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Artwork for 21 Hats Podcast

21 Hats Podcast

21 Hats
Tariffs
Small Business
Economic Uncertainty
Entrepreneurship
Employee Management
Financial Management
2024 Financial Statements
Small Business Challenges
Linkedin Poll
Covid-19 Impact
Bookkeeping Practices
Profit Margins
Expenses Management
Small Business Management
Lyx
Covid-19
Business Growth Strategies
Client Relations
Artificial Intelligence
Segal Communications

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 ... more

PublishesTwice weeklyEpisodes539Founded6 years ago
Number of ListenersCategories
NewsBusiness NewsEntrepreneurshipBusiness

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Artwork for 21 Hats Podcast

Latest Episodes

Sean Joy is head of M&A at Chenmark, a Portland, Maine-based holding company that acquires a handful of small businesses each year. At first glance, Chenmark may sound like a traditional private equity firm, but it isn't. The company is family- and e... more

This week, we explore some contrasting opinions about artificial intelligence. Paul Downs has serious doubts that AI will ever have a significant impact on his business. Paul, who builds custom conference tables, says his business depends on somethin... more

When Bryan Clayton graduated from college, he discovered he had two options: take an entry-level job and a pay cut—or go back to mowing lawns, which was already making him more money. He chose the lawns. Over time, he built a commercial landscaping b... more

Twenty years ago, Bo Burlingham gave a name to a feeling a lot of business owners had struggled to articulate. In his book Small Giants, Bo profiled companies that had chosen not to chase growth at all costs. Most were bootstrapped, owner-operated bu... more

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Recent Guests

Jean Moncrieff
Leader of the Small Giants organization
Small Giants
Episode: In Search of Companies More Interested in Being Great Than Big
Eugene Khayman
Co-founder of Million Dollar Sellers, a community for e-commerce founders
Million Dollar Sellers
Episode: Dashboard: Is It Still Worth Selling on Amazon?
Michelle Wyatt
Owner of St. John's Rivership, a dinner and entertainment river cruise
St. John's Rivership
Episode: When Employee Violence Walks Through Your Door
Hannah Sandmeyer
Founder and CEO of Steward Market
Steward Market
Episode: Dashboard: A Marketplace for Ethical Exits
David C. Barnett
Based in New Brunswick, Canada, helps people buy and sell businesses
Independent business broker/advisor
Episode: The Real Payoff May Be in Owning, Not Selling
Paul Downs
CEO of Paul Downs Cabinetmakers; discusses his exit considerations
Paul Downs Cabinetmakers
Episode: The Real Payoff May Be in Owning, Not Selling
Shawn Busse
CEO and founder of Kinesis
Kinesis
Episode: Dashboard: Should You Pay $3,500 a Month for SEO?
Liz Picarazzi
CEO of City Bin, trash enclosures
City Bin
Episode: When That Big Break Just Might Break You
Keith Wallace
Founder of the Wine School of Philadelphia
Wine School of Philadelphia
Episode: Dashboard: Bringing a Bazooka to a Wine Fight

Host

Lauren Feldman
Host of the 21 Hats Podcast, frequently moderating discussions with a focus on small business issues and storytelling.

Reviews

5.0 out of 5 stars from 52 ratings
  • Must listen for every small business owner

    I have listened to every single episode of 21 hats. This is my favorite business podcast as a small business owner. Real business owners sharing real wins and losses in real time. Must listen.

    Apple Podcasts
    5
    Organize 365
    United Statesa month ago
  • Started listening in 2024 and have enjoyed so many episodes. It's nice to finally have a business podcast with content that I can easily relate to and often apply to my business. I highly recommend trying 21 Hats.

    Podcast Addict
    5
    marshall pinky
    a year ago
  • Excellent for update to date information

    I have been listening to this podcast for a couple of years now. Loren always has a wide array of great contributors. My favorite is Paul Downs.

    Apple Podcasts
    5
    Glassbusinessguy
    United States2 years ago
  • Great resource for entrepreneurs

    This podcast and the 21 Hats newsletter is a welcome resource to help entrepreneurs and SMB owners to be successful!

