The Jason Cavness Experience
The Jason Cavness Experience where I talk to entrepreneurs and other interesting people.
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Most Entrepreneurs Should Quit — Nathan Kaiser
06/02/2026
Most Entrepreneurs Should Quit — Nathan Kaiser
Entrepreneurship isn’t freedom it’s volatility, pressure, and constant uncertainty. Nathan Kaiser built 2bar Spirits by embracing that reality, not ignoring it. He breaks down why most people shouldn’t start companies, what actually keeps a business alive, and how constraints, not capital, create better outcomes. This is a raw look at building something real in a crowded, unforgiving industry. We also discuss: • Why starting a company is usually the wrong financial move • How constraint beats capital in building a business • The myth of overnight success (and the Tito’s example) • Why focus wins over product expansion • The real role of rejection in sales and growth • How long-term thinking applies to both whiskey and life Nathan Kaiser LinkedIn: 2bar Spirits: Email: Jason links LinkedIn: Instagram: TikTok: Podcast: Website:
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Why Most Founders Mismanage Money — Morgan Rogers
05/26/2026
Why Most Founders Mismanage Money — Morgan Rogers
Most founders don’t fail because of bad ideas. They fail because they run out of moneyand don’t know why. In this episode of The Jason Cavness Experience, I sit down with Morgan Rogers from NOW CFO to break down what actually happens inside companies when the financial side isn’t dialed in. Morgan works with founders, operators, and investors every day cleaning up messy books, preparing companies for fundraising, and helping them avoid decisions that quietly destroy businesses. She’s helped scale a Seattle office by over 500% and has seen the same pattern over and over again. But the real story is this: Most founders don’t understand their numbersand it costs them everything. We get into the uncomfortable truth: cash flow problems, bad assumptions, and delayed decisions kill more companies than competition ever will. This is a video podcast available on YouTube and podcast platforms. What We Talked About • Why cash in your bank account doesn’t mean you’re profitable • The difference between a bookkeeper, controller, and CFO • When startups should actually bring in financial help • The hidden cost of messy books • Why most founders wait too long to fix financial problems • How to prepare for fundraising the right way • Why networking (done right) drives real revenue • Scaling a business development engine • When to shut down vs keep pushing forward Connect with Morgan Rogers LinkedIn: Email: Website: Connect with Jason Cavness LinkedIn: Instagram: TikTok: Podcast: Military Creator Con I’ll be speaking at Military Creator Con on leveraging content to create opportunities. Sign up here: Power Note Profit is opinion. Cash flow is reality.
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How Founders Actually Build Momentum with Nick Hughes
05/19/2026
How Founders Actually Build Momentum with Nick Hughes
From a failed startup to launching Founders Live across 155 cities and 58 countries, Nick explains what founders really need early on: community, storytelling, validation, and consistent action. He also breaks down why most people wait too long to start, how 99-second pitches force clarity, and what he’s learned traveling through startup ecosystems around the world. Nick also shares how Founders Live evolved from a simple Seattle pitch event into a global founder marketplace connecting startups with legal, development, hiring, and growth resources. We also discuss: • Why founders overthink getting started • How storytelling creates startup momentum • Building startup ecosystems outside Silicon Valley • Why the crowd votes at Founders Live • Lessons from running communities across 58 countries • What startup culture looks like in Africa and Southeast Asia • The future of Founders Live’s marketplace model • Running a global remote-first company • Nick’s upcoming 90-day Africa tour • Why entrepreneurship is a universal human drive Nick Hughes LinkedIn Nick Hughes Instagram Founders Live Jason Links Also check out The Jason Cavness Experience Deep Tech Demo Day during Seattle Deep Tech Week. A showcase bringing together founders, investors, operators, and emerging deep tech startups across the Seattle ecosystem. https://www.deep-tech-week.com/seattle-2026/events/the-jason-cavness-experience-deep-tech-demo-day-part-of-seattle-deep-tech-week
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Why Most Teams Are Broken — Mimi Nguyen
05/12/2026
Why Most Teams Are Broken — Mimi Nguyen
Most teams don’t fail because of strategy. They fail because people can’t align. In this episode of The Jason Cavness Experience, I sit down with Mimi Nguyen to break down why teams struggle to work together and what actually fixes it. Mimi has lived across Vietnam, the United States, and Malaysia, and brings a rare perspective on culture, communication, and decision-making. She’s led initiatives that drove a $7M+ uplift and achieved 90% product adoption. But the real story is how she got teams to stop working against each other. We get into the uncomfortable truth: misaligned incentives, poor communication, and lack of trust kill more progress than bad ideas ever will. This is a video podcast available on YouTube and podcast platforms. What We Talked About • Why most teams are misaligned from the start • The real reason projects fail inside companies • How Mimi aligned marketing, sales, and operations • The $7M+ uplift project breakdown • Driving 90% adoption through behavior change • Why trust is harder than data • Data vs intuition in decision-making • The limits of AI in data science • Cultural intelligence as a competitive advantage • Living and working across Vietnam, Malaysia, and the U.S. • Fear of putting yourself out there and staying private Connect with Mimi Nguyen LinkedIn: Connect with Jason Cavness LinkedIn: Instagram: TikTok: Podcast: Military Creator Con I’ll be speaking at Military Creator Con on leveraging content to create opportunities. Sign up here: Power Note Alignment beats intelligence. Every time.
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Why Small Businesses Struggle — Hugo Nicolas
05/05/2026
Why Small Businesses Struggle — Hugo Nicolas
Most small businesses don’t fail because of bad ideas. They fail because they don’t understand the system. In this episode of The Jason Cavness Experience, I sit down with Hugo Nicolas from Washington State’s Office for Regulatory Innovation and Assistance (ORIA) to break down what actually stops businesses from growing. Hugo went from a small village in Mexico to helping thousands of business owners navigate permits, licenses, and government processes. He’s seen firsthand where people get stuck and it’s not where most think. We get into the real problems: confusing regulations, lack of awareness, and why too many founders ignore the “unsexy” parts of business until it’s too late. If you’re building a business or thinking about itT his episode will save you time, money, and frustration. This is a video podcast available on YouTube and podcast platforms. What We Talked About • Why most small businesses fail (and it’s not the idea) • The hidden cost of ignoring permits and regulations • Hugo’s journey from undocumented immigrant to state leader • The biggest mistakes new business owners make • Why business structure matters more than you think • How to navigate government without wasting time • Free resources most entrepreneurs never use • The power of resilience and adapting fast Connect with Hugo Nicolas LinkedIn: Website: Connect with Jason Cavness LinkedIn: Instagram: TikTok: Podcast: Military Creator Con I’ll be speaking at Military Creator Con on how to leverage content to create opportunities. Sign up: Power Note The difference between struggling and scaling is not effort. it’s knowing how to navigate the system.
