The Thoughtful Entrepreneur

Building Authentic Connections: Daniel Andrews on Friendship, Hospitality, and Low-Barrier NetworkingIn this episode of The Thoughtful Entrepreneur, host Josh Elledge talks with Daniel Andrews, serial entrepreneur, connector, and mentor, about transforming both personal and professional relationships through authenticity and intentional hospitality. Daniel shares how small, simple actions—like inviting people over for dinner or scheduling short, genuine networking calls—can create powerful, lasting connections. His approach replaces the pressure of traditional networking with openness, generosity, and genuine curiosity, helping people connect more meaningfully in an increasingly digital world.Building Relationships Through Simplicity and HospitalityDaniel Andrews believes that hospitality is not about perfection but presence—making people feel seen, valued, and welcomed. He and his wife regularly host dinners to strengthen friendships, emphasizing that consistency and simplicity make connection sustainable. Whether in business or personal life, Daniel says hospitality creates space for trust, conversation, and belonging.Beyond hosting, Daniel encourages using technology to remove barriers to connection. He creatively uses Calendly for dinner invites, allowing friends to pick a convenient date and eliminating the friction of group planning. His philosophy: make it easy for people to say “yes” by lowering the stakes and setting clear expectations.Daniel also applies these principles to business networking. Instead of formal sales meetings, he prefers 20-minute, no-pressure “get-to-know-you” calls that prioritize relationship-building over pitching. He calls introductions the “currency of trust,” explaining that when you thoughtfully connect two people, you share your credibility and strengthen all three relationships. For Daniel, connection is not about collecting contacts—it’s about building a network of genuine, mutually beneficial relationships.About Daniel AndrewsDaniel Andrews is a seasoned entrepreneur, mentor, and relationship builder who champions authentic connection in both business and life. Known for his thoughtful approach to hospitality and low-barrier networking, Daniel has helped countless leaders and entrepreneurs strengthen relationships, expand their communities, and find deeper fulfillment through intentional connection.Links Mentioned in This EpisodeDaniel Andrews on LinkedInKey Episode HighlightsHospitality is about presence, not perfectionUse simple tools like Calendly to make invitations and connections effortlessBoundaries make connection easier, not harderReplace transactional networking with short, intentional conversationsThoughtful introductions build credibility and long-term trustConsistency and low-pressure gatherings are key to lasting relationshipsConclusionDaniel Andrews reminds us that meaningful connection doesn’t require grand gestures—it starts with small acts of intentionality. By simplifying invitations, embracing hospitality, and focusing on authenticity over perfection, we can nurture relationships that enrich both business and life. Genuine networking isn’t about volume; it’s about trust, presence, and care.🎧 More from UpMyInfluence:🎙️ Want to be featured on The Thoughtful Entrepreneur? Get your story in front of 50,000+ listeners.👉 Schedule your guest spot here.🤝 Consultant or agency doing 6+ figures? Let us introduce you to your next big client or referral partner.👉 Apply here to join our introductions program.📡 Thinking about launching your own podcast? We’ve built 250+ shows for leaders who now attract dream clients and collaborations weekly.👉 See how to get started.🚨 Find Your PodVerified Score!✅ Get two free podcast matches✅ Unlock a personalized guest plan✅ Earn media authority badges👉 Start here.📬 Subscribe to The Thoughtful Entrepreneur — new episodes daily with insights to grow your visibility, influence, and impact.

How Business Owners Can Scale and Thrive in the Age of AI: Insights from Dan GoodsteinIn this episode of The Thoughtful Entrepreneur, host Josh Elledge sits down with Dan Goodstein, Founder of The Business Therapist and President of IRPA AI, to explore how business owners can scale smarter and thrive amid rapid technological change. With years of experience in tech, marketing, media, and coaching, Dan offers practical advice on leveraging AI, building community, and creating systems that support sustainable growth in today’s fast-paced environment.Scaling Smarter in the AI EraDan emphasizes that too many business owners are working in their businesses rather than on them. He highlights the importance of stepping back, joining peer communities, and embracing outside accountability through coaching or masterminds. These practices create space for strategy, innovation, and balance—especially critical as AI reshapes how we work.AI, he explains, is now leveling the playing field for small and midsize businesses, giving them access to tools once reserved for large corporations. From AI-driven sales assistants to automated lead generation and CRM integrations, these technologies help streamline operations, enhance personalization, and improve ROI. Dan also encourages owners to adopt a “pilot-first” approach—testing tools on a small scale before company-wide implementation to ensure measurable results.Finally, Dan shares actionable strategies for using AI in sales, from automating outreach to personalizing follow-ups, while maintaining the human connection that drives lasting relationships. His advice is clear: start small, stay consistent, and focus on impact over volume. AI isn’t about replacing people—it’s about empowering them to spend more time on high-value, strategic work.About Dan GoodsteinDan Goodstein is the Founder of The Business Therapist, a platform helping entrepreneurs build scalable, resilient companies through coaching, peer networks, and strategic support. He also serves as President of IRPA AI, a global association focused on intelligent automation and digital transformation. Dan is the host of The Digital Leader Show and a frequent speaker on AI, business growth, and leadership innovation.About The Business TherapistThe Business Therapist provides business owners with the community, coaching, and resources they need to scale sustainably. Through mastermind groups, advisory