Outsmart the Hustle

In this episode of Outsmart the Hustle, we take real look at a tough business decision—choosing to quit something that took hard to build. We talk about canceling the Refresh conference, closing the Booked by Strategy business, and the lessons that came from realizing it just wasn’t the right time. It’s an honest conversation about learning that sometimes the smartest move in business is letting something go so you can focus on what actually moves the needle. 

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Being booked doesn’t always mean being profitable. In this episode of Outsmart the Hustle, we break down how creatives can understand their margins, price their packages intentionally, and focus on profit—not just revenue. We discuss the importance of structuring your services, accounting for real expenses, and building a sustainable business that actually pays you back.

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In this episode of Outsmart the Hustle, we talk about imposter syndrome and the fear that comes with starting something bigger than you. I share a behind-the-scenes look at transitioning my video business into a creative marketing agency, the insecurity that came with it, and the mindset shift that helped me keep moving forward.

If you’re a creative entrepreneur navigating change or are in a season of transition, this episode is a reminder that growth doesn’t require perfection—just the courage to start.

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Running ads in Q1 can feel unpredictable. In this episode, we walk through the most common issues wedding pros run into this time of year, from attracting the wrong leads to booked calls not showing up or not closing. I’ll break down what’s usually causing the problem and what to tweak in your ads, DMs, pre-call sequences, and sales process so you can fix those bottlenecks and get better results.

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Weddings built your business, but they don’t have to carry it forever.

This show is for wedding pros who love what they do but know there’s more on the table than trading Saturdays for dollars.

We’re talking to photographers, videographers, planners, florists, and creatives who figured out how to make money beyond booking another wedding.

Just an honest conversation about leverage, longevity, and building a business that works for you even when you’re not shooting a wedding.

That’s the question I'm exploring in this episode. 🎙️

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Building the Business Your Future Self Can Sustain

What if making more money doesn’t automatically mean you’re winning?

This year, our business hit its highest revenue ever, and we still weren’t profitable. In this episode, I’m pulling back the curtain on what that actually means, why it’s not a failure, and how growth seasons often come with a lag before the payoff.

We’re talking about the real cost of hiring and onboarding employees, why profit can dip during expansion, and how to think long-term instead of panicking when the numbers don’t immediately reward your effort.

This episode is for the business owner who feels like they’re doing everything right but still feels stretched, confused, or unsure how to prepare for what’s next.

Inside this episode:

• The difference between a building season and an optimizing season
• Why more revenue doesn’t always equal a healthier business
• How hiring and onboarding impact short-term profit
• What it means to let investments mature instead of pulling the plug too early
• Why consulting a CPA is part of sustainable leadership, not a last resort
• How to plan for profitability while sustaining employees and contractors
• Questions to ask yourself as you prepare financially for 2026

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• Booked by Strategy Course
• Workshop Details
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• LinkedIn

If you’ve ever felt like systems are suffocating or “too corporate,” this episode is about to flip that belief on its head. I sat down with Wendy Kidd, founder of Boss Level Engaged and The Nonprofit Nook, to talk about how intentional systems can actually become the thing that frees you, supports your team, and strengthens your client experience.

Wendy has built her entire career around helping business owners and nonprofits stop running in circles and start operating with clarity. In this conversation, she shares how her love for time management evolved into a full-blown passion for creating systems that actually work in real life, not just on paper. Her process is thoughtful, human-centered, and rooted in helping people feel empowered instead of overwhelmed.

We get into:

•  How Wendy became the systems-focused leader she is today
•  Why Boss Level Engaged launched from people constantly wanting to “pick her brain”
•  The red flags that your systems are holding you back
•  Why nonprofits face many of the same pain points as small businesses
•  What Wendy’s full systems overhaul process looks like, from discovery to documentation
•  The core systems she evaluates across sales, client experience, service delivery, and internal ops
•  How strong systems reduce stress, energize your team, and elevate client trust
•  The mindset shift that helps owners stop resisting structure and start embracing it

Whether you’re a creative entrepreneur, a nonprofit leader, or someone who’s tired of putting out fires all day, Wendy brings the clarity you need to build a business rhythm that feels calmer, cleaner, and more intentional.

