Why We're Starting a New Podcast

This is the first episode of Agency Breakthrough, a second podcast ZenPilot launched in 2023 in cooperation with ClickUp. There’s no guest. Gray MacKenzie and Kuba (Jakub) Grajcar, ZenPilot’s head of marketing at the time, explain where the idea came from, what counts as a breakthrough, how each episode is structured, and then try the show’s recommendations segment on each other.

Where the idea came from

The spark was a conversation Gray had in San Diego that February with the person who leads growth at ClickUp. Agencies are one of ClickUp’s four core market segments, and both companies wanted content for agencies working on their ops. The name came later. Gray’s family does what they call special time: one parent, one of the four kids, a quick date every Thursday morning.

My daughter and I went to the library because she is an avid, avid reader… She was reading a series of books… and I was doodling on my sketch pad. I wrote down agency breakthrough.

(Listen at 09:53)

There are plenty of agency podcasts about growth, marketing, hiring and ops, Gray said, and plenty of “I went to college, accidentally started an agency, and 20 years later I’ve got a 50-person team” interviews. He wanted something narrower.

What I want here is the sweetened condensed version of, hey, here’s a meaty problem that I was stuck on and we were bumping our heads and we were scraping our elbows against the wall, trying to solve this. And eventually we found something that worked really well. And I want you to be able to take that as motivation and inspiration. And I also want it to be practical application of, how do I learn from that?

(Listen at 10:58)

What counts as a breakthrough

Kuba credits Gray with the name but took on defining it.

Sometimes what you need is that breakthrough moment that changes everything… The moment when you find the lever that you can pull that just gives you outsized results, or just the one framework or the one mindset or whatever change. Sometimes it might be a hire. Sometimes it might be a refocus, going broader, going narrower. The thing that you do that just changes your agency for the better, for good, and in a huge way.

(Listen at 08:42)

The listener’s breakthrough won’t be the guest’s. If a guest focused on PPC, the lesson is the thinking that made it work, not PPC. Gray’s example of the kind of story he wants is Dean and Ryan at Worth, an email agency that took Upwork clients through a small, clearly scoped project, converted them to monthly retainers, layered in outbound, and sold a couple of years later at over a 7x multiple. His follow-up question: would the same business get that exit today, or was it timing? Kuba wants that honesty built in.

I would be happy if we asked enough questions where our guests, some of them, would honestly reply that part was just luck. And that’s why you can’t replicate every breakthrough… I think we have to be honest about these stories too.

(Listen at 15:01)

Three acts: context, breakthrough, crisp cornucopia

Gray asked Kuba to lay out the structure.

Once the guest is on, we’ll first ask about the context: what is the scale of the agency, what are the numbers that they’re willing to share, just so you understand whether you’re listening to an agency of 50 or 500 or over many million in revenue… Act two, what Gray just discussed, the breakthrough story, in a simple chronological way: what was life before, what was the breakthrough, what is life now after the breakthrough, and also trying to help you replicate this, or replicate the thinking that led to it.

(Listen at 12:38)

Act two also covers the pitfalls, the places where a different turn would have meant no breakthrough. Kuba expects the format to change and figures they’ll laugh at this episode in a few months. The third act is the one he named.

What we’re calling the crisp cornucopia. So just a lot of rapid-fire recommendations… Everybody has that secret tool or secret weapon that they never shared about. But actually, there’s this agency that we use for 70% of our content, and they never shared about it. So we want to uncover that as well, to help you find the right people to work with, the right tools to work with.

(Listen at 13:48)

Gray added service providers: who do you use for accounting, PM consulting, sales consulting, HR.

The first cornucopia: the hosts’ own picks

Kuba’s two were a podcast and a book. Tiago Forte’s Building a Second Brain (he recommends the free podcast over the book) is a system for capturing what stands out and mapping it to an area, so the next talk on marketing or leadership comes together in minutes instead of hours. Todd Herman’s The Alter Ego Effect is about adopting a persona for each context in your life. Gray’s three were small productivity tools. Reflect for notes, with every task living in ClickUp. Superwhisper for fast, accurate voice-to-text he pastes into Slack, ClickUp, email or a ChatGPT prompt. And TextExpander, which ZenPilot uses company-wide so a few keystrokes expand into email addresses, URLs and form fills, and one change shows up for everyone. He threw in TypingMind, a better interface for ChatGPT with saved prompts.

The plan was to release the first five episodes together. The guest Kuba was most excited about was Marcus Sheridan, whose They Ask, You Answer he followed like gospel as a young marketer. He couldn’t sleep the night the yes came in.