Getting People's Attention with Dave Gerhardt

Full Transcript

Lightly edited for filler words, false starts, and crosstalk. Speaker language and phrasing preserved.

Intro + talking some sh*t

Dmitry: Welcome to What's Your Process? Today I'm joined by the founder of Exit Five, Dave Gerhardt. Dave, how's it going?

Dave: Dmitry, good to see you, man. Thanks for having me. I'm a fan of yours and a fan of the pod — I host a podcast myself, so it's fun to be on the other side of the mic for once.

Dmitry: Before we get into it — what do people need to know about you?

Dave: My name is Dave Gerhardt. I'm a dad, a husband, I live in Vermont, and I've made a career as a marketer. I started by accident — I got an internship at a PR agency because it was one of the only places that would pay me anything. I ended up loving it, rose up through the company, and parlayed that into a career in marketing. I was CMO at a couple of tech startups that both got acquired, and then I started my own business — Exit Five, a community for B2B marketing professionals. We run an online community, do events, and create content, and I'm having a lot of fun doing it.

What is one thing you're world class at?

Dave: I'm a world-class copywriter — self-proclaimed. When I talk about copywriting, I don't mean the writing is necessarily beautiful. There are probably plenty of people who'd read what I write and think it's not great. But I think I'm excellent at getting people's attention, getting a point across, and finding a way to say that through words.

That shows up in a bunch of different formats. I'm the person in my family who helps my wife write a strong-but-not-rude email to the school. And professionally — last night I was rewriting an ad for one of our newsletter sponsors. We changed the headline, changed the image, made a bunch of edits, and the sponsor said, "This is way better." That's the thing I feel most comfortable doing and most invested in.

Dmitry: I love that answer, because there were a lot of angles I considered for this guest — copywriting was one, community-building was another. You were actually the first person I ever met who started a podcast.

Dave: That's how we met, actually — at HubSpot. The company I was at went out of business, and I had a podcast on the side. Mike Volpe, the CMO at HubSpot at the time, knew about it and knew I didn't have a home. He and Joe Chernov had this idea to hire a full-time podcast producer, which was a wild idea back then — nobody even had podcasts yet.

There's a connection between the podcast thing and the copywriting thing. I love storytelling, I love communication, and doing that many interviews built up a repository of knowledge in my brain. I can write a hook in a minute now because I've done it so many times before. And I'm constantly writing things down — I keep notebooks everywhere, because you never know when something becomes the topic for a newsletter later. I think one of the skills I've developed is that everything can become marketing and storytelling in some way, if you're curious enough and having enough conversations.

Dmitry: That's exactly it. Even with AI note-takers now, the notebook doesn't go away — the note-taker doesn't capture the nuance, the random thoughts you have in the moment.

Dave: Right — and I think there's something to the physical act of writing. Even if I never go back and reread the notes, writing them down helps my brain organize the information and increases the chances I'll remember it. I saw a clip of Marc Andreessen once — he said the person who takes notes in the room is often the one with the power. I was a religious note-taker early in my career, when I didn't have much to contribute in big meetings, and I think that's compounded into a skill over time.

What are you writing?

Dmitry: So how do you start? When you know you need to write something, what crosses your mind?

Dave: It depends on what I'm writing. If it's a landing page for a product launch or event, my first step is almost always to find one, two, or three examples of something similar that I think is good. Humans have been doing this forever — success leaves clues, and most of us are just building on what's come before in some form.

Sometimes I'll get a burst of inspiration and just freeform write — that's rare, you can't rely on it. Usually I start by finding inspiration first. Right now we're rebuilding Exit Five's newsletter, so I've spent the last week studying Morning Brew and Lenny's Newsletter, trying to understand what people love about them.

From there, it always starts with the headline or the hook — the general idea I'm trying to convey, not a polished tagline. And naming things matters a lot. If you name something, it sticks with people differently. We named our new event "Drive" — I didn't love the name at first, but now it's just Drive, the same way my son's name, Sam, felt strange at first and now it's just who he is.

Once I have the name and the concept, I try to begin with the end in mind. There's a book, The Presentation Secrets of Steve Jobs by Carmine Gallo, that breaks down how Jobs was such a compelling presenter — the whole secret was starting with the soundbite you want people to walk away saying, and working backward from there. With Drive, it was: what do we want people to say about this? Let's make that a reality.

Dmitry: What I love about that is it goes against the classic advice of "write the subject line last." You're doing the opposite — getting in people's faces first and filling in the rest.

Dave: Yeah — a teammate of mine, Erin, does our content, and every single email or newsletter she sends me, I rewrite the subject line. I don't just tweak it, I delete it and start over, every time. She once asked if she should even bother writing a draft subject line, and I said yes — because having something there helps me react faster. It's like the naming example: the first idea is never the final one. You have to edit. There's a saying I use all the time: great writing is just great editing. I'll write 5 or 10 subject line options, figure out which parts I like, and build my own from the pieces. Tools like ChatGPT are great for this — I'll give it the concept and ask for 15 variations, then pull from a few of them. I don't think I'm a beautiful writer. I think I'm really good at piecing things together.

