The Thoughtful Entrepreneur

Navigating Payroll and HR in the Cannabis Industry: Insights from Marc Rodriguez of Green Leaf Payroll & Business Solutions Inc.The cannabis and hemp industries are growing rapidly but face some of the most complex compliance and regulatory challenges in business today. In this episode, host Josh Elledge speaks with Marc Rodriguez, Co-founder and CEO of Green Leaf Payroll & Business Solutions Inc., about how cannabis companies can overcome payroll, HR, and benefits hurdles. Marc shares how his firm helps businesses navigate industry-specific issues like federal restrictions, Section 280E taxation, and labor peace agreements—offering a roadmap for building compliant, scalable operations.Building Compliance and Resilience in a Complex IndustryMarc explains that cannabis companies operate in an environment where traditional payroll providers often refuse service, leaving them vulnerable. Green Leaf was founded to fill that gap—helping businesses stay compliant while managing payroll, HR, and benefits seamlessly across vertically integrated operations. The company’s experience in taxation, union reporting, and state-specific labor requirements allows clients to focus on growth rather than administrative chaos.Beyond compliance, Marc draws parallels between his personal CrossFit discipline and business health, stressing that consistent “maintenance” is key. Just as injury prevention requires intentional effort, so does building a company that can weather regulatory shifts and operational challenges. Green Leaf’s approach blends proactive compliance with strategic consulting, ensuring clients have both protection and flexibility.He also emphasizes technology and leadership involvement in decision-making. From implementing user-friendly HR platforms to developing transparent 401(k) options for cannabis employees, Green Leaf helps clients elevate both operations and culture. Marc encourages CEOs to view HR and payroll as strategic assets, not afterthoughts, and to surround themselves with specialized partners who understand their industry’s nuances.About Marc RodriguezMarc Rodriguez is the Co-founder and CEO of Green Leaf Payroll & Business Solutions Inc., specializing in payroll, HR, benefits, and recruiting solutions for the cannabis and hemp industries. A recognized leader in regulated markets, Marc is passionate about helping business owners build compliant, efficient, and sustainable organizations through expertise and transparency.About Green Leaf Payroll & Business Solutions Inc.Green Leaf Payroll & Business Solutions Inc. provides comprehensive HR, payroll, and benefits services tailored specifically for cannabis and hemp businesses. The company partners with clients across cultivation, manufacturing, and retail to streamline operations, ensure compliance, and manage growth effectively. Learn more at greenleafbizsolutions.com.Links Mentioned in This EpisodeMarc Rodriguez on LinkedInGreen Leaf Payroll & Business Solutions Inc.Key Episode HighlightsCannabis businesses face unique payroll, tax, and compliance challenges.Green Leaf specializes in Section 280E compliance and labor peace agreements.Proactive HR “maintenance” is vital to long-term business health.Technology and leadership alignment drive stronger employee experiences.Expert partnerships are essential in high-regulation industries.ConclusionOperating a cannabis business requires more than great products—it demands expertise in compliance, payroll, and people management. Marc Rodriguez’s insights reveal how specialized support and proactive systems can protect your business while enabling sustainable growth. By partnering with experienced professionals like Green Leaf, leaders can focus on what they do best: building thriving, legitimate companies in one of the fastest-growing industries in North America.🎧 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!

