Two Off The Tee

Jeff Shin
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Brothers Jeff and James Shin — proudly high-handicap Chicago golfers with long-time careers in real estate and lending — break down their world of golf: gear, matches, league drama, course stories, and the grind of getting better. It’s rivalry, personality, and unfiltered golf talk from two guys who compete on and off the course. If you’re into golf, banter, and the real amateur grind, this is your show.

  1. 1d ago

    Would you give up outdoor golf? Jeff Shin vs James Shin | Golf simulators

    I might rather play golf indoors. James still wants to play outside. We both own an indoor golf business, but we want different things from a round. I like getting shot data straight away and having more time left in the day. He likes the simulator without wanting to give up a real fairway. We're both behind on the Internet Invitational. James calls it the Masters of YouTube golf, while I wonder how many competing events a viewer can follow. We also disagree about the line on a golf ball. James stopped using it after he felt he missed more putts. I keep it as part of my routine. We look back at the one-putts that kept us in a past match and talk about what a putter switch showed me about my misses. Would you choose an hour on a simulator or a round outside? Do you line up your ball? Follow Two Off The Tee on Spotify or Apple Podcasts for the next episode, and leave a review with your take.

  2. Nov 3

    My Brother Can't Plug In a Cable, but He Built Our App

    Sergio Garcia is out at LIV and going to the DP World Tour. Jeff and James argue about whether LIV players should have to earn their way back through Q School or the Korn Ferry Tour. Jeff says the grind isn't worth it late in a career. James says they still have to pay for the houses, and he would do it. We also get into the 850 website names LIV owned, what LIV got right at its events, and why James thinks the whole thing paid players too much. Internet Invitational season 2 is out. Jeff watched episode one while he worked. James stopped at the Beef tribute, and Jeff thinks he met Beef's brother years ago at Deerpath. Plus gimme fights, F-bombs, and whether you'd want Duke as your partner with $4 million on the line. Simmies update: turf is next, Jeff got the app and the door working, and we explain the gray screens and the $30 an hour price. Free Relief: course manners. James tells the story of breaking his toe on a tree branch after losing a hole. We also cover gimmes, penalties for bad manners, and music on the course. WHAT'S IN THIS EPISODE - Sergio Garcia leaves LIV - Should LIV players go back to Q School? - LIV's 850 website names - Internet Invitational season 2 - Simmies build update - James breaks his toe - Gimmes and music on the course Do you give a gimme when someone asks? Follow the show and tell us. Two Off the Tee. Jeff Shin and James Shin

  3. Oct 26

    My Brother Won the Cup. I Say He Rigged It.

    James's team won the Simmies Cup, and the signed flag made it onto the show. Jeff says the Chief Competition Officer turned into the Chief Corrupt Officer: three of the five best players on one team, then no handicaps. James says those are excuses, and points out Jeff once said he was the better golfer of the two brothers. Jeff owes him Johnny's Beef. Kevin Kisner says Rory McIlroy went to India for $10 million. James thinks Rory is a hypocrite after years of bashing LIV players for chasing money. Jeff says it was a PGA event and nobody plays for free. Then LIV is restructuring after bankruptcy, offering equity in place of big checks, and Louis Oosthuizen called leaving the hardest decision of his career. If your company was going broke and offered you half the place for a smaller check, would you stay? On Simmies: the bays are painted, screens and projectors are next, and the app for booking, paying, and unlocking the door is almost ready. Plus our new mascot, Gimmies the Golfer. The Cup recap: alternate shot was the most fun format, a nine-hole best ball swung on a three-putt, and James got a wake-up call playing Sun. Free Relief: Michael Kim is 912 for 912 inside 3 feet. Should anything inside the shaft length be a gimme? And Ross Steelman used ChatGPT to help build his clubs. Would you? WHAT'S IN THIS EPISODE - Kisner vs Rory and the $10 million - LIV 2.0 and Oosthuizen's exit - Smaller check, half the company - Simmies build-out and the app - Simmies Cup recap - Should a two-footer be a gimme? - ChatGPT picks a tour pro's clubs Is a two-footer a gimme? Follow the show and tell us. Two Off the Tee. Jeff Shin and James Shin.

