The Thoughtful Entrepreneur

Mastering Disaster Preparedness and Business Continuity: Expert Insights from Kenneth EdmondsIn this episode of The Thoughtful Entrepreneur, host Josh Elledge sits down with Kenneth Edmonds, CEO & Founder of 22nd Century Management, to explore the critical importance of disaster preparedness and business continuity. Kenneth shares his extensive experience helping companies safeguard operations, prevent catastrophic losses, and create actionable strategies for resilience. From cybersecurity threats to natural disasters, this conversation is a powerful wake-up call for any business owner who wants to protect their people, profits, and reputation.Why Disaster Planning Is Non-NegotiableKenneth emphasizes that proactive disaster planning is not just a safety net—it’s a business imperative. With 40% of businesses never reopening after a major disaster, the stakes couldn’t be higher. He illustrates this with the story of a limousine company that survived 9/11 thanks to a well-executed plan, gaining a competitive advantage while others faltered. Kenneth urges leaders to treat disaster planning as an ongoing process that builds organizational readiness and agility.He breaks down how companies can identify critical functions, assess vulnerabilities, and use tools like AI to inform risk assessments. Kenneth also highlights often-overlooked areas, such as untested data backups and vague communication protocols, that can make or break recovery efforts. His advice: test, revise, and engage your team regularly to ensure your plan is both comprehensive and executable.From creating incident command structures to running simulation drills, Kenneth lays out a roadmap that transforms disaster planning from a dusty binder into a dynamic, life-saving strategy. His expert insights help leaders prepare for the worst while empowering their teams to act with clarity and confidence when crises hit.About Kenneth Edmonds:Kenneth Edmonds is the CEO & Founder of 22nd Century Management and a seasoned disaster preparedness expert. With decades of experience, Kenneth has helped businesses develop comprehensive continuity plans, mitigate risk, and navigate crises with confidence. His work integrates AI-driven assessments, team training, and best-in-class frameworks to help organizations stay resilient in the face of any disruption.About 22nd Century Management:22nd Century Management specializes in disaster preparedness, business continuity planning, and risk mitigation for businesses of all sizes. With a hands-on, customized approach, the firm helps clients protect their operations, empower their teams, and stay competitive even in times of crisis.Links Mentioned in this Episode:Kenneth Edmonds on LinkedIn22nd Century Management WebsiteEpisode Highlights:40% of businesses never reopen after a major disasterKey elements of a comprehensive disaster planReal-world case study: A limo company’s survival post-9/11Why cybersecurity insurance and tested backups are crucialBuilding incident command structures and running simulationsConclusionKenneth Edmonds delivers a compelling message: disaster planning isn’t optional, it’s essential. His strategies help businesses not only survive the unexpected but emerge stronger and more competitive. This episode is a must-listen for leaders ready to safeguard their future with clarity, confidence, and action.Apply to be a Guest on The Thoughtful Entrepreneur: https://go.upmyinfluence.com/podcast-guestMore from UpMyInfluence:We are actively booking guests for our The Thoughtful Entrepreneur. Schedule HERE.Are you a 6-figure consultant? I’ve got high-level intros for you. Learn more here.What is your #1 Lead Generation BLOCKER? Take my free quiz here.Want to learn more about all the podcasts managed by UpMyInfluence? Opt in here.Don’t forget to subscribe to The Thoughtful Entrepreneur and thank you for listening. Tune in next time!

