21 Minutes With...
A weekly business podcast that sits down with founders, CEOs, creators, and industry leaders for focused, honest conversations. Instead of celebrating only wins, the show explores pivots, failures, and the moments they almost quit. It aims to reveal the unpolished blueprint behind building a brand, a business, or a creative career. Each episode runs about twenty-one minutes and features candid stories that rarely make the keynote.
Episodes
Building AI Companies One Dog at a Time (Episode 50 ft. Ed Buckley)
Most founders fall in love with a product and then go looking for a problem it solves. Ed Buckley has spent four companies doing the opposite.Buckley is the co-founder, chairman, and CEO of Scholar Education, the Tampa company using AI to personalize learning for students and teachers. Before that he built Peerfit into FitOn Health and launched Sword Intelligence inside Sword Health. Three of his
Question Everything (Episode 49 ft. Kevin Meyer)
Most of what looks like a tactical marketing problem is a diagnosis problem.Kevin Meyer is a brand and marketing strategist in Chicago who started out as an industrial designer at OtterBox. His way into the work was a question an intern asked in a design review that nobody in the room could answer: what did the customer say? He built a foam core mockup, spent a week talking to people in strip mall
A Global Perspective on Relationships (Episode 48 ft. Ludmila Woodruff)
Most high performers treat the relationship work as something to get to after the business is finally working. Ludmila Woodruff's argument is that the waiting is the problem.Ludmila is a relationship and emotional intelligence coach who works with founders, executives, and high achievers — women and men — on the patterns underneath the performance. Having lived across four countries and cultures,
The Oval Office Operator (Episode 47 ft. Lauren Wittenberg Weiner)
Most people treat rules as an endpoint. Lauren Wittenberg Weiner treats them as a starting point — and that distinction built a $100 million company.Lauren spent her early career inside the Office of Management and Budget at the White House, working daily against U.S. code and federal regulation. When she followed her husband on military orders to Italy, she was told military spouses weren't permi
The Tampa Tech Architect (Episode 46 ft. Tony DiBenedetto)
Most people talk about money as a motivator. Tony DiBenedetto talks about it as a mirror.Tony co-founded Tribridge in 1998 and spent nearly two decades building it into an 850-person technology firm before leading its sale to DXC Technology in 2017. He's now Chairman and CEO of Appspace, and Founder and Chair of Think Big for Kids, a national nonprofit that has helped more than 8,000 young people
How to Build a Real Estate Empire (Episode 45 ft. Ryan McGuinness)
The best opportunities often appear when everyone else is running in the opposite direction.Ryan McGuinness is the Founder of RPM Realty, a private lending and real estate investment company built on calculated risk, conservative valuations, and the ability to move quickly. His path started at 19, when he raised money to open a pizza restaurant across from the University of Florida, and continued
Building a business off of a bar napkin (Episode 44 ft. John Waldmann)
The hardest customer in software is usually the most underserved — and that's precisely the opportunity.John Waldmann is the Founder & CEO of Homebase, the team management platform now used by more than 150,000 small businesses. His path there ran through a teenage web design company called Angry Hippo, a tuxedo rental shop, BCG, and KKR — until two friends opened a restaurant and he saw first
The Gold Standard of Newscasting (Episode 43 ft. Stacie Schaible)
Most people assume that poise in front of a camera is something you're born with. Stacie Schaible's career is evidence that it's something you build — deliberately, and sometimes uncomfortably.Schaible is a 36-year broadcasting veteran, Murrow Award winner, and solo anchor of News Channel 8 at 6 in Tampa Bay. She's one of the most recognized faces in local news and someone who has spent decades st
The Expert of Medical Galmour (Episode 42 ft. Amanda Cuevas)
Most founder origin stories start with the big idea. Amanda Cuevas's starts with an honest admission in art school — and a sequence of pivots that didn't look like a plan until you see where they landed.Amanda is the founder and CEO of GlamNow, a concierge aesthetics platform operating in 15 states that brings licensed medical injectors directly to the client. She is a Tampa native who moved throu
An Island Girl's Journey to the Top (Episode 41 ft. Sheena Palacios)
