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Marketing Advisor, Mentor, & Educator

Kevin C. Whelan

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May 7, 2025

Will AI replace marketers?

There’s a lot of questions swirling among marketers (and knowledge workers in general) about how AI will impact their professional futures.

So, I decided to record a quick video on how I see things going.

The short answer is, you’ll probably be fine. But things will definitely be different.

Watch my thoughts over on YouTube → 

March 7, 2025

Why you don’t need perfect content to be successful

Do you feel stuck trying to create content?

What if I told you it didn’t need to be perfect to be successful?

What if “good enough” was.. well… good enough?

There are two ways to think about it:

  1. You create content at a high frequency
  2. You create content at a high fidelity

Ideally, you mix both together. You sprinkle in lots of base hits and go for the occasional home run.

But in order to do that, you need a plan.

The main things I see stopping people from creating content are:

  1. Lack of time
  2. Lack of confidence

You might find that creating regular, quick, simple pieces of content that focuses on making one single point means you actually put your ideas out there.

And that means people get exposure to you, your thinking, your vibe, and ultimately, move a step closer to working with you.

Perfectionism = fear.

Instead of aiming for perfection, do what you can consistently do and aim to make each attempt 1% better.

Like a muscle, you will improve your output AND you will get results instead of waiting for the mythical opportunity to produce high-quality content consistently.

The market doesn’t need perfection to buy from you. You need to figure out a way that works for you to keep showing up.

Watch my full, live-recorded, and imperfect video on this topic here: https://www.youtube.com/live/fHOjJEpZN58

Be sure to like and subscribe if you’re into that kind of thing!

—kevin

March 3, 2025

Earn more with services targeted at different customer segments

The longer I consult, the bigger my clients get on average. And with that, my revenue and profit has been increasing in lockstep.

I used to work with small businesses. And I still technically do!

But the small businesses I work with are getting bigger on average. And as a result, I can charge more and do more work in my wheelhouse.

My clients now are less price sensitive, do more advanced marketing, have more resources to leverage, and they see greater value as a result. It’s an ideal combination.

It’s gotten to the point where I could focus exclusively on multi-location coworking spaces—a tiny market compared to most—and would still have a thriving practice.

(In case you don’t know, I do marketing consulting for coworking spaces as my main gig).

Why do I tell you this?

Sometimes, the thing holding you back from earning more is the type of customer you’re working with.

You only have so much time, energy, and bandwidth to do client work. It might be as simple as continuing to move upmarket to more established businesses.

Or, you might benefit from working exclusively with better-funded businesses. Or some other proxy for higher earning potential.

So how do you begin to evolve to larger (or more profitable) market segments?

The best way I know how is by creating customer segment-based services.

Your services become less about levels of deliverables/access to you and more about the size and/or problems of your ideal buyer. 

For example, I have a service called the Empire Program for 4+ location operators, the Navigator Program for 1-3 location spaces, and the Ignite Program for pre-launch spaces.

The Empire Program has the highest price, as you’d expect. But the Ignite Program is more expensive than the Navigator Program even though the target business is pre-revenue.

Why? Because the client receives greater value (and there’s more work to be done since we are starting from scratch).

The value I create comes in the form of:

  • De-risking their business and marketing investments
  • Building things the right way the first time vs. redoing things later
  • Faster revenue growth leading to greater downstream profits
  • Saving time finding and vetting contractors
  • Thinking about every decision and reinventing the wheel

The list goes on!

If you find yourself working with very small businesses or startups, consider creating a separate service for scale-ups and/or larger established businesses.

Design individual services around the different types of buyers in your industry so you can be compensated for the greater value you’re creating.

The same core service aimed at two different audiences can command vastly different fees—and position yourself as a credible option for that segment.

Want to learn more?

I recommend checking out my recorded workshops:

  • How to Sell Custom Consulting Services
  • How to Productize Your Advisory Services

Both are included in my membership, now available for a single lifetime access investment of $500.

By joining, you’ll also unlock:

  • All my other trainings, templates, and resources
  • Access to a private Slack community
  • Ongoing updates with new resources added every month

Everything you need to thrive as a solo marketing professional is waiting for you.

See you inside.

—kevin

February 20, 2025

Explaining my evolution from agency owner to fractional CMO (via an old unpublished article)

I recently stumbled upon a draft blog post I wrote in late 2017 when I was changing my business model as a digital agency to being a fractional CMO/strategist.

It’s like finding an old diary where I could take a peek into my former thought process and how I was communicating my evolution as a business (even though it appears I never published this).

If you’re thinking about or trying to make the leap from freelancer to consultant/fractional CMO, I think you’ll find this old unpublished artifact to be of interest.

While I communicate the value proposition slightly differently today, I think the general ideas are still worth factoring in should you wish to make a similar change to your business model.

—k

February 18, 2025

From Freelancer to Marketing Stategist with Jordan Mogck (Ep. 210 – HTSA)

Going from being an independent freelancer to your clients’ “marketing guy/gal” (aka strategist or fractional head of marketing) can be a tough leap.