How Paralex is Revolutionizing Legal Services for Small Business Owners: Insights from the Podcast with Stephen CandelmoIn this episode of The Thoughtful Entrepreneur, host Josh Elledge interviews Stephen Candelmo, CEO of Paralex, about transforming how small businesses access legal services. Stephen shares how his passion for both law and technology led to founding Paralex, a platform that blends AI efficiency with human legal expertise. Listeners will also enjoy a unique personal twist—Stephen’s love for sourdough baking, which serves as a powerful metaphor for entrepreneurship.Legal Support, AI Innovation, and the Small Business AdvantageStephen opens the conversation by discussing his deep passion for cooking—particularly sourdough—and how its patience and care reflect the same mindset needed in running a business. This leads into a broader discussion about the common legal hurdles small business owners face, from high costs to confusing language and delayed service.Paralex addresses these challenges through a hybrid model. AI handles client intake and document preparation quickly and affordably, while licensed attorneys review and finalize every document to ensure legal integrity. This approach offers transparency, fixed pricing, and a human touch—making legal support accessible and reliable for entrepreneurs.Stephen walks listeners through the user journey on the Paralex platform, from submitting a request to receiving attorney-reviewed documents. He also offers valuable advice on what to look for in legal tech platforms and why having the right legal foundation early on is crucial for long-term success.About Stephen Candelmo:Stephen Candelmo is the Founder and CEO of Paralex and a seasoned corporate attorney with nearly three decades of experience. His mission is to democratize legal access for small businesses by merging cutting-edge technology with legal professionalism. Through Paralex, Stephen is making legal services faster, more affordable, and approachable for entrepreneurs.About Paralex:Paralex is an AI-powered legal platform designed to provide small business owners with quick, affordable, and attorney-reviewed legal documents. Combining automation and professional oversight, Paralex simplifies legal services without compromising quality.Links Mentioned in this Episode:Stephen Candelmo on LinkedInParalex WebsiteEpisode Highlights:How sourdough baking relates to business and legal careThe biggest legal hurdles for small business ownersHow AI and human expertise combine on the Paralex platformA step-by-step look at how Paralex worksTips for choosing and using legal tech as a small businessConclusionStephen Candelmo shares a compelling vision for the future of legal services—one where small businesses are no longer priced out or left confused by legal complexities. By combining advanced AI with expert legal review, Paralex sets a new standard for accessibility and quality in the legal tech space.Apply to be a Guest on The Thoughtful Entrepreneur: https://go.upmyinfluence.com/podcast-guestMore from UpMyInfluence:We are actively booking guests for our The Thoughtful Entrepreneur. Schedule HERE.Are you a 6-figure consultant? I’ve got high-level intros for you. Learn more here.What is your #1 Lead Generation BLOCKER? Take my free quiz here.Want to learn more about all the podcasts managed by UpMyInfluence? Opt in here.Don’t forget to subscribe to The Thoughtful Entrepreneur and thank you for listening. Tune in next time!

Finding Purpose and Fulfillment in Midlife: Insights from Adam Landrum of "Made to Matter"In this episode of The Thoughtful Entrepreneur, host Josh Elledge speaks with Adam Landrum, Founder & Coach of Made to Matter. Adam opens up about his own midlife journey and how he now helps men redefine success, discover purpose, and create lives filled with meaning and adventure. Drawing from his coaching experience and his book, The Life That Matters Manifesto, Adam provides actionable steps for men ready to move beyond the midlife "crisis" into a season of personal transformation.Redefining Identity, Embracing Vulnerability, and Creating a Life That MattersAdam Landrum challenges the outdated notion that midlife signifies decline, sharing how selling his business triggered a personal identity shift that ultimately opened the door to deeper meaning. He invites men to explore their true desires and define success beyond titles and achievements. For Adam, midlife isn’t an ending—it’s a launchpad for reinvention.He emphasizes the growing cultural embrace of vulnerability and emotional openness among men. Through tools like journaling, coaching, and honest conversations, Adam encourages emotional literacy and connection. These elements are essential to navigating personal transformation with clarity and courage.Central to Adam’s message is his purpose-vision-mission framework featured in The Life That Matters Manifesto. He urges men to find alignment through meaningful work, personal adventure, and intentional action. Whether it’s launching a project or taking a trip, fulfillment starts with defining what truly matters and taking bold steps in that direction.About Adam Landrum:Adam Landrum is a seasoned executive coach with over 1,000 coaching hours. Since 2016, he has guided leaders ranging from Fortune 100 executives to entrepreneurs. With two executive coaching certifications, he specializes in helping men in their second half of life find more purpose, fulfillment, and the courage to pursue their vision. He is the author of The Life That Matters Manifesto: 11 Principles to Know and Commit to Live a Life That Matters, a guide to living with purpose and meaning. After selling his advertising agency in 2023, Adam dedicated