Growth doesn't happen where you're comfortable — it happens at the exact edge where you're not sure you can pull it off. That's not a motivational line. For Sheena Palacios, it's an operating principle.Sheena is the founder of NIFT Business Solutions, a firm built around fixing the gap that PE-backed trade companies keep creating: implementing systems without training the people who actually use t
The Mission Guiding Veterans To A Better Life (Episode 40 ft. Elizabeth Kirkmeier)
This week, Brittany and Shayleen sit down with Elizabeth Kirchmeier, Director of Operations at SOF Missions, second-degree Brazilian Jiu-Jitsu black belt, former law enforcement officer, SANE advocate, gym owner, and CrossFit coach.Most people who dedicate themselves to service were first served by someone else. Elizabeth Kirchmeier wasn't — and that absence became the foundation for everything sh
Doordash's AI Marketing Wizard (Episode 39 ft. Hannah Davis Tsumoto)
This week on 21 Minutes With…, Brittany and Christian sit down with Hannah Davis Tsumoto, Head of AI Transformation at DoorDash.Hannah is responsible for integrating AI into marketing workflows across one of the most recognizable consumer brands in the world — and she's not talking about using ChatGPT for captions. She's talking about the fundamental rewiring of how marketing teams are built, how
Stepping Down & Building Up (Episode 38 ft. Samyr Qureshi)
This week, Brittany and Christian sit down with Samyr Qureshi, Co-Founder and former CEO of Knack, and Principal at The Bath & Racquet House, a first-of-its-kind private wellness and social club coming to Tampa.Samyr built Knack from a dorm room idea to a B2B edtech platform operating across hundreds of university campuses nationwide. He raised from one of the top pre-seed funds in the world,
The Architect Of Culinary Magic (Episode 37 ft. Melissa Santell)
This week on 21 Minutes With…, Brittany sits down with Melissa Santell — Founder & Food Photographer at FoodxFeels.Most food brands think they have a photography problem. What they actually have is a storytelling problem — and no amount of beautiful imagery fixes it if the strategy behind it is missing. Melissa has spent nine years working alongside Michelin star chefs and emerging restaurant
Redefining Women’s Soccer From Scratch (Episode 36 ft. Desiree Phelps)
Every game day looks effortless from the stands. That's not luck — that's operations.Desiree Phelps is the Director of Operational Strategy, Venues & Events for the Tampa Bay Sun Football Club, Tampa's newest professional women's soccer organization. She came up through minor league baseball, where wearing every hat wasn't optional. Now she's building a professional sports club from the ground
The Million Follower Attention Seeker (Episode 35 ft. Jony Lee)
Most content strategies are built around protecting the brand. Her strategy was built around volume — 10 TikToks a day, no approvals, and the freedom to fail publicly until something worked.Jony Lee is a content creator and former Head of Growth at Attention Seeker, the agency behind one of the most-watched organic brand accounts in her market. With 1.1 million TikTok followers and over 624K on In
MLB to Major League Business Owner (Episode 34 ft. Matt Joyce)
In this episode, Brittany and Christian sit down with Matt Joyce — a 14-season MLB veteran, All-Star, and hometown hero who spent six of those seasons with the Tampa Bay Rays. Today he's channeling that same competitive edge as an F45 Training owner and color commentator for FanDuel Sports Network.From the minor league grind to the bright lights of professional baseball, Matt built his career on g
The Beauty Queen Of HSN: Redefining Women’s Skincare (Episode 33 ft. Liz Folce)
In this episode, Brittany sits down with Liz Folce, Founder & CEO of Nakery Beauty and the Beauty Queen of HSN, a woman who has spent over 35 years in the beauty industry doing something most brands never bother to do — actually listening.From behind the Estée Lauder counter to sold-out collections on HSN, Liz built her entire career around genuine relationships with women. Not focus groups fo
The World's GREATEST Traveler (Episode 32 ft. Bryan Lewis)
In this episode, Brittany and Christian sit down with Bryan Lewis, Founder of Tenon Tours and CEO of Lemon Rock Motorcycle Tours, a man who has spent 25 years turning travel into something people actually feel.From spring break chaos to curated luxury across 19 European destinations, Bryan has built a career around one simple belief: that the best travel experiences aren't just planned, they're fe
The Man Giving Streaming A BIG Boost (Episode 31 ft. Ronnie Eith)