    Apple Podcasts
    5
    Texas Kurt
    United States2 years ago
  • A must listen for small business owners

    Owning a small business can be lonely, so listening to other owners talk about their day-to-day is a pleasure. Loren expertly moderates a group of diverse (lots of women’s voices - thank you!) owners who are candid, approachable, and entertaining.

    Apple Podcasts
    5
    Green day fan 17
    United States5 years ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

Listeners value the candid, diverse voices and practical mentoring from peers.
Shows focus on real-world small business struggles, not just polished success stories.
Guests and hosts are perceived as knowledgeable and approachable, making topics relatable for owners.

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Talking Points

Recent interactions between the hosts and their guests.

In Search of Companies More Interested in Being Great Than Big
Q: What exactly is Small Giants today, who is it for, and how is it different from similar organizations?
It's a community focused on helping business owners grow with intention, emphasizing culture, leadership, and a sustainable model rather than mere scale; it uses programs like leadership academies and open-book principles to support ongoing development and meaningful growth.
The Real Payoff May Be in Owning, Not Selling
Q: What are the key risks in delaying an exit, and how can owners mitigate them?
The guests highlight market shifts, potential declines in multiples, the need for clear communication, and practical steps like gradual equity vesting and performance-based bonuses to seed ownership.
The Real Payoff May Be in Owning, Not Selling
Q: How do you structure a sale or transition to keep control and ensure the business continues to perform?
The panel discusses staged ownership, thresholds for equity grants, roles of the leadership team, and financing arrangements that allow owners to step back gradually while employees gain stake and distributions.
The Real Payoff May Be in Owning, Not Selling
Q: Kate, what's your latest thinking on selling versus staying invested in the business?
Kate explains she's shifting from a traditional sale timeline to exploring an Employee Ownership Trust or other internal transfer options, with a goal of giving ownership to her team while maintaining some advisory role and protections for herself.
When That Big Break Just Might Break You
Q: Could you start by telling us exactly what the opportunity was and how you won it?
Liz explains that New York City's Clean Curbs program aimed to containerize trash; Times Square acted as the fast-tracked pilot that demonstrated demand and catalyzed city-wide adoption, with CitiBin's enclosure becoming a high-profile solution that spurred the entire initiative.

Audience Metrics

Listeners, social reach, demographics and more for this podcast.

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Frequently Asked Questions About 21 Hats Podcast

What is 21 Hats Podcast about and what kind of topics does it cover?

A practical, entrepreneur-focused show that features a rotating cast of small business owners who share real-world wins and challenges. Episodes typically cover profitability, hiring, leadership, operational systems, and practical strategies for growth, often with a candid emphasis on trade-offs, mental health, and personal resilience. Noteworthy is the mix of hands-on business advice, human-centric storytelling, and frequent discussion of real-world constraints like tariffs, hiring costs, and workforce management, making it valuable for listeners who want actionable insights from fellow owners and operators.

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How many listeners does 21 Hats Podcast get?

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What are the audience demographics for 21 Hats Podcast?

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Which podcasts are similar to 21 Hats Podcast?

These podcasts share a similar audience with 21 Hats Podcast:

1. How I Built This with Guy Raz
2. Acquisitions Anonymous - #1 for business buying, selling and operating
3. Organize 365 Podcast
4. Best of Both Worlds Podcast
5. WSJ What’s News

How many episodes of 21 Hats Podcast are there?

21 Hats Podcast launched 6 years ago and published 539 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

How do I contact 21 Hats Podcast?

Our systems regularly scour the web to find email addresses and social media links for this podcast. We scanned the web and collated all of the contact information that we could find in our podcast database. But in the unlikely event that you can't find what you're looking for, our concierge service lets you request our research team to source better contacts for you.

Where can I see ratings and reviews for 21 Hats Podcast?

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What guests have appeared on 21 Hats Podcast?

Recent guests on 21 Hats Podcast include:

1. Jean Moncrieff
2. Eugene Khayman
3. Michelle Wyatt
4. Hannah Sandmeyer
5. David C. Barnett
6. Paul Downs
7. Shawn Busse
8. Liz Picarazzi

To view more recent guests and their details, simply upgrade your Rephonic account. You'll also get access to a typical guest profile to help you decide if the show is worth pitching.

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