himself fully to coaching, using his business background to help men boldly step into their next chapter.About Made to Matter:Made to Matter is a coaching and resource platform designed to help men in midlife rediscover purpose, meaning, and adventure. Through structured coaching, books, and workbooks, Adam Landrum equips clients with the tools to build lives filled with clarity and impact.Links Mentioned in this Episode:Adam Landrum on LinkedInMade to Matter WebsiteEpisode Highlights:Redefining identity after a career shift or retirementEmbracing vulnerability and emotional intelligence for growthDeveloping purpose, vision, and mission statementsThe role of adventure and meaningful work in midlifeAdam’s 13-week coaching program and personal transformation processConclusionJosh and Adam's conversation sheds light on the rich possibilities that midlife offers. From reclaiming identity to embracing personal growth and adventure, Adam’s coaching empowers men to live lives aligned with their core values and deeper desires. If you're ready to move beyond routine and reconnect with what really matters, this episode offers a path to purpose and fulfillment.Apply to be a Guest on The Thoughtful Entrepreneur: https://go.upmyinfluence.com/podcast-guestMore from UpMyInfluence:We are actively booking guests for our The Thoughtful Entrepreneur. Schedule HERE.Are you a 6-figure consultant? I’ve got high-level intros for you. Learn more here.What is your #1 Lead Generation BLOCKER? Take my free quiz here.Want to learn more about all the podcasts managed by UpMyInfluence? Opt in here.Don’t forget to subscribe to The Thoughtful Entrepreneur and thank you for listening. Tune in next time!

Empowering Women in Wealth: Actionable Financial Strategies from Michelle TaylorIn this episode of The Thoughtful Entrepreneur, host Josh Elledge speaks with Michelle Taylor, Founder of Women in Wealth. Michelle shares practical, actionable strategies that help women business owners take control of their finances, maximize tax efficiency, and build long-term wealth. Her insights, grounded in real-world experience, highlight the importance of education, community, and redefining wealth on your own terms.Financial Clarity and Confidence for Women EntrepreneursMichelle Taylor opens the conversation by reflecting on her travels through Spain—an experience that underscored how true wealth isn’t just about numbers, but how we experience life. She describes immersing herself in authentic local culture and using that perspective to reframe how we define financial success. For Michelle, travel highlights the importance of aligning spending with personal values, a theme central to her approach in working with women entrepreneurs.This insight carries over into the mission of Women in Wealth, the financial advisory firm Michelle founded to empower women to take control of their finances with confidence. With a client base made up of 95% entrepreneurs, Michelle understands the nuanced challenges women face in balancing personal and business wealth. She emphasizes that business owners should view their enterprises not as separate from wealth-building—but as the foundation of it.Throughout the episode, Michelle breaks down complex financial concepts into actionable strategies, including how to structure investments, optimize tax savings, and use family involvement for long-term planning. She reinforces the importance of education and community in closing the financial confidence gap for women. By fostering a safe space where women can ask questions, share experiences, and connect with vetted professionals, Michelle provides a unique, holistic approach to personal and business finance.About Michelle Taylor:Michelle Taylor is the Founder of Women in Wealth, where she helps women business owners gain financial clarity, optimize their wealth strategies, and build a supportive community. She blends expert guidance with a human-first approach, helping clients align their financial decisions with their personal values and business goals.About Women in Wealth:Women in Wealth is a financial advisory and education firm dedicated to empowering women entrepreneurs. Through workshops, strategic planning, and a network of vetted professionals, Women in Wealth equips clients with the tools and confidence to take charge of their financial future.Links Mentioned in this Episode:Michelle Taylor on LinkedInWomen in Wealth WebsiteTalk Wealthy to Me PodcastEpisode Highlights:Travel as a metaphor for aligning spending with valuesThe mission behind Women in Wealth and its focus on women entrepreneursTax-smart strategies like the Augusta Rule and paying your childrenRedefining wealth through personal values and small luxuriesThe importance of financial community and continued educationConclusionJosh and Michelle’s conversation is a valuable roadmap for women entrepreneurs seeking to grow, protect, and redefine their wealth. By blending technical knowledge with emotional intelligence, Michelle equips listeners to make empowered, aligned financial decisions. Whether you’re just starting or scaling your business, this episode offers clear steps and inspiration to move forward with confidence.Apply to be a Guest on The Thoughtful Entrepreneur: https://go.upmyinfluence.com/podcast-guestMore from UpMyInfluence:We are actively booking guests for our The Thoughtful Entrepreneur. Schedule HERE.Are you a 6-figure consultant? I’ve got high-level intros for you. Learn more here.What is your #1 Lead Generation BLOCKER? Take my free quiz here.Want to learn more about all the podcasts managed by UpMyInfluence? Opt in here.Don’t forget to subscribe to The Thoughtful Entrepreneur and thank you for listening. Tune in next time!

