“5 Things You Should Do To Upgrade and Re-Energize Your Brand and Image” with Jack Choros of Little Dragon Media

Keep it simple. Most of the time when people think about a rebrand they imagine a major overhaul, but rebranding doesn’t have to represent a seismic shift. Google rebranded its logo many years ago simply by changing the colour of the letters that make up the word Google and using a different font type. The company faced criticism initially but explained the reason for the simple rebrand was the fact that they wanted their logo to be a reflection of the user experience they hope to give to people when they search for something on the web. Simplicity.

As part of our series about “Brand Makeovers” I had the pleasure to interview. Jack Choros. Jack is a branding and marketing expert for Little Dragon Media in Toronto, Ontario, Canada. He has been working as a freelance writer in the space for nearly a decade and served corporate clients in various verticals including the Canadian cannabis, digital marketing, investing and blockchain technology.

Thank you so much for doing this with us Jack! Before we dig in, our readers would love to “get to know you” a bit more. Can you tell us a story about what brought you to this specific career path?

I began writing about sports as a hobby because I’m a sports nut. Although it was fun I started in my mid-20s and realized that I was becoming interested in trading my own stocks. After learning some and failing a few times, I decided to start reading the basics of how to manage your own investments. Before becoming a writer I started out as a banker so I already had a financial background and I realized writing about finance was a better way to sustain myself as a freelancer. I’ve also always had a penchant for business so I became more and more interested in how sports teams and the corporate world in general handles marketing and branding. I wanted to know what separated the contenders from the pretenders and thus, more and more of my work started to come from the marketing and branding arena. I wouldn’t say I planned it that way but that’s where I am today.

Can you share a story about the funniest marketing or branding mistake you made when you were first starting? Can you tell us what lesson you learned from that?

The first marketing and branding mistake I ever made actually came way before I even knew I would end up where I am now. I was an intern at a sports marketing firm and social media was still new. This was back in 2007. My boss commissioned me to try and learn about how we could use social media to get more athletes interested in our marketing services. My mistake was investing a ton of time into MySpace. It was the biggest social media website at the time, and it had gotten to a point where people were using it as more than just a music platform, but in hindsight it was really silly to think that we could somehow connect with athletes there or learn anything about how to build a following. It wasn’t too long after that MySpace was completely dead in the eyes of the public. The lesson I learned was that you have to hang out where your target audience is, and you have to recognize when a platform is dead.

Are you able to identify a “tipping point” in your career when you started to see success? Did you start doing anything different? Is there a takeaway or lesson that others can learn from that?

Because I didn’t start my career with the intention to end up in branding and marketing, my story is different from most experts in the field. My tipping point came when I downloaded an internet marketing course by a famous multimillionaire and marketer named David D’Angelo called Marketing Step-By-Step. It was the first time I had ever been exposed to the idea of creating a customer avatar, understanding the pain points of your target audience and learning how to develop products and services that cater to that audience. Sure those elements of branding and marketing are fundamental and very basic, but that course sparked my success. Now I know that whenever I’m working on a new freelance project, my first task is to understand who the target audience is, where they hang out, how they talk, and what problem they are trying to solve.

Are you working on any exciting new projects now? How do you think that will help people?

At the moment I am working with a mobile app company on a Canadian cannabis project as well as working with a digital marketing firm. The app wants to be considered a go-to resource for cannabis news and advice on which strains to use along the lines of major competitors like Lyft or Leafly. The digital marketing firm wants to cater to local business owners who don’t have time to handle their own online marketing. I can certainly help people find the right cannabis strain for their needs and I’m hoping we can help local business owners focus on what they do best. In fact, that’s the main reason why anybody hires me, because they don’t want to spend the 70% of time that it takes to truly implement a proper marketing strategy. They want someone else to handle the marketing while they enjoy the 30% of time that most business owners spend on the fulfilment of the actual work it takes to run their apps and websites and sell their products and services. In other words, they want to spend their time working in the business whereas a marketer works ON the business.

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

The advice I would give is to keep things fun and always put yourself in the end user’s shoes. One way to do that is to always be brainstorming new ideas, even if some of those ideas are for a fictional client that doesn’t exist. Sometimes it can be fun to exercise your brain without having to meet a deadline or accomplish a specific objective. This is especially important to think about when working in a corporate setting. So many corporations have a structured way of handling their branding and marketing. They want to meet five times a day to discuss every little change to a slogan, website or advertisement, but they spend very little time actually fulfilling work or brainstorming. The whole point of being creative is to think outside the box. Intentionally spending time being creative without limits is what avoiding burnout is all about in my opinion.

