⏳Plus: Why Sundays are getting extra scary October 19, 2026 Sign Up | View online Canada’s Most-Read Financial Newsletter To quote the late great Biggie Smalls: mo’ money, mo’ problems — or at least mo’ stuff to take care of. Good news, though: the tribulations of the nouveau riche hold useful lessons for the rest of us, too. | Getty Images/Michael Ochs Archives In This Issue 8 min read The definitive to-do list for your new f**k-you money Plus! 🦄 An AI unicorn goes bust 👻 Sundays: now even scarier The Idea of the Week Stocks have been in a stealth bear market for months by Peter Arkle Note: TLDR is hitting your inbox a bit late today due to some necessary backend maintenance. Sorry about that! Today is the 39th anniversary of Black Monday in 1987, the single worst day in global market history, so maybe it’s apt that so many investors bolted upright this morning fearing a repeat — especially after last week’s unsettling double-digit chip-index plunge. Subtract AI stocks from the recent equation, though, and an interesting reality check emerges: we’ve already been in a bear market — a stealth bear market — for months, and those high-flying tech behemoths were just disguising it. Even prior to last week’s swoon, more than 80% of global stocks were in a drawdown. Big drawdowns. Close to half were more than 30% off all-time highs. But last week, while the giants buckled, 70% of the S&P 500 went up. Similar story with the TSX. All along, we’ve feared that this long rally was fragile, that if the AI supply chain slowed, global markets could convulse. But maybe the tech sell-off (which reversed a bit Monday morning) is also creating buying opportunities for more battle-tested corporate giants — Boeing, UPS, Pfizer, Nike, Disney — that mostly got ignored during the gold rush? Last week we got a strong case for both. TSX: +2.4% (+13.7% YTD) S&P 500: -1.6% (+11.4% YTD) What Happened Last Week Important A once-high-flying AI unicorn files for bankruptcy. Just five years in, popular chatbot company Character.ai filed for Chapter 11, with plans to sell US$20 million of its assets to Disney (which slapped it with a cease-and-desist last year). The platform once boasted 20 million monthly active users but has been marred by several serious lawsuits — and its bankruptcy docs, uncovered by 404 Media, paint a dire financial picture (e.g., on a monthly basis, the company’s US$10M AI compute spending dwarfs its revenue). While giants like OpenAI and Anthropic might be too big to fail, some doomers see Character.ai’s demise as evidence that smaller AI companies are running out of oxygen. The Canadian economy is looking a little K-shaped. For a time, economists seemed sure that Canada hadn’t caught the U.S.’s K-shaped affliction. But a new study from the C.D. Howe Institute reveals otherwise: while the 20% highest-earning households saved a third of their disposable income last year, the bottom 60% spent more than they made. We’re not in a broad debt crisis, the study’s authors say, but national averages conceal that low-income households and young people face growing financial strain. Interesting Tesla unveils the world’s first flying car that’s actually a rocket. Not the Tesla-SpaceX merger we were expecting (unless you saw this in 2019), but perhaps the one we deserve? The automaker’s Roadster 2.0 uses SpaceX thrusters to flip, hover, and land. Clown-prince-of-🤣 Elon Musk acquiesced that this is “not necessarily a safety-optimized car” but one that can do “crazy gymnastics” — you know, perfect for school drop-off. Even this dazzling bit of showmanship bored investors, though, as Tesla’s stock ended the week down 7.2%. It’s not just you: the Sunday scaries are getting worse. Turns out that post-brunch undercurrent of anxiety has only intensified as workloads get heavier and job security disappears! Some employees interviewed by The Wall Street Journal say they preempt their Sunday scaries by working a few hours on the weekend, and WSJ’s survey data shows those numbers are ticking up: over 10% of workers admitted they check work chats on Sundays, compared to just over 5% two years ago. Luckily, you have TLDR to look forward to… —Jenna Benchetrit The FOMO Index by Stacey Woods Important 🤬 Anthropic bans abusive behaviour toward Claude. Save that crap for your human assistant. Source 💕 New owners bought Bumble as “bet on the future of humanity.” So strangers sharing a grilled artichoke and never speaking again is the future of humanity. Source 📺 Dateline is getting a Canadian spinoff. Producers hoping there are still some variations of “Death in the Snow” they haven’t used. Source 🏙️ More and more older Canadians are getting into parkour, or, as younger Canadians call it, “taking the stairs.” Source Crash & Burn To the Moon 🧠 Research finds your mother’s cells can stay in your brain for life. They’re the ones that make you bring a sweater to the restaurant. Source 🍩 Tim Hortons won’t have to give man boat they erroneously said he won. Can continue giving him hot liquid they erroneously say is coffee. Source ❓ NYT reports that no one actually knows what “biweekly” or “bimonthly” means. Interesting reading if