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Good afternoon everyone.

If you’re interested in learning more about the topic of today’s newsletter, our country’s new sovereign wealth fund, tune into Milk Bag’s first Substack live at 3:30 p.m. ET, where I’ll be unpacking the details with University of Toronto economics professor Joseph Steinberg.

And if you’re just here for the Aritzia and Matty Mat…

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Good afternoon everyone.

Yesterday evening started with dinner at SARA and ended with an event at the Park Hyatt hosted by Knightcap Chess Club. Taylor Harrison, the founder, and I recently connected after he complimented Milk Bag’s rebrand, and he clearly has good taste because this was a swanky as heck chess event. His team hosts meet-ups across major…

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Good afternoon everyone.

Please continue to send me photos with your Milk Bag mugs at home or, in the case of the photo below, out on the town with you—it’s so cool to see. For readers who ordered one over the weekend, I have either shipped them to you or, if your name is Joe, left one on your porch on my way in to work.

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Good afternoon everyone.

On Tuesday night, I teamed up with Back Forty and Maple to host a launch party at the Ace Hotel Toronto. A recent rebrand felt like a good excuse to take things offline, and I’m so happy we did.

Milk Bag filled the room with founders and builders who drive its coverage, editors and creators who, I think, own the future of Canadian media, and advisors and partners doing god's work behind the scenes.

I caught up with from Substack, media entrepreneurs like and , writers like and , and founders like Drummond Munro, Rachel Wong, and Krys Lunardo.

Guests were taken care of for their post-power hour wind down thanks to Bathorium, Formula Fig and Sleep or Die. A huge thank you to Fairgrounds and Oyster Group for their support in making this happen too.

That brings me to today’s newsletter. Three weeks ago, I asked and if they’d help me realize a vision of creating a print edition for the event. They were crazy enough to say yes, and we pulled it off.

Below are excerpts from that edition. I hope you have as much fun reading as we had writing.

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Today’s edition is focused on media news because between the Weston family putting millions of dollars into a digital media start-up and a Canadian billionaire buying a stake in The Economist Group, there’s a l…

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In case you missed it, last night I posted this update to Milk Bag’s Instagram page:

This partnership caught my attention because it’s rare to see American companies put this much effort into a Canadian launch. Maybe something is… changing? Late last night, an Oishii representative told me they have spent months on the ground, get…

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From now until the end of the summer, this newsletter is intended to be read from the sunny patio of your local coffee shop.

In today’s edition: The New York Times published a Mississauga Dispatch, a development in the controversy around the Humber Yacht Club, and Globe Style editor Odessa Paloma Parker plans to run for mayor.

• …

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Last night I went to the screening for the first of a two-part Dragon’s Den finale at the TIFF Lightbox. After two decades on air, executive producer Molly Middleton dreamt up a spin-off in which five entrepreneurs who’d appeared on the show and went on to build successful businesses—Jay Klein, Joanna Griffiths, Marc Lafleur, Barb Stegemann, Tara Bosch—would return, ready to invest their own capital.

It not only made for excellent television, but an event that brought together a large part of the business community that Milk Bag is focused on covering. The guest dragons were there. Actual dragon Michelle Romanow was there. Moez Kassam, who should be a dragon, was there. I sat with Andrea Grand, the co-founder of the sparkling water brand Barbet, who, in the moments after Eden Hazan and his brother Don secured investment for their frozen pizza company Dreamcrust, whispered “this is so motivating.” And that, is the power of this show.

Beyond inspiring a new generation of entrepreneurs, Dragon’s Den established the first wave of celebrity founders in a pre-social media era: Kevin O’Leary, Arlene Dickinson, and Robert Herjavec are now household names with the star power to make or break companies, and though the guest dragons are already well-known in their own right, the show will likely bring them more into the mainstream.

In today’s edition: The guest dragons on the businesses they’d start today, why everyone is talking about the Block layoffs, a Montreal-based ShopMy for travel is now worth $300 million.

The world has changed a lot since these founders first pitched their ideas in the den, so my question to them was: If you had to pitch a new business today, what would it be?