Ok, let’s now jump to the core part of our interview. In a nutshell, how would you define the difference between brand marketing (branding) and product marketing (advertising)? Can you explain?

To me, brand marketing has a broader scope. A strong brand name can be home to many products, but a specific product is meant to be a solution to a specific problem. One good example would be a brand like Dyson. The average person knows that Dyson makes high-end vacuum cleaners. What they may not know is that Dyson also makes blow dryers that live in public bathrooms and dry your hands. Dyson is a brand synonymous with a high quality, efficient approach to managing cleanliness and personal hygiene. They know this because of Dyson’s effectiveness at employing a brand marketing strategy. Product marketing on the other hand is more specific. Dyson sells a lot of blow dryers to public facilities, but you won’t find ads for that on TV. The real beauty in that is that people who run public facilities recognize the name brand from vacuum commercials and already understand the value proposition of the brand without them necessarily having to be influenced by advertising or product marketing initiatives that relate to installing dryers in public restrooms.

Can you explain to our readers why it is important to invest resources and energy into building a brand, in addition to the general marketing and advertising efforts?

It takes a lifetime to build a brand, but only a day to destroy it. While building a brand is fragile, most companies have a branding and goodwill column in the Assets section of their balance sheet. Branding and goodwill has an actual monetary value. The reason for this is because people always remember the name of a strong brand and when that brand decides to expand its line of products or services, even if the product or service itself has little to no traction in the beginning, people will trust in it because they trust the brand name.

Amazon is a good example of that. When Amazon first launched, it was only a marketplace for selling books. Not only does Amazon now sell everything under the sun, the company is involved in completely different categories of business outside of simply selling products. Amazon Prime is not just a membership that offers free shipping, it’s now a streaming service that competes with Netflix, Hulu, Disney+ and other services. Amazon Web Services is a cloud storage service catering to both individuals and businesses. Amazon Mechanical Turk is a crowdsourcing marketplace that makes it easy to outsource small tasks.

None of these services is in the same category as the others but they all operate under the brand name of Amazon. Amazon’s brand is so strong today that the company can literally move into any vertical and crush the competition. That’s why branding is so important. It’s the difference between building a single successful service or product line and building a company that leaves a legacy for generations to come.

Let’s now talk about rebranding. What are a few reasons why a company would consider rebranding?

There are many reasons a company can consider rebranding. The biggest reason companies should rebrand is when their mission is outdated. Pretend for a moment that American Express decides to move away from the credit card business and cut ties with major banks. Instead the company realizes that Bitcoin is the new frontier. Its mission to “…be the world’s most respected service brand” could become “to be the world’s most respected financial technology company”.

Trying to recover from a major controversy is another reason to rebrand. But a rebrand doesn’t always have to be triggered by something big. A company may decide to go after a different segment of their target audience and narrow down their brand messaging to something very specific. That’s all it really takes.

Are there downsides of rebranding? Are there companies that you would advise against doing a “Brand Makeover”? Why?

There can definitely be downsides to rebranding. A strong brand sticks in the minds of the consumer. A rebranded product or service might not gain traction in the same way. If a company has worked really hard to come to the top of the consumer’s mind and then re-brands, they risk losing all of the goodwill they have built up.

Sometimes companies re-brands just to try to cash in on whatever’s trending in technology. Employing such a strategy is definitely not a good idea as a brand makeover. One good example of this comes from the 2017 Bitcoin boom. When everybody and their mother was catching wind of digital currencies, companies that have nothing to do with blockchain technology tried to cash in.

Long Island Iced Tea is one example. They added the word blockchain to their company name and saw the share price of their stock skyrocket, but the company really wasn’t ready to be in the blockchain business, nor does their target consumer really care whether or not they use blockchain technology to sell their tea. The company is still moving ahead with its plans, but the rebrand was a nearsighted move that really didn’t plant any seeds from a marketing perspective that will grow the company’s market share in the long term.

Ok, here is the main question of our discussion. Can you share 5 strategies that a company can do to upgrade and re-energize their brand and image”? Please tell us a story or an example for each.

Work with celebrities that fit the new image.

