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PODCAST

21 Hats Podcast

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

business entrepreneurship

All Episodes

20:07

Dashboard: How Gene Marks Stopped Sweating Health...

21 Hats Podcast ·

2022/11/14

You want to negotiate with Blue Cross every year? Go ahead. Gene Marks tells Loren Feldman he's found an alternative that he believes allows him to take care of his employees without the hassle of actually buying health insurance. Plus: Why Gene doesn’t discount his services for nonprofits and what he thinks is the most important takeaway for business owners from last week’s midterm elections.

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47:08

There’s Big Money All Over the Place

21 Hats Podcast ·

2022/11/08

This week, in episode 131, Shawn Busse tells Jay Goltz and Sarah Segal that he sees all kinds of opportunities for small businesses, including his own, in the coming wave of climate-related government spending and tax credits. Count Jay among the convinced. He’s got four buildings, five vans, a truck, some Sprinters, and a parking lot where he could put a charging station. If there’s government money available for upgrades, he asks, “Why wouldn’t I do that?” Plus, Jay explains how he’s rethinking

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21:31

Dashboard: Don’t Leave It to Your CPA

21 Hats Podcast ·

2022/11/07

This week, Gene Marks tells Loren Feldman that there are still lots of ways to save on taxes this year, but he also issues a warning: It’s a mistake for owners to just take their financials to the same CPA every year and assume he or she knows everything. Every few years, Gene says, you should take your returns to a different accountant and see if fresh eyes spot alternative tax opportunities for you to consider. Plus: Why Gene thinks you should ignore those third-quarter GDP numbers, and why he

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47:05

Should You Be in a Business Group?

21 Hats Podcast ·

2022/11/01

This week, in episode 130, Sarah Segal, Jay Goltz, and special guest Leo Bottary have a hype-free conversation about why peer-advisory groups like Vistage, YPO, and EO can be life-changing for business owners and why they’re not for everyone. Sarah has been wondering if they’re for her. Jay, who’s been in six different peer groups, says it can be worth the price of admission just to see how other owners run their businesses—but there are reasons he keeps leaving the groups he joins. And Leo is a

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18:52

Dashboard: Would You Hire Them Again?

21 Hats Podcast ·

2022/10/31

Kurt Wilkin, co-founder of HireBetter, tells Loren Feldman he thinks concerns about a recession are largely media-driven, but if your business is slowing, this might be a good time to reevaluate your team: Are you happy with everyone you’ve hired? Plus: What does it mean that wages kept rising in the third quarter? Should job listings include salary ranges? And what would Kurt tell business owners who struggle with compensating themselves?

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40:10

A Founder’s Year: Successful Raise, Fast Growth, and...

21 Hats Podcast ·

2022/10/25

This week, in episode 129, Hans Schrei tells Shawn Busse why this has been a difficult year at Wunderkeks—despite many outward signs of success. It has to do with buying into the need to raise money and shoot the moon. It has to do with accepting the accolades that come with entrepreneurial achievement and then questioning your own self-worth when those accolades stop coming. It’s what Hans calls, “the miracle worker complex.” Hans and Shawn also discuss what it means to rely upon a sales platform

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22:39

Dashboard: Gene Marks Has One Piece of Tech Advice

21 Hats Podcast ·

2022/10/24

Before you spend more on technology, he says, you might want to figure out how to make the best possible use of the tech you already have. Crazy, huh? Gene also talks about the key elements of a buy-sell agreement, how to get your employees to actually use your CRM system, and whether all of our ever-expanding array of productivity tools actually help productivity.

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49:11

Rule No. 1: We Will Not Have Civil Wars

21 Hats Podcast ·

2022/10/18

This week, in episode 128, Shawn Busse, Paul Downs, and Liz Picarazzi talk about why it’s so easy for tension to break out inside a business. Liz sees tension brewing between her people in the office and her people in the field. Shawn often sees friction at businesses between sales and those who have to deliver what sales sells. Paul says there’s always the potential for tension when a project gets handed from one set of workers to another, and he’s created a very deliberate process to address it

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31:07

Dashboard: Victor Hwang on Entrepreneurship in America

21 Hats Podcast ·

2022/10/17

Founder of entrepreneurial advocacy organization Right to Start, Hwang suggests bipartisan policy changes that would help Americans build more businesses. He also talks about what he learned about entrepreneurs on his recent cross-country roadtrip, why funding of U.S. businesses is broken, and what Americans really think of business owners.

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50:16

Dana Opens in Dallas

21 Hats Podcast ·

2022/10/11

This week, in episode 127, Dana White tells Paul Downs and Jay Goltz how her move to Dallas is going, including hiring a manager, firing a publicist, tweaking her business model, and for the first time, confronting competition. Dana also explains the surprising way she managed to get the financing to open her first salon on a military base, Ft. Bragg, which she now thinks could be up and running by the end of the year. Plus: Paul has to make adjustments to handle a sudden influx of business. And

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28:10

Dashboard: Welcome to Health Insurance Season!

