode is packed with timeless strategies and modern tactics for cutting through the noise in a crowded digital landscape.Rethinking Paid Advertising: Psychology First, Platforms SecondMaxwell’s central message is clear: success in advertising begins with an understanding of human behavior, not flashy trends or platform tricks. He challenges the obsession many marketers have with tools like Facebook Ads or TikTok hacks, emphasizing instead the importance of marketing psychology, behavioral economics, and storytelling.He reflects on historical campaigns such as the “Torches of Freedom” movement—an early example of influencer marketing and narrative-driven advertising created by Edward Bernays. These time-tested strategies continue to influence how successful brands earn trust and drive conversions today.Maxwell encourages business owners to dive into foundational literature from authors like Rory Sutherland (Alchemy), Daniel Kahneman (Thinking, Fast and Slow), and Richard Thaler (Nudge). These books unpack the mental shortcuts and irrational tendencies that influence how customers behave—and ultimately, buy.About Maxwell FinnMaxwell Finn is a growth-focused entrepreneur and the President of Unicorn Innovations. He has over a decade of experience scaling digital advertising campaigns for brands across e-commerce, SaaS, and personal branding. With more than $150 million in trackable ad spend, Maxwell brings unparalleled expertise to his clients through strategic advisory, education, and hands-on ad management.About Unicorn InnovationsUnicorn Innovations is a boutique digital marketing agency that works with high-growth businesses through a unique hybrid model. The agency selectively partners with clients, often taking equity in addition to providing marketing services. Unicorn's specialty lies in high-impact paid ad campaigns combined with strategic oversight to drive long-term value and profitability.Links Mentioned in this EpisodeUnicorn InnovationsMaxwell Finn on LinkedInKey Episode HighlightsWhy psychological triggers and behavioral science should guide your ad strategyThe dangers of chasing ad trends without foundational knowledgeHow Unicorn Innovations partners with brands using equity and advisory modelsWhy creative content and unique “angles” still outperform ad tech aloneThe future of paid advertising and why brand identity is more important than everConclusionThis episode with Maxwell Finn is a masterclass in modern advertising. His deep understanding of marketing psychology, paired with real-world experience scaling ad campaigns, offers entrepreneurs a clear roadmap for building smarter, more resilient strategies. If you’re ready to stop guessing and start building ads that convert, this conversation is a must-listen.Apply to be a Guest on The Thoughtful...
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  • 2179 - What Works in Small Business Marketing with Ninety Five Media's Emma Tessler
    Unlocking the Secrets of Social Media Marketing: Insights from Emma Tessler of Ninety Five MediaIn this episode of The Thoughtful Entrepreneur, host Josh Elledge chats with Emma Tessler, the Founder and CEO of Ninety Five Media. Emma shares her journey from solopreneur to agency leader, offering insight into how small businesses can scale through intentional content marketing. She also discusses the balance between creativity and data, the evolving role of social platforms, and why longer-form video is the future of digital engagement.Finding Balance in a Digital WorldEmma began the conversation by opening up about her personal growth journey—specifically how she’s cultivated balance in a world driven by digital noise. After spending years pouring everything into her business, she realized the importance of unplugging and finding a creative outlet. For Emma, that outlet is needlepoint. It’s a meditative activity that brings joy, social connection, and a refreshing break from screen time.Transitioning into her business, Emma introduced Ninety Five Media, a digital marketing agency that serves small businesses looking to grow their audience and convert followers into paying customers. The agency provides a full suite of services including strategy, content creation, community engagement, and performance tracking—so founders can stay focused on running their business without the overwhelm of managing their online presence.Emma also shared her outlook on social media trends. While many users feel disenchanted by algorithm shifts and platform saturation, she believes there's opportunity for brands that deliver meaningful, educational, and story-driven content. Longer-form video, especially on platforms like TikTok and Instagram, is outperforming short clips by increasing audience retention and deepening brand connection.About Emma TesslerEmma Tessler is the Founder and CEO of Ninety Five Media and host of the podcast Stop Scrolling, Start Scaling. With nearly a decade of experience in the digital marketing space, Emma leads a powerhouse team that helps small businesses create content that drives real growth. Her mission is to empower founders with strategies that convert and build community-driven brands.About Ninety Five MediaNinety Five Media is a full-service digital marketing agency helping entrepreneurs grow through strategic content creation and social media engagement. From content calendars to analytics, the agency specializes in delivering results without locking clients into long-term contracts. Their motto: create content that converts and builds lasting community.Links Mentioned in this EpisodeNinety Five Media WebsiteEmma Tessler on LinkedInStop Scrolling, Start Scaling PodcastKey Episode HighlightsWhy Emma uses needlepoint as a creative and mindful outletHow Ninety Five Media supports small business owners with done-for-you marketingThe importance of video—especially long-form content—for building trust and conversionsWhy data should drive your content strategy, not trendsThe power of community building in growing an online presenceConclusionEmma Tessler reminds us that...
