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Markus Frind built the largest dating site in the world by himself, ran it on about an hour a day and sold it for $575 million to a single shareholder. Then he bought more than 1,100 acres in the Okanagan and went back to farming.
Markus Frind built the largest dating site in the world by himself, ran it on about an hour a day and sold it for $575 million to a single shareholder. Then he bought more than 1,100 acres in the Okanagan and went back to farming.
Featuring: Markus Frind, Annie Frind, Kevin Burton, Frank Giustra, Lady Gaga
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Chapters:
(00:00) The French Riviera, and a business running without him
(00:27) Donauwörth to Hudson's Hope, 1,200 acres and a trailer
(01:27) BCIT, the 1999 diploma and the dot-com break
(03:05) Plenty of Fish, written in two weeks and priced at zero
(04:14) The $901,733.84 cheque from Google
(05:13) The midnight call, and the $575 million sale
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One mental model each day in a few minutes. Habits, business, building products and thinking clearly. From Dru Riley, founder of Trends.vc.
Nineteen seventy-eight. He is born.
He was born in Donauwörth, a walled market town in Bavaria where the Wörnitz river runs into the Danube. The family name is Frind. The family trade, by their telling, is farming. They trace it back roughly 500 years.
They count winemaking in that history alongside the fields.
Nineteen eighty-two. He is four.
He was four years old when the family left Bavaria for northeastern British Columbia. They landed at Hudson's Hope, a village on the Peace River with a few hundred residents, a dam and a long winter. The farm ran to 1,200 acres, roughly 485 hectares.
The house was a trailer. It stood on the land without electricity or running water.
A four-year-old does not weigh the decision that put him there. He notices the cold, the size of the field and the distance to the next house.
Nineteen eighty-six. He is eight.
They played chess at night, the father and the older of the two boys. This went on until Markus turned 10. He lost and lost and kept sitting down at the board.
He got better by studying patterns rather than by calculating further ahead.
Years later he described that as the skill he actually had. "I'm very good at looking at chaos and picking out exactly what matters."
Nineteen ninety-nine. He is twenty-one.
He finished the Computer Systems Technology diploma at BCIT in 1999. The timing looked excellent for about 18 months.
Then the dot-com market broke. He moved between internet marketing companies as each one cut staff, doing the same job at each stop: taking software that was full of errors and making it work. He used the word "optimizing" a lot.
He spent most of 2002 out of work.
Two thousand and one. He is twenty-three.
He was browsing dating sites with no particular plan. Each one of them wanted a subscription.
He registered plentyoffish.com and did nothing with it for two years.
Two thousand and two. He is twenty-four.
He met Annie in 2002. She was a graphic designer, blonde and by all accounts the more visible half of the pair.
He was the other kind of person in a room. Quiet, soft-featured, large-framed and somehow taking up less space than his frame suggested.
February two thousand and three. He is twenty-four.
Two months into the new job half his coworkers were gone, 30 people down to 15. He counted the empty desks and did the arithmetic on his odds.
He decided the fix was a skill no one could take off him. Microsoft had a newer framework called ASP.NET and job listings kept asking for it.
February two thousand and three. He is twenty-four.
He sat down at the computer in his apartment and wrote a dating site. It took him two weeks.
"I started Plenty of Fish in February 2003," he said later and described what he did in one line: "in the span of two weeks, I wrote a dating site on my home PC."
The site was plain. There was no design budget because there was no budget. What it had that the others lacked was a price of zero.
June two thousand and three. He is twenty-five.
Google launched AdSense that year, a few lines of code that put ads on any page and paid the owner a share. He pasted the code into the site over the summer.
The competitors charged members a monthly fee and spent the money on marketing. He charged members nothing and let advertisers pay for the traffic.
October two thousand and three. He is twenty-five.
By October the ads were paying real money. "By October, I was generating 4,000 or 5,000 bucks a month," he said.
That was roughly what the job paid, arriving from a site he built in two weeks as a tutorial exercise.
December two thousand and three. He is twenty-five.
The site crossed 10,000 users by the end of the year and the ads kept clearing several thousand dollars a month. He handed in his notice at the virtual-tours company.
He was the only employee of the new thing and he stayed the only employee for the next four years.
March two thousand and six. He is twenty-seven.