programs, and peer-to-peer learning, the organization helps leaders step back from daily operations to focus on vision, systems, and growth strategy.Links Mentioned in This EpisodeThe Business Therapist WebsiteIRPA AI WebsiteDan Goodstein LinkedIn ProfileKey Episode HighlightsWhy every business owner needs community and strategy days.How AI tools are helping small businesses compete with large enterprises.Actionable ways to use AI in sales and marketing.Tips for choosing and integrating AI technologies effectively.The importance of focusing on sustainability, not just speed, in scaling.ConclusionDan Goodstein’s message is simple but powerful: you can’t scale by doing more—you scale by doing smarter. By stepping back, building support systems, and embracing AI-driven tools, business owners can transform the way they grow and operate. The future belongs to leaders who adapt, experiment, and use technology to amplify—not replace—the human touch in business.🎧 More from UpMyInfluence:🎙️ Want to be featured on The Thoughtful Entrepreneur? Get your voice in front of 50K+ listeners.👉 Schedule your guest spot here.🤝 Consultant doing 6+ figures? Let’s introduce you to your next big client, partner, or referral source.👉 See how here.📡 Thinking of launching your own podcast? We’ve helped 250+ leaders build high-impact shows that attract dream clients.👉 Start here.🚨 Get Your PodVerified Score! 🎯Discover how you rank as a podcast guest and get matched with shows that want your story.✅ 2 free podcast matches✅ Personalized guest dashboard✅ Media badges for credibility👉 Get started here.📬 Subscribe to The Thoughtful EntrepreneurDaily interviews and insights to grow your impact, visibility, and influence.

Building B2B Authority in the AI Era: Actionable Strategies from Kathleen Lucente of Red Fan CommunicationsIn this episode of The Thoughtful Entrepreneur, host Josh Elledge sits down with Kathleen Lucente, Founder and CEO of Red Fan Communications, to explore how B2B companies can build lasting authority and credibility in the AI-driven digital landscape. Kathleen shares her expertise in modern PR, brand storytelling, and thought leadership, offering a roadmap for high-growth companies to adapt to the era of zero-click searches and AI-powered visibility.Building B2B Authority in the Age of AIKathleen explains that traditional SEO strategies are no longer enough. With nearly 60% of Google searches ending without a click, brands must now focus on being discoverable through AI summaries, thought leadership, and digital authority—not just website traffic. She introduces her “Revenue Bridge” framework, built around three pillars: authority, credibility, and reputation. Authority opens doors, credibility converts, and reputation sustains long-term growth.To stand out in this new environment, Kathleen encourages businesses to refresh their brand narratives, ensuring they reflect what truly differentiates them in the market. She emphasizes multi-channel storytelling and the importance of developing multiple internal thought leaders who can each represent distinct aspects of a company’s expertise. The goal isn’t just visibility—it’s being referenced, quoted, and trusted by both humans and AI systems alike.Finally, she underscores that thought leadership is now a direct revenue driver. By educating your audience, securing media coverage, and engaging authentically online, companies can strengthen their digital footprint and boost conversions. Kathleen’s message is clear: in the AI era, influence happens before the click. B2B leaders must build public credibility that algorithms and audiences alike can recognize and trust.About Kathleen LucenteKathleen Lucente is the Founder and CEO of Red Fan Communications, a strategic communications firm based in Austin, Texas. With over two decades of experience, she has helped startups and Fortune 500 companies alike transform their PR and marketing strategies. Her firm specializes in brand narrative development, executive thought leadership, and communications strategies that drive measurable business growth.About Red Fan CommunicationsRed Fan Communications is a full-service strategic communications agency that helps high-growth B2B companies stand out in crowded markets. The firm partners with clients to elevate authority, strengthen reputation, and connect PR efforts directly to revenue. Through storytelling, content strategy, and media relations, Red Fan ensures brands remain relevant, discoverable, and influential in the AI-powered age.Links Mentioned in This EpisodeRed Fan Communications WebsiteKathleen Lucente LinkedInKey Episode Highlights60% of searches now end without a click—visibility requires AI optimization.Kathleen’s “Revenue Bridge” framework: authority, credibility, and reputation.How to refresh your brand narrative to attract modern B2B buyers.Why thought leadership drives both awareness and revenue.Practical steps to build multi-channel visibility and executive trust.ConclusionKathleen Lucente’s insights reveal that building authority today means adapting to the invisible influence of AI. By strengthening your brand’s narrative, establishing thought leadership, and connecting your PR strategy directly to revenue, your company can stay visible, trusted, and competitive in a zero-click world.🎧 More from UpMyInfluence:🎙️ Want to be featured on The Thoughtful Entrepreneur? Get your voice in front of 50K+ listeners. Schedule your guest spot here » https://go.upmyinfluence.com/podcast-guest🤝 Consultant doing 6+ figures? Let’s introduce you to your next big client, partner, or referral source. See how here » https://go.upmyinfluence.com/leader-intros📡 Thinking of launching your own podcast? We’ve built over 250 shows for leaders who now land dream guests (and clients) weekly. See the system here » https://upmyinfluence.com/book-podcast/🚨 What’s Your PodVerified Score? 🎯 Find out how you rank as a podcast guest — and get matched with hosts who actually want you.✅ 2 free podcast matches✅ Your own dashboard with warm-up plans✅ Media badges to showcase your guest authority✅ Priority access to Founders Club (limited to 100)👉 View the platform » https://app.podverified.com/start/📬 Subscribe to The Thoughtful EntrepreneurNew episodes daily to fuel your impact, visibility, and influence. Thanks for listening. Now go build something extraordinary!

