21 Minutes With...

The 21st Agency

There's no shortage of business podcasts. There is, however, a shortage of those who ask the question you’re really thinking.

"21 Minutes With…" is our answer to that.

Every week, we sit down with founders, CEOs, creators, and industry leaders for one focused conversation, not about their wins, but about the whole picture. The pivots. The failures that turned out to be the whole lesson. The moment they almost quit, and why they didn't.

We're asking the questions no one else is asking and telling the stories that don't usually make the keynote. It’s a confession booth, with better lighting.

Because the real blueprint for building a brand, a business, or a creative career isn't in the polished case study. It's in the honest conversation most people never have out loud.

That's what we're creating. Twenty-one minutes at a time.

New episodes drop every week, hosted by the team at The 21st Agency.

Follow along and subscribe wherever you listen to podcasts.

“21 Minutes With…“ because the best lessons rarely come with a press release.

Let’s get into it. 🎙️

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S2 · E51
Friday · 26 min
From the Pitch to the Pivot (Episode 51 ft. Giacomo Sanvitale)
Giacomo Sanvitale grew up outside Milan, signed with a Swiss club at 15, and followed soccer to the United States through scholarships in Missouri and Oregon, surgeries far from home, and hundreds of cold emails before he landed in Florida. He was also filming the whole time. Starting in 2016, he became the first Italian creator to bring the college athlete life to YouTube, which made him recognizable back home. He now hosts Two Miles With…, a running interview series filmed on Bayshore Boulevard that passed nearly a million views in under four months. This conversation is about what happens when an identity stops fitting. Giacomo explains why he chose to post about anxiety and loneliness after retiring, even though it cost him his sponsors, his management, and 30K followers in two months. He talks about keeping his faith private for years and then deciding to stop, about building a format around his limits instead of waiting for a studio, and about why fatigue makes his guests more honest. "I lost all my sponsors, I lost my management, I lost 30K in two months... and I couldn't care less. I never felt so free." (Giacomo Sanvitale) 21 Minutes With… is The 21st Agency's podcast for operators, leaders, and brand builders.
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S2 · E50
September 14 · 28 min
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 four companies reached a million dollars in their first year. This conversation is about what changes between your first company and your fourth. Buckley breaks down why 80 percent of a first-time founder's motion is wasted, how repetition turned instinct into a system he can run with new teams in new industries, and why he deliberately targets slow, risk-averse sectors like healthcare and education instead of avoiding them. He explains why every product he builds keeps a human at the center surrounded by AI, and why walking into a room without all the answers earns more trust than pitching. Also: two Bernedoodles named Baxter and Bruce, who were part of the go-to-market plan before there was a product. "There are definitely wrong answers, but there's never one right answer." Ed Buckley 21 Minutes With… is The 21st Agency's podcast for operators, leaders, and brand builders.
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S2 · E49
September 4 · 32 min
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 malls around Fort Collins, and came back with a heat map that ended the debate and freed the team to go solve a better problem. He studied sociology, anthropology, and psychology alongside design, and shoots street photography built around capturing what a city feels like rather than what it looks like. This conversation covers why diagnosis is the step most companies skip, why strategy is a creative act rather than an analytical one, and how decisions inside older businesses quietly drift toward internal opinion once nobody goes back to check what the customer actually thinks. Kevin also lands somewhere uncomfortable on AI: he uses it, he does not particularly like it, and he is clear that it is a tool rather than a craftsman. It only produces anything worth keeping in the hands of someone who already has the expertise to judge the output. "Most companies have been skipping leg day."
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August 28 · 36 min
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, she brings a global lens to how people learn to express love, avoid conflict, and armor up. Her work goes to the root cause rather than the coping mechanism. In this conversation, she breaks down why so many founders build businesses out of survival, and why the identity that got them to seven figures eventually becomes a wall — in their marriage, in their leadership, and in their relationship with money. She makes the case that achievement provides safety, control provides protection, and perfection provides identity, but none of them provide worthiness. She explains why the same attachment pattern that shows up in a marriage shows up in how someone holds onto cash. And she offers a daily practice that costs nothing: track your triggers the way you'd track your food. "If you want to have deeply connected relationships, you can only meet people at the depth of where you meet yourself." — Ludmila Woodruff 21 Minutes With… is The 21st Agency's podcast for operators, leaders, and brand builders.
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S2 · E47
August 10 · 29 min
