Headsmack: Conversations with Misfits

Hosted by Paul Povolni

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Jul 2026

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About the show

The Headsmack Podcast with host Paul Povolni invites you to listen in on conversations with misfits, mavericks and trailblazers. Join us as we explore the life of difference-makers and those who have stumbled, fumbled and then soared. Be inspired as they candidly share their journeys and the aha moments that changed everything.

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July 26, 2026Episode 9856 min

Jonathan Montoya / Owner of Maker AI. Affiliate Expert

Jonathan Montoya had negative $1,200 in his bank account and a full-time engineering job he hated. Six years later he has built three separate businesses to seven figures and taught over 65,000 students how to build a life outside the 9-to-5. In this episode he breaks down the exact YouTube-as-a-hub strategy that took him from broke to burnt out to free, the Facebook "comment ladder" trick that is quietly generating him millions of views right now, and how he used AI tools like Claude Code and Lovable to go from idea to a thousand paying software customers in under six weeks. If you have ever wondered whether you can actually build a business by learning in public, this conversation is your proof. BIO: Jonathan Montoya is a digital marketing entrepreneur, affiliate marketing educator, and AI software builder who has taken three different businesses to seven figures. After earning an electrical engineering degree from the University of New Mexico and spending years in a corporate engineering role he never loved, Montoya began posting a YouTube video every single day at 3:30 a.m. while his bank account sat at negative $1,200. Nine months later, in March 2020, he quit his job to pursue affiliate marketing and content creation full time. He has since built a following of hundreds of thousands across YouTube, TikTok, Instagram, and Facebook, ranked among the top affiliates worldwide for launches including Alex Hormozi's $105 million offer and Russell Brunson's Offer Lab, and served more than 66,000 students through his digital marketing and AI programs. He is the creator of Freedom Threads, a Facebook growth automation tool, and Maker AI, a platform built in partnership with WebinarKit founder Stefan Ciancio that helps entrepreneurs find, build, and market their own AI-powered software. LINKS: https://freedomthreads.ai/ https://getmakerai.com/ Send us Fan Mail Paul Povolni (Voppa) is the founder of Voppa Creative and a creative leader with over 30 years of experience in brand strategy and design. Based in Jackson, Mississippi, he has worked with clients internationally, leading teams in award-winning branding while serving as a coach and speaker. Paul delivers workshops and keynotes on brand strategy, creative thinking, and organizational culture, and hosts The Headsmack Podcast: Conversations with Misfits. His work centers on helping organizations lead with Clarity, Creativity, and Culture. Headsmack Website Voppa Creative Website

May 31, 2026Episode 9754 min

Ramon Ray / Founder, ZoneofGenius.com. Speaker. Author. Host

Most entrepreneurs think hustle is the answer. Ramon Ray has a different take. The man who started 5 companies, sold 3, hosted over 200 episodes of a USA Today Network show, and interviewed all 5 Shark Tank sharks and President Obama says the real game is relationships, resilience, and rewriting the soundtrack in your head. In this conversation, Ramon and Paul go deep on what it actually takes to build a business that lasts, how failure works as a clarity tool, why desperation is the fastest way to kill a deal, and what the alter ego effect can do for entrepreneurs who feel stuck. This is not a highlight reel. This is the real middle of the journey. BIO: Ramon Ray is a five-time entrepreneur who has started and sold three companies, and he shows no signs of slowing down. He is the publisher of ZoneofGenius.com and the author of five books, including "The Celebrity CEO," which lays out how entrepreneurs can build and leverage their personal brands for lasting growth. Ramon has served as an expert witness to the United States Congress and was invited by the Office of the President to speak at the White House, where he also conducted the historic first presidential live Google Hangout interview with President Obama. As a global keynote speaker and event host, he has shared the stage with Deepak Chopra, Simon Sinek, Seth Godin, and Gary Vaynerchuk, and has interviewed all five original Shark Tank investors. Known for his infectious energy and deeply human approach to business, Ramon's mission is to help entrepreneurs build not just successful businesses but joyful lives. His brand ambassador work with companies including Bitdefender and his twice-weekly email newsletter through Zone of Genius reach thousands of small business owners around the world. Ramon's newest resource is dailymojo.com, a free daily inspiration app he built to keep entrepreneurs encouraged and moving forward. LINK: DailyMojo.com ZoneofGenius.com Send us Fan Mail Paul Povolni (Voppa) is the founder of Voppa Creative and a creative leader with over 30 years of experience in brand strategy and design. Based in Jackson, Mississippi, he has worked with clients internationally, leading teams in award-winning branding while serving as a coach and speaker. Paul delivers workshops and keynotes on brand strategy, creative thinking, and organizational culture, and hosts The Headsmack Podcast: Conversations with Misfits. His work centers on helping organizations lead with Clarity, Creativity, and Culture. Headsmack Website Voppa Creative Website

