Launch with a client: Josh left the Academy of Motion Pictures, where he oversaw social media (in the era of the Ellen selfie that broke Twitter), to launch his business. The Academy was his first consulting client.
Niche down: Josh started with a vague help-everyone newsletter. He quickly saw the need to focus on a group of people – creators and entrepreneurs.
Charge for value: Price your content products based on the value they are designed to provide. Define what that value is. For example, if your content helps someone go from point A to point B, you have provided value.
Don’t monetize every content product: Josh uses his I Want to Know as a vehicle to drive conversions to his revenue-generating products.

The Story of Josh Spector

In high school, Josh Spector wanted to be a journalist and attended the University of Maryland with aspirations to cover the basketball team. He was assigned to cover the club field hockey team.

He landed an internship with Capital News Service, covering Congress and the Supreme Court. “I really thought I wanted to be a political reporter, but I hated it,” Josh recalls.

Next, he focused on entertainment journalism. After graduating in 1997, he headed to Los Angeles without a job or contacts in the industry. Eventually, he got a gig at Celebrity Things, a website that combined entertainment reporting with children-focused content.

In the early 2000s, Josh joined Inside.com, an online startup competing against Variety and The Hollywood Reporter. He updated the website with the news each day, which meant staying up past midnight each day.

“This was before [print] publications were regularly updating their websites. They wanted to protect the print version of their content. And we were at the cutting edge of trying to figure out what online journalism could be,” Josh says.

In 2007, Josh got a job at New Line Cinema as a marketing writer. Simultaneously, he started a comedy blog and worked with a partner to produce comedy shows. Josh realized the people, like those at Comedy Central, to whom he was pitching show ideas, read his blog to find new talent. But they didn’t know he was the blog’s author.

“This was a lightbulb moment for me. I realized the internet is a workaround to get to the people who are normally behind the gatekeepers in Hollywood.,” Josh explains.

In 2008, Josh left New Line Cinema as it was folded into Warner Brothers studio. He received two job offers. One from Disney, paying him double and the other from a startup comedy website called Comedy.com, which had only about three months of funding left.

Josh chose Comedy.com.

“I loved comedy, and I loved the internet and online content. It just seemed like more fun. I already knew what it was like to be a marketing writer for a studio and I didn’t want to do that forever,” he explains.

Comedy.com acquired his blog for a minimal amount. Then, Josh recreated what he had done for his blog with their content. It was the hands-on experience of creating content to grow an audience and managing people that he needed.

Launching the first business

In 2011, Josh departed Comedy.com and launched his own business, Connected Comedy, to show other comedians how to use social media and content to grow their audience.

He blogged daily and attracted consulting clients. He assumed most of his clients would come from people he knew in the Los Angeles comedy community. However, his clients came from New York, Australia, and all over the world.

“It really reaffirmed for me that ‘My god, this stuff really works.’ People who have no idea who I am discovered my content, liked what I had to say and wanted to pay me,” Josh says.

An offer too good to pass up

About a year into running Connected Comedy, Josh received a call from his former boss at New Line Cinema, now the chief marketing officer of the Academy of Motion Pictures. She made him an offer too good to refuse.

Josh became the managing director of digital media and marketing for the Oscars for the next five years. When he began, the Oscars had a social media following of 300K across all platforms. Josh and his team grew that audience to over 10M. His team was also responsible for the Ellen selfie at the Oscars ceremony that literally broke Twitter.

“What I realized was that the same strategies I had been using for small-time comedians worked just as well on the biggest entertainment brand in the world,” Josh says.

Launching the second business

Despite the success and lucrative position, Josh still wanted to go out on his own. He started his consulting business to help people grow audiences via content and social media. The Academy was his first client. The deal gave Josh a steady income while working to build his business.

Josh also started a newsletter, For The Interested, with the tagline, “ideas to help you get better at your work, art, and in life.” He published on Sundays.

A few years later, he added a daily one-paragraph edition. As the newsletter evolved, Josh niched down to find his content tilt of helping creators and entrepreneurs use content to get clients. With over 33K subscribers, the newsletter and related social content also lead to most of Josh’s consulting clients.

As he narrowed his tilt, Josh’s client base evolved, too. He went from mostly talent agents to creators and entrepreneurs and now serves mostly established businesses.

Evolving the business

Josh also has refined his offerings. His initial offerings included Skill Sessions and Clarity Calls — designed to provide accessible, actionable insights to creators and entrepreneurs.

Skill Sessions were one-hour, pre-recorded workshops on topics like content creation and audience growth, allowing clients to learn specific skills at their own pace. These affordably priced sessions became popular for their practicality.

Clarity Calls were 90-minute consulting sessions where Josh provided focused advice on a single issue. The goal was to identify and solve a specific problem during the call.

As his business grew, Josh realized these offerings didn’t always lead to lasting results. He needed to work more closely with his clients to develop real content strategy for them.

In 2023, he transitioned to year-long consulting partnerships, working closely with clients to build and execute comprehensive content strategies. These long-term engagements allow Josh to offer deeper, ongoing support, helping clients achieve more sustainable outcomes. He still offers Skill Sessions as a supplemental resource.

Josh also produces a podcast, I Want to Know. The short episodes do a deep dive into a specific topic. He also answers listener’s questions to showcase his expertise. Josh uses the podcast as a marketing tool and has no plans to monetize it.

Advice for content entrepreneurs

Among Josh’s advice for content entrepreneurs in their journey:

Develop a strategy to get clients or customers from your content. Answer this statement that Josh asks his clients: “Tell me about your goals without using the word ‘followers.’” It’s not enough to just build a following. It is easy to get caught up in the details of posting frequency or engagement metrics, but without a clear strategy tied to your business goals, your efforts won’t produce the desired results.
Charge more. Everyone, including Josh, undercharges for the value they create. Stop thinking about pricing in terms of the time it takes to create, and start thinking about the value the content creates for the audience. If you think no one will pay more than $20 a month for a newsletter, think again. What if they paid $20 a month and what they learned helped them land a $10K a month client? The value is clear.

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