Media Appearances

Life Insurance Proceeds, by David Rotfleisch

Section 160 of the Income Tax Act (the “Act”) broadens the power of the Canada Revenue Agency (CRA) to collect on income tax debts. Under section 160, if a person receives property from a tax debtor (the transferor), the transferee may inherit derivative tax liability.

Four tricks the wealthy use to reduce taxes that ordinary Canadians can try, too

You don’t have to be in the 1% to incorporate these tried and true tax strategies into your own planning

Practice Note No. 23: Tax Court of Canada tests Preliminary Ruling Docket

Thousands of appeals are launched in the Tax Court of Canada each year, some by self-represented taxpayers, some by accountants and the remainder represented by Canadian tax lawyers.The result has...

Lawyers who trade cryptocurrency: Remember the CRA

Bitcoin, the most well-known cryptocurrency, has recently been trading around $8,600, which is in the middle of its two-year range.

Estate Planning May Seem Like No Fun But It Has To Be Done!

Estate planning is one of those things that ALL of us need to do…but MOST of us want to avoid.
Let’s get real, this means talking about death and taxes and no one really wants to do that 😉 The thing is, it’s a VERY important part of planning for your loved one’s future financial security.

“The biggest mistake in estate planning is not taking into account the taxes payable on death.

There is a deemed disposition of capital assets when an individual dies which gives rise to a large tax owing in the estate. Bequests often do not take into account the net after-tax value of the estate.

How to minimize the cryptocurrency tax burden this tax season

Leading tax lawyer shares his strategy for protecting clients’ cryptocurrency gains from the CRA

Are the feds coming for your lottery winnings?

Reports suggest the Canada Revenue Agency is looking at taxing your poker winnings. Tax expert Nathaniel Hills explained the situation.

Experienced tax lawyer integral at outset of audit process

A recent Federal Court of Appeal (FCA) decision and the subsequent Canada Revenue Agency (CRA) response illustrates why an experienced tax lawyer should be retained early in the audit process, says Canadian tax lawyer David J. Rotfleisch. Read more

Man ‘moves’ to Ottawa in canoe to make a point. Canada Revenue accepts his expenses

It took John Konecny six days to journey from Whitby, Ont. to Ottawa through five provincial parks. He kept every receipt enroute and the CRA approved the deductions Read more

Contractors buying from Home Depot, other retailers beware — the CRA is coming after you

London Free Press and Post Media chain

“Contractors who are part of the cash economy and who have registered with Home Depot as commercial contractors should expect to be audited,” says David Rotfleisch, a tax lawyer at Rotfleisch & Samulovitch Professional Corporation in Toronto. Read more

Make sure your books are clean come tax time – or else

Earlier this year, Home Depot Canada commercial clients received a letter warning them that the Canada Revenue Agency (CRA) would be auditing their books in an attempt to uncover under-reported income by contractors and homebuilders.

Note: This is the online version. The same story will also appear in print, in the December 2019 / January 2020 edition of the magazine. Read more

CRA data mining sweep ‘ingenious and eminently logical’

Contractors who are part of the cash economy and have registered with North America’s largest home improvement retailer can expect to be audited by the Canada Revenue Agency (CRA), Canadian tax lawyer David J. Rotfleisch tells The Lawyer’s Daily. Read more

Tax audits likely coming for Home Depot commercial account holders

Earlier in September, Home Depot commercial credit cardholders received the following message from the home renovation behemoth: “We are writing to inform you that The Home Depot Canada is being compelled...Read more

The Canada Revenue Agency's VDP and the Gauthier decision

The Voluntary Disclosures Program ("VDP") allows taxpayers to correct inaccurate or incomplete information and disclosure information not reported in a tax return that had previously been filed or should have been filed. Those who file under a VDP application that is accepted by the Canada Revenue Agency ("CRA") would owe any taxes owing plus any applicable interest but would generally be provided relief from prosecution and, in some cases, interest and penalties that would have been applied if the taxpayer had not come forward under the VDP. As stated under subsection 220(3.1) of the Income Tax Act, the CRA can waive or cancel all or part of any penalty and interest otherwise payable within a 10-year limit from the relevant tax year. Read more

Full disclosure crucial when filing VDP amid program tightening

With the taxman recently taking a wider stance in aggressively pursuing past non-compliers, taxpayers making an application under the Voluntary Disclosures Program (VDP) should be sure to divulge all relevant information to their lawyer to avoid being reassessed beyond the scope of the program, says Canadian tax lawyer David J. Rotfleisch. Read more

Tax lawyer David Rotfleisch on latest Canada Revenue Agency communique

TORONTO – In MNR v Cameco Corporation (2019 FCA 67), the Federal Court of Appeal concluded that section 231.1 of the Income Tax Act simply does not give Canada Revenue Agency tax auditors “a general power to compel oral answers with respect to tax liability [para 34].” This means that a taxpayer need not acquiesce to an oral interview with CRA auditors. Read more

When can the CRA advance an alternative argument?

