The 2020 Rebooting Awards

Also a quiz for those thinking of moving to Miami

This is the 12th issue of The Rebooting and the last of the year. I’m not one for predictions, so I went instead with a more lighthearted approach with the first annual TRB Awards and five things I learned this year. Also, after nearly five months living in Miami, I put together a quiz for the Miami-curious so they understand what they’re getting into, and a look ahead at plans for The Rebooting in 2021. Enjoy the well-deserved break.

The Rebooting Awards for 2020

What began as a typical year went awry in March, when 2020 turned into a test of survival. The clawing to get to the other side of this pandemic has done what crises always do: expose the weak, benefit the strong, and accelerate shifts already underway. Here are my awards for the year in media.

Beacon Award: The New York Times

The business turnaround at the New York Times is nothing short of remarkable. It now has over 7 million subscribers and a path to 10 million. That it accomplished this in large part by refocusing and spending on journalism sends a signal to the overall industry to dance with who you brung.

DTC Media brand of the year: Barstool

Dave Portnoy is a singular personality who attracts attention, good and bad, with reckless abandon. Turns out attention is the basis for a good business. The connection Barstool has with its community is unique in media, and its deal with Penn National Gaming shows that media can be the front end for many types of business models.

Exit award: Morning Brew

Morning Brew is a case study in execution. The company nailed its core product of a daily before expanding into verticals and podcasts, and it maintained control and flexibility by not raising tons of capital.

Lifeline award: SPACs

There’s something to be said about hanging around in a game long enough to catch a break. The latest hope for the big VC-funded digital media companies: special-purpose acquisition companies, aka blank-check companies. The craze for them could give a path to the frothy public markets for big digital media, as evidenced by Group Nine’s moves to form a digital media SPAC.

Overhyped trend: Substack Revolution

The phenomenon of star journalists setting up shop on their own will persist, but it will remain a niche phenomenon. The creator economy everywhere has proven to have a middle class problem, and Substack will be likely be no different.

Bright spot amid gloom: Niches

Focused media is the future. Brands built around communities has a leg up in figuring out a workable business model. These models are holding up better with both B2B publications like Industry Dive thriving and big money going into properties like Hodinkee.

Banner ad of the year

Who says nobody ever talks about display ads they saw?

Best media coverage: Ben Smith

Since taking over the media columnist beat in March, the former BuzzFeed editor-in-chief has made it his own, infusing real insidery scoops into a weekly column format and turning it into a must-read every week.

Most complete publication: FT Weekend

The Financial Times does a great job with a weekend paper that covers the gamut of issues and stretched beyond business, finance and politics. Now if only they could deliver to South Florida.

Revenge of the Year: Defector Media

The death of Gawker was a definitive end of a swashbuckling era of independent digital media. That Gawker’s remains were then scooped up by private equity moved the story from tragedy to farce. After an uprising, Deadspin staffers have created a new brand, infused with the Gawker ethos but with a subscription-focused business model that’s attracted 34,000 paid subscriptions.

UX atrocity of the year: Daily Mail

This is a stone-cold mess and unfortunately this dubious award could have gone to dozens of other publishers, including nearly every local news site.

Brands gonna brand award: Humaning

Marketers are easy to poke fun at, with their “learnings” and propensity to spout bullshit while acting like they discovered fire. Mondalez, which makes things like crackers and “dessert solutions,” proudly announced its new global marketing strategy: humaning. How many MBAs did that one take?

Unhinged exit: Glenn Greenwald

The man does not like to be edited, that’s for sure. After co-founding The Intercept, Greenwald lit the place on fire with a find-me-on-Substack diatribe for the annals.

Death foretold award: Quibi

This was never a great idea, never executed well and still attracted TK billion in funding. Kudos for taking a big swing -- and splashing out money to publishers and studios for shows pretty much nobody saw.

5 things I learned this year

Back in early February, I was in Japan for our Digiday Publishing Summit in Kyoto. A mysterious virus was spreading nearby in China. Little did I know our lives would be turned upside down. By the end of the year, I’d leave New York City after two decades, leave Digiday after a decade and get Covid to boot. Quite a year. Here are my own takeaways.

Take the leap. There are always a million reasons not to do something. I was struck by the words of a letter to the editor in the Financial Times in July: “Our lives begin when we tear up the scripts that were handed to us and begin to write our own.”