Jay Klein, The Pur Company

“I’d probably sell something more expensive, that doesn’t expire.”

You need enormous sales numbers to generate positive cash flow for low priced items. If I were to do it again, I’d probably sell something more expensive, where the money piles on faster with the same level of sales. I like to joke that if I sold airplanes, I’d only have to sell one, which would be much easier than selling a lot of gum. Something that doesn’t expire, too. There’s the airplane example, or I think of anything finance-related, like banking and management.

There is an opportunity to create products that those with significant resources demand, and the barriers to entry for those businesses are very high. In CPG, it’s easy for someone to enter a market with the same idea, for a granola bar or water, and access many, many manufacturers. You have to work that much harder. When there aren’t so many manufacturers, and a consumer is less price sensitive, it gives you more stability than when you’re competing with discounts.

In the food business, people chase what everyone else is doing, so I really try to stay away from the herd—at one point, there were hundreds of energy drinks, and all of them were trying to be like RedBull. But leaders lead, and RedBull is still Redbull. I like to ask, how can you be a leader at something? How can you be the best? Other elements I like to deconstruct: Do you have a path to success? Can you scale? Is there a global nature to what you’re doing?

Tara Bosch, Smart Sweets

“It’s actually exactly what I am building right now [at snackish].”

I am always drawn to ideas with a radical value proposition. Something that does not just tweak a category but redefines it. I look for products people already love and grew up enjoying but feel conflicted about as adults. The sweet spot is where you can remove friction and deliver joy. It has to be instantly clear, emotionally resonant, radically differentiated at shelf, and strong enough to build a movement around, not just a product.

Nostalgia is incredibly important to me in that process. The brands that shape us are usually tied to memories. After school snacks. Road trips. Sleepovers. The taste you associate with a certain chapter of your life. When you can tap into that emotional memory and reimagine it in a way that aligns with how people want to live today, that is powerful. You are not just selling a product. You are reconnecting people to a feeling.

That is actually exactly what I am building right now. A new vision that launches across North America in June. It is rooted in the same belief that built my first company. You should not have to choose between taste and ingredients, between fun and feeling good. It is about taking something familiar and beloved and rebuilding it with intention. Craveable, fun, and built for a new generation (hint: if you ever feel a little snackish, this one is for you).

Marc Lafleur, truLOCAL

“I’d go 100% all in on developing niche AI products or services.”

For myself personally, it’d be a business management interface. In this example, I’d target non-technical founders and CEOs doing under $30 million in revenue. In every small company, teams are using five different tools: Slack, Monday, Jira, Meta Business Suite, Google Ads, etc. Getting everyone onto one tool is nearly impossible. Every founder has tried it. Big companies have solved this, but small businesses haven’t.

With AI, you don’t need everyone on the same tools. The AI can pull together everything from raw data and organize it into one interface, regardless of what tool it came from. One place to see everything, track progress, manage projects, and monitor KPIs. No technical knowledge required. The founder or CEO sees what’s happening across the business, without needing to know where any of it is coming from or how it got there.

The main thing to pay attention to for something like this, is to go niche. Going narrow forces you to get the right things right. A general tool gets your customer 80% of the way there. That last 20%, the features that only your specific audience cares about, is what decides whether they use your product or keep using the big platforms. You can’t build that 20% for everyone. But you can build it for one specific customer.

That’s also what reduces your risk. Building for a specific audience means solving real, known pain points. You can talk to your customers, understand what breaks in their workflow, and build for that. You’re not guessing. The broader you go, the more you’re guessing. I think it’s the best time in the world to be a founder. The barriers to entry are gone, and everyone who has ever been interested in entrepreneurship should take this as their sign to do it.

Barb Stegemann, 7 Virtues

“If I were to pitch another business, it would be another beauty brand.”

Beauty is growing. But success does not depend solely on the industry. It’s on the business idea and the founder who will end up driving the business to success. If I were to pitch another business, it would be another beauty brand. I’ve had a lot of fun experimenting with making lipsticks by hand. I’d continue to sustainably source clean ingredients, but would go into skincare and makeup.

