Latest podcast episodes
Episode 215: When to Pull the Plug, When to Pull the Trigger
When to Pull the Plug, When to Pull the Trigger
TIME TO LISTEN: 55:57

This week, Mel Gravely, Jennifer Kehrin, and Liz Picarazzi start out talking about the pain of being fired by a long-time client. “It still stings,” says Jennifer, who nonetheless surprised her team by writing a note of congratulations to the CEO of the company that took the business. The conversation moves on to the tradeoff that comes with deciding between promoting managers from within or hiring them from outside the organization: What if your people aren’t ready? What if the outsiders have more experience but aren’t as good a fit? And that leads to a discussion of how to decide when to press on with a venture that’s struggling—and when to give up on it. Not surprisingly, all three owners have some experience in this area. Of course, they also have experience with deciding when to start a business, but they have very different attitudes about risk. While Mel says he’s pretty much always ready to go, Jennifer tells us she’s been noodling on an idea she really wants to pursue for about five years.

Should I Buy the Family Business?
TIME TO LISTEN: 40:56

This week, we bring you another Entrepreneurial Fish Bowl with Chris Hutchinson of Trebuchet Group. As you may remember, this is a virtual exercise where we offer a business owner—or in this case a potential business owner—the opportunity to pose a challenge he or she is facing to a group of owners and entrepreneurs from the 21 Hats community as part of a brainstorming session. In this case, it was BaLeigh Waldrop who explained why she has mixed feelings about taking over the Miller Waldrop furniture business that her parents own. As you’ll hear, BaLeigh has some real concerns: the business has been down of late, it’s predominantly brick-and-mortar, and she would have to work out an ownership structure with a younger brother. The 21 Hats brainstormers some good questions, including whether the business is profitable, whether it’s been paying family members a market wage, and whether it owns the real estate. They also offer a lot of smart suggestions. Plus: it all ends with a very surprising offer from Jay Goltz.

We Have More Work Than We Can Handle
TIME TO LISTEN: 50:01

This week, Paul Downs, Jaci Russo, and Sarah Segal talk about how and when they start planning for next year. And here’s one happy challenge they’ve all confronted: What do they do when they don’t have the capacity to handle all of the work that’s coming their way? Do they staff up? If so, what happens if the work subsequently falls off? Do they create a backlog? Do they miss deadlines? Do they raise prices? Plus: Jaci shares an AI tool she’s been using to learn more about the decision makers her agency targets. And the three owners respond to a case study in ADA-compliance litigation taken from a Reddit post: “What are we supposed to do about this?” a business owner who has been sued for having a non-compliant website writes in the post. “I am trying not to overreact, but having my savings and my income taken from me this way is just devastating.” Jaci, whose agency builds websites, says there is a way to protect against those lawsuits.

Why You Should Run Your Business on EOS (Or Not)
TIME TO LISTEN: 50:23

This week, Shawn Busse, Paul Downs, and Laura Zander call on their own experiences to assess whether the EOS operating system—as explained in Gino Wickman’s book Traction—lives up to its promise of freeing owners from frustration, helping them put the right people in the right seats, and generating all of the scale they want. Laura hired an implementer to install EOS in her business years ago. Paul took more of a do-it-yourself approach, picking and choosing from the book’s suggestions. And Shawn while Shawn hasn’t tried EOS in his own business, he has seen how it works in lots of client businesses. As a result, all three have strong opinions about what types of owners and what types of businesses are likely to do best with EOS. Laura, for example, tells us: “I think it's helpful for people like me 10 years ago, who just don't know what they're doing.”

Is This the Succession Plan For You?

This week, Jay Goltz and special guests Peter Koehler and Jimmy Kalb discuss the hottest new thing in succession planning. You may recall that earlier this year Peter was a guest on an episode in which he explained how he helped Laura Anderson sell her seafood restaurant to what’s known as an employee ownership trust or a perpetual purpose trust. Both Jay and Jimmy listened to that episode and were intrigued. Both had questions for Peter. So we recorded a conversation in which we discuss what makes a business a good candidate for trust ownership. The issues we address include: Is this only for businesses that have a save-the-world type of purpose? How much does it cost to create an ownership trust? Can owners sell to a trust and still run the business as they wish? And perhaps the biggest question of all: What can go wrong?