Taking Action and Overcoming Procrastination: Insights from Coach Lori Anne De Iulio CasdiaIn this episode of The Thoughtful Entrepreneur, host Josh Elledge speaks with Coach Lori Anne De Iulio Casdia, Coach & Strategist and the founder of LDC Strategies. Coach Lori Anne offers a powerful and relatable framework for breaking free from procrastination, embracing your unique gifts, and taking meaningful action toward your personal and professional goals. Her advice blends actionable strategies, mindset shifts, and real-life examples to help listeners navigate chaos with clarity and courage.Stepping Into Action with Clarity and ConfidenceCoach Lori Anne opens the conversation with a personal story about learning to ride a motorcycle—an act that became a metaphor for facing fear and moving forward. She emphasizes that fear is often a signal of growth, and taking the first step (no matter how small) is the key to overcoming inertia. From visualizing success to setting public intentions, she lays out simple yet effective ways to gain momentum.She also speaks about the importance of uncovering and celebrating your unique gifts, rather than conforming to outside expectations. Lori Anne encourages listeners to focus on their strengths, seek feedback, and let go of comparison. Authenticity, she says, is what attracts the right opportunities and people.From there, she dives into the psychology of procrastination, calling out the “Super Bowl Syndrome” of jumping from task to task without finishing any. Through small deadlines, single-tasking, and accountability tracking, she provides practical tools to stop procrastinating and start progressing. Her insights are a masterclass in aligning your priorities and energy with your long-term goals.About Coach Lori Anne De Iulio Casdia:Coach Lori Anne De Iulio Casdia is a Transformational Success Coach & Strategist, #1 International Best-Selling and Award-Winning Author, and radio personality of Healthy Lifestyle with Lori Anne. As the founder of LDC Strategies, she empowers individuals and organizations to take bold, aligned action and soar to success. Known for her dynamic, interactive speaking style, Lori Anne delivers transformative experiences grounded in mindset, vision, and authentic leadership.About LDC Strategies:LDC Strategies offers professional coaching and consulting services focused on helping individuals and organizations clarify their vision, build confidence, and execute purpose-driven strategies. Coach Lori Anne blends practical guidance with mindset work to support clients in creating impactful, fulfilling success.Links Mentioned in this Episode:Coach Lori Anne on LinkedInLDC Strategies WebsiteEpisode Highlights:A personal story on facing fear and taking the first step toward actionHow to uncover and leverage your unique gifts and strengthsDisrupting procrastination with practical tools and mindset shiftsThe importance of priority management and a “not-to-do” listNavigating chaos by focusing on what’s within your controlConclusionJosh and Lori Anne’s conversation is a motivational blueprint for anyone stuck in indecision or overwhelmed by distractions. With insights on overcoming fear, celebrating individuality, and disrupting procrastination, Coach Lori Anne empowers listeners to reclaim their momentum. Whether you're building a business or pursuing personal growth, her approach will help you step forward with confidence and clarity.Apply to be a Guest on The Thoughtful Entrepreneur: https://go.upmyinfluence.com/podcast-guestMore from UpMyInfluence:We are actively booking guests for our The Thoughtful Entrepreneur. Schedule HERE.Are you a 6-figure consultant? I’ve got high-level intros for you. Learn more here.What is your #1 Lead Generation BLOCKER? Take my free quiz here.Want to learn more about all the podcasts managed by UpMyInfluence? Opt in here.Don’t forget to subscribe to The Thoughtful Entrepreneur and thank you for listening. Tune in next time!

