When Do You Know You’ve Made It?
On the latest 21 Hats Podcast episode, three owners at very different stages of building a business offer three very different answers.
Good Morning!
Here are today’s highlights:
John Warrillow reminds entrepreneurs that your interests may not align with those of your VC.
A study finds the Inflation Reduction Act has already added more than 100,000 green jobs, many in red states.
The real problem with title inflation is that it makes it harder to attract better talent.
Bay Area startups are looking to reduce the environmental impact of pet food.
THE 21 HATS PODCAST
Walking Away From a Salary: This week, Sarah Segal tells Shawn Busse and Jay Goltz why she’s decided to take her public relations business back after selling it two years ago to a larger firm so it could handle the back-end stuff and allow her to focus on public relations. For Sarah, the immediate result of the decision to break away has been an exhausting few months starting over, including reincorporating, finding health insurance, and reducing her own pay. Meanwhile, Jay suggests an old-school marketing tactic that involves leveraging an envelope, a stamp, and the post office. And Shawn explains how he created a sales process that has allowed him to remove himself from day-to-day sales. Plus, a listener asks the three owners, “When do you know if you've made it? Or do you never know?” Shawn, Jay, and Sarah—three owners at very different stages of building a business—offer three very different answers.
You can subscribe to the 21 Hats Podcast wherever you get podcasts.
MANAGEMENT
John Warrillow asks if it’s worth swinging for the fences when you’d be happy with a bloop single:

MARKETING
Mark Yen started You Need Us Now, a platform that connects micro-influencers with Bay Area restaurants: “The roughly 600 influencers on the platform get exposure, and businesses get a new host of high-quality content to promote their businesses online and, hopefully, an influx of new customers. The ultimate goal is to convert likes and traffic into actual sales and revenue, so You Need Us Now focuses on signing on and vetting influencers who have a bulk of their followers who actually live in the Bay Area. Although the company’s platform is free for influencers, businesses are charged a subscription fee that is tied to the number of campaigns they decide to pursue. Direct sales traffic can be tracked via unique coupon codes, tracking links, or ‘secret menu’ items that are only marketed through influencer channels.”
“‘Part of our role is educating businesses that this type of marketing is not a one-time thing,’ Yen said. ‘One influencer might generate some buzz, but working with multiple people creates a bandwagon effect. It’s like the online version of seeing a long line coming out of a restaurant.’”
“‘Here’s the most important thing to remember,’ [said Vas Kiniris, owner of digital marketing firm NextSF]. ‘The camera always eats first.’” READ MORE
HUMAN RESOURCES
A study finds the Inflation Reduction Act has already added 100,000 green jobs, according to a non-profit advocacy group: “The group monitored press clippings and company announcements to estimate private-sector jobs across a range of sectors that aim to reduce greenhouse gas emissions — including electric vehicle and battery manufacturing, wind and solar energy, and home energy efficiency. The group says its figure is likely a low-ball estimate because it relied on public reports. Climate Power identified more than 90 new clean energy projects in 31 states that have been announced since Biden signed the Inflation Reduction Act, representing a total of nearly $90 billion in new investment.”
“Most of those projects are in seven states: Arizona, Georgia, Michigan, Ohio, South Carolina, Tennessee, and Texas. Georgia has attracted the most investment so far, the group found, with roughly $15 billion worth of projects in the pipeline that are expected to produce close to 17,000 jobs.” READ MORE
Not surprisingly, job title inflation has gotten worse in recent years: “The biggest problem with title inflation isn't confusion — it's that puffed-up titles don't actually attract better talent. In one analysis, Datapeople found that attaching the word ‘senior’ to positions that are actually junior financial analysts results in 39 percent fewer qualified applicants. That's because junior-level candidates see the fancy title and think they're unqualified for the position, while senior-level applicants read the job description and realize they're overqualified. ‘It makes for a very inefficient recruiting process,’ Jahanshahi says. ‘People feel bait-and-switched.’”
“Even worse, the deception leads to a 27 percent plunge in the number of female candidates, making it harder for companies to diversify their workforces.”
“When JobSage, an employer-review site, surveyed workers last year, 58 percent of Gen Z respondents said they expect to be promoted every 18 months, compared with 20 percent of baby boomers and 27 percent of Gen Xers.”
