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NOVEMBER 2025 VOLUME 9, ISSUE 11
TOPH’S TAX RESOLUTION TIMES
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Triple Adventure MY ONCE-IN-A-LIFETIME YEAR OF GOLF
Many of you know from this newsletter about my repeated efforts, almost every year for the last 20 years, to reach my lifelong goal of qualifying for the U.S. Open. I haven’t made it. Yet. But I am happy to report that this year, in another aspect of the sport, my luck turned for the better. By sheer good fortune, I had the opportunity to play several of the world’s best- known golf courses. From great Scottish courses on the North Sea to championship venues on the Atlantic and Pacific oceans, these are courses I will probably never get a chance to play again.
The worst part of the trip came when my golf clubs didn’t arrive with our flight. I spent hours on the phone with the airlines, trying to get a human on the phone to find out where my clubs were. I had to play with rental clubs, and it was extremely frustrating. As it turned out, my clubs had never left Cincinnati, and they finally arrived in Scotland on the third day of the trip. Nevertheless, the trip was a great experience. We played 10 rounds over seven days on nine unique courses, including several that have hosted the British Open, the oldest golf tournament in the world. I played decently; my lowest round on the trip was a 76 and my highest was 83. The high point for me was the last round at Carnoustie, reputed to be the world’s hardest course. I played the farthest tee back allowed in non-tournament play. The wind was benign, the weather was mild, and my takeaway was pure enjoyment: “Wow. I didn’t feel as if the course I had just played was one of the hardest in the world! (I still shot 82 however …)” TROUBLE AT KIAWAH ISLAND On an extended family vacation this past summer on Kiawah Island, S.C., I squeezed in four rounds of golf, including two on the famed Ocean Course, the scene of the Ryder Cup and several PGA championships. Many people may think Carnoustie is the most challenging course in the world, but I found the Ocean Course more difficult. Not only does it extend nearly three miles along the Atlantic shoreline, but it also presents countless difficulties. Every hole is edged by sawgrass and every bunker merges into sand dunes. I
played the Ocean Course once in calm weather (I shot 81), and once when a tropical storm was approaching, bringing gale-force winds of 30–40 mph (I shot a generous 89 …). It was extremely difficult! PEBBLE BEACH I flew to the opposite coast for my third golfing adventure, thanks to a gracious invitation from our business partner, iHeartMedia, to join their company-hosted trip to Pebble Beach. In addition to playing Pebble Beach, widely seen as the top public course in the country, we played Spyglass Hill and Spanish Bay. From the ocean views to the multimillion-dollar houses surrounding the course, Pebble Beach Resort is a first-class operation. And by the way, I shot 80-79-80-82 — so consistently mediocre! After Pebble Beach, I went straight back to running our business and helping raise our six kids. Most days, the closest I’ll get to playing golf is hitting a few putts on my green at home (which doubles as a playing field for our kids). Ironically, I’ve only played golf once all year in the state of Ohio! For now, the clubs are back in my office and unlikely to be used again until I clean off the dust in the spring to prepare for the 2026 U.S. Open qualifier!
Here is the story of my once-in-a-lifetime year of golf.
THE SCOTTISH EXPERIENCE The highlight was my annual golfing trip with 11 buddies. We’ve taken trips of 3–4 days together every year for 17 years, but this year, we traveled outside the U.S. for the first time to Scotland, home of the oldest courses in the world. This was a major commitment. Getting our wives’ approval to spend nine days away was no small thing.