Just write it.

Dmitry: So you've figured out what you're writing and found your inspiration — what happens next?

Dave: I just write it. I go until I hit a stopping point and try to get as much down on paper as possible, then go back and edit. Formatting is a hugely underrated part of writing — we run our business on Slack, and it's easy to write a wall of text nobody's going to read. You eat with your eyes first. So after I get the thoughts out, I reorganize into a clear headline, sections, grouped points — "here are the three reasons," "here are the five benefits." I like guardrails like that. I used to work on websites and hated it, because everything felt infinitely possible — instead I'd say, here's the homepage, it has these sections, what goes in each bucket?

There's a framework I got from that Carmine Gallo book — story, problem, solution, call to action. Tell a story to hook someone in, introduce the problem, show the solution and back it up with examples, because humans operate on stories and clear examples. Then close with one clear ask. The thing that drives me nuts is competing CTAs.

There's a quote I use all the time, from a book called The Wizard of Ads by Roy Williams — a friend gave me a couple of his books years ago. It's: "the risk of insult is the price of clarity." In my old homepage example — the risk of insult is that the VP of Partnerships is upset her thing didn't make the page. The result is that people actually understand what you do and take the next step. So much of marketing is a chain of "next step, next step, next step" — not trying to explain everything at once.

I'll give a specific example: I hate when people write "click here" and only hyperlink the word "here." I'll link the whole sentence and bold it, because I want people to read the whole thing, then click.

Dmitry: A lot of what you're describing comes back to focus — having a point and getting people where you want them, instead of throwing a bunch of stuff out and hoping it sticks.

Dave: Right. Keep it simple, be clear, be direct.

Consider the stakes.

Dmitry: You've written it, formatted it — do you just hit post or send, or is there a secondary process?

Dave: It comes down to what we're working on and what the stakes are. We have a new event this year, a marketing leadership retreat in Arizona for CMOs doing $100 million-plus in revenue — the page is exit5.com/retreat. We spent a lot of time on that, sweating every word, because it's a new audience and there's a personal letter from me on the page. Multiple rounds of feedback. That's the goal — not to rush it, to get it right.

Something like a LinkedIn post is different. I wrote today's post on the treadmill in about ten minutes. If there's a typo, someone will point it out and I'll fix it later — the stakes are lower. Something like our email, though, I love writing with deadlines. Time-boxing is your friend. Our newsletter goes out every Tuesday and Thursday — there's a clear deadline, and it's like homework: it's due, and the grade's already been written.

Dmitry: Does the newsletter go out if you haven't seen it?

Dave: No.

Dmitry: So as the founder, you get to make that call.

Dave: Well — let's level-set. We're a media company; the newsletter is the product, it generates revenue, it has sponsors. If I were a SaaS founder, maybe I wouldn't need to sweat every email — every founder has an area where they add unique value, and for our business, this is mine. It's changed over time — I'm not writing it zero-to-one anymore, we have writers. I'm more at the end of the line, making changes, leaving my fingerprints on it. But there's someone at the end who cleans it up after I've made my pass — I don't need to see it again after that. My life wouldn't be possible if everyone waited around for me to give final approval on everything.

Ship it and learn.

Dave: The message I try to give our team is: I'll edit it, I'll give feedback, and I'll also give feedback after it's gone out — not to criticize, but to say "this came off weird, let's tweak it for next time." I believe quality matters, but a lot of times as marketers and creators, we let quality become an excuse not to ship.

Dmitry: What I love about this is that even though something is important, you can still experiment and learn. I've seen the newsletter shift formats — sometimes a list, sometimes a personal note, sometimes takeaways from an event. Too many teams sit and wait until something is "perfect" before shipping, and that's not a real standard — you can't learn that way.

Dave: Exactly — we're okay with shipping things I'm not fully confident in because we've done it enough times to know I'm sometimes wrong. Multiple times I've thought "this isn't our best," and it performs great. And the reverse — something I spent forever on and loved completely flops.

We're also living in an era where you get feedback almost instantly. You don't need a quarter's worth of sales data like old-school advertising did — you post something, and you know within a day if it landed.

Actually, our newsletter is about B2B marketing, but you know what our highest-performing content has been? Writing about how people work — what hours they keep, how they manage their day. People love that. It's not scientific, it's a gut feeling based on the response, but now we're intentionally building more personal content into the mix.

Dmitry: That tracks with something I heard at a Zapier event recently — someone pointed out that in spaces like ours, we're all creating content for the top one or two percent of experts, when the other 98 percent just want to know what it takes to succeed and what people they respect are actually doing.

Dave: Right — and that's fine, as long as you're intentional about which slice you're writing for.

What's next?

Dmitry: So — we've shipped it, we've learned from it, found new inspiration. Where can people see your process in action?

Dave: exitfive.com and LinkedIn — that's it. If you listen to this and it resonates, send me a note, I'll try to reply.

Dmitry: Thank you so much for the time, Dave.

Dave: Thanks for having me — this was a great way to actually think through my own process out loud. I'm going to want a copy of this recording.