TORONTO – During a typical tax dispute between a taxpayer and the Canada Revenue Agency, the CRA will advance one or several grounds for the assessment or reassessment against a taxpayer. A ground for an assessment or a reassessment is the reason given by the CRA for assessing or reassessing the taxpayer for a different amount of tax owed than the taxpayer's self-assessed amount. The grounds relied on by the CRA have to be given in either the Notice of Assessment or Notice of Reassessment sent out to the taxpayer. In response, if the taxpayer is successful in disputing the ground or grounds of his or her assessment or reassessment, the CRA would generally have to vacate their assessment or reassessment against the taxpayer. Read more

A taxpayer's rights to interest from the Canada Revenue Agency

TORONTO– Under the Income Tax Act, RSC 1985, c 1 (5th Supp) ("ITA") 164(3) the CRA must refund interest at a prescribed rate based on the amount in respect of a taxation year that is refunded or repaid. (All future statutory references are to the ITA, unless specified otherwise.) This case is about whether the CRA is obligated to provide interest on a refund to Glatt ("taxpayer"), who had been assessed a penalty under the ITA's "planner" provisions. The issue has not previously been litigated. The court ultimately concluded [on May 24, 2019] the CRA's refusal to pay interest was unreasonable and the CRA must calculate and remit the interest owed to the taxpayer. Read more

Employers’ role in ensuring retirees understand income tax complexities

The complexities of income tax at retirement can come as a shock to pensioners, but most plan sponsors are providing limited assistance in helping their retiring employees deal with these issues. Read more

Results of CRA’s OTIP program ‘drop in the bucket’: Rotfleisch

While the first payments have reportedly been made to eligible whistleblowers under an income tax program aimed at catching Canadian taxpayers with unreported offshore income, the amount collected by the initiative so far has been disappointing, says Canadian tax lawyer David J. Rotfleisch. Read more

SCC decision will make it harder for tax evasion across provincial borders

The Supreme Court of Canada’s June judgment in 1068754 Alberta Ltd. v. Québec (Agence de Revenue) means that tax evaders will have no more luck hiding their assets extra-provincially than they currently do internationally.

Thoughts on the CRA and Canadian corporate tax gap

TORONTO – The Canada Revenue Agency recently published the corporate tax gap estimates, approximately one year following the publication of personal international income tax gap information. Read more

Tax court costs awards may prompt CRA to settle before trial

Parties who are successful against the Canada Revenue Agency (CRA) in tax court are entitled to the reimbursement of some costs, which may act as a strong incentive for the taxman to settle a case before trial, says Canadian tax lawyer David J. Rotfleisch. Read more

SCC deals a blow to tax evaders in Canada

The use of banks in foreign jurisdictions to hide information, assets and income from tax authorities worldwide, in non-tax havens such as Switzerland or tax havens such as the Cayman Islands, is almost as obsolete as buggy whip manufacturing. Not even supremely talented Canadian tax lawyers can overturn the tide of public sentiment against tax evasion. Read more

Beware the hidden tax bill on your office’s free lunches

Startups and small businesses offer plenty of enviable employee perks, but the battle over those taxable benefits can get ugly

Read more

Crucial for cryptocurrency holders to understand tax impact

With the Canada Revenue Agency (CRA) zeroing in on unreported cryptocurrency transactions over the last year, taxpayers who trade these assets should understand how they are viewed by the taxman.

Response time, dispute resolution should be addressed as part of CRA consultation: lawyers

The Beatles may have lamented the fact the taxman in the U.K. didn’t like you giving your opinions, but the Canada Revenue Agency (CRA) has launched a public consultation process with an eye to getting input on how it operates and how it can improve the services it offers.

Canada losing multi-millions in e-commerce taxation

Toronto tax accountant and lawyer David J. Rotfleish predicted the attack ... is coming for online retailers," Rotfleisch wrote that CRA "guidelines ...

Tax slashing tips for Canadian lawyers

David Rotfleisch,, is the founding tax lawyer of Rotfleisch & Samulovitch P.C., a Toronto-based boutique tax law firm.

7 ways to file your taxes for free in Canada

Audit protection works like insurance against the possibility of a CRA audit, according to Toronto tax lawyer David Rotfleisch. Most taxpayers ...

As a startup, are you taking full advantage of tax breaks?

David Rotfleisch is the founding tax lawyer of Rotfleisch & Samulovitch P.C., a Toronto-based boutique tax law firm. We all have to pay our fair ...

What the media missed in the Auditor General’s CRA report

Canada Revenue Agency does not accurately measure its performance.

How effective is the CRA at closing Canada’s tax gap?

How good is the Canada Revenue Agency at closing the tax gap? We’ll find out this year from the Parliamentary Budget Office if the CRA has indulged in PR spin.

