✈️Thinking About the UAE? Recruiter Oscar Orellana-Hyder Shares What It Really Takes

If you’ve followed me for any length of time, you know I’m a sucker for new frontiers. Whether it’s micro or macro trends, I like to explore what’s next—and who’s building it.

Lately, I’ve noticed an increasingly loud signal: a growing number of Canadians and Americans—myself included—are looking to the UAE for what comes next. Not just because the job market in North America feels uncertain. But because the Middle East, and the UAE specifically, feels like a place where optimism is still allowed to breathe. Where the future isn’t something to fear—it’s something you help shape.

As part of my exploration, I invited Oscar Orellana-Hyder to the podcast. Oscar is a seasoned headhunter who left the City of London a decade ago to build a career—and now his own firm—in Dubai. He has helped hundreds of executives make the leap into the region, and he brings a rare mix of candor and context.

If you’re even thinking about making a move—or just want a deeper understanding of this evolving global hub—our conversation is a must-listen. But in the meantime, here’s a deeper dive into what I took away.

🔑 1. Want to Win in the UAE? Drop the “Western Speed” Mindset

One of the first things Oscar made clear: the UAE is not just a sunnier, tax-free version of London or Toronto. It’s a different operating system.

In the UAE, especially Abu Dhabi, relationships matter more than resumes. Trust is built slowly. Deals take time. Hiring processes can involve 6, 8, even 10 interviews—and that’s normal. Brunches and paddle games may precede boardroom decisions. And no one is in a rush just because you are.

If you’re used to the “one call, one close” approach of North America, this will be a shift. But if you lean into it, you’ll find that the slower pace comes with deeper roots—and often, longer-term loyalty.

💡 Takeaway: Success here isn’t about having the best credentials on paper. It’s about showing up, being present, and building trust—over time. Whether you are looking for a job, raising capital or starting a business.

🌍 2. The UAE Isn’t Just Open for Business—It’s Building the Future

Oscar described a region that is not only hiring—it’s building. Sovereign wealth funds, government-backed entities, and family offices are investing in infrastructure, education, and innovation at a scale that feels almost surreal from a Western vantage point.

Think: NYU, Sorbonne, Harrow—all with campuses in the UAE. Think: sovereign funds requiring portfolio managers to set up shop locally before cutting a check. Think: getting term sheets that say “We’ll invest—but you need to open an office in Abu Dhabi and hire locally.”

In Oscar’s words, it’s no longer about extracting capital from the region. It’s about contributing to it.

💡 Takeaway: If you want to work with UAE-based institutions, come with more than a pitch deck. Come with a plan to invest in the region—personally, professionally, and structurally.

Share

📈 3. Where Are the Jobs? Middle Management Is Hot—But It’s Competitive

Here’s a quick snapshot Oscar shared:

  • C-Suite roles? Often parachuted in. Networks matter more than job boards.

  • Mid-level (8–12 years of experience)? Massive demand, especially in compliance, finance, and risk roles.

  • Junior roles? Often offshored to India, Pakistan, and Bangladesh due to cost and proximity.

  • Industries? Finance remains dominant, but tech, real estate, and strategic consulting are growing fast.

He also emphasized that companies often hire from their own network or through trusted recruiters—meaning your odds are better with local connections and warm intros than with blind applications.

💡 Takeaway: If you're not a local hire, don't expect the process to mirror your last job search. You’ll need persistence, patience, and people on the ground advocating for you.

💰 4. Zero Income Tax? Yes. But Don’t Be Naïve About Costs.

It’s easy to get stars in your eyes when you hear “no income tax.” But as Oscar pointed out, that’s just part of the picture.

  • Schools? All private. Think U.K. boarding school tuition—but yearly.

  • Healthcare? Paid by the employer, but quality and coverage vary widely.

  • Groceries and lifestyle? Easily 2x compared to Canada or the UK, especially if you stick to imported goods.

  • Rent? Comparable to central London or downtown Toronto.

💡 Takeaway: You might make more on paper—but costs are real. Budget realistically, especially if you’re relocating with a family.

Share

✈️ 5. The Geography Is Small, the Energy Is Big—and the Opportunity Is Real

Dubai and Abu Dhabi may be compact, but the global ambition is huge. Oscar mentioned that Abu Dhabi is an 8-hour flight from 80% of the world’s population. That means the UAE is becoming a natural hub for capital, talent, and connectivity between East and West.

It also means—if you’re entrepreneurial, curious, and flexible—you can thrive.

In fact, Oscar said something that really stuck with me:

“The people who succeed here aren’t running away from London. They’re running toward something.”

That really landed. The people who make it here aren’t escapees—they’re builders. They’re optimists. They’re people who want to contribute to something bigger than themselves.

Sound familiar? Maybe that’s why you’re reading this.

💬 Final Thoughts: This Isn’t a Trend. It’s a Tectonic Shift.

The Western job market is tightening. Costs are rising. Institutions are playing defense.

Meanwhile, in the UAE, the mindset is growth. Optimism. Build-mode.

That doesn’t mean the move is easy—or for everyone. But if you’re serious about exploring it, my advice (echoing Oscar’s) is simple:

  • Visit. More than once. Don’t just vacation—network.

