WeWork's failed $5 million ad campaign, Peloton's brand-positioning deck, and star VC Fred Wilson invests in digital media

Hi! Welcome to the Advertising and Media Insider newsletter. I'm Lauren Johnson, a senior advertising reporter filling in for Lucia this week. If you're new to this email, sign up for your own here. Send me tips or feedback at ljohnson@businessinsider.com.

This week, my colleague Patrick Coffee reported that WeWork was on the brink of spending at least $5 million on advertising just as its finances were collapsing.

• The now-battered coworking company sought out some of the hottest creative agencies - including Wieden and Kennedy, 72andSunny, McCann and Droga5 - to help define its brand.
• When WeWork's flashy initial public offering started falling apart, the review ended. WeWork hired Publicis Groupe Chairman Maurice Levy as interim chief marketing officer, and hired Publicis to oversee its advertising.

WeWork was planning to spend as much as $5 million on a splashy ad campaign even as its own finances were collapsing

Peloton was another startup facing a public-relations crisis, and Patrick also obtained a deck it sent to agencies in May 2018. Key takeaways:

• The fitness company said it's not "snobby," "aggressive," or "a gimmicky fitness brand."
• It wanted to avoid "cheesy ads," which critics say contradicts the company's recent maligned holiday ad.
• Its target customer makes on average $100,000 to $150,000 and up per year.

Peloton's pitch deck shows how the company promised to avoid the 'cheesy ads' that led to its current PR disaster

Lucia spoke to Union Square Ventures' Fred Wilson about why he's investing $5 million in video media startup The Recount and why he thinks now is a good time to invest in digital media even as others are fleeing the sector.

Star venture capitalist Fred Wilson explains why he invested $5 million in video media startup The Recount and how it could quickly become a profitable, $200 million business in seven years

Lucia also reported about martech firm Iterable raising $60 million in Series D funding to compete with cloud giants Adobe and Salesforce. Key points:

• Iterable is one of a handful of martech companies focused on helping brands send messages via email, text messages, in apps and on websites.
• It may face challenges cracking big legacy brands because they're often tied up in multi-year deals with marketing clouds.

Martech company Iterable just raised $60 million in what it calls its last funding round, and plans to use it to take on Salesforce and Oracle and get profitable

Lucia also reported on the year in digital media deals and who will be the winners heading into 2020.

2019 was one of the most tumultuous years in media history, when thousands of jobs were lost and subscription models grew like wildfire

My colleague Ashley Rodriguez talked with Bleacher Report CEO Howard Mittman about his plan to build the digital brand into a sports media powerhouse, including content about legal sports gambling.

Here are the takeaways:

• Bleacher Report wants to woo casual sports gamers as a way to close the gap with competitors including ESPN.
• The brand will become the main digital hub for Turner Sports in 2020.
• Bleacher Report's B/R Betting vertical averages 13.3 million video views per month across platforms.

Inside Bleacher Report's strategy to win over sports gamblers, who it says are 5 times more engaged with its app than other sports fans

Here are other great stories from media, marketing, and advertising. (You can read most of the articles here by subscribing to BI Prime; use promo code AD2PRIME2018 for a free month.)

See WeWork's sweeping newspaper ad campaign, launched in 12 major markets to restore confidence in shaken business

How Vice Media is working to grow its audio production with long-form podcasts and an exclusive deal with Spotify

Omnicom's cultural consultancy Sparks & Honey is launching a new SaaS platform that it claims can help brands weather disruption, and brands like Dairy Management and EA are already using it

How much money a 24-year-old YouTube creator made from 150 million views on a 'Nerf war' video

McDonald's new CEO is tackling the fast-food giant's reputation problem from the inside

Ad holding company WPP closes 2 agencies in its Wunderman Thompson network as the ad industry faces major headwinds

Peloton confirms plans to roll out a cheaper version of its $4,000 treadmill as it looks to replicate the success of its high-tech indoor fitness bike

Broadcasters see big opportunity with podcasts, but risk being disrupted by new players like Gimlet, Wondery

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