Tax Implications Of QuadrigaCX Lost Cryptocurrency Keys

QuadrigaCX, Canada's largest cryptocurrency exchange, lost its founder and chief executive Gerald Cotton on December 9, 2018.

Taxation Of Gambling And Poker Winnings – A Toronto Tax Lawyer Guide

In the Canadian income tax system, only income which can be traced from a 'source' is considered taxable.

Feds consulting on changes to ‘unfair’ salary overpayment policy

The federal government is proposing changes to tax rules so people who receive a salary overpayment will only have to pay back the net amount to their employer, a move experts...

Is the CRA’s public shaming an effective deterrent of tax evasion?

The Canada Revenue Agency publicizes tax evasion convictions as part of the concept of general deterrence.

Incorporating your law firm a great tax planning tool

Want to reduce the taxes you pay in 2019? Consider incorporating your legal practice.

Even the big stars are in crosshairs of the tax authorities

Famous Chinese actress Fan Bingbing and one of the stars of the 2014 film X-Men: Days of Future Past, one of the highest-paid actresses in the world, has been ordered to...

Auditor General Slams CRA For Unfair Treatment Of Taxpayers

The Auditor General of Canada released its audit report on the Canada Revenue Agency's tax compliance efforts.

Too early to tell effectiveness of Canada’s anti-tax avoidance measures, says lawyer

The federal government is trumpeting its progress in combating tax avoidance, but a tax lawyer is saying the moves are in their infancy and the evidence is not there yet to..

Mens rea for tax evasion: R v. Patry

In R v. Patry 2018 BCSC 1524 the Supreme Court of British Columbia reaffirms that the proper test for the mens rea analysis for tax evasion is a knowledge-based approach

Canada: Guilty Of Tax Evasion Or Simply Tax Planning?

In R v Patry 2018 BCSC 1524 the Supreme Court of British Columbia (the "Court") found that Mr. Patry did not have the requisite culpable state of mind for a tax evasion conviction.

Secrets of the carbon tax

Coming soon to a province near you, unless it is felled by a constitutional challenge, is a new hidden tax designed to combat global warming.

Is the CRA treating you fairly?

The Auditor General says how you're treated by CRA depends on where you live and which auditor you're dealing with. Open lines with a tax lawyer and a chartered professional accountant.

Aitchison: A distasteful but correct Tax Court decision

In the finest tradition of the Canadian judiciary, the Tax Court of Canada recently ruled in favour of a lawyer who had not paid income tax since 1992, and owed almost $2.1 million to the Canada Revenue Agency.

What does carbon pricing mean for you?

Prime Minister Trudeau announced on Tuesday the Liberals' federal carbon tax and rebate plan to tackle climate change, breaking down how pollution pricing will affect Canadians' pocketbooks in 2019 and onward. But, what does it mean for your family?

Unemployed man told to pay thousands of dollars in taxes for government EI mistake

Tax lawyer David Rotfleisch says it can be very difficult for people to go up against the CRA, especially if they can't afford professional help.

Hitting 'Goldilocks number' on taxation of cannabis key to reducing black market

Tax lawyer David Rotfleisch of said the government’s proposals are “entirely akin” to the tobacco tax, in that the taxes are being calculated per gram of cannabis, as it is for tobacco, and there are different provisions for stamped and unstamped products.

“There is nothing really exciting here,” he said. “This is part of the point of the marijuana legalization — to get rid of the whole criminal justice cost of enforcing silly laws and to raise revenue and put the money into the hands of government, instead of organized crime.”

Fighting the Canada Revenue Agency no longer like fighting city hall

It used to be that fighting the Canada Revenue Agency (CRA) was like fighting city hall — soul-sucking and futile — and the CRA could not be held liable for negligence.

Lax corporate disclosure aids money launderers: CD Howe report

However, the point is entirely correct about corporations: that there is no Canadian requirement for disclosure of beneficial ownership of corporate shares or of reviewing for whom a nominee director acts. The recommendation is that the federal government, in collaboration with the provinces and territories, establishes a central publicly accessible beneficial ownership registry of corporations and certain trusts. This recommendation has serious adverse privacy implications.

Ontario faces 'uphill battle' in fight against carbon tax: experts

Tax lawyer David Rotfleisch of noted the Constitution Act, 1867 gives broad powers to the federal government to implement taxation, and the only path forward for Ontario and Saskatchewan is to say the legislation is not a tax but a regulatory scheme.

Flawed Questions Inevitably Yielded A Flawed Survey At CRA

The recently released survey of all employees at the Canada Revenue Agency (CRA) conducted by The Professional Institute of the Public Service of Canada (PSC), the largest union in Canada representing federal government professionals, has as much bona fides as the 1949 advertising campaign that boasted "more doctors smoke Camels than any other cigarette."