  4. Oct 19

    Jon Rahm Is Out at LIV. Would You Have Stayed and Bet on Yourself?

    James Shin looked at Jeff Shin's Simmies Cup lineup and called one pairing a throwaway. He says they won't win a single hole, even from the 100-yard marker. Jeff's answer: a software engineer on his team ran every possible pairing through a Monte Carlo simulation, and they like their odds better than 60% to sweep the first match. We recorded this two days before the event, and it gets heated. It starts with Jon Rahm leaving LIV. Jeff heard he's walking away from about $100 million and wants to know why he wouldn't stay and take equity in LIV 2.0. James says no one knows what LIV is doing and no one cares. Jeff calls it W-2 versus 1099: the steady paycheck or the gamble. Blades Brown, 19, also has his PGA Tour card. We give an update on the Simmies build-out, and Jeff explains why we're writing our own software with AI instead of paying for it. Then the Cup. James wants three rivalry matches set up on purpose, and Jeff won't do it. The losing captain buys a flag for the winner's wall. If Jeff's weakest pair wins a match, James has to admit Jeff should be CEO. Free Relief: fall golf. Your ball lands in the rough and disappears under the leaves. James would give a free drop if everyone saw where it went. Jeff says no leaf rule unless you call it before you tee off. WHAT'S IN THIS EPISODE - Jon Rahm leaves LIV - W-2 or 1099? - Blades Brown gets his Tour card - Building Simmies with AI - The Monte Carlo draft - The flag bet and the CEO bet - Lost in the leaves: free drop or lost ball? Free drop or lost ball? Follow the show and tell us. The Simmies Cup result is next episode. Two Off the Tee. Jeff Shin and James Shin.

  5. Oct 13

    Would You Play One Round of Golf With Two Years of Your Life on It?

    Tom Kim shot 64, won gold, and got out of Korea's military service, which runs 18 to 21 months. His teammate S.H. Kim missed by two shots and still has to go. James Shin says he'd have left the Presidents Cup right away too, and he'd be happy for Tom even if he were S.H. Jeff Shin thinks that one round carried more pressure than a major. Would you want your service decided by one round? Then Jon Rahm. He passed on the PGA Tour's offer in February, LIV filed for bankruptcy, and now he's out. James says take him back because people want to watch him. Jeff puts it in work terms: a guy quits Simmies for a bigger paycheck, the new place falls apart, and he wants back in. James said no on the spot. The PGA Tour wants $30 million a year to sponsor each of its top events starting in 2028, and fourteen companies bid on the last four. James would rather buy every billboard on 294. Jeff thinks you'd need a CEO who's obsessed with golf. The Simmies Cup is next week. James argues for no handicaps, says match play was never meant to be fair, and Jeff has no comeback. It's straight up, gold tees, 8 a.m. at Bridges of Poplar Creek. Free Relief turned into James's story: second place by one stroke again, a 100-yard hole-out on 17 by the winner, and an egged car in Elmhurst. Plus, should our league give out a flag or a trophy? WHAT'S IN THIS EPISODE - Tom Kim's gold medal and the army - Is that round harder than a major? - Jon Rahm leaving LIV - Would you rehire him? - The PGA Tour's $30 million price tag - Simmies Cup: straight up, no handicaps - Robbed by one stroke again Would you rehire the guy who left? Follow the show and tell us. Two Off the Tee. Jeff Shin and James Shin.

  6. Oct 6

    Scottie Scheffler Conceded a 32-Footer After a Fan Yelled. Would You?