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Tattoo Culture, Craft, and Business with Tim McCarthy
04/28/2026
Tattoo Culture, Craft, and Business with Tim McCarthy
In this episode of The Jason Cavness Experience, I sit down with Tim McCarthy, owner of Tsunami Tattoo in Tacoma and a veteran tattoo artist with more than three decades of experience in the industry. Tim shares his journey from starting tattooing in 1989 to apprenticing in Denver, working in San Jose and Albuquerque, and eventually building Tsunami Tattoo into one of Tacoma’s most respected tattoo shops. We talk about how tattoo culture has evolved over the years, the discipline required to become a great tattoo artist, and what it takes to run a successful tattoo business. We also discuss the importance of apprenticeship, how artists develop their style, and why trust between artist and client is critical when creating permanent artwork. Tim explains how the industry has changed with social media and how shops like Tsunami Tattoo continue to build strong reputations through craftsmanship and consistency. This episode is a video podcast available on YouTube and podcast platforms. What We Talked About • Tim McCarthy’s start in tattooing in 1989 • Apprenticing in Denver and early tattoo career • Working in San Jose and Albuquerque tattoo shops • Opening and growing Tsunami Tattoo in Tacoma • How tattoo culture has evolved over the decades • The apprenticeship path for tattoo artists • Building trust between artist and client • The impact of social media on tattoo artists and shops • Running a long-term creative business Connect with Tsunami Tattoo Website: Instagram: TikTok: Connect with Tim McCarthy Instagram: Connect with Jason Cavness LinkedIn: Instagram: TikTok: Podcast: Power Note Great tattoo artists combine creativity, discipline, and trust. Tim McCarthy’s decades of work show how craftsmanship and reputation build lasting businesses in creative industries.
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Local Politics, Schools, and Public Safety — Ryan Logan
04/21/2026
Local Politics, Schools, and Public Safety — Ryan Logan
In this episode of The Jason Cavness Experience, I talk with Ryan Logan, a teacher and political candidate running for Washington State House. Ryan shares his perspective on education, community safety, and the policy challenges facing South King County. Ryan discusses what motivated him to step into politics, how his work in the Auburn School District shaped his views, and why he believes more community members should participate in civic leadership. We also explore the realities teachers face in classrooms today, the intersection of public policy and education, and the broader issues affecting communities across Washington State. This conversation covers local governance, political accountability, and what it takes to step forward as a candidate when you believe your community needs change. This episode is a video podcast available on YouTube and podcast platforms. Topics Discussed • Ryan Logan’s background growing up in Renton and Kent • His work in the Auburn School District • Why he decided to run for Washington State House • Challenges facing public education today • The impact of drug addiction and public safety issues in local communities • Civic engagement and community involvement • Policy priorities for South King County • What voters should understand about local government Connect with Ryan Logan Website: Email: Phone: (253) 249-6408 Connect with Jason Cavness LinkedIn: Instagram: TikTok: Podcast: Power Note Change in communities often begins with individuals who decide to step forward. Conversations like this highlight how civic engagement, leadership, and local action shape the future of neighborhoods and cities.
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Josh Kotoff on YouTube Strategy, Creator Optimization, and Building a High-Performance Content Engine
04/14/2026
Josh Kotoff on YouTube Strategy, Creator Optimization, and Building a High-Performance Content Engine
In this episode of The Jason Cavness Experience, I sit down with Josh Kotoff to break down YouTube strategy, creator growth, and what most founders get wrong about content optimization. Josh conducted a deep dive into my YouTube channel and turned that audit into a tactical discussion on positioning, thumbnails, titles, structure, and audience clarity. This conversation is a masterclass on treating content like a long-term leverage asset instead of a vanity metric. If you're serious about building a content engine that compounds, this episode delivers practical insight. What We Cover • Conducting a YouTube channel audit • Why most YouTube channels stall • Title and thumbnail strategy for higher click-through rates • Viewer psychology and retention strategy • Audience clarity and channel positioning • Structuring long-form content for performance • Turning podcasts into strategic assets • Data vs instinct in creator growth • Building consistency without burnout • Treating content like a business system Josh focuses on the fundamentals packaging, positioning, and performance metrics that compound over time rather than chasing trends. Military Creator Con I’m a featured speaker at Military Creator Con. A conference for veterans, creators, and entrepreneurs building brands and businesses intentionally. If you're monetizing attention or building a content brand, this is the room to be in. Sign up here: Connect with Josh Josh's LinkedIn: Josh's Instagram: Company Website: https://www.bluestreamyoutubeagency.com/ Connect with Jason Cavness LinkedIn: Instagram: TikTok: Podcast:
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Military Creator Con Speaker: Most Veterans Are Doing It Wrong
04/07/2026
Military Creator Con Speaker: Most Veterans Are Doing It Wrong
Military Creator Con is where Veteran builders, creators, and operators level up and this conversation shows why that matters. Travis Partington breaks down the uncomfortable truth: most veterans stay stuck because they never adapt after service. From rebuilding after a career-ending injury to building Oscar Mike Radio into a mission-driven platform, this is about ownership, discipline, and doing the work long after the uniform comes off. We also discuss: • Why most veterans struggle after leaving the military • The entitlement vs responsibility mindset gap • Why most podcasts fail before episode 10 • How Travis built Oscar Mike Radio over 9+ years • Community access TV as an underrated growth channel • The power of consistency over talent Military Creator Con Jason Cavness speaking April 17 at 2PM Arlington Hilton Discount codes: JasonC10 JasonC50 Travis’ links LinkedIn: Facebook: Website: Email: Travis@oscarmikeradio.com YouTube: Connect with Jason Cavness LinkedIn: Instagram: TikTok: Podcast: YouTube: Website:
