18 Take-Aways from 18 Years as a Marketing Entrepreneur

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In December 1999, I walked out of my final agency into life as an entrepreneur. Flush with $700 in my pocket, I saw nothing but possibilities. Before the door closed though, I learned my first lesson…

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Know when you’re looking a gift horse in the mouth

An account executive at the agency I was leaving asked if I might be interested in doing a PowerPoint presentation as a freelance gig. Having come from ‘creative’, bloated ego and all, I said something to the effect of: “why not give it to the secretary?” I didn’t mean to be rude but my comment certainly was.

A week or so later, I ran into him again and asked if he had found someone to take the job. “Yes,” he replied… “and then I gave him the rest of the project.”

Double take-away #1: It’s fine to turn down work, but don’t let your pride get in the way. New clients will test you.


No one can do it all, in fact, you can’t even come close

Still stinging from the first lesson learned, I organized a group of ex-agency peers for mutual support. Basically, the very type of people you’d find inside an agency. Our team grew to 16 and we eventually gelled into two groups: managers and creators. The creators attracted clients, but were quick to turn them over to the managers for stick handling.

Take-away #2: Seek out others who have complementary skills to your own. It really does take a village.


Working from home can be very isolating

A lot of people find that, when they set up shop in a home office, they have trouble staying motivated. Social media, noisy kids and pets, and the latest Netflix series can all pull you away from your desk. For that matter, so can a sunny day or a craft beer break with friends.

I experienced the opposite: I could never stop working. I lost count how many times a trip to the refrigerator resulted in making one more edit on a brochure or web page late at night. A few years in, I realized I needed to get away from my house if I was going to keep my sanity – so I rented my first space in the back of a sign shop.

Take-away #3: Know how you do your best work and arrange your surroundings to fit.


Value-based pricing keeps you in business, hourly billing can kill it

For the first few years that I ran my freelance business, I charged by the hour. That attracted all kinds of business, and led me to a curious realization: each time I raise my rates, I got better clients.

Take-away #4: Value and efficiency open the door to profitability.


Monday is a week away, not a weekend away

“Let’s talk on Monday.” Sounds okay, doesn’t it? Well that depends. While we tend to think of Monday as coming after Friday in the sense of a work week, it’s truly in the next actual week. Waiting until Monday to do something makes it feel like there’s been a delay. For the past decade, we’ve arranged reporting on Thursdays and Fridays whenever possible.

Take-away #5: Setting deadlines earlier can reduce stress and feel faster.


Your business chops are always being tested

You haven’t really lived the life of an entrepreneur until you’ve had to walk into a room and pitch your services knowing your team needs a win to pay their mortgage.

Take-away #6: You have to stay sharp and hungry, and incredibly tenacious.


When you give away the secret sauce, you sell more of it

This is one of the most important lessons I ever picked up. I can remember countless times during my agency days, and even as a freelancer, when other designers would tell clients as little as possible of the mechanics of a project. They were working hard to protect their jobs by restricting knowledge.

It still happens. Ad agencies, digital firms, and freelance professionals routinely build moats around themselves in an attempt to keep their skills in demand. That seldom works though. People thirst for knowledge, or more pragmatically, they want to know what they’re paying for. And, they have access to youtube. The cat’s been out of the bag for along time.

Take-away #7: Show others the value you provide and they’ll appreciate you.


Customers aren’t always right, but they do pay the bills

Its okay that I don’t always agree with my clients. Any time I’m being a yes man, I’m likely doing them a disservice. While I’m confident in my work, I remind myself that clients know more than I do about the finer points of their businesses. At those times, I have to listen if I want to get it right.

Take-away #8: Choose your battles wisely.


Clients will pay for services that simplify their day

People want convenience, and they also want value. It’s important to provide both of these things, and to be careful about the way we present them.

Around 15 years ago, I remember invoicing a client for travel time, taking a view that my time was valuable regardless of whether I was designing a logo or sitting in traffic. However, that view wasn’t shared. I later added a project management fee to my invoice to cover all the miscellaneous activities involved in making a job successful. The invoices are a bit bigger, but clients pay them without question.

Take-away #9: Avoid the perception that you are nickel and diming your client.


Managing perceived value is at the core of business success

A well-known local steakhouse came to me after two years of promoting deals to tour buses with 2-for-1 ads in a coupon book. They faced two challenges; low revenue from entree sales, and difficulty keeping their best servers.