  • Get introductions. Don’t rely on cold outreach alone.

  • Be humble. Your CV matters less than your attitude.

  • Be patient. Real relationships take time.

And if you need someone to talk to about it? I’m here. Oscar’s here too. (And yes—he delivers on that offer for a chat.)

Until next time: stay bold, stay curious, and if you’re called to explore—listen.

Peggy Van de Plassche is a value creation strategist and senior advisor with over 20 years of experience in private equity, financial services, healthcare, and technology. She works with investment firms, boards, and C-suite leaders to accelerate portfolio company performance, drive operational transformation, and unlock long-term value. Peggy specializes in the execution of complex value creation plans—spanning capital allocation, digital enablement, transaction advisory, and leadership alignment. Her work consistently bridges strategy and implementation, helping investors and operators maximize EBITDA and enterprise value. A founding board member of Invest in Canada, she also brings deep expertise in public-private partnerships and institutional capital deployment—critical levers for competitive advantage in today’s global landscape. Her clients have included BMO, CI Financial, HOOPP, OMERS, GreenShield Canada, Nicola Wealth, and Power Financial. Learn more at peggyvandeplassche.com.

🧭 How to Invest in Great Companies (and Build a Better Capital Market)

Some events are worth more than a celebration. FrontFundr’s 10th anniversary, held at OneEleven in Toronto early June, was exactly that—a gathering of founders, funders, and believers in a more inclusive innovation economy.

In ten years, FrontFundr has processed close to $300M in investments from nearly 20,000 investors into Canadian startups. That number should stop you in your tracks. It’s not just a milestone—it’s a transformation.

Share

I was introduced to Peter-Paul Van Hoeken and FrontFundr nearly a decade ago. I was already familiar with the model, having invested in and through WeFunder in the U.S. I became an investor in FrontFundr itself, joined the board, and stayed on for several years. What struck me from the start was that this platform wasn’t just about democratizing access—it was about rethinking how early-stage companies raise capital.

💡 Crowdfunding as a Strategic Capital Tool

I’ve long believed in equity crowdfunding. It’s not right for every company or every moment—but when thoughtfully used, it can be more forgiving than institutional capital, especially for B2C businesses. The raise doubles as a marketing campaign, and the pressure for hyper-growth exits is often lower than with VCs.

It also comes with no risk of being strong-armed out of your company—a real concern in traditional VC scenarios.

I had a great conversation with Brice Scheschuk on this very topic: the pitfalls of raising institutional capital too early. VC has a time and place, but founders should understand the trade-offs. The pressure for speed, the power dynamics, and the dilution risks can be intense. Crowdfunding offers an alternative route—aligned, founder-first, and community-driven.

Share

That alignment is something I also see in another capital model I believe in: non-dilutive revenue-based financing. I’ll be hosting Melissa Widner, CEO of Lighter Capital, on the podcast next month. Lighter provides debt capital to tech companies—another strategic tool that can be used alongside equity crowdfunding.

The beauty of both Lighter and FrontFundr? They’re young, agile platforms that have had to raise capital themselves. They understand their clients, because they are their clients. They’re not just service providers—they’re co-builders.

🧠 Angel Investing, Founder Character & Cap Table Wisdom

At the event, Peter-Paul interviewed Joe Canavan, Angel Investor of the Year. Joe has that rare combo of investor rigor and entrepreneurial empathy. He shared his approach to identifying what makes a company investable today:

  • Board of advisors: experienced, strategic, and founder-supportive

  • Cap table quality: filled with smart, value-adding investors

  • Market size: of course—but not before founder character

  • Character: the top filter. Always.

Joe’s approach resonated deeply. He meets founders’ families. He looks for alignment in values. He knows it’s a long journey—and that you need to like the people you’ll be stuck with. And he’s seen enough to know the real risk isn’t just the business plan—it’s whether the founder will do the right thing when things get hard.

🔍 What I Look For in Founders

Like Joe, I’ve developed my own mental checklist. A few quick patterns I’ve seen over the years:

  • Tech-heavy founding teams often struggle to commercialize. I look for a balance between business acumen and technical depth.

  • Cultural background influences go-to-market strategy.
    Americans and Israelis tend to lead with sales. French and Canadians often lead with product. That matters.

  • If a company has raised a lot of VC? I assume there’s waste.

For early-stage investments (crowdfunding or otherwise), I focus on founder mindset, capital efficiency, and the ability to evolve. Pattern recognition is great—but people recognition is better.

One point that I wish more investors considered: early investors often get diluted later by institutional capital. It takes an ethical CEO to protect the first checks—the believers who backed them when no one else would. And that’s why values matter. A lot.

🎯 Final Thought: Capital That Compounds (and Connects)

FrontFundr’s 10-year milestone is a reminder that capital can be inclusive, strategic, and aligned with founder success. You just need the right structure, the right support—and the right people.

Platforms like FrontFundr and Lighter Capital are building something better. Something more human. Something that doesn’t just generate returns—but builds companies we actually want in the world.

Congrats to Peter-Paul and the FrontFundr team. And to all the founders out there: raise wisely, build boldly, and never underestimate the value of character.