Jordan Mogck was wrestling with this very process just last year. But when I caught up with Jordan, I found out he successfully made the leap from freelancer to strategist and fractional head of marketing for his clients.

And not just that, he also found a niche that aligns with his interests and values: Amish farmers!

Super interesting story.

Needless to say, I needed to bring Jordan on so I could find out exactly how he made the leap so others in his position could follow his example.

In this episode, Jordan and I talk about his transition from freelancer to strategist, how he found his niche working with Amish farmers, and more.

  • Transitioning from freelancer to strategist (and the steps he took in between)
  • How he repositioned himself to sell more strategic offerings
  • Exploring alternative niches before stumbling into a new niche—Amish farmers!
  • How a “Golden Goose” relationship led to three clients (and counting)
  • The benefits of aligning your personal identity with the niche you serve
  • Using a performance-based compensation model with a fixed base and % of revenue
  • How Jordan manages scope and delivers his engagements
  • The benefits of a retainer-based model vs. only project work
  • How Jordan plans to find more clients when his target market isn’t online
  • Mindset shifts around mass vs. small audience marketing (resonance)

You can connect with Jordan on LinkedIn, check out his freelance website (new one forthcoming), or connect over on X.

Watch or listen to this episode:

  • YouTube
  • Podcast Player

Hope you enjoy this episode and if you do, please share with a friend!

—kevin

P.S. Jordan was able to make this transition with the help of his learnings in the How to Sell Advice membership. Consider joining here: https://howtoselladvice.com.

February 10, 2025

Two ingredients in a successful content strategy

I used to consider my day a success when I did two things:

  1. Wrote and sent an email to my list (like this one)
  2. Spent at least 30 minutes exercising

If I did those two things, everything else would work out.

And to some extent, I still feel that way!

Writing is one of the core ways I think through my ideas and build trust with potential clients. I also don’t know where I would be without exercise.

Somewhere along the line though, I decided I didn’t need to write daily. I wrote and published on this blog/email list daily for two years and, frankly, it became a grind.

I’m still glad I went through that process. It helped me learn what people wanted and clarified my thinking on many topics. It also helped me attract over 100 paying students on this side of my business.

For my consulting practice, I did a similar thing when I was just getting started. I wrote daily for a while and it helped me build my initial traction and get people’s attention.

The problem with this mindset

The problem with trying to write daily, at least for me, was that I focused mostly on nurturing and converting my subscribers and spent very little time building awareness for myself.

I half-assumed that being prolific would, in itself, get people to discover me and subscribe to my mailing list where they could be swooned into buying something.

But the truth is, I needed to spend much more time building top-of-funnel (awareness) and driving people to my mailing list so they could be “nurtured” into buying.

My current approach

For my consulting practice, I rarely create “content” anymore. I speak on stage, get featured by other industry publications, attend conferences, guest on podcasts, and lightly maintain key relationships on LinkedIn and other places.

With that business, I only need seven clients to be completely booked solid. My retention rate is high (years), so these few practices keep me more than busy enough.

With my education business, however, I need to sell to a lot more people to build a meaningful income. My conversion rate from my small audience is high by most standards, but without a big audience, it’s hard to keep growing.

That’s why I started publishing on YouTube. My small channel is already producing a clear ROI. I don’t feel like I need to post on Twitter anymore to be successful (I somewhat gave up on it as a platform though I check it daily).

YouTube is a wonderful place to reach your ideal audience. It’s less ephemeral than most other platforms and seeing you on video often creates a much stronger sense of intimacy than simply reading text on a page.

Your takeaway from all of this? 

The key, as usual, is to know your goals.

If you need to kick-start in a new niche and you want to prove (to yourself and the market) that you have things to say, publishing daily can be a way to create a “purple cow” effect where people notice you because you publish daily. There are other ways you can do that, too. This is just one way.

The key mindset is to create a strategy that builds your top-of-funnel AND provides an incentive for people to join your list, which is where you can nurture your audience to drive sales. 

If you then mix that with a little biz dev activity, and crucially, use strong positioning, you don’t need much else to be successful… assuming you are good at what you do of course.

I’m off now to create some YouTube videos, see you in the next one!

—kevin

January 24, 2025

How to stay relevant in the age of AI

I started building websites in the late 1990s/early 2000s.

Geocities and other site builders made it easy to have dazzling gif-centric websites that would make your eyes bleed (in the best possible way).

By about 2004, I started hand-coding websites in HTML/on-page CSS. I had a website for my teenage rock band with a thriving little forum, and by some miracle, another site on internet security that had 20k visitors a month (don’t ask me how!).

By 2006, I realized these skills were something people would pay for, so I started a little “web and graphic design” company so I could officially demand money from friends and family who were asking me for free work.

It didn’t even dawn on me until 2012 that this could be an actual career. I was doing freelance work for companies I worked for (building their sites, designing signs/logos/menus, etc.). In 2013, I landed a corporate job in corporate for a major law firm.

