Every year, tech-industry entrepreneurs make a similar decision. Taking on investors is usually one of the first steps in Silicon Valley’s well-established path to outrageous fortune. Merrill wasn’t running a startup per se, but he had plenty of great ideas and ambitions—videogames he wanted to develop, a data backup service he wanted to launch, a whiskey-tasting society he hoped to form. He needed venture capital, but as an ordinary guy, he had limited access to capital markets. That didn’t hold him back. He simply relied on the support of the motley group of programmers, bloggers, and baristas he knew in Portland. It was Silicon Valley–style finance, writ small.

But, like many entrepreneurs before him, Merrill soon learned the downside to taking on outside funding. In the ensuing months and years, 128 people bought shares of Merrill, and he fell victim to competing shareholder interests, stock price manipu­lation, and investors looking for short-term gains at the expense of his long-term well-being. He was overwhelmed by paperwork and blindsided by takeover interest. He found himself beholden to his shareholders in ways he had never imagined, ruining personal relationships along the way. Through it all, Merrill clung stubbornly to the belief that since an IPO had worked for Google and Amazon, it should work for an individual too.

He isn’t alone in this theory. Upstart.com, a company founded last year by Google exec David Girouard, offers a bit of capital in exchange for a cut of a college graduate’s future earnings. Other startups, like Pave and Thrust Fund, solicit investments in entrepreneurs for a return on their future ventures. (And of course David Bowie, European soccer players, and a minor-league baseball player have all sold shares of their earnings.)

But Merrill has taken it further. He felt that more people would invest in him if they knew they were going to have a say over which projects he pursued. To enable this oversight, he paid a developer 500 shares and $500 to build a website that allowed shareholders to vote on his priorities and projects. The developer also coded a trading platform so Merrill’s stock could be bought and sold after the IPO. Anybody could now get a piece of him; you just had to click a Buy button on KmikeyM.com (the site is an abbreviation of Merrill’s full name: Kenneth Michael Merrill).

Initially, shareholders voted on a variety of small projects. On February 15, 2008, for example, Merrill asked whether he should make a short video to market shares in himself. His investors voted that idea down, but a month later they approved an investment of $79.63 in a Rwandan chicken farmer.

The corporate oversight got more complicated in August 2008, when Merrill moved in with shareholder number seven: his girlfriend, Willow McCormick. Though they’d been dating for two and a half years and generally got along great, it wasn’t an easy decision for Merrill. McCormick taught grade school, and her idea of fun was playing Boggle at night with her friends. Merrill couldn’t stand Boggle. He was more interested in things like planning the whiskey-drinking group with his buddies. “His ideal relationship was one in which we lived harmoniously independent lives, and I think mine was a little more traditional,” McCormick says.

Steve Schroeder, one of Merrill’s oldest friends, was upset that he hadn’t been consulted about the move-in. He may not have put much money in—just $139 for 66 shares—but that still gave him 4.8 percent of the voting stock. McCormick had only 19 shares, so technically Schroeder’s opinion should have carried approximately three times as much weight. If Merrill was now going to spend more time at home with his girlfriend, he would have less time to pursue activities that were priorities to shareholders with larger stakes.

Merrill hadn’t intended to give shareholders control over his private life, but he realized that Schroeder had a point. “I figured they’d make good decisions for me, since they had money on the line and wanted to see their investment appreciate,” Merrill says.

McCormick didn’t see it that way. Merrill started spending more time with Schroeder and his other shareholder friends, who jointly controlled a large block of stock. To McCormick, it seemed like a corporate takeover of her boyfriend and gave new resonance to the famous book about corporate buyouts, Barbarians at the Gate. “There were a ­couple of friends I did have some issues with, and they had a big say in how Mike spent his time,” McCormick says. But when she tried to talk to Merrill about it, he would offer what he said was a ­simple solution: “Buy more shares.”

McCormick seethed. “I didn’t want to play into it,” she says. “I felt like my status as a girlfriend earned me his ear, like the way a first lady has the president’s ear.”

When they started dating, McCormick and Merrill had a series of conversations about whether Merrill should get a vasectomy. At first they agreed that it was a good idea; neither thought they wanted kids. But now that she was a ­little older, McCormick wasn’t so sure. “I started to have stirrings,” she says. “I was feeling less certain.”