It would be exciting to return to making clean, literally edible lipstick. Women end up consuming up to 4 pounds of lipstick in a lifetime, so you want to ensure the ingredients are clean. Similar to my initial pitch, there are lovely oils that can be sourced to support farmers around the world—shea butter from Africa, castor oil from Brazil, and Argan oil from Morocco. What a journey that would be.

Joanna Griffiths, Knix

“I think the opportunity to improve men’s basics is huge.”

One hundred percent it would be MNTD, the men’s underwear brand that we launched about three months ago. Men want good daily essentials that keep them feeling fresh. The opportunity to improve men’s basics (think underwear, t-shirts, socks) is huge and we have the ultimate know-how to make it happen since we’ve built authority in the same industry for women for more than 13 years.

A lot of the items currently on the market are at two ends of a spectrum—plain with minimal quality, or over-indexed innovation that doesn’t really meet that customer where they are. Since launching, the reaction and sales have exceeded what we ever could have hoped for. Our t-shirts and boxer briefs have been best sellers and I’m eager to continue investing in that piece of our business.

• Everyone is talking about what the Block layoffs mean for the white collar workforce. By now you’re probably seen that Jack Dorsey is firing 40% of his employees to restructure the company into smaller, AI-supported teams. Because markets have reacted so well to the news, the immediate fear is that other companies will try this without having the systems and tools to pull it off. And while it’s not the main takeaway, I wonder if more founders will start posting their internal notes (that they know are going to leak online anyway).

• Peter Kafka of Business Insider broke down why Netflix likely walked away from its $83 billion bid to buy Warner Bros. Discovery. He writes: “If your investors don't want the deal, and the people who need to approve the deal [Republicans] don't want the deal, what options do you really have?” That means Larry Ellison’s Paramount could end up owning all of WBD if the company can get past California regulators: Not just the studio and HBO, which Netflix wanted to buy, but its TV networks as well, including CNN.

  • This week, investor Ross Gerber said Paramount could overpay, leaving it to manage losses “forever” while Netflix earns a $2.8 billion break up fee.

• Roselle’s Oishii strawberry cheesecake tarts are your sign that Toronto has fully embraced these premium Japanese berries. An eight-pack sells for $14 and they’re sold out at Eataly and a handful of other grocery stores in the city.

• Seriously considering writing off this ticket to have the 20 best chefs in the city cook for me over the course of one evening. And it’s all for charity, too.

• In the last two months, there have been at least two sponsored retreats for women founders. CIBC, Bennett Jones, and Deloitte were among companies that sent April Hicks, the CEO of Toast, and five other founders to Whistler this month for what looked like just a fun weekend of women hanging out and bonding over their work. A similar event put on by a group of younger women founders was marketed to sponsors around the social reach of those participating, so I wonder if corporate Canada sees supporting these informal and community-centric trips as both a relationship and brand building effort.

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• The Roncesvalles Village BIA is not messing around with their creative budget this year. They’re currently looking for a muralist to help develop a project around the World Cup and a designer to rebrand the Polish Festival.

• A Toyota Rav4 somehow now costs $60,000 so of course most of us are considering buying a Chinese EV. Even with the supposed security risks.

• A Montreal-based company that I would describe as the ShopMy for travel is now worth about $300 million. Stay22 is making between $70 million and $100 million a year by enabling influencers to earn commissions on bookings made by their followers. This will be a nice income boost for those who stay for free at the €1,800-a-night Hôtel Plaza Athénée (since luxury hotels stand to gain the most here), but ultimately it just brings more ads into your feeds.

• What does it mean, to see Charles Khabouth “pivoting” to $20 meals?

• A global pantyhose company will buy Sheertex. Not a great outcome for the investors that put $37.5 million more into the company last year. After years of millions in losses, Sheertex said it would have become profitable this year.

Ever since coming down with an inconvenient cold while on a trip to New York, I’ve been on a mission to find out how the high-functioning people I know avoid getting sick in the midst of winter, when the environment is working against you but slowing down just isn’t an option. One well-known realtor told me his secret to staying …

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Not a coincidence: My deadline for today’s edition happens to align with the start time for the battle for gold in women’s figure skating. The only person I know who is as deeply obsessed with the Olympics as I am is , which is such a fun way to be.