    Scottie Scheffler conceded a 32-foot putt at the Presidents Cup after a fan yelled in Nico Echavarria's swing. James Shin calls it the right move and says he'd do the same, because he wants to win fair and square. Jeff Shin isn't buying the halo. Scottie still had a tap-in for par, and Jeff says he doesn't give that putt if he's staring at bogey. Would you? Then the brothers fight about their own cup. James wants to play straight up with no handicaps, and he brings it up after the draft. Jeff calls it a hustle, says you just average the two handicaps in alternate shot, and then falls for the bait anyway. First nine best ball, second nine alternate shot, then singles, with dinner riding on which captain wins. The Oklahoma 2v2 happened. Two guys came up from Oklahoma to play us, and they lost. Jeff came away impressed by how a low handicapper scrambles and chips. James saw mediocre golf and says a 40-foot putt is luck, not skill. They played the same round and still can't agree on it. Also in this one: Presidents Cup week at Medinah, Tom Kim and Korean golfers' military service, and Jackson Koivun's club twirl on 18. Free Relief: does playing for money make you a better golfer? Both hosts say yes. Jeff wants to go further and ban "that's good" whenever money's on the line. Putt everything out. WHAT'S IN THIS EPISODE - Scottie Scheffler's 32-foot gimme - Korean golfers and military service - Jackson Koivun's club twirl - Straight up or handicaps for our own cup - The Oklahoma 2v2 result - Real 2-handicap or home-course handicap? - Does gambling make you a better golfer? - No more gimmes Does playing for money make you better? Follow the show and tell us.

  7. Sep 29

    Caddie Quit on Hole 9 Over an Umbrella: Would You Walk?

    Bryson posted "I'm coming home." James Shin thought it meant a return to the PGA Tour. Jeff Shin says it was a backyard hole-in-one challenge over his house with a crew of YouTubers. James fell for it, and he admits it. Then the caddie who dropped the bag on hole nine. Jeff tells the whole story: a range argument about where the bag went, an umbrella in the bag on a sunny day, a few choice words the golfer wouldn't take back, and "Man, I'm out." Would you ever walk off a job mid-round? Presidents Cup week at Medinah, and whether J.J. Spaun got snubbed. Is a captain's pick about the best player, experience, or who your buddies are? Then the brothers make it official: Jeff vs James, Team Black vs Team Red, captains of our own house cup. Best ball, alternate shot, singles match play, and a real argument about how a snake draft works. Two claimed 3-handicaps are flying in from Oklahoma. And the rules fight: a ball rolls into someone else's pitch mark in the fairway, and the official says it's playable. The hosts rule on it. WHAT'S IN THIS EPISODE - Bryson's "I'm coming home" tease - The caddie who quit on nine - Was J.J. Spaun snubbed? - Presidents Cup picks: best player or buddy pick? - Team Black vs Team Red: the brother vs brother draft - Two claimed 3s from Oklahoma - Free relief from a fairway pitch mark? Free relief from someone else's pitch mark: yes or no? Tell us. Follow the show. Leave a rating if this one made you argue with your steering wheel. Two Off the Tee. Jeff Shin and James Shin.

  8. Sep 22

    Presidents Cup at *MEDINAH*: Jeff Shin vs James Shin

    Presidents Cup week is in Chicago. Jeff Shin wants Team USA at Medinah. James Shin takes the International side -- he just says Team Korea. The one clip they both actually know is Tom Kim putting his putter on the ground. Then two claimed 3-handicaps from Oklahoma booked flights after a challenge. The other group backed out. These two did not. Exhibition 2v2. James says give them strokes. Jeff says maybe it's a hustle. Also on this tape: our league's tenth season is in the books. James missed the last weekend by a stroke. They graded the year and argued whether 85% handicap was too much. Free Relief: Jeff's putt hammers the flagstick and ricochets. James says too fast, then gives him the par. Then Jeff hits the wrong ball and nobody cards the two-stroke. WHAT'S IN THIS EPISODE - Presidents Cup at Medinah - USA vs International / "Team Korea" - Tom Kim putter meme - Two claimed 3s booked flights - Season ten wrap + 85% handicap - Flagstick ricochet: does it count? - Wrong ball, asterisk win? Does a ricochet off the pin count if your brother gives it to you? Tell us. Follow the show. Leave a rating if this one made you argue with your steering wheel. It helps people find us. Two Off the Tee. Jeff Shin and James Shin.

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About

Brothers Jeff and James Shin — proudly high-handicap Chicago golfers with long-time careers in real estate and lending — break down their world of golf: gear, matches, league drama, course stories, and the grind of getting better. It’s rivalry, personality, and unfiltered golf talk from two guys who compete on and off the course. If you’re into golf, banter, and the real amateur grind, this is your show.

Information

  • Creator
    Jeff Shin
  • Years Active
    2025 - 2026
  • Episodes
    50
  • Rating
    Explicit
  • Copyright
    © Jeff Shin
  • Show Website
    Two Off The Tee

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