Today’s Operators Newsletter …

🏆 Cody Plofker on 5 leadership lessons straight from Shopify’s president

😬 Sean Frank on when + how to fire — the hardest decision in leadership

🎁 Connor Rolain on the ultimate Black Friday ad strategy & 2025 bets

📊 Connor MacDonald on pacing uneven holiday revenue (Sheet + Loom)

Along with this week’s top-five trending stories, links, and executive summaries.

Connor Rolain

Head of Growth, HexClad

The Ultimate Black Friday & Cyber Monday Ad Strategy + 2025 Big Bets

In case you missed it … Cody, Connor Mac, and I did a live session at Motion’s 2024 Creative Strategy Summit.

Our replay just hit YouTube.

I kicked things off by giving a detailed look into HexClad’s performance last year. Especially which ad formats had the best one-day ROAS. I also dug into how we’re using what worked and what didn’t work in 2023 for 2024.

Cody talked about filling your holiday funnel — month-by-month, campaign-by-campaign, channel-by-channel — and why you need to trade efficiency for reaching new people in order to capitalize on key offer moments.

Ultimate Guide to Black Friday, Cyber Monday Ad Strategy & 2025 Big Bets

Connor Mac shared insights into Ridge’s influencer strategy — an acquisition channel they’ll spend seven figures on during the holidays. Plus, he explained how to properly time your spend to get the biggest lift.

Finally, each of us ended with our 2025 big bets.

Check out the session!

Reply to this email with any questions you’ve still got about the holidays — or let us know your own big bets.

Watch the Full Video

Cody Plofker

CMO, Jones Road Beauty

Last week, Harley Finkelstein (president of Shopify) came on the podcast. It was a monumental moment for us as hosts.

Much of the conversation centered on leadership.

Since then, I’ve been trying to hang onto and apply as many of Harley’s invaluable insights as possible. So, here are …

5 Leadership Lessons from Shopify’s President

Become Your Customer
Get into Details “Mode”
Set & Raise Expectations
Establish Trust, Then Say No
Never Be Perfect or Done

1. Become Your Customer

No product can succeed without prioritizing its customers and their experiences. Being customer-focused or customer-obsessed is often how that’s framed.

Harley took it a step further with “dogfooding.”

“Forget empathy. Empathy is when you put yourself in the shoes of someone else. That is not what I’m talking about.

“What I’m talking about is actually using the product so you yourself are a customer. When you do that, you tend to have much higher fidelity, feedback, and advice.”

Becoming your customer is one of the reasons Harley co-founded Firebelly Tea in 2020, which (in turn) led to one of the reasons Shopify developed native subscriptions.

Depending on your product, dogfooding can be tricky. I’ll never be a real consumer of Jones Road Beauty the way both Connors are of Ridge and HexClad.

Thankfully, our founder is exactly that.

On my end, it’s pushed me into our marketing with fresh eyes to experience the entire funnel as an outsider. Ads, landers, emails, texts, purchase, and post-purchase.

2. Get into Details ‘Mode’

With so much talk about founder mode since Paul Graham’s essay, the term inevitably came up.

Against traditional management — i.e., hire the right people and get out of their way — founder mode stays in the details.

Recalling weekends spent reviewing customer feedback on social, Harley noted:

“If you are not compelled to peruse every platform to figure out what people are saying — good or bad — about the product you’re selling and respond …

“You’re not doing well.”

However, there’s a twist.

Some details are more deserving than others.

“I spend a lot of time writing my scripts for earnings calls. I still memorize all those metrics and talk to different teams about how I can synthesize what they’ve done so I can make it interesting and compelling.

“We have an amazing team that can do that for me. But this really matters. I mean, it has to be me.”

The challenge is finding your own balance between staying in the details versus …

3. Establish Trust, Then Say No

Once people prove themselves, letting them pull their weight and take things off your plate keeps the company moving forward.

How does trust get established?

“You move up in trust when you say what you are going to do and do it consistently over time.

“When I find that I’m able to pull back a bit is when my trust is really high. They’ve consistently done exactly what they said they would do. And they’re doing it better than I can do on my own.”

The gift of trust is it allows you to focus more on fewer projects.

In other words, to say no.

“It’s easy to add. It is extremely hard to subtract — whether it’s projects, people, or priorities.

“Every time you add one more thing, you’re saying no to everything else.

“You have to say no. Founders and people leading companies really should focus on where they can subtract and get clear on what they’re doing.”

The result? Higher detail, care, and quality per project.

It’s a hard truth, but you can’t do too many things and do them all really, really well.

4. Set & Raise Expectations

High output demands high expectations. High expectations demand clarity.

People want to succeed and (at minimum) keep their jobs, so it’s important they know what you expect and where they stand.

But setting expectations isn’t enough.

“There’s something called the law of ecology. For a species to survive, it needs to grow faster than the rate of change in its environment.”

At Shopify, that law has led to all team members (including Harley) needing to requalify for their jobs annually.

I love this one because being up 50% YTD — 70% last year — at Jones Road has created all sorts of growing pains.

Many of them are rooted in the need to raise employee expectations in step with the business. Myself included.

5. Never Be Perfect or Done

Whether personal or professional, it’s in the nature of entrepreneurship to seek growth.

“They’re ambitious. But they’re not just ambitious with their business. The best entrepreneurs I know have an inherent desire to do better. To get better.

“When you combine getting better on a personal level and also making your company better, you get — I don’t want to call them unicorns, cause it’s a cheesy term — but you get these well above average returns.”

The trouble is …

Nothing stops growth like thinking we’ve arrived. That we’re done. That we or our business are perfect.

The more successful you are the easier it is to let that kind of thinking creep in.