Mastering Productivity: How to Treat Time Like Cash and Build Sustainable SuccessIn this episode of The Thoughtful Entrepreneur, host Josh Elledge sits down with Andrew Hartman, Founder and CEO of Time Boss, to explore a transformative approach to productivity. Andrew challenges the traditional hustle mindset, advocating instead for sustainable focus, intentional time management, and a “time-as-cash” philosophy. Their discussion reveals how leaders can achieve meaningful results by aligning energy, setting boundaries, and working smarter—not harder.Rethinking Productivity: Sustainability Over HustleAndrew explains that productivity isn’t about staying busy—it’s about getting the right things done. He encourages founders and executives to treat time like a limited resource, allocating it intentionally toward high-impact work. By setting a weekly “time budget,” business leaders can prioritize key results, prevent burnout, and maintain clarity around what truly matters.He also highlights the importance of sustainability over short-term sprints. Hustle can drive short bursts of progress, but without recovery, it leads to exhaustion. Instead, Andrew recommends anchoring to a steady baseline of work hours and recharging regularly to stay consistent. He reminds leaders that “boundaries aren’t restrictive—they’re empowering.” The discipline of protecting your time actually frees you to focus more deeply on creative and strategic work.Lastly, Andrew emphasizes the power of working in your zone of genius—the tasks that energize you and align with your strengths. Delegating draining work and using simple, familiar tools for time management (like a calendar or to-do list) can dramatically boost both productivity and satisfaction. True efficiency, he says, comes not from shiny new apps, but from consistent habits and clear priorities.About Andrew HartmanAndrew Hartman is the Founder and CEO of Time Boss, a productivity training company that helps entrepreneurs and executives design intentional, sustainable schedules for success. With years of experience coaching business owners, Andrew has developed frameworks like “time-as-cash” and “intentional time budgeting” to help clients achieve more by doing less—without burnout.About Time BossTime Boss is a coaching and training platform dedicated to helping professionals reclaim their time and focus on meaningful results. Through masterclasses, workshops, and personalized consulting, Time Boss equips individuals and teams to set clear priorities, align their energy with their goals, and create balance between work and life.Links Mentioned in this EpisodeTime Boss WebsiteAndrew Hartman LinkedIn ProfileKey Episode HighlightsWhy productivity is about results, not busynessHow to apply the “time-as-cash” framework for better boundariesCreating a weekly time budget for focus and clarityWorking in your “zone of genius” to maximize energy and impactWhy sustainable habits outperform constant hustleConclusionAndrew Hartman’s insights remind us that success isn’t built on endless work—it’s built on intention, focus, and balance. By treating time as your most valuable currency, setting boundaries, and operating in your strengths, you can create both sustainable productivity and a fulfilling lifestyle.🎧 More from UpMyInfluence:🎙️ Want to be featured on The Thoughtful Entrepreneur? Get your voice in front of 50K+ listeners. Schedule your guest spot here » https://go.upmyinfluence.com/podcast-guest🤝 Consultant doing 6+ figures? Let’s introduce you to your next big client, partner, or referral source. See how here » https://go.upmyinfluence.com/leader-intros📡 Thinking of launching your own podcast? We’ve built over 250 shows for leaders who now land dream guests (and clients) weekly. See the system here » https://upmyinfluence.com/book-podcast/🚨 What’s Your PodVerified Score? 🎯 Find out how you rank as a podcast guest — and get matched with hosts who actually want you.✅ 2 free podcast matches✅ Your own dashboard with warm-up plans✅ Media badges to showcase your guest authority✅ Priority access to Founders Club (limited to 100)👉 View the platform » https://app.podverified.com/start/📬 Subscribe to The Thoughtful EntrepreneurNew episodes daily to fuel your impact, visibility, and influence. Thanks for listening. Now go build something extraordinary!