Navigating the Evolving Landscape of Cybersecurity and AI: In-Depth Insights from Rick JordanIn this episode of The Thoughtful Entrepreneur, host Josh Elledge talks with Rick Jordan, speaker, coach, and Founder & CEO of ReachOut Technology. Rick unpacks the rapidly changing worlds of cybersecurity and artificial intelligence, and how business leaders can stay proactive in protecting their organizations. With practical advice, personal stories, and big-picture strategy, Rick shares what it really takes to succeed—and stay secure—in a digital-first world.Exploring the Human and Technical Sides of CybersecurityThe conversation begins on a personal note as Rick shares how technology, particularly gaming, creates meaningful connections with his daughter. Josh adds how gaming fosters deeper bonds in his own family, highlighting the positive impact of shared digital experiences. This sets the stage for the bigger conversation—how the human element influences technology, cybersecurity, and communication.Rick explains how ReachOut Technology addresses cybersecurity for small and mid-sized businesses by offering enterprise-level solutions through a clear and trusted brand. He shares his unique growth-by-acquisition strategy, integrating smaller IT service providers to create a unified, scalable, and culturally aligned company. He also outlines how his team helps SMBs implement practical steps like MFA, employee security training, and credit freezes to reduce risks from modern cyber threats.A consistent theme throughout the episode is the power of communication—whether between parents and kids or tech leaders and their teams. Rick emphasizes that cybersecurity is as much about people as it is about technology. His mission is to equip leaders with both the technical knowledge and communication skills needed to safeguard their organizations in an AI-driven world.About Rick Jordan:Rick Jordan is a nationally recognized speaker, coach, and cybersecurity expert. As the CEO of ReachOut Technology, Rick is committed to simplifying cybersecurity for SMBs and helping leaders take practical steps to protect their teams. He’s also a media personality and author, using his platform to educate and inspire through books, interviews, and keynotes.About ReachOut Technology:ReachOut Technology is a managed IT and cybersecurity company that provides enterprise-level protection and support to small and mid-sized businesses. Through a unique acquisition strategy and customer-focused approach, ReachOut is creating a household name in the fragmented IT space.Links Mentioned in this Episode:Rick Jordan's WebsiteRick Jordan on LinkedInReachOut Technology WebsiteEpisode Highlights:The personal and professional ways technology fosters connectionHow ReachOut Technology is scaling through strategic acquisitionsThe biggest cybersecurity threats and why phishing remains a top concernWhy MFA and security awareness training are no longer optionalThe importance of communication in driving cultural change around cybersecurityConclusionJosh and Rick’s conversation bridges the gap between technology and human behavior. From protecting digital assets to creating stronger family connections, Rick emphasizes the need for both technical tools and empathetic leadership. Business leaders will walk away from this episode with clear, actionable strategies to strengthen their cybersecurity posture and foster more connected, secure teams.Apply to be a Guest on The Thoughtful Entrepreneur: https://go.upmyinfluence.com/podcast-guestMore from UpMyInfluence:We are actively booking guests for our The Thoughtful Entrepreneur. Schedule HERE.Are you a 6-figure consultant? I’ve got high-level intros for you. Learn more here.What is your #1 Lead Generation BLOCKER? Take my free quiz here.Want to learn more about all the podcasts managed by UpMyInfluence? Opt in here.Don’t forget to subscribe to The Thoughtful Entrepreneur and thank you for listening. Tune in next time!

