Victory Lap

Once you achieve Financial Independence, you may choose to leave salaried employment but with decades of vibrant life ahead, it’s too soon to do nothing. The new stage of life between traditional employment and Full Retirement we call Victory Lap, or Victory Lap Retirement (also the title of a new book to be published in August 2016. You can pre-order now at VictoryLapRetirement.com). You may choose to start a business, go back to school or launch an Encore Act or Legacy Career. Perhaps you become a free agent, consultant, freelance writer or to change careers and re-enter the corporate world or government.

Two-way Traffic podcast & transcript: The tax case of NHL hockey player John Tavares

John Tavares of the Toronto Maple Leafs is in a dispute with the Canada Revenue Agency that could impact pro athletes and high-income earners in general.

Financial advisor Darren Coleman, a cross-border expert, discussed the Tavares case in a recent episode of the podcast: Two Way Traffic. His guests were tax lawyer Shlomi Levy and tax accountant Kevyn Nightingale of Levy Salis LLP. The firm, which has NHL players as clients, is dedicated to U.S. and Canadian tax and estate planning for individuals, corporations, and those with cross-border interests.

In 2018 Tavares, then a US resident, left the New York Islanders to sign a seven-year, $77-million (US) contract with the Maple Leafs. For the first year of that contract his base salary was $650,000 (taxed in Canada at 53%) with $15.3 million a signing bonus (taxed in Canada at 15%). But now the CRA says that was all salary and wants back taxes. With penalties that comes to about $8 million US.

“The CRA says it was all employment income,” said Nightingale and his colleague Levy explained what a CRA win might mean. “It would make it harder for Canadian NHL teams to compete with American teams in lower-tax jurisdictions. But it goes beyond that.”

Link to podcast …

https://twowaytraffic.transistor.fm/episodes/game-night-john-tavares-vs-cra

Darren Coleman

Tax accountant Kevin Nightingale

Today I’m joined by my good friends, Kevin Nightingale and Shlomi Levy of Levy Salis LLP. Kevin is one of the top cross-border tax accountants and Shlomi one of the top cross-border tax attorneys in North America.

We’re going to talk about the John Tavares case and his tax issues with CRA. It’s getting a lot of press and attention. Tavares of the Toronto Maple Leafs is a hometown boy and it was a big deal in July 2018 when he went into free agency and signed with the Maple Leafs a seven-year contract that would have paid him $77 million [US] and $15 million of that was an upfront signing bonus.

Six years later, CRA wants millions of dollars of unpaid taxes because of the way the deal was structured. This can have an impact on how NHL teams recruit and could apply to every sports team, but also in the corporate world when trying to bring talent to Canada.  I know you guys have players as clients but do not represent Mr. Tavares.

Kevyn Nightingale

The main issue is it’s expensive to get athletes to come to Canada. The tax difference between Canada and the U.S. is wide and has been widening over years, especially since 2015 when the then new Liberal government decided to raise tax rates, particularly on high earners, and they were thinking of your home-grown high earners. But in a world where talent is mobile, particularly in things like sport, if you raise tax rates you lower their effective income and what they care about is the after-tax income.

Compare coming to play for the Toronto Maple Leafs, where tax rates are 53.5% on the vast majority of their income, and going to Florida where the tax rate is 37%. That makes a big difference. Now there are other states where there are significant taxes. California is getting close and New York City is getting close, but there are ways of dealing with that in the US that still make the tax rate effectively lower for many players.

Darren Coleman

So the structuring of the Tavares contract was trying to give him some tax benefit by structuring a signing bonus vs. a salary. Shlomi, can you dig into why that mattered?

Shlomi Levy

Shlomi Levy

Tax paid in the state of New York isn’t credited against the Canadian side, but is based on the Canada-US tax treaty and the potential tax savings were probably $1.3 million. But now, if CRA gets its way between penalties and interest six years down the road, it would be probably three or four times that amount in payment.

So you have to question the strategy. One of the things I like to discuss with clients and athletes is what’s the risk and what is the reward vs. the risk? You want to make sure people take those calculated risks. God knows how long this may take to settle and it might just not be worth it. I represent north of 50 NHL players come training camp and these guys can’t be bothered with legal discussions or tax discussions. They’re focused on playing hockey. This is going to be a huge distraction for John and his family if it doesn’t get settled quickly.

Kevyn Nightingale

He only had to pay Canadian tax of 15% on the signing bonus portion that he received prior to coming to Canada.

Darren Coleman

So I think his assumption was he was not a resident of Canada. I think that’s what CRA is challenging.

