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The Wednesday Windup Archives

Explore past issues packed with our best digital marketing insights and stories.

Edition # 7 I Burnt the Midnight Oil Oct 02, 2024

Welcome to this week’s Wednesday Windup. As I sit down to write this, Rosh Hashanah is just a few hours away. For those unfamiliar, Rosh Hashanah marks the Jewish New Year—a time of reflection, renewal, and gratitude. It’s an opportunity to look back at the year behind us,...

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Edition # 6 How I Became Idiotically Optimistic Sep 25, 2024

Welcome back to the Wednesday Windup. It’s 2:30. Grab your coffee, drop the to-do list, and let’s hit reset for a bit.

Today, we’re diving into decision-making—why it matters, how we mess it up, and what it took to launch my first course over a decade ago. Oh, and...

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Edition #5 Rules For Life Sep 18, 2024

Fair warning: This is a long one—but it’s worth it.

It’s 2:30 in the afternoon, which means you’re probably hitting that slump, right? 

So go ahead and grab your coffee (or tea if you’re more refined than I am). Take a deep breath. Now let’s shake off...

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Edition #4 Like You Do Sometimes, Grandpa? Sep 11, 2024

Have you ever been on a video call with a bunch of other people, and innocently, very innocently at first, you start checking your email (a slippery slope indeed, because you're really still working) and before you know it you're shopping for flannel throw blankets, checking the price of...

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Edition #3 There's No Beer in the Third Period Sep 04, 2024

Hi. Welcome back to the Wednesday Windup. This week, I want to share why I constantly repeat to my team—almost at nauseam—the phrase: Ready, Fire, Aim. I believe it’s the only way to truly move forward and make progress.

 The world loves Ready, Aim, Fire—sounds...

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Edition #2 You Remind Me of Me Aug 28, 2024

In advertising, we all face those moments where everything seems against us—the algorithms aren’t cooperating, client demands are sky-high, and the data feels discouraging. It's like the last stretch of a tough journey, where you're tested to your limits.

This past week, I took on a...

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Edition #1 Prove The Bastards Wrong Aug 21, 2024

Let’s be real—Wednesdays are tough. It’s that awkward middle child of the week, not close enough to Friday to feel hopeful, but far enough from Monday that you can’t complain about it anymore. And then comes the 2:30 slump. You know, that time of day when even your coffee...

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Each Wednesday, get expert Google & Meta Ads strategies delivered right to your inbox. It's an unfiltered glimpse into the wild, unpredictable world of digital advertising. We’ll share our biggest flops, the strategies we salvaged, and the lessons that turned it all around. You’ll leave with practical takeaways—and the comfort of knowing that even the pros have been where you are now (and learned a lot of it the hard way).