Peggy Van de Plassche is a seasoned advisor with over 20 years of experience in financial services, healthcare, and technology. She specializes in guiding boards and C-suite executives through transformational change, leveraging technology and capital allocation to drive growth and innovation. A founding board member of Invest in Canada, Peggy also brings unique expertise in navigating complex issues and fostering public-private partnerships—key elements in shaping the Future of Business. Her skill set includes strategic leadership, capital allocation, transaction advisory, technology integration, and governance. Notable clients include BMO, CI Financial, HOOPP, OMERS, GreenShield Canada, Nicola Wealth, and Power Financial. For more information, visit peggyvandeplassche.com.

💡How to turn external tech teams into a strategic asset

If you are listening to the podcast you will notice that today’s guest was especially easy to introduce for me—finally, a French name that I could pronounce ;) I had the pleasure of speaking with Sean Languedoc, a serial entrepreneur and the founder & CEO of Outforce AI. His mission? To make tech outsourcing not just efficient, but actually strategic.

We’ve all been there—burned by agencies that send in their B team, delayed by months of inefficiencies, and exhausted by the mismatch between what’s promised and what’s delivered. Sean’s view? Outsourcing is broken. But fixable.

🧠 Matching Tech Talent with Precision

Outforce AI isn’t an outsourcing agency. It’s a data-driven matchmaker for engineering and data science services—curating top-performing agencies from a database of 79,000+ firms, based on domain expertise, tech stack depth, delivery history, and even cultural alignment.

Think of it like executive search, but for teams of engineers. Instead of “Do you do healthtech?” and getting a canned “Yes,” Outforce uses granular data to match companies with providers who’ve actually done the job—successfully, repeatedly, and with the right bench strength.

“Little data to make a big decision is a bad way of doing things.”
– Sean Languedoc

Outforce reduces the failure rate of outsourcing projects (often cited as 50–60%) to a stunning 98% success rate. The secret? Start with the team and timing—not just a brand name (or the price!)

⏱️ In PE, Speed Is the Alpha

Sean’s client base today includes mid-sized U.S. private equity firms, helping their portfolio companies build or refactor tech products fast. In private equity, speed to execution = value creation.

And nowhere is that more important than in the first 100 days post-acquisition. During that window, Sean says firms need to swarm:

  • Audit the product and the codebase

  • Evaluate decision-making logic (a nod to Conway’s Law)

  • Determine who on the tech team is staying—and who needs to go

  • Decide whether to scale the existing tech or rebuild it

In that contect, he offered two smart approaches:

  1. Bring in a full team to re-architect while legacy engineers maintain the current product.

  2. Augment the team internally to free up in-house talent for a rebuild.

Either way, the goal is the same: don’t lose momentum, speed is of the essence.

🤝 Outsourcing Can Be Strategic

Sean’s most provocative idea? That owning your tech staff isn't always necessary, especially in the early stages. Instead, the right outsourced team can:

  • Accelerate product-market fit

  • Free up equity allocation

  • Enable faster scaling without the 9-month hiring drag

Outsource the right way, and you gain speed, quality, and flexibility. That’s the holy trinity.

His warning: price-first outsourcing leads to rewrites. Think “Ocean’s Eleven” teams instead—small expert agencies with pattern recognition, cultural fluency, and domain expertise.

Share

🛠️ Technical Debt, Culture & Communication

In PE, buying older assets often means confronting legacy tech. But solving for technical debt isn’t just a DevOps issue—it’s a people and culture issue too.

Outforce AI considers:

  • Communication style (are they problem-solvers or order-takers?)

  • Cultural mindset (do they question? or just say “yes”?)

  • Team dynamics (can they handle feedback? work iteratively?)

They even worked with a neuroscientist trained in cultural adoption to understand how cross-cultural communication impacts productivity. Think agile American start-ups vs. deferential Southeast Asian engineering cultures—mismatched expectations can kill speed and results.

💡 Final Takeaway: Treat Outsourcing Like Interior Design

One of my favorite moments from the conversation? I compared using Outforce AI to hiring my interior designer. He got me discounts, knew where to go, and saved me a ton of time, money and stress. The value more than paid for itself.

The same is true here. Sean isn’t just matchmaking. He’s enabling transformation.

And in a world where funding cycles are tight, leadership churn is high, and talent is global, that's exactly the edge portfolio companies need.

📌 For more, check out Outforce AI and Sean’s upcoming video series on outsourcing best practices. And if you're a VC, PE investor, or a tech CEO: this one’s worth bookmarking.

Peggy Van de Plassche is a seasoned advisor with over 20 years of experience in financial services, healthcare, and technology. She specializes in guiding boards and C-suite executives through transformational change, leveraging technology and capital allocation to drive growth and innovation. A founding board member of Invest in Canada, Peggy also brings unique expertise in navigating complex issues and fostering public-private partnerships—key elements in shaping the Future of Business. Her skill set includes strategic leadership, capital allocation, transaction advisory, technology integration, and governance. Notable clients include BMO, CI Financial, HOOPP, OMERS, GreenShield Canada, Nicola Wealth, and Power Financial. For more information, visit peggyvandeplassche.com.

