21 Hats Podcast
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Dashboard: Is AI Killing SEO Spam (and Unleashing Creativity)?
34 mins; April 03, 2026
Managing People Is Hard: When Does Demanding Become Toxic?
49 mins; March 31, 2026
Dashboard: A $2 Million Bet on Banana Ice Cream
39 mins; March 27, 2026
It Took 25 Years to Get Here
49 mins; March 24, 2026
Dashboard: The Case Against Pay for Performance
45 mins; March 20, 2026
For Business Owners, It’s One Battle After Another
45 mins; March 17, 2026
Dashboard: Does Entrepreneurship Have a Perception Problem?
21 mins; March 13, 2026
What’s Harder Now: Getting a Job or Starting a Business?
43 mins; March 10, 2026
Dashboard: Can a Digital Bank Deliver for Business Owners?
32 mins; March 06, 2026
When Your Business and Your Values Collide
42 mins; March 03, 2026
We Can’t Afford to Wait on AI
43 mins; February 26, 2026
Dashboard: Searching for Some Tariff Certainty
25 mins; February 24, 2026
Dashboard: Where Do You Go for Unbiased Exit Advice?
36 mins; February 20, 2026
Hot Seat: Three Owners, No Easy Answers
52 mins; February 17, 2026
Dashboard: Where Do You Turn When You’re Stuck?
32 mins; February 13, 2026
We’re Trying to Outgrow the Valley of Death
46 mins; February 10, 2026
Dashboard: Why Chasing Growth So Often Backfires
30 mins; February 06, 2026
I Can Help with AI. Do Owners Want Help?
50 mins; February 03, 2026
Dashboard: One Industry Just Got an AI Playbook for Running a Business
42 mins; January 30, 2026
I Expect to Grow This Year. Should I Hire Now?
46 mins; January 27, 2026
Dashboard: A Grand Experiment in Buying and Building Small Businesses
48 mins; January 23, 2026
I’m Looking for an Exit
46 mins; January 20, 2026
Dashboard: Why 2026 Will Be a Big Year for Small Businesses
31 mins; January 16, 2026
Do Business Owners Really Want Balance?
48 mins; January 13, 2026
Dashboard: No Text Book Can Prepare You for This
28 mins; January 09, 2026
The Old Rules of Hiring Are No Longer Working
51 mins; January 06, 2026
Dashboard: This Company Covers All of Its Employees’ Health Care
36 mins; January 02, 2026
Do You Have the Stomach for This? 2025 in Review, Part 2
62 hours 55 mins; December 30, 2025
Dashboard: You Can Still Save on 2025 Taxes!
20 mins; December 26, 2025
Do You Have the Stomach for This? 2025 in Review, Part 1
70 hours 35 mins; December 23, 2025
Dashboard: This Is Killing Small Businesses
21 mins; December 19, 2025
Three Branches, Three Brands: Anatomy of a Rebrand
44 mins; December 16, 2025
Dashboard: Your Forecast Will Be Wrong. Do It Anyway
22 mins; December 12, 2025
The Healthcare Dilemma: Protect Employees? Or the Business?
50 mins; December 09, 2025
Dashboard: Tracking the Entrepreneurial Economy
33 mins; December 05, 2025
Best of: We Charge What We Need to Charge
58 mins; December 02, 2025
Dashboard: Finding Employees Is Harder than Finding Customers
30 mins; November 28, 2025
I Have to Figure This Sh*t Out
48 mins; November 25, 2025
Dashboard: Want More Domestic Manufacturing? Think Small
32 mins; November 21, 2025
She Still Packs Every Order as if It’s a Gift
45 mins; November 18, 2025
Dashboard: Seeing Past the Workslop and Hallucinations
30 mins; November 14, 2025
Welcome to Employee Ownership! (Without the Hype)
45 mins; November 11, 2025
Dashboard: Turning Tradespeople Into Business People
29 mins; November 07, 2025
I Thought It Was the Worst Day of My Life
43 mins; November 04, 2025
Dashboard: A Business Owner Chooses His Third and Final Act
42 mins; October 31, 2025
Should I Buy the Building? Or Stick to the Business?
47 mins; October 28, 2025
Dashboard: Even Made in the USA Manufacturers May Not Survive the Tariffs
35 mins; October 24, 2025
Do You Want to Serve Clients—or Build a Business?
46 mins; October 21, 2025
Your Employees Want a Career Path. Can You Keep Them?