May 25, 2026Episode 961 hr 4 min

Vinnie Fisher / Founder & CEO, SiteTrust. Coach. Speaker. Author

The Trust Gap: What AI Is About to Expose About Your Business Vinnie Fisher has done something most entrepreneurs only dream about: he built and exited three seven to eight figure companies, and now he is using everything he learned to tackle one of the most urgent problems in modern business, the AI trust crisis. A corporate attorney for 26 years, a serial entrepreneur, and the author of four books, Vinnie is the founder and CEO of SiteTrust, the certification platform that helps businesses prove to their customers that they use AI responsibly. In this candid conversation with Paul Povolni, Vinnie shares the chip-on-his-shoulder origin story that drove him from a broken home to the top of his law school class. He breaks down what makes a business truly sellable, why the converting offer is the single most important thing in any company, and how he found the idea for SiteTrust in the middle of a church sermon. Vinnie also introduces the Trust Gap framework, covering the three leadership gaps every business leader needs to shrink, integrity, awareness, and courage. And he closes with a message that might just be the most practical thing any entrepreneur can hear: your real superpower is not quitting. GUEST BIO: Vinnie Fisher is a serial entrepreneur and problem-solver who has spent three decades identifying critical market gaps and building scalable infrastructure to solve them, from 26 years in corporate law to founding and exiting multiple seven to eight figure companies generating over $400 million in sales. A lawyer by trade, Vinnie practiced tax and business law for 10 years before leaving the field in 2007 to pursue entrepreneurship full-time, building companies across industries including early internet, web hosting, and back-office financial operations. He is now the founder and CEO of SiteTrust, the certification standard for AI disclosure that helps businesses demonstrate transparency, reduce legal exposure, and earn measurable customer trust. Vinnie is the author of four published books, including "The CEO's Mindset," "False Profits," and "Beyond Your Shadow," and is currently writing his fifth book, "The Trust Gap." He lives in Ohio with his wife Deb and their four children. LINKS: sitetrust.com/gifts Send us Fan Mail Paul Povolni (Voppa) is the founder of Voppa Creative and a creative leader with over 30 years of experience in brand strategy and design. Based in Jackson, Mississippi, he has worked with clients internationally, leading teams in award-winning branding while serving as a coach and speaker. Paul delivers workshops and keynotes on brand strategy, creative thinking, and organizational culture, and hosts The Headsmack Podcast: Conversations with Misfits. His work centers on helping organizations lead with Clarity, Creativity, and Culture. Headsmack Website Voppa Creative Website

May 18, 2026Episode 951 hr 1 min

Lisa Cole / Chief Marketing, Product & AI Officer. Author. Speaker

Your buyers already have a preferred vendor before a sales rep calls. 90% of B2B companies pick their number one choice before any sales conversation ever happens. And 85% of those deals go to whoever holds that top spot. Four-time CMO Lisa Cole has a framework for making sure that vendor is you. She calls it Content, Community, and Credibility. It works whether you are a solo founder or leading a global marketing team. She also breaks down why the headcount-first model is quietly draining your pipeline. And what the marketing organization of the future actually looks like. Hint: it is a small SWAT team of strategic orchestrators, not a bloated department. Guest Bio: Lisa Cole is a four-time CMO and the Chief Product, Marketing & AI Officer at 2X, a leading B2B Marketing-as-a-Service firm where she drives growth through innovative strategies and operational efficiency. With over 25 years of expertise in B2B technology and professional services, she has transformed marketing organizations into scalable, profitable growth engines at companies including Huron, FARO Technologies, and Cellebrite. Lisa is the only two-time recipient of Forrester's prestigious Return on Integration Award, earning the distinction in both 2018 and 2022, and her leadership has earned additional recognition from the CMO Alliance and DemandGen Report for her expertise in turning marketing from a cost center into a revenue driver. She is the author of three books, "The Revenue RAMP," "Brand Gravity," and "The Limitless CMO," which equips marketers with actionable blueprints for modern, buyer-centric growth in the age of AI. Lisa is passionate about mentoring emerging marketers and advancing women in leadership. She lives in Michigan with her family and can be reached at lisacole.ai or on LinkedIn as LisaCole01. LINK: LisaCole.ai Send us Fan Mail Paul Povolni (Voppa) is the founder of Voppa Creative and a creative leader with over 30 years of experience in brand strategy and design. Based in Jackson, Mississippi, he has worked with clients internationally, leading teams in award-winning branding while serving as a coach and speaker. Paul delivers workshops and keynotes on brand strategy, creative thinking, and organizational culture, and hosts The Headsmack Podcast: Conversations with Misfits. His work centers on helping organizations lead with Clarity, Creativity, and Culture. Headsmack Website Voppa Creative Website

