The Pretty Smart Podcast

A sailcloth tent, a mechanical bull, fireworks, and a whole lot of rain.

In Episode 12 of Pretty Smart Podcast, Dana Ashley and Bailey Pianalto recap an unforgettable Kansas wedding they worked on together—Dana as the planner and designer, and Bailey as the photographer and media team lead.

Set on the couple's private property, this "East Coast meets Midwest" celebration blended elevated wedding design with an upscale honky-tonk atmosphere. From live music and fireworks to open-air cooking and a mechanical bull, every detail was designed around creating an incredible guest experience.

But Mother Nature had other plans.

After storms rolled through the night before and continued into the wedding day, the team arrived to find standing water beneath the tent. Dana and Bailey share the behind-the-scenes challenges, the work that went into pulling everything together, and how their vendor team adapted to bring the celebration to life.

It's a look at what really goes into producing an elaborate outdoor wedding—and why having the right team makes all the difference.

Topics include:

• Luxury tent weddings

• Private-property wedding planning

• Rain and weather contingency plans

• Wedding design and production

• Vendor teamwork

• Guest experience

• Wedding entertainment

• Behind-the-scenes wedding stories

You built the business. Now, how do you build the team that helps it grow?

In Episode 11 of Pretty Smart Podcast, Dana Ashley and Bailey Pianalto share their experiences growing their teams and learning how to go from doing everything themselves to hiring, delegating, and managing other people.

They discuss how to know when you're ready to hire, what they look for in assistants and team members, and why skills aren't the only thing that matters when you're trusting someone to represent your business.

They also get into the growing pains that come with becoming a leader: training your team, setting expectations, delegating effectively, maintaining your standards, and learning to let go of some control as your business grows.

Topics include:
• Hiring your first employee or assistant
• Scaling a small business
• Building a strong team
• Delegating
• Training and onboarding
• Managing employees
• Leadership
• Growing a creative business

Some weddings are beautiful. Some are iconic. And some actually change weddings forever.

In Episode 10 of Pretty Smart Podcast, Dana Ashley and Bailey Pianalto dive into the real and fictional weddings that became pop culture moments—and left their mark on the wedding industry.

From Princess Diana and the Royal Wedding to Twilight, Crazy Rich Asians, Father of the Bride, and more, Dana and Bailey analyze the fashion, photography, design, traditions, and unforgettable moments that made these weddings so influential.

They're looking at it all through the eyes of a wedding planner and photographer—with plenty of opinions, nostalgia, and gossip along the way.

Which weddings still hold up? Which influenced real-life wedding trends? And which iconic moments deserve a little side-eye?

Topics include:
• Iconic pop culture weddings
• Royal and celebrity weddings
• Movie weddings
• Wedding fashion and design
• Famous wedding dresses
• Wedding trends
• Movies and wedding inspiration
• Pop culture nostalgia

You can be incredible at what you do—but if the right people can't find you, it doesn't matter.

In Episode 9 of Pretty Smart Podcast, Dana Ashley and Bailey Pianalto talk lead generation and the work that goes into consistently getting your business in front of potential clients.

They discuss how finding customers looks different when you're a brand-new business versus an established one, why understanding your ideal client should shape your marketing strategy, and how today's businesses can balance traditional lead sources with the constantly changing world of social media.

Plus, are wedding shows still worth the investment? Dana and Bailey share their perspectives on shows, referrals, social media, and the different ways wedding professionals can build a healthy pipeline of potential clients.

Topics include:
• Lead generation
• Finding your ideal client
• Small business marketing
• Social media marketing
• Wedding shows
• Referrals
• Marketing a new business
• Building a sustainable client pipeline

What does it really mean to be a "preferred vendor" in the wedding industry?

In Episode 8 of Pretty Smart Podcast, Dana Bacaling and Bailey Pianalto dive into the controversial world of pay-to-play: kickbacks, referral fees, paid preferred vendor lists, and other arrangements that can influence how wedding professionals are recommended.

They discuss how pay-to-play works from both the venue and vendor perspective, how these practices can affect wedding businesses, and what professionals should consider before participating.

Dana and Bailey also explain why not every preferred vendor relationship is created equal—and why there's an important difference between paying for a recommendation and earning one through experience, trust, and great work.

Topics include:
• Pay-to-play in the wedding industry
• Preferred vendor lists
• Kickbacks and referral fees
• Wedding venue relationships
• Vendor recommendations
• Business ethics
• Transparency
• Wedding industry networking

When your personality, face and personal story are closely tied to your business, where do you draw the line?

In Episode 7 of Pretty Smart Podcast, Dana Ashley and Bailey Pianalto discuss how entrepreneurs can build an authentic personal brand while maintaining privacy and professionalism.

they share how they decide what to include in their business content, what they prefer to keep personal, and how to connect with an audience without feeling obligated to share every part o their lives.

Dana and Bailey also reflect on their own branding strategies, previous rebranding experiences, and the process of developing a clear business identity when you are the face of the company.

Topics include:

- Personal Branding

- Business and Personal Boundaries

- Authenticity on social media

- Brand Strategy

Planning a wedding isn't about finding one amazing vendor - it's about building an amazing team.

Inspired but the excitement surrounding the World Cup, Dana Ashley and Bailey Pianalto explore why weddings truly are a team sport. They discuss how planners, photographers, venue, florists, DJs, caterers and other vendors work together to create a seamless wedding day, and why choosing professionals who communicate well can make all the difference.

Along the way, they share real wedding stories, common vendor red flags, and practical advice to help couples assemble a team they can trust.

Topics Include:

- Choosing wedding vendors

- Wedding planning tips

- Vendor collaboration

- Wedding-day communication

- Wedding red flags

- Real wedding stories

Every wedding professional has a few opinions they're unwilling to budge on.

In Episode 5 of Pretty Smart Podcast, Dana Ashley and Bailey Pianalto share the wedding-industry hills they're willing to die on and explain why these details matter more than many couples realize.

From lighting and linens to vendor selection, guest experience, photography priorities and wedding cake, they discuss the decisions they believe have the biggest impact on a successful wedding day.

Whether you agree with them or not, this episode is full of candid opinions, practical advice and a few entertaining debates.

Topics include:

- Wedding Planning Advice

- Wedding Photography Tips

- Guest Experience

- Wedding Hot Takes

What makes a brand memorable?

In Episode 4 of Pretty Smart Podcast, Dana Ashley and Bailey Pianalto discuss the difference between you and your brand, how entrepreneurs can develop an authentic voice, and why chasing trends isn't always the best strategy.

They explore the relationship between personal identity and business identity, the importance of consistency, and how brands naturally develop over time as businesses grow.

Whether you're a wedding professional, creative entrepreneur, or small business owner, this episode offers practical insights for building a brand that reflects who you are while attracting the clients you want to serve.

Topics included:

-Brand Strategy

-Marketing Fundamentals

-Personal vs. Business Branding

-Finding your voice

-Brand Evolution

-Standing out from competitors

How much should you spend on a wedding? And more importantly, where should that money actually go?

In Episode 3 of Pretty Smart Podcast, Dana Ashley and Bailey Pianalto discuss most common budget mistakes they see couples make during the wedding planning process.

From booking a venue before understanding the full financial picture to unexpected expenses and emotional spending decisions, they share practical advice to help couples create a budget that aligns with their priorities.

They also reveal the single biggest factor that impacts wedding costs and explain how thoughtful planning can help couples get more from their investment.

Topics include:

- Wedding budgeting

- Hidden Wedding Expenses

- Venue Selection

- Wedding Dress Shopping

- Budget Priorities

-Wedding Spending Tips