21 Hats Podcast ·

2022/10/10

This week, as many businesses find out what they’ll pay for health insurance next year, Gene Marks and Loren Feldman talk about how businesses can save money. Gene explains why self insurance has become more feasible for smaller businesses and why he thinks it makes sense to offer employees better health coverage instead of a pay increase. Also, it’s probably time to revisit your workplace drug policies. And Gene and Loren discuss why the concerns of small businesses often get overshadowed by those

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35:04

Bonus Episode: Seth Goldman Brews Another Ice Tea

21 Hats Podcast ·

2022/10/07

This week, in a special bonus episode recorded right before Labor Day, Seth Goldman talks about getting the disappointing news that Honest Tea, the brand he built and sold to Coca Cola, was being discontinued—and how it took him about two weeks to decide to create another tea business, Just Ice Tea, to fill the shelf space that Coke was vacating. Along the way, Goldman talks about why it made sense to sell a mission-driven business to a soda company, what he wishes he had done differently in the

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41:06

Are You Hitting Your Numbers?

21 Hats Podcast ·

2022/10/04

This week, in episode 126, Karen Clark Cole, Jay Goltz, and Sarah Segal discuss whether their businesses are meeting expectations and how that’s affecting their plans for next year. They also talk about how to handle an employee who doesn’t deliver, whether now is a good time to hire, and—in an answer to a listener question—how to make the transition from using contractors to hiring employees. And Karen explains why employee utilization—that is, what percentage of her people are actually billing

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18:32

Dashboard: I Like Recessions

21 Hats Podcast ·

2022/10/03

This week, Loren Feldman speaks with Tracy Bech, who is CEO of Starboard Collectives and who specializes in helping business owners who don’t have a financial background (she understands: she was once one herself). Tracy talks about the two most important ratios for business owners to watch if they think we’re heading into a recession. And she also talks about why she actually likes recessions—or at least sees opportunities in them.

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40:23

Raising Capital: 'It’s a Ticking Time Bomb'

21 Hats Podcast ·

2022/09/27

This week, in episode 124, Shawn Busse, Liz Picarazzi, and Hans Schrei debate the merits and risks of taking outside capital. Clearly, it makes sense for some businesses. But what are the right circumstances? What are the alternatives? And what do you need to understand before going to the dance? For example, what are the dynamics of the entrepreneur-investor relationship? Are the entrepreneurs hoping the investors will bestow an opportunity upon them? Or is it actually the entrepreneurs who have an

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23:11

Dashboard: The (Commercial) Rent Is Too Damn High

21 Hats Podcast ·

2022/09/26

This week, Gene Marks and Loren Feldman talk about what business owners can do to protect themselves in the current environment of rising rents and increased volatility. Plus: What explains the recent boom in startups? And will it last? And what the Fed’s rate hikes mean for businesses. Also: you can’t just set your website and forget it.

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43:18

Should HR Advocate for the Business or the Employee?

21 Hats Podcast ·

2022/09/20

This week, in episode 124, Karen Clark Cole, Jay Goltz, and Sarah Segal talk about hiring an HR person. First, how do you handle HR issues before you can afford HR people? Is software the answer? At what size does a business need a full-time person? Do you hire someone who has experience but who might not be used to getting his or her hands dirty? Or do you hire someone you can mold to fit the culture of your business? Jay, who likes to say the entrepreneur is often the worst person to interview

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23:14

Dashboard: Could California’s Fast Food Regulations...

21 Hats Podcast ·

2022/09/19

Signed by Governor Newsom on Labor Day, California’s new fast food law creates committees, among other things, to set an industry-wide minimum wage. The plan sparked lots of outrage, but Gene Marks explains why he thinks it’s worth a try. He also notes that it could well be coming to a state near you. Plus: Gene also makes the business case for paid parental leave while also raising some interesting questions, including this one: If you offer paid leave to new parents, is that fair to employees who

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45:53

Bonus Episode: Jason Fried Didn’t Mean to Blow Up...

21 Hats Podcast ·

2022/09/16

This week, in a special bonus episode, Jason Fried talks about why things got crazy at software maker Basecamp and what it has meant for the business. As you may recall, in the spring of 2021, Fried, CEO and co-owner, issued a blog post edict eliminating a slew of benefits, shutting down a committee that had been attempting to address diversity issues, and barring discussion of all social or political issues on work forums. The email produced a backlash that culminated in a third of the company’s

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47:26

Quiet Quitting: Another Gift Brought to You by...

21 Hats Podcast ·

2022/09/13

This week, in episode 123 and in light of reports that half of the U.S. workforce has “quietly quit” their jobs, Shawn Busse, Paul Downs, and William Vanderbloemen talk about the latest rage: Is quiet quitting something new? Is it just a media creation? Have Shawn, Paul, and William experienced it in their businesses? And who’s to blame? Plus, the three owners explain how they hire for engagement and how they’ve changed their hiring processes in response to the pandemic and the labor shortage. For

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527 results

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