Kevyn Nightingale

He was by all accounts a non-resident of Canada because he was living in New York and playing for the Islanders, and had not yet come to Canada when he got this portion of the signing bonus. Now he ultimately did move to Canada, but that was after the fact. So we’re only talking about the part that he received prior to coming to Canada. The deal is if you have a signing bonus and it’s properly authorized as a signing bonus, and you’re a non-resident of Canada and it’s paid by a Canadian team, your Canadian tax goes down from 53.5% to 15% so that is a sizeable savings.  As a resident of the US he has to pay US tax on his worldwide income. And he’s paying US tax, and he’s paying New York state tax because he lives in New York state. Now he will get a credit for the Canadian 15% but he’s still paying effectively US and New York rates that may go as high as 45% or even more. So Shlomi is right. The savings are about a million dollars.

Darren Coleman

The difference between the tax rate and what the Canadian tax rate would have been?

Kevyn Nightingale

Yes, he would have been ahead of the game, but not by a huge amount. It’s not like someone who’s living in Texas or Florida, which many athletes do. But CRA says we don’t care what the US aspect is. We lost the difference between 53.5 and 15. That’s what we care about.

Darren Coleman

You mentioned earlier it’s the characterization of a signing bonus. Is that also part of what CRA is saying? That it wasn’t a signing bonus? You received it as income?

Kevyn Nightingale

CRA is arguing that it’s really employment income but you call it a signing bonus. We’re still going to call it employment income. One of the factors that goes into it is whether the employee, in this case, the athlete, has to repay any of it if he doesn’t actually show up to work. So, injured, retired, not feeling like working that kind of stuff. Well, apparently that is not at issue here because if Tavares did not show, he would not get the signing bonus. So that argument is a loser for CRA because they just don’t have the facts on their side.

Shlomi Levy

The nature of the NHL contract is you signed a contract that’s guaranteed and you’re owed the money.

Darren Coleman

Where do you think CRA has  ground to stand on this one?

Kevyn Nightingale

CRA is saying it’s just so big compared to everything else. The signing bonus in total is $70 million, almost $71 million and that cannot not be employment income. 71 million of the 77 million has to be employment income and that’s it.

Darren Coleman

How does this affect how you negotiate or how you talk to players about this?

Shlomi Levy

Until there’s a judgment on this, it definitely puts people on their back feet. I want to say only the first 15 million of the signing bonus is being contested here because the following bonuses were paid to him as a Canadian citizen and tax resident. So it’s not really contested. The bulk of the work I’ve done is mostly with Canadian athletes who are resident here. So we haven’t had any of these issues. We do deal with a lot of Canadian athletes who married American girls, so the complexity is still there, but I would say that a lot of free agents, especially when it comes to baseball, and even the CFL in Toronto, are going to be looking at this carefully.

Darren Coleman

Because as a group they have more Americans moving to Canada than hockey players, right?

Shlomi Levy

Correct. Look at Toronto. You’ve got Austin Matthews, who’s an American citizen and he’ll probably straddle that line. He’s never considered a Canadian tax resident. You’ve got some Europeans with Nylander in Toronto as well. Big contract, big signing bonuses. So a lot of people are going to be watching this, and the strategy for Canadian teams might change significantly depending on what this judgment produces.

Darren Coleman

I think fans are watching this because the tax thing can really affect the fortunes of how teams are going to be able to produce. Because if they can’t, if they’ve got such a huge tax hurdle, how are we ever going to recruit top talent if this is an issue?

Kevyn Nightingale

It is an impediment to hiring people, to doing business anywhere if you don’t know what the answer is going to be.

Shlomi Levy

In the US your individual tax rates at the federal level are low, and if you’re lucky enough to play in a state like Florida or Texas where there is no state tax, your maximum tax exposure is 37%. Now assume these guys are all making over a million bucks, so 37% versus 53.5%. There was an issue a few years ago in a Canadian team where a player was negotiating as an unrestricted free agent and ended up signing the same numerical deal, but one season less, with Dallas vs. the Canadian team, and everybody went up in uproars.

The argument is very simple. He was going to make net the same amount of money playing one year less. Agents and players are a lot more sophisticated. There’s a lot more that goes into negotiations, and not just the numerical value. 100 million in Montreal or Toronto is easily 85 million in the US, and add to that life, weather, taxes and probably paying less for the same amount of net money. At the end of the day, these athletes are phenomenal individuals. They’re well-tuned machines, but they also have an expiration date on their career, and they’re trying to optimize it.

Kevyn Nightingale

This is something many governments have trouble coming to terms with, and that is there are limits to tax. And this is the thin edge of the wedge, where you see at the top end, the talent is mobile. And you can’t just say, well, we’re going to raise their tax rates from 45% to 55% and we’re going to get 10 extra points. No. People respond. People respond to incentives.