How AI and No-Code Tools Are Transforming Business: Insights from Sean Weisbrot of We Live to BuildTechnology is evolving faster than ever, and businesses that don’t adapt risk falling behind. In this episode, host Josh Elledge interviews Sean Weisbrot, Founder and CEO of We Live to Build, to explore how artificial intelligence and no-code tools are revolutionizing business operations and software development. Sean, who has interviewed more than 260 founders and investors, shares powerful insights on how these tools are reshaping entrepreneurship, empowering non-technical founders, and creating scalable opportunities for growth.Building Smarter, Faster, and More Accessible BusinessesSean explains that AI is not just improving efficiency—it’s transforming how companies think and operate. From automating manual processes to enabling rapid data-driven decision-making, AI is now a core component of modern business strategy. Sean also discusses the mindset shift among founders who are embracing automation and using AI as a strategic partner, not just a productivity tool.He introduces the concept of “vibe coding,” where AI is used to build and iterate software faster than ever before. Through tools like Cursor, Lovable, and Bubble, founders can now develop full-fledged applications in days, eliminating traditional barriers to innovation. These no-code and low-code platforms are democratizing access to technology, allowing visionaries without deep technical backgrounds to test ideas and build products with speed and confidence.Sean emphasizes that while AI agents and automation offer incredible potential, success depends on customization, trusted implementation, and ethical use. He warns against one-size-fits-all solutions and stresses the importance of choosing partners who understand your business goals. His message to founders is clear—stay curious, experiment boldly, and use technology to create meaningful, scalable impact.About Sean WeisbrotSean Weisbrot is the Founder and CEO of We Live to Build, a media and consulting platform focused on empowering entrepreneurs through AI, automation, and community. As a serial entrepreneur and host of the We Live to Build podcast, Sean has interviewed hundreds of founders, executives, and innovators, distilling their lessons into actionable insights for business leaders worldwide.About We Live to BuildWe Live to Build is an entrepreneurial education platform and podcast that helps founders grow, automate, and scale their businesses using modern technology. The brand offers interviews, tutorials, and consulting focused on AI, no-code development, and business systems that drive sustainable growth. Learn more at welivetobuild.com.Links Mentioned in This EpisodeSean Weisbrot on LinkedInWe Live to Build WebsiteKey Episode HighlightsAI is transforming both business operations and founder mindsets.“Vibe coding” enables faster, more accessible software development through AI.No-code and low-code tools empower non-technical founders to build MVPs quickly.Automation works best when customized and ethically implemented.Podcasting remains a powerful tool for networking and business growth.ConclusionAI and no-code platforms are opening new doors for innovation, scalability, and entrepreneurship. As Sean Weisbrot explains, success in this new era comes from pairing curiosity with strategy—using tools wisely, staying adaptable, and fostering meaningful relationships along the way. Founders who embrace these changes will be best positioned to lead in the digital-first economy.🎧 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!

How to Scale and Exit Your Business the Right Way: In-Depth Insights from Josh DavisMany founders and CEOs find themselves caught in the day-to-day grind, unsure how to grow their business sustainably—or how to prepare for an eventual exit. In this episode, host Josh Elledge interviews Josh Davis, five-time founder, Chairman and CEO of JL Davis Enterprises, and one of Canada’s Top 40 Under 40. Drawing from his own entrepreneurial journey and experience selling a fast-growing logistics company, Josh shares a step-by-step guide for scaling, systemizing, and ultimately creating a business that can thrive independently of its founder.Building for Scalability and Exit SuccessJosh emphasizes that every entrepreneur should build their business as if they plan to sell it, even if they never do. A “sale-ready” company—one with clear processes, reliable systems, and strong leadership—is not only more valuable to buyers but also far easier to manage. Founders who invest early in