The Best Marketing Education Likely Won’t Come From A Course
Lessons learned: PR intern to CMO to Exit Five founder.
I spent about a decade in marketing before founding Exit Five, working my way from PR intern to CMO. Ten or so years ago I landed what was then my dream job at Drift: 28 years old, backed by top-tier VC firm Sequoia Capital, with Pat Grady on the board, fresh off taking HubSpot public. I was the first marketer at the company, with a real shot to put my name on something.
My boss at the time, David Cancel, Drift’s founder and CEO, and certified marketing genius, decided early on to make me his project. He sat me right next to him, fed me books like Ogilvy on Advertising and Seth Godin’s Purple Cow, then quizzed me on them. DC loved this quote by Dan Kennedy: "Thou shall not care about what friends, family, or yourself think. Results rule." Timeless.
David Cancel, Casey Neistat and me, in my Drift Days
I get a lot of credit for the marketing we did at Drift, but so much of it came from DC - he oozes creativity and marketing, and it was contagious. We’d go for lunch everyday, and take a 2-3 mile walk after, hunting for an iced coffee and a treat.
We came up with our best stuff on those walks, from riffing on podcast topics to billboards and taglines, even pacing the streets of San Fran prepping for a Forbes briefing on our Series C announcement. But the best idea we ever had was Drift’s "No Forms" slogan, our first real viral marketing campaign. We didn’t need a six-page positioning doc to explain our product value, we boiled it down to one crossed-out word on a sticker. If you can get to that level of clarity, you nailed it.
I didn’t know it at the time, but this was my apprenticeship. This was my MBA in marketing (even though it felt more like Navy SEAL training at the time).
So much of what’s good in my life came from putting myself out there. Shoot your shot.
I got the Drift job because I had David Cancel on my own podcast. Drift was about to raise funding, and someone suggested I have him on my show. That night I saw they were hiring a marketer on AngelList and applied on the spot. The next morning their recruiter emailed to say I’d been rejected, not a fit. A couple hours later, the same recruiter followed up: David liked me from the podcast, did I still want to come in? I got the job.
Personally, things were moving fast too. I met my wife Lya at a bar in Boston so crowded they sat us at the same table - she was pretty AND laughing at my jokes so I took my shot. We got married, and not long after, Annie was born, one of the first Drift babies and an instant celebrity around the office.
I became something of a celebrity myself: all the attention on Drift had people DMing me a lot on LinkedIn, so I just posted the answers publicly. Everybody thought I was a huge dork for it, LinkedIn wasn’t cool yet, but I did it anyway.
One Halloween in Boston, a stranger stopped me on the street: "You’re DG from Drift, I follow you on LinkedIn." Embarrassing at the time, but proof it worked - real people were connecting with what I was putting out. Five years flew by, I maxed out LinkedIn’s 30K connection cap, and by the time I took the CMO job at Privy, Lya and I had two kids!
Me in 2020, running webinars from my closet.
Then 2020 hit, and everything changed. We went from an office full of people to working entirely from home. I was running webinars from my closet. Instead of whiteboarding with my team, I was listening to Gong calls on the Peloton and watching Loom videos. Pretty lonely.
Not long after, AI showed up and made it worse in a different way. Why talk to a person when I’ve got Claude in my pocket?
But I keep coming back to the fact that so many of the good things in my life came from what I was putting out into the world, shots I took. I got the job at Drift from a podcast conversation - not an impressive resume. That nerdy LinkedIn habit led to 205K+ followers and even talks to join Harvard Business School’s faculty (didn’t do it but pretty cool for little ol’ me). My beautiful family. Shoot your shot!
The best ROI on your career likely won’t come from AI. Put yourself in the right spaces and connect with real people.
Whether you’re at Drive in Stowe this week or reading this from your desk, solid advice. My business partner Dan and I met ~9 years ago at Drift. I later brought him to Privy, then Exit Five. He says it best: "Exit Five is a people business."
Nothing beats real human connection beyond the slide decks, the office, or even Claude(!)
If you’re feeling isolated from working remotely or need inspiration beyond the office, the answer isn’t more AI. This is why Exit Five exists, a space for people who get what you do for a living.
We’ve seen this play out through examples like Dasha Shakov and Jess Cook, who met over dinner at Drive last year and bonded over how hard hiring is. Jess told her to start writing on LinkedIn - she did - now she’s got tons of followers and co-hosts the Exit Five podcast with me.
Arthur’s here too - he connected last year with someone who wasn’t even hiring, and now he runs customer and community at Storylane. Everyday, marketers use the Exit Five community to crowdsource solutions to their challenges, talk to people who get it, or just vent about their boss. Just a few examples of the connections that happen when you put yourself in rooms with the right people.
I’m a marketer, so I wouldn’t do anything without a CTA - here are a few that I gave the Drive audience this week, but I think they apply to those of you at home too.
- Meet someone new. This is what the Exit Five community is for. If you haven’t joined already - do it. If you’re in there - get involved. Find the person with your job title and challenges or company you want to know more about and say hi.
- Be real. Open up about what’s actually going on at work - the only way to get real advice from people who have been there and can help.
- Be like “vacation Dave.” I admit, my default is head down, avert eye contact. But I’m different on vacation, approachable. I have a character I call 'Vacation Dave,' the version of me that says hi first. Whatever your version of that looks like - lean on that character as needed to get out of your comfort zone.
Vacation Dave: Activated.
AI’s in my pocket too! It can’t replace these things. Get out there and create real life connections.
- Dave
PS - Are you at Drive this year? What’s been your favorite part so far? Or are you home with FOMO? Reply back and let me know.
PPS - Lots more Drive content and takeaways coming. Sorry not sorry.
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