And if you tell them you’re going to pay that much more here, they’ll say, I’ll go somewhere else where I can do better on a net basis. And that is not just the NHL and NBA and football and basketball and baseball. It is every sport, but it’s also more importantly in business. Business is more and more global, and employment is more and more global at the top end. Major Canadian corporations are hiring a CEO. They’re not just looking at Canada. They’re looking to the US as well. If you’re a new potential CEO coming up from the States you say, Well, I understand your taxes are that much higher. Pay me that much more if you want me. That makes the Canadian company much less competitive.

Darren Coleman

You run into a problem. One, it’s hard to recruit people in the lower-tax jurisdiction to come to our higher-tax jurisdiction. And then we have the way Canadians are taxed. I want to get into this because a lot of people don’t know this nuance. It’s easier for Canadians to leave our tax system. So we not only have trouble recruiting brainpower, but we also can lose talent and brainpower. It’s surprising to me how many people are surprised by this and it’s the difference between how Americans are taxed, which is on citizenship, and Canadians are taxed on residency.

Shlomi Levy

I want to go back to a statement made a bit earlier that one of the other big concerns we should have as Canadians is the attitude of our current government just grabbing as much as they can get. You look at the way the treaty works, and very often there’s a bit of IOU, you know, Canada to the US and US to Canada. It all works on an IOU system and it worked just fine until this current government came and started piling up all kinds of new catches and new grabs to make it much more difficult.

And the recent legislation they pushed forward about businesses and foreign affiliates doing business and foreign tax credits going up and down and the imposition it wishes to impose on dividends from a foreign affiliate and an extra 22% in Canada, and then one day issue a credit on extractions of dividends from that company. These are cash grabs that are telling a guy sitting in his office thinking about expansion to the US and thinking that he’s going to use corporate money and get that taxed like an individual. Next thing you know he says I’m not going to do it. And it takes away from our ability to expand our business and ideas into the US. Our Canadian government just wants to tax the jitters out of us. Continue Reading…

Retired Money: Tax Brackets, Income Thresholds, Inflation Factors & other things retirees need to consider going into 2025

My latest MoneySense Retired Money column looks at a variety of tax and savings limits changes that are effective early in 2025. Click on the highlighted headline for the full column: What retirees need to know about tax brackets for 2025.

As the column notes, at or near Retirement taxes and inflation are the two big threats to preserving enough wealth to last a lifetime.  The tax burden hits home with the annual tax-filing deadline in April, but the time to start thinking about the yearly ordeal is before year-end.

The complexity of this task is compounded by almost-annual changes to tax brackets, the Basic Personal Amount, OAS thresholds, inflation adjustments and much more. For starters, I recommend reading an excellent article by CIBC Wealth’s tax guru, Jamie Golombek, which appeared in the Financial Post here on Nov. 23rd, shortly after the Canada Revenue Agency released its new tax numbers for the year 2025.

 Let’s look first at inflation, the second serious scourge retirees face if they live long enough. Here, a useful tool suggested by certified financial planner Morgan Ulmer is Statistics Canada’s Personal Inflation Calculator, which lets you compare your personal inflation rate to the general CPI.

Ulmer, of Toronto-based Caring for Clients, sees the higher tax brackets and inflation adjustments as an “opportunity for retirees to build a savings reserve.” CPP is indexed to inflation yearly while OAS is indexed quarterly.  So “if a retiree is able to increase their spending at a rate that is less than CPI, the difference could be saved as an emergency reserve or invested in a TFSA.”

 Inflation and Tax Bracket changes

 Back to some key data cited by Jamie Golombek.  The inflation rate used to index 2025 tax brackets and amounts will be 2.7%: just over half the 4.7% in effect in 2024.  The good news is that the Basic Personal Amount (BPA) on which no federal tax is levied rises to $16,129 in 2025: It was $15,000 in 2023.

All five federal income tax brackets are indexed to that 2.7% inflation rate. In 2025, the bottom federal tax bracket of 15% will apply to incomes between zero and $57,375. The second lowest bracket of 20.5% will apply to incomes between $57,375 and $114,750. The 26% bracket applies to income between $114,750 and $177,882, while incomes between $177,882 and $253,414 will attract a 29% federal tax. After that the federal rate will kick in at 33%.

Below is a table summarizing that information prepared for MoneySense:

MoneySense.ca

 Don’t forget there will be additional provincial taxes on top of the federal haul, also indexed to inflation at various provincial rates.