documentation, automation, and leadership development create companies that can grow sustainably and operate smoothly without their constant involvement.A critical part of scaling is having the right people in the right roles. Josh explains that businesses often plateau because of leadership gaps or founder dependency. He recommends regularly auditing your organizational structure, empowering key hires, and fostering a culture of ownership across all levels. By delegating effectively, founders free themselves to focus on strategy rather than daily operations.When it comes to exits, planning years in advance is key. The best outcomes happen when founders clean up financials early, minimize founder reliance, and work with experienced advisors well before they’re ready to sell. Josh’s firm helps business owners navigate this process, whether they’re preparing for acquisition, seeking investors, or simply aiming for a more autonomous company.About Josh DavisJosh Davis is a five-time founder and the Chairman & CEO of JL Davis Enterprises, where he helps entrepreneurs scale and position their businesses for successful exits. Recognized as one of Canada’s Top 40 Under 40, Josh has led multiple ventures in logistics, consulting, and investment, combining hands-on leadership with a passion for mentorship and sustainable business growth.About JL Davis EnterprisesJL Davis Enterprises partners with founders and CEOs to optimize growth, streamline operations, and prepare businesses for sale or succession. The firm offers consulting, advisory, and acquisition services designed to help companies become more scalable, profitable, and self-sufficient. Learn more and access free resources at jldavisenterprises.com.Links Mentioned in This EpisodeJosh Davis on LinkedInJL Davis Enterprises WebsiteKey Episode HighlightsBuild your business as if you plan to sell it—whether you do or not.Hire and empower leaders who can run the business without constant founder input.Document and automate processes to enable scalability and efficiency.Prepare for a strategic exit years in advance, not months before selling.Invest in mentorship and expert advisors to avoid costly mistakes early on.ConclusionScaling and exiting a business successfully requires vision, structure, and discipline. As Josh Davis explains, true freedom for founders comes from building companies that can run and grow independently. By focusing on scalable systems, strong leadership, and early exit planning, entrepreneurs can create businesses that thrive—with or without them.🎧 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!

Unlocking E-Commerce Success: Expert Insights on Shopify, AI, and B2B with Mac King of DomaineIn today’s fast-changing digital landscape, success in e-commerce requires more than great products—it demands innovation, strategy, and adaptability. In this episode, host Josh Elledge interviews Mac King, Co-Founder and Chief Revenue Officer of Domaine, a leading Shopify agency, to explore the latest trends transforming online retail. From the power of AI-driven shopping and B2B growth on Shopify to the revival of branded mobile apps, Mac shares proven strategies for brands aiming to elevate their digital presence and thrive in 2025 and beyond.How AI and Shopify Are Reshaping the Future of E-CommerceMac King emphasizes that artificial intelligence is revolutionizing how consumers discover, compare, and purchase products. AI-powered assistants like ChatGPT are becoming personal shopping guides, meaning brands must optimize their Shopify stores for visibility in these new AI-driven discovery channels. Structured data, schema markup, and detailed product descriptions are no longer optional—they’re essential for ensuring your brand appears in AI-generated recommendations.Beyond search, AI also enables personalization that rivals the in-store experience. With tools that track preferences, sizes, and purchase histories, online retailers can now deliver tailored recommendations, dynamic content, and real-time support. Mac advises brands to think like a trusted in-store associate: anticipate customer needs, use data wisely, and make every online interaction feel personal.He also highlights Shopify’s growing role in the B2B space. With new features such as wholesale portals, custom pricing, and ERP integrations, Shopify empowers businesses to serve both direct consumers and trade buyers from a single platform. Combined with the resurgence of branded mobile apps—offering direct engagement through push notifications and loyalty rewards—these innovations position brands for long-term growth