21st Century Entrepreneurship

Brook Shepard is the Founder, CEO, of Mason Interactive and a seasoned performance marketing expert with 16 years of industry experience, leading a firm that manages billions in client assets. We spoke about the evolution of digital advertising, the rising dominance of creative strategy, and how AI is reshaping media buying without replacing human ingenuity.Brook shares key insights from his journey—starting in the early days of search advertising when gaming platforms was the norm, to today’s landscape where Meta and Google dominate. He reveals how creative has transformed from a secondary consideration to a primary driver of success:"Creative actually wasn’t as important in a client’s campaigns 10 years ago or even 5 years ago before iOS 14… But now, creative is more important than ever and needs to be informed by data."We explore how AI enhances, rather than replaces, creative work. By analyzing thousands of ad variations across years of data, Brook’s team uncovers the patterns behind high-performing campaigns:"AI helps us analyze data over vast data sets. It does not replace the human intent of the idea and the story that we're telling."Through real-world examples, Brook breaks down how businesses can optimize their ad spend. Whether it’s a coffee brand achieving a 4x increase in click-through rates through systematic testing, or a jewelry company using organic content to fuel paid campaigns, the lesson is clear—data, design, and strategy must work together."If you don’t know why an ad was successful, you can’t double down on it. And if you can’t double down, you can’t scale."Brook also shares personal reflections on leadership, growth, and the importance of continuous learning:"Each day, I ask: What haven’t I done today that I want to do better tomorrow? How can I put more weight on my marketing bar?"Key Takeaways:AI is a tool, not a replacement – It accelerates analysis but doesn’t replace creative storytelling.Creative strategy now defines success – The right visual, message, and call-to-action can multiply ad performance.Testing is everything – Isolating variables and refining continuously can drive massive results.The right agency is like a well-engineered machine – Big enough to deliver global impact, small enough to keep leadership hands-on.Whether you're an entrepreneur, marketer, or business leader, this conversation will give you a fresh perspective on data-driven creativity and the future of advertising.

Avigail Berg is the Owner, Manufacturer, Wellness Expert, Visionary & Futuristic Entrepreneur behind TheSoundWell Vibro-therapy. We spoke about how harmonic low sound frequencies are being used to alleviate pain, stress, insomnia, and anxiety, helping people achieve better mental and physical well-being.Avigail shared the origins of her journey, starting with her master's thesis in holistic health, which led her to connect with Norwegian vibroacoustic therapy pioneer Olav Skil. She described how Skil’s discovery—that low sound frequencies positively impacted disabled children—sparked her dedication to developing ergonomic equipment like mats, recliners, pillows, and even sonic pets."The human body is just like an instrument," Avigail explained. "You can attune different parts of the body just like you're tuning a bass." She detailed how these frequencies penetrate deep tissue to help manage chronic conditions like Parkinson's, fibromyalgia, and MS—not as cures but as tools for symptom relief and enhanced life quality.We explored the 'four siblings from hell'—pain, stress, insomnia, and anxiety—that drain our energy and reduce our performance, communication, and creativity. Vibroacoustic therapy, Avigail said, helps "reset, reboot, and recharge" the mind and body, creating mental clarity by minimizing what she calls the "spaghetti mind"—the tangled web of thoughts, emotions, and memories.Avigail also discussed her innovative projects like the Softwave Café, which introduces conscious entertainment spaces with multisensory relaxation experiences, and the development of Sonic Pets. "When you hug it," she said, "you feel hugged from within." She's now seeking partners to integrate positive psychology AI into these pets to support children with special needs and people with dementia.Key Takeaways:Low sound frequencies can help reduce chronic pain, stress, insomnia, and anxiety.The mind and body respond to harmonic vibrations, creating mental clarity and relaxation without guided imagery.Vibroacoustic therapy supports cognitive, emotional, and physical well-being across age groups.Innovative applications like Softwave Café and Sonic Pets show the evolving potential of sound therapy in daily life.Tune in to discover how sound frequencies might help you or your clients find calm, clarity, and creativity in a noisy world.

