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about Carolyn

Meet your
tech-decoding Squarespace web designer for brands with personality.

Carolyn Leasure, website designer for small businesses, stands in front of a row of trees smiling at the camera while thinking about all of the brands with personality she is going to help launch

Finding a Squarespace web designer who can build you a strategic site, craft authentic messaging, streamline your tech - & actually get you - feels nearly impossible.

We’ve found each other!

a black and white photo of Carolyn Leasure, a white woman, seated and holding a Ruth Bader Ginsburg mug, discussing design strategies, highlighting her focus on brands with personality in Squarespace website development

I’m a Squarespace web designer for small businesses who believes in people over pixels.

The vibrant hummingbird from the SmallBiz Sidekick logo, a beacon of innovative and tailored website design solutions for the bustling entrepreneur

Some designers & developers just hand you a pretty website and wave goodbye. But your business needs someone who gets that true growth happens when strategic design meets seamless systems.

That's why I focus on creating websites where all the pieces click – from first looks to micro automations that help free up your time and energy.

What sets my approach apart:

  • I work with just 1-2 clients at a time, because your success deserves my full attention.

  • You get someone to guide you through the entire process, from strategy to launch and beyond.

  • Together we'll create an online home that gives you that solid foundation you've been looking for and easy tech solutions that you can rely on.

The end result? Consistent growth of right-fit clients and a life-first business that actually gives you room to breathe.

Headshot of Sally Hayes of Women in Self Healing in Los Angeles California

“No matter who you’re hiring, they have to understand your business and your vision. Carolyn gave me a lot of homework, but once we were done she understood exactly what I wanted - and even I was surprised at the direction the process took me.

For a long time, I didn’t think what I do could be translated online. I didn’t think you could look at a website and get the feel - and you helped me do it. I’m obsessed.”

Sally Hayes // Women in Self Healing

What I care about

Running a solopreneur business means I get to put my “why” into everything I do, and let go of the bullsh*t.

Here’s a sneak peak into what drives the work:

Carolyn Leasure of Maypop Creative Studio, smiling, seated and talking with her hands. She demonstrates her expertise as a website designer and Squarespace conversion specialist, ready to enhance the online presence of small businesses

Connection

In an age where everyone (and their AI) is fighting to be heard, real connection matters more than ever.

You know it, and I know it: the most magnetic brands are the ones brave enough to be unapologetically themselves. By fostering authentic connection, your business doesn't just communicate. It builds lasting bonds based on trust with your right-fit clients.

That's why every project starts with getting to know the real you, your vision and your goals. I create space for genuine interaction and mutual understanding. Both because that's just how I roll – and because it gets better results.

When we drop the pretense and get real? That's when the true connection – and magic – happens.

Purposeful Passion

Every moment spent doing what fulfills us is a chance to create something meaningful. For me, this means:

  • getting stupidly excited about color palettes, copy and code,

  • finding joy in both the triumphs and the messy parts,

  • and spreading that spark of 'hell yes' energy wherever I go.

Look, life is too short (and often too hard) to spend it going through the motions. When we embrace what lights us up, that passion becomes a sort of wild, contagious magic.

Because if we're not finding moments of genuine joy along the way – maybe in the chaos, too – are we even doing it right?

Growth

Growth is at the heart of my approach – both personally and in my work. It's about embracing adaptability and resilience: 'Rugged Flexibility.'

It's about having the strength to hold onto what matters while being brave enough to evolve. Sometimes that means taking bold risks, other times it's navigating unexpected challenges.

But it always means staying curious, staying open, and finding opportunity in change. Because here's the truth: Plan A was just a rough draft (and spoiler alert: so is Plan B).

The magic happens in finding that sweet spot between standing strong and staying flexible.

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How that shows up in our work together

Featured
No false promises, no forced signups, no fake countdown timers.

When you work with me, we won’t use any pressured marketing tactics.

Your clients will connect with the real you and what you offer.