Welcome back to 21 Minutes With… the entrepreneur turning streaming into real opportunity.This week, Brittany and Jackie sit down with Ronnie Eith, Founder & CEO of Boost TV, to unpack what it actually looks like to walk away from comfort—and build something that lasts.Before Boost TV, Ronnie’s path looked textbook successful. A standout college football player turned executive, he spent over
The Business Behind Global Wine Culture (Episode 30 ft. Dupre Nell)
Welcome back to 21 Minutes With… a global wine leader carrying 300 years of heritage into the modern market.This week, Brittany and Christian sat down with Dupre Nell of Anthonij Rupert Wynes, a historic estate rooted in the Franschhoek Valley of South Africa just outside Cape Town.Before joining Anthonij Rupert, Dupre built his career working with some of South Africa’s most respected wine brands
The Artist Painting Over Florida's Canvas (Episode 29 ft. Bianca Burrows)
Welcome back to 21 Minutes With… the mixed media artist leaving her mark on the world's canvas.This week, Brittany sat down with Bianca Burrows, a Tampa-based mixed media artist and founder of BB Art, to talk about building a creative career rooted in expression, collaboration, and staying true to your craft.After earning her Bachelor of Fine Arts from the University of Tampa, Bianca turned her pa
The Marketing Mother Of What You Drink (Episode 28 ft. Taylor Prater)
Welcome back to 21 Minutes With… the marketing mind behind mission-driven beverage brands focused on people, planet, and products that actually make you feel good.This week, Brittany and Jackie sat down with Taylor Prater, the Mother of Marketing behind Mother Kombucha and co-founder of Made Coffee, to unpack what it really takes to build brands that people trust, love, and advocate for.Taylor has
A Fresh Take on the Classic Bagel Run (Episode 26 ft. Jeff Perera)
Welcome back to 21 Minutes With… the man who turned a home kitchen experiment into a bagel brand people line up for.This week, Brittany sat down with Jeff Perera, Co-founder of Jeff’s Bagel Run, to break down how a layoff, a craving for better bagels, and a whole lot of trial and error sparked one of Florida’s fastest-growing bagel spots.From his early beginnings baking bagels at home to opening 2
The Business Behind 3 Minute Pizza (Episode 25 ft. Kevin Moran)
Welcome back to 21 Minutes With… the leader helping Blaze Pizza scale at a three-minute pace.This week, Brittany and Shea sit down with Kevin Moran, Chief Development Officer at Blaze Pizza, to break down what it really takes to build a fast casual brand that moves fast without breaking. From a three-minute pizza model to LeBron James investing in the company, Kevin unpacks the formula behind Blaz
The Cloud Company Of The FUTURE (Episode 24 ft. Jacob Halusic)
Welcome back to 21 Minutes With… the founder building a modern cloud company by putting people and culture first.This week, Brittany and Christian sit down with Jacob Halusic, founder and CEO of Trofeo, to talk about how his career across startups, exits, and private equity shaped the way he is building his next chapter in tech.From early sales roles and entrepreneurial pivots to launching Trofeo
The Pitfalls of Holiday Branding (Episode 23 Holiday Special)
Welcome back to 21 Minutes With… the 21A: Holiday Edition!This week, we unpack what brands consistently miss during the most emotional season of the year. From tone-deaf campaigns and overcomplicated promotions to the difference between discounts and storytelling, the conversation pulls back the curtain on why so many holiday efforts feel empty and what consumers actually want to see.We dive into
Legacy Coaching That Sustains Generational Wealth (Episode 22 ft. Vera Anderson)
Welcome back to 21 Minutes With… the legacy consultant thats redefining what it means to build wealth that actually lasts generations.This week, Brittany and Walter sat down with Vera Anderson, founder of Global Elements Consulting and Chair at Tiger 21, to talk about the intersection of health, wealth, leadership, and legacy. In this episode, She explains to us why success without alignment event
Shot Down SHARK TANK, But Made MILLIONS In Junk (Episode 21 ft. Omar Soliman)
Welcome back to 21 Minutes With… the Co-founder who turned hauling junk into a nationally recognized brand, College Hunks Hauling Junk & Moving.This week, Brittany and Christian sat down with Omar Soliman to break down how he helped transform a college side hustle into a franchise built on culture, personality, and a brand name no one forgets. He shares the wild early days of saying yes to eve
The Bright Ideas Behind Yellow The Label (Episode 20 ft. MaryKatherine Black)