“We will never claim that Shopify is perfect. We will never claim that everything works exactly as it should.”

Given that many of us have built our businesses on Shopify … perhaps there are no better words to end on than those.

Connect with Harley on Twitter (X) or LinkedIn. And be sure to check out Firebelly Tea + Big Shot — a podcast where Harley and David Segal interview other Jewish entrepreneurs.

THE FEED

Purpose Driven Business

Shopify President Harley Finkelstein

Sean Frank

CEO, Ridge

When and How to Fire

Let’s be real. Getting fired sucks.

Work has, for better or worse, replaced most “third spaces.” Your friends, your livelihood, and often your sense of purpose come from your job.

It’s a weird world we’ve built, but the fact remains — being fired is scary.

The first things you think about are paying rent, losing health insurance, and what this means for your future.

For leaders, common advice is: “If you’ve thought about it, it’s already too late.”

That sounds pretty cutthroat, right? What about coaching? What about training?

Firing someone is one of the hardest decisions in business, but it’s necessary. The key is knowing how to do it right.

If you’re in the position of firing someone, you need to be generous, decisive, and kind.

1️⃣ Be Generous

Whether you’re a founder, executive, or manager, you’ve probably been fired before. You know how much it sucks.

When you fire someone, you need to be generous. What does that mean? Severance.

Pay a minimum of 2-3 months.

And add another month for every year of service.

That could mean giving someone six months’ pay to leave, but think about it — if you got thrown out on your ass, how would you want to be treated?

Your current employees will judge you based on how you talk about and treat past employees. Be generous.

2️⃣ Be Decisive

Once you’ve made up your mind, act fast.

Legally, you need to document the process. Try a Performance Improvement Plan (PIP). Have a sit-down to express your concerns, but don’t drag your feet.

In my experience, PIPs work about 25% of the time.

(It’s a Hail Mary at best.)

Being decisive means being clear in your statement and tone.

During the meeting or call, say: “This decision is final. Nothing can change it. Let’s talk about what’s next.”

3️⃣ Be Kind

Always give your employees a reference letter and let them control how they tell the story.

You don’t need to save face.

If your business is successful, you’ll hire and fire hundreds of people over your career.

Better to leave on good terms than to make enemies.

The world is small, and the person you fire today could be the next Sean Frank tomorrow.

Trust me, you don’t want someone like that as an enemy.

Results

By following these principles, firing becomes less about punishment and more about doing right by your team, even when parting ways.

Generous severance shows that you care about people’s well-being. Being decisive avoids prolonged uncertainty. Kindness ensures you maintain professional respect and future relationships.

Your peace of mind is worth the cost.

Firing will never be easy, but it doesn’t have to be brutal. If you think someone should be fired, take a breath, write a PIP, but trust your gut — you’re probably right.

Firing isn’t punishment for them; it’s therapy for you.

Severance isn’t a gift; it’s you buying your peace back. Always offer severance, aim for at least two months. Let them file for unemployment.

Be clear, be firm, and let them tell their story however they need to. At the end of the day, if they call you the bad guy, so what? Being the “asshole” is part of the job sometimes.

TL;DR

Firing is tough. Have you thought about it? You’re probably right.
Severance buys peace. At least 2 mo. Let them file for unemployment.
Be clear and decisive. Once you’ve decided, nothing should change it.
Let them tell their story. If they need to call you names, who cares?

Connor MacDonald

CMO, Ridge

How to Pace Uneven Holiday Revenue

One common question we’ve received over the last few weeks is how to set targets for your business through periods where revenue is unevenly distributed.

Day-to-day projections are much harder when Black Friday can be >20% of monthly revenue.

So, I built an example sheet of how we look at previous year’s performance to better contextualize our performance to date + set projections for the future.

Is it a well-formatted spreadsheet?

No, some of my worst work.

Could it potentially be helpful to your business? Yes!

THE TRENDS

This week’s top-five trending news stories, curated by the editor of CPG Wire

1. LVMH Acquires Moncler Stake: Bloomberg

Luxury giant LVMH has acquired a minority stake in Moncler, an Italian purvey of luxury outerwear. LVMH will also take a seat on the company’s board of directors. Shares of Moncler surged on the news, and the company is now valued at nearly $18B.

2. Oak Essentials Secures Funding: Cosmetics Business

Oak Essentials, a California-based clean beauty brand, raised an undisclosed amount of Series A funding from Silas Capital and Unilever Ventures. Renowned fashion designer Jenni Kayne launched the brand in 2021.

3. John Paul DeJoria Buys Gin Brand: The Spirits Business

John Paul DeJoria — the self-made billionaire and founder of Patron Tequila — has acquired Waterloo Gin, a craft gin producer from Texas. Treaty Oak Distilling launched Waterloo Gin in 2009. The gin category has been on a heater from a fundraising and M&A perspective.

4. Scandinavian Biolabs Raises $4.5M: ArcticStartup

Scandinavian Biolabs, a Danish purveyor of plant-based hair growth solutions, raised $4.5M in Series A funding. French venture firm Aurea Group led the round. Existing investor Blazar Capital also participated.

5. Diageo Bets on Non-Alc Spirits: VinePair

Diageo, the global spirits giant that’s worth nearly $80B, acquired Ritual Zero Proof, the number one non-alcoholic spirit brand in the US. This is Diageo’s first acquisition in the non-alcohol space since it purchased Seedlip in 2019.

BONUS 📊 Q4 Ecommerce Forecast

Amid Sean Frank going back to back — “WE ARE SO BACK“ — on Q2’s ecommerce %-of-sales rebounding to 2020’s lockdown heights, Adobe Analytics released a record-setting Q4 forecast: $240.8B in online US holiday shopping.