Stand your ground. Compromise is the only way to get through life. Work, marriage, friendship -- none of it works without compromise. Except principles. Find the hills you’ll die on, but make sure they’re few. Your reputation is the most valuable thing you have.

Know your strength. This year tested all of us. I recall telling the team at Digiday to resolve to come out of this period stronger. Most people are stronger than they think.

Find the opportunity. This crisis certainly reinforced how fortunate I am to have options. We moved to Miami Beach and a new life we never would have considered at the start of the year. Most aren’t that lucky. But in many crises lay the seeds of opportunity.

Actions beat words. Talk is literally cheap. Taking actions involves real commitment and frequently cost as well. That’s why it’s better to focus on what people do versus what they say.

The Miami quiz for the Miami-curious

Improbably, Miami -- home of guac carts and sparklers in desserts -- is being teed up as “the new Silicon Valley,” as Californians and New Yorkers flee the virus, lockdowns, high taxes and whatever else. Miami mayor Francis Suarez is courting the tech and investor crowd with promises of an entrepreneurial paradise. For once, I can claim to be at the vanguard, having relocated to Miami Beach in July. I haven’t regretted the decision once, although NYC is still home to me and will be again next year. Still, for those considering “taking their talents to South Beach,” here’s a quiz to see if you’re ready.

What was the average low temperature in August?

A. 70

B. 75

C. 77

D. 80

2. Which municipality’s mayor was “accidentally” not invited to a Zoom the governor held with all the Miami-Dade mayors to discuss the coronavirus in July?

A. Miami

B. Miami Beach

C. Hialeah

D. Bar Harbor

3. A concerned citizen at a Palm Beach County Commission workshop to discuss a mask mandate declared….

A. “I don’t wear a mask for the same reason I don’t wear underwear: things gotta breathe.”

B. “My face, my choice.”

C. “I didn’t pay $50k for these lips to hide them.”

4. The Miami curfew was suspended after a court case brought by:

A. The state restaurant association

B. Tootsie’s, a strip club

C. The Florida Chamber of Commerce

5. The 2020 hurricane season produced how many named storms?

A. 10

B. 20

C. 30

6. Which is the preferred nickname for Governor Ron DeSantis in the Miami Herald comment section?

A. Death Santis

B. DeSatan

C. ShitStainis

7. South Beach is in Miami

A. True

B. False

8. Sunny Isles, home to several Trump properties, is known as:

A. MAGAville

B. Little Moscow

C. The Redneck Riviera

9. How much rain does Miami get on average per year?

A. 32 inches

B. 42 inches

C. 52 inches

D. 62 inches

10. Which NYC restaurant is not available in Miami?

A. Lucali

B. The Dutch

C. Blue Ribbon Sushi

D. Minetta Tavern

Quiz answers: 1. C, 2. C, 3. A, 4. B, 5. C, 6. A, 7. B, 8. B, 9. D, 10. D

Check out Big Technology

I’ve known Alex Kantrowitz for many years and admired his work as a reporter. In fact, he wrote a few pieces for us when I was at Digiday -- and I tried and failed to hire him when he joined BuzzFeed instead. Alex has a great newsletter, Big Technology, focused on the collision of tech giants and government. Last week, Alex pulled data from LinkedIn to pump the brakes a bit on Miami and Austin as the big winners of the tech talent scramble. The data shows a more nuanced picture -- superstar VC Keith Rabois notwithstanding. Check out Big Technology for more tough but fair coverage of the tech industry in 2021.

Coming up next year

I think of the first three months of The Rebooting as a test period. I plan to continue to evolve the approach, but the central thrust will be on practical knowhow to build sustainable media businesses. My belief is that execution is worth 10x “vision” when it comes to sustainable media. The winners are separated from the losers by the ability to nail the details. Here are some things planned

  • The Rebooting Podcast, launching in the first quarter. I’ll interview those building sustainable media businesses with a focus on problem solving and execution.
  • The Rebooting Circles, also launching in the early part of the year, will be working groups dedicated to specific topics. For instance, I plan to start with a Circle dedicated to solo media practitioners making the move to build sustainable businesses. If you want to participate in this topic -- or others -- please email me.
  • The Rebooting Advisory is a fancy name I’m giving to a handful of consulting projects I plan to take on with media, tech and marketing companies. If you want to work together, please email me.