Small-business reality, without the polish.
21 Hats Podcast is built around owners talking through live business problems, not victory-lap stories. Recent episodes move from HR sales and service pricing to trade shows, restaurant staffing, AI’s effect on marketing, and the slow work of building systems.
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21 Hats Podcast looks at small business from inside the operating room, where every decision has a cost and every clean theory runs into people, cash, time, and habit. Loren Feldman anchors the conversations with direct questions and enough patience to let owners explain how things really work. The show is not built around polished founder myths. It is built around situations that are still live. One episode follows Sandy Capel as she tries to translate corporate HR expertise into something small-business owners will value and buy. Another has Sarah Siegel thinking through PR pricing, consistency across clients, and the tension between being fair and staying profitable. Lisa Woodruff’s story starts with household overwhelm and turns into a business built around systems for busy people. Sean Bussey talks through marketing, AI, SEO, and the practical strain of finding growth beyond a tough local market. Chris Campbell describes the all-consuming work behind Banana Daddy, from guest experience to food made from scratch and a large new staff. Other conversations push into harder management territory. The show asks when demanding standards become toxic, what to do with a high performer who damages the team, and whether systems can matter more than stars. It also spends time on the long, slow path out of founder dependence, where owners begin to see daylight only after years of work. Trade shows, trademarks, Google traffic, outsourced marketing, tariffs, employee travel, workflow, margins, and culture all become part of the same larger question: what does it actually take to run a durable small company? The appeal is the plainness. People disagree, pause, revise, and test their assumptions against experience. The result is business talk with fewer slogans and more usable friction.
Made for: For small-business owners, operators, and advisors who want candid conversations about pricing, people, systems, growth, marketing, and owner judgment. It especially suits listeners who prefer practical diagnosis over startup mythology.
What sets it apart: The show’s strength is its live operating texture: owners talk through active problems with numbers, staffing realities, customer pressure, and personal limits still in view. It treats business advice as something to test, not something to recite.
The 21 Hats Podcast presents an authentic weekly conversation with small business owners who are remarkably willing to share what’s working for them and what isn’t. Unlike many business podcasts, which tend to talk to highly successful entrepreneurs whose struggles are in the past, the 21 Hats Podcast features a rotating cast of business owners who are still very much in the trenches fighting the good fight. Every week, our regulars gather to talk about the kinds of important issues many owners won’t even discuss behind closed doors: whether their businesses are as profitable as they should be, whether they are willing to give up some control to an investor in order to grow faster, why they…
Based on 6 episodes we listened to · September 2026
Loren Feldman makes small-business decisions legible by testing management ideas against staffing, financing, growth, and the realities of launching companies.
21 Hats Podcast turns business ownership into a working session. Loren Feldman alternates between roundtable conversations among owners and focused Dashboard interviews, keeping attention on decisions still being tested.
A star employee steals accounts; you get an owner's case for building a stronger system.
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Short reviews from the PlayNext desk, based on the episodes we processed.
A blunt owner to owner discussion about where hard standards start to cross the line.
The episode opens on the Noma horror stories and moves straight into a tougher question: when does high standards tip into something else? Loren Feldman hosts, and Jay Galtz, Jennifer Caron, and Ted Wolfe keep the discussion grounded in plain owner problems rather than polished…
A grounded look at the labor, costs, and judgment behind a new food concept.
Chris Campbell's account of launching Banana Daddy in Miami is strongest when it stays on the ground level: rent, overhead, marketing spend, PR, staffing, training, and what guests actually experience once the doors open.
A hard look at growth once systems start to strain.
Loren Feldman sits with Paul Downs, Jennifer Caron, and Jackie Russo as they trace the slow climb out of the Valley of Death, where a business still leans on its owner for everything before it begins to outgrow its people and systems.
Kelly Allen argues that sales incentives change best through education, small experiments, and employee involvement, not top-down commands.
The episode challenges a stubborn sales belief: make the rewards big enough, and the results will take care of themselves. Through Kelly Allen's discussion of W.
AI, energy costs, and expensive credit test owner judgment.
Business owners here are shown making long-range decisions while the ground keeps moving. The episode ties that pressure to equipment purchases, AI investment, and borrowing, then follows the effects into parts of finance that can be easy to overlook.
A clear, candid episode about running a company without letting it overrun a marriage.
Loren Feldman turns Cameron Medill's departure from Pixelspoke into a broader look at what work can ask of a marriage when entrepreneurship becomes central to identity.
Rob Walling on bootstrapped SaaS growth, plateaus, and exits — with founders who lived them.
Abbey Ashley's playbook for turning your job skills into a virtual assistant business.
Naval Ravikant on epistemology, startups, and crypto, from David Deutsch to Vitalik Buterin.
Alex Theuma interviews SaaS founders and investors on scaling to $10M-plus ARR.
Guy Raz traces founders' origin stories and fields live advice-line calls from entrepreneurs.
Alex Blumberg interviews guests like Megan Phelps-Roper and Shane McAnally about failure and reinvention.
This episode is part one of a year-end special reviewing 2025 conversations with entrepreneurs discussing real-life business challenges like layoffs, pricing, manufacturing, and valuation.
Lisa Woodruff, founder of Organize 365, discusses how she built a business by applying organizational systems to household management.
Cameron Medill returns to the 21 Hats Podcast to discuss his research on entrepreneurs and their marriages.
This episode features an interview with Jonathan Grzybowski, co-founder of Penji, discussing how his platform provides creative marketing services to small businesses through a subscription model with personalized talent matching and fast delivery.
This episode features a brainstorm session with business owners to help HR consultant Sandy Capel refine her approach to selling HR services to small businesses that typically resist or lack formal HR departments.
Lisa Woodruff discusses how she founded Organize 365 to help women manage household overwhelm by creating organizational systems, sharing her personal journey from overwhelmed stay-at-home mom to business CEO.
This episode explores how to price services in a business by balancing client needs with profitability, featuring a discussion with PR expert Sarah Siegel and other entrepreneurs.
This episode explores whether AI is eliminating SEO spam and fostering creativity in marketing, featuring a discussion with Sean Bussey about his company's challenges and expansion into new markets.
High standards can curdle.
Banana Daddy was not the obvious next move.
Loren Feldman opens by noting that 2026 has started well for Paul Downs, Jennifer Caron, and Jackie Russo.
The host speaks with Kelly Allen, a management consultant and proponent of W.
Owners are making decisions in a stretch shaped by a pandemic, inflation, tariffs, war with Iran, soaring energy prices, and uncertainty around artificial intelligence.
This episode explores whether small business owners are willing to pay for help adopting AI and if there's a viable business opportunity in providing such consulting services.
This episode is part two of a year-in-review special featuring highlights of conversations with entrepreneurs discussing their real-life business challenges, successes, and difficult decisions from 2025.
This episode is part one of a year-end special reviewing 2025 conversations with entrepreneurs discussing real-life business challenges like layoffs, pricing, manufacturing, and leadership decisions.
This episode explores the realities of employee ownership through ESOPs with Chris Maynard and Justin Jordan of Cathedral Holdings, discussing both benefits like tax advantages and significant risks including business failure and employee engagement challenges.