Mastering B2B Lead Generation in the Age of AI: Expert Insights from Bill RiceIn this episode of The Thoughtful Entrepreneur, host Josh Elledge speaks with Bill Rice, founder of Bill Rice Strategy Group and Kaleidico. Bill shares his expertise in B2B marketing, lead generation, and the evolving role of AI in shaping how businesses attract and convert clients. Drawing from decades of experience in fintech, mortgage lending, and legal industries, Bill offers actionable insights for executives and agencies looking to thrive in a rapidly changing digital landscape.The New Rules of B2B Lead GenerationBill explains that B2B marketing has evolved beyond traditional methods like cold outreach and Google Ads. Today’s success depends on creating digital surface area—the online footprint of content, profiles, and engagement that helps AI and algorithms recognize your expertise. He emphasizes that consistent, clear messaging across blogs, websites, and social platforms allows both search engines and large language models (like ChatGPT) to identify and recommend your brand as an authority.A key part of Bill’s strategy is leveraging LinkedIn for executive visibility. He encourages business leaders to post regularly, engage thoughtfully, and use the platform as a stage for thought leadership. Sharing authentic stories, insights, and industry perspectives humanizes your brand while establishing credibility. This kind of visibility not only attracts potential clients but also builds trust and familiarity long before the sales conversation begins.Bill also discusses how AI and large language models are reshaping the buyer’s journey. AI-driven referrals are becoming more influential than traditional SEO, as they provide context-aware recommendations tailored to user needs. He advises business owners to ensure their digital content is well-structured, easy to interpret, and consistently reinforces their niche expertise. By combining thoughtful content creation, AI awareness, and genuine personal branding, companies can build scalable, first-party lead generation systems that produce sustainable results.About Bill RiceBill Rice is the Founder of Bill Rice Strategy Group and Kaleidico, two leading agencies specializing in B2B marketing and lead generation. With over 20 years of experience across finance, law, and senior living sectors, Bill helps executives and organizations develop first-party lead systems, optimize digital presence, and harness AI for measurable business growth. He is also the creator of The Executive Brief, a weekly newsletter featuring actionable insights for leaders navigating the intersection of marketing and technology.About Bill Rice Strategy GroupBill Rice Strategy Group is a marketing consultancy that helps businesses build first-party lead generation systems through strategy, content creation, and AI-driven insights. With a focus on long-term growth and client ownership of marketing assets, the firm empowers organizations to elevate their brand authority, generate consistent leads, and adapt to the rapidly evolving digital landscape.Links Mentioned in this EpisodeBill Rice Strategy GroupBill Rice LinkedIn ProfileThe Executive Brief NewsletterKey Episode HighlightsHow AI is reshaping B2B lead generation and client discoveryWhy digital surface area boosts visibility and credibilityThe power of LinkedIn for executive thought leadershipBuilding sustainable, first-party lead systemsBalancing professional ambition with personal passionConclusionBill Rice reminds us that successful B2B marketing is about clarity, consistency, and credibility. By expanding your digital presence, using AI strategically, and showing up authentically on platforms like LinkedIn, your business can stand out in a competitive market. And by pairing professional excellence with personal balance, you set the foundation for long-term success in both business and life.🎧 More from UpMyInfluence:🎙️ Want to be featured on The Thoughtful Entrepreneur? Get your voice in front of 50K+ listeners. Schedule your guest spot here » https://go.upmyinfluence.com/podcast-guest🤝 Consultant doing 6+ figures? Let’s introduce you to your next big client, partner, or referral source. See how here » https://go.upmyinfluence.com/leader-intros📡 Thinking of launching your own podcast? We’ve built over 250 shows for leaders who now land dream guests (and clients) weekly. See the system here » https://upmyinfluence.com/book-podcast/🚨 What’s Your PodVerified Score? 🎯 Find out how you rank as a podcast guest — and get matched with hosts who actually want you.✅ 2 free podcast matches✅ Your own dashboard with warm-up plans✅ Media badges to showcase your guest authority✅ Priority access to Founders Club (limited to 100)👉 View the platform » https://app.podverified.com/start/📬 Subscribe to The Thoughtful EntrepreneurNew episodes daily to fuel your impact, visibility, and influence. Thanks for listening. Now go build something extraordinary!

