In this episode, I sit down with Scott Finkelstein, founder of Sales Scalers, who's been helping entrepreneurs build sales systems since 2019. With four decades of sales experience—from investment banking to coaching Fortune 500 reps and solo entrepreneurs—Scott breaks down how to remove the overwhelm and negative stigma from sales by creating a repeatable system that feels authentic to you.

Scott's approach is refreshingly human: sales isn't about being pushy or manipulative—it's about helping people. When you shift your mindset from "I'm selling" to "I'm helping," everything changes. You build trust faster, show up with better energy, and connect from the heart instead of the head.

Key insights from our conversation:

1. Get out of your own way: Sales is easy when you believe you're helping people, not just trying to close deals
2. Permission to be yourself: The system gets tailored to YOUR personality—not some cookie-cutter sales script that feels fake
3. AI enhances humanity: Use AI for the repetitive stuff (outreach, scheduling, list-building) so you can focus 100% on the human connection
4. The three-stage sales path: Discovery (asking questions, showing you care) → Demo/Presentation (80-90% consistent, 10% customized to their personality) → Proposal/Close
5. Personalize after automation: Scott uses AI for LinkedIn outreach, but the moment someone responds, he stops the automation and researches them personally
6. Money conversations get easier: When you believe in the value you're providing and know you're helping (not just selling), pricing becomes less anxiety-inducing
7. Consistency creates results: I share a client story—a health coach who went from barely paying bills to earning $20K/month consistently just by systemizing her offers

Scott's final message: You need money to live the life you want. If you can't close sales, you can't pay your bills. So stop overthinking it, build a system, and focus on genuinely helping people.

Connect with Scott: salesscalers.com or find him on LinkedIn

Join the free Facebook Community! Connect, Learn, Grow, Build https://www.facebook.com/groups/freedomentrepreneurcommunity

Biz in a Box CRM is the ultimate all-in-one solution designed to simplify and scale your business. Imagine managing every aspect of your operations — from smart contact segmentation and automated follow-ups to call and text functionality, calendar booking, funnels, websites, and even social media scheduling — all from one intuitive platform. No more juggling multiple tools or paying for endless subscriptions. With built-in AI employee support, Biz in a Box CRM doesn’t just organize your business, it actively helps you run it. It’s like having a full-time team behind the scenes, so you can focus on growth, impact, and freedom.

Book your demo: https://bizinaboxsolutions.com/crm

What if you could stay home with your kids AND build a thriving business—without sacrificing either? In this inspiring episode, Lindsay connects with Catherine Wilkenson all the way from England to unpack exactly how she did it through online English teaching (ESL) and digital printables.

Catherine's journey started with a familiar struggle: she wanted to be present for her babies, but also needed income. After cramming a teaching qualification into one intense year (while pregnant with her second child), she stumbled onto an industry most people don't even know exists—online ESL teaching. Since 2017, she's been teaching English to students around the world from her home, allowing her to homeschool her own children while earning an income.

But here's where it gets really interesting: Catherine didn't stop at teaching. She identified a massive gap in the market—affordable, play-based English learning resources for families who couldn't afford private tutoring. So she built a second income stream through digital printables and curriculum focused on story-based learning for 3-8 year olds. Now she helps families globally through her YouTube channel (free lessons!), her website (TheoET.com), and platforms like Teachers Pay Teachers.

In this episode, you'll learn:

1. How to get started as an online ESL teacher (even without a teaching background)
2. What companies provide—materials, students, and no marketing required
3. The difference between teaching 1-on-1, small groups, and classrooms (and which pays best)
4. How Catherine transitioned from working for companies to freelancing (where rates are significantly higher)
5. Why she chose YouTube, email, and long-form content over social media (and how it's working)
6. The "shiny object syndrome" trap and how accountability partners helped her finally scale
7. How to build a digital product business around what you're already creating

Whether you're a parent desperate to stay home with your kids, a teacher looking for flexibility, or an entrepreneur curious about the digital product world, Catherine's story proves you can build multiple income streams doing work you genuinely love.

Connect with Catherine: TheoET.com | Free resources for families & teachers | YouTube: story-based English lessons

Join the free Facebook Community! Connect, Learn, Grow, Build https://www.facebook.com/groups/freedomentrepreneurcommunity

Biz in a Box CRM is the ultimate all-in-one solution designed to simplify and scale your business. Imagine managing every aspect of your operations — from smart contact segmentation and automated follow-ups to call and text functionality, calendar booking, funnels, websites, and even social media scheduling — all from one intuitive platform. No more juggling multiple tools or paying for endless subscriptions. With built-in AI employee support, Biz in a Box CRM doesn’t just organize your business, it actively helps you run it. It’s like having a full-time team behind the scenes, so you can focus on growth, impact, and freedom.

