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I don't think they had issues making money, they had issues hitting unrealistic growth targets being set by their overlords. This was discussed on the most recent Nextlander podcast. Nextlander being 3 of the Giant Bomb OGs.

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No issues making money once they were up and running, but they needed to bootstrap somehow and therefore weren’t just owned by Jeff G from the start

Jeff Gerstmann, one of the founders, also goes into details about this, Giantbomb was always making money, but had issues scaling up because corporate wouldn't invest in them. He says that it was very hard for them to monetize the podcast, which was one of the biggest podcasts before the boom, because they wouldn't allow him to sign a deal with a ad network, nor would they provide a sales team so they could get those ad deals.

CBS also owning Gamespot was a big issue, because it wasn't making money but it had the potential of bringing much more if they could fix it. It got even worse with the last 2 rounds of buyouts, because the buyers never wanted Giantbomb, it was a package deal.

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