Realigning Your Business with Passion: Expert Insights from Kara DuffyIn this episode of The Thoughtful Entrepreneur, host Josh Elledge interviews Kara Duffy, CEO and Founder of KDCC International, who helps entrepreneurs and business owners realign their work with their passions and strengths. Kara shares how reconnecting with what you love can reignite purpose, boost profitability, and prevent burnout. Through her experience coaching creative leaders and building businesses, she offers clear, actionable steps to simplify operations, find your “zone of genius,” and create a company that feels as good as it performs.Building a Passion-Aligned BusinessKara believes that success starts with alignment—when your business reflects your purpose and energizes you daily. She explains that many entrepreneurs drift from their passion over time, taking on clients or projects that drain creativity and joy. Her “lemonade stand” philosophy encourages founders to strip back to what they do best and build from that foundation. By focusing on a single core offering, simplifying operations, and delegating distractions, business owners can regain clarity, increase profitability, and rediscover fulfillment in their work.Operating in your “zone of genius,” Kara says, means spending most of your time on high-value, joyful activities. She urges leaders to delegate or eliminate everything outside that zone and to audit weekly tasks for alignment. Through this lens, even niche businesses—like boutique creatives or specialists serving small, passionate audiences—can thrive when they stay authentic and focused. When clarity replaces clutter, it becomes easier to attract dream clients who align with your mission and values.Kara also emphasizes that business is a lifestyle, not just a job. She encourages entrepreneurs to design companies that support their personal rhythms and long-term well-being. Whether it’s taking “mini holidays” to recharge or fostering genuine client relationships, the goal is to create a sustainable balance. Her signature mantra—“Stop Selling, Start Sharing”—captures her belief that authenticity and generosity are the true engines of business growth. When you lead with purpose and share what you love, success follows naturally.About Kara DuffyKara Duffy is the CEO and Founder of KDCC International, a business coaching and consulting firm dedicated to helping entrepreneurs and creative leaders build businesses that are both profitable and purposeful. With extensive experience guiding founders through growth and realignment, Kara helps clients simplify, scale, and reconnect with their mission. She is also the author of Stop Selling, Start Sharing, a guide to authentic, purpose-driven business.About KDCC InternationalKDCC International empowers entrepreneurs and teams to build high-impact, passion-driven businesses through strategic coaching, workshops, and consulting. From clarity and culture to profitability and purpose, KDCC helps leaders align their operations with their vision—creating companies that thrive from the inside out.Links Mentioned in this EpisodeKDCC InternationalKara Duffy LinkedIn ProfileKey Episode HighlightsHow to simplify your business using the “lemonade stand” approachWhy working in your “zone of genius” leads to sustainable successHow to declutter your business like the KonMari MethodTurning your business into a lifestyle you loveBuilding authentic connections through sharing, not sellingConclusionAs Kara Duffy reminds us, business success isn’t just about growth—it’s about alignment. When your company reflects your passions, you lead with clarity, confidence, and creativity. By simplifying operations, embracing your strengths, and sharing your purpose authentically, you can create a business that supports both your goals and your joy.🎧 More from UpMyInfluence:🎙️ Want to be featured on The Thoughtful Entrepreneur? Get your voice in front of 50K+ listeners. Schedule your guest spot here » https://go.upmyinfluence.com/podcast-guest🤝 Consultant doing 6+ figures? Let’s introduce you to your next big client, partner, or referral source. See how here » https://go.upmyinfluence.com/leader-intros📡 Thinking of launching your own podcast? We’ve built over 250 shows for leaders who now land dream guests (and clients) weekly. See the system here » https://upmyinfluence.com/book-podcast/🚨 What’s Your PodVerified Score? 🎯 Find out how you rank as a podcast guest — and get matched with hosts who actually want you.✅ 2 free podcast matches✅ Your own dashboard with warm-up plans✅ Media badges to showcase your guest authority✅ Priority access to Founders Club (limited to 100)👉 View the platform » https://app.podverified.com/start/📬 Subscribe to The Thoughtful EntrepreneurNew episodes daily to fuel your impact, visibility, and influence. Thanks for listening. Now go build something extraordinary!