Links & Resources:

Connect with Wendy Kidd:

• Boss Level Engaged
• The Nonprofit Nook
• Instagram

Connect with Hannah McGinty:

• Booked by Strategy
• Workshop Details
• YouTube
• Instagram
• LinkedIn

P.S. Send this episode to a friend who’s ready to stop operating in chaos and finally build the systems that will carry them to their next level.

#CreativeEntrepreneur #BookedByStrategy #OutsmartTheHustle #SystemsStrategy #NonprofitLeadership #WeddingProLife #Entrepreneurship #BusinessGrowth #PodcastEpisode

Today’s episode is a little behind-the-scenes moment about the Booked by Strategy Workshop. I’m sharing why the dates shifted, why the styled shoot is no longer part of the experience, and how these changes actually make the event stronger for the creatives attending. If you’ve been eyeing the workshop or you’re already locked in, this convo will help you understand the heart behind the pivot and what’s coming next. Let’s get into it.

Connect with Hannah McGinty:

• Booked by Strategy
• Workshop Details
• YouTube
• Instagram
• LinkedIn

When people you respect tell you to quit your business dreams, what do you do?

Short answer: you keep going.

But not blindly! Definitely in discernment and discipline.

In this episode, I'm breaking down what to do in seasons of pressure, when the path gets foggy, and when even wise voices question your vision. Because sometimes the resistance is a sign to pivot, and sometimes it’s simply proof that you’re early.

Ask yourself:

• Am I building from fear or from faith in the vision God already showed me?
• Is this resistance trying to protect me or grow me?
• Am I chasing comfort or calling?
• What evidence in my story already proves I can do hard things?
• What does future-me thank me for choosing today?

If you're in a season where you feel stretched, misunderstood, or tempted to shrink, this episode is your reminder: pressure isn’t a stop sign. It’s the gym where your future leadership muscle is built. Exercise amidst the pressure!

This is your chance to level up your capacity, and the good news is you're not in this alone because every entrepreneur feels this pressure at some point, or many points.

Stay rooted in your God-given purpose. Stay in the room long enough to see the harvest. Winter is merciless. The life of spring is right around the corner.

Ever wondered what it really takes to build a thriving creative business that lasts? On this episode of Outsmart the Hustle, I sit down with Jai Long, creative business coach, award-winning photographer, and host of the Make Your Break podcast, to talk about what we’ve both learned from saying yes in the face of challenges. 

This conversation is all about how the moments of risk, uncertainty, and adversity can actually become the turning points in your business. Together we share the lessons we’ve picked up along the way and why leaning into opportunity matters more than waiting for the “perfect time.” We dive into: 

• Why opportunity cost matters more than price when investing in yourself
• How community and collaboration can change the trajectory of your career
• The mindset shifts that separate thriving creatives from stuck ones
• Why experiences like workshops can’t be measured in dollars alone
• What saying yes, even when it feels hard, can teach us about growth

Whether you’re a creative entrepreneur, a wedding pro, or someone who’s ready to stop holding back, this episode will give you the perspective and encouragement to take your next big leap.
 
Links & Resources:
 
Connect with Jai Long:

• Website: jailong.co
• Instagram: @jailong.co
• Podcast: Make Your Break

Connect with Hannah McGinty:

• Booked by Strategy
• Workshop Details
• YouTube
• Instagram
• LinkedIn

P.S. Share this episode with a friend who needs encouragement to say yes to their next big opportunity.

#CreativeEntrepreneur #BookedByStrategy #OutsmartTheHustle #PodcastEpisode #JaiLong #MakeYourBreak #WeddingProLife #Entrepreneurship #Workshop #WeddingBusinessWorkshop #WeddingWorkshop