 What is relevant for those in the Retirement zone is the higher threshold on Old Age Security: in 2025, according to Canada.ca, OAS begins to get clawed back for taxable income of $90,997.  OAS benefits disappear entirely at $148,451 for those aged 65-74 in 2025, and at $154,196 for those 75 or over. Note the OAS clawback is based on individual incomes, not household income.

Deferring CPP and OAS till 70

 Matthew Ardrey, portfolio manager and Senior Financial Planner for Toronto-based TriDelta Financial, agrees that tax brackets, whether federal or provincial, “become more of a consideration in retirement.” For many Canadians receiving employment income on a T-4, there is little we can do as retirees to keep income in the lower tax brackets. But there’s plenty to think about when considering tax minimization and decumulation strategies. Referring to Golombek’s article, Ardrey says that using federal brackets only, taxpayers can receive $57,375 of income and pay very low rates of taxation, especially when the $16,129 basic personal amount is considered.”

Retirees under age 70 can defer CPP and OAS until 70 and try to live on withdrawals from their registered plans instead. With no other income, taxpayers could have almost $50,000 of after-tax income, or $100,000 for tax-paying couples. Continue Reading…

Real Life Investment Strategies #5: Retirement Decumulation Strategies

Steps to Retire the Way you Want: Set Your Retirement Goals, Put your Money in the Right Places, and Optimize your Withdrawals

Graphic by Steve Lowrie: Canvas Custom Creation

By Steve Lowrie, CFA

Special to Financial Independence Hub

Most of us feel young well into our 60s (or even later) and retirement seems like a faraway concern for the distant future. However, thinking about your retirement early allows you to comfortably enjoy your later years no matter what your priorities are – leaving a legacy for your loved ones, travelling, spending time on hobbies close to home or any combination. Putting together a retirement income plan early gives you the best path to safeguard your financial freedom post-retirement.

Retirement income planning doesn’t mean constant worrying and going without today. It just means taking stock of where you are financially, where you want to be in the future, and setting up a plan to get there. That retirement plan could include setting up the right investment strategies now to allow you the flexibility you’ll need in the future to generate cashflow from the right places and pay the least amount of tax. It also could mean contributing regularly and consistently now so you don’t have to make up for lost ground in the future.

Let’s get into what retirement investment vehicles and strategies you have, how to think about your retirement priorities and goals, and how you can plan a decumulation strategy for the retirement you want and deserve.

Your Retirement Vehicle Options

When thinking about retirement vehicle options, I like to visualize pots or buckets of money; each of those pots represent a savings vehicle from which you can withdraw retirement cash flow. Whether it’s pots or jars or briefcases filled with cash that you imagine, here are the labels you can put on them:

It’s crucial to consider all of the different retirement “pots” you currently have or need set up. For couples, it’s also important to remember these options apply to both spouses which can be extremely advantageous for your retirement withdrawal plan.

Your Retirement Priorities & Goals

Once you’ve explored your retirement savings vehicle options, you’ll want to determine your priorities and define your goals.

It’s a bit of a balancing act where you might need to make some decisions to prioritize your goals. Do you:

  • Maximize your retirement income and fun (lifestyle needs, travel, etc.) OR
  • Leave a financial legacy for your family and loved ones OR
  • Focus on charitable donations

To help you prioritize your goals, we’ve got some great blogs on this topic to get you thinking:

Remember, it doesn’t necessarily need to be one goal vs. the other. However, you may need to consider how you can achieve all your goals, perhaps by weighting their importance (my retirement fun: 60, legacy for the kids: 30, charity: 10). Or you could consider how to distribute your specific investment “pots”, for example, you may choose to spend all financial assets and leave the kids the real estate.

A few more tips to help with your retirement goal prioritization:

  • Keep your retirement goals realistic – you’ll want to ensure you have the ability to reach your goals with highest probability.
  • Balance your spending, savings, and withdrawals to align with goals.
  • Review the location of your savings in the necessary “pots” to ensure you can meet your goals optimally.
  • Focus on minimizing tax – determine the best strategy for your priorities today and tomorrow. You can pay tax now or later (estate timing) or your plan can be to smooth out your tax outlay over time. This is a key consideration when allocating your savings into your investment vehicles.
  • Timing – as the old adage goes, timing is everything and I don’t mean market timing. From an investment perspective, the best approach is systematic and consistent contributions and properly planned withdrawals.
  • Be flexible – the longer you have between now and retirement, the more that things can change, including your goals and financial circumstances.

Retirement Decumulation Strategies in Action

Let’s look at how people just like you can implement these retirement decumulation strategies to reach their retirement goals.