you’ve ever been bi-curious. Source 🐢 104-year-old Halifax tortoise resting comfortably after urinary stone removal. Says he can’t wait to get back to parkouring over some gravel. Source Who Cares? The Big Important Story You’re super rich all of a sudden. Here’s how to keep your head (and your wealth) Congrats — you just sold your next-gen AI company! Or maybe your reclusive Albertan oil-baroness Auntie Jane just left you all her money! Either way, you’re not just rich now, you’re crazy rich — so rich that managing your money now takes serious effort. How do you make sure your fresh pot of gold stays full? We asked Adam Fisch, head of family continuity and senior relationship manager at Our Family Office, and Danny Ritter, a partner and portfolio manager at Richter Family Office, for their advice. And if you’re not rich, (1) it’s always nice to dream, right? and (2) some of their advice applies to folks still building up a nest egg. [1] Hire an all-star financial team. Sudden wealth isn’t all champagne and caviar. It’s some of that, sure. But it can also be deeply traumatizing, says Fisch. Relationships change. Sharks circle. You’ll probably need to set up a family office to manage your wealth, pay your taxes and bills, chase away leeches, and guide your family through this new reality. Most home offices have a CEO, accountants, and investment analysts, and they typically charge 0.4% to 0.6% annually of assets under management. Lesson for the rest of us: Paying someone to manage your investments can be worthwhile — so long as you don’t overpay. Some actively managed mutual funds charge 2% or more annually. With that expense, if you invested $50,000 and got a 7% annual return, you’d end up with about $130,000 less after 30 years than if you had invested in a fund with a more reasonable 0.40% fee. [2] Decide what sort of HNWI (i.e., high-net-worth individual) you want to be. Ritter suggests asking yourself some big questions early on: what’s the purpose of this money? How do you see it impacting you and your family? Do you want to give most of it away, or build an empire? Your answers will shape your investment strategy. Fisch urges clients to think of wealth in three buckets: lifestyle, family inheritance, and charity. Lesson for the rest of us: Set clear goals so you (1) save enough, (2) don’t oversave and drive your family batty with austerity measures, and (3) use your extra money meaningfully. To point No. 3, one easy, tax-free way to help your grown kids is to gift them money to max out their TFSA. Or if you want to donate, you can open a Donor-Advised Fund (DAF) to get the tax write-off now and pick your causes later. [3] Get creative with your investments. When you’re in the nine-figure club, Ritter suggests thinking beyond bonds and stocks. “The ultrarich have access to more tools in the toolbox,” he says. “They’re investing in a startup or the development of an apartment building. They’re lending money in a deal” that can potentially deliver outsized returns. Lesson for the rest of us: Consider diversifying with alternative investments, REITs, etc. Many financial institutions now offer private-credit and private-equity funds to ordinary investors. You’ll have to lock up your money for years, but the returns could be hefty. [4] Treat yourself. Just don’t spoil yourself. Ritter doesn’t mind when moneyed clients buy flex pieces. “It’s important to buy that asset-slash-toy and get it out of your system,” he says. But remember: your swanky ski chalet and skippered yacht need regular maintenance, and those costs can quickly eat away at your wealth. Fisch’s rule: don’t do anything you can’t take back. “If you have $100 million, you can buy a $20,000 watch that you regret,” he says. “If you buy a $20-million jet, it’s a lot harder to offload.” Lesson for the rest of us: Watch out for lifestyle creep — i.e., letting luxuries become daily necessities — and keep your recurring expenses low. Delaying a $500/month car upgrade and investing it instead can leave you with $36,000 after five years at a 7% annual return. —Mike Newall Wisdom of X Thoughts on Today’s Issue? Love it Good So so This week’s newsletter contributors: Brennan Doherty (writer), Devin Gordon (writer), David Walters (writer), Stacey Woods (writer), Jenna Benchetrit (news writer), Ambrose Martos (fact checker), Ciara Rickard (copy editor), Maude Campbell (copy editor), Sara Black McCulloch (fact checker), Eva Grace Clement Cruz (specialist, product engagement), Lauren Edwards (production coordinator), Matthew Karasz (markets editor), Jared Sullivan (editorial lead), Peter Martin (senior editor), and Devin Friedman (editor-in-chief). Total returns shown in local currency, via TradingView. Wealthsimple Media Inc. 80 Spadina Ave Suite 400 Toronto, ON, M5V 2J4 Have questions? Contact us. VIEW IN BROWSER PRIVACY POLICY UNSUBSCRIBE TLDR is offered by Wealthsimple Media Inc. and is for informational purposes only. Any views expressed are those of the individual author and/or of Wealthsimple Media Inc., not of Wealthsimple Financial Corp or any of its other subsidiaries or affiliates. 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