✈️ Staying Global in a Deglobalizing World

Last week, I attended Burgundy’s annual forum in Toronto—a quiet powerhouse gathering for serious investors. This year’s theme, “Staying Global in a Deglobalizing World,” felt particularly timely. Two keynotes stood out and made me rethink what diversification actually means in a world where capital, narratives, and attention are all getting a little more domestic.

My takeaway? In a fragmented world, the best investment approach is still the simplest one: focus on compounding. Good businesses, bought at reasonable valuations, held through the cycles. Businesses that create value, adapt, and keep going—especially when markets get choppy. And they will get choppy. As one speaker put it: we’re all bound to pass through rough seas. That’s a feature of long-term investing, not a bug.

🔍 Rethinking Diversification – Anne Mette de Place Filippini

The second keynote came from Anne Mette de Place Filippini, CIO at Burgundy, and she did not disappoint. With a calm but pointed delivery, she challenged several lazy assumptions in investing today.

One of her early comments—half joke, half truth—set the tone:
“Why not invest in more of the winners and less of the losers?”
A 20/20 insight, of course, but a reminder that performance attribution often comes with hindsight and that conviction needs to be earned in real time, not retroactively justified.

She revisited diversification—not as a spreadsheet exercise, but as a principle of humility. To quote Buffett, “Diversification is protection against ignorance,” but Anne Mette was quick to point out: not at the cost of understanding. Diversification only works if you understand what you own, why you own it, and how each piece contributes to the whole.

Her skepticism of endowment-style investing was striking. Too much complexity, too many fees, and not enough transparency. Institutions chasing premium returns with premium structures, but with no actual premium showing up in the results. It’s a good reminder: complexity doesn’t equal quality, and diversification without clarity can actually destroy value.

She pointed to opportunities outside the U.S.—in smaller and mid-sized companies, and in regions that don’t dominate the headlines. Today, U.S. stock markets are lagging, even as the U.S. economy is supposedly stronger than Europe’s. So much for American exceptionalism. There’s a large hunting ground in the rest of the world, filled with underappreciated opportunities just waiting to be discovered.

She emphasized that investing isn’t about chasing market trends, but about recognizing that price is not the same as value. That achieving balance doesn’t mean swinging between extremes, but rather holding firm to discipline through volatility. From volatility comes the ability to compound—and that’s where the real value lies.

Share

🌍 Europe: Relic or Rising Opportunity? – Kenneth Broekaert

The third keynote, delivered by Kenneth Broekaert, SVP and Portfolio Manager, brought a slightly different flavor to the day: more narrative, more history, and even a touch of dry humor. He posed a provocative question:
“Europe: relic or rising opportunity?”

Since Liberation Day, he said, investors have asked themselves whether they were too concentrated in the U.S. That question is still relevant—and increasingly worth revisiting.

Kenneth’s answer was unequivocal: Europe is not just relevant—it’s robust. It houses some of the best companies in the world, particularly in healthcare, consumer goods, and industrials. Many of these businesses are leaders in their categories and geographies. They benefit from real scale—like Heineken 0% leveraging Verstappen in global advertising—and they’ve built resilient models with high recurring revenues and limited exposure to global supply chain disruptions.

His preference? Companies that produce where they sell—a structural edge in an era of tariffs and fractured trade routes.

He made the case that European equities offer stability, lower valuations, and higher dividends—a rare combination in today’s market. Healthcare companies, in particular, provide essential products in every economic environment. Industrial firms in Europe are often treated as boring—but boring with recurring revenue can be a beautiful thing when you're looking to compound earnings over time.

What struck me most was Kenneth’s quiet confidence in the compounding power of European returns. Not as a contrarian bet, but as a smart, grounded strategy for investors willing to go beyond headlines and lean into fundamentals.

🎯 Final Thought

In a world turning inward, looking outward may be the edge.
Staying global doesn't mean owning “the market.” It means owning what compounds.
And more often than not, that means looking beyond what’s obvious.

Peggy Van de Plassche is a seasoned advisor with over 20 years of experience in financial services, healthcare, and technology. She specializes in guiding boards and C-suite executives through transformational change, leveraging technology and capital allocation to drive growth and innovation. A founding board member of Invest in Canada, Peggy also brings unique expertise in navigating complex issues and fostering public-private partnerships—key elements in shaping the Future of Business. Her skill set includes value creation, strategic leadership, capital allocation, transaction advisory, technology integration, and governance. Notable clients include BMO, CI Financial, HOOPP, OMERS, GreenShield Canada, Nicola Wealth, and Power Financial. For more information, visit peggyvandeplassche.com.

🏡 The Leak, the Ladder, and the Illusion of Trust

During the two days of non-stop rain in Toronto at the end of May, my better half and I were awakened in the middle of the night by water dripping from the ceiling—right in the middle of our bedroom.

After installing the necessary bucket and towels, we reached out to our roofer and general contractor, who had worked on our roof (and redone it) not once but twice in the past five years. I don’t think anyone ever expects a leak, but with a new roof and new windows, this was definitely not on our radar.