Building High-Performing WordPress Sites: Insights from Meeky Hwang, CEO of NdevrIn this episode of The Thoughtful Entrepreneur, host Josh Elledge speaks with Meeky Hwang, CEO and Co-Founder of Ndevr, a development firm specializing in high-performing WordPress solutions. Meeky shares how digital publishers can scale effectively, the "three-legged stool" framework for site success, and how to secure and optimize WordPress for high traffic and e-commerce.The Three-Legged Stool of WordPress SuccessMeeky emphasizes that a successful WordPress site rests on three foundational pillars: audience experience, editor experience, and developer experience. For site visitors, speed, mobile responsiveness, and accessibility are crucial. A seamless front-end experience keeps users engaged and ensures compliance with accessibility standards.From an editorial standpoint, she advises leveraging the Gutenberg block editor and custom workflows to streamline publishing. An intuitive backend not only enhances productivity but also reduces content errors and improves team morale. Editors need tools that fit their workflow, not ones they must work around.For developers, Meeky recommends maintaining a clean codebase, using version control systems like Git, and implementing continuous integration and deployment pipelines. This technical foundation supports performance, security, and scalability—especially critical for high-traffic sites. All three experiences must work in harmony for a WordPress site to perform at its best.About Meeky Hwang:Meeky Hwang is the CEO and Co-Founder of Ndevr, a WordPress development agency trusted by leading digital media and enterprise companies. With over 20 years of experience in web development and open-source technology, she specializes in optimizing complex digital ecosystems, strengthening DevOps, and aligning technology decisions with business goals. A passionate advocate for women in tech, Meeky is also a frequent contributor to Forbes, BuiltIn, and Thrive Global, where she shares leadership and digital strategy insights.About Ndevr:Ndevr is a WordPress development agency focused on high-traffic digital publishers and WooCommerce-driven e-commerce businesses. Their services include site audits, performance optimization, custom development, and strategic consulting.Links Mentioned in this Episode:Meeky Hwang on LinkedInNdevr Official WebsiteEpisode Highlights:The "three-legged stool" framework: audience, editor, and developer experience.Key WordPress best practices for high traffic and enterprise-grade publishing.How Ndevr grows through partnerships and referrals.WooCommerce security and performance strategies.Why regular audits and managed hosting are essential for WordPress success.ConclusionJosh and Meeky highlight the importance of strategic infrastructure and balanced user experiences in building successful WordPress sites. From scalability to security, Ndevr’s insights provide a blueprint for digital publishers and e-commerce leaders aiming to optimize performance. Whether you're a growing brand or a seasoned media company, implementing Meeky's advice will help future-proof your web presence.Apply to be a Guest on The Thoughtful Entrepreneur: https://go.upmyinfluence.com/podcast-guestMore from UpMyInfluence:We are actively booking guests for our The Thoughtful Entrepreneur. Schedule HERE.Are you a 6-figure consultant? I’ve got high-level intros for you. Learn more here.What is your #1 Lead Generation BLOCKER? Take my free quiz here.Want to learn more about all the podcasts managed by UpMyInfluence? Opt in here.Don’t forget to subscribe to The Thoughtful Entrepreneur and thank you for listening. Tune in next time!

Unlocking Influencer Marketing: A Conversation with Adam Rivietz of #PaidIn a recent episode of The Thoughtful Entrepreneur, host Josh Elledge speaks with Adam Rivietz, CSO and Co-Founder of #Paid, a platform revolutionizing influencer marketing by connecting brands with vetted creators. Adam shares how influencer marketing has evolved, the top challenges brands face, and how to approach creator partnerships more strategically.Navigating the Influencer Marketing LandscapeAdam opens the episode by reflecting on his personal journey, including how he overcame a fear of public speaking through stand-up comedy. This experience, he explains, mirrors the importance of authenticity—a key component in successful influencer marketing. Adam emphasizes that storytelling and genuine experiences resonate deeply, both on stage and in branded content.He goes on to describe the early skepticism brands had toward influencer marketing in 2014, and how platforms like #Paid have helped shift that perception. Today, brands recognize the value of creator-driven campaigns that feel native and personal. Adam discusses how declining organic reach, the rising cost of ads, and content fatigue are major challenges marketers face.#Paid addresses these issues by connecting brands with vetted creators who deliver authentic content and better engagement. The platform also enables creator licensing, allowing brands to run ads through influencers' accounts—boosting trust and conversion rates. Adam notes that enterprise brands and agencies, particularly those with mature digital strategies, benefit most from using #Paid.About Adam Rivietz:Adam Rivietz is the Chief Strategy Officer and Co-Founder of #Paid. He leads the company’s strategic direction and is passionate about helping brands scale through authentic creator partnerships.About #Paid:#Paid is a creator marketing platform designed to help enterprise brands and agencies manage influencer campaigns at scale. With a focus on authenticity, #Paid offers tools for creator discovery, campaign execution, and paid media integration.Links Mentioned in this Episode:Adam Rivietz on LinkedIn#Paid Official WebsiteEpisode Highlights:Adam's personal growth journey from public speaking fear to stand-up comedy.The evolution and current state of influencer marketing.How #Paid helps brands overcome content, reach, and advertising challenges.The role of authenticity and creator licensing in successful campaigns.Why enterprise brands and agencies benefit most from #Paid's offerings.ConclusionJosh and Adam highlight a clear truth: authentic, creator-led campaigns are the future of digital marketing. Platforms like #Paid empower brands and agencies to scale these efforts effectively. Whether you're new to influencer marketing or looking to optimize your strategy, building real relationships with creators is the key to driving meaningful results.Apply to be a Guest on The Thoughtful Entrepreneur: https://go.upmyinfluence.com/podcast-guestMore from UpMyInfluence:We are actively booking guests for our The Thoughtful Entrepreneur. Schedule HERE.Are you a 6-figure consultant? I’ve got high-level intros for you. Learn more here.What is your #1 Lead Generation BLOCKER? Take my free quiz here.Want to learn more about all the podcasts managed by UpMyInfluence? Opt in here.Don’t forget to subscribe to The Thoughtful Entrepreneur and thank you for listening. Tune in next time!