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 permitted to hold professional-level jobs. She started WWC Global anyway, grew it to $100 million in annual revenue and 350 direct employees over 18 years, and sold in 2022. Her book, Unruly, carries a foreword by Gen. Stanley McChrystal. This conversation is about the gap between what the rules say and what everyone assumes they say. Lauren walks through leaving academia when the people around her called it failure, discovering how much interpretive room actually exists inside federal regulation, and building a company she never intended to build — one "yes, we can do that" at a time. She's precise about what she ruled out: by her own description, she is a rule follower to the extreme. The skill was never breaking conventions. It was knowing which ones are load-bearing. "There is so much space within the rules. What the rules say versus what people think they say are two very different things." — Lauren Wittenberg Weiner
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S2 · E46
August 5 · 27 min
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 set and reach their post-high-school goals. He got there from a childhood spent in fifteen different homes. This conversation goes further into the formation than the résumé usually allows. Tony talks about the bagel shop he opened at 23 while working full time at Arthur Andersen — and what its failure taught him about cash flow and about his own expectations of other people. He's direct about the years before the guardrails existed: no curfew, no rules, and a proximity to real criminal activity that he neither dramatizes nor excuses. He explains why he deliberately gravitated toward partners and friends who had been raised differently, and what it took to build a filter in his twenties that most people are handed in childhood. He also names the one offer he accepted that he'd take back. "Money can affect behavior, but it also reflects character." — Tony DiBenedetto
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S2 · E45
July 30 · 24 min
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 through a hedge fund during the 2008 financial crisis, bond trading, hundreds of property flips, and investments in some of Tampa’s most recognizable businesses. This conversation digs into how Ryan evaluates risk, why he entered real estate when the market was collapsing, how RPM Realty approves loans in hours instead of weeks, and why protecting investors matters more than chasing maximum growth. He also shares his perspective on Tampa’s transformation, investing in projects like Motor Enclave, Meat Market, and Ford’s Garage, and why his current goal is simplifying his portfolio rather than adding more to it. “If you’re going the same way the public is going, you’re probably already too late to the party.” — McGuinness
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S2 · E44
July 15 · 25 min
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 firsthand how little technology existed for the people who needed it most. This conversation digs into the decisions behind the company: why he gave the product away free for four years when competitors charged per employee, why he turned down VC advice to go up-market, why he hired people with family-business backgrounds over traditional tech résumés, and how AI has made building at scale feel like the scrappy early days again. "They can't pay a lot of money. They shouldn't pay a lot of money, but their problems are no less acute." — John Waldmann
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S2 · E43
July 9 · 29 min
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 studying what it actually takes to earn trust through a screen. In this conversation, she talks about being pulled off air early in her career to work with a language specialist, why "fake it till you make it" is more honest than most professionals admit, and what separates interviewers who get real answers from those who just get through their list. She also makes the case that curiosity — not charisma, not confidence — is the one quality that determines longevity in any field built on human connection.
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S2 · E42
June 17 · 30 min
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 through the luxury art world, Chanel's brand operations, high-end plumbing manufacturing, and construction revenue leadership before identifying the gap Glam Now was built to fill. In this conversation, Amanda and host Brittany Ward cover the decision to stay adjacent to what she loved rather than push through where she wasn't built to compete, what Chanel's operational standards actually look like from the inside, how supply chain thinking from construction informed a healthcare platform, and what it took to unlock national scale in a highly regulated industry. "That attention to detail was completely honed in — I was sharpened there. It was made there. It was refined there." — Amanda Cuevas 21 Minutes With… is The 21st Agency's podcast for operators, leaders, and brand builders.
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S2 · E41
June 11 · 28 min
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 them. She came up through the home services industry over two decades — starting as a customer service rep managing 17 tradesmen at a family-owned plumbing shop, surviving a private equity acquisition, and eventually building her own business after watching millions of dollars in software go to waste because no one stayed to train the end user. In this conversation, Sheena talks about how she learned to use fear as a compass, why she intentionally worked herself out of every role she ever held, what she saw break down when private equity entered a family-owned business, and how systems, process, and people are the only three variables that actually determine whether a trade business scales. "If it doesn't scare me, it's not big enough. But if it scares me, then I'm definitely going to get something out of it." — Sheena Palacios 21 Minutes With… is The 21st Agency's podcast for operators, leaders, and brand builders.
