Don’t Listen to Anna Wintour. Uber’s Customer Service Problem. And Why Bankruptcy Is Getting Easier

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Have you been tempted to take Anna Wintour’s master class in how to be a boss? Save your $90: “The advice was banal (‘Don’t micromanage,’ ‘Be daring and take risks,’ ‘Have a broad range of experience’), and the accompanying PDF workbook is much the same, with 35 pages of leadership and success boilerplate lifted from a corporate-retreat handbook. Wintour opens the series by recounting her morning schedule, the same one that’s been making the rounds since 2007.

“In an attempt to flesh out Anna, the Human, lessons are mixed with anecdotes from her life as Vogue’s leader: an escaped-peacock snafu at the 2007 Met Gala, or the time a businessman told her he loved Vogue because it was elegant, unlike Madonna, whom Wintour later deigned to put on the cover in an act of fashion-world anarchy. The 1989 Madonna cover—as well as 2014’s Kimye cover—is framed as a controversy the editor deftly overcame (‘I think there is always a time you know you have to break the rules’). Other controversies—her mutually advantageous relationship with Harvey Weinstein, or the John Galliano goodwill tour she launched following the designer’s anti-Semitic comments—are not addressed.”

High profile female founders are using Instagram Stories to answer questions from other entrepreneurs: “Trinity Mouzon Wofford, the founder of superfood powder company Golde, answers questions every couple of weeks in video format, which she stores on her Highlights on Instagram. Wofford calls the Q&As ‘Office Hours,’ and says they are hugely popular with her 6,500 followers. The way these founders use Instagram to answer questions from their followers is easy to replicate: When posting a photo or video to Stories, you select a sticker called ‘questions.’ Then instead of asking viewers to answer a specific question, as the app prompts, you solicit questions by typing a variation of ‘Ask me anything!’

“In one recent Mentoring Mondays session, for example, [Katrina] Lake answered questions about how she found her first 50 customers (‘friends and family’) and her tips on public speaking (‘Practice helps a LOT. Take advantage of chances to present whenever you can and ask for feedback’), in addition to offering up advice for maintaining cash flow when declining to work with institutional investors. She doesn’t assume everyone watching actually needs cash-flow pointers; rather she hopes she can show her followers—particularly young womenthat her position is not out of reach.”

 Google is testing a new online forum for business owners: “The service is called Stride (online at It’s a website that invites business owners to ask each other for advice online—how often to communicate with clients, where to look for industrial kitchen gear, which nonprofits make the best partners. There’s nothing on the website that says it’s a Google product. For now, Stride founder Jackie Bernhelm said the company is simply trying to understand what businesses find useful. … Bernhelm, a Google founder in residence, said the company chose to launch its project in Portland because of its high rate of local entrepreneurship, distinctive commercial neighborhoods and civic support for small businesses. … 

“The Google name appears nowhere on the siteshe said it’s isolated from the rest of Google’s products because Stride wants small businesses to experience it on its own terms. Stride said it does identify Google’s role when inviting businesses to participate online or in person. And while Google is notorious for mining personal information and using that data for targeted advertising, the company said it doesn’t use information collected by Stride for any purpose beyond Stride’s core operations. And at this point, Bernhelm said Google hasn’t decided what it will do with Stride. It could become a Google service, spin off into its own company, or morph into something completely different. There’s no advertising on the site, no registration feeand for the moment, no business model.”


A new law should make it easier for businesses to survive bankruptcy: “About a month ago, President Donald Trump signed a new law called the Small Business Reorganization Act of 2019, which will go into effect this February. Its impact on small businesses is expected to be significant … because the new law will give businesses with less than $2,725,625 in debts more time (90 days) to file a reorganization plan with easier rules for extending. Debts will no longer be required to be paid in full for the business owner to retain ownership of a company. Instead, the owner will have to abide by a new formula for payback that projects disposable income over a period of three to five years. There will be less red tape because business owners will now be able to appoint a ‘standing trustee’ instead of a credit committee to oversee their reorganization process. 

“There’s also a new way for determining the owners’ and creditors’ equity interests, based on what is ‘fair and equitable.’ Most significantin my opinionis that it will also be much harder for creditors to take away certain personal assets of the business owner, such as a home or place of residence. Also helping will be an extension of the time period for the payment of administrative expenses.”

Some condo developers are now embracing short-term subletting: “In downtown Nashville, Tenn., developers of a new 77-unit condominium project are explicitly marketing their building to owners interested in renting out their apartments via short-term listing sites. Florida-based property developer Newgard Development Group is expanding a similar model it started two years ago. … These developers are hoping that promoting short-term rentals could make their projects more appealing to buyers and renters and lead to higher profits. They are accelerating the short-term rental industry’s evolution from garages and guesthouses to institutional real estate.

“Airbnb renters in apartment buildings have sometimes run afoul of laws in New York and other big cities that put restrictions on short-term rentals. But Newgard’s new properties in Miami and Austin, Texas, will have hotel licenses. This allows the projects to avoid potential regulatory risks when cities change rules around short-term rentals in traditional residential properties. As a result of the hotel licensing, however, unit buyers at the Austin project will be allowed to live only 30 consecutive days at a time in their own apartments.”