David on Newstalk 1010

Barb DiGiulio, host of the popular daily radio talk show “The Nightside,” talks to David Rotfleisch about it is easier for corporations and wealthy individuals to evade or avoid tax responsibilities than it is for average canadians “YES,” says David.

International coalition investigating cryptocurrency tax evasion, money laundering

The Wild West days of cryptocurrency and tax evasion are on the wane. Bitcoin, ethereum, dash and other digital currencies are now firmly in the crosshairs of worldwide tax authorities: the burning issue, of course, is the loss of tax revenue occurring from unreported cryptocurrency transactions.

It’s June – where’s my tax refund?

Ryan, a Toronto taxpayer who asked to be mentioned only by first name, was counting on a $10,000 tax refund to help pay for his upcoming wedding in July.

A Toronto realtor has been named in whistleblower's list of secret Swiss bank accounts

“In this case, clearly they have criminal prosecution in mind,” one of Stankovic's lawyers, David Rotfleisch, told The National Post. Stankovic herself declined to speak about her case. In the grand scale of the revelations contained in the Falciani leak, Stankovic seems a minnow among sharks.

The Canada Revenue Agency's Battle Against Taxpayers Has Just Begun

The Canada Revenue Agency's Battle Against Taxpayers Has Just Begun. CRA is good (sort of) at collecting money owed; when it comes to administering programs that pay money out, not so much. David J. Rotfleisch Canadian Tax Lawyer, Rotfleisch & Samulovitch PC, explains that the CRA has extraordinary powers to abuse taxpayers.

A world of difference between CRA civil and criminal tax audits

The Income Tax Act is clear on Canada Revenue Agency civil and criminal audits. But what happens when the goal of a CRA civil audit is to lay criminal charges? Canadian tax lawyer David Rotfleisch explains that taxpayers have rights.

So You Can’t Pay Your Taxes To The Canada Revenue Agency — Now What?

Be sure that you file your tax return on time even if you cannot afford to pay even $1 of your tax liability. David J. Rotfleisch Canadian Tax Lawyer, Rotfleisch & Samulovitch PC.

New tax rules for lawyers: Valuate work-in-progress

So, to take into account these new rules, lawyers will have to carry out a valuation of the actual cost of providing their legal services. This is a technical and complicated valuation in order to determine all of the cost elements that go into the services rendered.

5 things you need to do to win (or survive) a CRA tax audit

So you’ve filed your taxes and received your notice of assessment, but now there’s another letter from the Canada Revenue Agency (CRA) in your mailbox with a request to see more of your paperwork. What do you do?
Most likely, what you’re looking at is an inquiry notice, said David Rotfleisch, owner of Toronto tax law firm Rotfleisch and Samulovitch.

The CRA thinks you're evading taxes: Now what?

Canadian tax lawyer David Rotfleisch explains that there are three ways that Canadians can be audited: 1) you are named in the Panama Papers or the Paradise Papers as a suspected tax evader, 2) you are named by an anonymous whistle-blower, or 3) you raise the suspicion of a CRA tax auditor.

Budget tries to keep it simple with two proposed tax changes

The first change reduces the amount that can be claimed for the small business deduction for CCPCs based on the amount of adjusted aggregate investment income that it earns.

Further complicating the tax system, the second change introduces a second RDTOH account in order to limit the use of RDTOH to non-eligible dividends for private corporations.

Ottawa owes apology to B.C. couple after malicious tax prosecution ruling: lawyer

David Rotfleisch, a tax lawyer with, said he could not recall any successful malicious prosecution cases dealing with a tax issue before, but said the decision was “a punch in the face” for the CRA.

“If you go through the whole history [of the Samaroo case], it’s a typical case where a CRA person makes up their mind — and that’s it, they’ve made up their mind about what’s going on and they’re not prepared to entertain any other options,” he said. “In general I have to say that I have seen outrageous behaviour in many cases by CRA people and clients often enquire about whether they have the ability to sue CRA.”

The culture at the CRA is changing – and we should all be concerned

Personal finance expert and occasional guest Globe and Mail columnist Tim Cestnick quotes prominent Canadian tax lawyer David Rotfleisch about the worrying culture of Canada Revenue Agency (CRA).

David on Newstalk 1010

Veteran broadcaster Barb DiGiulio talks to David Rotfleisch about his very first blog for The Huff Post, about Canada Revenue Agency (CRA). “It’s broken,” says David.

Take It From A Tax Lawyer: The Canada Revenue Agency Is Broken

Having dealings with CRA for three decades, you form an opinion. I wish I had good news for Canadian taxpayers, writes David Rotfleisch in his inaugural Huff Post blog.

Bitcoins, bubbles and your burden to the CRA

The situation for an investor in cryptocurrency is very different. Bitcoin is considered by CRA to be akin to a commodity. There is no requirement to account for increases in value of commodity (or other) investments as prices fluctuate.