Welcome back to 21 Minutes With… the cofounder behind one of the fastest rising fashion brands, Yellow the Label.This week, Brittany, Shea, and Shayleen sat down with MaryKatherine Black to break down how she built a standout label without a fashion degree, why she designs for women across seasons and stages of life, and how she keeps Yellow The Label fresh in a market that burns through trends ov
Giving the Lingerie Industry a REALITY CHECK at Wherewithal (Episode 19 ft. Danielle Rushton)
Welcome back to 21 Minutes With… the woman rethinking everything we’ve been told to tolerate about bras, why the industry stayed stuck for almost a century, and how one founder decided enough was enough.This week, Brittany, Shea, and Shayleen sat down with Danielle Rushton, CEO and Designer of Wherewithal, to unpack how she built one of the most innovative solutions the lingerie industry has seen
Why Grown-Ups Need Better BFFs (Episode 18 ft. Danielle Bayard Jackson)
Welcome back to 21 Minutes With… (this time with adult friendships, professional boundaries, and one expert showing why grown-ups need better BFFs).This week, Brittany and Shea sat down with Danielle Bayard Jackson, director of the Women’s Relational Health Institute, founder of TELL Public Relations, and author of Fighting for Our Friendships, to talk about why the relationships we build outside
The Secret Behind Sarasota’s Most Beloved Beer Bar (Episode 17 ft. Mark Tuchman)
Welcome back to 21 Minutes With… (this time with craft beer, community building, and the Sarasota spot redefining what a neighborhood bar can be).This week, Brittany, Christian, and Shea sat down with Mark Tuchman, owner of 99 Bottles in Sarasota, to talk about creating connection one pour at a time. From the “Blockbuster effect” of remembering every guest’s name to designing a beer bar that feels
Beyond the Case File: Unlocking Real Trust (Episode 16 ft. Marcus Fernandez)
Welcome back to 21 Minutes With… (this time with trust, client care, and the human side of personal injury law).This week, Brittany and Cindy Haynes, from EraserFarm, sit down with Marcus Fernandez, Attorney at Kinney, Fernandez & Boire, P.A., and second-generation law firm owner, to talk about how trust, transparency, and empathy set his firm apart in a crowded market. From building authentic
The Scariest Marketing Campaigns of 2025 (Episode 15. Halloween Special)
Welcome back to 21 Minutes With… a special Halloween episode (this time with haunted rebrands, marketing jump scares, and a few creative nightmares that should’ve stayed in the drafts).This week, we’re diving into the most terrifying marketing stunts of the year, the ones that made us laugh, cringe, and maybe question a few creative briefs along the way. From campaigns that completely lost the plo
How Scholar Education Balances Tech, Trust, and Teaching (Episode 14 ft. Marlee Strawn)
Welcome back to 21 Minutes With… (this time with classroom innovation, AI-powered learning, and a couple of dogs who might just change the future of education).This week, Brittany and Christian sat down with Marlee Strawn, Co-Founder of Scholar Education, to talk about how AI, transparency, and trust are shaping the next generation of learning. From teacher empowerment to student engagement, Marle
How To Turn ANY Brand Into A Household Name (Episode 13 ft. Kevin Keith)
Welcome back to 21 Minutes With… (this time with brand reinvention, operational magic, and a few hot takes on what it really takes to make a brand people actually love).This week, Brittany and Cindy sat down with Kevin Keith, the marketing maestro behind brands like Edible Arrangements, Orange Theory Fitness, Coca-Cola, and UPS. He’s the strategist, the storyteller, and the conductor behind some o
Hitting A Digital Grand Slam With Fanatics Betting & Gaming (Episode 12 ft. Nicole Sia)
Welcome back to 21 Minutes With… (this time with algorithms, creativity, and a few hot takes on what it really means to build a brand people actually care about).This week, Brittany and Shea sat down with Nicole Sia, the marketing powerhouse behind brands like DoorDash, Spotify, and Fanatics Betting & Gaming. She’s the face, the voice, and the strategy behind some of the most recognizable soci
From Private Equity to Sweat Equity, Building From the Ground Up (Episode 11 ft. Frank Fiume)
Welcome back to 21 Minutes With… (this time with playbooks, passion, and a few reality checks for every founder).This week, Brittany and Shea sat down with Frank Fiume, founder of i9 Sports and Emerging Franchise Brands, the man who didn’t just build a franchise but pioneered an entire category. From bootstrapping local youth leagues into one of the largest sports franchises in America to mentorin
The Guy Behind Over 6 Billion Email Sends A YEAR (Episode 10 ft. Jay Schwedelson)