Never miss a 21 Hats Podcast episode
Best of: Turning a Failing Nut Shop into Nuts.com
TIME TO LISTEN: 51:51

This week, I’m replaying an oldie but goodie, an episode that Shawn Busse and I recorded with Jeff Braverman, who turned his family’s failing retail business into a thriving ecommerce business. I’m replaying this episode both because Jeff has a great story to share, with lots of takeaways, and because—well, actually, because I took a little time off last week. But listen to this: Jeff walked away from a career as an investment banker and went to work in the family’s nut store, the Newark Nut Company. “My dad and my uncle told me I was nuts,” says Jeff, but he made them an offer they couldn’t refuse. He would put the family’s snacks online—this was way back in the early dotcom days—and they wouldn’t have to pay him unless he actually sold some nuts. As it turned out, Jeff’s little internet play wound up unleashing explosive growth and consumed the business. And despite being a former investment banker, he managed to do that without taking any outside capital. Since we first published this episode Jeff has promoted himself from Chief Nut to Chair Nut.

How to SAVE a Customer
TIME TO LISTEN: 42:12

This week, Jay Goltz, Jaci Russo, and Jennifer Kerhin discuss some of the systems they’ve created that have made their businesses successful. Jay established a process that helps employees diffuse conflicts with angry customers. Jaci has a process that tracks the performance of her agency’s lead-generation efforts and has helped her target clients more precisely. And Jennifer recently created a process to deal with change orders that makes it easier to walk the line between offending customers and forfeiting profits. Plus: We follow up on some issues we’ve discussed in previous episodes. Jay told us recently that he’s cutting back on his advertising spend. Is that the best response to a softening market? Jennifer told us when she first joined the podcast about her long march through what is often called the valley of death. Is she still in the valley of death? And Jaci told us at the beginning of the year that she had two big clients that were ready to sign on. Did they in fact sign on?

Can We All Be Purple Cows?
TIME TO LISTEN: 41:41

This week, Shawn Busse, Jaci Russo, and Jay Goltz discuss what it takes to stand out these days, especially if your business—like most businesses—isn’t exactly the Next Big Thing. What about trash collection? What if your business is selling scrap metal? What if you happen to be one of 69 picture framers in Chicago? What’s an owner to do to stand out then? Is it enough to execute really well? Can any business make itself remarkable? Shawn, Jay, and Jaci all believe it’s possible, and they offer examples from their own businesses as well as those they’ve observed. Plus: As Google waffles about whether it’s going to kill cookies on Chrome, will business owners still be able to target customers digitally? And Jay’s not happy about a very big bill he got from his accounting firm. Should he just go ahead and pay it?

Whose Advice Are You Going to Take?
TIME TO LISTEN: 48:45

This week, Paul Downs, Mel Gravely, and Sarah Segal talk about the tricky calculation all entrepreneurs must make between sticking to their vision and accepting advice. Sarah explains why she is reluctant to take advice from people who don’t really know the inner workings of her business, which is pretty much everyone. Paul, on the other hand, says taking advice from outsiders helped save his business during the Great Recession. And Mel talks about why he thinks every business should have a board of advisors—and why he thinks having a board would have saved him from a big mistake he made recently. But then, Paul asks, if you do have a board, can you not take its advice? Plus: Reacting to a recent post on Reddit, the owners discuss the right way to wind down a failing business, a process with which Mel and Paul have some familiarity.

A Silicon Valley Bootstrapper Tells All
TIME TO LISTEN: 1:00:50

This week, special guest Sharon Gillenwater lets us in on some dirty little secrets about Silicon Valley. She is the founder of two businesses. The first one was backed by venture capital and then destroyed by venture capital. Despite that experience, Sharon tried to raise capital for her second business, Boardroom Insiders, a software-as-a-service marketing tool that helps businesses sell to the top decision-makers at big corporations. But this time, the VCs weren’t interested. So she bootstrapped the business with the help of an angel investor—and proceeded to learn some surprising lessons, many of which she shares in her book, Scaling with Soul. Perhaps the biggest surprise came when she sold her business and learned the happy lesson that the founder of a relatively small bootstrapped business can walk away with more money than the founder of a venture-backed business that sells for far more. In our conversation, Sharon is unusually candid about what it took to build her business, what she learned about B2B marketing, and precisely how much money she made along the way.

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