Is Uber’s complaint team primarily interested in protecting Uber? “Inside the 23-story Bank of America Tower in downtown Phoenix, a team of nearly 80 specialized workers grapples with some of the worst incidents that happen in Uber rides. Armed with little more than a phone headset and GPS ride data, these agents in the Special Investigations Unit have to figure out what went wrong. But when they make a determination, the SIU investigators are coached by Uber to act in the company’s interest first, ahead of passenger safety, according to interviews with more than 20 current and former investigators.

“Uber has a three-strikes system, investigators said, but executives have made exceptions to keep drivers on the road. For instance, a New York-area driver allegedly made three separate sexual advances on riders, said an investigator assigned to the case. After an executive overruled the investigator, the driver was allowed to continue working until a fourth incident, when a rider claimed he raped her. The agents are forbidden by Uber from routing allegations to police or from advising victims to seek legal counsel or make their own police reports, even when they get confessions of felonies, said Lilli Flores, a former investigator in Phoenix—a guideline corroborated in interviews with investigators, alleged victims and plaintiffs’ attorneys.”

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YoGov lets Californians outsource their DMV headaches: “Bay Area startup YoGov has carved out a niche by promising customers that it will find them a faster appointment at the DMV and streamline their experience—even wait in line for them—for a fee, of course. Last year, the company created a brief firestorm of controversy when the DMV launched an investigation into the company, but no lawbreaking was found. Now the California State Assembly is trying to pass a bill that would outlaw the sale of DMV appointments, but so far Ryder Pearce, the company’s founder, thinks his company will be just fine. He argues that YoGov isn’t selling appointments; rather, it’s just selling the time it takes to make them.”

Portland-based Big Leaf Networks, which recently raised $21 million, connects small businesses to the cloud: “Bigleaf calls itself a ‘Cloud-first SD-WAN,’ which means it helps companies connect across significant geographic distances, including linking up to data centers and keeping branch offices on larger networks online. Most networking technology caters primarily to large enterprises, Bigleaf says, leaving out smaller companies that depend on cloud-powered business applications but don’t have the IT budget to manage complicated connections.”


The use of facial recognition in public housing units is receiving considerable backlash: “As the software improves and as the price drops, the technology is becoming ubiquitous—on wearable police cameras, in private home security systems and at sporting events. Landlords are considering the technology as a replacement for their tenants’ key fobs, a visual check-in that could double as a general surveillance system. But the backlash has already begun. San Francisco; Somerville, Mass.; and Oakland, Calif., all banned facial recognition software this year. And Congress is taking a look, worried that an unproven technology will ensnare innocent people while diminishing privacy rights. … At this point, the federal government does not regulate facial recognition software in any way, and HUD officials say they have no plans to create any regulations.”


UGG founder Brian Smith realized why his sheepskin boots weren’t selling. His marketing came off as phony: “He raised $20,000 ‘on enthusiasm alone’ from local surf shops and imported 500 pairs of boots to get the company started. In 1979, the company’s first year of sales, UGG sold 28 pairs of boots, for a total of $1,000. The local surf shops didn’t want to carry them because they didn’t fit in with the surfboards, sandals, and other merchandise. … It wasn’t until Smith asked a few 12- and 13-year-old surfer kids what they thought of UGGs that he discovered the reason for his slow sales. They thought UGGs were fake, because the models in Smith’s advertisements clearly couldn’t surf. His target audience wasn’t connecting with the brand, because they thought the marketing was inauthentic.

“So he asked a friend of his to connect him to a couple young surfers, Mike Parsons and Ted Robinson, who were going pro. They went surfing together at Black’s Beach and Trestles, a couple of well-known surfing spots in Southern California. Smith took photos of them walking to and from the surf and ran the photos in ads. Sales spiked to $200,000 that year.”


Recent reports of vaping-related deaths and illnesses, mostly related to THC-based products, are slowing down the growth of cannabis companies: “At Evergreen Organix, the largest producer of edibles, topicals and vapes in Nevada—owned by publicly traded Cannabis One—there’s been a ‘definite slowdown’ in the demand for vaping products, Cannabis One CEO Jeff Mascio told The Post. ‘I think it’s been a knee-jerk reaction, a little too extreme,’ Mascio said of the response to the illnesses, which have resulted in eight deaths. ‘We’ve seen a negative trend against our vaping products since late August, but we’ve also seen our customers move to purchase more edibles and flower products.’”   


Children’s clothing brand Lolly Wolly Doodle, says founder Brandi Temple, was a phenomenon until Facebook changed its algorithm: “I was this great story of an unlikely entrepreneur with no pedigree who was teaching herself as she went along. Everyone thinks that’s amazing when things are going well. But as soon as the wheels fall off, they see someone who doesn’t know what they’re doing. So the board decided to bring in some more seasoned executives. They were right to do that, but they brought in the wrong people, who tried to change the DNA of the business. It was a stable business that was growing, just not as quickly as it had been. But the nature of the VC world is they want home runs and nothing else.”


If it’s not selling, how do you know if it’s a sales problem or a pricing problem? Do star sales people make good sales managers? Loren’s guests on Mind Your Business today will be Lou Mosca, of American Management Services, and Lance Tyson, of the Tyson Group, and they’ll be talking sales Call 844-942-7866 with your questions when the show airs at 1:00 p.m. ET on SiriusXM 132. 

And that’s what’s ahead.

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