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  • 2178 - Connecting Consumers with Exceptional Service and Discovering Daisy's with Hagan Kappler
    Unlocking the Future of Smart Home Technology: Insights from Hagan Kappler, CEO of DaisyIn this episode of The Thoughtful Entrepreneur, host Josh Elledge welcomes Hagan Kappler, the founder and CEO of Daisy, a company on a mission to redefine smart home and small business technology services. Hagan shares how Daisy is creating a national brand in an otherwise fragmented industry—one that offers not just installation, but also consistent, long-term support.Whether you're a consumer seeking a better smart home experience or an entrepreneur interested in franchise ownership, this conversation uncovers the technology trends, business models, and growth opportunities shaping the future of connected living.Redefining Smart Home Services Through Standardization and SupportAs the smart home market continues to expand—now exceeding $30 billion in the U.S. alone—it still faces serious fragmentation. Many technology contractors are small, local operators with deep product knowledge but limited business infrastructure. Hagan Kappler launched Daisy to solve this problem by offering a platform where talented installers can operate under one cohesive, national brand with the support they need to scale.Daisy provides solutions ranging from home audio and visual systems to smart lighting, security, motorized shades, and fully integrated control panels. But what truly sets Daisy apart is their ongoing commitment to service. Unlike typical one-off installations, Daisy ensures homeowners, builders, and property managers receive continual updates, maintenance, and training—maximizing the longevity and effectiveness of their smart systems.For small business owners, Daisy’s franchise model opens doors. Entrepreneurs can either start a new operation, convert an existing business, or acquire a company, all while receiving centralized support in operations, marketing, customer service, and technology. It’s a win-win: customers enjoy trusted expertise, and franchisees get to grow under a brand backed by national reach.About Hagan KapplerHagan Kappler is the founder and CEO of Daisy, the first national brand in smart space installation and services. Previously, she served as CEO of Threshold Brands, leading nine service businesses across 550+ locations. Hagan has held leadership roles with ServiceMaster Clean, Merry Maids, and Ingersoll Rand/Trane, and began her career at McKinsey & Company and Goldman Sachs. She also helped launch Starbucks Blonde Roast. Hagan holds a bachelor’s in history from Williams College and an MBA from the University of Virginia’s Darden School. She lives in Newport Beach, CA with her four children.About DaisyDaisy is redefining smart home and business technology with a comprehensive, customer-first approach. By combining expert installation with long-term service, Daisy offers audio-visual, lighting, security, and automation solutions tailored to every client. Franchise partners benefit from marketing, HR, customer support, and operational tools that make running a tech business easier and more profitable. Learn more at joindaisy.com.Links Mentioned in this EpisodeVisit Daisy's WebsiteConnect with Hagan Kappler on LinkedInKey Episode HighlightsHow Daisy fills a major gap in the smart home market by providing both installation and ongoing serviceThe opportunity for small business owners to scale through Daisy’s national franchise modelWhy the...
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  • 2177 - Discovering Authentic Learning Experiences from Luma Brighter Learning's Gina Anderson
    Embracing the Power of Learning: Insights from Gina AndersonIn this episode of The Thoughtful Entrepreneur, host Josh Elledge sits down with Gina Anderson, CEO and co-founder of Luma Brighter Learning, to discuss how learning can drive personal transformation, support resilience, and inspire innovation in an AI-powered world. Gina—also an accomplished author and learning scientist—shares her insights on why hard tasks can unlock personal breakthroughs, how to maintain creativity in an automated world, and the future of authentic learning experiences.Why Embracing Discomfort Fuels GrowthGina begins by reflecting on her own relationship with discomfort, particularly through her routine of running—not because she loves it, but because it challenges her. She pairs this tough activity with joyful elements like scavenger hunts for colorful shells, turning a mental hurdle into an opportunity for mindfulness and reward. This playful mindset parallels how we should approach personal development: by pairing tough goals with incentives that make the journey sustainable.This theme connects to her core belief that learning, like running, requires repetition and resilience. Gina underscores that discomfort is not a sign of failure—it's evidence that growth is happening. When learners push past their comfort zones, they open the door to confidence, creativity, and capability. She offers practical tips like breaking big goals into small milestones and celebrating small wins to build momentum.For those struggling with change or burnout, Gina recommends re-evaluating how you engage with challenges. Are you avoiding them—or are you learning from them? Her advice is clear: lean into discomfort, but bring a little joy with you.About Gina AndersonDr. Gina Anderson is the co-founder and CEO of Luma Brighter Learning, a learning design and technology company specializing in training solutions for transportation and logistics companies. She is the author of Thrive: How Learning Can Ignite a New Way Forward and co-author of Perspectives on Invisible Illnesses. A former educator, administrator, and e-learning innovator, Gina is passionate about the intersection of emotional wellness and applied learning science. Her work has helped thousands of learners across industries adopt lasting behavior change through authentic, engaging educational experiences.About Luma Brighter LearningLuma Brighter Learning is a trailblazer in custom learning solutions for frontline industries. With a focus on transportation, logistics, and safety-critical roles, Luma combines the power of learning science, technology, and human connection to deliver behavior-changing educational programs. The company’s 5-Mode Learning approach ensures deeper engagement through learner-to-learner, learner-to-coach, learner-to-self, learner-to-content, and learner-to-technology interactions.Links Mentioned in this EpisodeLuma Brighter LearningLearningWithGina.comEpisode HighlightsWhy pairing hard tasks with fun rewards helps make difficult learning sustainableHow AI should enhance—not replace—human creativity and problem-solvingThe importance of self-reflection and authenticity in learning designWhy real-world context is essential in education that drives behavior changeHow Luma uses its 5-Mode Learning framework to personalize training in frontline...