Obviously, when morning came—after pretty much a sleepless night—I called our insurance company to get organized. In the meantime, our roofer called to let us know he would be there a few hours later. I was unfazed. Not my first leak, not their first leak—a pain in the butt, but in the grand scheme of things, a non-problem. Of course, I had to cancel my meetings to accommodate the visits and calls, but still—no biggie.

As expected, the roofer came toward the end of the morning to check things out. First thing he asked for was a ladder to get on the roof. Well, I don’t know about you, but I don’t have a ladder. I’m not in the habit of climbing onto my roof—I’m sure it’s a lovely vantage point, but that’s what rooftop patios are for. And with that, the shitshow began: where can we get a ladder? And not just any ladder—a ladder of a specific height.

Okay, so now I’m calling a friend on my street who—Murphy’s Law—happens to be in NYC on business. Thankfully, she answers and thinks she has the right type of ladder. Then I have to reach out to her husband, which I promptly do after she shares his number. Thankfully, he answers—yes, he’s home, yes, he has the ladder.

So here I am, climbing into the roofer’s truck—clearly not expecting passengers—while it’s still pouring rain. We make it to the end of my street and, after some back and forth, leave with the lighter ladder with fewer features (it doesn’t wash the dishes). Back to my house. Naturally, some Uber is parked across the edge of my driveway, which hadn't been an issue earlier when the roofer just parked in front of my neighbor’s garage. Thankfully, the driver saw that I looked partially disheveled and clearly on the verge of a nervous breakdown and promptly vacated the spot. This didn’t stop the roofer from blocking my other neighbor’s driveway—because why not?

Finally, we make it to the top level. Still pouring rain. He gets on the roof. I’m lighting a candle, expecting to see him fall through one of my skylights any second.

Eventually, he comes back. Diagnosis? Uncertain. Could be a pipe. Of course, it started leaking during torrential rain—it must be a pipe! Oh wait, there’s no pipe in that room. Could be the neighbor’s skylight. He shows me pictures of how badly the neighbor’s skylight was installed. But based on its location—even if there is a problem—I really don’t see how we’d be affected. Not the top candidate. Could be one of our fans—maybe getting warmer. But based on the photo, there’s no water accumulation around the fans, and the water seems to accumulate in a spot above… hmm. Seems like a clue that the issue is actually right there. Then: could be our fireplace exhaust. And then—ta-da—a picture of the exhaust, not only rusty but corroded, with a massive hole in it.

I’ll spare you the many back-and-forths related to the leak, but—as always—every experience is an opportunity for reflection.

First: who on freaking earth shows up to inspect a roof without a suitable ladder?

Second: the roofer and his team had been on this roof many times over the past five years and never thought to mention that the fireplace exhaust was damaged? That didn’t seem like valuable information to share?

Share

Third: I assume roof leaks are pretty standard for a roofer. So how did this become a game of "spot the 7 differences"? I’d think there are obvious ways to test where a leak is coming from. Put some dye in the high-suspicion areas and see what color shows up in the bedroom, for example. I haven’t ChatGPT’d it, but I’m pretty sure there’s a structured decision tree to track a leak—probably 10 ways to do it efficiently. Which brings me to my fourth point…

Every possible reason—even the most random—was thrown out except the most obvious one: the brand new, still-under-warranty roof is leaking.

⁉️So What Do We Learn?

That fiduciary duty should be extended to any relationship based on asymmetric information and expertise.

What is fiduciary duty, exactly? TY Google for the following definition:

A fiduciary duty is a legal and ethical obligation of a person (the fiduciary) to act in the best interest of another person or entity (the beneficiary). It involves a relationship of trust and confidence, where the fiduciary is entrusted with powers and responsibilities for the benefit of the beneficiary. Fiduciary duties are often implied in certain relationships, such as between a lawyer and client, a director and a corporation, or an agent and a principal. The most common fiduciary relationships involve legal or financial professionals who agree to act on behalf of their clients.”

“Generally, a roofer does not have a fiduciary duty to their client. Fiduciary duties are a high standard of care, requiring a party to act in the best interests of another.”

So expecting a party to act in the best interest of another is not a basic requirement in most commercial relationships—excluding law and finance (more or less). Ironically, I’m better equipped to pressure-test my lawyer or financial advisor than I am my roofer or car mechanic.

Why the double standard? I doubt the average person knows more about construction or mechanics than they do about finance or law. Shouldn’t we assume we’re all vulnerable when it comes to specialist knowledge?

In the very straightforward context of this leak, fiduciary duty would have meant: 1) the roofer shows up with a ladder, 2) he tells us years ago that the exhaust is damaged, and 3) he takes responsibility that the brand-new roof he installed might be leaking. But he’s not obligated to do any of that. His only obligation was to install the roof—properly or not seems to be up to his discretion. Maybe offering him a coffee helps? Not even sure anymore.

In an ideal world, we wouldn’t need fiduciary protections. We’d all be ethical, and all would be well. But we don’t live in that world. In this one, integrity is seen as boring, nitpicky, and business-unfriendly.