Diane Strand is an Executive Producer - Spirit of Innovation, CEO of JDS Studios, Nonprofit Founder & Executive Director, Serial Entrepreneur, TEDx Speaker, and Bestselling Author #JDSFamily. We spoke about the journey of entrepreneurship, the power of saying “yes” to opportunities, and how creativity can be the foundation for business success.Diane has built multiple businesses, including a nonprofit that grew into a seven-figure enterprise. She shares how she launched over 100 creative careers, helped entrepreneurs build authority, and leveraged storytelling for impactful marketing. With a career that started in Hollywood, working on shows like Friends and General Hospital, Diane transitioned into creating opportunities for aspiring creatives and business owners alike.One of Diane’s core messages is to “start before you’re ready”—a mindset shift that separates those who take action from those who let fear hold them back. “Don’t find the excuses because that’s fear talking,” she says. “It will always try to make you safe… Get started now. Get involved with your community.”She explains how providing value before asking for anything in return has been a game-changer in her journey. “Everything doesn’t have to be a hard sell. Sometimes you just need to provide the value so other people want to be a part of the magic that you’re creating.”Diane also discusses:The power of showing up and saying yes – How a simple networking event led her to launch a groundbreaking career program for adults with developmental disabilities.Building a personal and business brand – Why blending technical and soft skills is key to standing out.How to gain credibility in male-dominated industries – Her story of producing a Barbra Streisand concert and the lesson she learned about speaking up.Turning tiny wins into big momentum – “Celebrate being able to pick up the phone, make that one call, show up in a room where you don’t know anyone. Those are tiny wins that create momentum.”This episode is for anyone looking to step into entrepreneurship with confidence, scale their business through strategic branding, and turn creative passion into a profitable, purpose-driven career.

Cory O'Daniel is the CEO and co-founder of Massdriver and a co-founder of OpenTofu. We spoke about the growing skills crisis in cloud operations, the limitations of AI in solving it, and how companies can bridge the gap between software development and infrastructure management.Cory warns of an impending "existential crisis" in cloud expertise: "There is not a ton of people that understand how to use the cloud… and a lot of people are banking on AI solving it." But the problem, he explains, is that AI isn’t trained on the real, private complexities of cloud operations—it only learns from public code snapshots. This means that businesses are moving more of their infrastructure to the cloud with fewer people who actually know how to secure, optimize, and manage it.The discussion highlights a stark reality: while the number of software developers is projected to increase from 27 million to 45 million by 2030, "the amount of people that have experience in cloud operations… decreases every year." Cory points out that cloud management isn't something you learn in a coding boot camp, yet it's essential for running modern businesses securely and efficiently.We also explored the resurgence of Platform as a Service (PaaS) solutions and why developers are shifting toward tools that "dumb it down" and remove the complexity of cloud operations. But for enterprises too large or complex to rely on PaaS, companies need better collaboration between developers and operations teams—without forcing developers to become cloud experts.Key takeaways:The Cloud Skills Crisis is Real: While software development is booming, expertise in running cloud infrastructure is vanishing.AI Won’t Save Us: "AI is not going to help us here… It might make somebody who knows what they're doing more efficient, but it's not going to make somebody who doesn’t know what they're doing know what they're doing."PaaS is Making a Comeback: More developers are choosing abstraction layers over direct cloud management, but this isn’t a solution for every business.Collaboration is Key: Cory emphasizes that "DevOps was never really about one person doing another person's job—it was about teams working together better."Cory’s perspective challenges the conventional wisdom around AI and automation, making this conversation a must-listen for anyone navigating the future of cloud infrastructure.

Jeff Sauer is a data-driven marketing expert, co-founder of MeasureU.com and ProfitSchool, and an educator who has helped thousands of professionals master digital measurement and optimization. We spoke about the power of tracking and analyzing marketing efforts, how to turn insights into action, and why problem-solving is the ultimate key to business success.Jeff started as a website developer in the mid-2000s, quickly realizing that just building a website wasn’t enough—clients wanted proof it was working. “I had no idea if it was good or not,” he admits. “I was basically focused on the result only… and really whether the result was there or not, I had no accountability.” That realization led him to a major shift: understanding that the real value wasn’t just in creating something, but in knowing whether it was performing effectively.In this conversation, Jeff breaks down the essential role of measurement in business growth, explaining how companies waste massive budgets on ineffective strategies simply because they lack visibility into what’s working. “For that million dollars, you’re getting 20 leads. Do you think that’s a good use of your money?” he asked a major corporation, illustrating the stark reality many businesses face.We explored:How Jeff transitioned from web development to marketing analytics by recognizing the need for measurable impact.The key mindset shift: “People are often willing to pay you a lot more to figure out how to make your website work.”How even a small local business can apply the same optimization principles as a billion-dollar corporation.The biggest mistakes businesses make in digital marketing and how to fix them.Why AI will enhance—not replace—marketing professionals who know how to leverage data.Key Takeaways:✅ Measurement is your edge: If you’re not tracking results, you’re guessing—and guessing is expensive.✅ Optimization is an ongoing process: "It’s almost always a stream of low-hanging fruit. You can be very well fed just by continuing to find the obvious answers."✅ AI won’t replace problem solvers—only those who don’t evolve: "You will be replaced if you can't leverage it."✅ Success starts with solving problems: "Figure out that problem, figure out how you can uniquely solve it, and then go do it."Jeff’s journey is proof that measurement isn’t just about numbers—it’s about unlocking real business growth. Whether you’re looking to sharpen your marketing strategy, grow your career, or future-proof your skills, this episode is packed with insights to help you get there.