and customer retention.About Mac KingMac King is the Co-Founder and Chief Revenue Officer (CRO) of Domaine, where he leads revenue strategy and client partnerships. With years of experience in digital commerce and Shopify development, Mac helps brands integrate technology, storytelling, and customer experience to drive measurable growth. His expertise spans DTC, B2B, and omnichannel strategy.About DomaineDomaine is a top-rated Shopify Plus agency specializing in strategy, design, and custom development for growing e-commerce brands. The company partners with clients across industries to optimize digital storefronts, streamline backend systems, and create seamless, revenue-driving customer experiences. Learn more at meetdomaine.com.Links Mentioned in This EpisodeMac King on LinkedInDomaine WebsiteKey Episode HighlightsAI is transforming how consumers shop, acting as a personalized discovery engine.Shopify’s built-in B2B tools create new revenue opportunities for growing brands.Personalization through AI can replicate the “in-store” experience online.Branded mobile apps are regaining popularity for loyalty and direct engagement.Optimizing your store for AI visibility is essential for long-term competitiveness.ConclusionThe future of e-commerce is intelligent, integrated, and deeply personal. As Mac King explains, embracing AI, optimizing for new discovery channels, and leveraging Shopify’s evolving features will be key to thriving in the next wave of digital commerce. Whether you’re a DTC brand or expanding into B2B, success lies in combining innovation with authentic customer connection.🎧 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 Personal Branding in the Age of AI: Insights from Lauren DavisIn a world increasingly shaped by digital visibility and AI-driven search, personal branding has become a necessity—not a luxury. In this episode, host Josh Elledge interviews Lauren Davis, Founder of Lauren Davis Creative, who shares her five-step framework for building an authentic, memorable, and future-proof personal brand. From storytelling and search visibility to nurturing community and staying adaptable, Lauren offers actionable advice for professionals and entrepreneurs who want to stand out and connect meaningfully in 2024 and beyond.Building a Personal Brand That Grows with YouLauren Davis’s approach to personal branding is rooted in intentionality and authenticity. Drawing on her experience as a record store owner turned branding consultant, she emphasizes that branding isn’t about perfection—it’s about connection. Every interaction online contributes to your personal narrative, and managing that narrative proactively ensures your audience sees the real you.Her five-step process begins with being findable online—optimizing search results, claiming your digital space, and differentiating your name or identity. Next, she highlights curating your brand experience: ensuring your website, visuals, and messaging reflect who you are today. From there, it’s about nurturing relationships through value-driven content, genuine engagement, and consistent communication. Lauren also underscores the power of storytelling, urging professionals to build community through shared experiences. Finally, she recommends auditing your brand regularly to stay relevant as trends, technology, and your personal goals evolve.Lauren points out that AI is reshaping how personal brands are discovered, with search engines and chatbots pulling from public content to form impressions. To stay ahead, professionals must be proactive—keeping profiles current, managing reputation across platforms, and using keywords and narratives that align with how they want to be found. The key takeaway? A personal brand isn’t built overnight; it’s cultivated through clarity, consistency, and connection over time.About Lauren DavisLauren Davis is a personal branding strategist, speaker, and Founder of Lauren Davis Creative, where she helps entrepreneurs and professionals build impactful, human-centered brands. Known for her practical frameworks and genuine approach, Lauren has guided thousands of clients in defining their identity, refining their messaging, and increasing visibility through storytelling, strategy, and community building. She is also the host of The Real Personal Branding Podcast.About Lauren Davis CreativeLauren Davis Creative is a brand development and personal growth consultancy helping professionals and business owners establish and evolve their digital presence. The firm’s mission is to empower clients to take control of their narrative through