21 Minutes With...

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. 🎙️

21 Minutes With... is a business podcast hosted by Unknown Host, with 48 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Unknown Host hosts 21 Minutes With..., a business show with 48 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

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  Episode #49

  Question Everything (Episode 49 ft. Kevin Meyer)

  Sep 4, 202633 minS2

  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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  21 Minutes With...

  A Global Perspective on Relationships (Episode 48 ft. Ludmila Woodruff)

  Aug 28, 202636 min

  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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  Episode #47

  The Oval Office Operator (Episode 47 ft. Lauren Wittenberg Weiner)

  Aug 10, 202630 minS2

  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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  Episode #46

  The Tampa Tech Architect (Episode 46 ft. Tony DiBenedetto)

  Aug 5, 202627 minS2

  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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  Episode #45

  How to Build a Real Estate Empire (Episode 45 ft. Ryan McGuinness)

  Jul 30, 202625 minS2

  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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