Gen Z Is Changing the Workplace

‘Hey I woke up and I’m not in a good place mentally,’ went the typical text message. ‘I’m not going to come in today.’

Good morning!

Reminder: I recently posted my plan to turn 21 Hats into a sustainable business. You can READ MORE HERE. The upshot is I’m asking readers to sign up as either a Paid Subscriber or as a Founding Member.

Here are today’s highlights:

  • A fast-growing startup provides booking software to barber shops.

  • Under the Biden vaccine mandate, employees may have to pay for weekly tests.

  • The Plug covers Black and brown entrepreneurs.

  • The 21 Hats Spotlight: a business that specializes in “Disnification.”


Gen Z is having an impact in the workplace, and even Millennials aren’t sure what to do: “It’s a fault line that crisscrosses industries and issues. At a retail business based in New York, managers were distressed to encounter young employees who wanted paid time off when coping with anxiety or period cramps. At a supplement company, a Gen Z worker questioned why she would be expected to clock in for a standard eight-hour day when she might get through her to-do list by the afternoon. At a biotech venture, entry-level staff members delegated tasks to the founder.”

  • “‘These younger generations are cracking the code and they’re like, ‘Hey guys, turns out we don’t have to do it like these old people tell us we have to do it,’ said Colin Guinn, 41, co-founder of the robotics company Hangar Technology. ‘We can actually do whatever we want and be just as successful.’ And us old people are like, What is going on?’”

  • “Gabe Kennedy, 30, founder of the herbal supplement brand Plant People, noticed as he recruited Gen Z employees that some had no interest in the rigid work habits that felt natural to his mostly Millennial 10-person team.”

  • “He and his co-founder were accustomed to spending late nights in the office obsessing over customer feedback and sharing Chinese takeout. His youngest employees preferred to set their own hours.”

  • “Ali Kriegsman, 30, co-founder of the retail technology business Bulletin, wasn’t sure, in the past, how to respond when her Gen Z employees insisted on taking days off for menstrual cramps or mental health: ‘Hey I woke up and I’m not in a good place mentally,’ went the typical text message. ‘I’m not going to come in today.’” READ MORE


The Biden vaccine mandate is expected to let employers make employees pay for weekly tests: “The emergency rule, which will apply to companies with at least 100 employees and is expected to be released next week, will give employers the option of paying for testing and masks for unvaccinated workers or compelling those employees to foot the bill themselves, according to the sources, who requested anonymity because they didn’t have approval to discuss the rule making.”

  • “Employers will be required to absorb testing and mask costs in cases where a worker qualifies for an exemption to vaccination under federal law, the sources said.”

  • “Unvaccinated workers will be required to wear masks while indoors and in close contact with coworkers, the sources said.”

  • “After it is released, the rule will allow for an implementation period before employers must comply or face citations of up to $14,000 per violation, the sources said.” READ MORE


An app that provides booking software to barber shops raised capital at a $750 million valuation: “New York City-based Squire sells its software and services to more than 2,800 barbershops in the United States, Canada and the U.K. Each pay a monthly subscription (ranging from $100 to $250 per month per location), plus additional transaction fees. Squire’s software (which shops typically rebrand with their own logo) offers not only basic booking and payment services, but it can help divvy up the receipts among a shop’s many barbers. It can automatically manage the payouts of tips, as well as handle payments for chair rentals.”

  • “The firm brought in some $4 million in revenue last year despite waiving subscription fees during the pandemic when nearly all barbershops were shuttered. It’s on track to triple that figure, to more than $12 million.”

  • “Just a few years ago investors were skeptical about developing technology for small businesses and blue-collar workers. But thanks to the success of companies like Carpinteria, California-based Procore (software for construction sites, now publicly traded at a $13.8 billion market cap) and Los Angeles-based ServiceTitan (which makes apps for plumbers and other tradespeople, valued at $9.5 billion), the idea is now mainstream.”

  • “An added twist: The founders of both Procore and ServiceTitan are Squire investors.” READ MORE

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THE 21 HATS SPOTLIGHT: Deliver Service Now Institute

We recently asked Morning Report subscribers to introduce themselves by sending a photo and answering a few questions. Are you ready for your spotlight?

Tell Us About Your Company

Name: Vance Morris

Position: Owner

Location of business: Centreville, Md.