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Dr. Badri Narayanan Gopalakrishnan on Global Economic Strategy, Trade Policy, and Vision India@2047
03/31/2026
Dr. Badri Narayanan Gopalakrishnan on Global Economic Strategy, Trade Policy, and Vision India@2047
On this episode of The Jason Cavness Experience, I sit down with Dr. Badri Narayanan Gopalakrishnan. Economist, global strategy leader, policy advisor, and academic with nearly 25 years of international experience. Dr. Badri has served as Joint Secretary at NITI Aayog (Government of India), where he led Trade and Commerce, Strategic Economic Dialogue, International Cooperation, and Vision India@2047. He currently serves as an Honorary Non-Resident Fellow at NITI Aayog and holds multiple global academic and policy appointments. With 15 published books, over 250 research papers, and thousands of academic citations including work published in Nature. Dr. Badri brings deep perspective on global trade, economic diplomacy, sustainability, and long-term development strategy. We discuss: • The future of global trade and economic realignment • India’s Vision 2047 and long-term strategic planning • U.S.–India economic relations • International cooperation in a multipolar world • Economic modeling and policy impact • Sustainability and climate strategy • Bridging academia, government, and industry • Advising the World Bank, IMF, Google, Amazon, USDA, McKinsey, and more • Long-term economic strategy vs short-term cycles Dr. Badri also shares insights from founding Infinite Sum Modelling LLC, a global advisory firm with offices across North America, the Middle East, Africa, and Asia advising over 100 organizations worldwide. This episode is especially valuable for founders, policymakers, investors, and leaders thinking beyond quarterly cycles and toward generational strategy. Military Creator Con I’m a featured speaker at Military Creator Con, a conference bringing together veterans, creators, and entrepreneurs focused on building brands, businesses, and long-term leverage. If you’re serious about turning experience into opportunity, this is the room to be in. Sign up here: What We Talked About • Leading trade and economic strategy at NITI Aayog • Vision • Economic diplomacy and global cooperation • Sustainability and environmental strategy • Academic research influencing policy • Founding Infinite Sum Modelling • Advising governments and global corporations • Long-term economic planning Connect with Dr. Badri Narayanan Gopalakrishnan LinkedIn: Company Website: Personal Academic Site: X (Twitter): @badrinarayanang Connect with Jason Cavness LinkedIn: Instagram: TikTok: Podcast:
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Christopher Seminatore on Geofencing, Precision Marketing, and Building a 7-Figure Veteran-Owned Agency
03/24/2026
Christopher Seminatore on Geofencing, Precision Marketing, and Building a 7-Figure Veteran-Owned Agency
In this episode of The Jason Cavness Experience, I sit down with Christopher Seminatore. U.S. Navy Veteran and founder of GetGeofencing.com to break down precision marketing, location-based advertising, and how he bootstrapped a 7-figure agency without outside funding. Christopher shares how his military experience shaped his approach to entrepreneurship, risk, and execution. We unpack what geofencing actually is, how it works, and why location-based targeting is becoming one of the most effective forms of digital advertising. Instead of broad, spray-and-pray marketing, Christopher focuses on precision drawing digital boundaries around physical locations and delivering ads directly to devices within those zones. We also discuss: • Transitioning from military service to entrepreneurship • Bootstrapping without investors • How geofencing marketing works in simple terms • Precision targeting vs traditional digital ads • Building recurring revenue • Competitor targeting strategies • Remote-first business systems • Discipline and long-term execution Christopher proves you don’t need venture capital to scale. You need clarity, systems, and consistent follow-through. If you’re a founder, marketer, or v Veteran entrepreneur serious about monetizing attention with precision, this episode delivers practical insight. Military Creator Con I’m a featured speaker at Military Creator Con, where veterans, creators, and entrepreneurs come together to turn content and audience into opportunity. If you’re building a brand or monetizing content, this is the room to be in. Sign up to attend here: Connect with Christopher Seminatore LinkedIn: Website: Instagram: @chrisseminatore Connect with Jason Cavness LinkedIn: Instagram: TikTok: Podcast: https://www.thejasoncavnessexperience.com
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Vaishnavi Balakrishnan on Building SWANN, Youth Leadership, and Advancing Girls’ Health & Education
03/17/2026
Vaishnavi Balakrishnan on Building SWANN, Youth Leadership, and Advancing Girls’ Health & Education
in this episode of The Jason Cavness Experience, I sit down with Vaishnavi Balakrishnan, student entrepreneur and founder of SWANN (Student-Led Women’s Adolescent Needs Navigation Conference). Vaishnavi shares how she built a youth-led initiative focused on young girls’ health, development, and how those issues directly impact education outcomes. We discuss the origin of SWANN, the gaps she saw in awareness and support systems, and how she mobilized professionals, educators, and community leaders around the issue. We also explore: • Starting a mission-driven organization as a student • Leadership lessons from building SWANN • The intersection of health and education for young women • Organizing conferences and mobilizing community stakeholders • Balancing academics, athletics, and entrepreneurship • Long-term goals in finance, investment banking, and C-suite leadership Vaishnavi represents a new generation of leaders who are not waiting for permission to build impact. This episode is especially relevant for young founders, student leaders, and anyone interested in education reform, women’s health, and youth entrepreneurship. What We Talked About • The founding of SWANN • Why adolescent health impacts education outcomes • Community engagement and conference organization • Leadership development at a young age • Balancing school, athletics, and entrepreneurship • Long-term career vision in finance and leadership Connect with Vaishnavi Balakrishnan LinkedIn: SWANN Website: Connect with Jason Cavness LinkedIn: Instagram: TikTok: https://www.tiktok.com/@jasoncavness Podcast:
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Vikram Chalana on Building Pictory, Democratizing Video with AI, and Scaling a Global SaaS Platform
03/10/2026
Vikram Chalana on Building Pictory, Democratizing Video with AI, and Scaling a Global SaaS Platform
In this episode of The Jason Cavness Experience, Jason sits down with Vikram Chalana, co-founder of Pictory, to talk about building an AI-powered video platform designed to simplify content creation for creators, educators, and businesses. Vikram shares how Pictory was built to remove the complexity from video production and content repurposing. We discuss scaling a SaaS company, leading product and engineering teams, and how AI is reshaping content creation workflows. The conversation also explores Vikram’s earlier experience co-founding Winshuttle, lessons learned from building enterprise software, and how those insights shaped Pictory’s product strategy. Jason and Vikram talk about the future of AI in media, founder discipline, and what it takes to turn a technical idea into a widely adopted product. This episode is especially valuable for founders, SaaS builders, product leaders, and anyone leveraging AI to scale content and business growth. Topics Discussed • Vikram’s path into entrepreneurship • Founding and scaling Pictory • Democratizing video creation with AI • Leading product and engineering teams • Lessons from building enterprise software • SaaS growth and customer adoption • AI’s role in content repurposing • Startup discipline and execution • Building technology for creators and businesses • The future of AI-driven media Connect with Vikram Chalana LinkedIn: Pictory Website: Connect with Jason Cavness LinkedIn: Instagram: TikTok: Podcast:
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Taylor Rae at Military Creator Conference: Geofencing, AI in Marketing
03/03/2026
Taylor Rae at Military Creator Conference: Geofencing, AI in Marketing
In this episode of The Jason Cavness Experience, I sit down with Taylor Rae, founder of Rae Enterprise and the Success Club App, and a participant at Military Creator Conference. We talk about how marketing strategy, community building, and disciplined execution intersect for creators and founders. Taylor breaks down how she built Rae Enterprise around geofencing and programmatic display advertising, helping businesses target the right customers with precision. During the episode, she walks through a live-style demo explaining how geofencing actually works. Showing how businesses can draw digital perimeters around physical locations and serve ads directly to devices that enter those areas. We discuss the role AI now plays in marketing, how founders should think about automation, and why creativity still matters. We also explore the Success Club App. Her platform designed to connect entrepreneurs and foster accountability-driven growth. As part of Military Creator Conference, Taylor represents creators who are turning marketing skillsets into scalable businesses. We discuss what creators often misunderstand about growth, how to build real community instead of vanity metrics, and why long-term positioning beats short-term hype. If you're a creator, founder, or marketer trying to build something sustainable, this conversation delivers practical insight. What We Talked About • Participating in Military Creator Conference • A practical demo of how geofencing works • Building Rae Enterprise through targeted marketing • AI’s role in modern marketing strategy • Programmatic advertising and customer targeting • Launching and scaling the Success Club App • Community-building vs follower counts • Founder discipline and long-term positioning • Applying strategic thinking from poker to business Connect with Taylor Rae LinkedIn: Instagram (Marketing): Instagram (Success Club App): https://www.instagram.com/our.success.club/ Military Creator Conference Website: Connect with Jason Cavness LinkedIn: Instagram: TikTok: Podcast:
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Barry Gipson on Military Creator Con, Facebook Monetization, and Building a Veteran Content Brand
02/24/2026
Barry Gipson on Military Creator Con, Facebook Monetization, and Building a Veteran Content Brand
In this episode of The Jason Cavness Experience, I sit down with Barry Gipson, better known as the Cowboys Unifier content creator, Dallas Cowboys superfan, and featured speaker at Military Creator Con. Barry shares how he built and monetized a content brand rooted in sports, community, and veteran identity. We break down how Facebook monetization actually works, how he generates revenue from memes and engagement, and why most creators quit before the real results show up. Barry is not just attending Military Creator Con. He’s a featured speaker, sharing lessons from a decade of content discipline, audience building, and platform monetization. As a veteran creator, he represents what’s possible when you combine consistency, niche focus, and community-first thinking. We also discuss: • How Barry monetized Facebook and built recurring revenue • Turning passion into a sustainable content business • Why veterans have an advantage in discipline and execution • Planning content like a long-term brand, not a viral gamble • The psychology of algorithms and audience loyalty • Dealing with critics and staying consistent • Why niche audiences outperform broad appeal • What he’ll be sharing on stage at Military Creator Con Barry proves you don’t need a studio setup to win. You need focus, repetition, and the willingness to show up for years. If you're a veteran creator, entrepreneur, or someone serious about monetizing social platforms, this episode delivers practical insight. Connect with Barry Gipson LinkedIn: Website: Facebook: Military Creator Con Website: Connect with Jason Cavness LinkedIn: Instagram: TikTok: Podcast: Be Great Every Day!