Book your demo: https://bizinaboxsolutions.com/crm

If you're thinking about leaving your W-2 job but don't know where to start, this episode is your roadmap. Lindsay sits down with Kelly Schuckneckt, founder of Two Mile High Marketing, to unpack exactly how she went from corporate layoff to building a half-million dollar agency in just one year—and how you can do the same by packaging your skills the right way.

Kelly's story starts like so many others: she had a dream of starting her own business, but kept putting it off. For two years, she had a business name, a website, and a vision—but no action. Then came the meeting with HR. Her role was eliminated. And instead of panicking, she made a decision: it was time to bet on herself.

Here's what makes Kelly's story so powerful: she didn't have a huge following, a massive email list, or even a perfect business plan. What she DID have was clarity on her "Authority X Factor"—the unique combination of skills and experience that made her irreplaceable. She packaged what she'd done for her former boss (ghostwriting, speaking engagements, podcast bookings, thought leadership positioning) into a clear, high-ticket offer. Within a week, she had her first client. Within months, she had a team.

In this episode, you'll learn:

1. Why niching down by offering (not industry) is the key to standing out in a crowded market
2. How Kelly turned one case study into a scalable service business
3. The mindset shift from "I'm just worth $50/hour" to "I can sell $25K packages"
4. Why she chose to build an agency instead of staying a solopreneur—and how fast she scaled
5. The exact conversations and communities that landed her first clients (hint: it wasn't cold outreach)

If you've been laid off, furloughed, or just dreaming of ditching your W-2 for a work-from-home lifestyle, Kelly's story proves it's not only possible—it's the fastest path to freedom when you package your expertise the right way.

Connect with Kelly: twomilehighmarketing.com | Take the Thought Leadership Scorecard | LinkedIn: Kelly Schuckneckt

Join the free Facebook Community! Connect, Learn, Grow, Build https://www.facebook.com/groups/freedomentrepreneurcommunity

Biz in a Box CRM is the ultimate all-in-one solution designed to simplify and scale your business. Imagine managing every aspect of your operations — from smart contact segmentation and automated follow-ups to call and text functionality, calendar booking, funnels, websites, and even social media scheduling — all from one intuitive platform. No more juggling multiple tools or paying for endless subscriptions. With built-in AI employee support, Biz in a Box CRM doesn’t just organize your business, it actively helps you run it. It’s like having a full-time team behind the scenes, so you can focus on growth, impact, and freedom.

Book your demo: https://bizinaboxsolutions.com/crm

You've heard it a thousand times: "Make money from what you love." "Build passive income while you sleep." But how do you actually DO it? How do you take something you're passionate about and turn it into a thriving digital business with multiple revenue streams?

In this episode, Lindsay sits down with Michelle Heberling, founder and author of The Guts of Fermentation, to unpack exactly how she transformed her catering expertise and love of food into a multi-layered online business—and how you can do the same with YOUR passion.

Michelle shares her journey from growing up on a farm, to moving to San Francisco during the food movement, to taking clients on off-grid retreats where she cooked life-changing meals that left people raving about their poop stories (yes, really). When her clients kept asking for recipes, she listened—and that listening sparked an entire ecosystem of products, programs, and digital offerings.

Here's what Michelle built from ONE core passion:

1. A book that doesn't just share recipes, but connects the dots between soil health, fermented food, and gut healing (something no one else was doing)
2. Online classes teaching fermentation techniques and her signature two-week gut reset
3. Train-the-trainer certification for health practitioners, nutritionists, and coaches who want to use her protocol with their clients
4. Fermentation kits that make it easy for beginners to get started
5. A phone app (built with AI!) that guides users through personalized gut-health protocols and tracks progress

Lindsay introduces the "Rose Bush Model"—the idea that your business starts with one or two stems, but over time, with care and attention, it grows into a full, thriving bush with multiple branches (revenue streams). Michelle's story is the perfect example of this in action.

You'll also hear how Michelle used AI to organize 127 recipes, format citations, and even build her app—proof that you don't need a huge team or budget to scale your passion into profit.

If you've ever wondered whether you could turn what you love into real income, this episode will show you it's not only possible—it's happening right now.