Then, on August 10, 2008, Merrill asked the shareholders to decide whether he should get a vasectomy. He didn’t tell McCormick that he was going to bring them in on it. As the CEO of himself, he simply wrote a note to his shareholders explaining his position on the subject. “Children are a financial drain,” Merrill wrote. “The time investment of raising a child is immense. The responsibility is epic. The impact on future projects would be drastic. In light of these factors, it makes sense to reduce the chances to nearly zero and have a vasectomy performed.”

McCormick was furious and embarrassed. “He made our personal life public without consulting me,” she says. It got worse when the ballots came in. Schroeder voted yes. Josh Berezin, a grade-school friend and political consultant, voted yes. To McCormick, it wasn’t just a referendum on the vasectomy. It was also a referendum on whether Merrill’s friends thought he should have kids with her. It was, she says, “a judgment on me.”

It wouldn’t be the first time that outside investors tore apart a close relationship among a company’s principals. For recent ­examples, look no further than Eduardo Saverin, Mark Zuckerberg’s onetime pal who was pushed out of the company he helped found. And like Saverin, McCormick decided to fight back.

Data current as of March 22, 2013

The first candidate was a cute 28-year-old administrative assistant named Marijke Dixon (code name: Agassi Dakota). Merrill invited her out for a glass of sparkling wine and then to see an obscure Norwegian thriller. In his report, he noted that she was squeamish during some of the movie’s more violent moments. “Since this is the first date I’ve been on since we started this project I’m not sure what sort of information the shareholders need to make an evaluation,” he wrote. “So please leave questions, and I’ll do my best to answer them.”

The investors asked if they got a drink after the film (no), what he thought of the movie (so-so), and if he was attracted to her (“Yes, I am!”). Shareholder approval hovered around 60 percent.

For her part, Dixon was into Merrill. “I tend to date ­weirdos,” she says. She also thought it would be an interesting challenge to win over not just Merrill but all of his shareholders. She decided to start accumulating shares so she could influence decisionmaking, initially buying 50 shares for $90. “I would have bought more, but I’d just moved into a new apartment and was short on cash.” In a modest way, she was launching the equivalent of a corporate takeover, though it was unclear yet if she was planning a merger or an acquisition.

But some shareholders had other ideas. One anonymous investor sent Merrill on a date with a polyamorous woman. “She is currently seeing someone, but she has permission to date,” he wrote in his after-action report. “I’m of mixed feeling about that, but I recognize that this is a decision for the shareholders to make.” They decided against continuing the relationship but gave a 97 percent approval rating to a guy referred to as Jordon California. Feeling the weight of investor expectations, Merrill spent a drunken night “fooling around” with him. Like companies that stray from their core business to pursue an ill-advised acquisition (AOL/Time Warner, eBay/Skype), Merrill was slightly hung over the next morning—and only more convinced that Dixon was the one.

In an effort to sway his overseers, Merrill described his growing feelings for Dixon in subsequent date reports. He highlighted what he liked about her, from her piano playing to her impressive knowledge of financial markets. “This is a very strong candidate,” he wrote. Her approval climbed to match that of Jordon California, and Merrill decided that management could break the tie. He chose Dixon, and they signed a three-month relationship contract.

Dixon was excited. She liked Merrill, but she also liked the idea of accumulating shares of him. So when the three-month term was up, she asked for a sweetener: She wanted stock options this time. The proposal made sense to Merrill; Silicon Valley companies often use stock options as a way to reward people involved in an enterprise and strengthen their loyalty. The more shares Dixon acquired, the more investment she’d have in the success of the relationship. Merrill agreed to award her 100 options in their next contract. The strike price—the price of the shares at the time the option is exercised—would be pegged at 5 pm on the day the contract was ratified by shareholders.

On the afternoon of ratification day, Dixon deliberately sold a share for 99 cents in an effort to game the market and set the strike price artificially low. Another investor caught on to the ruse and fired back by buying a share at $12. But, at 4:59 pm, Dixon managed to scoop up a share for $1.52. The clock hit 5, and she locked in a paper profit of roughly $900.

Merrill was touched. To him it was a romantic gesture. None of his projects had yet flourished or paid dividends (the Rwandan chicken farmer had run off with the $79.63), and yet Dixon believed in him enough to try to accumulate as many shares as pos­sible. “Instead of getting me flowers, she was trying to buy me,” Merrill says. “It bodes well.”