If we speak to your potential clients in a way that feels legit, you naturally connect with those who are the best fit! (No rhyme intended, but hey, let’s have some fun).

You get to focus on your zone of genius

What got you into your business and career is your purposeful passion. Keep doing that and it will magnetically attract your right-fit clients.

Leave the things that you can do (but don’t like) or the things that are super-challenging to the experts.

And I’ll do the same!

Offer meaningful value (yes, sometimes for free!)

Did you know that most people need 5-7 touches with a business before they’re ready to get on board?

Let’s find ways to keep people in your ecosystem so they can see the value in your offers and just how damn good you are at what you do.

Then they’ll purchase when they are ready – rather than get pressured into a sale when they’re not.

Anti-hustle culture

My inbox is always open, but I’ll only respond during working hours (and I hope you will too!).

Hustle culture can lead to burnout, illness, and disconnection. True connection and purposeful passion creates balance and growth.

For me, this means:

  • Treating others with respect and empathy.

  • Spending time with family.

  • Meditating every day (and by “every day” I mean when I drag my bottom to do it, and then remember how good it is).

  • Getting outside as often as possible.

  • Being able to take on a pro bono project annually.

  • Showing up as my true self (hello, awkward) both in person and online.


Ultimately, being balanced between my online life and still deepening my offline world with friends, family and community.

Growth from knowledge

I make decisions based on gathering as much information as possible.

We determine strategy based on analytics, your goals, and what works for you in your day-to-day.

I don’t skip the first steps – no matter how challenging – for quick fixes that don’t allow for growth in the long term.

Instead, I make them as simple as possible and guide you through the process.

Always learning, always growing

The one truly limited resource we have is time.

I use design and tech innovation to gain the highest ROI in connecting with your ideal audience.

Because who has time to spend spinning wheels trying to just keep up with trends and shouting into the void?

Consistently innovating means consistently finding new ways to engage with potential clients.

And while some marketing bros are thinking about today’s one sale, working with me means creating long-term relationships with your audience. This builds a solid client base that will come back to you time and time again.

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A few of my major achievements

One time I made it in and out of Ikea in less than an hour and spent less than $100.

I had a mini burlesque career from age 29-32.

(Sign up for my emails & get the full story)

Carolyn Leasure of SmallBiz Sidekick laughing with a client, showcasing the friendly and collaborative approach in Squarespace website design for small businesses, emphasizing personalized client relationships

I also had a short-lived one-season rollerderby run that ended with a concussion.

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My first word was cheese (and I opened an artisanal cheese shop & wine bar in 2012).

I can drive stick shift.

A black and white photo of Carolyn Leasure of SmallBiz Sidekick, based in Charlottesville, Virginia, smiling in a polka dot dress, exemplifying professional Squarespace website design expertise, dedicated to empowering small businesses
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js-hero-timeline My JOURNEY to Maypop Creative Studio

  • Born a strategist in Buffalo, NY

    Entrepreneurship & strategy have always been my calling.

    Starting at age 5, selling painted pet rocks with my big sister on the side of the road.

    And even during my off-hours these days, at my tactics-fueled board game nights with family & friends.

    Carolyn Leasure of Maypop Creative Studio, as a 5 year old, sitting under an umbrella in the yard with her sister

  • Hustling for Cheddar in Washington DC

    I spent my late 20’s and 30’s establishing a national reputation as a fromager/wine wiz and building my brick-and-mortar artisanal cheese shop & wine bar in Washington DC.

    I had no idea what I was doing – but it was a wild ride.

    I was working 7 days a week, growing my business every year, doing everything myself. And everything was absolutely fab.

    Or so it seemed.

    3 polaroid images of Carolyn Leasure starting and running her first business, Righteous Cheese, a cheese shop and wine bar in Washington DC

  • Successful but overwhelmed

    Then in 2018, I popped my head up to realize I was barely keeping above the quicksand.

