How To Avoid Burnout & Thrive In Marketing with Dmitry Dragilev & Kage Spatz

Marketing Strategy Series by

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Dmitry Dragilev Marketing Expert

If you knew you were not going to make a penny doing what you’re doing now, would you still do it? If the answer is “no” or “maybe” — perhaps it’s time to rethink what you’re doing.

As a part of my Marketing Strategy Series, I’m talking with fellow marketing pros at the top of their game to give entrepreneurs and marketers an inside look at proven strategies you might also be able to leverage to grow your business or career. Today I had the pleasure of talking with Dmitry Dragilev.

Dmitry Dragilev is the founder of and He was previously Head of Marketing at CrossLoop as well as PolarPolls. Dmitry also runs SmallBizTools — a blog where he tests, rates, and reviews the best business software tools for people who want to save time and stay on top of the latest software.

Thank you so much for doing this with us! Can you share a story about the funniest marketing mistake you made when you were first starting and what lesson you learned from that?

My very first gig as a marketer was in 2007 as a part-time intern at — a tech support marketplace. Mrinal Desai was the co-founder of the company and took me under his wing. He showed me how to “reach out” (using email or social media) to journalists and bloggers and get them to respond.

I saw how he built a relationship with Walt Mossberg of Wall Street Journal through IM, email, and twitter — and I was hooked. Walt was the tech columnist at WSJ. He co-founded AllThingsD, Recode, and was the executive editor at The Verge and other Vox websites. Of all the journalists in your rolodex that you wanted to get noticed by, he was a big deal. Mrinal scored this fancy article about CrossLoop in WSJ.

I was so impressed with this, I wanted to do the same.

My first full-time job as a marketer was at a design firm in Silicon Valley called ZURB (I was the first marketer the company had hired). The design firm consisted of five or so designers, a few developers, a few partners, and myself as the marketer. PR and publicity is something they wanted me to focus on. In my first few weeks on the job, I learned that the team had been hard at work building an app called Notable for web designers to solicit feedback on their designs from their clients.

I remembered that awesome article we got in WSJ about CrossLoop… maybe I could do the same for Notable? I emailed Walt Mossberg, mentioned I was formerly from CrossLoop, and had another awesome story for him. He responded rather quickly and agreed to take a demo call. I was pumped! Just weeks into my new job and I scored such a huge PR opportunity.

We had to rush the developers and designers to put together a live demo we could show. Bryan Zmijewski the founder of ZURB was the one who would demo Notable with me to Walt Mossberg. Here is how it went:

Walt: So… you fellas have a personal tech product you’ll be showing me today?

Me: Well, it’s not really personal tech, it’s more of a umm… just tech. You’ll love it.

Walt: Ok. [Awkward silence]

Me: So this app we’re building, well we are going to launch, it’s for web designers to get feedback on their designs. Here is how it works…

Walt: Wait, hang on right there. I focus on consumers, you know that right? I write about gadgets, phones, personal technology, software… but it’s for consumers. I don’t cover B2B.

Me: Yes, 100%. We are a consumer software company. Our app helps designers get feedback on their designers from clients, consumers, their family, whoever they need to.

Walt: Ummm. [Awkward silence]

Me: So, here is how it works. Pretend you’re a designer and you need to get feedback on this mockup from a client…

Walt: Mockup? Dmitry I mentioned to you I do not cover B2B. It sounds wonderful but it’s not something I can cover.

He hung up the phone. Bryan and I just looked at each other awkwardly for a while before we got up and left the room.

I was too excited about the connection with Walt from my old job that I forgot he only covered consumer tech. This is a mistake plenty of marketers make, they assume just because they created something amazing that the journalists, reporters, bloggers, podcasters who will see will be automatically interested in it.

My lesson learned — take the time to study what journalists, reporters, bloggers, podcasters actually care about, what are their curiosities, which questions do they ask day-to-day.

One More Funny Mistake: Another very small mistake comes to mind as well since we’re talking about ZURB. When I worked there I ran a speaker series called ZURBsoapbox where I interviewed big names in Silicon Valley, founders of Twitter, LinkedIn, Eventbrite, WordPress,, etc. This one time I had Matt Mullenweg founder of WordPress coming to the interview and I was beyond excited, he was a big name and we were sold out, the house was packed.

There was one little issue though: the house was packed and Matt was nowhere in sight. It was so packed it was hard to move around and I was on constant lookout for him. I was worried about going over capacity since many people brought friends who we let in as well, the fire marshall would shut us down if he saw what we were doing. I saw some dude who squeezed through the entrance and ran straight for the bathroom, he looked like a bum who has not taken a shower in a while.

I told a colleague: “Can you just wait by the bathroom door and get that guy out of here? We’re already overcapacity.”

The response from my colleague was: “You get him out yourself!”

I squeezed through the crowd and saw the bum exit the bathroom.

I yelled at him so he can hear me: “Hey, you! Do you have a ticket? Did you register for the event? We’re over capacity and can’t fit anymore people here.”

He turned around and said “Well if you don’t want me here, I guess I’ll go. I thought you want to interview me?”

It was Mall Mullenweg, he just did not shave for a while and grew out his hair. I felt like such an ass!

My lesson learned — Make no assumptions or preconceived notions about how people look and prepare for the interview properly so that there are no surprises.

Are you able to identify a “tipping point” in your career when you started to see success? Are there takeaways or lessons that others can learn from that?

When I worked at Polar we had a crazy small team: two co-founders, an engineer, a designer, a social media manager, and myself as the marketer.

