I've worked at the two extremes he describes. I've worked for Fortune 250 and 500 companies with cubicle farms and bureaucracy and I've worked for a 2-founder startup with an office overlooking the beach and all glass furniture. Each had its ups and downs. Working for the "Man" meant I was just a cog in an amorphous machine that always made money no matter what I did. Working at a frathouse masquerading as a business, I learned a lot and got free beer every Friday.
Now I'm working for a company in the middle. It was a hip startup in 1998 but has now grown up to be profitable. The older guys are still here, but there is fresh energy too. The company expanded way beyond its original purpose (remember when Amazon only sold books? We're like that), and each vertical feels like a small startup sharing space with other startups. I think it's a good fit for me, but I can't help but think that if I create a startup now, in 10 years I could be the one running a place like this.
Completely off topic, but this is the sort of place I'm looking for now. I've sat in the start up, older dot com, and now in the ginormous corporation but I'm looking for a middle ground. I'd be curious to find out where you work, but I won't pry. Of course, I've been told I should set up shop for myself more than once. I'm just not sure its time yet.
To satisfy your curiosity, I work for Internet Brands. The name change reflects its "grownup-ness" over the past decade since it started off as CarsDirect.com back in 1998. I like that each vertical is like a separate company with a startup feel, but all sharing one big office space.
Since the company started out in an incubator (Idealab), I think they (subconsciously or consciously) kept that incubator feel. For example, when my team is working on a site and we have a vBulletin question, we can walk to the other side of the floor and talk to the people who wrote vBulletin.
Now I'm working for a company in the middle. It was a hip startup in 1998 but has now grown up to be profitable. The older guys are still here, but there is fresh energy too. The company expanded way beyond its original purpose (remember when Amazon only sold books? We're like that), and each vertical feels like a small startup sharing space with other startups. I think it's a good fit for me, but I can't help but think that if I create a startup now, in 10 years I could be the one running a place like this.