In 2015, I went full-time on my own with a web design and digital marketing agency.

The rest is history.

So why do I tell you this story?

The reason I have stayed in business and, frankly, have never had issues finding work is that I was able to navigate and implement technical skills for businesses. 

I didn’t think of it as marketing until much later, but all along I had the advantage of technical skills using tools like Photoshop (illegal copies I’m sure) and HTML/web development.

Why do technical skills matter so much?

For one, they allow you to execute. But more importantly, they are rarer than other skills.

Being technical is a rare enough skill set and in high enough demand to command a premium over less technical skills (exceptions given to strong creative expertise).

Other agencies would outsource the technical stuff to me (like web dev, SEO, ads, analytics, hosting, etc.) and would do the creative stuff themselves.

In many cases, I earned more by being technical.

AI is changing things

AI is going to make a lot of technical skills redundant. We’re entering a world where the long tail of execution will be absorbed by AI and robots. You won’t need to learn code or server infrastructure.

So what does one need to do to stay relevant as AI slowly takes over our work responsibilities?

For now, the best thing you can do as a marketer is to:

  1. Become a strategist who is very good at deploying tactics to get business results, and
  2. Learn AI to stay on the cutting edge of the field so you can stay relevant for as long as possible

In other words, marketing teams will be much smaller and led by strategists who can navigate technology, creativity, and strategy.

At least for now. Who knows what things will be like in 5-10 years but to me, the writing is on the wall for those who are unprepared.

Being good at AI is the new “technical skills”

If you have the technical chops to implement (eg. design, develop, write, etc.) you have a chance of being able to deploy AI effectively to create similar results to the old manual way you did things.

If you don’t already have these skills, using AI will be much harder (for now).

Being a skilled craftsperson allows you to make more precise prompts and get more precise outcomes. You probably have better taste, too. Those skills are not wasted.

But the hands-on-keyboard stuff is going to go away… and fast.

It’s best to stay on the technical side of the equation by getting very good at AI. Because it’s not AI that will take your job, it’s someone who knows AI that will take your job. 

You will still need the strategic skills to navigate the competitive nature of business, but I don’t think you will survive without also being on the AI/technical side.

Be the one who is still standing when the commodified work gets taken by the robots.

—Kevin

January 13, 2025

Freelancer → Fractional CMO → Advisor → Teacher [DMAT Framework]

There are fundamentally 4 ways you can sell your expertise as an independent marketing professional:

  1. Doing (Freelancing/Execution)
  2. Managing ( Fractional CMO)
  3. Advising (Consulting/Coaching/Mentoring/Advising)
  4. Teaching (Knowledge Products, Speaking, Training)

In this video, I explain how to take the very first step towards selling your expertise—not just your hands.

I also go into the journey from doing into doing more strategic and higher levels of engagement that leverage your expertise without scaling an agency.

If you’re looking to earn more, stay small, and do less grunt work, this is the video that underpins a lot of my teachings and will give you a roadmap for growth.

Watch the video (and subscribe to my channel) → 

—kevin

December 9, 2024

Run your marketing program

When I’m in the car, I like to listen to the radio.

(I know, I’m old school like that).

There are two or three stations I like to tune into. Mostly rock but occasionally I’ll venture into the pop or even jazz channels.

The point is, I can predictably turn the radio dial (press the button) and get to the types of music I enjoy.

That’s because radio stations are always on. They keep showing up. They have a genre. Most importantly, they run a program.

And that’s how I like to think about marketing also.

Good marketing is like an always-on radio station. People learn to expect what you’re about. They tune in when they can, and tune out when they’re busy, but you’re always showing up regardless. And people learn to expect that.

Imagine radio stations only periodically ran “campaigns” of music and banter whenever they wanted to sell ads. You’d never have their station tuned to your favourites, which means they wouldn’t even exist in your mind.

It’s the same with marketing—particularly when you’re trying to sell your services and expertise.

Rather than thinking in fits and starts—doing big pushes between long downtime—try to keep the music flowing.

Even if it’s small pieces published regularly, being consistent with it over time is part of the magic that gets people to buy from you.

People learn to tune into your station when they have the time. You’re on their favourites list (eg. email list or social following).

Campaigns have a place, but good marketing is less about campaigns and more about maintaining a program.

What’s your program?

—kevin

November 22, 2024

Why you don’t need LinkedIn to get clients

I’m able to be continually booked solid with consulting clients without doing the LinkedIn song and dance.

It’s true, the gurus will tell you to be there. To publish daily. To engage, comment, like, share, and support people there.

And while LinkedIn is definitely the place to be if you want to show up for B2B clients, it’s not necessary if you have other ways to achieve the same end.

In my latest YouTube video, I explain what I focus on and how I get clients consistently—without using LinkedIn very much.

Tune in and let me know in the comments what you think.

—k

P.S. Be sure to like/subscribe to the channel as well!

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