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

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

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

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.

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.

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.

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.

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.

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.

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.