Rick Holmes doesn’t need an alarm clock, keeps a to-not-do list, and walks to work every day. He’s also an award-winning executive and the CEO and founder of Every Market Media. We had the chance to sit down with Rick and pick his brain about pressing marketing challenges, maintaining creative freedom, and how a little meditation every so often is a key ingredient when it comes to being the happiest, most productive version of yourself.

Tell us how you got started. What brought you to Chicago and how has your career progressed?

To go way, way back to the very beginning, my first business – and I share this vocation with Hootsuite CEO Ryan Holmes, with whom I also share a name – was a paintball store. This taught me about running Internet businesses as well as digital marketing. Before that, I learned how to sell while working at a car dealership, and then moved to Chicago to work for Exact Data Consumer Base, a data brokerage firm specializing in email marketing. I started out as their first salesperson, building the sales division to a team of over 40. I was also responsible for landing Exact Data notable spots on both the 2011 and 2012 Inc. 5000 – Inc. Magazine’s annual list of America’s fastest-growing private companies. This was a first for the business, and an achievement I’m quite proud of. My experience there launched my career in data and I left in 2013 to start Every Market Media (EMM).

 What was the genesis for founding Every Market Media?

We built EMM around an email brand. We knew what we did exceptionally well and stuck to it. Market demand for exceptional email marketing software was the genesis, and striving to be really good at one thing is what motivated us. There’s a great lesson in focusing on one thing and doing that one thing better than anyone else. Multitasking is a bit of an untruth. A book entitled The Power of One cemented this way of thinking for me.

What does a typical day look like for you? How do you make it most productive?

My dog wakes me up around 6 a.m. I drink a cup of (good) coffee and meditate for fifteen minutes. I have the luxury of walking to work every day and listening to a podcast or audio book – always something related to sales and marketing – as I do this. The environment I work in is also very important to me. It’s much easier for me to be creative in my office – it’s my space. My better thinking hours are earlier in the day, so I’m in the office before 9 a.m. I try not to work too late and occasionally finish out the day from home. If I sense I’m not being productive in the office, I switch up my location. It helps with focus.

I’m religious about Google Calendar. I also rely heavily on Calendly for scheduling appointments – it’s the best nine dollars a month you’ll ever spend. I also make a point to only attend meetings where I can provide the most value and where I can drive the most impact. Most of my day is spent on sales and marketing and providing input on product direction and development through a lens of revenue and market demand.

How do you bring ideas to life?

It starts with reading and thinking creatively. You’re going to have a lot of ideas, and the majority of them won’t be viable.

Bringing good ideas to life requires you have a venue for them to be discussed with others. Not every idea is a “good idea”, and you learn you can table ideas – not because they’re bad – but because they’re better suited for another time. It’s important to cultivate a company environment and culture where ideas are constantly debated and people aren’t afraid to share what’s on their minds.

So, how do you decide to take an abstraction and make it a reality? You must first identify the business use case. A key part of that is asking: Why is this idea, the idea? Will your business make money from the idea? Does the investment make sense at this point in time? Your last step should always be to run your ideas by those you trust, and to make sure you capture various perspectives and vantage points. At the end of the day, a customer paying you for your concept time and again is the strongest indicator of a good idea, or in this case – product.

What do you consider to be the most challenging elements of modern marketing today?

Marketing is a multi-point solution. One of the greatest challenges is identifying what solution is right for – and at each – touch point. For example, to execute an outbound campaign, you need an intuitive email platform. You also need content and accurate lead data to ensure you’re connecting with the right audiences. It all comes down to determining what formula translates into ROI for your business.

One of the most challenging things is figuring out how to help people solve this for themselves. There’s an expectation that all digital solutions are a cure-all and do all of the hard thinking for you. In some cases, this is true, but you must be able to connect the dots across all marketing touch points. How do you manage the flow of outreach? Who writes the copy? How do you measure engagement? Some elements are more tedious than others but all are equally important. All of these efforts are individual dots that, together, make up a much broader and strategic effort.

When coming into a new company as someone responsible for overall operations and revenue, where do you start? How do you develop a well-oiled sales machine and ensure profitability? 

Business is about action, not talking about what you intend to do. Your actions also depend on the specific needs of the company. What’s everyone talking about and what is realistic? Answering this requires serious muscle, but, regardless of your charge, the first thing to evaluate is where your money is coming from. Next up: how do you plan to scale? What other ways can you convert what’s being done to appeal to a new niche? Product market fit is always a challenge for new businesses.

Often times, what you scale with isn’t what you came to the party with – it’s an evolving process. You have to look at who your customers are and what they’re paying you for. Ask, is it working?

As a startup, you likely have a big, fat mix of things customers pay you for. Isolating the one thing you do really, really well and serving multiple customers, regardless of industry or size, should be your number one priority.

As an entrepreneur and CEO, what do you do consistently that you recommend everyone else do too?

Never stop learning. This is important, but what’s more important is your attitude. This is something only you can control. Allowing yourself to completely clear your head is critical. Headspace is a fantastic app for this. Also, write everyday. Seth Godin says this, too. Keep a to-not-do list, and omit anything that distracts you from your top priorities. Everything else is just a distraction and prevents you from being truly successful. Constant multitasking is really just an effort to fill up an 8-hour day – focus is key.

Think about it through this lens: If I only did two things today, would those two things make me proud and feel productive at the end of it? Anyone who does 50 things in one day probably didn’t do any of them well or think about them with much depth. As a business owner, delegate what you can. But, if you can’t afford to delegate it – as in the business can’t pay for it – it likely doesn’t make sense for you to pursue at the time.

What do you look for when building a sales team and making those initial hires?

When it comes to hiring great salespeople, the first thing I look for is coachability. The second thing is curiosity, coupled with work ethic and intelligence. That said, above all, integrity is key – and this applies to all hires. Warren Buffet backs me up on this when he says if you don’t have integrity, everything else will kill you. The last thing you want is an intelligent, hardworking individual with zero integrity.

Curiosity is really important: if you don’t genuinely care about solving a problem, you’ll fail at sales discovery. Work ethic can be hard to define, but you have to set a threshold and see how quickly that person responds. These characteristics are pretty universal and you should figure out what works for your own company. Through that lens, you must identify your company’s intrinsic values and then hire based on how much an individual aligns with those principles. As a founder, I think many people underestimate the importance of company culture and how the environment you seed early on will follow you for the rest of your working life.