personalized brand strategy, visibility coaching, and creative storytelling that authentically connects with audiences.Links Mentioned in This EpisodeLauren Davis on LinkedInLauren Davis Creative WebsiteKey Episode HighlightsPersonal branding is about connection and clarity, not perfection.Being findable online is the foundation of a strong digital presence.Storytelling and community foster deeper audience relationships.Regular brand audits keep your message current and aligned.AI is transforming discoverability—manage your online footprint proactively.ConclusionLauren Davis’s insights remind us that a personal brand is an evolving relationship between who you are and how you’re perceived. By staying intentional, embracing authenticity, and leveraging both human and AI tools, you can craft a personal brand that grows alongside you—driving both trust and opportunity.🎧 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 LinkedIn in 2024: Expert Strategies from MAIA DigitalLinkedIn has become more than just a job-hunting platform—it’s now the go-to space for business growth, personal branding, and professional influence. In this episode, host Josh Elledge interviews Shay Thieberg and Eli Igra Serfaty, co-founders of MAIA Digital, to discuss how individuals and companies can maximize their visibility and results on LinkedIn. They explore the platform’s latest features, user behavior trends, and actionable strategies that turn casual networking into meaningful business opportunities.The Future of LinkedIn: Engagement, Authenticity, and OpportunityAccording to Shay and Eli, LinkedIn has evolved into a powerful ecosystem for professionals, executives, and business owners who want to establish thought leadership. Unlike other social platforms, most LinkedIn users are senior decision-makers—and yet only 1% create content. This creates a huge opportunity for consistent, authentic voices to stand out and build authority.The duo emphasizes that engagement is the new currency on LinkedIn. Thoughtful comments and conversations often generate more visibility than standalone posts, as they demonstrate credibility and spark genuine interaction. They also discuss LinkedIn Sales Navigator as a high-ROI tool when used to build relationships instead of sending mass messages. In addition, features like LinkedIn newsletters and optimized company pages are underused assets that can rapidly expand reach, SEO visibility, and brand trust.Ultimately, Shay and Eli highlight that success on LinkedIn requires consistency, community, and clarity of purpose. Whether you’re growing a business, nurturing partnerships, or positioning yourself as an industry expert, being authentic, data-informed, and strategically visible are the keys to long-term impact on the platform.About MAIA DigitalMAIA Digital is a LinkedIn-first marketing and branding agency founded by Shay Thieberg and Eli Igra Serfaty. The agency specializes in helping founders, executives, and companies amplify their presence through optimized content strategies, profile makeovers, and engagement-driven growth campaigns. MAIA Digital’s mission is to help professionals move from passive users to active influencers who attract business organically.About Shay Thieberg & Eli Igra SerfatyShay Thieberg and Eli Igra Serfaty are LinkedIn growth experts and co-founders of MAIA Digital. With backgrounds in marketing, communications, and business development, they help clients convert online visibility into real-world opportunity. Together, they’ve developed frameworks that merge analytics, psychology, and storytelling to help professionals grow faster and more authentically on LinkedIn.Links Mentioned in This EpisodeShay Thieberg on LinkedInEli Igra Serfaty on LinkedInMAIA Digital WebsiteKey Episode HighlightsLinkedIn has evolved into a professional ecosystem for branding, sales, and thought leadership.Only 1% of users post content, meaning consistent engagement can create outsized visibility.Commenting and genuine interaction often outperform standalone posts.LinkedIn newsletters and company pages are underutilized tools for authority and SEO growth.Authenticity, engagement, and clear positioning drive long-term success on LinkedIn.ConclusionThe insights shared by Shay and Eli make one thing clear: LinkedIn in 2024 rewards those who show up consistently, share authentically, and engage with purpose. Whether you’re a founder, marketer, or executive, embracing LinkedIn’s evolving tools can transform your professional presence and unlock real business growth.🎧 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!