Fletcher Wimbush is a hiring expert who has spent his career helping business leaders build high-performing teams. We spoke about why hiring is one of the most overlooked yet crucial skills for any leader—and how to get it right every time.Hiring the right people isn’t just about intuition; it’s a process that can be systemized and refined. Fletcher knows this firsthand. After stepping into his father’s legacy, he battled imposter syndrome and set out to prove his expertise. His mission? To master hiring through relentless practice—conducting over 15,000 job interviews and advising more than 2,000 CEOs on talent selection and recruitment marketing."No one teaches us how to hire. It’s a business skill, a leadership skill that is just overlooked too often."In our conversation, Fletcher shares how most business leaders were never formally trained to hire. They learned through trial and error, often relying on gut instinct—an approach that leads to costly mistakes. He reveals a fact-driven hiring system that eliminates guesswork and ensures businesses recruit top talent while avoiding "talented terrors" and problem generators."Getting it right or wrong is the difference between hundreds of thousands, if not millions."We also explored:The three biggest hiring mistakes leaders make—and how to avoid them.Why hiring should be treated like any other process-driven business activity (and why most companies get it wrong).The role of AI and automation in streamlining recruitment.The psychology of high-performing teams and what truly makes a winning team culture.Key takeaways from our conversation include the importance of treating hiring as a structured, repeatable process rather than relying on gut feeling, the true cost of a bad hire in lost productivity and cultural damage, and the value of free hiring resources, including an eight-hour eLearning course packed with science-backed hiring strategies, which Fletcher offers for free with the promo code "hire better."Fletcher believes that hiring the right people is the key to unlocking entrepreneurial freedom. If you want to build a team that drives business success while giving you the freedom to focus on growth, this episode is a must-listen.

Mark McNally, co-founded FiltersDirectUSA and co-owner of FSI Mechanical, is an entrepreneur with a relentless drive and an inspiring journey from Belfast to the U.S., where he built multiple successful businesses from the ground up. We spoke about the leap of faith that brought him and his family across the Atlantic, the unexpected interview that landed him his first job, and how a simple pizza box prototype sparked a business that now serves 33 states.Mark’s story is one of grit, ingenuity, and sheer determination. From climbing ladders in a field he knew nothing about to co-owning a thriving mechanical company and launching a game-changing product, he proves that success isn’t about knowing everything—it’s about learning fast and taking action."You can't push a rope, but you can pull it. And I was definitely one of those people that pulled the rope, and people kind of joined me along the way."This episode uncovers:✔ The reality of starting over in a new country—with no job, no credit, and just $500 left in the bank.✔ How chance meetings at diners shaped his entrepreneurial path and why breaking bread can be the best way to land an opportunity.✔ Turning a problem into a product—how he went from cutting prototypes out of a pizza box to manufacturing a market-changing innovation.✔ Why "set it and forget it" is the ultimate business model and how automation builds both convenience and customer loyalty.Mark also shares the mindset shift that transformed his approach to work:"I thought it was just hard work and hustle. But looking back, I was always an entrepreneur—I just didn’t realize it at the time."His journey is a reminder that entrepreneurship isn’t just about making money—it’s about reclaiming your time, solving real problems, and building something that lasts.Tune in to hear how Mark navigated uncertainty, scaled his businesses without investors, and why he believes that sometimes the slow, steady path is the most rewarding.