–Toph Sheldon
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Toph’s Tax Triumphs
The holidays are a magical time that brings together loved ones and a little chaos. Between the pie-making and travel plans, it can be easy to forget what we’re gathering to celebrate. This Thanksgiving, let’s not just carve the turkey, but also carve out some time for mindful traditions the whole family can enjoy. From sharing what you’re thankful for to hosting a family Thanksgiving talent show, this year is the perfect chance to create new traditions that deepen connections and spark laughter. Get ready to gobble up the fun together. FILL YOUR HOLIDAY WITH GRATITUDE AND GAMES Whisking Up New Traditions This Thanksgiving
While resolving tax problems for our clients can be complicated, our successes sometimes spring from the most basic principles. We won one recent case largely because we wouldn’t give up. Sheer persistence won our client a 90% break on his tax bill. This client was a self-employed real estate agent who owed the IRS about $75,000–$80,000 for the 2016–2023 tax years. He had actually contacted us years earlier, but decided at that time to hire a different company. He later admitted he had gone with Brand X because they were the cheaper option. In hindsight, he said he wished he hadn’t. The other company made an offer in compromise on his behalf to the IRS, but the agency rejected it, and nothing was accomplished. That’s when the client returned to us for help. Like many self-employed people, this client had failed to have taxes deducted from his income. When he couldn’t pay what he owed at tax time, his debt snowballed. Winning the IRS’s acceptance of offers in compromise can be very difficult, but we believed we could make a good case on his behalf. We made an initial lowball offer of $162, which the IRS rejected. The agency argued that many of our client’s business expenses were actually personal expenses. We appealed the decision and made a strong case that the deductions were legitimate. Our client had to drive to and from showings, manage signage for properties, and pay other miscellaneous expenses just to do business. Fortunately, the IRS agreed, recalculated his income, and came to their compromise offer of $8,358. We won this case because we refused to give up. Also, we do our homework. Some other practitioners simply fill out forms and send them to the IRS, but winning these claims takes more than that. We drill into the details of every client’s case and prepare offers that paint an accurate picture of their situation, taking into account the human factors. We know our client’s strengths and weaknesses and negotiate in a way that emphasizes the former. While this client’s situation was typical in many ways, the unique aspect of his case is that he had reached out earlier, made the mistake of going with the cheaper option … and lived to regret it. Persistence Pays: Winning a Big Break for a Client
GATHER FOR GRATITUDE Thanksgiving is all about honoring what we are grateful for in life,
and it can be a fun activity for you and your children to share. You can gamify gratitude in several ways, like creating a thankfulness jar where everybody adds slips of paper describing
what they most appreciate. You can take turns reading them after dinner and even make a guessing game out of who wrote what. It could be as simple as gathering around the table for breakfast and everyone saying one thing they’re grateful for.
TURKEY DAY TRIVIA There’s no better way to digest after the big Thanksgiving feast than having fun. Pick out some of your favorite board games or a deck of cards for a post-meal game night. You could test everyone’s knowledge with a holiday-themed trivia competition or create a scavenger hunt around the house. No matter the game, ensure everyone from grandparents to kids can join in. Keep it focused on connection, not just winning. If you want to go all out, challenge all your guests to be ready with their best skills for a family talent show. A SOUNDTRACK TO THE STUFFING Create a perfect soundtrack you can play while everyone helps with the cooking or winds down after dessert. Before the big day, ask everyone in the family to add one or two songs to a Thanksgiving playlist. Prompt them to pick tunes that remind them of the season, happy memories, the joys of being together, or even their favorite dishes. You can keep adding to this list in subsequent years, turning the songs into a playable family history.
–Toph Sheldon
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ASHLEY’S CORNER A SURPRISING WIN: OUR KIDS ACTUALLY LIKE OUR FAMILY CHORE CALENDAR
We have reached a new family milestone. Five of the six kids are going to school or preschool this fall. I am packing all these backpacks every day. Everybody is getting on the bus together. Each of the kids has different homework assignments. They are all involved in different activities and sports, and each one has assigned chores at home. How can a parent keep five kids and a toddler on the same page?
When they have checked off all their chores for the day, a shower of animated confetti or emojis explodes on the screen with the message, “You have completed all your tasks!” They get so excited. They can turn their stars in for rewards.
We’ve gone digital.
Toph and I are figuring out the rewards part. We are definitely not paying the kids for doing chores; that is their responsibility, as members of the household. But we do want them to have some reward for their stars. It might be an activity or an experience, like using 200 stars to go out for ice cream on a Wednesday night. There’s a payoff for me, too: I have to do fewer chores because the kids are emptying the dishwasher and wiping the counters and feeding the dog! It is fun for me, and it’s teaching them a little responsibility.