David on Newstalk 1010 with Jon Pole

Jon Pole, host of Newstalk “Pole Position” in Montreal, talks to David Rotfleisch about how Bitcoin is taxed.

The argument for hanging out your shingle on a professional corporation

Setting up a law practice as a professional corporation is “a slam dunk, absolutely the way to go,” advises chartered professional accountant and tax lawyer David Rotfleisch in Toronto. “Incorporate from the get-go.” Rotfleisch, the founding lawyer of Taxpage, says that one of the most important reasons is that “you have the ability to set up an individual pension plan and contribute far more to the pension plan than you would through an RRSP.”

U.S. tax law reform means Canada has lost ‘competitive advantage’: experts

David Rotfleisch of called this measure “quite an outrageous move” but “pretty typical of the way the U.S. treats its citizens who are resident in the rest of the world.”
“If I have to specify a single most pervasive effect on Canada, that’s it,” he said. “U.S. citizens living anywhere in the world are required to file U.S. personal tax returns and these tax reform measures are possibly a big whammy for them.”

The Tax Court of Canada’s exclusive jurisdiction

The issue of choosing the correct court has been a problem for lawyers for 200 years, and it remains a concern when dealing with the Canada Revenue Agency (CRA).

Opinion: Tax evasion should be as stigmatized as drunk driving

While there's a growing awareness tax evasion is not a victimless crime, as taxpayers have to make up the shortfall, it's still common.

More about what every lawyer should know about year-end tax planning

Canadian tax lawyer David Rotfleisch writes “More about what every lawyer should know about year-end tax planning”.

Tax tips every lawyer should implement now

Canadian tax lawyer David Rotfleisch gives “Tax tips every lawyer should implement now”.

Is the taxman spying on your social media?

CJAD radio personality Leslie Roberts talks to Canadian tax lawyer David Rotfleisch about: “Is the Taxman spying on your social media?”

Changes To Income Sprinkling Rules

CTV News Channel anchor Scott Laurie talks to Canadian tax lawyer David Rotfleisch about the new rules for income splitting/“income sprinkling” introduced by Finance Minister Bill Morneau. These are the revised rules for income splitting, after the huge public backlash in September 2017.

How bitcoin is taxed in Canada

BNN anchor Greg Bonnell talks to Canadian tax lawyer David Rotfleisch about Bitcoin and other cryptocurrencies are tax by Canada Revenue Agency (CRA).

Canada’s top 1% collected more than 11% of the country’s income in 2015

The share of income flowing to the top one per cent of Canadian tax filers increased by almost one percentage point between 2014 and 2015, the first increase since 2006, Statistics Canada said on Wednesday.

PayPal to disclose the names of those Canadians who use the payment platform for conducting business

Barb DiGiulio, host of the popular daily radio talk show “The Nightside,” talks to David Rotfleisch about the court order that Canada Revenue Agency (CRA) obtained against PayPal to disclose the names of those Canadians who use the payment platform for conducting business. If you are a business that uses PayPal for payment and you are not disclosing the income nor remitting the GST/HST, you may get audited. If you use PayPal to sell items around your house, you don’t have to worry.

Paradise Papers: Did Canada actually make it easier to stash money offshore?

The latest massive leak of offshore financial documents, the so-called Paradise Papers, has put the spotlight on Canada.

Law society faces pushback on diversity initiative, to host information session

“I can’t imagine how it could be more negative. There are so many analogies: the Thought Police comes to mind from 1984, McCarthyism and Catch-22 loyalty oaths. This really is a Big Brother imposing thought requirements on its members,” said David Rotfleisch, of Rotfleisch & Samulovitch Professional Corporation Barristers & Solicitors.

Opinion: Gambling, money laundering and Hawala are key ingredients to a casino stew

“I’m shocked, shocked, to find out gambling is taking place here,” says Captain Louis Renault (Claude Rains) to Rick (Humphrey Bogart) in the 1942 classic movie Casablanca, having been told by the Gestapo to shut down the club and as he accepts his cut of the gaming winnings.

Backlash prompts Morneau to backtrack on proposed small business tax changes

Last week saw as many new tax changes, outside of a budget, as I can recall in my 30 years of practising tax law.

Part 3 - Tax treatments of professional corporations: How to change

An incorporated law practice enjoys the benefit of the small business deduction. This means that for active business income of up to $500,000, there is a federal and provincial tax reduction. In 2017, the combined federal and Ontario tax rate on active business income is 15 per cent. Contrast this to the top personal marginal tax rate in Ontario of almost 54 per cent. Other provinces have similar discrepancies between active business earned in a corporation and personal tax rates.

Part 2 - Tax treatments of partnerships and LLPs

A partnership keeps its own sets of books and has to prepare its own set of financial statements. As with all professionals, as a result of the federal budget changes in March 2017, it will now have to value work in progress (WIP) in computing income. It is also required to maintain a calendar year-end.

