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TAMPA BAY • FEBRUARY 23-24 2026

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My Year in Startup Hell

Editorial TeamHear the one about the unemployed middle-aged guy who tripped and fell into the new economy?

If you made a movie about a laid-off, sad-sack, fiftysomething guy who is given one big chance to start his career over, the opening scene might begin like this: a Monday morning in April, sunny and cool, with a brisk wind blowing off the Charles River in Cambridge, Mass.  The man—gray hair, unstylishly cut; horn-rimmed glasses; button-down shirt—pulls his Subaru Outback into a parking garage and, palms a little sweaty, grabs his sensible laptop backpack and heads to the front door of a gleaming, renovated historic redbrick building. It is April 15, 2013, and that man is me. I’m heading for my first day of work at HubSpot, the first job I’ve ever had that wasn’t in a newsroom.

HubSpot’s offices occupy several floors of a 19th-century furniture factory that has been transformed into the cliché of what the home of a tech startup should look like: exposed beams, frosted glass, a big atrium, modern art hanging in the lobby. Riding the elevator to the third floor, I feel both nerves and adrenaline. Part of me still can’t believe that I’ve pulled this off. Nine months ago I was unceremoniously dumped from my job at Newsweek magazine in New York. I was terrified that I might never work again. Now I’m about to become a marketing guy at one of the hottest tech startups on the East Coast—a software company that has created an “inbound marketing” platform, which helps companies pull customers in (through blogs, social publishing, and other content), in contrast to outbound marketing (traditional advertising). There is one slight problem: I know nothing about marketing. This didn’t seem like such a big deal when I was going through the interviews and talking these people into hiring me. Now I’m not so sure.

Read more: My Year in Startup Hell at Hubspot – Fortune

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