In today’s edition: Aritzia will acquire Fred Segal as part of its U.S. expansi…

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I hope you had a nice long weekend. I spent mine up in Collingwood, where I got about 20 runs in on Sunday and otherwise worked on big picture items for Milk Bag. I always say the antidote to hating winter is learning to love winter sports.

In today’s edition: Specials for martini and fries are everywhere, The WSJ says skiing ca…

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I’m back in Toronto after a few days in New York, where nobody stopped me to ask what makes me confident, what I do to work out, or to see my apartment. My answers would’ve been online validation (from Milk Bag readers) reading emails on the stairmaster, and no.

In today’s edition: Kotn opened hotel and residency in London, the business of …

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Welcome to the test edition of Milk Bag’s Job Watch, a monthly feature (sent outside of the regular newsletter) that connects thousands of smart readers to the roles that are actually worth applying for.

When selecting jobs to include, I considered total compensation (bonuses, equity, and benefits), company brand, whether the work seems genuinely interesting, and if it sets you up for career growth.

Even if you’re not actively looking for work, this edition can help you understand:

1. Which companies are investing in what teams

2. The key trends shaping hiring across categories

3. If you’re underpaid for the job you’re performing

I spent my weekend looking at thousands of jobs to find the best open roles across finance and accounting, sales and growth, brand and communications, and more. If it helps one person, I think it was worth it.

Based on this research, here are some opportunities that seem to be emerging across 11 categories:

• PR agencies need leaders to manage the demand for creator partnerships and new clients in the health and wellness space.

• Creative roles have been hit hard by generative AI, but product work (fast prototyping and UX skills) is in high demand.

• Financial firms are being reshaped by AI and analytics, with some banks now hiring more data scientists than analysts.

• Interesting work requires high technical competency, especially if you’re in marketing, operations, or strategy.

• Product and growth roles seem to offer especially outsized rewards for those who can link their success to revenue.

If you have a role you’d like to submit for consideration (that meets the above criteria), or would like to sponsor next month’s edition so I can make it free for thousands of readers, email sarah@milkbag.ca.

TABLE OF CONTENTS

1. AGENCY & CONSULTING

2. BRAND & COMMUNICATIONS

3. DESIGN & CREATIVE

4. FINANCE & ACCOUNTING

5. MARKETING & SOCIAL MEDIA

6. MEDIA & EDITORIAL

7. OPERATIONS & TALENT

8. PRODUCT & GROWTH

9. SALES & PARTNERSHIPS

10. STRATEGY & ANALYTICS

11. TECHNOLOGY & SOFTWARE

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People are arguing about the Online News Act, again. To get the 9% of Milk Bag’s readership outside Canada up to speed, news content has been banned on all Meta platforms, most devastatingly Facebook and Instagram, for more than two years, but Ottawa appears to be in talks to potentially reverse that.

There are a lot of conversa…

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As the only person wearing jeans at Dineen the other day, I can confirm that dressing up for the office is so back. In fact, Vogue’s most recent TikTok trend tracker ranks #OfficeOutfits as a top search, and Google Trends data from last month shows a similar spike in interest.

Big companies started relaxing dress codes nearly a d…

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Regardless of what your life looked like in 2016, there’s a strong chance you were using skincare from The Ordinary. By the end of that year, the…

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And a happy snow day to those who aren’t dedicated enough to their craft to honour their in-person work commitments. Really sets apart the makers from the fakers. Just kidding, you should have definitely stayed home if you needed to. Just know the rest of us put on our Moon Boots and got on with our day.

Kidding. I’m totally kid…

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I thought we’d be able to slowly ease back into the 2026 news cycle together—but no. In fact I’m already so exhausted by some of the headlines coming out of (specifically) the U.S. that it feels like a good time to redirect our attention to what’s happening at home, in Canada, with Milk Bag’s first edition of 2026.

I’ve missed wr…

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