The Night Side - Changes in Income Splitting between spouses

Barb DiGiulio, host of The Nighside, talks to David about the changes in income splitting between spouses or to split shares in a corporation.

Liberal tax changes would spark exodus of Canadian Entrepreneurs

“I fully expect to prepare a memo for him about becoming non-resident,” writes Canadian tax lawyer David Rotfleisch on Jon Chevreau’s Findependence Hub. In other words, if enacted into law, tax changes proposed by Minister Morneau would cause entrepreneurs to pack up and leave Canada for more tax-friendly jurisdictions.

Part 1 - Tax treatments of sole Proprietorships and Associations

Tax treatments of sole proprietorships and associations – The new tax columnist for The Lawyers Daily, (a LexisNexis publication), David Rotfleisch explains how sole proprietorships and ‘in association’ structures are taxed in Canada. Part 1 of 3.

Anthony Furey with David Rotfleisch

National Post Radio Host Anthony Furey talks to David Rotflesich about the Federal government’s proposed tax changes on corporations including: income splitting and taxing income inside a corporation. Effectively, these are small companies—with between 1 and 100 employees—with the house frequently mortgaged to provide capital to the business (and putting capital at risk) and the owners working long hours (even without pay). More than 70% of Canadians work in very small companies. These tax changes would penalize families, which are the economic engine of Canada.

Morneau's tax changes are so complex and unfair, they'll turn accountants bald—and rich

If the Liberals implement their tax proposals, you can expect less investment and more entrepreneurs leaving for business-friendly jurisdictions, writes David J. Rotfleisch.

The Night Side - Canadian federal government’s proposed changes to the Tax Act

Tax lawyer David Rotfleisch talks to Barb DiGiulio on “The Night Side,” Newtalk1010, about the Canadian federal government’s proposed changes to the Tax Act, closing loopholes of “income sprinkling” [income splitting] and the lifetime capital gains exemption, involving gifting shares to family members.

Proposed changes to the CRA’s Voluntary Disclosure Program will kill it

Last month, the Canada Revenue Agency announced radical proposed changes to the Voluntary Disclosure Program (VDP).

Ottawa announces plans to close tax loopholes

Business News Network (BNN)

Ottawa's proposed taxation changes may do more harm than good, experts say

The federal government is proposing changes to Canada’s tax system to reduce loopholes they say are giving unfair advantage to high-income earners, but tax professionals say the changes may end up doing more harm than good.

Federal government warned about perils of tightening tax amnesty program

Within weeks, Ottawa is expected to unveil proposed restrictions to an income tax amnesty program that has raked in millions for federal coffers, but experts are warning the government to tread carefully so that the changes don't siphon off the revenue flow.

Federal government warned about perils of tightening tax amnesty program

Within weeks, Ottawa is expected to unveil proposed restrictions to an income tax amnesty program that has raked in millions for federal coffers, but experts are warning the government to tread carefully so that the changes don't siphon off the revenue flow.

Federal government warned about perils of tightening tax amnesty program

Within weeks, Ottawa is expected to unveil proposed restrictions to an income tax amnesty program that has raked in millions for federal coffers, but experts are warning the government to tread carefully so that the changes don't siphon off the revenue flow.

Federal government warned about perils of tightening tax amnesty program

Within weeks, Ottawa is expected to unveil proposed restrictions to an income tax amnesty program that has raked in millions for federal coffers, but experts are warning the government to tread carefully so that the changes don't siphon off the revenue flow.

Federal government warned about perils of tightening tax amnesty program

Within weeks, Ottawa is expected to unveil proposed restrictions to an income tax amnesty program that has raked in millions for federal coffers, but experts are warning the government to tread carefully so that the changes don't siphon off the revenue flow.

Federal government warned about perils of tightening tax amnesty program

Within weeks, Ottawa is expected to unveil proposed restrictions to an income tax amnesty program that has raked in millions for federal coffers, but experts are warning the government to tread carefully so that the changes don't siphon off the revenue flow.

Liberals should tread carefully on restricting income tax amnesty, say experts

But tax lawyer David Rotfleisch said the government shouldn’t make any changes that would toughen the program.

Here are the Canadians most likely to get a tax audit this year

It’s every taxpayer’s worst nightmare: A notice from the Canada Revenue Agency (CRA) informing you that you’re going to be audited.

Evading taxes will land you in hot water

The restaurant business is a difficult gig fuelled by entrepreneurs’ passions and one that can be made even tougher when restaurant owners give in to the temptation of the underground economy. That’s like going from the frying pan into the fire.

CRA uses social media to catch tax cheats

These days, the CRA is monitoring the social-media accounts of suspected tax cheats. The CRA now also uses “text analytics” to help detect new tax-avoidance schemes. So, what Canadians post on Facebook, Twitter or other social media can and will be used by the CRA to help them determine if a Canadian taxpayer is reporting all their income.