He photographed a Google check and put it on his blog. The amount was $901,733.84.
The check covered two months rather than one, because the first check Google sent was large enough that his bank refused it.
The internet did not believe him. The check worked out to about $15,000 a day from banner ads on a site widely called ugly and the reasonable response in 2006 was to laugh.
Two thousand and eight. He is thirty.
They took most of that summer on the French Riviera, he and Annie, while the site kept selling ads to strangers in Vancouver. An earlier trip to Mexico came with a yacht, a captain and four of her friends.
The business paying for all of it had three employees and margins above 50 percent. He was 30 and the money arriving each month was larger than what the work cost him.
At night he still logged on from wherever he was, spent a minute or two confirming the error messages were routine, then went back to the wine.
January two thousand and nine. He is thirty.
Inc. put him in the January 2009 issue under the headline "And the Money Comes Rolling In." The reporter, Max Chafkin, wrote that the site was on track for $10 million in revenue with margins above 50 percent.
The figure that traveled was one hour a day and on some days he put it at 10 minutes.
"Most of the time, I just sit on my ass and watch it," he told the magazine.
January twenty eleven. He is thirty-two.
On 21 January 2011 an Argentinian named Chris Russo found a SQL injection hole in Plenty of Fish. The exposed data covered close to 30 million accounts and the passwords were stored as plain text.
The call came at midnight and Annie picked up. The voice on the line said Russians seized his computer, that they were downloading the Plenty of Fish database and that his life was in extreme danger.
His account of the next few minutes: "I closed the breach if indeed there was one while my wife was on the phone and then I immediately ordered an investigation."
July twenty fifteen. He is thirty-seven.
On 14 July 2015 Match Group announced it was buying Plenty of Fish for US$575 million in cash. Frind was the sole owner.
The price worked out to about $5.75 for each of the 100 million accounts registered on the site.
He stayed on running the site for Match until 2019.
Two years after the deal he put his figure on it in an interview: "I walked away with $800 million from Match.com." The announced purchase price was US$575 million and no source reconciles the two numbers.
Twenty seventeen. He is thirty-nine.
In the fall of 2017 he paid $7.2 million for a 13.5-acre lakeside property in West Kelowna. The Bennett family held it for more than 50 years.
Part of the mansion became a tasting room. Six acres went under Maréchal Foch vines.
He had money, a family history in farming that the family puts at 500 years and no experience growing grapes.
November twenty seventeen. He is thirty-nine.
He sat for a ROB Magazine interview in a condo overlooking Coal Harbour. There was a one-year-old in the house and a three-year-old.
He listed what he was doing with the money: real estate, a winery, startups and a steel mill. "The steel industry hasn't changed technology in, what, 50, 100 years?" His approach was $10 million to $20 million checks into large asymmetric bets and buying old businesses to run internet technology through them.
Asked about relationships, the man who ran a dating site for 12 years gave a flat answer: one person has to be malleable and income level is a big predictor of love.
He also gave advice he was in a position to give. "Spend time with your spouse. If you're working 80 hours a week, the world outside the business doesn't exist."
January twenty twenty-four. He is forty-five.
On 13 January 2024 the temperature in much of the Okanagan dropped below minus 25 Celsius and it stayed close to that for several days on either side. The vines were dormant and the cold went past what dormancy protects.
The province's wine industry lost up to 99 percent of the 2024 grape crop. British Columbia had to let wineries import grapes from Washington State to have anything to crush in the fall.
September twenty twenty-four. He is forty-six.
Annie Frind died at her home in West Vancouver on 9 September 2024. She was 44. The obituary in the North Shore News names Markus as her ex-husband.
She left two children, Ava and Lucas. She left a sister, Sue, a brother, Paul and her parents, Karin and Eugene. The family asked in a Facebook notice that people respect their privacy.
He met her in 2002, when he was between jobs and the dating site was still an unused domain. She took the midnight call from the hacker in 2011. They married in Mexico in 2010 and at some point the marriage ended and no public record says when.
Twenty twenty-five. He is forty-seven.
The Vernon vineyard brought in Syrah at about 27 brix, a measure of the sugar in the grape and a number that means fully ripe. Merlot came in at 25 to 26.
Five years earlier the local view was that nothing would ripen up there. He claims these are the northernmost vineyards in the world that can ripen Bordeaux varieties.