3 Entrepreneurial Marketing Tips for Marketers & Business Owners

Reggie Tan
9 min readDec 30, 2020

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Entrepreneurial marketing is a discipline or concept rarely taught in school, mostly because school doesn’t exactly teach entrepreneurship. Join me as we explore the three steps to achieving marketing greatness via entrepreneurship. In this post, I’ve combined four emails from my newsletter, Marketer Daily. Click here to subscribe to Marketer Daily for free.

If I could use one word to summarize most of my friends and acquaintances in college, it would be slackers.

That’s not to say I wasn’t a big-time slacker myself.

Prior to college, when I was taking computer science in university, a few visuals come to mind:

  • Drinking.
  • Sleeping in.
  • Sleeping in class.

Computer science just wasn’t my thing. I mean, I knew how to code, but when I started messing around with circuit boards and discussing the foundational differences between C++ and Java, my brain utterly shuts down.

I eventually left, with greater ambitions to move to Toronto and take the business marketing program at George Brown College. While I still couldn’t code Frogger in C++, one thing was certain: I needed to develop a stronger work ethic.

In college, most of my peers had other priorities. One dude sold t-shirts, another tried making it rich selling steroids, and a much shadier guy ran a business (stereotypically) selling car stereos.

While none of them made it past the second semester, it’s clear that they had one thing going for them. A drive for entrepreneurship.

Marketing programs rarely teach the concepts of entrepreneurship. The majority of courses provide skill-building opportunities, and if you’re up for the challenge, strategy-based learning.

Theoretically, entrepreneurship isn’t something that can be easily taught, nor digested. Aside from the functional stuff related to operations, entrepreneurship is mostly a mindset that is learned from experience.

The Financial Times states:

Entrepreneurial Mindset refers to a specific state of mind which orientates human conduct towards entrepreneurial activities and outcomes. Individuals with entrepreneurial mindsets are often drawn to opportunities, innovation and new value creation.

Characteristics include the ability to take calculated risks and accept the realities of change and uncertainty.

By combining your marketing skills with the mindset of an entrepreneur, you’re setting yourself up for even greater opportunities in the future. That includes taking larger roles in organizations, or even better, being your own boss.

There are many key characteristics of an entrepreneurial marketer, but for the next week, we’re going to focus on three that I personally think top the charts.

The stars will never align, and the traffic lights of life will never all be green at the same time. The universe doesn’t conspire against you, but it doesn’t go out of its way to line up the pins either. Conditions are never perfect. ‘Someday’ is a disease that will take your dreams to the grave with you. Pro and con lists are just as bad. If it’s important to you and you want to do it ‘eventually,’ just do it and correct course along the way.

— Tim Ferriss, The 4-Hour Work Week

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1. Become a self-starter

Under the umbrella of productivity, you’re either lazy or you’re not.

Unless you’ve been handed the keys to a successful family business, most entrepreneurs have to hustle to grow their business. Learning to be a self-starter is the difference between complacent and competitive.

You have to be ready to light the fire, whether you need to or not.

One of the most important characteristics of an entrepreneurial marketer is being a self-starter. Proactively, that may mean learning new skills to further your personal development in your off-time. Reactively, that’s brainstorming out-of-the-box ideas to drive website traffic to hit your monthly targets.

Self-starters understand that in order to become successful, it requires hard work, dedication, and doing whatever it takes to get the job done. It’s that extra effort that differentiates good from great.

This also aligns in the job market: you’ll typically see job descriptions with “self-starter”.

Unless your manager is a full-blown narcissist, people generally love self-starters because they don’t need to be managed. No hanging over somebody’s shoulder to make sure they’re putting in work. Self-starters can be trusted to work independently and require little supervision. Having someone on the payroll that clocks in and clocks out can become dead weight to an organization.

Thinking of running your own business one day? Being a self-starter keeps the lights on. Starting off as a consultant, or launching your first marketing agency, doesn’t suddenly mean potential clients will come knocking on your door. Building and launching a product doesn’t suddenly mean people will line up to buy. You’ll need to self-start in order to earn those leads. Self-starters focus on building their brand, networking their brains out, and generating content that provides value even before the client or customers show up.

As a marketer with interest in being a better marketer, just reading this email shows you have the capability to self-start.

Motivate yourself proactively, and you’ll self-start in no time.

Your work is going to fill a large part of your life, and the only way to be truly satisfied is to do what you believe is great work. And the only way to do great work is to love what you do.

— Steve Jobs, Apple

2. Learn how to fail fast

Here’s a quick reality check: you’re going to screw up at some point in your career.

Failing sucks. Trust me, as a Virgo, I’ve had to battle perfectionism for my entire marketing career. Perfectionism to the point of paralysis.

In an interview with Oprah, Dr. Brené Brown said:

People who are walking around as perfectionists are ultimately afraid that the world is going to see them for who they really are and [that] they won’t measure up.

Eventually you have to accept that you’re going to screw up.

As a marketer, one of the hardest things for me was, ironically, sending newsletters.