What the CRA can and can’t do with your data and social media accounts

The CRA doesn't monitor the public's social media accounts without a reason -- but might take a peek at specific users' activity as part of audit investigations.

Airbnb: 3 things you need to know at tax time if you rent out your home

Income earned by renting out your home through Airbnb must be declared on your income tax return.

Self-employed? Here are 6 steps to get your taxes right

Being your own boss. Working as much you want, when you want. Building something from the ground up that’s truly yours. There are many things to love about being self-employed.

Raid on accounting firm highlights lack of accountant-client privilege

A recent CRA raid on a Halifax branch of Grant Thornton emphasizes a key difference between lawyers and accountants in terms of the protection afforded client files.

Top 5 Income Tax Stories of 2016

In a special to the Financial Independence Hub, David J. Rotlfleisch gives his “Top 5 Income Tax Stories of 2016.” From the Panama Papers, to fraudsters impersonating CRA officers and threatening Canadians with jail time (and demanding payment in iTunes gift cards!), to a whopping €13bn Apple tax debt to Ireland, it’s been a crazy tax year.

Donald Trump’s $916-million tax writeoff is equitable, even in Canada

Recent reports that Donald Trump declared a $916-million (U.S.) loss on his 1995 income-tax returns and speculation that he could have avoided paying any federal income taxes for up to 18 years resulted in much spin by both Republicans and Democrats, but not a lot of tax policy analysis or understanding.

How to avoid tax traps: A guide for condo flippers

What does Canada Revenue Agency say about reporting revenue from condos? Here’s an easy guide for condo flippers to prevent problems with the Canadian Tax Man.

Tax evasion schemes land “De-taxers” in jail

When “de-taxers” use best business practices such as franchising and friends and family of multi-level marketing (MLM) techniques, you know that even fringe thinkers are watching and learning from the likes of “Dragon’s Den” and “Shark Tank.”Read more

Carrick Talks Money: What if I haven’t filed a tax return for years?

Canada Revenue Agency’s voluntary disclosure program allows delinquent taxpayers to “come in from the cold.” You won’t be charged penalties and you will not be prosecuted. Plus, you may get a reduction in interest for the amount of tax owing. To take advantage of this, you must first file the Voluntary Disclosure Form, and then file the delinquent tax returns.

Carrick Talks Money: What Can I do about a Wrongful or Unfair Tax Assessment?

If you have been wrongly or unfairly assessed, in other words CRA believes you owe more tax, you have 90 days to file a Notice of Objection. “Don’t wait, and jump right on it,” says David Rotfleisch. Plus, other tips for a tax appeal.

Carrick Talks Money: I’ve been hiding money from CRA – how do I come clean?

If you’ve been hiding money from Canada Revenue Agency (CRA), or just not declaring all the money you make to CRA, David Rotfleisch outlines the proactive steps to take. It’s called voluntary disclosure.

CRA Plans 'Lifestyle Audits' in Vancouver as Part of Real Estate Probe - Newstalk 1010

‘Lifestyle audits’ are audits where CRA looks into why it is that you are making very little money and yet living in a mansion, driving an expensive car, and taking trips around the world. Sometimes, the wealthy buy homes for their children. Other times, real estate is frequently used to launder the proceeds of crime.

CRA Targeting Unregistered, Small-Town Contractors In Tax Evasion Crackdown

The Canada Revenue Agency’s continuing campaign against the underground economy has come to roost in small-town Canada,Read more

Big Crack-Down by CRA on The Underground Economy- Newstalk 1010

“The three areas they are focused on are: construction, retail sales and food service (restaurants, food trucks),” says David Rotfleisch to Barb DiGiulio on The Night Side. CRA is getting creative about people who are unregistered builders. CRA also looks at municipal building permits, to see if builders are properly registered and paying taxes. Lastly, they are actively data-mining social media for irregularities, such as builders who claim to not have much business but post a photo of their new Bentley on Facebook.

Eight Things That Can Trigger a Tax Audit by CRA

“Help! I’m being audited,” are dreaded words uttered by Canadians. They are especially dreaded by business owners because an audit means extra work and extra accounting costs.Read more

The Night Side - Interview with David Rotfleisch

Barb DiGiulio, host of “The Night Side” on Newstalk 1010, Toronto’s largest talk radio station, talks with David Rotfleisch about what the Panama Papers searchable database (unveiled on Monday, May 9, 2016) means to 625 Canadians who have offshore accounts and to Canada Revenue Agency that is investigating these accounts. “It is becoming socially unacceptable for people to not pay their fair share of taxes,” says Rotfleisch.

The Night Side - Interview with David Rotfleisch

The 2016 tax deadline is almost here. David Rotfleisch answers listeners’ tax questions on “The Night Side,” with Barb DiGiulio on Newstalk 1010.