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Emily Power on Seaweed Innovation, Regenerative Products, and Building Ocean-Positive Businesses
02/17/2026
Emily Power on Seaweed Innovation, Regenerative Products, and Building Ocean-Positive Businesses
In this episode of The Jason Cavness Experience, Jason sits down with Emily Power, founder of Ocean Made, to talk about seaweed, sustainability, and building regenerative consumer products. Emily shares how leaving a corporate career led her to an unexpected obsession with kelp a material that cleans polluted water, captures carbon faster than trees, and helps rebuild ocean ecosystems. She explains how that fascination turned into Ocean Made and the creation of Kelp Pots, plant containers designed to replace billions of single-use plastic pots thrown away every year. The conversation explores the challenges of building climate-positive products, why good intentions aren’t enough to change consumer behavior, and how entrepreneurs can design products that are both better for the planet and better for customers. Emily also talks about the realities of entrepreneurship, collaboration, and what it takes to bring sustainable innovation to market. This episode is especially valuable for founders, makers, and anyone interested in climate tech, consumer products, and the blue economy. Topics Discussed • Emily’s journey from corporate work to entrepreneurship • Discovering seaweed as a regenerative material • How kelp supports ocean health and carbon capture • Founding Ocean Made and launching Kelp Pots • Replacing single-use plastic in consumer products • Designing products that shift consumer behavior • Building climate-positive businesses • The realities of sustainable manufacturing • Collaboration in ocean conservation • Balancing purpose with product performance • Lessons learned as a reluctant entrepreneur Connect with Emily Power LinkedIn: Website: Connect with Jason Cavness LinkedIn: Instagram: TikTok: Podcast:
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Wesley Nicholson on Leadership, Community, and Building Two Maids of Kent
02/10/2026
Wesley Nicholson on Leadership, Community, and Building Two Maids of Kent
In this episode of The Jason Cavness Experience, Jason sits down with Wesley Nicholson, owner of Two Maids of Kent, to talk about leadership, entrepreneurship, and building a service business rooted in community impact. Wesley shares how his background in the U.S. Navy and years of leadership experience at Amazon shaped his approach to running a people-first business. He discusses the transition from corporate leadership to small business ownership, the challenges of scaling a service business, and why culture and training matter just as much as operational excellence. The conversation also explores Wesley’s commitment to giving back, including Two Maids’ mission of providing free cleanings to individuals battling cancer. Jason and Wesley talk about learning from mistakes, addressing blind spots as a leader, and creating opportunities for team members to grow. This episode is especially valuable for founders, operators, and anyone building a local service business with purpose. Topics Discussed • Wesley’s background in the Navy and Amazon • Transitioning from corporate leadership to entrepreneurship • Building and growing Two Maids of Kent • Leadership lessons from military and corporate environments • Creating a strong team culture in a service business • Training, accountability, and operational discipline • Giving back through community-focused initiatives • Learning from mistakes and addressing leadership blind spots • Balancing growth with quality and trust • Defining success beyond revenue Connect with Wesley Nicholson LinkedIn: Connect with Two Maids of Kent Website: Facebook: Connect with Jason Cavness LinkedIn: Instagram: TikTok: Podcast:
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Hans Bjordahl on Digital Transformation, Culture-Led Design, and Building Technology That Actually Works
02/03/2026
Hans Bjordahl on Digital Transformation, Culture-Led Design, and Building Technology That Actually Works
In this episode of The Jason Cavness Experience, Jason sits down with Hans Bjordahl, co-founder and CEO of Culture Foundry, to talk about digital transformation, experience-driven design, and what it really takes to build technology that serves people and organizations effectively. Hans shares his background in building and leading digital teams, how Culture Foundry approaches complex modernization projects, and why culture, process, and people matter just as much as technology. He explains how many digital transformation efforts fail not because of bad tools, but because of misalignment between strategy, execution, and organizational culture. The conversation explores user-centered design, modern content platforms, government and enterprise digital work, and what leaders should prioritize when modernizing legacy systems. Hans also discusses leadership, scaling teams, and how to create digital products that are both functional and human-centered . This episode is especially valuable for founders, operators, and leaders navigating digital transformation in complex or regulated environments. Topics Discussed • Hans’s background and path to founding Culture Foundry • What digital transformation really means in practice • Why culture and alignment matter in technology projects • User-centered and experience-driven design • Modernizing legacy platforms and systems • Common mistakes organizations make during digital transformation • Balancing strategy, design, and engineering • Leadership lessons from scaling digital teams • Building technology that actually gets adopted • Long-term thinking in enterprise and government tech Connect with Hans Bjordahl LinkedIn: Connect with Culture Foundry Website: Instagram: Connect with Jason Cavness LinkedIn: Instagram: TikTok: Podcast:
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Akalpit Gadre on Technical Leadership, Quantum Computing, and Building in Cloud, AI, and Cybersecurity
01/27/2026
Akalpit Gadre on Technical Leadership, Quantum Computing, and Building in Cloud, AI, and Cybersecurity
In this episode of The Jason Cavness Experience, Jason sits down with Akalpit Gadre, a technologist and founder with deep experience in technical leadership, cloud computing, cybersecurity, and emerging technologies. Akalpit shares his journey as a foundry entrepreneur, how he approaches building technology-driven companies, and what strong technical leadership looks like in practice. He talks about navigating complexity in cloud systems, the importance of security-first thinking, and how founders and technical leaders should evaluate new technologies without getting distracted by hype. The conversation also explores problem-solving at scale, decision-making under uncertainty, and what it takes to build resilient systems and teams in fast-moving technical environments. This episode is especially valuable for founders, engineers, and operators building products in AI, cloud, and security-focused spaces. Topics Discussed • Akalpit’s background and path into technical leadership • What it means to be a foundry entrepreneur • Building and scaling cloud-based systems • Cybersecurity as a foundational design principle • Evaluating new technologies without chasing hype • Leadership lessons from technical teams • Problem-solving in complex systems • Balancing innovation with reliability • How founders should think about technical tradeoffs • Long-term thinking in engineering and architecture Connect with Akalpit Gadre LinkedIn: Website: Connect with Jason Cavness LinkedIn: Instagram: TikTok: Podcast: https://www.thejasoncavnessexperience.com
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Sabina Nawaz on Executive Presence, Power, and What Changes When You Become the Boss
01/20/2026
Sabina Nawaz on Executive Presence, Power, and What Changes When You Become the Boss