How to Build a High-Performing Sales Team in a Founder-Led Business: Insights from Nicholas LoiseFor many small and midsize business owners, sales can be both the engine and the bottleneck of growth. Founder-led sales will only take a company so far before scalability demands process, structure, and leadership. In this episode, host Josh Elledge speaks with Nicholas Loise, Founder of Sales Performance Team, who shares practical strategies for transitioning from founder-driven selling to building a high-performing, self-sustaining sales organization.Building a Scalable Sales SystemNicholas Loise explains that most founders struggle with hiring salespeople because they underestimate how different it is to sell for a small business compared to a large enterprise. Without the backing of a big brand, sales success depends on grit, creativity, and adaptability. He emphasizes that before hiring, founders must document their entire sales process—from prospecting and discovery to objection handling and closing—so new hires have a clear roadmap to follow.Once the playbook is in place, Nicholas recommends hiring two salespeople at once to increase the chances of success, benchmark performance, and encourage healthy collaboration. He also stresses the importance of investing heavily in the first 90 days, creating structured onboarding, shadowing opportunities, and clear milestones to ensure quick ramp-up and retention. Compensation should be simple and transparent, typically a mix of base salary plus commission that motivates results while providing stability during onboarding.Finally, Nicholas discusses how to maintain oversight without micromanaging. Delegating sales effectively requires trust—but also process. Regular reviews, feedback loops, and continuous updates to your playbook keep the system strong. By using objective assessment tools and focusing on cultural fit, founders can build sales teams that scale sustainably and deliver consistent performance long after they’ve stepped out of the front-line role.About Nicholas LoiseNicholas Loise is the Founder of Sales Performance Team and a seasoned sales strategist who helps founder-led businesses build scalable, high-performing sales teams. With decades of experience in sales leadership, Nicholas specializes in designing sales playbooks, recruiting and onboarding top-performing reps, and aligning compensation structures that drive profitable growth.About Sales Performance TeamSales Performance Team helps $1M–$25M companies transition from founder-led selling to a system-driven sales organization. The firm provides fractional sales leadership, sales team recruitment, onboarding systems, compensation design, and proven frameworks that help founders replace intuition with strategy—and build a sales team that consistently delivers results.Links Mentioned in This EpisodeSales Performance Team WebsiteNicholas Loise LinkedIn ProfileKey Episode HighlightsFounders often struggle to hire sales reps because they underestimate how different small-business selling is from enterprise sales.Documenting your entire sales process—from prospecting to closing—is essential before stepping out of the role.Hiring two salespeople at once improves benchmarking, morale, and retention while reducing hiring risk.Strong onboarding within the first 90 days directly impacts sales performance and long-term success.Keep compensation plans simple, transparent, and performance-driven to attract and retain top talent.ConclusionBuilding a sales team is not a one-time event—it’s a process of structure, training, and continuous improvement. Nicholas’s insights provide a roadmap for founders who want to free themselves from day-to-day selling while maintaining performance and culture. With a documented playbook, strategic hiring, and strong onboarding, any growing business can turn sales from a bottleneck into a scalable growth engine.🎧 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 Digital Transformation in Construction: Expert Insights from Huw Roberts, CEO of PMWEBThe construction industry is evolving at a critical pace—balancing traditional processes with the rise of AI, automation, and digital transformation. In this episode of The Thoughtful Entrepreneur, host Josh Elledge sits down with Huw Roberts, CEO of PMWEB, to discuss how construction firms can modernize operations, improve efficiency, and adopt outcome-driven technology strategies. Huw shares actionable insights for leaders navigating uncertainty, highlighting the need for clear goals, practical innovation, and consistent learning to build resilient, future-ready organizations.The Digital Shift in ConstructionThe construction industry is one of the largest in the world but also among the slowest to digitize. Huw Roberts explains that while many sectors have embraced automation and AI, much of construction still depends on manual workflows, spreadsheets, and outdated systems. This creates inefficiencies that technology can help solve—if applied with purpose.Huw stresses that digital transformation isn’t about adopting the latest tool; it’s about aligning technology with specific outcomes. Whether the goal is faster project delivery, better collaboration, or improved forecasting, success starts with defining measurable results and working backward from there. Companies should begin with small pilot projects, gather feedback, and scale successful initiatives across the organization.Ultimately, balancing innovation with caution is essential. Large enterprises can absorb the risks of experimentation, while small and mid-sized businesses must focus on clear returns. By adopting an outcome-focused mindset and continuously learning from both wins and failures, construction firms can achieve meaningful transformation without sacrificing stability.About Huw RobertsHuw Roberts is the CEO of PMWEB, where he leads a global team dedicated to transforming how organizations plan, manage, and deliver construction and real estate projects. With a background in architecture and decades of experience in technology leadership, Huw bridges design, innovation, and business strategy to help clients improve performance and embrace the digital future of project management.About PMWEBPMWEB is a leading enterprise software platform that streamlines construction and real estate portfolio management. Designed for performance and transparency, PMWEB equips organizations with the tools to manage costs, schedules, and outcomes through data-driven decision-making. The company’s integrated approach enables project teams to operate more efficiently and deliver measurable business results.Links Mentioned in This EpisodeHuw Roberts LinkedInPMWEB WebsiteKey Episode HighlightsThe construction industry remains one of the least digitized but most opportunity-rich sectors.AI and automation are transforming project management efficiency.Outcome-focused decision-making ensures measurable and sustainable innovation.Pilot programs help companies minimize risk while adopting new technology.PMWEB empowers organizations to modernize processes and maximize ROI.ConclusionHuw Roberts’ insights reveal that digital transformation in construction isn’t just about technology—it’s about clarity, adaptability, and purpose. By focusing on measurable outcomes, leveraging AI strategically, and empowering teams with the right tools, leaders can drive lasting efficiency and resilience. The companies that connect technology with vision will define the next generation of construction excellence.🎧 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!