May 9, 2026Episode 9452 min

Dr. William Attaway / CEO-Appreciation at Work. Leadership Coach. Author. Speaker

The Five Languages Most Leaders Never Learned Dr. William Attaway didn't set out to become one of the country's most sought-after leadership coaches. He started as a stock guy at a drugstore, dropped out of college twice, watched a telecom giant disappear inside five years, and learned the hard way that leading people is nothing like running a process. In this episode, William sits down with Paul Povolni to share the moments that shaped his philosophy, the productivity system he's used for 20 years, and the surprising data behind why most workplace recognition programs fall flat. As CEO of Appreciation at Work, the company behind the bestselling Five Languages of Appreciation in the Workplace, William reveals how a small shift in how leaders communicate value can drive a 22 percent productivity lift without adding a single new hire. If you've ever lost a key team member and wondered what really happened, this conversation will reframe everything. GUEST BIO: Dr. William Attaway is the CEO of Appreciation at Work and an executive coach with more than 30 years of experience leading teams and developing leaders. He is the host of the Catalytic Leadership Podcast, ranked in the top 1.5 percent of shows globally, where he sits down with high-performing entrepreneurs, agency owners, and catalytic leaders from around the world. Originally from Birmingham, Alabama and now based in northern Virginia, William holds a PhD in archaeology and biblical backgrounds, which has taken him on multiple seasons of digs in Jordan. He is the author of Catalytic Leadership: 12 Keys to Becoming an Intentional Leader Who Makes a Difference, and he leads the company behind the bestselling Five Languages of Appreciation in the Workplace, co-authored by Dr. Paul White and Dr. Gary Chapman. A leader devoted to his faith and his family, William has been married to his wife Charlotte for 28 years, and they have two exceptional young adult daughters. Link : joinaaw.com Send us Fan Mail Paul Povolni (Voppa) is the founder of Voppa Creative and a creative leader with over 30 years of experience in brand strategy and design. Based in Jackson, Mississippi, he has worked with clients internationally, leading teams in award-winning branding while serving as a coach and speaker. Paul delivers workshops and keynotes on brand strategy, creative thinking, and organizational culture, and hosts The Headsmack Podcast: Conversations with Misfits. His work centers on helping organizations lead with Clarity, Creativity, and Culture. Headsmack Website Voppa Creative Website

May 3, 2026Episode 931 hr 3 min

Why 95% of YouTube Channels Are Failing (And the 3 Things That Will Fix It) | Scott Simson

Scott Simson is a YouTube strategist, entrepreneur, and founder of Raffiti Media who has spent the better part of a decade cracking the code on what makes content get clicked, watched, and converted into real business results. In this episode, Scott shares his full origin story, from seven failed businesses and near-financial collapse to co-authoring a bestselling children's book, building a family YouTube channel to hundreds of thousands of subscribers, and eventually walking away from that channel when the algorithm began rewarding manufactured drama he was not willing to fake. He breaks down his Tension Trinity framework, explains the critical difference between search-based and recommended titles, reveals how he uses Claude to produce seven short-form videos per day with the CHEAT method, and gives business owners a clear step-by-step approach for building a YouTube channel that generates qualified leads. This is one of the most practical and honest YouTube strategy conversations available anywhere. GUEST BIO: Scott Simson is the founder and CEO of Raffiti Media, a full-service YouTube management and consulting agency based in the Dallas, Texas area that has generated billions of organic views for business clients across the entrepreneur and small business space. Before launching the agency in 2019, Scott and his wife Camber built a successful family YouTube channel that reached hundreds of thousands of subscribers, an achievement they walked away from when the algorithm began incentivizing manufactured drama they were not willing to create. That integrity-driven decision became the foundation for Raffiti's entire philosophy. Scott is also the co-author of "Fox and the Mountain," a bestselling allegorical book on success principles published in both a children's edition and an adult and teen version, and has been featured by vidIQ and other major voices in the creator economy. His work with Raffiti Media focuses on helping small businesses and entrepreneurs use consistent, educational YouTube content to grow brand awareness, generate qualified leads, and build lasting audience trust without paid advertising. LINK: Www.Scottsgpts.com Send us Fan Mail Paul Povolni (Voppa) is the founder of Voppa Creative and a creative leader with over 30 years of experience in brand strategy and design. Based in Jackson, Mississippi, he has worked with clients internationally, leading teams in award-winning branding while serving as a coach and speaker. Paul delivers workshops and keynotes on brand strategy, creative thinking, and organizational culture, and hosts The Headsmack Podcast: Conversations with Misfits. His work centers on helping organizations lead with Clarity, Creativity, and Culture. Headsmack Website Voppa Creative Website