Matthew Sanjari is a business coach and strategic consultant who knows firsthand the transformative power of pain. We spoke about how unexpected life events can not only derail plans but also reshape our understanding of success, growth, and purpose. Matthew shared his deeply personal story of surviving a life-altering accident, confronting physical and emotional pain, and rebuilding his life with clarity and intention.Matthew revealed the lessons learned from his journey, including the realization that success isn’t about numbers but about freedom and alignment with your "why." Reflecting on his struggles, he noted, "Twelve years ago, I thought my life was over because of my pain. Now, my pain has given me a career and is helping my clients."We explored his practical frameworks for business and personal growth, including:Redefining success: "What does success look like for you without using numbers?"Prioritizing effectively: Discovering the 20% of actions that drive 80% of results.Building resilience: How to adapt when plans fall apart and grow through fear.Listeners will gain actionable insights into Matthew’s four P’s—Purpose, Predictability, Productivity, and Profitability—designed to create sustainable growth. As Matthew emphasizes, "Profitability isn’t something you work on; it’s an outcome."Whether you’re an entrepreneur facing challenges, or simply seeking clarity in life, this episode offers a roadmap for transforming pain into purpose and building a foundation for lasting success.

Dikshant Dave, CEO of Zigment - Agentic AI for Performance Marketing & Selling, is a seasoned entrepreneur with over 15 years of experience, and we spoke about how AI is transforming the landscape of consultative selling. Drawing from his journey—from running a direct-to-consumer business to founding an AI-driven solution—Dikshant shared actionable insights into scaling meaningful customer engagement in an era of rapid technological change.One of the most compelling points Dikshant highlighted is the untapped potential of AI to unlock "the golden moment"—the crucial window of engaging with prospects within four minutes of their inquiry. "Your probability of conversion increases 22x if you engage instantly," he explained. This efficiency, previously unattainable with human resources alone, is now achievable at scale with AI.Dikshant’s story begins with his experience running a personalized supplementation business, where he discovered that the key to converting customers often lay in one-on-one interactions. "I started calling these customers... eight or nine out of ten would buy," he recounted. This revelation sparked the idea for building scalable AI solutions that mimic human consultations, especially in industries like healthcare, insurance, real estate, and more.We also explored the broader implications of AI adoption for businesses and society. From overcoming inefficiencies in lead management to creating new opportunities for nonprofits, Dikshant painted a hopeful vision of AI’s role in growth. His partnership with Give.org exemplifies this, enabling charities to optimize donor and volunteer engagement with limited resources.Key TakeawaysThe Golden Moment: Responding to customer inquiries within four minutes can improve conversions 22x—a capability now accessible with AI.Scaling Consultative Selling: AI empowers businesses to engage meaningfully with every customer, not just the select few.Inefficiency Overhaul: Traditional lead management often results in missed opportunities. AI eliminates delays, ensuring prospects remain engaged.AI for Good: Dikshant’s collaboration with charities showcases AI’s potential to amplify positive social impact.If you're navigating how to leverage AI for meaningful customer engagement or exploring ways technology can support societal good, this conversation offers a roadmap to possibilities.

Alex Rawitz is a seasoned entrepreneur and co-founder of DIMO, with over a decade of experience spanning technology, blockchain, IoT, and startups. We spoke about the future of connected devices, the challenges of interoperability, and how empowering individuals with control over their data can unlock tremendous value across industries.Alex shared insights on the intersection of IoT and blockchain, emphasizing the potential of machine-to-machine payments and autonomous systems. As he explained, "The world is filled with devices and sensors, and all of our cars are now smart. Cars as an IoT category are five times bigger than all other devices combined."Key topics we discussed include:Data Ownership and Ecosystems: Why giving users control over their data is critical for fostering innovation and creating value. "We believe the ultimate vision of DIMO is best achieved by building open source and helping to grow the number of contributors."The Interoperability Problem: How foundational technology needs rethinking to connect devices like autonomous vehicles and smart infrastructure.Supporting Startups: Why startups, not big corporations, will lead the next wave of transformative products. "The thing I get most excited about every day is working with entrepreneurs who are trying to start new businesses and build new products."Takeaways:The future of IoT depends on interoperable systems that enable seamless data sharing and collaboration between devices.Open-source development is crucial for building ecosystems that support innovation and growth.Empowering individuals with data control can unlock new business opportunities, from personalized insurance to carbon credits for EVs.This episode offers a fascinating glimpse into how technology can reshape industries and improve everyday experiences.