Welcome back to 21 Minutes With… (this time with emails, AI hacks, and a few typos that actually work).This week, Brittany and Christian sat down with Jay Schwedelson, founder of subjectline.com and host of the #1 Marketing Podcast in the US, Do This NOT That: Marketing Tips with Jay Schwedelson, whose strategies power over six billion email sends annually. From clever subject line experiments to
The Men Who’ve Tasted Over 1 Million Wines (Episode 9 ft. Stephan De Beer & Jerry Stephan)
Welcome back to 21 Minutes With… (this time with bubbles, South African sunshine, and a saber or two).This week, Brittany and Christian sat down with Stephan de Beer, head winemaker of Krone Vintage-only Cap Classique, whose craft has been poured into more than 2 million bottles a year. Alongside CEO of Ascent Wines Jerry Stephan, we uncorked a conversation about tradition, risk, and why sometimes
Lightning Sellouts, Golf Booms, Retail Reboots (Episode 8 ft. Matt Corey)
Welcome back to 21 Minutes (this time with Stanley Cups, golf rivalries, and marketing plot twists).This week, we sat down with Matt Corey, the marketing mind who’s left his fingerprints on some of the biggest names in sports and retail. From the Tampa Bay Lightning, and their post-Stanley Cup fan boom, to the PGA Tour, during golf’s most volatile era, to the LPGA, USTA, and even retail powerhouse
The Driver Behind Sarasota Ford’s Boldest Moves (Episode 7 ft. Elesia Vera)
Welcome back to the chaos (this time it comes with dance battles, dealership dads, and a whole lot of Fergalicious).In this episode we sit down with Elesia Vera, the social media manager behind Sarasota Ford, the dealership that decided car buying should actually be fun. Instead of stiff sales pitches and awkward handshakes, they are building a community on TikTok and Instagram where customers sho
The Growth Guy Behind Booze, Burgers, and Breadmakers (Episode 6 ft. Terry Haley)
Welcome back to the chaos (this time, it’s served with a side of burgers, beer, and big ideas). In this episode we sit down with Terry Haley, a seasoned growth leader who has worn just about every executive hat in the business world.He has been a Chief Commercial Officer (CCO), Chief Growth Officer (CGO), Global Chief Marketing and Experience Officer, and Chief Marketing Officer (CMO) for some of
The 1st US Producer of Ouzo (Episode 5 ft. Barry & Lisa Butler)
Welcome back to the chaos (this time, it is barrel-aged and slightly buzzed). In this episode, we sit down with Barry and Lisa Butler from Tarpon Springs Distillery, and Cindy Haynes from Eraser Farm. This Florida craft distillery is known for bold innovation, award-winning spirits, and has magically transformed a historic sponge warehouse into a hub for cocktail culture and live music.Our convers
Liquid Death’s Chaos Conductor (Episode 4 ft. Andy Pearson)
Welcome back to the chaos (this time, it’s carbonated). In this episode, we dive into Liquid Death, the brand that transformed canned water marketing into a cultural phenomenon through bold brand voice, viral stunts, and rule-breaking creativity.From wild creative pitches that never left the whiteboard to the art of knowing when to ignore marketing “best practices”, we unpack what it takes to lead
The Airport That Broke The Internet (Episode 3 ft. Ashley Iaccarino)
Welcome back to the chaos (the airport kind). In this episode, we’re diving headfirst into the bold, brilliant, and slightly unhinged world of the Tampa International Airport brand account, the unexpected social media powerhouse creating some of the funniest airport content on the internet.From weird DMs (not what you’d expect) to viral emoji posts that made national headlines, we explore how a on
Brands That Behave So Badly, It's Brilliant - Episode 2
Welcome back to the chaos (the marketing kind). In this episode, we’re breaking down the badly brilliant brands, the ones that feel unhinged, chaotic, even borderline rude… and yet? Totally iconic.From Ryanair trolling its own customers to Pine-Sol claiming it "smells like dominance," we’re unpacking why these wild strategies actually work. Think: owned truth, no pretense, full personality possess
21 Minutes With... The 21st Agency - Episode 1
Welcome to the chaos (but like, the fun kind). In this first episode of 21 Minutes With..., we’re pulling back the curtain on who we are, what we’re about, and the oddly specific things that drive us absolutely insane (all in just 21 minutes). From hot takes to our most irrational pet peeves, it’s all on the table.Stay tuned for special guests, strong opinions, and weekly chaos from the five of us
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