April 19, 2026Episode 921 hr 11 min

Molly Mahoney / Ai Queen. Founder and CEO of The Prepared Performer

Molly Mahoney went from performing on stages in New York, Las Vegas, and the national tour of Chitty Chitty Bang Bang to building a seven-figure digital marketing empire, and she did it by doubling down on the one thing most entrepreneurs try to hide: their weird. In this episode of the Headsmack Podcast, Molly breaks down how she launched the world's first AI-focused content membership in 2021, what it really means to dance with the AI instead of just accepting its first output, and the exact frameworks she uses to help entrepreneurs build sticky, standout brands in a world full of AI zombies. She walks through her SAAVE system for identifying your uniquely awesome qualities, her Spotlight Effect for brand differentiation, and the powerful reminder that the best marketing tool available today is still just a conversation with a real human being. Whether you are just getting started with AI or you have been in the game for years, this episode delivers the strategy and the mindset to help you show up more powerfully and profit from exactly who you are. GUEST BIO: Molly Mahoney is a digital marketing strategist, keynote speaker, and former NYC performer who has spent over a decade helping entrepreneurs blend AI-powered marketing with authentic human connection. After training at the Music Room School of Performing Arts from age eight, she performed on cruise ships, in Las Vegas, and on the national tour of Chitty Chitty Bang Bang, including a memorable on-set day with Dick Van Dyke. She launched The Prepared Performer in 2013, initially as a vocal coaching business, and evolved it into a seven-figure digital marketing enterprise built entirely on organic content. Her videos have accumulated over 39 million views, her work has been featured in Forbes, Inc., and Entrepreneur, and in 2021 she launched the world's first AI-focused content membership, a full two years before ChatGPT brought artificial intelligence to the mainstream conversation. She is the author of Choose Confidence, Finding My Awesome, and the AI playbook Ai-ify Your Business, and is currently co-producing the Broadway musical adaptation of Beaches. She also runs the AI Stars membership and Prepared Performer coaching programs at mollymahoney.com, and stands by the belief that the more fun you have, the more money you make. LINKS: Special Listener link for Her Ideal Client Avatar: molly.live/headmsack mollymahoney.com Send us Fan Mail Paul Povolni (Voppa) is the founder of Voppa Creative and a creative leader with over 30 years of experience in brand strategy and design. Based in Jackson, Mississippi, he has worked with clients internationally, leading teams in award-winning branding while serving as a coach and speaker. Paul delivers workshops and keynotes on brand strategy, creative thinking, and organizational culture, and hosts The Headsmack Podcast: Conversations with Misfits. His work centers on helping organizations lead with Clarity, Creativity, and Culture. Headsmack Website Voppa Creative Website

April 14, 2026Episode 911 hr 10 min

David Brier / The Brand Father. Chief Gravity Defyer. Slayer of the Mundane

Most companies are not bad at marketing. They are bad at branding — and they do not even know the difference. David Brier has been the guy CEOs call when the budget is gone, the message is blurry, and the brand is invisible. He has helped businesses generate over $9 billion in growth by fixing the one thing most consultants skip. He defines branding in exactly four words. He wrote a book with a 36-point font — intentionally — because no one should need glasses to get a great idea. Daymond John wrote the foreword. In this episode, David breaks down why branding comes before marketing, why surprise is the secret weapon most brands ignore, and why the same brand solution produces completely different results depending on the culture of the company receiving it. If your brand is blending in, this conversation is the intervention you did not know you needed. Link: https://www.risingabovethenoise.com/ Send us Fan Mail Paul Povolni (Voppa) is the founder of Voppa Creative and a creative leader with over 30 years of experience in brand strategy and design. Based in Jackson, Mississippi, he has worked with clients internationally, leading teams in award-winning branding while serving as a coach and speaker. Paul delivers workshops and keynotes on brand strategy, creative thinking, and organizational culture, and hosts The Headsmack Podcast: Conversations with Misfits. His work centers on helping organizations lead with Clarity, Creativity, and Culture. Headsmack Website Voppa Creative Website