Connect with Michelle: thegutsoffermentation.com | Instagram: @thegutsoffermentation

Join the free Facebook Community! Connect, Learn, Grow, Build https://www.facebook.com/groups/freedomentrepreneurcommunity

Biz in a Box CRM is the ultimate all-in-one solution designed to simplify and scale your business. Imagine managing every aspect of your operations — from smart contact segmentation and automated follow-ups to call and text functionality, calendar booking, funnels, websites, and even social media scheduling — all from one intuitive platform. No more juggling multiple tools or paying for endless subscriptions. With built-in AI employee support, Biz in a Box CRM doesn’t just organize your business, it actively helps you run it. It’s like having a full-time team behind the scenes, so you can focus on growth, impact, and freedom.

Book your demo: https://bizinaboxsolutions.com/crm

Think summits are dead? Think again. In this tactical, strategy-packed episode, Lindsay sits down with Jessyka Coulter, founder of ACE Cookie Tutoring, who has hosted over 20 virtual summits in just five years—and made them her primary lead generation engine.

If you've ever wondered whether summits are worth the effort, how to find speakers, or what actually converts attendees into paying clients, this conversation will answer every question you didn't know you had.

Jessyka walks us through her entire summit journey—from her very first event (which took three chaotic months to pull together) to her current streamlined process of hosting two high-converting summits per year. She shares the behind-the-scenes logistics most people don't talk about: how she vets speakers, why she asks about email list size upfront, how she structures interviews to keep mamas engaged, and the exact monetization model she uses (VIP passes, webinars, and strategic follow-up sequences).

You'll also hear the surprising mindset shifts that made the biggest difference in her results—including why the energy you bring to speaker outreach actually impacts response rates, and why choosing your lane and staying committed matters more than chasing the latest marketing trend.

Key takeaways include:

1. Live vs. prerecorded: Why Jessyka switched formats based on audience feedback (and how surveys changed everything)
2. Speaker strategy: How to find the right guests, why email list size matters, and what to track with link analytics
3. The sweet spot: Why 5 speakers per day is the magic number, and how shorter interviews with more speakers can outperform fewer long sessions
4. Organic promotion only: How she fills summits without running a single ad (hint: it's all about speaker collaboration and email)
5. The power of consistency: Why marrying one strategy—even an imperfect one—beats pivoting every six months

Whether you're a coach, consultant, course creator, or service provider looking for a scalable way to build your list and attract dream clients, this episode proves that summits are far from dead—they just need to be done right.

Connect with Jessyka: ACE Cookie Tutoring (acecookietutoring.com)

Join the free Facebook Community! Connect, Learn, Grow, Build https://www.facebook.com/groups/freedomentrepreneurcommunity

Biz in a Box CRM is the ultimate all-in-one solution designed to simplify and scale your business. Imagine managing every aspect of your operations — from smart contact segmentation and automated follow-ups to call and text functionality, calendar booking, funnels, websites, and even social media scheduling — all from one intuitive platform. No more juggling multiple tools or paying for endless subscriptions. With built-in AI employee support, Biz in a Box CRM doesn’t just organize your business, it actively helps you run it. It’s like having a full-time team behind the scenes, so you can focus on growth, impact, and freedom.

Book your demo: https://bizinaboxsolutions.com/crm

Ever feel like you're so deeply invested in your clients' outcomes that their wins and losses feel like your own? You're not alone—and it might be holding you back.

In this episode, Lindsay sits down with Shelli Hendricks, founder of Blue Horizon Solutions and a veteran entrepreneur with nearly 10 years of experience helping business owners build sustainable, scalable ventures. Shelli shares a perspective shift that changed everything for her coaching practice: learning to treat her business as its own identity, separate from her personal worth.

Shelli walks us through the emotional trap many consultants and coaches fall into—absorbing their clients' businesses as if they were their own. While this deep care comes from a genuine place, it creates fragmented energy, unclear boundaries, and ultimately limits both the coach and the client. When you take on someone else's business as your responsibility, you rob them of the empowerment to make their own decisions.

Drawing from her background in Fortune 500 leadership development and her work with everyone from scuba shop owners to software developers, Shelli introduces the "Sherpa" mentality: you're the guide with the tools, knowledge, and experience, but the climb belongs to your client. This shift doesn't mean caring less—it means caring strategically.

Throughout the conversation, Lindsay and Shelli dig into practical strategies for separating emotion from decision-making, the power of observing feelings without letting them drive your business choices, and how treating your business like an asset on the shelf (something you can examine objectively) opens up entirely new possibilities you can't see when you're emotionally entangled.

