The Hardest Shift in My Career

I’ve come a long way in my five years of media buying.

In 2020, I was managing less than $5,000 per month for a struggling startup. Today, I personally place over $1MM/month on podcasts and have overseen more than $50MM in podcast ad spend across nearly 40 brands.

If you’re subscribed to this newsletter, you probably know me through LinkedIn or direct working relationships. LinkedIn changed my career—it got me my job at ADOPTER Media, and that opportunity has paid dividends tenfold.

Over the years, I’ve been invited onto a dozen podcasts (even ones hosted by direct competitors), spoken at Podcast Movement and PodSummit, and consulted with e-commerce brands and podcast networks. Somehow, I’ve stumbled into being a voice in the industry—so much so that my friends make fun of me.

Apparently, being a LinkedInfluencer isn’t that cool. My niece also doesn’t think what I do is cool, which is more important. I’m working on getting my new friend Gabby from Gabby’s Dollhouse on the podcast game—then I’ll be cool.

The way people now see me is a little daunting—not just my friends, but you all.

I didn’t know what I was doing when I started. Hell, I’m still not sure I do. But I’m here and hoping I’ve got a thick enough helmet.

And I’m grateful for the platform you’ve all given me to share my learnings—candidly and bluntly.

So, can I reflect with you for a few minutes? It’s helpful for me, and hopefully helpful for you. Let me walk you through how I’m building our media buying team at ADOPTER.

I’ve spent a lot of time psychoanalyzing my journey.

Why have I succeeded? Was I lucky? A fluke? Will it all fall apart beneath me?

My anxiety says yes. But when I break it down, I see patterns—not luck.

I don’t think I’m special, or that I know something others don’t about media buying—to be honest I think media buying is easy. But I have followed a few key principles that have guided my success that have nothing to do with media buying.

Where My Expertise Stands

If I had to put numbers to my media buying expertise across different channels, it’d look something like this:

• Podcasts: 85%

• YouTube: 60%

• Programmatic: 30%

• Streaming: 5%

• Radio: 5%

• Instagram/TikTok: 10%

• Newsletters: 20%

Thankfully, 95% of my job has been podcast media buying—and I’d like to think I do that pretty well.

I’ve bought thousands of shows, worked with dozens of brands, and collaborated with nearly every podcast network you can name. I’ve touched almost every corner of podcast ad buying—extensively and profitably.

But as my role has evolved, my biggest challenge isn’t buying ads anymore—it’s leading and developing a team of media buyers so our business can scale.

I’m no longer just responsible for the growth of my clients. I’m responsible for the growth of all of ADOPTER’s clients by guiding my team.

Educating and delegating is now my job.

And honestly? I’m still figuring it out.

The Scaling Challenge

Right now, the biggest challenge I’m facing at ADOPTER Media isn’t finding clients, or even scaling mine—it’s having account leads who can scale brands quickly and manage them effectively.

There’s no shortage of demand. But our ability to take on more brands depends entirely on our ability to train and develop buyers.

I trust my team with show selection. It takes me 1-3 months to train someone to pick good shows.

But confidence and client management? That’s the real challenge.

For example, we had a client stagnate under a newer buyer due to not understanding what the client actually wanted. The buyer brought high performance shows at rates that would work, but they weren’t hitting the mark on where the brand really was trying to go—eventually the brand was at a point of annoyance with us. The brand was trying to change their narrative, not just hit performance. They needed a reincarnation.

I jumped on the call with the buyer and client, we talked and it became clear quickly where we missed the mark. It was a misalignment with the brand’s direction, not that we picked poor performing shows.

The brand is now back on track, with new goals, new objectives, and new rosters of talent.

This isn’t a scriptable interaction. You need to know how to think/understand what the brand/client is communicating/wanting.

That’s real media buying.

The “Book of Trust”

Beyond being a good buyer, when it comes to my model of client management, it’s simple:

1️⃣ Know your shit.
2️⃣ Don’t lie.
3️⃣ Always be ready to scale.

1. Know your shit.

When a client introduces us to a new contact, I encourage them to grill me.

Ask me anything—past, present, future campaigns. If I don’t know my numbers, I have no business managing their budget.

For one client, that meant knowing the performance of over 500 shows and several million dollars of spend over two years.

When I answered every single question, they were dumbfounded.

Because I knew my shit.

That gets you into the Book of Trust—and that’s the book you want to be in.

2. Don’t lie.

If I haven’t worked with a show, I say so. If I think a client is making a mistake, I tell them. Transparency builds trust—hiding skeletons doesn’t.

Lying causes stress and bad decision-making. It’s not healthy for you or the client. Be blunt and honest.

That keeps you in the Book of Trust.

3. Always be ready to scale.

Clients don’t always give you a heads-up before dropping an extra $100K.

The worst thing you can do? Scramble.
The best thing? Have the plan already mapped out.

This builds confidence. It shows clients you’re on their team and ready to lead them.

🚀 Trust is the #1 key to scaling anything. People buy from people they trust.

Once you lose trust it’s extremely difficult to build it back up.

Bringing the Harvard Case Study Method to Media Buying

In college, I was lucky to learn business through the Harvard Case Study method—typically used in MBA programs.

My professor (now mentor) believed in teaching students how to think, not what to think.

The case method does just that: analyzing real-world business decisions from brands like Kodak, Lego, and Enron to uncover what worked (or didn’t).

It taught me to step back, analyze problems like a consultant, or as he put it “get in the helicopter and zoom out.”

I want my team to think beyond just media buying—to think like consultants.

If they can zoom out and see the bigger picture, they’ll become indispensable to clients.

I have clients who left ADOPTER who still reach out to me for advice on their brand/direction. Perhaps I should bill them, but I get joy out of knowing I am forever ingrained in their journey.

Every Ad Buy Has a Story

I want my team to have accountability and understanding on every decision. There’s always factors out of our control, but rarely if ever do we have zero control—I’m no determinist.

I’ve started writing case studies inspired by my college experience from real client and network experiences—breaking down what went well (or went completely sideways).

For example, I wrote a case about a client who was one of our top spenders, had a perfect product fit, an incredible amount of trust in us, and was scaling quickly.

Our rep had left in our first year of growth after the company made internal changes, and then we had another rep, then another, and another. We went through 5 different representatives. This was far more impactful on our ability to grow than our media selection. We were getting further from the source of decision makers and trust had eroded between the initial manager and the last. We didn’t have buy in or trust anymore so we were handcuffed to bad decisions, and poor management from the client.

Dissecting the narrative of this case, hopefully, will get my team thinking more about something that happens regularly—client rep turnover and how to build up trust when change happens.

Learn from my mistakes. And I’m being vulnerable in these cases as I am probably chief mistake maker here at ADOPTER.

That’s what I want my team to learn—how to diagnose real problems.

So, through 2025, I’m focused on learning how to teach. This is one method I’m imploring.

Outside of writing cases and doing case study sessions, how do you teach consultative thinking?

If you’ve successfully trained someone to manage clients with confidence, what worked for you?

Is this method of teaching going to work, or am I completely off base?

Let me know—I’d love to hear from you. ☕️

P.S. Dan Weinstock, if you’re reading this I hope my coffee tips help!