What it takes to run a business

Podcast

This week, we welcome a new regular to the podcast team, Rob Levin, co-founder of WorkBetterNow. I first met Rob more than 20 years ago, when we were both experiencing the decline of print media. I was an editor at Inc. magazine, and Rob had started a regional publication for business owners called The New York Enterprise Report. “Starting a print publication in 2003 was not one of the smartest things I've done,” Rob says. But he learned from that experience. In 2018, Rob and a partner started WorkBetterNow, which helps American businesses hire Latin American talent. The business took off during the pandemic and has continued to grow rapidly. But in recent years, Rob began to see another disruption looming. If artificial intelligence can increasingly perform the kinds of tasks his company supplies people to do, what happens to WorkBetterNow?

Rob tells Sarah Segal and Jaci Russo how seriously he took that question, what he decided his company needed to become, and how he’s trying to position WorkBetterNow for whatever comes next. We also talk about why referrals are no longer enough to sustain the company’s growth, what went wrong when Rob tried to build an outside sales force, and what he’s learned about managing remote workers. Plus, in another Beyond Small segment brought to you by Grasshopper Bank, Sarah, Jaci, and Rob compare how they manage the cash they keep on hand—and Jaci explains why she’s sleeping better since adopting Profit First earlier this year.

This week, Paul Downs, Jaci Russo, and Sarah Segal revisit a question that came up on the podcast more than a year ago: Is artificial intelligence going to doom professional service firms like Jaci’s branding agency and Sarah’s PR firm? So far, both Jaci and Sarah are feeling pretty good about their prospects. In fact, they’re seeing changes in the market that suggest AI may be helping rather than undermining their businesses. Paul, meanwhile, has encountered a different kind of AI mystery. For years, his custom conference table business has depended heavily on people finding him through Google. Recently, he discovered that his organic search traffic has fallen about 35 percent. That sounds alarming—except that his business is doing great. Paul says his tables are selling like “hotcakes,” and he’s backlogged into February. So what exactly is happening when traffic falls but sales keep growing?

Plus: In our latest Beyond Small segment, sponsored by Grasshopper Bank, Paul, Jaci, and Sarah talk about the financial processes they still insist on doing manually—even when technology could probably do more of the work for them. In each case, part of the reason is that doing the work themselves gives them a view into their operations that they don’t want to lose. As Sarah puts it, while she already knows how to handle public relations, “I am learning how to be a business owner every day.”

This week, Jay Goltz and William Vanderbloemen tackle a problem that business owners may associate with big companies: What happens when an employee becomes convinced that his or her manager is making bad decisions, but going through normal channels just isn’t working? Jay says he absolutely wants employees to speak up, even if that means going over a manager’s head. William agrees that there are times when an employee has to escalate a problem. But as the conversation unfolds, both acknowledge something that can be easy for an owner to underestimate: Speaking up can feel extraordinarily risky to employees. And how is that information going to surface then?

And in our latest Beyond Small segment, Jay and William discuss what, if anything, another bank could offer that would persuade them to move their business—and why both have grown wary of what happens when smaller banks get swallowed by bigger banks. Plus: How should owners think about the forecast of a prominent economics group that a severe downturn is likely to hit in 2030? And William talks about how his wife’s cancer diagnosis has changed the way he thinks about time, work, and succession. As one of his older golf partners put it, life is like a roll of toilet paper: “It goes really fast at the end.”

Earlier this year, Ted Wolf suggested that Paul Downs should take a serious look at how artificial intelligence might improve his custom woodworking business. Paul was skeptical—but he invited Ted and his team to come visit the shop and see for themselves. This week, Ted reports back. He came away impressed by the business Paul has built but also convinced that Paul has a problem: As Ted sees it, too much of what makes the company work still resides in Paul’s head. Ted believes AI could help capture some of that knowledge, improve everything from estimating to production, and, perhaps most important, prepare the company to run one day without Paul.

Paul remains unconvinced. He agrees that AI will find its way into the business eventually, but he questions whether it can capture the judgment, experience, and nuance required to build one-of-a-kind products. His inclination is to let the next owners figure that out. “So Paul,” Ted responds, “if they’re going to have to deal with it, you just lowered the value of your company.” Which raises a question that goes well beyond AI: If you hope someday to sell or transfer your business, how much of what you know has to be captured before you leave?

Plus: In our latest Beyond Small segment, sponsored by Grasshopper Bank, I ask Paul, Ted, and Lena McGuire what would happen if their businesses suddenly doubled. Would they be thrilled—or terrified? Could they handle the growth? And would they even want it? That leads to a discussion that comes up here fairly often: How big do you really want your business to be?

This week, Jaci Russo, Liz Picarazzi, and David C. Barnett talk about something entrepreneurs are always being told they have to do: innovate. But how do you know which ideas are worth pursuing, how much time and money to put into them, and when an experiment starts to become something much bigger? Jaci Russo may be finding out. What started as a prospecting system she built for herself—with AI, verified data, and a simple CRM—has turned into ProspectDaily, a subscription product that attracted more than 100 customers before she even announced it. That has Jaci thinking the tool could do more than generate a little extra revenue. As AI makes it easier for clients to do more of their own marketing, she sees ProspectDaily deepening client relationships and ultimately changing the nature of her business. So far, she says, the hard costs of creating the tool amount to $185. (Try ProspectDaily for free.)

Liz, meanwhile, is spending $10,000 this year testing whether old New York City trash cans and other recycled plastics can be turned into a new cladding material for Citibin. And she’s itching to spend another $30,000 on the equipment to manufacture the material once she determines whether customers actually want it. Both Liz and Jaci kept their projects quiet early on. As Liz explains, “I have so many ideas all the time. I didn't want there to be eye-rolling, ‘Oh, here's another of her things.’"

Plus: In our latest Beyond Small segment, brought to you by Grasshopper Bank, the owners compare how closely they watch their numbers, which metrics matter most, and whether spending time on financials gets in the way of doing the work they really want to do—like coming up with new products.