Are in-person retreats really worth the time, effort, and investment? (Spoiler: yes—when done right.)

If you’ve been wondering whether to host a retreat, workshop, or live event as a way to grow your brand and serve your clients in a deeper, more meaningful way—this episode is your permission slip to seriously consider it.

I’m walking you through why in-person experiences are making a major comeback—and what that means for online entrepreneurs like us.

From my own experience hosting immersive events (hello, Machu Picchu and Stonehenge!) to the latest data from hospitality giants like Hilton, I’m pulling back the curtain on how smart, well-planned retreats can skyrocket connection, conversion, and long-term revenue.

You’ll walk away from this episode with the tools and confidence to start mapping out your own profitable, high-touch retreat—without second-guessing every decision.

Whether you’re ready to book the venue or just daydreaming about adding an in-person offer, let’s talk about how to make it sustainable, scalable, and truly transformational.

On This Week’s Episode, We Discuss:

• Why in-person is booming: Face-to-face events are back—and outperforming virtual.
• The ROI of retreats: More revenue, deeper impact, stronger client loyalty.
• What to charge (and why): The $2K–$5K attendee range that still converts.
• Designing retreats that sell: How to create high-converting event experiences.
• The Hilton event model: “Prepare, Comfort, Engagement”—and how to apply it.
• Avoiding major mistakes: What to never do (think: bland venues, unclear outcomes).
• Upsells that feel good: How retreats naturally feed into your bigger offers.
• Creating true community: Why live events build raving fans and referrals.
• First retreat steps: From survey to beta—how to start smart.
• Jennie’s lessons learned: The behind-the-scenes of what worked (and didn’t).

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Streamline Your Biz with GoHighLevel:

Ready to simplify your software and save hundreds each month? I’ve personally switched to GoHighLevel (GHL) and it's been a game-changer—consolidating my funnels, CRM, email marketing, automations, scheduling, and more into one powerful platform.

Check out GoHighLevel here

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Am I over-investing in software and tools I don’t really need?

Have you ever found yourself drowning in software subscriptions, chasing shiny new tools, or outsourcing yourself right into overwhelm—only to realize your profits aren't reflecting your effort?

If that hits a little too close to home, trust me—I’ve been there! (Hello, "Confusionsoft" days! 😉)

In this candid conversation, I’m joined by monetization and funnel expert Conny Twomey to unpack the sneaky trap we call "six-figure bloat." It’s that all-too-common tendency for growing entrepreneurs to overspend on tech, tools, and outsourcing in the name of scaling—usually at the expense of simplicity, clarity, and profit.

Together, Conny and I share our messy missteps, mindset traps, and how we finally learned to run our businesses lean, intentional, and truly profitable. Plus, we dive into exactly why we both love using Systeme.io as a lean and powerful alternative to bloated, complicated software.

Whether you're just cracking five figures or scaling toward seven, this conversation will help you streamline your business and reclaim your peace of mind (and your profits!).

On This Week’s Episode, We Discuss:

• Six-Figure Bloat (and How to Spot It): How overspending on software and outsourcing secretly sabotages profits.
• Keeping Your Business Lean (Even While Scaling): Why simplicity is the secret to sustainable growth and higher profits.
• Our Personal Tech Misadventures: Real-life lessons from costly mistakes (so you don’t have to make them).
• The Emotional Side of Spending: Identifying impulse buying, shiny-object syndrome, and business FOMO.
• Strategic Outsourcing—The $10, $100, and $1,000 Tasks: How to delegate wisely (and keep what matters).
• How to Audit Your Tech Stack (No Mercy!): A step-by-step method to cut excess, simplify operations, and boost profits.
• Choosing & Transitioning Tools Without Headaches: Smooth and strategic tips to upgrade your tech—minus the overwhelm.
• Mindset Shifts for Profitable Scaling: Conny’s wealth mindset advice for breaking income ceilings without bloat.
• Building Funnels & Monetizing Smartly: High-converting funnels, lean tech, and intentional monetization strategies.
• Running a Location-Independent Business: How Conny’s simplified systems let her work (and thrive!) from anywhere.

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Tools Mentioned:

• Systeme.io (the simplified, all-in-one tool both Conny and I trust!)

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Don't Forget to Follow and Review:

Loving the Acquire podcast?

Make sure to follow and leave a review on Apple Podcasts! Your reviews help me reach and help more entrepreneurs like you. Head over to Apple Podcasts, rate us with five stars, and share your favorite moment from today’s episode!

===

Connect with Conny:

Follow Conny on Instagram: https://www.instagram.com/workwithconny/

Follow Conny on Facebook: https://www.facebook.com/workwithconny/

Follow Conny...

Have you ever felt secretly burnt out in your own business, even when everything looks great on paper?

Maybe you've started feeling resentful towards clients. Maybe you're losing your excitement and can barely motivate yourself to show up at your desk. Maybe you're even wondering, "Why do I feel so isolated when everyone else seems to be thriving?"

Trust me, friend, I’ve been there.

In this very personal episode, I'm opening up about my long journey with depression, burnout, and feeling completely out of alignment in my business, and exactly how I reclaimed my joy, passion, and energy.

If you’ve ever wondered if it’s just you, if you’re doing entrepreneurship "wrong," or if there's a way out of feeling stuck and unhappy, I promise, this one’s for you.

Trigger warning: This episode discusses personal experiences with depression. Please take care of yourself, and skip this episode if it feels sensitive or triggering right now. I’ve got plenty of tactical marketing and sales episodes waiting for you when you’re ready. 💖

On This Week’s Episode, We Discuss:

• My Personal Mental Health Journey: How depression and burnout deeply impacted my business.
• Spotting Burnout & Resentment: Why losing joy and feeling resentful are key signals you can't ignore.
• The Entrepreneurial Paradox: Why business freedom can sometimes feel isolating and overwhelming.
• My Biggest Fear in Pivoting: Facing the reality of making big changes when others depend on you.
• Auditing My Business for Joy: Practical steps to redefine your offers and client work.
• Stepping into the Fractional CMO Role: How embracing strategic marketing reignited my passion.
• Setting Healthy Boundaries: Revamping my onboarding and schedule to protect my energy.
• Combating Isolation & Choosing Joy: Being selective with projects to avoid resentment.
• Giving Yourself Permission to Pivot: Recognizing when change is essential—without guilt.
• Mental Health as a Core Strategy: Why prioritizing self-care and mental wellness is non-negotiable.

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Don't Forget to Follow and Review:

Loving the Acquire podcast?

Make sure to follow and leave a review on Apple Podcasts! Your reviews help me reach and help more entrepreneurs like you. Head over to Apple Podcasts, rate us with five stars, and share your favorite moment from today’s episode!

====

Streamline Your Biz with GoHighLevel:

Ready to simplify your software and save hundreds each month? I’ve personally switched to GoHighLevel (GHL) and it's been a game-changer—consolidating my funnels, CRM, email marketing, automations, scheduling, and more into one powerful platform.

Check out GoHighLevel here

(This is an affiliate link—I only recommend tools I absolutely love and use myself!)

====

Connect with me here

Want to grow your email list or launch your next product to a ready list of leads? Let’s talk

Join the Facebook community