What it takes to run a business

Podcast

Almost every growing business experiences a moment when success starts creating as many problems as it solves. Sales are up. The team is bigger. The product line is broader. And suddenly, the systems that got you here start to break. That’s where Liz Picarazzi finds herself right now. “We’re in the valley of death,” she says. “And we really need help.” Liz’s company, Citibin, made the most recent Inc. 5000 list, but Citibin has also hit that dangerous in-between stage—too big to run on improvisation, too small to have put in place all of the processes it needs.

So Liz is trying to grow her way out of the valley. She’s hired a marketing agency. A growth consultant. And two AI advisors. She’s testing new domestic fabricators. And she’s rebuilding her website from the ground up—because right now, it’s generating no more than 10 percent of sales, and she knows it can do better. The site hasn’t kept up with her expanding product line, and it isn’t even optimized for search engine discovery, let alone for generative AI discovery.

Talking it through with Paul Downs and Jaci Russo, Liz confronts some uncomfortable questions: How much copy is “enough” for AI? How transparent should pricing be—especially for a premium product whose prices could scare away some customers? And who has a better feel for the company’s story—the owner who’s lived it or the agency that has more experience helping businesses connect with customers? Not surprisingly, Liz and Jaci have different instincts on that one. What follows is a candid look at what it takes to rebuild a growing business at the dawn of a new era.

Alan Pentz is convinced a wave of disruption is about to crash into small businesses—and he’s doing everything he can to warn owners before it hits. He’s writing, teaching, consulting, waving the red flag. He’s just not sure anyone is ready to listen. “I don’t know if you’ve seen 'Don’t Look Up,'” he says, “but it’s kind of like that. The asteroid’s coming—and everyone’s still walking around like it’s normal.” In our latest 21 Hats Brainstorm, Alan put his own future on the table. He asked a panel of owners to help him answer a hard question: Do business owners actually want help adopting AI? And if they do, what kind of help will they pay for? Is there a real, scalable business here—or just a lot of interest and polite nodding? And there’s one more twist: Alan already owns a successful consulting firm. So he also has to decide whether this opportunity is worth jumping back into the startup grind to build another service-heavy business from scratch. The Brainstorm is brought to you by New Bridge Studios, which helps companies, creators, and causes connect their stories to the bottom line.

Things are suddenly moving fast at Sarah Segal’s San Francisco PR firm. Several new clients look likely to sign on, and for the first time in a while, growth feels real. Which leaves Sarah with a familiar, nerve-racking question: Do you hire before the work arrives—or wait until the revenue is actually in the door? If she hires now, she may have to cut her own pay until the new business materializes. And there’s no guarantee it will. She still remembers the last downturn, when she had to lay off people she cared about—and she’s determined not to repeat that experience. But if she waits and the clients do sign, she risks something else: overloading her existing team, burning people out, and falling behind before she can recruit and train new hires. The pressure is even higher because Sarah has already set an aggressive revenue goal for 2026.

Plus: Jaci Russo explains why she’s adopted a different approach to planning and budgeting. Instead of guessing how much she can afford to spend, Jaci is changing the order of the math. After revisiting Mike Michalowicz’s Profit First—prompted by a story highlighted in the 21 Hats Morning Report—she’s begun setting profit targets first and forcing every other decision, including hiring, to fit around them. It’s only been a few weeks, but Jaci says the shift is already changing how she thinks about risk, growth, and what she can actually afford.

Six years ago, Kate Morgan walked away from the sale of her business just days before closing. Since then, she’s endured some rough stretches, fighting through the pandemic and a slump in the software sector where many of her clients live. She’s managed to stay profitable, and she sees lots of opportunity ahead, but the grind has worn her down. After years of pushing, adapting, and holding on, she says she’s had enough. She believes a strategic sale makes the most sense, and she’s working her network to find the right buyer. This week, she talks through her plan with David C. Barnett and Ted Wolf, two owners who—unlike most—have actually sold businesses and lived with the consequences. They push Kate to think carefully about her options and the pitfalls that trip up so many owners.

Plus: One reason Kate is ready to sell is that she’s recently published a book, and she’d like to devote more time and energy to accepting speaking opportunities. As it happens, Ted has written two books that he’s trying to figure out how to get published. Kate and David compare notes on the very different paths they’ve taken—David self-publishing through Amazon, Kate paying a big fee to work with Forbes Books. Both are quite happy with the choices they made.

Most business owners say they want balance in their lives. They tell themselves they just need to get through this one crisis, this one launch, this one quarter—and then life will settle down. But what if that’s not actually the goal? This week, Mel Gravely, Lena McGuire, and Ted Wolf talk candidly about what it really takes to build a business—and about whether balance is something owners are truly striving for or simply something they feel they’re supposed to want. “I gotta tell you,” says Mel, “I just don't know if people were really honest that they'd say that they'd be one to spend their time at their kid’s parent-teacher conference.” Lena stresses that it’s not about right or wrong. It’s about owners making the choice that’s right for them. “You have to make yourself happy first,” she says. “It’s kind of—we always use that, ‘Put your oxygen mask on yourself first, and then you can help others.’” The owners agree that there’s a seasonality to entrepreneurship. There are periods when the business demands more, and owners have few real options. That pressure can intensify when a company is struggling—but, intriguingly, it can be just as intense when the business is growing fast. Of course, all businesses endure periods of crisis. But what if the crises never end?