Billy
The skycap who paid coworkers to take his shifts—then took the whole company
As a teenage skycap at Winnipeg airport, Voulgaris spotted that fishing-charter weekend shifts paid $400-500 vs $80. When the boss refused to give him those shifts, he paid other workers $80 to hand theirs over, then eventually undercut the owner's contracts and took over the company.
“I realized that the Saturday, Sunday shifts were very profitable because we had American fishing travel that were people would come in on these boats and they'd have to take a charter plane to go fishing somewhere in Northern Canada. And those days you're making $400 or $500 in an 8-hour shift, easy. Wow. And so I basically went to the boss of the company, I was like, hey, I really want to work the Saturday and Sunday shifts.”
Tactic
Upsell the captive customer: limos, strip clubs, and 3x-markup Cuban cigars
To out-earn other skycaps, Voulgaris turned himself into a concierge for traveling fishermen—arranging limos and strip-club trips and sourcing Cuban cigars (illegal in the US) that he sold at three times their value.
“I was doing things like getting them limos to go to the strip clubs when the 4 hours that they're getting them Cuban cigars, because Cuban cigars are illegal in the United States, and when they land and like making sure they had like Cuban cigars and charging them like 3 times the value for that.”
Steal thisWhen you have a captive, high-spend audience, sell them the hard-to-get extras at a fat markup.
Tactic
Bet the half, not the full game, when books just divide by two
Sportsbooks priced halftime/second-half totals by mechanically halving the full-game total they were good at predicting. Voulgaris exploited the books' laziness by finding situations where the real half-by-half split was wildly skewed.
“So the second half over was like, you'd have teams playing, doing this 41 times a year. And they would go 9 overs in the first half, 30-whatever, 32, 33 with some pushes in the second half. And you could just print money making this bet. And that's what I did.”
Steal thisWhen a market prices a sub-bet by mechanically splitting a parent number, hunt for cases where the real split is lopsided.
Tactic
Bet the half, not the full game, when books just divide by two
Sportsbooks priced halftime/second-half totals by mechanically halving the full-game total they were good at predicting. Voulgaris exploited the books' laziness by finding situations where the real half-by-half split was wildly skewed.
“So the second half over was like, you'd have teams playing, doing this 41 times a year. And they would go 9 overs in the first half, 30-whatever, 32, 33 with some pushes in the second half. And you could just print money making this bet. And that's what I did.”
Steal thisWhen a market prices a sub-bet by mechanically splitting a parent number, hunt for cases where the real split is lopsided.
Number
$10-12M a year gambling for 10-15 years straight
Voulgaris says his net winnings from sports betting ran $10-12 million per year for at least 10 to 15 years, putting his lifetime gambling profit into nine figures.
$11M
Annual net gambling winnings · USD/year
“I made between $10 to $12 million a year gambling for 10 to 15 years minimum.”
Take
Being underestimated is a gambler's greatest edge
Voulgaris says Billy Walters' biggest asset wasn't fast talk—it was his Southern accent making people think he was less intelligent than he was. Letting opponents underestimate you is a core advantage.
“if you're a gambler, one of the greatest things you can have going for you is people thinking you're not as intelligent as you actually are.”
Framework
Use a 'beard' so nobody knows you're the sharp
Because winning bettors get cut off, Voulgaris never placed his own bets. He recruited 'beards'—successful businessmen, degenerate gamblers, or celebrities like Floyd Mayweather—to make bets for him so bookmakers thought they were dealing with a sucker, not a shark.
“Nobody knew who I was. Nobody knew I was winning money betting because I was never the guy making the bets. I'd always find what's called a beard who would make my bets for me. And so I've had numbers of numerous beards throughout the years who were making my bets for me. And they were either they were really successful business people or degenerate gamblers or Hollywood people or Floyd Mayweather, who's a beard for half an afternoon for me.”
Steal thisIf winning gets you banned, route your action through a proxy the house believes is a loser.
Story
He found Bitcoin getting paid by Chinese betting clients in 2013
Voulgaris first acquired Bitcoin around 2013 at roughly $180 when a contact who ran his China betting accounts offered to pay him that way, saying everyone in China loved it. It quickly ran to $600 then $1,000 before crashing to ~$150 after the Bitfinex hack.
“And he's like, I can send you Bitcoin. And I was like, Bitcoin, really? You guys like Bitcoin? I think the price was around $180 at the time. He's like, yeah, everyone in China loves Bitcoin. And I was just like, well, if everyone in China loves Bitcoin, maybe I should love Bitcoin too.”
Framework
Get paid by being the most annoying person in the debtor's life
On collecting gambling debts without muscle, Voulgaris says the leverage is future access: a smart bookmaker pays you out of pocket because cutting off the guy who always wins costs them more long-term. The other tool is relentless, polite annoyance.
“if you knew that I was always going to win, and if you didn't pay me, you knew you were not going to get my bets anymore, you might go out of pocket to make sure your relationship with me was good, knowing that eventually you're going to make the money back if you're smart enough.”