Big changes in tax return can increase chances of audit: experts

Even if people have done nothing wrong, there is little that can compare with the dread that an audit by the Canada Revenue Agency can cause.Read more

Big changes in tax return can increase chances of audit: experts

Even if people have done nothing wrong, there is little that can compare with the dread that an audit by the Canada Revenue Agency can cause.Read more

Big changes in tax return can increase chances of audit: experts

Even if people have done nothing wrong, there is little that can compare with the dread that an audit by the Canada Revenue Agency can cause.Read more

Big changes in tax return can increase chances of audit: experts

Even if people have done nothing wrong, there is little that can compare with the dread that an audit by the Canada Revenue Agency can cause.Read more

Panama Papers: Spotlight on the wealthy, powerful - Toronto Tax Lawyer Comment

A leak of 11.5 million documents from a Panama-based law firm offers a glimpse into the shadowy world where the rich and powerful hide their money, raising sharp questions about the use of shell companies that obscure the identities of their true owners.

The Night Side - Interview with David Rotfleisch

As we approach the tax deadline, we talk all things taxes with David Rotfleisch, Tax Lawyer and Chartered Accountant.

Biggest mistakes people make on their income tax returns

There are lots of common mistakes people make when filing their taxes. One of the most common is, people who forget to declare offshore pensions.Read more

CRA targeting online income

Income from all business sources is taxable in Canada.There is no difference in the tax treatment of rental income from Airbnb or salesRead more

“Top 10” Early Tax Planning Tips for 2016

While tax season for calendar 2015 is just around the corner, the best time to influence your tax position for calendar 2016 is: right now. Here are the “Top 10” early tax planning tips for 2016 to help reduce your tax, contribute to your RRSP, help out family members, and also support your favourite charities.Read more

Judges affirm that Canada Revenue Agency has ‘duty of care’ to taxpayers

Two appellate court rulings confirm that the Canada Revenue Agency is not at liberty to intimidate and threaten taxpayers and must take appropriate care in how it treats them.Read more

The Night Side - Interview with David Rotfleisch

We talk to David Rotfleisch, Founding Lawyer/Owner at Rotfleisch and Samulovitch and Chartered Accountant about a report that Uber will be audited after the CRA took the ride-share company to court, to force it to open its books.

Focus: Law Firms Miss Advantage of Professional Corporations

Since 2001, incorporation for law firms has been a possibility. Despite its advantages, only a relatively small proportion of law firms that could benefit from incorporation have in fact done so.Read more

The Night Side - Year End Tax Planning

We talk to David Rotfleisch, Founding Lawyer/Owner at Rotfleisch and Samulovitch and Chartered Accountant about how you can save taxes with the help of year end tax planning.

David on The Night Side

We talk to David Rotfleisch, Founding Lawyer/Owner at Rotfleisch and Samulovitch and Chartered Accountant about taxes! We talk expenses you can write-off as a small business owner, should you lease or finance your vehicle, and more!

Taxing changes

Looming changes to the Income Tax Act introduce a “whole new world” to the future of estate planning in Canada, and the additional tax cost could be $10,000 to $20,000 per year for each trust, estimates David J. Rotfleisch.Read more

CRA says you can claim medical marijuana on your taxes

The Canada Revenue Agency has confirmed that it will allow the costs of medical marijuana purchased from a licensed producer as a medical expense despite the fact that the Income Tax Act does not as yet recognize the enabling legislation.Read more

Tax Information for the incapacitated and their Substitute Decision Makers

Listen to David J. Rotfleisch in an exclusive podcast for caregivingmatters discussing incapacity and substitute decision makers. He clarifies that incapacity does not affect income tax filing and record keeping requirements.

CRA’s non-existent $4-billion tax loss

The headlines last month claiming that Canada Revenue Agency wrote off at least $4 billion in debts in the last two years may not tell the full, or an accurate, story.Read more

David on The Night Side


Introduced by radio host Barb DeGiulio on her nightly show “The Night Side,” as the man who ‘makes tax fun,’ is tax lawyer and chartered accountant who answered listeners tax questions for 90 minutes. There were several questions on TFSAs, what to do if you get audited, and collection tactics of Canada Revenue Agency (CRA).

NEWSTALK 1010 : Interview with David Rotfleisch

Here's the low-down on this year’s tax changes and things to know about filing your taxes online with David Rotfleisch, Tax Lawyer and Chartered Accountant.

NEWSTALK 1010 : Rotfleisch - 20150209

Offshore Bank Secrecy is Dead

Large recent fines on banks have spooked othere major banks into imposing strict compliance requirements on their customers holding offshore accounts.

Rulings on CRA general duty of care a positive development

The Canada Revenue Agency has historically had a wide prerogative in its interactions with Canadian taxpayers.Read more

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