When Is Your Business Ready for a Fractional CFO? Expert Insights from Laresa McIntyreAs your business scales, the financial landscape becomes increasingly complex. Many founders find themselves overwhelmed by cash flow management, forecasting, and financial decision-making—realizing their passion alone isn’t enough to sustain growth. In this episode, host Josh Elledge interviews Laresa McIntyre, fractional CFO and Founder of Rockbridge CFO, who shares her insights on when to bring in a fractional CFO, how to prepare for that step, and how doing so can transform your business operations and confidence.The Right Time to Hire a Fractional CFOLaresa explains that a fractional CFO is a part-time financial executive who provides strategic planning, forecasting, and financial insight—without the cost of a full-time hire. Businesses typically benefit when revenue reaches the $1M–$2M mark or when decision-making starts to rely too heavily on gut instinct instead of data. She highlights clear signs that a company is ready for financial leadership: outgrowing basic tools like QuickBooks, feeling uncertain about profitability, or needing clarity around cash flow and personnel costs.A fractional CFO doesn’t just manage numbers—they partner with founders to bring order, foresight, and peace of mind. Laresa shares how implementing more detailed financial reporting and proactive cash flow forecasting helps business owners understand where their money is going, where it should go next, and how to allocate it efficiently. This support allows leaders to step back from financial stress and focus on strategy, growth, and innovation instead.For founders still below seven figures, Laresa recommends starting early by setting up robust accounting systems and forecasting tools. Preparation ensures a fractional CFO can deliver maximum value once engaged. By building these systems in advance, founders avoid reactive decisions and gain clarity on how each financial move impacts long-term scalability.About Laresa McIntyreLaresa McIntyre is the Founder and Fractional CFO at Rockbridge CFO, where she helps businesses gain financial clarity, improve profitability, and scale strategically. With years of experience supporting founders and executive teams, she specializes in transforming financial chaos into actionable growth strategies.About Rockbridge CFORockbridge CFO provides strategic financial leadership for growing companies through fractional CFO services. The firm focuses on forecasting, profitability analysis, and cash flow management—empowering business owners to make confident, data-driven decisions without the expense of a full-time CFO.Links Mentioned in this EpisodeRockbridge CFOLaresa McIntyre LinkedIn ProfileKey Episode HighlightsSigns your business is ready for a fractional CFOHow financial forecasting improves decision-makingCommon gaps in accounting systems for scaling companiesThe emotional and strategic benefits of CFO partnershipHow to prepare your financial foundation before reaching seven figuresConclusionHiring a fractional CFO isn’t just about managing your finances—it’s about reclaiming your time, focus, and confidence as a leader. As Laresa McIntyre explains, the right time to bring in a CFO is when you’re ready to grow with clarity and strategy instead of stress and guesswork. Whether your business is at $500K or $5M, proactive financial leadership can set the foundation for sustainable, scalable success.🎧 More from UpMyInfluence:🎙️ Want to be featured on The Thoughtful Entrepreneur? Get your voice in front of 50K+ listeners. Schedule your guest spot here » https://go.upmyinfluence.com/podcast-guest🤝 Consultant doing 6+ figures? Let’s introduce you to your next big client, partner, or referral source. See how here » https://go.upmyinfluence.com/leader-intros📡 Thinking of launching your own podcast? We’ve built over 250 shows for leaders who now land dream guests (and clients) weekly. See the system here » https://upmyinfluence.com/book-podcast/🚨 What’s Your PodVerified Score? 🎯 Find out how you rank as a podcast guest — and get matched with hosts who actually want you.✅ 2 free podcast matches✅ Your own dashboard with warm-up plans✅ Media badges to showcase your guest authority✅ Priority access to Founders Club (limited to 100)👉 View the platform » https://app.podverified.com/start/📬 Subscribe to The Thoughtful EntrepreneurNew episodes daily to fuel your impact, visibility, and influence. Thanks for listening. Now go build something extraordinary!

Navigating the 2025 SMB Landscape: Proactive Tax Strategies and Expert Insights from Adam WilliamsSmall and medium-sized business owners are facing unprecedented challenges in 2025, from rapid legal changes to AI-driven disruption. In a recent episode, Josh Elledge sat down with Adam Williams, author and Co-founder of Pennywise Tax Strategies, to explore actionable strategies for SMB founders navigating complex tax, legal, and operational environments. Adam shared insights on proactive tax planning, leveraging expert advisors, and adapting to technological changes to help businesses thrive in an increasingly dynamic landscape.The Power of Proactive Tax PlanningAdam emphasizes that reactive tax preparation is no longer sufficient for SMBs looking to maximize profits and future-proof their businesses. Forward-thinking strategies like auditing profit and loss statements, employing family members, leveraging the Augusta Rule, choosing the right business entity, and utilizing cost segregation can save businesses significant money while maintaining compliance. He also highlights the importance of ongoing education and expert advisors, ensuring owners can confidently navigate new laws, AI integration, and changing economic conditions.Proactive planning goes beyond minimizing taxes—it’s about optimizing operations and leveraging every available advantage. SMB owners can use these strategies to automate processes, structure their teams effectively, and ensure every deduction, credit, or exemption is captured. Adam’s guidance demonstrates how combining thoughtful planning with expert support allows businesses to remain agile, profitable, and competitive in 2025 and beyond.Entrepreneurs who implement these strategies not only reduce risk but also position their businesses for sustainable growth. From cost-saving opportunities to AI-driven efficiency improvements, the insights Adam shared provide a clear roadmap for SMB founders seeking long-term success. By taking a proactive approach, business owners can reclaim control over their finances, optimize operations, and confidently scale their enterprises.About Adam WilliamsAdam Williams is the Co-founder of Pennywise Tax Strategies and a seasoned author focused on actionable tax and business advice for small and medium-sized enterprises. With deep expertise in tax planning, business law, and strategic consulting, Adam empowers SMB owners to make informed decisions that maximize profits and minimize risk.About Pennywise Tax StrategiesPennywise Tax