The Accumulators: Suzie and Trevor Hall (When We First Met Them)

Financial Accumulators Suzie and Trevor Hall
  • In their late 40s
  • Still deep in their accumulation years
  • Two teenage children
  • Own a home, which is almost fully paid off
  • Have been good about living within their means and diligently saving
  • Hope to retire within 15–20 years
  • Want to fully fund their children’s education
  • Plan to complete home renovations before they retire

During their accumulation years, Suzie and Trevor followed advice from their independent financial advisor:

  • Start with planning, not investing.
  • Establish a spending plan.
  • Invest systematically.
  • Do a lifeboat drill.
  • Remember that it’s priced in.
  • Established an appropriate emergency fund and lifestyle reserve. Continue Reading…

Estate Planning Checklist for Entrepreneurs

Photo courtesy Pexels/Featured.com

By Robert Theofanis

Special to Financial Independence Hub

Estate planning is like going to the dentist. Everyone knows they should do it. But whether it’s getting your teeth drilled or contemplating your mortality, we’d all rather fill our time with just about anything else.

For entrepreneurs, this problem is even more acute. Your business depends on you, and high-priority items constantly appear at the top of your to-do list.

What I’ve found as an estate planning attorney is that my clients can get more done when we approach estate planning in a systematic way. This post contains an actionable plan for entrepreneurs like you to design and implement an estate plan.

I’ve organized the list by priority, with the most critical items first:

Obtain Term Life Insurance

If you have minor children, life insurance is the most important component of your estate plan. Most parents of young children simply haven’t had enough time to accumulate sufficient wealth to sustain a family without any additional income.

I like term insurance for this baseline protection because it’s cheaper than a permanent policy.

I also recommend that both parents have policies. Irrespective of who earns the income, both parents contribute to the household.

For the benefit amount, err on the side of more coverage and consider purchasing separate policies (e.g., two $1 million policies rather than one $2 million policy). This allows you to scale back the coverage amount without dropping coverage entirely.

If you don’t have children yet but are planning to, I still suggest getting coverage now. Life insurance premiums increase with age and pregnancy-related health issues may make it difficult to secure coverage later.

Create a Revocable Living Trust

A basic revocable living trust is the foundational legal document for an estate plan. Its purpose is to keep you and your property out of conservatorship and probate proceedings.

Included in this step is creating the other estate planning legal documents:

  • A pour-over will ensures that all property is distributed in accordance with the terms of your living trust, even if it’s inadvertently left out of the trust;
  • A durable power-of-attorney authorizes a financial agent to conduct transactions on your behalf if you’re incapacitated;
  • A medical directive authorizes a healthcare agent to make medical decision for you if you are unable to and specified your healthcare and end-of-life wishes (in some states, two separate documents are prepared for this purpose);
  • A guardian nomination appoints a guardian to raise your minor children if you are unable to.

Be sure to actually fund the trust! This is one of the biggest mistakes people make. This involves transferring title to real property, opening new financial accounts (bank, brokerage, etc.), and updating beneficiary designations.

Establish and Implement a Written Financial Plan

Estate planning is more than just creating a set of legal documents. It’s a multifaceted plan to achieve positive outcomes for you and your loved ones. So, while the first two items on this list are about limiting your downside, this item concerns your upside. Continue Reading…

Retired Money: A Canadian immigration success story

My latest MoneySense Retired Money column is a bit of a departure in that its focus is on 57-year old blogger and YouTuber Alain Guillot, who came to Canada from Columbia with nothing but entrepreneurial gumption and a dream of being part of the North America depicted on TV at home.

For the full MoneySense column, click on this headline: The first $100,000 is the hardest to save for newcomers.  

The re-election of Donald Trump is almost certain to make Immigration an even more contentious issue. However, as I am myself the child of (British) immigrants I am naturally sympathetic to those who are brave or desperate enough to leave the land of their births to find opportunities in North America.

Which is one reason that over the past year, I’ve been corresponding with an interesting blogger and former financial advisor, Alain Guillot, and occasionally republish his blogs on my site, Findependence Hub. It’s called simply AlainGuillot.com

           He aims to write at least one blog a week and has 600 subscribers on his YouTube channel,  where he is more than half way to being able to monetize it. Now Guillot has just self-published a short e-book entitled The Wealth Paradox: Navigating Money, Free will, and Success, which you can find on Kindle for a very reasonable price. The subtitle explains more: How unconventional thinking influences your Financial and Personal Life.

Side hustles and Entrepreneurism

           One reason Guillot got my attention in the first place was that he emigrated to Canada from Colombia, a place I once visited (San Andres). He soon discovered he was almost forced to become an entrepreneur in Canada. Continue Reading…