    Solopreneur life with a staff of 9, managing manual systems, worsening chronic health issues, and figuring out how to be a new mom?

    I was no longer doing the work that I loved – my purposeful passion.

    Two polaroid images of the burnout days of Carolyn Leasure's first career, which prepared her to help other solopreneurs and small business owners with streamlining systems

  • A life-first business change

    So we moved to the beautiful, chilled-out mountain town of Charlottesville, Virginia. Now I gaze out on the mountains over my morning pour-over coffee. And can float down the Rivanna River on an inner tube with my family on the weekends if we want.

    Ironically, I leaned hard into some of my biggest stressors and I started helping solopreneur friends of mine that were struggling.

    I put my creative writing degree to use and started copywriting.

    I learned coding, brand strategy, email marketing best practices, Squarespace web design, user experience, and SEO techniques to become an expert and help other burned-out small business owners.

    3 polaroid images of Carolyn Leasure's life in Charlottesville Virginia: drinking coffee next to the mountains, river rafting, and hiking

  • Maypop Creative Studio: growth, connection, and purposeful passion

    In 2019, I started my design studio and became obsessed with helping service providers and coaches nix that same feeling of overwhelm that comes with small business DIY design platforms and manual systems.

    At Maypop Creative Studio, I apply the combo superpowers of brand & web design, copywriting, systems, and interactive lead generation at once.

    This magnetically attracts right-fit clients to your biz and creates long-term relationships with them - all in ways that let you breathe easier instead of getting wound tighter.

    Carolyn Leasure of Maypop Creative Studio, sitting at a cafe table, meeting with a client to craft small business strategy
Another stylish divider, because who says you can't mix business with pleasure? Certainly not us at SmallBiz Sidekick, where we blend functionality with flair.

Will we be a good fit?

Will I be the right Squarespace web designer and strategist for you? I hope so.

I love working with solopreneurs, small business service providers, coaches, and health & wellness professionals that are aligned with what I offer. If not, I’m happy to make a recommendation for someone else.

Take a look and see if I’m the right choice for you:

  • Caucasian wellness entrepreneur client of Maypop Creative Studio, viewed from the back. Working from home, on the couch, with a small potted tree in from of her, she exemplifies the successful implementation of Squarespace website solutions

    • You are excited and passionate about your project.

    • You are interested in building in the platforms I build in (check the FAQ).

    • You are ready to delve into what it takes to show up as your authentic brand – rather than what you think it should be.

    • You want to build long-term relationships with clients rather than ones built on pressure.

    • You are willing to spend time gathering all of your details and have your content ready to go 1 week before your start date.

    • You are systems- and process-oriented. You can make the commitment to keep the project moving and meet deadlines.

    • You understand this is a business investment that will lead to long-term growth for your brand.

    • You are ready to trust a professional with design, rather than try to dictate each element.

    Let's do this!
  • A potted plant in front of a round mirror on a wooden dresser, symbolizing the organic approach of SmallBiz Sidekick in Squarespace website design for small businesses, reflecting a commitment to nurturing and sustainable web solutions

    • You are not sure where you want your business to go or what content you need to start.

    • You don’t have a sound starting knowledge of your ideal audience or your brand identity.

    • You don't find value in brand or marketing strategy, or why it is a key starting point.

    • You prefer a pressured marketing technique rather than building long-term trust with clients.

    • You are not open to new design ideas and layouts, particularly that prioritize functionality and accessibility.

    • You prefer to dictate every design detail.

    • You want a website on Wix, Wordpress, Webflow, Kajabi, or Showit.

    • Process and systems are a waste of time - only the end result matters.

    No judgement here, it just means we might not be the ideal fit.

How I’ve helped other
small businesses LIKE YOURS

Strategy • Sprints • Custom

Check out the case studies
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Kind Words

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Kind Words ···

Carolyn had my back, & understood the nature of my business and where I wanted to go with it. Carolyn is a partner.

— Neil Runyon / Carnegie Hill Massage

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