Which is why trust matters even more. And micro-social recommendations. Can you trust a Kardashian to point you to the best product for you? Probably not. But your friend? Probably yes. That’s why the rise of micro-social networks, niche communities, and micro-influencers is one of the most significant trends shaping the digital and social landscape today.

Share

Since we can only hope that the other side of a commercial relationship will act in our best interest—at a time when everything seems to be monetized and monetizable—having trustworthy people around us is key. Of course, that brings its own challenge: loyalty, nepotism, incompetence—“Yes, he sucks, but I trust him.” But that’s a topic for another time.

So what did we learn?

In any relationship, keep an eye on:

  • Who has a conflict of interest?

  • Who has integrity?

  • And never underestimate the power of a second, unbiased opinion. 😉

Peggy Van de Plassche is a seasoned advisor with over 20 years of experience in financial services, healthcare, and technology. She specializes in guiding boards and C-suite executives through transformational change, leveraging technology and capital allocation to drive growth and innovation. A founding board member of Invest in Canada, Peggy also brings unique expertise in navigating complex issues and fostering public-private partnerships—key elements in shaping the Future of Business. Her skill set includes strategic leadership, capital allocation, transaction advisory, technology integration, and governance. Notable clients include BMO, CI Financial, HOOPP, OMERS, GreenShield Canada, Nicola Wealth, and Power Financial. For more information, visit peggyvandeplassche.com.

🏒What the Maple Leafs’ Playoff Defeat Can Tell Us About the Corporate World

I don’t follow sports. But living in Toronto, even I couldn’t escape the Maple Leafs playoff drama. The story unfolded for me in fragments—each conversation offering a curious window into not just hockey, but power, politics, and performance.

First, a friend cheerfully told me the Leafs were up 2–0. But she quickly added, “Don’t get too excited—they haven’t won in decades.” Fifty-seven years, to be exact.

Then came another update: 2–2. This friend made an unusually astute comment: “They get paid per game played. Of course they all want seven games.”
Indeed, players receive compensation for each playoff appearance. And beyond player compensation—sponsors, TV rights, venues—everyone makes more money when there are more games. It was a bold comment from my friend. Every time I’ve dared to hint at conflict of interest (or even light corruption) in sports, I’ve usually been met with indignation.
Not in my sport! Right.

At 3–3, someone else updated me again—this time to complain about players choking under pressure. Some rise. Others collapse. That’s the playoffs.

And finally: 1–6. The Leafs lost. Fans hurled their jerseys onto the ice in protest.
I shared this with my husband—not a Leafs fan, but a former player—and he got visibly annoyed.
“Do you know how many couch critics I’ve heard scream strategy who can’t even skate five feet?”
Fair. He empathized with the players.

Until I asked him:
“How many times could you choke and fail at your job before getting fired?”
That made him pause.

Because here’s the thing.
If a mid-tier hockey player chokes in a high-stakes game, he might not get re-signed.
But if a top-league player fails to perform? He’ll likely be back next year. And the year after that. He’s already too big to cut loose.

That’s what fascinates me—not the sport itself, but the double standard it reveals.
The “too big to fail” mentality—but applied to individuals.

Share

Same in the corporate world.
If a CEO tanks a strategy, they don’t get fired—they eventually (read: after years) “resign to spend more time with their family.”
But an executive two levels down? Miss your numbers?
Bye-bye. Thanks for playing.

Why is that?

Because once you're at the top, failure becomes too embarrassing—and too expensive—to address.
Too many people vouched for you. Too many reputations are invested in your success.
The board doubles down. The coach “stands behind his players.”
Narratives of resilience are spun.
We all nod, pretending this major screw-up was actually…a great learning opportunity.

“We’ll be stronger because of it.”
“This was necessary for our evolution.”

We’ve heard the script. Watch how quickly everyone aligns.

Recently, I was chatting with a Managing Director at a PE firm.
To get the job, he went through 13 interviews and a full case study.
How many interviews do you think his CEO had to go through? I’d bet not 13.
So why is someone four levels below getting more scrutiny?

This isn’t a rant about how high earners “shouldn’t be allowed to be human.” That’s not the point.
People are people—at the top or bottom of the food chain.
But why is compassion and leniency extended more generously upward than downward?
Shouldn’t it be the other way around?

Why do we normalize this?

We’ve seen similar dynamics in other sports.
In tennis, for instance, there’s been a lot of noise around harsh sanctions for low-ranked players—while top stars, like World No. 1 Jannik Sinner, receive far more lenient treatment for similar infractions.
The higher you go, the more grace you seem to be granted.
Why?

So next time you’re hiring an intern, ask yourself:
Who faced more scrutiny—your intern, or you?
And what does that say about the system?

Food for thought.
Peggy

Peggy Van de Plassche is a seasoned advisor with over 20 years of experience in financial services, healthcare, and technology. She specializes in guiding boards and C-suite executives through transformational change, leveraging technology and capital allocation to drive growth and innovation. A founding board member of Invest in Canada, Peggy also brings unique expertise in navigating complex issues and fostering public-private partnerships—key elements in shaping the Future of Business. Her skill set includes strategic leadership, capital allocation, transaction advisory, technology integration, and governance. Notable clients include BMO, CI Financial, HOOPP, OMERS, GreenShield Canada, Nicola Wealth, and Power Financial. For more information, visit peggyvandeplassche.com.

