Josh Topolsky cofounded The ésuméVergeand helped launch what is now known as Vox Media, which has grown into one of the most successful digital media companies around.
That's the kind of résumé that opened doors when Topolsky went looking for investors for his new venture. He's just one of a group of entrepreneurs that have been able to raise early rounds of funding for media startups just months after a mild panic swept through the industry.
Topolsky ended up raising $5 million for The Outline, his new digital media publication that will cover power, culture and the future. Despite the strength of his résumé, the open doors didn't immediately lead to signed checks.
"The experience was largely bad," Topolsky said about his fundraising efforts. "The vision that you need to think about and talk about when you think about these new media companies is in some ways in direct opposition to what investors typically want to hear."
If venture capitalists are cooling on media startups, there appears to still be an appetite to invest in founders that have already demonstrated an ability to start successful online operations.
Among them:
Arianna Huffington's new project Thrive recently brought in $7 million.
Jim VandeHei raised $10 million for his first project since leaving Politico, the media company he cofounded.
Former BuzzFeedCOO and president Jon Steinberg raised $10 million for Cheddar, his business-focused media startup targeted at a younger audience. It's the company's second major round.
Bill Simmons started The Ringerearlier this year with undisclosed backing from HBO after having launched Grantlandat ESPN.
"I wasn't surprised to see it," said Dan O'Keefe, general partner at venture capital firm Technology Crossover Ventures, of the recent investments. "Those are not brand new entrepreneurs trying to do things for the first time. Those are people who have had pretty significant success in reinventing the media model."
Just what that model will be remains up for debate. Digital media had once relied on the venture-friendly notion of reaching billions of people around the world. Newer entrants are now scaling back those expectations, an idea that Topolsky found wasn't entirely welcome among the venture crowd.
"Right now, media isn't necessarily about fixing the algorithm or having some kind of crazy new magic technology that changes everything," Topolsky said. "It's great to be Big Bang Theoryor American Idol, but you also want Breaking Bad, you want Mad Men. You want what HBO does, so it's about finding levels of audiences that aren't being well served right now."
Jon Steinberg served as president and chief operating officer for BuzzFeedfor two years, then moved over to the CEO seat at the Daily Mail's U.S. equivalent for another 19 months. So when he looks for financial backers, he can find them.
Steinberg didn't mince words about why he was able to raise his first round of funding. His second round, however, he said was about results.
"My first round of financing from Jeremy [Liew] and Lightspeed [Ventures] was 100 percent a bet on me. We had no product. We were pre-launch," Steinberg said.
Since then, Cheddar has launched its live, daily show from the floor of the New York Stock Exchange, opened a subscription program and even announced a partnership to stream live on Twitter.
Those are the developments that Steinberg said attracted its most recent round of investment. His pitch centers on Cheddar being well positioned to take advantage of the demographic shift of young people moving away from traditional television and toward an over-the-top, internet-based future.
But its $6.99-per-month subscription service isn't necessarily for everyone, a stark difference from Steinberg's former company. Within a decade of launching, BuzzFeedclaimed to be reaching 18 billion impressions per month across its social channels. Suddenly, media companies could scale like tech companies.
How would those companies make money? Who cares. The venture capital strategy of reaching billions first and making money off them later was good enough for, well, venture capitalists, who plowed tens of millions into companies like BuzzFeed, Refinery29, Mic, Upworthyand Mashable.
Growth continued thanks to things like Facebook's embrace of video, but making money off this reach remained elusive. BuzzFeedreportedly missed its 2015 revenue target and slashed its 2016 revenue goals. Mashablewent through its own reorganization. Layoffs have hit a raft of other digital media entrants.
Jessica Lessin, journalist and founder of The Information, a tech-focused subscription news startup that charges its customers $399 per year, recently wrote about this group of new entrants. She is among a growing group that believe the growth-first, profit-later model that usually accompanies venture capital is bad for the news industry.
"You could read these announcements as a sign that VCs are bullish about the news business," Lessin wrote. "I see them as a sign that the news industry is still very much on the wrong track."
Even the most successful new media companies are trying to figure out their way forward. Vice CEO Shane Smith recently said the company was still torn between going public or being acquired. Most successful startups continue to run on later-round cash investments from legacy media companies, arrangements that can lead to an outright acquisition. Smith also predicted a "bloodbath" among old and new media companies alike.
Steinberg said the difference between BuzzFeedand Cheddar is entirely on purpose.
"I do think there's an enormous danger in doing things the same the second time around," Steinberg said.
This question remains: Why would investors see media companies that aren't trying to take over the world as a worthwhile place for their money?
O'Keefe, whose Technology Crossover Ventures invested $250 million in Vice in 2014, said that media companies don't necessarily need to conquer the world like a tech company, thanks to plenty of legacy media companies looking to make sure they're prepared for the future.
"There's an incredible amount of entrenched interests," O'Keefe said. "They're all trying to figure out how to continue to reinvent themselves for an entirely digital age."
Name the traditional media company and chances are they have made major investments in digital media companies. Those investments may have cooled most recently, but that didn't stop Refinery29 from taking a $45 million round from Turner and Scripps in early August at a valuation of $500 million.
"From a funder's perspective, from an investor's perspective, absolutely you want to invest in something that will have multiple paths and optionality over time, and I do think that's the case with media companies" O'Keefe said. "I think 2016 will go down as the year of the [mergers and acquisitions] exit, not the IPO exit."
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