Shelli also shares her four coaching pillars—navigating life transitions, building new businesses, scaling with the Value Builder program, and leadership development—and explains how she structures pricing to reflect value, not just time. Plus, you'll hear a memorable analogy about farm animals that will forever change how you think about attachment to your work.

If you've ever struggled with boundaries, felt drained by your clients' challenges, or wondered how to show up powerfully without burning out, this episode is for you.

Connect with Shelli: Blue Horizon Coach ([email protected])

Join the free Facebook Community! Connect, Learn, Grow, Build https://www.facebook.com/groups/freedomentrepreneurcommunity

Biz in a Box CRM is the ultimate all-in-one solution designed to simplify and scale your business. Imagine managing every aspect of your operations — from smart contact segmentation and automated follow-ups to call and text functionality, calendar booking, funnels, websites, and even social media scheduling — all from one intuitive platform. No more juggling multiple tools or paying for endless subscriptions. With built-in AI employee support, Biz in a Box CRM doesn’t just organize your business, it actively helps you run it. It’s like having a full-time team behind the scenes, so you can focus on growth, impact, and freedom.

Book your demo: https://bizinaboxsolutions.com/crm

Feeling overwhelmed by your business processes? You're either overcomplicating or oversimplifying—here's how to find the sweet spot.

In this episode, I'm joined by Sabena Miller, founder of Kairos XP, a systems and process consultant who's spent decades helping companies—from the New York Stock Exchange to small businesses—streamline their operations. If you've ever felt paralyzed trying to figure out what comes first (the website? the CRM? the email forms?), this conversation will give you clarity.

Sabena's superpower is assessing what's working and what's not, then rebuilding processes so everyone—from employees to customers—can understand and use them effectively. She's not an IT expert or a software specialist; she's a generalist who knows enough about everything to identify whether you need better tools, better processes, or both.

Key insights from our conversation:

1. Start with a workflow: List what you do, break it into steps, and follow one path at a time—don't get distracted by shiny objects
2. Think in phases and outlines: Identify what you need in place before you can build the next thing (like remodeling a kitchen—bring in an expert who knows the new tools available)
3. Client perspective vs. business owner perspective: Start with the problem you're solving and work backward—what's the hangup? What's not working?
4. Word of mouth beats everything: Sabena's clients come from referrals and free value—coaching, content, and genuinely helping people
5. The AI fatigue is real: Everyone's using the same frameworks and prompts, making content feel replicated and salesy—authenticity is your competitive advantage
6. Perfection is the enemy of progress: Authenticity beats polish—people engage with people first, information second. Start messy and refine as you go.

We also went deep on AI, marketing psychology, imposter syndrome, and why your course/service isn't oversaturated just because you see it everywhere (spoiler: algorithms show you what you're already interested in—your audience hasn't seen it yet).

Connect with Sabena: LinkedIn @SabenaMiller or visit kairosxp.com

Feeling overwhelmed by all the business advice online? Here's how one health coach tuned out the noise and found her path.

In this episode, I'm joined by Vera Jackson, a holistic therapist and health coach who helps women navigate hormonal issues like PCOS, fibroids, perimenopause, and blood sugar management. Vera's journey is a masterclass in filtering through the overwhelming amount of business advice available online to find what actually works for you.

After spending three years studying nutritional therapy—completing multiple exams, clinic hours, and case assessments—Vera got her diploma and realized she was starting from absolute zero when it came to marketing and building a business. Sound familiar?

Key insights from our conversation:

1. The only way to weed out the noise is to try: Vera tested different business coaches, attended free webinars, and joined various sessions until she found someone whose energy and messaging resonated with her authentically
2. Clarity comes from refinement: She reworked her messaging multiple times until people could instantly understand what she does and who she serves
3. Package strategically by client needs: Vera offers three tiers—entry-level (2 sessions), intermediate (8-10 weeks), and long-term (up to 6 months)—based on complexity, not arbitrary pricing
4. Small, sustainable changes win: Her approach focuses on manageable shifts in diet and lifestyle that clients can actually maintain (no one's giving up their coffee!)
5. Problem-aware vs. curious clients: She primarily targets people actively seeking solutions, while using community webinars to help curious prospects become problem-aware
6. 2026 strategy shift: Moving from big marketing funnels to local, in-person community meetings—banking on the growing desire for real human connection in an AI-saturated world

Vera's biggest takeaway? In an age where AI makes everything feel fake or too polished, showing up as a real person—whether through face-to-face meetings or authentic online presence—is becoming the most powerful differentiator.

