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One evening a few months ago, I had dinner at a restaurant in San Francisco called Dirty Habit. It was aptly named. One of my companions that night was a friend from the tech industry – he had studied at Stanford Graduate School of Business and been an executive at a self-driving-car firm before founding his own startup. But as we ate, he flaunted a different sort of achievement: he had lived in the Bay Area for years and never paid for a mattress.

My friend, who asked not to be named, approached this challenge methodically. First he compiled a spreadsheet of all the mattress firms’ free trials and return policies. Then he proceeded to take advantage of them one by one, “buying” six mattresses in turn and returning them just before the deadline, at no extra cost – and getting all his money back. He usually made the switch just before he moved apartments, so he didn’t have to lug a heavy mattress across town. As he described his strategy, I found myself torn between admiration and disgust. His ruse was ingenious, but was creating an Excel file about bedding really the best use of his time?

Taking advantage of promotions is a worldwide phenomenon, but techies stalk deals with extraordinary ingenuity. The perks of the “freeconomy” range from the quotidian to the luxurious. Startups, flush with funding from venture capitalists and eager to grab the attention of new customers, offer free food delivery, prepared meal kits, grocery-shopping, dog-walking, errand-running, moving, laundry and ride-hailing. Some techies boast that they have even figured out how to get free nights on Airbnb and nearly free flights from JetSmarter, which offers on-demand private jets. San Francisco is now more expensive to live in than any other city in America, but the biggest irony of its freeconomy is that the people who are the most adept at exploiting it are the people who need its benefits least: well-to-do nerds with high-paying jobs that come with plenty of benefits.

I used to think I was, if not a freeconomy professional, at least a high-level amateur. Since I moved back to San Francisco, my home town, four years ago, I have learnt the local tradecraft. Locals often use multiple email accounts and different credit cards when signing up for apps so that they appear to be a first-time customer. I play hard to get, wandering away from a service for months only to sprint back as soon as they offer me a coupon. When I need a ride, I play Uber against Lyft to see which ride-hailing service offers the better deal. I’m currently using Lyft: they offered me 25% off ten rides.

I have come to realise, however, that I am nothing but a novice. One popular route to free riches involves a “referral code”, which gives each person who uses it a credit for helping secure new customers. Felix, who runs a startup in San Francisco, has taken this to extremes. He accomplished what he calls his “Bay Area hack” by buying around $600 in advertisements on Google and placing his referral code from Uber in each ad. He spent hours fine-tuning his approach until his ads often had a higher click-through rate than Uber’s own. For each person who signed up to Uber’s service through his ad, he received a credit. He eventually amassed $30,000 in credits, which allowed him to ride around the city in Uber’s cars and eat three meals a day from UberEats, the company’s food-delivery service, for a whole year without paying a cent.

Companies know consumers try to take advantage of them, but some entrepreneurs choose to be wilfully blind to it. “A little bit of you doesn’t want to find out,” says Sean Behr, the boss of Stratim. “You want to believe your product has traction.” His startup, which offers parking services to companies, had to pivot its business away from cheap on-demand valet parking when consumers like me exploited it feverishly.

More: https://www.1843magazine.com/upfront/postcard-from-silicon-valley/how-to-hack-the-freeconomy

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