April 7, 2026Episode 901 hr 2 min

Karen Hite / Co-Founder Hite International. Scale with Stability

Karen Hite knows what it looks like to win on paper and fall apart on the inside. As the COO of Committed Mastermind and co-founder of Hite Digital — a three-time Inc. 5000-ranked digital marketing agency she built alongside her husband from their home in Nicaragua — Karen has lived the full spectrum of the entrepreneurial journey. She has experienced the thrill of explosive growth, scaling to 27 franchise locations in under two years, and the crushing weight of the anxiety, depression, and personal disconnection that came with it. Now Karen is on a mission to help business owners do it differently. Through Committed Mastermind , events like Scale with Stability and The Commitment Summit , and a newly developed framework rooted in purpose, Karen equips entrepreneurs to grow their businesses without destroying the things that matter most. In this conversation with host Paul Povolni, Karen shares her origin story from Nicaragua to the US, walks through the four pillars of her Scale with Stability framework, challenges the hustle culture mentality, and opens up about one of the most important — and most neglected — questions in business: What is your gift, and are you actually using it? Links: http://scalewithstability.com/summit Gift: http://gifts.scalewithstability.com/ Send us Fan Mail Paul Povolni (Voppa) is the founder of Voppa Creative and a creative leader with over 30 years of experience in brand strategy and design. Based in Jackson, Mississippi, he has worked with clients internationally, leading teams in award-winning branding while serving as a coach and speaker. Paul delivers workshops and keynotes on brand strategy, creative thinking, and organizational culture, and hosts The Headsmack Podcast: Conversations with Misfits. His work centers on helping organizations lead with Clarity, Creativity, and Culture. Headsmack Website Voppa Creative Website

March 30, 2026Episode 891 hr 23 min

Andy Starr / Co-Founder Level C. Brand Architect. Strategy Sparring Partner. TEDx Speaker

Andy Starr is one of the rare minds operating at the true intersection of strategy, creativity, and business design — and he is not interested in the surface-level version of any of them. As co-founder and managing partner of Level C, the world's most visionary branding education program, Andy built something genuinely unusual: a school for how to think, created alongside iconic brand author and strategist Marty Neumeier. In this episode, Andy shares his unconventional origin story — musician, literature student, finance professional, recovering law student — and how a single book handed to him by the right person at the right moment changed the entire trajectory of his career. He breaks down why brand strategy has become dangerously commoditized, why AI is a tool built for averages in a discipline that demands advantage, and why the practitioners who will win in the years ahead are the ones developing taste, judgment, and the courage to think non-linearly. This is a bold, unfiltered conversation about what it really takes to do this work at the highest level. GUEST BIO: Andy Starr is co-founder and managing partner of Level C, a school of masterclasses and critiques in brand and business design that he built alongside international brand expert and author Marty Neumeier. His path to that role is anything but conventional: a trained musician who studied English Literature as an undergraduate, Andy worked in finance and studied law before entering the world of brand — and the detour through each of those disciplines sharpened the cross-trained thinking that now defines his approach. Born in Philadelphia and currently living in Vienna, Austria, Andy is also a top-1% TEDx speaker, an MBA professor at a European university, a co-founder of an LA-based public safety tech company, and a self-described C-suite sparring partner for select clients. He describes himself as a "provocateur-for-hire" at the intersection of education, business, and brand — helping clients outmaneuver competition and conditions in their markets and make their marketing, advertising, and PR work better, land stronger, and drive real results. Through Level C's progressive series of masterclasses, Andy and Marty are training a new generation of strategic thinkers — people who know not just what brand is, but how to actually use it. LINK: Level C Send us Fan Mail Paul Povolni (Voppa) is the founder of Voppa Creative and a creative leader with over 30 years of experience in brand strategy and design. Based in Jackson, Mississippi, he has worked with clients internationally, leading teams in award-winning branding while serving as a coach and speaker. Paul delivers workshops and keynotes on brand strategy, creative thinking, and organizational culture, and hosts The Headsmack Podcast: Conversations with Misfits. His work centers on helping organizations lead with Clarity, Creativity, and Culture. Headsmack Website Voppa Creative Website