Our latest innovation is a framed, color-coded Skylight calendar on a stand on the kitchen counter, with all the kids’ chores and homework on it. When the calendar isn’t active, it doubles as a picture frame for our family photos. I can add items to the calendar anytime, using an app on my phone. I might assign one child to take out the trash on Mondays, Wednesdays, and Fridays, and others to empty the dishwasher, feed the dog, or wipe the counter. I also enter each child’s homework. Mac might be assigned to read for 30 minutes, or Roz might need to practice piano. Each of the kids has their own color-coded checklist of tasks, and each time they complete a task, they click on their name and check it off. They can accumulate stars as rewards, based on a point value I assign for each task.
Next up: I am getting back to my own task list of organizing the house. That is a job that is never done!
The biggest surprise is how much the kids love it. They are super into the checklist, looking at the calendar to see, “What do I have to check off?”
Take a Break
APPLE-CRANBERRY SALAD
Ingredients
Inspired by WanderlustAndWellness.org
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6 slices of bacon
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3/4 cup dried cranberries
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1/3 cup balsamic vinaigrette
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1 Honeycrisp apple, peeled and thinly sliced
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1/3 cup olive oil
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1/4 red onion, thinly sliced
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2 tbsp raw honey
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1/2 cup feta cheese
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8 oz fresh baby spinach, rinsed and dried
Directions
1. In a large skillet, cook bacon until crispy. Remove it from the pan and set on a paper towel-lined plate to cool. 2. In a small bowl, whisk together balsamic vinaigrette, olive oil, and honey. Set aside. 3. In a large bowl, add spinach, cranberries, apple slices, red onion, and feta. Crumble bacon pieces over the top. Use salad forks to toss ingredients thoroughly. 4. Add dressing to the salad and toss again until well-coated.
Solution on Page 4
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Cincinnati Tax Resolution Powered by Toph Sheldon 9200 Montgomery Rd., Ste. 7B Cincinnati, OH 45242
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INSIDE
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Toph Scores: 3 Lucky Golf Outings in a Single Year
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From Thankful Jars to Turkey Trivia Toph Negotiates 90% Off a Client’s Tax Bill Ashley’s Corner: A Digital Family Calendar Makes Doing Chores Cool Apple-Cranberry Salad
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Early Release of a Record-Breaking Tax Fraud Perpetrator
A Tax Fraud Mastermind Gets Early Release TOPH’S TAX NIGHTMARES
The IRS’s enforcement weapons are powerful enough to give delinquent taxpayers nightmares, from seizing bank accounts and assets to garnishing wages. But it takes a special kind of crime to send a tax scammer to jail. A defendant’s intentions are critical in setting the severity of the punishment sought by the IRS and the U.S. Justice Department. When prosecuting a case a decade ago against former Chicago attorney Paul M. Daugerdas, the perpetrator of the largest tax shelter fraud in history, government lawyers deemed Daugerdas’ motives plenty sinister enough for a federal judge to send him away. U.S. District Judge William H. Pauley III did exactly that. In 2014, he sentenced Daugerdas, who was 63 years old at the time, to 15 years in federal prison. Daugerdas denied any wrongdoing. His case made the news again last year, when he was among 1,500 prisoners whose sentences were commuted by former President Joe Biden. Daugerdas wasn’t pardoned for the crime; the commutation merely shortened his sentence. He had been serving his time in home confinement since the pandemic.
deliberately sought to weave “an intricate web of deceit” that enabled clients to evade $1.6 billion in taxes by using a cookie-cutter
product designed to create fictitious investment losses. His massive fraud also brought down his once-prominent law firm, Jenkins & Gilchrist. The Texas- based firm was toppled by civil suits filed by clients. The firm entered a no-prosecution agreement with the government, closed its doors, and paid a $76 million fine.
Daugerdas may have shed his electronic ankle bracelet, but the commutation didn’t free him from his legal obligation to pay restitution to victims of the financial chaos he left in his wake. He was ordered to forfeit $164 million in proceeds from client transactions, including a vacation home on Lake Geneva, Wisconsin, and pay an additional $371 million in restitution, with payments to begin after his release from jail.
Now nearing his mid-70s, Daugerdas is still fighting the IRS’s effort to collect restitution in court.
Daugerdas made more than $95 million in personal profit by selling phony tax-shelter schemes to clients. The Justice Department said Daugerdas
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