In this episode of The Jason Cavness Experience, Jason sits down with Sabina Nawaz, an executive coach and leadership advisor who works with founders, CEOs, and senior leaders navigating power, influence, and responsibility at the highest levels. Sabina shares what she’s learned from years of coaching executives as they step into positions of authority and why leadership often becomes harder, not easier, as power increases. She explains how authority subtly changes behavior, how communication breaks down at the top, and why well-intentioned leaders can unintentionally create silence, fear, or distance on their teams. Jason and Sabina discuss executive presence, emotional regulation, feedback, and how leaders can stay grounded and human while still holding accountability. Sabina also talks about the ideas behind her book, You're the Boss, and what leaders need to understand once they’re officially “in charge.” This episode is especially valuable for founders, CEOs, and operators who are scaling their influence and want to lead with clarity, self-awareness, and trust. Topics Discussed • How power changes leadership behavior • Why communication often breaks down at senior levels • Executive presence and influence • Managing authority without creating fear • Feedback loops and honest conversations • Emotional regulation for leaders • Listening as a core leadership skill • Blind spots that appear as leaders gain power • Staying human while holding accountability • Coaching executives through high-stakes decisions • Lessons from working with CEOs and founders • What changes when you officially become “the boss” Connect with Sabina Nawaz LinkedIn: Website: https://sabinanawaz.com/ Instagram: Book – You’re the Boss: Connect with Jason Cavness LinkedIn: Instagram: TikTok: Podcast:
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Tait Covert on Building Sentry Computing and Practical IT Leadership
01/13/2026
Tait Covert on Building Sentry Computing and Practical IT Leadership
In this episode of The Jason Cavness Experience, Jason sits down with Tait Covert, President and CEO of Sentry Computing, to talk about building a service-first managed IT company and what it really takes to support small and mid-sized businesses. Tait shares his path into entrepreneurship, how his background in retail sales, graphic design, and project management shaped his approach to IT, and why clear communication and transparent guidance matter more than technical jargon. He explains how Sentry Computing delivers contract-free managed IT services, prioritizes cybersecurity and reliability, and focuses on long-term client relationships over quick wins. The conversation also covers leadership, customer trust, running a people-first services business, and how business owners should think about IT strategy without getting overwhelmed. This episode is especially valuable for founders, operators, and business owners who want practical insight into IT, cybersecurity, and building a service company that lasts. Topics Discussed • Tait’s background and journey into entrepreneurship • Founding and growing Sentry Computing • What “service-first IT” really means • Communicating technical concepts without jargon • Cybersecurity basics business owners must understand • Building trust with small and mid-sized businesses • Leadership lessons from running an IT services company • Balancing technical expertise with customer experience • What business owners should prioritize in their IT strategy Connect with Tait Covert LinkedIn: Connect with Sentry Computing Website: Instagram: Connect with Jason Cavness LinkedIn: Instagram: TikTok: Podcast:
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Shonta Riles on Building Poppin Notary, Community Trust, and Expanding a Local Service Business
01/06/2026
Shonta Riles on Building Poppin Notary, Community Trust, and Expanding a Local Service Business
In this episode of The Jason Cavness Experience, Jason sits down with Shonta Riles, CEO and founder of Poppin Notary, to talk about building a trusted local service business, expanding beyond traditional notary work, and staying deeply connected to the community. Shonta shares how he launched Poppin Notary in 2016, what it took to earn trust in an industry built on accuracy and reliability, and why customer service is the real differentiator for small businesses. He explains how his background hosting the Deprogram Talk Radio Show sharpened his communication skills and helped him connect with people from all walks of life. The conversation explores Poppin Notary’s expansion into shipping, printing, and private mailboxes, how Shonta thinks about growth without losing focus, and why building locally in Tacoma still matters. From notarizing documents in non-traditional settings to creating a one-stop service hub, this episode offers practical lessons for service-based entrepreneurs. Topics Discussed • Shonta’s path to entrepreneurship and founding Poppin Notary • Building trust in a service-based business • What great customer service looks like in practice • Lessons from notarizing documents in unconventional environments • Expanding into shipping, printing, and private mailboxes • Knowing when to add new services • Avoiding overextension while growing • Building a business rooted in community • The Tacoma small business landscape • Communication skills developed through radio and media • Leadership lessons learned as a local CEO • Defining success beyond revenue Connect with Shonta Riles LinkedIn: Website: TikTok: Instagram:
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Taylor Black on AI, Startups, Microsoft, and Building a Life Through Foster Care and Adoption
12/30/2025
Taylor Black on AI, Startups, Microsoft, and Building a Life Through Foster Care and Adoption
In this episode of The Jason Cavness Experience, Jason sits down with Taylor Black for a wide-ranging conversation that spans AI, startups, big tech, and family life. Taylor shares his experience working at Microsoft, where he’s been close to how AI is being built, adopted, and misunderstood inside large organizations. He talks about how startups and founders should think about AI realistically not as hype, but as a tool that rewards clarity, discipline, and execution. Beyond tech, Taylor opens up about his family’s journey through fostering and adoption, what it’s taught him about responsibility, patience, and long-term thinking, and how building a family reshapes how you approach work and leadership. He reflects on balancing ambition with presence, and why success isn’t just about what you build professionally, but what you commit to personally. This is an honest conversation about building companies, adopting new technology responsibly, and choosing to show up fully at work and at home. Topics Discussed • Taylor’s role at Microsoft and exposure to AI at scale • How large companies actually adopt AI • The gap between AI hype and real-world execution • How startups should think about using AI • Discipline and clarity as advantages in tech and business • Lessons from working inside a major tech company • Fostering and adopting children and what it teaches about leadership • Balancing startup ambition with family responsibility • Long-term thinking in both business and life • Redefining success beyond career milestones Support CavnessHR CavnessHR is building an AI-native HR system for small businesses with 49 or fewer employees automation plus a dedicated HR Business Partner. Invest on Wefunder Download 7 free eBooks Join the Builders Club Connect with Taylor Black LinkedIn:
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Scott Strong on Sales Discipline, Customer Service and Building a Service-First Business
12/23/2025
Scott Strong on Sales Discipline, Customer Service and Building a Service-First Business
