21 Minutes With...

The 21st Agency
  • 5.0 (1)
  • Marketing
  • Updated Weekly

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. 🎙️

  1. 13h ago

    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."

  2. Aug 28

    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.

  3. Aug 10

    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

  4. Aug 5

    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

  5. Jul 30

    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

  6. Jul 15

    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

  7. Jul 9

    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.

  8. Jun 17

    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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About

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. 🎙️

Information

  • Creator
    The 21st Agency
  • Years Active
    2026
  • Episodes
    48
  • Rating
    Explicit
  • Copyright
    © 2026 The 21st Agency
  • Show Website
    21 Minutes With...