45 mins; October 14, 2025
Dashboard: You Probably Should Be Doing More with AI
43 mins; October 13, 2025
It’s Not Too Early to Be Thinking About 2026
44 mins; October 07, 2025
Dashboard: A Business Owner Takes a Sabbatical
26 mins; October 06, 2025
You’re Shutting Down a Profitable Business?
51 mins; September 30, 2025
Dashboard: Married with a Business
31 mins; September 29, 2025
The Product Is Great. Is It a Business?
53 mins; September 23, 2025
Dashboard: How Much Money Can You Make Franchising?
44 mins; September 22, 2025
In Four Years, This Will Be Your Business to Run
52 mins; September 16, 2025
Dashboard: Lessons from a Marketer Who Hates Marketing
26 mins; September 15, 2025
Would a True Capitalist Consider a Worker Co-op?
45 mins; September 09, 2025
Dashboard: Are You Sure Your Business Can’t Be Sold?
29 mins; September 08, 2025
Best of: A Punk Rocker’s Guide to Building a Business
56 mins; September 02, 2025
Best of: Seth Goldman Brews Another Success
36 mins; August 26, 2025
Dashboard: A Business Owner Exits on His Own Terms
40 mins; August 25, 2025
It’s a Bear Market for Citibin
46 mins; August 19, 2025
Dashboard: Can AI Save Small Businesses from Google?
24 mins; August 18, 2025
When Your Biggest Hire Ever Is a Bust
44 mins; August 12, 2025
Dashboard: Any Business Can Afford This CFO
27 mins; August 11, 2025
Laura Zander Named Her Exit Price
49 mins; August 05, 2025
Dashboard: ‘We’re Not Giving Up’
22 mins; August 04, 2025
Those Who Can, Do. Those Who Can’t, Uh, Coach?
44 mins; July 29, 2025
Dashboard: A Few Ideas to Really Help Small Businesses
25 mins; July 28, 2025
How Many Clients Did That Post Bring You?
46 mins; July 22, 2025
Dashboard: Are You Risking Everything You’ve Built?
33 mins; July 21, 2025
Do I Want to Work with My Family?
46 mins; July 15, 2025
Dashboard: Are We Getting Better at Teaching Entrepreneurship?
38 mins; July 14, 2025
Straight Talk About ESOPs and Co-Ops and EOTs, Oh My!
50 mins; July 08, 2025
Dashboard: A Big Beautiful Win for Small Businesses?
43 mins; July 07, 2025
Something’s Happening in the Job Market
56 mins; July 01, 2025
Dashboard: Three Metrics for ‘White Knuckle’ Times
23 mins; June 30, 2025
Why Don’t You Just Sell the Business?
54 mins; June 24, 2025
Dashboard: Don’t Believe the AI Hype (Yet)
26 mins; June 23, 2025
‘America Sucks at Small Business’
46 mins; June 17, 2025
Dashboard: Introducing America the Entrepreneurial
18 mins; June 16, 2025
‘The General Purpose Agency Is Doomed’
55 mins; June 10, 2025
Dashboard: Is the GOP Tax Bill Good for Business?
18 mins; June 09, 2025
‘Mom, I Am Not Taking the LSAT’
59 mins; June 03, 2025
Dashboard: The Best Kept Secret in Business Lending
29 mins; June 02, 2025
How Big Do I Want My Business to Be?
38 mins; May 27, 2025
Dashboard: Bringing AI into the Sales Process
26 mins; May 23, 2025
We Get Paid to Judge People
45 mins; May 20, 2025
Dashboard: A Glimmer of Hope for Small Businesses
23 mins; May 19, 2025
‘I’ll Tax Your Seat’
52 mins; May 13, 2025
Dashboard: They Should Have Fired Themselves
27 mins; May 12, 2025
Maybe Earnouts Aren’t as Bad as You Think
51 mins; May 06, 2025
Dashboard: There’s Still a Talent Crisis for Small Businesses
24 mins; May 05, 2025
Dear ChatGPT: What Are My Blind Spots?
45 mins; April 29, 2025
Dashboard: A Tech Update for Small Business Owners
29 mins; April 28, 2025
I’d Love to Manufacture in the U.S.
48 mins; April 22, 2025
Dashboard: Every Business Has a Story to Tell
33 mins; April 21, 2025
The Hidden Cost of Bad Hiring
39 mins; April 15, 2025