Why Modern B2B Sales Starts with Founders: Insights from Gabe Lullo of AlleyoopOn this episode of The Thoughtful Entrepreneur, host Josh Elledge speaks with Gabe Lullo, CEO of Alleyoop, a leading B2B sales development company. Gabe dives into the critical strategies that modern founders and sales teams need to adopt—covering everything from founder-led sales and shifting lead generation tactics to building authentic engagement through personal branding. This episode is a goldmine for startup founders, sales leaders, and anyone aiming to scale their outbound strategy with more precision and impact.Building a Modern B2B Sales EngineGabe emphasizes that founders must be on the front lines of sales early in their journey. Founders bring unmatched product knowledge and passion that resonates with early customers and helps shape go-to-market messaging. These firsthand sales experiences offer valuable insight into what prospects actually care about, allowing for real-time iteration and refinement. Gabe cautions against hiring a VP of Sales too early—founders need to establish a repeatable, scalable process before expanding the team.In today’s sales environment, traditional cold emailing is losing its edge due to regulation and deliverability challenges. Gabe recommends a return to high-impact basics: cold calling and content creation. Phone calls allow for real-time, human interaction, while content—especially on LinkedIn—builds trust and positions founders as thought leaders. Gabe practices what he preaches with his consistent posting strategy and his podcast, Do Hard Things, which highlights authentic stories of grit and resilience.Gabe also explains how Alleyoop helps B2B companies bridge the gap between marketing and sales. Their done-for-you systems manage appointment setting, lead qualification, and process optimization for clients ranging from startups to giants like Adobe and Zoom Info. For founders ready to scale their outreach, Gabe recommends focusing on authenticity, strategic connection building, and consistent engagement to generate high-quality pipeline.About Gabe LulloGabe Lullo is a seasoned entrepreneur and executive with deep expertise in sales, marketing, recruiting, and management. After graduating from the Barney School of Business at the University of Hartford, he launched his own sales, training, and marketing firm, which he successfully ran for over a decade. Gabe has also had a notable career in executive recruiting, expanding placements across IT, software development, sales, customer success, and executive leadership. As CEO of Alleyoop, he focuses on company culture, customer success, and scalable sales systems.About AlleyoopAlleyoop builds high-performing sales development systems for B2B clients. Their services include lead qualification, appointment setting, and outbound process design tailored for scalable growth.Links Mentioned in this EpisodeAlleyoop WebsiteGabe Lullo on LinkedInEpisode HighlightsFounders must lead sales to learn and iterate earlyCold calling and content outperform traditional cold emailLinkedIn content builds brand and trustAlleyoop connects marketing to sales with proven systemsAuthentic storytelling drives long-term engagementConclusionGabe Lullo delivers a compelling roadmap for building and scaling a sales engine rooted in authenticity, process, and founder-led momentum. His practical advice challenges conventional thinking and emphasizes the importance of doing the hard things that truly move the needle in B2B sales. For those looking to elevate their go-to-market strategy, this episode is a must-listen.Apply to be a Guest on The Thoughtful Entrepreneur: https://go.upmyinfluence.com/podcast-guestMore from UpMyInfluenceWe are actively booking guests for our The Thoughtful Entrepreneur. Schedule HERE.Are you a 6-figure consultant? I’ve got high-level intros for you. Learn more here.What is your #1 Lead Generation BLOCKER? Take my free quiz here.Want to learn more about all the podcasts managed by UpMyInfluence? Opt in here.Don’t forget to subscribe to The Thoughtful Entrepreneur and thank you for listening. Tune in next time!