💸How to Unlock Growth, Profitability, and Resilience Without a Single Acquisition

In finance, we’re wired to look outward—chasing the next deal, the next merger, the next growth story. But what if the biggest opportunity isn’t “out there”? What if it’s sitting quietly inside your business—or your client’s—waiting to be activated?

In a recent talk with financial services professionals, I challenged that M&A reflex—and offered a smarter, more strategic approach: adopt a private equity (PE) mindset to drive real, sustainable value from within.

This isn’t about financial engineering. This is about operational discipline, strategic clarity, and cultural alignment—the levers top-tier PE firms pull every day to create enterprise value. The best part? You can use these tools without a deal, a board shakeup, or a capital injection.

Let’s dig in.

💡 Why Internal Value Creation Beats M&A (Most of the Time)

70–90% of M&A deals fail to create value. Many destroy it.

So why are we still acting like growth is something you buy?

External growth is expensive, risky, and hard to control. Internal value creation? It’s faster, more capital-efficient, and often overlooked.

Whether you're running a company or advising one, now is the time to recession-proof by optimizing what you already own. The smartest businesses today are shifting from “buy” to “build.”

It’s time to shift focus—from growth at all costs to value on purpose.

Subscribed

🔍 The Value Creation Playbook: A Strategic Framework in 3 Pillars

Forget the old-school play of slashing costs and piling on debt. This framework is about increasing the intrinsic value of your business—just like top-tier PE firms do with their portfolio companies.

1. Strategic Clarity

The biggest unlock for value is focus.
Know your core. Double down on what works. Exit the distractions.

➡ Identify what truly drives value in your industry—recurring revenue? IP? Customer retention?
➡ Get crystal clear on product profitability, customer segmentation, and complexity costs.
➡ Align your resources accordingly.

Takeaway: Value starts with knowing what truly drives it. Align capital and effort there.

🧠 Pro tip: Strategy is only powerful when it's specific. A clear 80/20 view will do more than any rebrand or new hire.

2. Operational Excellence

This is not about slashing costs. It’s about doing more with what you already have.

➡ Eliminate waste (process bloat, excess inventory, underutilized systems)
➡ Invest in automation, digitization, and lean operations
➡ Leverage AI where it actually matters (not just for PR)

Takeaway: You can’t cut your way to greatness, but you can fund growth by plugging the leaks.

🧠 Pro tip: Value creation doesn’t need to be revolutionary. It needs to be deliberate.

3. Cultural Alignment

Culture is not a “soft” topic. It’s a hard driver of execution.

➡ Are your people clear on priorities?
➡ Are they rewarded for outcomes?
➡ Are they continuously improving?

If the answer is no, no amount of strategy will save you. You don’t just need the right roadmap. You need the right drivers.

Takeaway: Strategy sets the direction. Culture determines whether you get there—or stall out halfway.

🧠 Pro tip: Embed accountability at every level. Align incentives with value creation, not just activity. If no one owns it, it doesn’t get done.

🧰 Think Like PE—Without Selling to PE

Private equity isn’t just about capital. It’s about discipline.

Imagine bringing PE tools—100-day plans, KPI dashboards, pricing strategy—to your business or client portfolio. No deal required. Just the mindset and the method.

You don’t need to sell your company or take an investor to operate like a world-class firm.

This is what top PE firms bring to the table post-deal. But why wait? Use the playbook now—without giving up equity.

📈 In This Market, Internal Value Creation Isn’t a Nice-to-Have. It’s Survival.

With macro headwinds mounting—higher rates, inflation, geopolitical instability—the margin for error is thin. Businesses need to move now to become more resilient, more profitable, and more focused.

So I’ll leave you with one question:

💬 What value are you leaving on the table today?
Because that’s where your next 20% upside lies.

If you’re looking for an advisor, speaker, or board member who can bring a practical value creation lens to your company or clients—let’s talk. You can connect with me directly or reach out through my speaker agent, Shari Storm.

Let’s build value on purpose.

Share

Peggy Van de Plassche is a seasoned advisor with over 20 years of experience in financial services, healthcare, and technology. She specializes in guiding boards and C-suite executives through transformational change, leveraging technology and capital allocation to drive growth and innovation. A founding board member of Invest in Canada, Peggy also brings unique expertise in navigating complex issues and fostering public-private partnerships—key elements in shaping the Future of Business. Her skill set includes strategic leadership, capital allocation, transaction advisory, technology integration, and governance. Notable clients include BMO, CI Financial, HOOPP, OMERS, GreenShield Canada, Nicola Wealth, and Power Financial. For more information, visit peggyvandeplassche.com.

🧠 Founders, Play Your Own Game

Hi. Hello. Hello. 👋

Today’s guest is a dear friend, a repeat podcast guest, and someone I respect enormously for his deep thinking and straight talk: Brice Scheschuk.

If you know Brice, you already know he’s built, scaled, exited, and reinvested with wisdom. If you don’t, here’s the gist: he’s an operator turned investor with a rare lens—130 direct startup investments, 50+ VC fund LP positions, and most importantly, no one to please but the truth.