Strategies helps small and medium businesses implement proactive tax planning, optimize deductions, and leverage financial strategies to grow efficiently. Their team specializes in forward-looking solutions that combine expert knowledge with practical, actionable tactics for entrepreneurs navigating a rapidly evolving business environment.Links Mentioned in this EpisodePennywise Tax StrategiesAdam Williams LinkedInKey Episode HighlightsHow SMBs can navigate complex tax and legal changes in 2025Strategies for proactive tax planning and financial optimizationLeveraging expert advisors and mastering profit and loss statementsTips for employing family members, leveraging the Augusta Rule, and entity selectionInsights on cost segregation and maximizing deductions for SMBsConclusionThe 2025 SMB environment demands proactive planning, strategic partnerships, and a keen understanding of tax and operational opportunities. Adam Williams’ insights provide a roadmap for entrepreneurs seeking to thrive amid uncertainty by optimizing finances, leveraging expert guidance, and positioning their businesses for sustainable growth. By taking actionable steps today, SMB owners can maximize profits, minimize risk, and ensure long-term success.🎧 More from UpMyInfluence:🎙️ Want to be featured on The Thoughtful Entrepreneur? Get your voice in front of 50K+ listeners. Schedule your guest spot here » https://go.upmyinfluence.com/podcast-guest🤝 Consultant doing 6+ figures? Let’s introduce you to your next big client, partner, or referral source. See how here » https://go.upmyinfluence.com/leader-intros📡 Thinking of launching your own podcast? We’ve built over 250 shows for leaders who now land dream guests (and clients) weekly. See the system here » https://upmyinfluence.com/book-podcast/🚨 What’s Your PodVerified Score? 🎯 Find out how you rank as a podcast guest — and get matched with hosts who actually want you.✅ 2 free podcast matches✅ Your own dashboard with warm-up plans✅ Media badges to showcase your guest authority✅ Priority access to Founders Club (limited to 100)👉 View the platform » https://app.podverified.com/start/📬 Subscribe to The Thoughtful EntrepreneurNew episodes daily to fuel your impact, visibility, and influence. Thanks for listening. Now go build something extraordinary!

Growth Through Acquisition: Lessons from Navy Veteran and Entrepreneur Gary MacDermidEntrepreneurship often requires both discipline and strategic vision, and few embody that combination like Gary MacDermid—a Navy veteran turned successful business acquirer, investor, and author. In a recent episode of The Thoughtful Entrepreneur, host Josh Elledge sat down with Gary to discuss his journey from military service to civilian business leadership, offering actionable strategies for veterans and entrepreneurs alike. This post distills key insights from the conversation, focusing on growth through acquisition, creative financing, and the importance of intentional goal-setting.Accelerating Growth Through Acquisition and Strategic Goal-SettingGary emphasizes that acquiring businesses—rather than relying solely on organic growth—can rapidly scale revenue, talent, and operational capacity. By identifying complementary businesses and overlaying high-value services, entrepreneurs can unlock immediate opportunities and enhance client value. Creative financing options, such as seller financing, SBA loans, and private investors, make acquisitions accessible even without deep upfront capital, allowing business owners to pursue strategic growth without overextending resources.Veterans, in particular, benefit from leveraging military discipline and intentional goal-setting, which Gary details in his book Set Your Own Goals or Someone Else Will. He recommends defining clear milestones, breaking down actionable steps, and seeking mentorship or peer accountability to navigate complex business decisions effectively. Beyond acquisition strategies, Gary stresses the importance of cultural integration and communication to ensure smooth transitions for both clients and staff, ensuring that growth is sustainable rather than just rapid.For all entrepreneurs, Gary underscores the value of overlaying high-ticket services on acquired businesses, continuously learning from new markets, and integrating processes that drive efficiency. Whether transitioning from military service or expanding an existing business, the principles of acquisition, strategic financing, and clear goal-setting serve as powerful levers to accelerate success.About Gary MacDermidGary MacDermid is a Navy veteran, investor, business acquirer, and author of Set Your Own Goals or Someone Else Will. He leverages his military experience and entrepreneurial expertise to help veterans, career changers, and business leaders strategically grow and scale their businesses.About Gary’s CompanyGary specializes in growth through acquisition, creative financing, and advisory services that empower entrepreneurs to expand efficiently while maintaining operational and cultural integrity. His methods help businesses unlock hidden value and pursue strategic opportunities with confidence.Links Mentioned in This EpisodeGary MacDermid Website: https://garymacdermid.comBook: Set Your Own Goals or Someone Else WillKey Episode HighlightsGary’s journey from Navy service to entrepreneurshipBenefits of growth through acquisition over organic growthStep-by-step approach to buying and integrating a businessCreative financing strategies: seller financing, SBA loans, private investorsOverlaying high-ticket services to maximize revenueIntentional goal-setting framework for veterans and career changersConclusionGary MacDermid’s insights demonstrate that disciplined strategy, smart acquisition, and intentional goal-setting are essential tools for accelerating growth. By leveraging military experience, creative financing, and high-value service overlays, entrepreneurs and veterans alike can unlock sustainable business success.🎧 More from UpMyInfluence:🎙️ Want to be featured on The Thoughtful Entrepreneur? Get your voice in front of 50K+ listeners. Schedule your guest spot here » https://go.upmyinfluence.com/podcast-guest🤝 Consultant doing 6+ figures? Let’s introduce you to your next big client, partner, or referral source. See how here » https://go.upmyinfluence.com/leader-intros📡 Thinking of launching your own podcast? We’ve built over 250 shows for leaders who now land dream guests (and clients) weekly. See the system here » https://upmyinfluence.com/book-podcast/🚨 What’s Your PodVerified Score? 🎯 Find out how you rank as a podcast guest — and get matched with hosts who actually want you.✅ 2 free podcast matches✅ Your own dashboard with warm-up plans✅ Media badges to showcase your guest authority✅ Priority access to Founders Club (limited to 100)👉 View the platform » https://app.podverified.com/start/📬 Subscribe to The Thoughtful EntrepreneurNew episodes daily to fuel your impact, visibility, and influence. Thanks for listening. Now go build something extraordinary!

