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From Bartending to Barstool Sports With Kelly In Vegas

Written by: Bill Krackomberger
Updated October 14, 2022
5 min read

It’s episode 109 of Wise Kracks and we’re bringing you a special guest-centric edition of the show!

Your hosts Bill Krackomberger and Jon Orlando are joined by the inimitable Kelly Stewart, aka Kelly In Vegas! A rockstar in the world of sports betting, Kelly can be found on the Barstool Sports show ‘Money Shots’ and is an owner of WagerTalk.

She chats with the guys about how she got into sports betting, dealing with trolls, working at Barstool Sports, and the story behind how she got fired from ESPN before she even started. Get ready to learn a whole lot more about one of sports betting’s biggest and most unapologetic personalities on this episode of Wise Kracks!

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Climbing the Ladder in the Sports Betting Industry & the Trolls Along the Way

Kelly In Vegas is no stranger; she and Bill have worked alongside each other multiple times in the past. What makes Bill appreciate her company is that she remembers where she comes from, and where she came from was humble beginnings.

When asked how she got her start in the sports betting industry, she talked about how it all started with one wager.

I had a buddy who ran a book from back home, stated Kelly, He handed me a ticket… I hit a three-team parlay, and all of the sudden my life just kind of exploded.

That is to say that her life exploded in a good way; Soon she would find herself sitting at Todd Fuhrman’s desk, a former oddsmaker and current analyst at CBS Sports, who would ask her, “What’s your best bet this week?” After relaying her picks to him, he responded with.

Kid, you’re not gonna get rich betting road chalk in the NFL.

As tough as this was for Kelly to hear, she admits that he was, “so right about everything I did wrong,” which ultimately molded her into the star she is today.

After talk of Fuhrman’s influence, Jon wanted to know, “ Who else did you sponge off of?” With too many people to count, Kelly simply states, “Anyone I could meet.” For Kelly, it was all about gaining as many perspectives about the industry as she could.

For most public figures, there’s no upward momentum without trolls trying to take you down, and Kelly is no exception. She knows that the right move is to take the high road, but sometimes she just wants to “hit the retweet button and shred them,” whenever someone comes for her online, which Bill has dubbed “Telephone Tough Guys”. We’ll get to work on trademarking that.

In the end, Kelly knows that she has gotten to where she has by just being herself, and knowing that people want to learn from her, “I think most people that follow me are not following to fade me, they’re following because they actually know they’re gonna get good information.”

The Freedom of Working for Barstool Sports

With Kelly’s star rising and the personality she was known for, her eventual move to Barstool Sports couldn’t have been more fitting. “This industry is about finding people that you can work together with.” For Kelly, she had found those people at Barstool Sports and Barstool Sportsbook, where she co-hosts the show “Money Shots” with Megan Makin’ Money.

Funnily enough, she had found her place at Barstool right after one of her biggest careers moves up to that point had been taken away from her. Slated to join ESPN, she had been fired before she even got a Day 1. However, when one door closes another opens, and Barstool Sports President Dave Portnoy reached out to her and eventually brought her onboard.

“With Barstool, I get to be myself now,” Kelly says with a smile, “I get to create something I enjoy with them.” The freedom Barstool grants her as a personality and content creator has made Kelly much more passionate about her craft,

They say ‘go do whatever you want Kelly’… I get to post my parlays on Instagram, go to football games, and make fun of Tom Brady; you can’t do that at ESPN.

For Kelly, being herself also proves that she easily fits into a typically male-dominated role,” Krack, I’m annoyed I had to do my hair and make-up today, I’m one of the guys!”

Kelly had found her home at Barstool, and acknowledges that the rollercoaster that is her career has only led to something wholly fulfilling,

The ESPN firing was the best thing that ever happened to me… I’m happy with where I’m at now, and I wouldn’t change a thing.

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Catch Wise Kracks Thursday on YouTube

Welcome to Wise Kracks, the place to be for all things betting, pop culture, tips & more. Your hosts Jon Orlando and Bill Krackomberger provide insight on the NHL, NBA, MLB, & the NFL, without forgetting to have a little fun.

Every week brings a new guest to regale the guys with stories from the world of sports and entertainment. Wise Kracks is the perfect betting companion, with Bill sharing years and years of knowledge and expertise.

Tune into the WSN YouTube channel every Thursday for a new episode of Wise Kracks!

Image for Bill Krackomberger

Bill Krackomberger

Sports Betting Analyst, Content Specialist & On-Air Host

Online Sports Betting
Online Casino
Billy “Krackman” Krackomberger has made his living as a professional sports gambler for nearly three decades. You have seen him on ESPN, Gaming Today, and SiriusXM. His connections in the sports gambling industry run all the way to the top. His bets move the lines and regularly have him banned from books for being too sharp.
Nationality: American
Education: N/A
Favourite Sportsbook: FanDuel Sportsbook
Favourite Casino: Caesars Palace Casino
30 years
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