Secret shopping the restaurant, I noticed that I was being stingy with my tips, and realized that the low cost deal created a perception that the steak dinner was worth only half the price. Busloads of hungry bargain diners were coming to the same conclusion, causing the servers to work very hard for smaller tips.

Once the offers were changed to add-ons (free appetizers, endless refills, etc) rather than discounts, their staffing and profitability issues disappeared.

Take-away #10: Be careful about the way you present your offers for you risk devaluing your worth.


Pivoting can be great for business

If you’ve been around me at all for these past eight years, you probably know I’ve survived a battle with stage IV cancer. Surviving that illness gave me a new outlook on life, and on how I wanted to run my business.

Previously, we were order-takers, giving companies exactly what they asked for without any regard to what would come next. In 2013, we changed that, turning down projects that would have brought in money, in favour of projects that would build our clients’ businesses as well as our own. The result, finalist for Small Business of the year 2013.

Take-away #11: It’s okay to say no to opportunities that don’t fit.


Business leaders should handle their own social

In a lot of organizations and agencies, social media marketing interactions are relegated to an outside firm, or possibly an intern. That’s understandable, but believe me, it’s a mistake.

Social networking is all about building relationships. And as we all know, trust is the key to any relationship. Using social media well isn’t about publishing or posting, it’s about making connections and showing up. If you went to a real-life event once, few people would never notice you. Go regularly and then miss an event, though, and the whole room will be asking where you are.

Take-away #12: Social media done right is a networking activity.


Hiring is hard, cloning is impossible

If you’re an entrepreneur, you’ve probably wished you had a clone. Or, perhaps you wish you could hire someone just like you, with the same skills and attitudes you have to share some of the weight. It took me a while to accept that nobody does what I do. They do what they do. Hiring is always a challenge, and a little bit of a gamble.

Take-away #13: Look for employees who can complement your skills and talents, not duplicate them.


Finding inspiration on competitor sites

Almost every new client I meet with will look at their competitor's websites before redesigning their own. It’s just too tempting not to. There’s nothing inherently wrong with measuring yourself against the competition to be sure your prospects can see the value offered. But, doing so can come at a cost. When you don’t take the time to think through your own challenges and solutions, you’ll never be in a position to lead your market or industry.

Take-away #14: Replicating things your competition does makes you a follower, not a leader.


Potential clients judge billing rates just like they do portfolio samples

Charge too little and you won’t just seem under-qualified, you’ll find yourself working for lesser clients; set your fees too high and you could lose out on the business. In my experience, it’s better to be on the higher end of the scale than the lower side. You’ll do better financially, of course, but you’ll also attract better clients who value your work, experience, and input.

Take-away #15: Consider volunteering before joining a race to the bottom.


No single achievement leads to success

In my business, achieving a number one position in Google search rankings is often thought of as the end-all, be-all marker of success online. However, that’s not really accurate. Anyone I know who’s achieved high rankings has spent years building their company’s brand through sales and marketing, networking, promotion, and more. It’s cumulative.

Take-away #16: Overnight successes rarely are.


Ignorance definitely is not bliss

Sometimes, I like to try to convince myself that I’m the very best at inbound marketing and lead gen. Then, I crack open a nice craft beer, dig into my social feeds, and find dozens of people who have things to teach me on a daily basis. I’m constantly reminded that there others who are smarter, faster, wealthier, or better-connected than I am. There are things I can learn from all of these people. Rather than let it get me down, I seek out their knowledge.

Take-away #17: Every time I learn something new, I grow.


Embrace your copilots

As an entrepreneur, I have faced endless challenges – both financially and personally. It can be isolating being the boss, and overwhelming to have the fate of your dream on the line on a daily basis. I’m fortunate to be part of a handful of entrepreneurial groups full of very nice and insightful people who are walking similar paths.

Take-away #18: Cultivate friendships among your peers.


Beyond that, the one overriding lesson I’ve learned – and maybe the one that means more than all the others – is to simply keep running. There’s no substitute for perseverance, and I’m living proof that you can get through any trial or mistake, no matter how painful the time, if you just stay focused on the better days that are yet to come.

is your website design delighting your prospects? it should be.

Topics: business strategy