Building a High-Performance Workplace Culture: Insights from Matthew Person’s “Four I’s” MethodologyIn this episode of The Thoughtful Entrepreneur, host Josh Elledge speaks with Matthew Person, business strategist, M&A advisor, and Founder & Managing Director of Town Square Business Advisors. Matthew shares his framework for building a high-performance workplace culture—one that blends structure with freedom and aligns values with execution. His “Four I’s” methodology—Identity, Instruction, Intercommunication, and Information Feedback—helps companies create environments where clarity, collaboration, and accountability thrive.Rethinking Culture: The Four I’s FrameworkMatthew Person explains that too many companies try to copy “Best Places to Work” models without understanding what makes their own teams unique. He emphasizes that culture is not about perks or imitation—it’s about clarity of purpose and alignment with organizational identity. The first pillar, Identity, defines who you are as a company and why you exist, serving as a foundation for decisions, relationships, and results.The next two pillars, Instruction and Intercommunication, address how organizations operate and communicate. Instruction provides structure—ensuring that processes, roles, and expectations are clear—while intercommunication builds trust by encouraging open, consistent dialogue. When both elements are strong, teams move cohesively, information flows effectively, and leaders can focus on strategy rather than micromanagement.Finally, Information Feedback turns culture into a living, adaptive system. Feedback, Matthew explains, should be consistent, transparent, and actionable—not reserved for annual reviews. Together, the Four I’s create what he calls constrained independence—a balance between freedom and boundaries that empowers innovation without chaos. The result is a culture that performs with purpose, resilience, and shared accountability.About Matthew PersonMatthew Person is the Founder and Managing Director of Town Square Business Advisors, where he works with executives and business owners to enhance strategy, leadership, and organizational culture. With decades of experience in mergers, acquisitions, and business growth advisory, Matthew developed the Four I’s framework to help leaders build clarity, cohesion, and confidence into every level of their company.About Town Square Business AdvisorsTown Square Business Advisors partners with business leaders and organizations to create sustainable growth through strategic clarity, operational excellence, and people-centered culture. The firm specializes in M&A advisory and executive consulting, helping companies align their leadership, systems, and communication for long-term success.Links Mentioned in This EpisodeMatthew Person on LinkedIn: https://www.linkedin.com/in/matthewdperson/Town Square Business Advisors: www.townsquare-advisors.comKey Episode HighlightsGreat culture isn’t copied—it’s created from your company’s authentic identity.The Four I’s—Identity, Instruction, Intercommunication, and Information Feedback—form a foundation for success.“Constrained independence” gives employees freedom within clear boundaries.Consistent, transparent feedback fosters trust and continuous improvement.Alignment between stated values and real behavior sustains long-term performance.ConclusionMatthew Person’s Four I’s methodology helps leaders move beyond surface-level culture initiatives and build organizations where clarity, communication, and trust drive measurable results. By grounding culture in identity and reinforcing it through structured communication and feedback, businesses can empower their teams and scale with purpose.🎧 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!

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.