Nature of business: Showing business owners how to become the Disney of their town or niche. “Disnifying” is creating experiences out of the mundane. I offer exclusive three-day boot camps at Walt Disney World, group and individual coaching, and have a group of monthly subscribers. All are invested in price elasticity through experiences they create.

Number of employees: Six virtual assistants, each of which has their own area of expertise: editing, visual, phones, research, posting to social media so I don’t have to.

What you would do differently if you had it to do over: Start my consulting business sooner. I am a former birth control factory security guard, turned rock star, turned Disney leader, turned corporate muckety muck (15 years of hospitality), turned carpet cleaner, turned entrepreneur, turned coach/consultant.

What you get to do on the days you enjoy most: The process of creating experiences out of the mundane is energizing and profitable. Take for example, answering the phone. Ninety-nine percent of companies answer the phone with some version of “Thank you for calling ABC company, how can I help you?” A phone-answering experience would be saying in their best radio DJ voice, “Thanks for calling Biff’s Allstate, the agency that rocks!”

One aspect of running a business you have yet to master:  Sales. I can market with the best of them. Sales, not so much — though my reputation and past clients make it so I don’t have to do much selling.

Problem you would most like to solve now: Convincing business owners that they are in a commodity business and that the only thing that will lift them over the masses is the experience they provide. This is truly MY problem. My sales cycle has to convince a prospect that: a) their service sucks, b) their client retention sucks (or can be improved), or c) demonstrate that they ARE in a commodity business, before I can prescribe/sell my products or services. READ MORE


This is how crazy the used-car market has gotten: “The 2019 Honda Civic that kicked off a used-car auction earlier this month would have been nothing special before the pandemic. But as automotive dealer Brad Wimmer watched, the online bidding quickly became, to quote him, ‘bananas.’ As a new car, the Civic would have had a sticker price of around $21,000. But within seconds at the wholesale auction, the two-year-old model, with 4,000 miles, sold for $27,200.”

  • “A two-year-old minivan prompted feverish competition before Hertz won it for $39,200, a few thousand dollars over its original sticker price.”

  • “The unraveling of the used-car market is the most tangible result of a problem that has plagued the global economy for the past year: a dire shortage of computer chips that has hobbled auto manufacturing.”

  • “‘It’s going to be really, really tough for consumers to buy a vehicle in 2022, a used or a new car. You’re going to have to pay a very high sticker price,’ Wimmer said as he watched the auction  ...” READ MORE


The Plug focuses on Black and brown entrepreneurs: “In 2019, data journalist Sherrell Dorsey wrote a story for the Columbia Journalism Review about how Black and brown tech entrepreneurs were not being covered by the American tech and business press in a meaningful way. Now, despite promises to ‘do better’ and some progress in the wake of the Black Lives Matters protests in the summer of 2020, Dorsey thinks there’s still a long way to go. But instead of trying to get stories placed in mainstream publications, she decided to start her own. Meet The Plug, a news outlet and research company focused on covering the ways that ‘Black people are affected by and engaged with the innovation economy.’”

  • “Dorsey decided to launch a research wing of The Plug because as a graduate student trying to report on Black entrepreneurship, she saw few dollars going into research on Black startups.”

  • “She developed a dataset and heatmap of all the Black-owned co-working spaces in the U.S. When companies and executives started reaching out to her asking for the data, she knew there was a bigger opportunity there.”

  • “‘If I build a Black Bloomberg, I can create a sustainable business model,’ Dorsey said. ‘The research that we need doesn’t even exist, so we have to build it.’” READ MORE


I Track Everything You Could Possibly Measure: Several weeks ago, we had a great conversation about how Jay Goltz, Diana Lee, and Dana White track their financials. It was so good that, this week, in episode 82, we decided to put similar questions to Paul Downs and Laura Zander. “It's funny, I was listening to that episode,” Laura says, “and Diana said she's a freak about the numbers. I'm like, ‘God, does that make me a superfreak?’” Laura walks us through how her labor costs can affect what types of yarn she carries, Paul suggests a quick-and-easy ratio that can signal when a business is in trouble, and Jay explains how an hourly performance indicator that he began tracking 30 years ago transformed his business. Plus: Laura tells us how she got a bank loan that’s almost three times the size of the one she couldn’t get last year.


If you see a story that business owners should know about, hit reply and send me the link. If you got something out of this email, you can click the heart symbol, you can click the comment icon below, and you can share it with a friend. Thanks for reading, everyone. — Loren