Highly Recommended Reading: My Year in Startup Hell at Hubspot - Fortune (fortune.com)
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.
 I reassure myself by remembering that HubSpot seems pretty excited about having me come aboard. Cranium (my endearing name for the fellow), the chief marketing officer, or CMO, wrote an article on the HubSpot blog announcing that he had hired me. Tech blogs wrote up the story of the 52-year-old Newsweek journalist leaving the media business to go work for a software company. 

A guy named Zack meets me and tells me he’s sorry Cranium isn’t here today, but he wants to give me a tour around the offices. Zack is in his twenties. He has a friendly smile and gelled hair. He reminds me of the interns at Newsweek, recent college graduates who did background research for the writers. I figure he must be someone’s assistant.
boo04_d-e1458854676968.jpg?quality=80&w=Dan Lyons, a writer for the HBO series Silicon Valley, is a novelist and screenwriter. He is a former editor at “Newsweek. ”Illustration by Jan Feindt

The offices bear a striking resemblance to the Montessori preschool that my kids attended: lots of bright basic colors, plenty of toys, and a nap room with a hammock and soothing palm tree murals on the wall. 

The office-as-playground trend was made famous by Google and has spread like an infection across the tech industry. Work can’t just be work; work has to be fun. HubSpot is divided into “neighborhoods,” each named after a section of Boston: North End, South End, Charlestown. One neighborhood has a set of musical instruments, in case people want to have an impromptu jam session, which Zack says never happens. 

Every neighborhood has little kitchens, with automatic espresso machines, and lounge areas with couches and chalkboard walls where people have written things like “HubSpot = cool” alongside inspirational messages like “There is a reason we have two ears and one mouth. So that we listen twice as much as we speak.”  

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