We ran into each other recently over drinks, and Brice shared his latest keynote: "Founders, Play Your Own Game."
It’s part tough love, part strategic blueprint. And it resonated with me on every level. You can find the link to his presentation here.

Here’s what we explored—and why every founder, funder, and advisor in the innovation ecosystem should read this.

🚨 The Most Consequential—and Irreversible—Decision a Founder Makes

Brice calls it out plainly: raising capital is not just a milestone—it’s a turning point.

Once you take money, especially VC money, you commit to a set of expectations that can change your culture, control, governance, and trajectory. The math changes. The growth expectations accelerate. The room for error shrinks.

My take: “It’s like a favor with the mafia. Once you’ve shaken that hand, you’re in the game.” ;-)

His core argument? Most founders don’t understand the rules of the game they’re entering. And worse, the ecosystem’s conventional wisdom makes it sound like VC is the only game in town.

📉 The VC Narrative: High Valuation, High Velocity… High Risk

Brice breaks down the past decade of venture into three chapters:

  • 2016–2019: Risk-on boom and valuation creep

  • 2020–2021: Pandemic stimulus, zero rates, digital hype—and a bubble that rivals Dotcom 1.0

  • 2022–today: Reality check, capital contraction, and now… the AI frenzy

Most companies that raised big during the hype years are now struggling, gone, or playing catch-up. The capital created a treadmill they weren’t ready to run.

“99.9% of the oxygen in the ecosystem is about why to raise VC. But 99.9% of companies shouldn’t raise it.”

Oof. Let that sink in.

Share

🧭 Raising Capital (or Not) Is a Strategic Identity Question

So how do you know if raising capital is right for you?

Brice’s checklist is as nuanced as it is practical:

✅ Do you deeply understand your market, product, customer, and go-to-market math?
✅ Are you building something truly venture-scale—or just using the wrong financing for your actual growth model?
✅ Are you ready to lose some control to gain some capital?
✅ And most importantly: Who are you building for—and what kind of entrepreneur do you want to be?

He uses Shopify’s Tobi Lütke as a model: six years of patient exploration, only $1M raised, and a culture defined before VC ever entered the picture.

Contrast that with the standard: Demo Day, deck, $3M on $30M valuation, little customer insight, and a power-law investor expecting a billion-dollar exit. That’s a mismatch—and a slow-motion car crash.

🧠 Invert, Always Invert: The Power of Counter-Narratives

Brice is a fan of Charlie Munger, and his advice follows Munger’s “inversion” principle: figure out where failure lives and avoid it.

That means:

  • Model your business as if you had to bootstrap it.

  • Build in plateaus. Assume the hype fades.

  • Explore non-dilutive capital: consulting, grants, debt (when rational).

  • Cut the clutter. Funded startups often spend because they have to, not because it makes sense.

In short: raise less, learn more, grow cleaner.

🧘‍♂️ Mindset Wins: Entrepreneurial Resilience Isn’t Optional

Brice also teaches a workshop on entrepreneurial resilience, rooted in 100+ expert interviews and years of observing founders under pressure. He breaks resilience down into:

  • Personal: self-awareness, stress recovery, habits

  • Team: decision hygiene, communication, cognitive load

  • Organizational: governance, culture, structure that supports—not drains

“The 81st hour of the week might be better spent outside your business. It could save your next 80.”

This isn’t fluff. It’s a corrective to hustle culture, which has done real psychological and financial damage to founders.

Share

🔁 Conventional Wisdom? Strike It Out.

Brice’s final mic drop?

He wears a T-shirt that says:
“Conventional Wisdom” (with a red strike-through).

Everything you’ve been told—do the accelerator, avoid services revenue, raise fast and big—deserves a second look. The better path? One that fits your business, your goals, and your life.

Subscribed

🧩 Takeaways for Founders (and Funders)

  1. VC is a tool, not a destiny. Use it if and when it fits. Not before.

  2. Founders must own their financing strategy. Don’t abdicate to what’s fashionable.

  3. Building lean is not a bug—it’s a Canadian superpower.

  4. Control is underrated. Dilution is forever.

  5. The right capital, at the right time, for the right reasons. That’s the game.

And that’s the message we need to amplify across the Canadian tech ecosystem.

Share

Thanks again to Brice Scheschuk for bringing such clarity, candor, and courage to this conversation.

🎤 We'll definitely have him back in the fall—for a deep dive into resilience and the founder psyche.

Until then: Play your own game.

Peggy Van de Plassche is a seasoned advisor with over 20 years of experience in financial services, healthcare, and technology. She specializes in guiding boards and C-suite executives through transformational change, leveraging technology and capital allocation to drive growth and innovation. A founding board member of Invest in Canada, Peggy also brings unique expertise in navigating complex issues and fostering public-private partnerships—key elements in shaping the Future of Business. Her skill set includes strategic leadership, capital allocation, transaction advisory, technology integration, and governance. Notable clients include BMO, CI Financial, HOOPP, OMERS, GreenShield Canada, Nicola Wealth, and Power Financial. For more information, visit peggyvandeplassche.com.