We got funding from Yahoo founder Jerry Yang and my job was to get this polling app as much publicity as possible. I tried a ton of stuff and nothing really moved the needle as much as we wanted to.

I then came up with this crazy idea of reading Techmeme and greetings polls. I would read Techmeme and look for a headline I can create a poll about. I would pick a breaking news story and create a poll about it. I would promote it on Twitter and then pitch it to press:

Subject: Got a poll for you: Which Foursquare logo do you prefer?

Hey Chris-

Made a poll for your article asking which Foursquare logo people like the best, check it, might be fun to get your readers more involved to get more to come back to the article: (link to poll)

Here are how these polls look like live: (link to an article where a poll was already being used)


Journalists would respond and say “Yes, would love data I could include in my post.” Eventually, they started embedding our polls in their articles.

I used this exact same process for 2 years and lined up relationships with all major media outlets: NPR, TechCrunch, Mashable, Wired, Forbes, Entrepreneur, ReadWrite, The Verge, GameStop, Financial Times, you name it!. We went on the front page of most Hearst publications — San Francisco Chronicle, San Antonio News, etc. I used to bookmark all the articles we’ve published with these polls.

So this in a way was a tipping point for me, I didn’t realize that a no-name kid without much prior experience can build relationships with all major media outlets and grow a startup so quickly to acquisition all without hiring a PR firm, or any outside consultants.

The other thing which surprised me was my hit ratio, one out of three emails I sent came back with a “yes”. When I thought back on it I realized that it was the Quality vs. Quantity approach that I focused on. I cherry-picked the most relevant journalists and found the most relevant data for them and pitched them one by one. I never spammed hundreds of them at once with one email.

The lesson learned for others is less is more, quality over quantity really pays off. If you’re sending an email to anyone (be it marketing or sales email) — read it out loud to yourself, would you say this to the recipient face to face in real life? Be honest with yourself. If the answer is “no” or “maybe” — rewrite that email.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are?

Mrinal Desai, the co-founder of Crossloop was gracious enough to offer me an internship in 2007 at his startup and show me how to pitch journalists without any prior experience. I owe my career pivot and everything that happened after that moment, to him.

What advice would you give to other marketers to thrive and avoid burnout?

I’d say this: If you knew you were not going to make a penny doing what you’re doing now, would you still do it? If the answer is “no” or “maybe” — perhaps it’s time to rethink what you’re doing.

Life is short, it’s too short to waste on stuff which “just makes good money” or “is just a job”.

Love that advice. What do you wish someone told you before you started?

#1 If you knew you’d never make any money from what you’re doing now, would you still do it? If not — stop what you’re doing.

Back in 2009, I interviewed Philip Rosedale — the guy who created SecondLife — a very popular virtual reality game at the time. In this interview, he asked me this question and it really helped shape how I go about what I engage in.

#2 Live your life like you’ll die in 6 months.

I interviewed Patrick Byrne, the former CEO of back in 2009 and he was told by doctors he had six months to live. Six months came and went and they told him he had another six months. Eventually, he recovered. But he trained himself to live six months at a time knowing fully well he could pass away at any moment at the end of six months.

This completely changed how he approached life, time with his family and friends and work. We typically spend time on things that are not important. This type of mentality helps you focus on what matters most.

What books, podcasts, documentaries or other resources do you use to sharpen your marketing skills?

  • Experts On The Wire Podcast by Dan Shure — best SEO podcast out there.
  • Brian Dean’s blog — this is the only SEO blog you need to read on the web, I’ve been reading it for years now, amazing content here.
  • Fractl Blog — these guys are so good at creating case studies and data and pitching press — amazing content here.
  • How Will You Measure Your Life by Clayton Christensen, author of Innovators Dilemma.
  • How Will You Measure Your Life TEDx talk.
  • Simon Sinek — How Great Leaders Inspire Action TED Talk.

One more before we go: If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

Not too long ago I posted this on Indie Hackers, it sums up my movement well: If you don’t have to work a 9-to-5, don’t do it. I mostly work half days…

“If you don’t have to work a 9-to-5, don’t do it. I work half a day. When I pick up the kids, I stop working, and if I don’t get everything done that day, it can wait another day. My partner in one of my businesses is so completely opposite. He’s on 24/7, taking calls 24/7, traveling all the time. He used to tell me I need to push more and build the business faster so we can exit and get acquired. And of course, I want it to succeed. I want to grow it. But in the grand scheme of things, I want my relationship with my family to be amazing, and that takes priority. I love playing around with them, hearing them laugh, hanging out with my wife, and being engaged with them instead of thinking about business. So, in my mind, if my kids are at home and I’m working, it better be insanely important. My business partner and I just think about life differently, and that’s fine. We worked it out. He knows me. He’s used to it. He makes fun of me for it. Because you don’t have to kill yourself and work crazy hours unless that’s what you want to do. Everybody’s got their own path to follow — I want to work less, spend time with my family, be outside. You know, take a walk and just experience life.”⠀

Work less, spend less time thinking about money, spend more time with your family. Too many of us are being pushed and rushed by this world we created for ourselves, for no apparent reason. Culturally (in the U.S. especially) people take less time off and spend less time with their family. Even if they could, they don’t.

The mentality among marketing professionals is “Do more in less time”. My movement would be the opposite — do less in more time. If you have the luxury of rearranging your life and controlling things that much, of course.

There is so much value here — thank you for sharing so many important insights with us!

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