The Art of Harvesting

Happy Friday, Sippers,

⚡ TL;DR | Why the bravest marketing move in an annual planning cycle isn't pitching a shiny new pilot; it's deciding which brand to intentionally harvest so you can fund your future without begging for new money.

How was your week?

With October winding down, every leadership team I talk to is in the same pressure cooker: annual planning. Budgets are flat, expectations are 10x, and everyone is trying to figure out how to fund massive AI and digital transformations without a blank check.

When everyone is pitching net-new initiatives, it brought me back to an edition I wrote around this exact time of year about winemakers, hard choices, and the life cycle of great brands.

The lesson is even truer today than when I first put it down:

From the Vault | Harvest Season

As the harvest season for Canadian wines comes to a close, I've been thinking about what harvest means for marketers and the potential it offers.

When managing multi-brand portfolios, understanding where each brand sits in its life cycle is paramount to creating value, especially as requests to do more with less increase.

In its simplest form, there are three stages for any brand:

• Grow | Successful launch; the brand/product is gaining attention at a steadily rapid pace, and the focus is heavily on building awareness.

• Maintain | Levelling off from the rapid growth period; the focus shifts to differentiation and defending share against competitors.

• Harvest | Benefits from a deeply loyal customer base, but can only bring in net-new customers with massive, inefficient investment. It is basically the magic hour right before a steep decline.

Usually (and understandably), brand builders reflexively advocate for reigniting their legacy brands to keep them alive as long as possible with new packaging, PR stunts, and expensive repositioning campaigns.

A true harvest strategy is a calculated, disciplined commercial decision.

Deciding to pull back investment from a brand you love is emotionally heartbreaking. But it unlocks the ability to reinvest cash flow into high-growth, modern bets without asking executive leadership or finance for incremental "fake new money."

The clearest example I experienced was during our transformation at Yellow Pages.

It surprised nearly everyone on the outside, but the print phone directory was still generating hundreds of millions in high-margin profit with minimal incremental overhead.

By having the courage to harvest that cash cow rather than over-investing in futile attempts to rebrand print, we funded our massive digital pivot: acquiring 40,000 new digital customers in a single year and driving north of 70% of our revenue into modern digital products.

Every so often, consumers will surprise you and decide a legacy favourite isn't done yet. Think of the organic cult resurgences of Laurentide, Pabst Blue Ribbon, or Labatt 50.

But imagine if winemakers hadn't harvested the grapes at their prime to produce something new and delicious. 

Harvest is not all bad, after all. 

☕ The Sip Takeaway ☕ 🍷🍸

• Audit the Portfolio Honestly | Not every product on your roster needs to be a high-growth hero. Identify which brands are your cash engines and protect their margins without overspending.

• Create "Fake New Money" | If you want to scale AI infrastructure or digital video, stop looking outside for an incremental budget. Look at what legacy line items you can harvest.

• Discipline Over Sentimentality | Great leadership isn't defined by how many campaigns you launch; it's defined by having the conviction to sunset or harvest what has already peaked.

Until then,

See you next week