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Howard Berger’s effort to craft a small business from his expertise and reputation serves as a cautionary tale about the challenges of turning content and clicks into a paycheque, even as digital media expands rapidly.

With the advent of cheap online technology, and a contracting media job market, some journalists have sought to reinvent themselves as independent brands. But fashioning a steady living remains an uphill climb, even for some established personalities.

Case in point: Howard Berger.

The long-time voice of Toronto Maple Leafs reporting for the FAN 590 saw the writing on the wall before the radio station he called home for 23 years cut him loose on June 1, 2011. He planned to reinvent himself as an independent hockey blogger. But a false start on the money-making side of his venture left him defending his tax-loss claims in federal court.

Mr. Berger, 56, covered the Leafs as a radio reporter and self-declared fan for 17 years. Yet his effort to craft a small business from his expertise and reputation serves as a cautionary tale about the challenges of turning content and clicks into a paycheque, even as digital media expands rapidly. He claimed business losses of $26,540 in 2011 and $37,866 in 2012, according to court documents; his gross income from the blog in that span was $7,500.

On June 19, Mr. Berger won his tax appeal – the amounts he claimed were not at issue, but rather whether his blog, titled Berger Bytes, should be considered a business or a personal hobby.

The plan, as described by Mr. Berger and by Justice Campbell Miller, was "simple." Mr. Berger started blogging the same night he lost his job, and soon paid $1,500 to build a more professional site. To stay in the loop and stand out from a multitude of other sports blogs, he kept travelling to Leafs road games. In 18 months, he spent more than $35,000 on flights and car rentals, plus another $23,000 on hotel bills. With next to no money coming in from the blog, he relied on his 21-month severance package from the FAN.

"I really didn't know what my goals were. It happened so quickly," Mr. Berger said in an interview. "I wanted to make sure I stayed in the game."

He viewed the money poured into the venture early on "as essentially a startup cost." Meanwhile, the Leafs struggled mightily, providing plenty of fodder. Even Justice Miller couldn't resist a parenthetical jab: "It is taking immense internal restraint to not comment on the ongoing Leafs 'legacy,'" he writes in his decision.

Mr. Berger e-mailed some 500 hockey contacts, Don Cherry included, to spread the word. In the early stages, his blog typically attracted 3,000 to 4,000 visits in a day, and traffic has "gone up steadily," he said, to more than 10,000 visits most days.

Where some startup news sites have sought support from crowdfunding, Mr. Berger has kept his focus on sponsorships, expecting they would materialize if he grew his blog's following. By the end of 2012, only one had stepped forward: Lawyer Richard Bogoroch paid $7,500 to put his firm's logo on though the 2012 playoffs.

In his judgment, Justice Miller acknowledges a one-man media operation can be expected to start slowly, likening it to "a struggling artist" in their early career. But he remains skeptical of Mr. Berger's long-term prospects.

"Businesses are out to make money and generally have an idea of how much and how feasible the money-making venture is. Mr. Berger does not seem to have a handle on this," Justice Miller writes. "It leaves me to guess whether a steady readership in the few thousands is sufficient to attract sponsors to cover expenses of $30,000-$40,000 a year."

Mr. Berger agrees he could have planned better, but says he's had "numerous discussions" with potential sponsors. His site is considered functional but "ugly," so he expects to launch a redesigned page dubbed Between the Posts in the coming weeks, and is optimistic he will land a major sponsor for the site soon.

Asked whether he now has revenue coming in – beyond inexpensive banner ads supplied by Google AdSense – he replied, "I don't want to talk about that right now," and declined to discuss other projects he has outside sports media.

Four years in, he still writes on the Leafs almost daily, though he can no longer afford to travel to away games. And he says any sports blog should have modest revenue expectations. "It's saturated out there," he said.

But, as jobs go, "it's enjoyable as heck."

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