“Gen Z workers also estimated that it takes a mere three to six years to become a vice president. Boomers, by contrast, said becoming a VP requires a decade or more of experience.” READ MORE
21 HATS: LIVE FROM CHICAGO
Join us for the very first 21 Hats Live event: This three-day gathering will be limited to 20 business owners/CEOs. It starts with dinner on Wednesday, May 17, and runs through lunch on Friday, May 19. It will feature lots of opportunities to engage with other owners on similar journeys. We’ll have two deep-dive peer group sessions, for which you’ll help choose the topics. Bring your own challenges! You’ll also get to hang with 21 Hats Podcast regulars including Paul Downs, Jay Goltz, Liz Picarazzi, Sarah Segal, and Dana White. And you’ll participate in the taping of a podcast episode.
Plus: Tour Jay Goltz’s retail operation. Take an architectural cruise on the Chicago River. And make connections that will last a lifetime.
Where: Chicago.
When: May 17-19.
Fee: $2,750. (All meals, activities included. Travel, hotel not included.)
Sign up: Reply to this email with any questions or to reserve your spot.
STARTUPS
In the Bay Area, several startups are trying to make pet food with a smaller carbon pawprint: “Meat produced for human consumption creates a lot of waste from muscles, organs, bones and hides, and pet food traditionally reclaims at least some of those leftovers. And while the zero-waste ‘nose-to-tail’ movement in restaurants conjures up positive images of sustainability, the industrial processing of livestock scraps fails to do likewise. Meanwhile, awareness of the environmental impact of meat production has increased — and in 2018, pet food contributed to 25 percent of that impact, according to the Guardian. It all adds up to more consumers demanding human-grade pet-food products with a lower carbon footprint, or pawprint. The options emerging for pets are as varied as they are for products being developed for human consumption.”
“Founded in 2016 by Anne Carlson, Jiminy's uses cricket protein in its dog food and treats.”
“Founded in 2019 by Caroline Buck and Garrett Wymore, Petaluma makes plant-based dog food.”
“Founded in 2018 by Michael Mitchell and Samarth Bordia, Pezzy uses an invasive fish species to produce its dog and cat treats.” READ MORE
A media analyst, Ken Doctor, is trying to address the local news void: “In the first year after its founding, Doctor and his Lookout Santa Cruz website watched three top editors and the chief revenue officer bail out to other cities; endured an exodus of reporters, some complaining the upstart had not lived up to its lofty goals; and absorbed a broadside from a rival local publisher who invited Doctor to leave town in favor of one of 188 U.S. counties without any newspaper. Many seven-day workweeks and nights of fitful sleep ensued, challenges even more difficult than Doctor acknowledged in his columns about the startup. But the prognosticator-turned-practitioner persisted through what he described as the most difficult challenge of his nearly half-century in the news business.”
“Now, after more than a second full year, Doctor says his fledgling company is on track to make a profit in 2023. If that trend holds, he hopes that his parent company, Lookout Local, can open another website by early 2024, probably in another California city.”
“That would mark a small reversal of fortune in a nation of expanding ‘news deserts,’ communities lacking adequate sources for local news.”
“‘You feel the pressure of time. You feel the pressure of money,’ Doctor said. ‘You only have a certain amount of time to make things work.’” READ MORE
FOOD & BEVERAGE
Just because you can open a Kansas City Chiefs bar in South Philly doesn’t mean you should: “Big Charlie’s Saloon in South Philadelphia seems like a perfect watering hole for watching the Super Bowl on Sunday. It is expected to be packed, but not with Eagles fans. It’s a Kansas City Chiefs bar in a passionate but parochial sports town that doesn’t exactly roll out the red carpet for fans of other N.F.L. teams. ‘We’re in a pickle,’ said Laura Sessa, the manager.”
“If an Eagles fan wanders into Big Charlie’s on any given Sunday, it’s no big deal. But the Super Bowl won’t be any given Sunday. ‘It’s a little tricky now,’ said Sessa, 54.”
“Tickets will be required to enter Big Charlie’s on Super Bowl Sunday. The vast majority will go to regular customers: Kansas City fans. There could be a sprinkling of Eagles fans, friends from the neighborhood, but no one is expected to show disrespect by wearing visible Eagles’ colors.”
“‘I don’t want to instigate anything,’ said Paul Staico, 57, the owner of Big Charlie’s. ‘This city is tough.’” READ MORE
THE 21 HATS PODCAST: DASHBOARD
So You Think Building a Business in the U.S. Is Hard? Well, it is, but after spending a month in London, Gene Marks says inflation, regulation, and entitled employees make it even worse there. In fact, Gene says he’s going to stop complaining about conditions in the U.S. (We’ll see.) Plus: why Gene thinks even small businesses should offer unlimited PTO, how to make sure you don’t fall prey to one of the Employee Retention Tax Credit scams, and Gene’s list of things a small business can do with ChatGPT.
You can subscribe to the 21 Hats Podcast wherever you get podcasts.
Thanks for reading, everyone. — Loren