In this episode of The Jason Cavness Experience, Jason sits down with Scott Strong, founder of Strong Fiber Systems, to talk about building a service-first business in the telecom industry and why sales discipline and customer service still matter in a world obsessed with automation. Scott shares his journey into entrepreneurship, how he built Strong Fiber Systems by focusing on relationships and trust, and why doing the unscalable work, personal outreach, follow-ups, and real conversations creates a lasting competitive advantage. He explains the difference between motivation and discipline in sales, how strong habits outperform hype, and why customer service is becoming a lost art. The conversation also covers leadership, networking without forcing outcomes, using AI without losing the human element, and what it really takes to build a business you can stand behind long term. This episode is packed with practical insight for founders, operators, and sales leaders building service-based companies. Topics Discussed • Scott’s path into telecom and entrepreneurship • Building Strong Fiber Systems from the ground up • Sales discipline vs motivation • Why doing the unscalable work still wins • Customer service as a true differentiator • Picking up the phone instead of hiding behind email • Using AI to support sales without removing humanity • Networking with authenticity • Leadership, habits, and long-term thinking Support CavnessHR CavnessHR is building an AI-native HR system for small businesses with 49 or fewer employees combining automation with a dedicated HR Business Partner. Invest on Wefunder Download 7 free eBooks Join the Builders Club Connect with Scott Strong LinkedIn: Company: Phone: (888) 601-0123 Connect with Jason Cavness LinkedIn: TikTok: Podcast:
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Brandie Henry on Communication, Dance, Hip Hop, Leadership and Serving Youth and Families
12/16/2025
Brandie Henry on Communication, Dance, Hip Hop, Leadership and Serving Youth and Families
In this episode of The Jason Cavness Experience, Jason sits down with Brandie Henry. A communication coach, consultant, educator and community advocate whose work bridges personal development, professional leadership, youth services and creative expression. Brandie runs S4S Management, where she coaches leaders on communication, clarity and emotional intelligence, while also serving the community through her work with Southwest Youth and Family Services (SWYFS). Brandie shares how her early foundation in dance shaped her understanding of expression, confidence and presence long before she ever studied communication formally. She talks about the connection between rhythm, movement and emotional awareness, and how hip hop’s influence helped her develop a grounded and authentic communication style. Jason and Brandie dig into communication patterns, nervous system regulation, leadership, community programs, family support, and how growing up around hip hop culture gives people an intuitive understanding of timing, energy and storytelling. They even get into her Top 5 rappers list and why those artists shaped her perspective. This is a memorable, wide-ranging conversation that blends leadership, creativity, culture and community impact. Topics Discussed • How dance shaped Brandie’s early communication skills • The influence of hip hop on expression, confidence and storytelling • Brandie’s Top 5 rappers list and why each one matters • How she helps leaders communicate with clarity and emotional awareness • The mission of S4S Management and the people she serves • Trauma-informed communication and why presence matters • Brandie’s work supporting families at Southwest Youth & Family Services • What youth and parents need most from community programs • How nervous system regulation affects communication • Why people fall into autopilot when speaking or listening • Creating safe spaces for difficult conversations • Leadership, awareness, identity and authenticity • Brandie’s advice for anyone who wants to communicate with more intention Support CavnessHR Invest on Wefunder: Download 7 free eBooks: Join the Builders Club: Connect with Brandie Henry LinkedIn: Her Company – S4S Management: Southwest Youth & Family Services:
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Liz Galloway on Adventure, Branding, Storytelling and Building a Life Without Limits
12/12/2025
Liz Galloway on Adventure, Branding, Storytelling and Building a Life Without Limits
In this episode of The Jason Cavness Experience, Jason sits down with Liz Galloway a global brand strategist, PR pro, experiential marketer, storyteller, TEDx curator, wellness advocate, and adventure-driven entrepreneur. Liz’s work spans luxury hospitality, wellness retreats, publishing, consulting, media production and high-impact brand development across Central America, Europe and the U.S. Liz shares how she built a life and career around curiosity, creativity and courage blending strategy with soul to help brands cut through noise and connect with people on a deeper level. She and Jason explore the power of storytelling, experiential branding, adventure as a lifestyle, and why reinvention is essential for personal and professional growth. A vibrant, wide-ranging conversation full of insights for creatives, founders, marketers and anyone designing a meaningful life or meaningful work. Topics Discussed • Liz’s background in branding, PR and experiential marketing • What makes a story compelling in today’s world • Why strong brands need emotional resonance, not just visuals • Adventures that shaped her perspective and leadership style • The rise of experiential marketing and immersive experiences • How she coaches TEDx speakers and curates powerful talks • Building wellness, travel and transformational retreats • Authentic storytelling in the age of social media • Balancing creativity with business execution • How to build a brand people genuinely care about • Liz’s advice for founders reinventing themselves Support CavnessHR CavnessHR is building an AI-native HR system for small businesses with 49 or fewer employees automation plus a dedicated HR Business Partner. Invest on Wefunder: Download 7 free eBooks: Join the Builders Club: Connect with Liz Galloway LinkedIn: Website: Instagram:
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HR Laws Every Small Business Owner Must Follow: A Practical Breakdown for Companies with 49 or Fewer Employees
12/09/2025
HR Laws Every Small Business Owner Must Follow: A Practical Breakdown for Companies with 49 or Fewer Employees
In this solo livestream episode, Jason Cavness walks small business owners through the HR laws you must follow when you have 49 or fewer employees. Jason draws from more than 30 years of HR experience, 25 years as a retired U.S. Army officer, and over a decade working with startups to explain complicated HR rules in a simple, practical way. Jason covers what federal government actually requires, why most HR mistakes come from confusion rather than bad intent, and how ignoring even one rule can lead to fines, audits, lawsuits, and massive headaches for small business owners. Using real examples, stories from his career, and questions from livestream viewers, Jason breaks down what every employer needs to know: overtime rules, payroll tax obligations, discrimination laws, onboarding requirements, union rules, ADA accommodations, pregnancy protections, military employment rights, OSHA issues, misclassification risks, and more. If you’re a founder, small business owner, or early-stage startup leader, this episode gives you a straightforward roadmap for staying compliant and protecting your business before something goes wrong. Topics Discussed • Why HR feels complicated and why it really isn’t • The real reason most small businesses get fined • Drug-Free Workplace Act and who it does and does not apply to • Audio monitoring vs video monitoring rules • Polygraph testing and the extremely rare cases where it’s allowed • Military employment rights and what employers must provide • Workplace safety, chemical safety sheets, and OSHA basics • Employee rights to discuss wages, schedules, and working conditions • Equal Pay Act misunderstandings and why negotiation habits matter • Minimum wage, overtime, exempt vs non-exempt rules • Why you must pay overtime even when you tell someone not to work it • I-9 verification, E-Verify, and immigration compliance • Payroll tax responsibilities • ADA and reasonable accommodation requirements • Pregnancy discrimination and common employer mistakes • Genetic information discrimination and health insurance issues • Title VII Civil Rights Act protections • LGBTQ workplace protections • Age discrimination rules and why age 40 is the legal threshold • COBRA continuation for companies offering health benefits • Worker misclassification and how calling someone a contractor doesn’t make them one • Why unions form and how employers accidentally trigger unionization • What CavnessHR is building to automate HR and prevent these problems Support CavnessHR CavnessHR is building an AI-native HR system for small businesses with 49 or fewer employees automated compliance plus access to a dedicated HR Business Partner. Invest on Wefunder: Download 7 free eBooks based on The Jason Cavness Experience: Join the Builders Club: Connect with Jason Cavness LinkedIn: https://www.linkedin.com/in/jasoncavness Instagram: TikTok: https://www.tiktok.com/@jasoncavness Podcast:
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Marketing, Mindset, and Modern Strategy with Nicholas White
12/05/2025
Marketing, Mindset, and Modern Strategy with Nicholas White
In this episode of The Jason Cavness Experience, Jason sits down with Nicholas White. A Seattle-based marketing strategist, startup advisor, entrepreneur, and operator with experience at Amazon, Microsoft, and multiple early-stage ventures. Nick has led digital marketing programs for major B2B/B2C brands, driven pipeline expansion, advised early-stage founders, and built systems that blend creativity, data, and practical execution. His approach to modern marketing is shaped by curiosity, experimentation, and a deep understanding of customer psychology. Jason and Nick dive into how marketing is evolving, what founders consistently get wrong, where AI fits into the modern toolkit, and how to align product, sales, and marketing around real customer needs. A sharp, value-packed episode for founders, marketers, and builders. Topics Discussed: • From Amazon/Microsoft to advising startups • What separates good marketing from great marketing • Curiosity as the foundation of strong strategy • Brand vs. demand why founders confuse the two • Building early-stage marketing teams • Using AI for content, research, and GTM • How to connect marketing execution to revenue • Creative psychology and differentiation • Leadership lessons across corporate + startup worlds • Budgeting, channels, and prioritization • Common hiring mistakes founders make • Nick’s advice for marketing leaders and founders Support CavnessHR Help Build the Future of HR CavnessHR is creating an AI-native HR system for small businesses with 49 or fewer employees automation plus a dedicated HR Business Partner. Invest on Wefunder: Download 7 free eBooks: Join the Builders Club: Connect with Nicholas White: Website: https://nicholasgwhite.net/ LinkedIn: Connect with Jason Cavness: LinkedIn: https://www.linkedin.com/in/jasoncavness Instagram: TikTok: https://www.tiktok.com/@jasoncavness Podcast:
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Inside the Founder Grind: HR Laws, Wefunder, Startups, and Building in Public — Jason Cavness Live
12/02/2025
Inside the Founder Grind: HR Laws, Wefunder, Startups, and Building in Public — Jason Cavness Live
In this solo episode of The Jason Cavness Experience, Jason goes live to break down everything he’s building across CavnessHR, the Wefunder campaign, HR law education, livestreaming strategy, and the behind-the-scenes founder grind people rarely talk about. Jason talks through his work on the HR Laws Livestream Deck, what small businesses keep getting wrong about HR compliance and why he’s pushing hard to create accessible education for founders who can’t afford expensive consultants. He also gives an update on the CavnessHR Wefunder campaign, the ebooks rollout, the Builders Club, and how he’s approaching daily content, livestreaming, and building in public to grow the platform. This livestream dives into HR automation, startup strategy, social media execution, bourbon rotation, livestream tech setups, Opus Pro clips, and the reality of pushing toward a world-class HR product for small businesses. If you want a real, unfiltered look at the life of a founder building multiple things at once this is it. Topics Discussed • The HR Laws livestream deck and why HR compliance needs to be simplified • How CavnessHR is rebuilding HR for small businesses • The Wefunder campaign update and what investors should know • The 7-ebook strategy and how it supports the Wefunder raise • The CavnessHR Builders Club and early supporter benefits • Daily livestreaming routines and camera setup improvements • Why creators should rotate bourbons on livestreams • How Jason uses Opus Pro for mass short-form video creation • Platform posting strategy: LinkedIn, TikTok, X, Instagram, YouTube • When to upload livestreams as podcast episodes • Why short (<30s) clips currently outperform 60–90s content • Responding to comment engagement and audience growth • How to run your own solo livestreams more effectively • The mindset required to build in public while fundraising Support CavnessHR Be Part of the Future of HR CavnessHR is creating an AI-native HR system for small businesses with 49 or fewer employees automation plus a dedicated HR Business Partner. 💸 Invest in CavnessHR on Wefunder: 📚 Download 7 free eBooks based on The Jason Cavness Experience: 🤝 Join the CavnessHR Builders Club:
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The Legend Behind 300+ Games: Culturalization, Creativity & Courage with Kate Edwards
11/28/2025
The Legend Behind 300+ Games: Culturalization, Creativity & Courage with Kate Edwards
In this episode of The Jason Cavness Experience, Jason sits down with Kate Edwards. An award-winning 30+ year leader in the global game industry, culturalization pioneer, former Executive Director of the IGDA, former head of the Global Game Jam, CEO of Geogrify, and CXO/Co-Founder of SetJetters. Kate has worked on more than 306 games across genres including RTS, FPS, racing, horror, and AAA franchises like Age of Empires, Battlefield, Mad Max, Jade Empire, and Indiana Jones. She is widely known for establishing the discipline of game culturalization, helping studios navigate geography, culture, geopolitics, and global markets. Jason and Kate dive deep into her journey from Microsoft geographer to global industry leader, her work on major titles, running IGDA during Gamergate, giving historic talks at the Royal Geographical Society, and consulting for studios around the world. Kate also opens up about battling imposter syndrome, embracing introversion as a superpower, protecting creative teams, and why the future of games depends on cultural awareness and authentic storytelling. A powerhouse episode for anyone in gaming, tech, leadership, or creative industries. Topics Discussed: • How Kate pioneered the field of game culturalization • Working on 300+ games across global studios • Her path from Microsoft to founding Geogrify • Cultural risks, geopolitical challenges, and narrative world-building • Behind the scenes of Age of Empires, Jade Empire, Battlefield, Indiana Jones, and more • The evolution of gaming from Pong to massive AAA franchises • Indie studios shaking up the industry • Speaking worldwide and navigating stage nerves • Gamergate, harassment, and standing up for underrepresented creators • Diversity, representation, and global game development • Her dream studios and game franchises • Why introversion can be a creative advantage • Imposter syndrome, leadership, and creative courage Connect with Kate Edwards: 🌐 Website: 🔗 LinkedIn: 🐦 X (Twitter): 📸 Instagram: Support CavnessHR Help Build the Future of Small Business HR CavnessHR is building an AI-native HR system for small businesses with 49 or fewer employees automation + a dedicated HR Business Partner 💸 Invest in CavnessHR on Wefunder: 📚 Download 7 Free eBooks from The Jason Cavness Experience: 🤝 Join the CavnessHR Builders Club:
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