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S2 · E40
May 29 · 26 min
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 she's built. Elizabeth is a second-degree BJJ black belt, former law enforcement officer, SANE advocate, gym owner, CrossFit coach, and Director of Operations at SOF Missions, a nonprofit supporting veterans in living differently — not just recovering, but advancing. "Be the superhero that you always wish you had." — Elizabeth Kirchmeier This conversation goes into what it actually takes to lead and serve from a place of real self-knowledge — why sitting with your own thoughts matters, what SOF Missions is doing that the VA can't, and how Elizabeth thinks about the character beneath all the credentials. After this one, you'll think differently about what it means to build from nothing.
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S2 · E8
May 7 · 23 min
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 creative gets made, how data gets connected, and how brands survive in a world where the search engine is no longer the gatekeeper. In this conversation, we talk about why companies not integrating AI won't be winning in 12 to 24 months, what the backpack journalist framework means for the next generation of marketers, how DoorDash is actually deploying AI across its marketing org right now, and why AEO is replacing SEO faster than most brands realize.
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S2 · E7
April 30 · 28 min
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, chose Tampa over Silicon Valley when he didn't have to, and 10x'd the business when COVID created the exact conditions Knack was built for. Then he stepped back, deliberately, cleanly, and on his own terms. Now he's building again, and Tampa is about to look very different because of it. After this episode, you'll think differently about what it means to move on and what it means to start over.
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S2 · E6
April 22 · 25 min
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 brands, building a career at the exact intersection of culinary craft and brand strategy. In this conversation, we talk about what it actually takes to translate a chef's passion into a brand story, why beautiful imagery without strategy only goes so far, what she learned squirreling money away before betting on herself, and how nine years of working at the intersection of food, photography, and marketing has shaped the way she sees a plate — and a brand. After this episode, you'll never look at a food photo the same way again.
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S2 · E5
April 15 · 25 min
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 up — creating systems, curating experiences, and flipping a high school stadium into a pro venue every single game day. After this episode, you'll never watch a game day the same way again.
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S2 · E4
April 9 · 33 min
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 Instagram, she built her audience the same way she built her career: by showing up every day long enough for consistency to become compounding. After this episode, you'll think differently about what creative trust actually costs — and what it's worth.
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S2 · E3
March 31 · 26 min
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 grit, mindset, and a relentless refusal to fail. However, it was what came after the final out that tested him most. The identity loss, the income stop, the silence where the crowd used to be — and the hard work of rebuilding from scratch into real estate, business ownership, and a broadcasting career he flew across the country to create for himself. We dig into what it really means to transition out of the game, why the hardest trade-off wasn't the money or the fame, and why the discipline that carried him through 14 seasons is exactly what he's betting on to build what comes next. If you liked this conversation, make sure to follow so you catch the latest from our new episodes.
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S2 · E2
March 26 · 24 min
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 for data, not surveys for strategy — real conversations about real problems that the beauty industry kept dismissing. So she stopped waiting for someone else to solve them. She cleared out her savings, hired a chemist, and built Nakery Beauty from the ground up around the women who'd been ignored the longest. We dive into what it really means to show up for your customer beyond the product, why the most uncomfortable conversations became the foundation of her brand, and how building trust with women turned into a multi-million dollar business with no VC money and no shortcuts. If you liked this conversation, make sure to follow so you catch the latest from our new episodes.
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S2 · E1
March 18 · 27 min
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 felt. He launched one of the fastest-growing travel companies in the US, orchestrated a thousand-person tailgate in Dublin, and acquired a motorcycle tour company in Ireland almost entirely by accident. In this episode, we dig into what it really means to create trips worth remembering, why disruption is the best thing that can happen on a trip, and what it looks like to build a business around passion before profit. If you liked this conversation, make sure to drop a follow so you catch the latest from our new episodes.
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