Mastering Communication and Overcoming Anxiety: In-Depth Insights from Scott RameyEffective communication is the cornerstone of personal and professional success, yet for many, it’s a source of anxiety and self-doubt. In a recent episode of The Thoughtful Entrepreneur, host Josh Elledge sits down with Scott Ramey, Founder of The Scott Ramey Group, to explore the transformative power of authentic communication, the journey from anxiety to confidence, and actionable strategies for personal growth. Drawing from Scott’s decades of experience and his own struggles with speech anxiety, this episode offers a roadmap for anyone seeking to communicate with clarity, authenticity, and impact.Scott Ramey’s Journey: From Anxiety to AuthorityScott Ramey’s story is a powerful example of how communication skills can be developed over time, even for those who struggle with anxiety. Early in his career, Scott faced intense speech anxiety, but he transformed this weakness into a superpower, eventually becoming a communication coach. His story emphasizes that vulnerability is universal—successful leaders and communicators also face these challenges, but with the right mindset and tools, anyone can become a confident speaker.The core of Scott's teaching is that communication is about authenticity, not performance. He encourages people to embrace their true selves, moving away from the anxiety of pretending or trying to meet external expectations. As Scott notes, “You don’t have to say things that don’t resonate with your true feelings,” and embracing this authenticity can significantly improve confidence and communication.In addition to personal transformation, Scott emphasizes practical exercises, such as the Three-Column Method, to help individuals align their authentic self with their projected persona. By writing down the image they project, the vulnerabilities they hide, and the costs of these misalignments, individuals can gain clarity on their communication and begin to foster more genuine interactions.About Scott RameyScott Ramey is the Founder of The Scott Ramey Group, a coaching practice dedicated to helping individuals overcome communication anxiety, build confidence, and lead with authenticity. With over two decades of experience in personal growth and communication coaching, Scott empowers clients to navigate public speaking, leadership communication, and performance anxiety.About The Scott Ramey GroupThe Scott Ramey Group provides personalized coaching, workshops, and resources designed to help individuals master their communication skills. Specializing in overcoming anxiety, building confidence, and fostering authenticity in both personal and professional contexts, The Scott Ramey Group supports clients in improving their speaking, leadership, and interpersonal communication.Links Mentioned in This EpisodeThe Scott Ramey Group WebsiteScott Ramey on LinkedInKey Episode HighlightsVulnerability is Universal: Even successful communicators experience anxiety—growth is possible with the right tools.Authenticity vs. Performance: How embracing your true self can reduce anxiety and lead to more meaningful communication.Practical Tools for Change: Using the Three-Column Method to align your authentic self with how you present yourself to the world.Overcoming the Spotlight Effect: Shifting your focus from judgment to adding value and connecting with others.Mindset Shifts: Transitioning from scarcity to abundance in communication and leadership.ConclusionScott Ramey’s journey from anxiety to authenticity provides a powerful reminder that effective communication is a skill that can be developed. By embracing vulnerability, adopting a mindset of abundance, and using actionable strategies like the Three-Column Method, anyone can overcome performance anxiety and communicate with confidence. Whether you’re speaking to a large audience or having one-on-one conversations, authenticity and clarity are your keys to success.*Apply to be a Guest on The Thoughtful Entrepreneur: https://go.upmyinfluence.com/podcast-guestMore from UpMyInfluence:We are actively booking guests for our The Thoughtful Entrepreneur. Schedule HERE.Are you a 6-figure consultant? I’ve got high-level intros for you. Learn more here.What is your #1 Lead Generation BLOCKER? Take my free quiz here.Want to learn more about all the podcasts managed by UpMyInfluence? Opt in here.Don’t forget to subscribe to The Thoughtful Entrepreneur and thank you for listening. Tune in next time!