AMA: How to Market Like You Give a Damn, Breakfast Like a Founder, Brand + Demand, Etc.
The team wanted a mailbag/ask me anything episode (or maybe I asked for it? Classic ego thing…), so I sat alone in my co-working space and answered your questions rapid fire, on the fly. My takes on everything from giving a damn about marketing to overnight oats. Let’s get into it.
What’s the most underrated marketing investment?
Easy: giving a damn. Everyone’s in a rush to automate with AI, but great marketing takes empathy and craft, like Mailchimp sending hand-knitted hats for customers’ cats and turning it into a viral campaign. Another example: I write an email to my kid’s school knowing I have to walk in and show my face to the teacher, so if it’s sloppy, that’s a reflection on me. Empathy means asking when you last sat through a webinar live without multitasking, then using that lens for the one you’re creating.
How do you balance brand building with bottom-of-funnel?
We always think it has to be either/or, but you can do both. The real question is how you justify spending on something that doesn’t directly relate to sales, and the answer is to show the CEO and CFO how people buy from you and give them a vision for how you do marketing. Nike didn’t only do direct response. Neither does Hula, the co-working building I work out of. They grow by hosting events and bringing in interesting people to share their stories.
What would your first 90 days look like as head of marketing?
Everyone’s gonna hate this answer, but there is no playbook. Everything works, from webinars and ads to direct mail and TikTok, so you have to figure out what you can actually pull off with your team, talent, and budget. (Everyone says hire A-players. Well, what if you can’t?) In B2B, it all comes back to how you can be the top resource for your customer. Nobody just sees an ad and buys!
Do AI outbound BDRs work?
It doesn’t matter if it’s AI or human. The only real measure is whether it’s working in your company. I learned this from John Barrows years ago: your outreach needs to answer why you, why now? If you can figure out how to do that with AI, why not?
How did you make Exit Five feel like a community vs audience?
I never thought of them as different. Those are just marketing words. The biggest thing has been being real, showing my face, and writing 10K comments, because people want to know there’s a human on the other end. You need to show you’re listening too. A boss once told me his team asked for better snacks in a survey, and he went and got them that afternoon. That feedback loop really matters.
How do I create strategic clarity and lead my peers?
Incentives drive behavior, period. Show me the goals of the company, and I can show you what people are gonna be doing or not doing. Usually the reason you can’t get on the same page with sales is that they’re not incentivized to. Spend more time with your CMO, understand what’s important in her job, and learn how to serve her better. Or not. What do I know? I’ve worked for myself for a while now.
What’s the biggest hype story that gets busted in six months?
Definitely AI. Both things can be true: it’s very useful, but it’s also a bit of a bubble. (I’m not an investor. This is not investment advice.)
How do you answer a pod question you weren’t prepared for?
I’ve never had a problem saying “I don’t know that” or “I don’t wanna answer that.” What are the stakes, really? We’re on a planet we have no control over, and I’m on a podcast being interviewed about marketing. Not a big deal.
What do you eat for breakfast?
This is a commercial for overnight oats: half scoop of rolled oats, a scoop of protein powder, two big globs of Siggi’s Greek yogurt, a dash of milk, and a tablespoon of chia seeds. It takes five minutes at night while I’m loading the dishwasher, has about 40g of protein, and keeps me full until lunch. Otherwise it’s two o’clock and I’m at the gas station eating Doritos and a weird protein shake.
I’ll keep saying it: There’s no B2B marketing playbook
There’s no secret to any of this. Everything works, and you have to figure out what you can really pull off. If you ship regularly, you get a lot of at-bats and a lot of feedback. So it’s day to day, week to week: get more at-bats, feedback, make changes, and listen to people. That’s the only way I know, really.
