Founder-led. Operator-built.

Built by founders, for founders.

We have built businesses from the inside, not advised them from the sidelines. Pretty Creative combines creative vision with more than 25 years of hands-on ownership and operating experience.

Jenn Dieas and Shane Schwartz seated against weathered brick, each holding one of their dogs

25+ years owning, operating, building, and growing businesses.

We understand the realities behind the brand — revenue · payroll · staffing · pricing · sales · customer experience · operations · expansion · slow seasons · growth pressure · owner decision-making.

The operating story

Strategy shaped by real ownership experience.

We’ve watched founders get burned by agencies that delivered something pretty and called it done. That’s not how we work — every recommendation here is tested against a business we’ve actually run.

Not a résumé — the rooms we have actually stood in.

Jenn smiling while Shane installs shelving behind her, drill in hand

Build weekend — Shane on the counter, shelving going up.

Businesses founded and operated

Nineteen years building and running Glowout in Chicago — hiring, pricing, payroll, slow seasons, expansion decisions, and all — alongside Pretty Creative and its hospitality and community ventures.

Experiences launched and hosted

Retreats, workshops, founder dinners, and community programs designed, priced, staffed, and hosted end to end — not planned on paper and handed off.

Teams managed

Customer-facing teams hired, trained, scheduled, and led through busy seasons and quiet ones, in businesses where the schedule has to work every single day.

Offers and systems created

Service menus, memberships, retail programs, booking systems, CRMs, automations, and the AI-powered operations that keep modern businesses answerable around the clock.

Industries served

Beauty, wellness, hospitality, real estate, home services, healthcare, education, and community — customer-facing businesses where experience is the product.

What ownership taught us

Beautiful is only the beginning.

We’ve spent years building, growing and operating businesses of our own. We understand what it takes to turn a strong idea into something people choose, remember and return to.

A brand is more than what people see. It’s how clearly you communicate, how thoughtfully you operate and how someone feels at every point of contact.

Pretty gets their attention. The experience brings them back.

The strongest brands are felt in the details.
Good strategy makes a business easier to understand—and easier to choose.
Your customer’s experience begins long before they walk through the door.
Creative should support the business, not create more work for it.
The goal isn’t simply to look established. It’s to become unforgettable.

The best creative work doesn’t sit separately from the business. It strengthens the experience, supports the team and makes growth feel more intentional.

Because getting someone’s attention is one thing.
Building something worth coming back to is another.

The people behind it

Jenn Dieas

Founder · brand · hospitality · community

Jenn brings 25+ years of experience across entrepreneurship, brand development, luxury retail and hospitality — including work with Saks Fifth Avenue, Marriott and Loews Hotels. She built her own small business from the ground up for the last 19 years in downtown Chicago — one of the country’s most competitive markets.

As a Goldman Sachs 10,000 Small Businesses alumna and an Airbnb traveler with 78 stays since 2015, she understands what it takes to create desire, earn trust, deliver an exceptional guest experience and build a brand with staying power.

Featured in

Allure · Seventeen · Fox · CBS · NBC · WGN · TLC · Tiny Home Tours & more

@jenndieas_

Shane Schwartz

Systems · AI · operations · implementation

Shane builds the infrastructure that helps businesses run better and grow with more control.

After years operating a family-owned service business, he learned firsthand what strong systems need to do in the real world. He has since studied, tested, and implemented booking systems, CRM architecture, automations, workflows, and AI tools across a range of businesses.

His strength is turning complex technology into practical infrastructure teams can actually use.

He doesn’t build for the demo.
He builds for the busy Saturday.

Why it matters

Founder perspective. Operator discipline. Creative vision.

When we recommend a positioning, an offer, a website, or a system, it is because we have run businesses that depended on decisions like that. We know the difference between a beautiful idea and a business that performs — and we build for the second one, beautifully.

The invitation

If the work matters, the relationship does too.

Start a conversation