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  • 2176 - Why Accurate Content Matters in Legal Marketing with Optimize My Firm's Lindsey Busfield
    Mastering SEO for Law Firms: Insights from Lindsey Busfield of Optimize My Firm🎧 Listen to this episodeOn this episode of The Thoughtful Entrepreneur, host Josh Elledge speaks with Lindsey Busfield, Vice President, Chief Operating Officer, and partner at Optimize My Firm, a disruptive leader in legal SEO. Lindsey shares the strategies her team uses to help law firms dominate search engine rankings through human-written content, niche targeting, and a client-first approach that forgoes long-term contracts. Whether you’re a solo attorney or part of a large legal team, this conversation offers powerful SEO insights tailored to the legal profession.The Critical Edge of SEO in Legal MarketingLindsey opens the episode by reminding listeners that when people need legal help, they go straight to Google. If your law firm isn’t showing up on the first page—especially in the coveted Google local 3-pack—you’re missing a massive number of potential clients. That’s where Optimize My Firm steps in, helping attorneys build a content and SEO strategy grounded in trust, authority, and user experience.But what makes Lindsey’s approach unique is her stance on AI. While AI tools can assist with drafting, she warns against relying on them in legal marketing. Inaccurate legal content can have serious consequences, both reputationally and legally. Her firm ensures all content is created and reviewed by humans—so it’s not only optimized for Google, but also for accuracy, tone, and trust. She even shares a cautionary tale of a personal injury firm that published AI-generated case information, only to learn it was completely fabricated—putting their brand at risk.Optimize My Firm also stands out with its no-contract model. Lindsey explains that attorneys love this approach—it builds trust, keeps her team accountable, and allows for mutually beneficial, results-based relationships. This client-first mindset, paired with deep SEO expertise, has helped her firm become one of the most respected players in legal marketing today.About Lindsey BusfieldLindsey Busfield is one of the nation’s leading experts in legal SEO and content marketing. As the Vice President, COO, and partner at Optimize My Firm, she’s behind some of the most powerful law firm websites in the U.S. Lindsey is also the host of the award-winning Personal Injury Marketing Minute podcast, named one of the Best Legal Podcasts of 2024 by Attorney At Law Magazine. Her client-first, no-contract model has reshaped how law firms approach digital marketing.A seasoned entrepreneur from a family of trailblazers—her relatives founded Handsome Brook Farms, the largest organic pasture-raised egg provider in the U.S.—Lindsey brings innovation and authenticity to everything she does. Outside of work, she’s an avid pickleball player and proud mom of two young daughters.About Optimize My FirmOptimize My Firm is a boutique SEO agency that works exclusively with law firms. Their focus: helping attorneys generate more qualified leads by increasing online visibility and authority. With a no-contract policy, personalized service, and deep industry expertise, they’re redefining what SEO partnerships look like in the legal space.Links Mentioned in this EpisodeOptimize My Firm WebsitePersonal Injury Marketing Minute Podcast
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About The Thoughtful Entrepreneur

You’re gonna love this DAILY, commercial-free entrepreneur spotlight show. We feature CEOs and founders of 6-9 figure B2B companies. Agencies, coaches, consultants, and other leaders share not only their success stories - but their advice for business leaders focused on business growth. You’re going to hear real stories from real people all in 15-25 minutes time - perfect for your commute. On this podcast, your host, Josh Elledge encourages entrepreneurs to share not only their expertise but their stories and their hearts. We believe that every person has a unique message which can positively impact the world. Even YOU! If you’d like to be featured on The Thoughtful Entrepreneur, apply here: https://UpMyInfluence.com/guest/
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