Steal thisMake your continued business so valuable that the other side eats a short-term loss to keep you.
Story
He automated himself out of the betting because emotion broke the model
Voulgaris realized his edge only worked when his mindset was perfect, and life (relationships, bad moods) corrupted his judgment as the human input. So he hired a Harvard genius referred by Brandon Adams to build simulation models that made his full-game betting fully automated and emotion-free.
“when I decided that my method works but it only works if my mindset is good— if I want to have a life and have like emotional relationships with females and have a partnership, whatever, and I'm upset, I'm making bad decisions when I'm gambling— it's harder to be like a perfect arbiter of what's right and what's wrong and what's the right information when you're the input. So I wanted to automate me, basically.”
Steal thisIf you are the unreliable input in your own system, build a model that removes you from the decision.
Number
Sportsbook returns: 4-4.5% per bet a bad year, 8-9% a good one
Voulgaris measures his operation not by annual return but by ROI per bet. A bad year is 4 to 4.5% on every bet placed; a good year is in the 8s and 9s—and he deliberately accepts lower ROI to place more total volume.
$4.5
ROI per bet in a bad year · percent
“a bad year for us was 4.5 for 4 to 4.5% on every bet we're making. A good year is like in the 8s and 9s. And now of course you want to have as many bets as possible and the most profit as possible. So you're, you want your ROI to go down a little bit as your bets go up.”
Framework
Pick games where you're the better player
Voulgaris applies poker's core principle—play against people worse than you—to all his businesses. He deliberately avoids finance and other arenas crowded with smarter, better-resourced competitors.
“the number one edge in poker is playing with players who are worse than you. That's just it. And so I try to apply that also to my businesses. I try to stay away from people that are smarter than me, where there's plenty of them.”
Steal thisChoose your competitive arena by who's at the table, not by how big the prize is.
Take
Every dollar earned goes straight into Bitcoin
Voulgaris says his entire 'boring' money strategy is converting every dollar he earns directly into Bitcoin—and that he has made more from Bitcoin than from a career of sports betting.
“I do super boring stuff. Every dollar I earn goes directly into Bitcoin. That's my boring stuff.”
Story
He sold a plane, homes, and all his assets to buy the 2017 Bitcoin dip
During the 2017 crash Voulgaris liquidated property in Mexico and Europe, vacation homes, and a plane to buy more Bitcoin at $3,300. Friends were so alarmed they tried to schedule an intervention.
“I sold, I also sold all of my assets during the 2017 dump. I owned property, uh, outside of— I owned property in Mexico, I had some vacation property, I had some property in Europe, I had a plane. Sold it all. Uh, actually had some friends try to schedule an intervention for me because they thought I'd lost my mind when I sold everything to buy more Bitcoin at $3,300.”
Resource
Mesenchymal stem cells as the top biohacking investment
Voulgaris names umbilical-cord-derived mesenchymal stem cells (he went to the Stem Cell Institute in Panama) as the single best health thing he's ever done—permanent injury repair plus a months-long 'Superman' feeling. He pairs it with sauna, peptides, and red-light therapy.
“the best thing I've ever done and the thing I could recommend to anyone who can afford it is, aside from sauna 5 times a day, or 5 times a week, excuse me, is, is stem cells, getting actual stem cells that are mesenchymal, which is through the umbilical cord.”
Fact
Muscle-injury risk jumps 25% when athletes play more than one game per 6 days
Voulgaris cites research that a footballer's risk of muscle injury rises 25% if they play more than one game every six days—a lesson he learned the hard way after running his soccer club's players into a 6-game losing streak.
“your risk of muscle injury goes up 25% if he, if a football player plays more than one game every 6 days. There's plenty of research that can make you come to good decisions.”
Take
Delusional self-belief as a strategy: just keep trying until you get there
Asked whether he foresaw going from Vegas bets with his dad to owning a soccer club, Voulgaris credits 'delusional' confidence and belief—the conviction that you can craft your own path if you simply keep trying.
“I was very delusional when I was younger. I was very like, I'm a very, I'm really a big fan of that sort of stuff. Like speaking things, not speaking into it, but just like having the belief and why not? Why not? I mean, I don't know. The universe is kind of there for you to do it. Like you can craft your own path. Just keep trying until you get there.”
Billy
Harala Bob: the bettor who found the mispriced first-half over-under
Pro sports bettor Haralabob noticed bookies set first-half over-under lines by simply halving the full-game line, ignoring that scoring spikes late as losing teams foul. He quietly exploited this mispricing, especially against specific coaches, and now works for Mark Cuban's Mavericks.
“So he realized it was this small edge where they thought they were taking the full score and dividing by half and making that the line. He's like, oh my God, this is almost always going to be under. And he specifically noticed that these 3 teams, their coaches would do that foul strategy way more in the second half.”