J.Crew is a clothing retailer that sells capri pants and tank tops. The company was struggling in the early 2000 until they hired the former CEO of Gap clothing Millard Drexler. It was Drexler that decided the company should work with former First Lady Michelle Obama. The company now generates millions of dollars in revenue every quarter.

Copy brands your company wants to be like.

R&D doesn’t just stand for research and development, it also stands for rip-off and duplicate. McDonald’s built its name selling really tasty hamburgers quickly, but everyone knows those hamburgers aren’t good for you. Walk into a McDonald’s today and you’ll see that the food menu includes many different salads and the restaurant itself looks more like a Starbucks. McDonald’s wants to keep up with the times both in the design of its restaurants (which look more like cafés now) and in its offerings on the menu.

Position the brand differently in emerging or new markets.

Pabst Blue Ribbon is one of the cheapest beer brands money can buy across North America. College students love it because it’s one of the few beer brands they can afford to buy consistently. Try buying Pabst Blue Ribbon in China. It’s going to cost you many times more. That’s because Pabst Blue Ribbon is quenching the thirst of Chinese people who want to buy a high-end alcoholic beverage. It costs nearly $50 for a case there. Different market, different branding strategy.

Change the company logo

Changing a logo or slogan is usually the first thing people think about when they imagine a rebrand. It’s the kind of thing a small business owner would do if they didn’t have a budget to run a mass scale marketing and branding campaign. That doesn’t mean big companies don’t do it, and you don’t have to look too far back to find a good example. Instagram.

The original Instagram logo features what looks like a Polaroid camera as the logo, but a simple tweak to the colours gives the new logo a more modern look that matches what everybody probably thinks a social media website’s logo should look like.

Keep it simple

Most of the time when people think about a rebrand they imagine a major overhaul, but rebranding doesn’t have to represent a seismic shift. Google rebranded its logo many years ago simply by changing the colour of the letters that make up the word Google and using a different font type. The company faced criticism initially but explained the reason for the simple rebrand was the fact that they wanted their logo to be a reflection of the user experience they hope to give to people when they search for something on the web. Simplicity.

In your opinion, what is an example of a company that has done a fantastic job doing a “Brand Makeover”. What specifically impresses you? What can one do to replicate that?

Apple is probably the best and most impressive example. The company stood firmly behind Microsoft for decades in terms of both market share and brand awareness, but the vision of Steve Jobs turned Apple into the world’s first trillion dollar company in 2018. The current Apple logo is much sleeker than previous versions of the logo were in the 70s, 80s, and 90s. I’m also impressed by how the company managed to create the iPod and iTunes. The two platforms became a better way to listen to music and consume media. They catapulted Apple into the stratosphere along with the iPhone which would come years later. Apple is a great case study for pushing forward rebranding and product extension in a way that changed the world.

Other business owners and branding and marketing professionals can replicate that by focusing on design and the user experience. It’s also important to focus on how your brand can build a moat, in other words, how it can carve out a share of the market that it can exclusively own above all other competitors. Apple does this really well. The company makes the cost of switching to Windows or any other operating system very high. Try asking an Apple customer to trade in their iPhone, Homepod or Macbook for three comparable products that are all compatible. It’s a very costly move.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

The movement I would inspire would be one of inclusivity and accessibility. In the social media and digital age we are currently living in, any branding or marketing effort that doesn’t acknowledge the importance of inclusivity will be left behind. The future is one of openness and acceptance. Every brand and every company should embrace this.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

My favourite quote is not a life lesson necessarily but it encapsulates the way I think everybody should live. It comes from Hellen Keller, a blind and deaf activist who broke barriers related to accessibility and acceptance for an entire generation of people. Keller once said, “Life is either a daring adventure or nothing.” I believe that everybody should strive to make their life a daring adventure. Take chances in your branding and marketing efforts. Do things you’ve never done before. Live for something, not for nothing. This quote is relevant to me as a person with a disability and a creative mind who hopes to inspire those that come after us.

How can our readers follow you online?

Twitter @jackchoros. Facebook https://www.facebook.com/JackChoros

LinkedIn ca.linkedin.com/in/jchoros

LinkedIn is the best.

Thank you so much for these excellent insights! We wish you continued success in your work.


“5 Things You Should Do To Upgrade and Re-Energize Your Brand and Image” with Jack Choros of Little was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.

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