Edition # 6 How I Became Idiotically Optimistic

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 yeah—Performance Max Advanced is going LIVE, and Black Friday is around the corner. I’m sharing some of the resources we use at AdVenture Media for Black Friday prep.

Let’s start with this: we rarely talk about how we judge our own decisions. And that’s a problem.

Too often, people measure success based on outcomes alone. But let me tell you, that’s a slippery slope. The quality of a decision isn’t determined by what happens next—it’s all about the process you used to get there.

You can do everything right, gather the data, make the call, and still, the result might not go your way. Doesn’t mean the decision was wrong; it just means life threw you a curveball.

The key is sticking to a solid process, trusting your instincts, and moving forward with confidence—no matter what. Because real pros know that it’s not about chasing perfect results. It’s about making smart decisions and adapting as you go.

And while we're here, I want to take a second to say thank you. The feedback on our new courses has been absolutely amazing. We put our heart and soul into them, and seeing how they’ve resonated with you all is everything.

If you haven’t checked them out yet, do yourself a favor—they’re waiting for you in the Academy.

“If you don’t know where you are going, you will probably end up somewhere else.”

- Laurence J. Peter

Unfiltered Stories From the Heart of the Agency: Chapter 6

How I Became Idiotically Optimistic

AdVenture was just Danny, Juan Tejada, and me. It was early 2015 (I think), and my first piece of content—a one-hour AdWords tutorial on YouTube—had been relatively successful.

Prospects were calling the number in the video … and we were signing them. Actually, Danny was signing them. I think his record back then was five new clients from the tutorial in a single day. We were charging peanuts back then, but it didn’t matter. The sales gong was ringing.

The top comment on the YouTube video was, “I’m five minutes in and this guy is so damn boring I’m looking for my fu%#ing pillow,” so I decided to make a full-length course.

The problem was I didn’t know the first thing about online courses. I didn’t know how to operate a mic or a camera. I didn’t know how to edit footage. I didn’t know how or where I’d sell the course. All I cared about was making the course ten times better than anything else out there. And to me, better just meant longer, or more thorough, or more polished, or maybe a little bit of all three. I had no real plan. Seriously.

I bought some books, enrolled in some online training, and spent the next six weeks learning as much as I could whenever I could. I learned about tripods, microphones, softbox lighting, audio filters, editing software, and that digital cameras had more buttons and settings than a 747 cockpit.

I bought a used camera from B&H and the cheapest possible (but serviceable) lighting equipment and microphone I could find on Amazon. Frayde and I were living in a 500-square-foot studio apartment at the time. Besides the kitchen (which was just a stove and a sink in a corner), there was one other room, which much to Frayde’s dismay, I turned into a makeshift recording studio. I dragged our only couch into the stairwell and pasted a stick-on whiteboard along the wall. The softbox lights glared off the whiteboard’s glossy coating, so I lined the apartment ceiling with aluminum foil, bounced the light off the aluminum foil and lit the whiteboard indirectly. Oh happy day.

I filmed fifty lectures over the next four months. Had I known what an agonizing drudge this would turn out to be, I never would have started the project. It was brutal.

It took me about fifteen hours to edit every hour of recorded footage—and that’s not an exaggeration. The audio was being recorded into an old iPhone, which had to be synced with the camera’s audio. All the mistakes had to be edited out, graphic overlays had to be incorporated, slide decks and screen recordings had to be matched up and overlaid onto the videos—and many times, entire lectures had to be re-recorded because I forgot to hit the record button on either the camera, the mic, or both.

It took me four hours a day, every day, for four months. But we still had a bunch of clients to manage—and new business coming in, and Frayde was always making noise in the apartment—so most of the filming and editing happened through the night. One night, around 3:30 am, I tripped over a tripod, fell into the wall, broke the camera, woke up Frayde, woke up the neighbors next door, and woke up the divorced lady and her son living below us. It wasn’t pretty.

I spent the next three months building this absurd WordPress LMS to sell the course through, which was nearly as horrible of an experience as shooting and editing the material itself. But finally, we launched, selling the course for $499 (limited time sale but obviously not limited time at all for $299). When the first sale came through, I remember jumping out of my seat and giving Ari a hug.
But there was only one hug, because there was only one sale.

A few weeks later, someone mentioned to me in passing that they were taking a photography course on Udemy. I checked Udemy out, and it looked like an interesting platform. It took another two weeks of editing, cutting, and formatting to comply with Udemy’s policies, and then I had to wait another week for Udemy to review and approve the course. I had to write a new landing page for Udemy, shoot another promo video, and jump through thirty more senseless hoops.
Finally, in November (again, I think 2015), the course was live on Udemy. It generated 9 sales. I was pretty damn dejected. What a colossal waste of time. But in December, the very next month, fourteen thousand students bought my course.

Fast forward a few years, and we have four courses with over 280,000 students across 185 countries. The courses brought us Forbes, AMC Networks, Adorama, and hundreds of other prospects and clients. I hope the success of the course played a role in inspiring Patrick to write and publish Join or Die—another idiotically optimistic undertaking that had no reasonable chance of succeeding. But it did.

It usually doesn’t pay to be idiotically optimistic, but that’s not the point of being idiotically optimistic. It’s much more than that—it’s a worldview, an intrinsic orientation, a state of being—and when it does pay, the positive ripple effects continue to reverberate in entirely unexpected ways.

What's Going On at AdVenture

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This gave me a good laugh... 

Build Your Holiday Audience Early

A Thought on Advertising

Invest in growing your audience now to boost your remarketing power during the holiday season. The more prospects you engage throughout the year, the more conversions you'll drive when the spending spree begins.

Utilize last year’s holiday shopper list to create lookalike audiences. This means Meta will find new users who share similar behaviors and interests with your previous spenders, giving you a fresh, high-potential audience. Run low-cost video campaigns to warm them up and set the stage for stronger remarketing results during the Holiday season.

The screenshot below is from an account we used this tactic with last year ;) 

We’re giving away our 2024 Black Friday Mega Guide, which covers everything you need to prep for Black Friday, to all newsletter subscribers (yep, free). Download it here. 

We also collaborated with customers.ai to create an advanced Meta Ads strategy guide for Black Friday. You can download it here (yep, again for free). 

If you’ve already got the Ultimate Digital Advertising Library, it’s sitting there under The All-Inclusive Toolkit along with a ton of other holiday strategies.

If you don’t have it yet, now’s the time! We just packed it with new courses you’ll need before the holiday rush.

Grab it before the price jumps up on October 2nd. Plan smart. Save big. Don’t wait.

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