21 Hats Podcast

This week we focused on Laura’s struggle to get control of a Texas-based yarn supplier that she acquired late last year. She’s had issues with inventory, personnel, quality control, and then the general manager walked out, which has Laura feeling deflated knowing that some employees are talking about her and some just don’t like her: “I really struggle with that. Am I the only one who struggles wi...

Before the crisis hit, Jay, Dana, and William talked about what they thought the next recession might mean for their business and the benefits of starting a business during a recession: “What I've learned is, when things go bad and I lose $300,000 and I take out a second mortgage on my house, no one comes into my office and says, ‘Hey, boss, can I give you some money?’” Plus: Some making tough dec...

In this week’s report from the front lines of the crisis, we talked about overcoming the fear of raising prices (during a pandemic!), deciding when is the time to tell employees they have to come back if they want their jobs, and finding opportunities amid the crisis disruption. But the focal point of the conversation was Dana White discussing her realization that she’s been more productive during...

Karen, Jay, and Laura talk about dealing with questions they’ve never faced before: Is it safe to fly again? What do you do if you run out of inventory and can’t get more? How do you entice employees back into the office who’ve either been happy working from home or happy collecting enhanced unemployment? Do you offer hazard pay? And if so, how and when will you stop? “We're trying to stay in busi...

Jay, Dana, and Laura talk about the process of reopening—the precautions, the risks, the consumers who might not show up, the dilemma of asking employees to accept less in pay than they were getting in unemployment, and the possibility of a second coronavirus wave that could bring a second shutdown: “I don't have the luxury of just saying, ‘Oh, I'll tell you what. Maybe we'll open in six weeks, ei...

Karen, Dana, and Laura share their experiences building businesses as women entrepreneurs: “It's like, ‘Well, you can tell me I can't do this, but it looks like I did.’” Plus: Has the legalization of recreational cannabis had an impact on your business?

Karen, William, and Dana talk about why some businesses got the Paycheck Protection Program loans and why some didn’t: “The independent grocers. The hair salons. The small restaurants. They didn't get the money,” says Dana. “I have a staff who are single mothers, single black mothers, who are hard-working and who didn't have the foundation to go to college and are doing what they can. I'm up every...

Jay, William, and Laura talk about the status of their CARES Act loans, and to everyone’s surprise (including his own), William reveals not only that his Paycheck Protection Program loan has been approved, but he’s already got the cash. Was it divine intervention? Plus: Jay offers up a stress test for businesses in crisis—five ways to assess whether your company is positioned to survive.

Jay, William, and Dana talk about their prospects for landing a Paycheck Protection Program loan, what they think business will be like when shelter-at-home ends, and why they decided to lay off people even though they expect to get forgivable loans: “The bottom line: we cut 40 percent of our payroll yesterday. My decision was, I would rather cut deeper, fewer times. So I'm going to do this once.”...

William, Dana, and Laura and their businesses are having very different coronavirus experiences. While Dana and William are expecting little in the way of revenue, Laura’s online yarn business is thriving. But they’re all facing challenges in managing their employees: “It's been amazing to see just how hard folks are working. Are they concerned about a layoff? I'm sure they are. I would be too.” P...

Karen, Jay, and Laura talk about painful layoffs, maintaining morale, and hunkering down during COVID-19: “We've been having a meeting for the last two or three days about, ‘Okay, we have X number of dollars in inventory. Can we pull a couple hundred thousand dollars out of inventory in case we end up being cash flow negative for the next two months?’” Plus: finding ways to help other struggling b...

Karen, Jay, and Dana talk about the contingency plans they’re making as we head into the health and economic crises presented by COVID-19. Can they keep paying hourly workers? Can they keep their locations open? Can they find the resolve to hang on no matter where this goes? “You're gonna get through this. You're gonna do what you need to do. If you need to close the one salon, so be it. And you'r...

Nobody goes into business because they think they're going to be really good at firing people. When you read books or magazine profiles of business leaders, you rarely hear anyone say, “You know, the one thing I've really mastered is knowing when and how to fire people.” And yet it’s something that every entrepreneur has to deal with. Even at the most successful businesses, some employees are not...

In Part 2 of our special taping in front of a live audience at Blink UX’s headquarters in Seattle, Brian Canlis talks about how he and his brother took over the family restaurant and what happened when they decided to modernize its operation: “We did lose 10,000 guests that year. And we lost money for the first time as a company ever that year. And we got three negative reviews in the paper. And w...

In a quick update, Karen, Jay, and Dana talk about how the coronavirus pandemic has already affected their businesses and how they are planning for the future.

In this special taping in front of a live audience at Blink UX’s headquarters in Seattle, Karen, Jay, Dana, and Laura talk about the risks of fast growth and why they haven’t taken investment capital. “I was so focused on growing that I kind of blew it up. I blew the whole business up by hiring people who we weren't ready to hire for. We were probably doing $5, $6, $7 million dollars in sales. I d...

Karen, William, and Laura discuss taking investment capital, dealing with stress, and why Karen’s going on sabbatical: “I just thought, ‘Okay, okay, I'll go.’ Then of course, I'm worried, like, ‘What if everything goes better without me?’” Plus: how are you managing health insurance costs?

Jay, William, and Laura discuss whether a great culture produces a successful business or whether a successful business produces a great culture. Do you think of your employees as family? Do you have anyone working for you whom, if you had it to do over, you wouldn’t hire? Plus: do you manage your Glassdoor page?

Jay, Dana, and Laura talk about risking it all, figuring out digital marketing, and connecting with your target audience: “Right now, my market is predominantly African American, but we have a lot of redheads. We have a lot of women of Indian and Middle Eastern descent.” Plus: how do you know if franchising makes sense for your business?

Jay, Karen, and Laura talk about competing on the internet, buying a supplier, and whether to take venture capital: “Who needs to answer to somebody if you don't have to?” Plus: after the Domino’s decision, what happens if your website isn’t disability compliant?

Loren and Karen talk with four of EY’s Entrepreneurial Winning Women about opening the books, bootstrapping a tech company, selling a business for more than $100 million, competing with Amazon, hiring hard-to-get talent, and pitching investors: “I've always said, ‘I'd rather be 75 percent of a watermelon than 100 percent of a grape.’” Plus: how much of your life do you have to sacrifice to be succ...

Jay, Karen, and William talk about pricing, custom manufacturing, and content marketing: “There have been people who would have been very good at a job, but they aren't willing to or able to put together content, and that just doesn't work for us.” Plus: the SEO value of an unusual last name.

Karen, William, and Laura talk about being a bad CFO, dealing with a disappointing profit margin, and the true price of growth: “I think our commitment to being cash-based and debt-free has been more important to me than the big number at the end of the year.” Plus: hiring employees vs. hiring contractors.