My first marketing assistant job was with John Hancock. Established in 1862, John Hancock is one of the oldest and largest North American life insurers.

Typical corporate setting: business casual, grey cubicles, standard work hours. And the biggest role of my job was to design and deliver weekly email newsletters.

I would meticulously review an email draft over and over again, to the point where I would delay delivery out of utter fear of screwing it up. I’m alright with sending a typo in a written email to somebody. What kills me is when I’m sending out a one-time email to thousands of people while representing an entire organization.

A blog post? Just edit it. A social post? Just delete it and post it again. But a newsletter? You hit send, that’s it.

Much like life, there’s no undo option.

I would literally sit there for an unfortunate amount of time with the mouse over the send button. Staring at it. Beads of sweat. Eye strain.

Eventually, after building up enough courage, I’d hit send. I’d almost always spring out of my cubicle and storm away from my laptop. Nope nope nope nope nope. Time for a smoke break. Except I didn’t smoke.

You know what? No matter how many times I checked each link and read each word, no matter how many people helped with final review. Even after countless hours of review, there would still be a typo or broken link somewhere in the newsletter.

In actuality: failure is inevitable.

There’s an old Latin saying. Repetitio mater studiorum est. Repetition is the mother of all learning.

I had to learn how to fail fast.

Over time, I overcame my fear of newsletter delivery (obviously, you’re reading one right now). I eventually realized that: 1) I never lost a job or client over a newsletter, 2) a typo or broken link was never truly a code red emergency, and 3) stressing out over matters that aren’t important in the grand scheme of things can be a massive waste of time and energy.

So whether that means sending out an email blast with a typo in the subject line, inadvertently tweeting from the wrong account, or falling short of your KPIs after an unsuccessful marketing campaign, the cards aren’t always going to fall in place.

What differentiates a resilient marketer and one that is not is the ability to fail fast. When a blunder occurs, the faster you get up, the better. Grab a mop and clean that shit up. Be quick to learn from your mistakes. Make sure it never happens again.

That being said, it’s important to own up to your mistakes. Covering up failures will eventually catch up to you. Be sincere and apologetic, but always have a solution ready.

The sooner you accept that failures will occur, the better marketer you’ll be.

However, that brings up the next question. What do you do when problems arise?

The real test is not whether you avoid this failure, because you won’t. It’s whether you let it harden or shame you into inaction, or whether you learn from it; whether you choose to persevere.

-Barack Obama

3. Be a master at solving problems

So far, you’ve figured out the “fast” part. But when problems arise, you have to be ready to create effective solutions.

When I was 8 years old, my neighbour (who was 2 years younger than me) approached me about a few bullies that were giving him trouble in the school yard. Karate Kid 3 had just been released in theatres, so I did what most Asian kids might do: I exploited the natural laws of stereotypes and, as I approached the bullies, did my best karate stance, and confidently proclaimed: “Stop bullying him, I know kung fu!”.

It worked. Problem solved. 🤷‍♂️

> If you want to read more of my personal experiences relating to systemic racism, click here.

Let’s oversimplify this for a moment. Defeating failure can be downsized into two steps:

  1. Stop feeling sad about it
  2. Figure out what to do next

The Manassa Mauler, also known as professional boxer Jack Dempsey, was known for coining, “A champion is someone who gets up when he can’t”.

Like a detective, resilience in business can be characterized in a basic workflow: Assess, Ideate, and Act.

  1. Assess

Ask questions to figure out what went wrong. How did the issue occur? Was there a breakdown in communication?

2. Ideate

Based on your observations, research your options and come up with actionable steps that can provide a solution to the issue at hand.

3. Act

Action speaks louder than words. Be decisive, and if you’ve harnessed it, trust your intuition. Create change to ensure the problem is not only solved, but also never happens again.

Does personal experience matter? Maybe. A good judge will typically come to solutions in court room scenarios based on a combination of past cases and the law. They’ll often refer to other similar cases and their outcomes in order to reach conclusions.

Sometimes, personal experience can include a level of bias that may or may not help. Keeping an open mind and continuously updating your personal experiences make for better problem solvers.

Once you’ve found a few unique ways to solve a problem or two, store them in your memory bank. Chances are you may need to refer to them in the future.

If you can’t fly then run, if you can’t run then walk, if you can’t walk then crawl, but whatever you do you have to keep moving forward.

-Martin Luther King, Jr.

My college dropout colleagues were exceptionally terrible at self-starting, failing fast, and solving problems, despite some of them being somewhat entrepreneurs themselves.

While experience in the field will allow opportunities to learn these key characteristics, it’s important to note that these attributes happen on a daily basis; whether you’re bouncing back from a poor mark on an assignment, figuring out how to change a diaper, or looking to buy your first home.

If you can learn these traits in your personal life, transitioning them into your career will make you an exceptional marketer.

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Many thanks!

Reggie ✌️

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Reggie Tan

Marketing aficionado. I write about growth marketing, entrepreneurship and Bitcoin payments. Subscribe to my Substack newsletter: https://marketer.substack.com