I've worked at 6 startups over the last 12+ years as a software engineer, development manager, and software architect. I've worked in DC, Austin, and now the bay area (SF and San Jose). My lowest employee numbers have been 3, 5, and 16 so far!
It's really exciting and I will not go back to working at huge companies. There is a world of difference in what you do, how you interact with coworkers, the impact you have, and the attitudes that permeate company culture. I've never worked without pay, but I have taken equity and/or options with scheduled vesting in exchange for a reduced salary. For example, a developer might make $95k/yr in one job and then go to an early-stage startup and take $70k/yr plus a 2% equity stake in the hopes of the company having a liquidity event (i.e. IPO or being bought out with cash+stock in the new parent company) that nets at least the difference in a few years. For example, if the valuation is $10 million, a 2% stake would be worth $200k.
What you see in the show is mostly at an incubator. I've been at companies that we bootstrapped without an incubator (just straight angel investing at first then series A), a couple that were previously incubated before I came on board (including YC-funded startups), and have worked at one during incubation.
One was post-incubation but, interestingly, the whole office building was dedicated to Chinese-American tech startups. They would get free office space and a small amount of funding for 12-24 months but had to give a board position and equity stake to the incubation organization. They also made them participate in lots of events to demo the product and meet investors and other startup folks. The head of the incubator actually flew some young kids straight out of college to the US and got them an apartment so they could work on their MVP and start meeting SV investors.
At a typical early-stage startup, you bring your own equipment and the company purchases just whatever is needed to fill in critical gaps. So if you're like the guys on the show, you have a badass setup at home and would just use that at first. If you have an office, you would bring it in there. After getting funded (let's assume you did a Series A funding round), you would probably move into a more normal, non-incubator / shared space office. This is around the time that the company matures as a business and starts having signed policy letters, a real consulting accountant, probably swaps around how the corporation is structured, sign stronger NDAs and all that other due-dilligence stuff investors demand. They will also want employees to use company-owned hardware and software so they can ensure they control the IP and can say anything you develop using it is owned by the company.
So, at that time, you'd typically buy everyone some hardware. Since about 2009, I've always been bought a Macbook Pro 15 with all the options maxed out. Sometimes they ask, but often that's just what they hand you because it's fairly standard in web shops. It's also fairly standard to get a second display (at least 27" and usually Thunderbolt). PMs, biz dev guys, and others would get Macbook Airs or similar. At a Windows development shop, they would probably get you a Dell Latitude or XPS and, these days, probably whatever 2k/UHD/4k display was reasonably priced at that moment.
That's what's issued. Many folks have strong preferences of their own and like to work with, say, 3 monitors and a desktop rig. Others like using a laptop stand or dock and having a separate keyboard and mouse or trackpad. Usually the company will accommodate reasonable requests for this stuff or, if you already have it, you can bring in extra displays and whatnot without it becoming company property.
Here's an office in a startup I was at in 2008. We were 2 people per office (no cube farm) and people often brought in tons of stuff to decorate. The desk has a laptop on it from the company and a second monitor but the person eventually brought in a desktop and two more screens from home. He said it was a wall so he wouldn't have to look at me all day, hahaha
Here is my desk view from a couple years ago at the Chinese-American startup (where I was the first non-Chinese person hired!).
And here's a photo they took for a press release of an office I worked at in Austin. This was our new engineering area after we got a final series of funding and hired professional decorators but about a year before IPO. Note everyone has MBP 15s and Thunderbolt 27" displays. I'm in the standup meeting on left far left.