Mastering Social Media Advertising in 2024: Expert Insights from Madison Hollimon of Mad Marketing HouseIn the rapidly evolving world of social media marketing, staying ahead of platform trends, AI tools, and audience expectations is critical. In a recent podcast episode, Josh Elledge interviewed Madison Hollimon, CEO and Founder of Mad Marketing House, who shared her expertise in content creation, paid advertising, and user-generated content (UGC) strategies. This post breaks down key insights and actionable tips for businesses looking to optimize their social media campaigns and maximize engagement in 2024.Navigating Paid Ads, UGC, and AI in Social Media MarketingMadison emphasizes that effective social media marketing requires blending creativity with data-driven strategy. By leveraging authentic UGC, businesses can increase engagement and build trust, while paid advertising helps amplify reach and drive conversions. Combining AI tools with human oversight ensures campaigns are optimized efficiently without losing the personal touch that resonates with audiences.She also highlights the differences between B2B and B2C advertising, explaining that B2B campaigns require precise targeting on platforms like LinkedIn, while B2C campaigns rely on broad reach across Meta and TikTok. Madison stresses that paid advertising is most effective when aligned with strategic goals, proper budgeting, and ongoing monitoring, emphasizing that quick wins come from smart investments rather than guesswork.Finally, Madison encourages brands to embrace authenticity and storytelling while adopting AI and automation cautiously. Keeping content relatable and visually appealing ensures campaigns stand out amid algorithm changes and evolving consumer behavior. Businesses that blend technology with creativity are positioned to achieve higher ROI and long-term brand loyalty.About Madison HollimonMadison Hollimon is the CEO and Founder of Mad Marketing House, a full-service social media marketing agency specializing in content creation, paid advertising, and strategic campaigns for both B2B and B2C brands. With a focus on combining creativity, strategy, and data, Madison helps businesses scale their social presence and engage audiences effectively.About Mad Marketing HouseMad Marketing House is a creative agency that helps businesses craft authentic content and implement high-performing social media campaigns. Leveraging UGC, AI tools, and strategic paid advertising, the agency works with entrepreneurs, product-based businesses, and personal brands to maximize engagement, conversions, and ROI.Links Mentioned in this EpisodeMad Marketing House WebsiteMadison Hollimon LinkedInInstagram: @madmarketinghouseKey Episode HighlightsThe importance of authentic user-generated content for engagement and trust.How AI and automation can optimize campaigns without replacing human oversight.Strategic differences between B2B and B2C social media advertising.Tips for paid ad budgeting, targeting, and monitoring to maximize ROI.Future trends in social media marketing and content strategy.ConclusionSocial media marketing in 2024 demands a balance of creativity, strategy, and technological savvy. Madison Hollimon’s insights highlight how brands can leverage UGC, paid advertising, and AI tools to drive engagement and achieve measurable results while staying authentic and audience-focused.🎧 More from UpMyInfluence:🎙️ Want to be featured on The Thoughtful Entrepreneur? Get your voice in front of 50K+ listeners. Schedule your guest spot here » https://go.upmyinfluence.com/podcast-guest🤝 Consultant doing 6+ figures? Let’s introduce you to your next big client, partner, or referral source. See how here » https://go.upmyinfluence.com/leader-intros📡 Thinking of launching your own podcast? We’ve built over 250 shows for leaders who now land dream guests (and clients) weekly. See the system here » https://upmyinfluence.com/book-podcast/🚨 What’s Your PodVerified Score? 🎯 Find out how you rank as a podcast guest — and get matched with hosts who actually want you.✅ 2 free podcast matches✅ Your own dashboard with warm-up plans✅ Media badges to showcase your guest authority✅ Priority access to Founders Club (limited to 100)👉 View the platform » https://app.podverified.com/start/📬 Subscribe to The Thoughtful EntrepreneurNew episodes daily to fuel your impact, visibility, and influence. Thanks for listening. Now go build something extraordinary!