Connect with Vera on Instagram: @vera.jackson.well.being

Think entrepreneurship is hard when you're juggling life? You're not alone—and you don't have to stay stuck.

In this episode, I'm joined by Maranda Taylor, founder of Charm and Strategy, a business consultant who's mastered the art of building a business while navigating single parenthood and financial pressure. If you've ever felt like you're just surviving instead of thriving, Maranda's story and strategies will hit home.

Maranda's journey is anything but linear—from studying metallurgical engineering to owning a martial arts school, getting a real estate license, running a craft business that hit six figures, and finally going all-in on Charm and Strategy just yesterday. She's lived the struggle of doing everything the hard way, and now she's dedicated to helping other entrepreneurs (especially single parents) skip the pain and build strategic, profitable businesses.

What you'll learn in this conversation:

1. The four-step framework: Be delusional, organize your business, have no shame, stay curious—and never let "I know" stop you from asking questions
2. The 15-minute problem-solving rule: Any problem can be solved in 15 minutes if you work backwards from your goal and take immediate action
3. Why being authentically honest matters more than being nice: Sometimes tough love is the greatest gift you can give someone who's stuck
4. The power of being a "sunflower": How showing up as positive support for others' dreams creates ripple effects (and why you should be a "rose" for yourself)
5. How she got her first clients: Showing up, asking questions, and literally sitting with people who were struggling—word of mouth built everything
6. The invitation strategy: Invite yourself to tables where you don't belong and become the "dumbest person in the room"—that's where growth happens
7. Breaking through survival mode: How to shift from paycheck-to-paycheck panic to strategic moves that create contracts and cash flow

Maranda's message is clear: the ceiling isn't real, you're more capable than you think, and if you lead with curiosity and authenticity, doors will open.

Connect with Maranda: charmandstrategy.com or find her on TikTok and Facebook @MarandaTaylorOmaha

Join the free Facebook Community! Connect, Learn, Grow, Build https://www.facebook.com/groups/freedomentrepreneurcommunity

Biz in a Box CRM is the ultimate all-in-one solution designed to simplify and scale your business. Imagine managing every aspect of your operations — from smart contact segmentation and automated follow-ups to call and text functionality, calendar booking, funnels, websites, and even social media scheduling — all from one intuitive platform. No more juggling multiple tools or paying for endless subscriptions. With built-in AI employee support, Biz in a Box CRM doesn’t just organize your business, it actively helps you run it. It’s like having a full-time team behind the scenes, so you can focus on growth, impact, and freedom.

Book your demo: https://bizinaboxsolutions.com/crm

Are you exhausted from trying to be everywhere at once? Posting on every social platform, chasing the latest trends, and wondering if any of it is actually paying off?

In this episode of the Freedom Entrepreneur Podcast, host Lindsay Sutherland sits down with KJ Blattenbauer, founder of Hearsay PR, who spent nearly three decades behind the scenes shaping narratives for founders and experts. KJ shares a refreshing truth: the most successful entrepreneurs aren't always the most talented—they're the most well-positioned and strategic about how they use their time.

What You'll Learn:

KJ breaks down why clarity beats content volume every single time. She explains how to identify your one clear authority angle and repeat it everywhere, rather than burning yourself out creating endless content pillars. You'll discover why your website and social bios need to tell a consistent story before you pursue any visibility strategy, and how to determine where your actual target audience spends their time (hint: it might not be social media at all).

The Power of Borrowed Authority:

One of the most valuable insights from this conversation is KJ's approach to leveraging other people's platforms. She reveals how she's appeared on 165 podcasts for her book launch—without spending a dime—and why being a guest on established platforms is infinitely more efficient than building your own from scratch. You'll learn the simple two-to-three sentence pitch formula that gets media attention, and why press releases might not be your best investment.

Beyond the Tactics:

KJ also addresses something many entrepreneurs struggle with: believing their story isn't interesting enough. She explains why every business owner has a compelling narrative (even if you had a perfectly normal childhood), and how sharing your authentic story—not a manufactured persona—creates the magnetic connection that converts prospects into clients.

If you're ready to stop the content hamster wheel and start building real authority that AI can't replicate, this episode is your roadmap to strategic, sustainable visibility that actually moves the needle in your business.

hearsaypr.com

[email protected]

Join the free Facebook Community! Connect, Learn, Grow, Build https://www.facebook.com/groups/freedomentrepreneurcommunity

Biz in a Box CRM is the ultimate all-in-one solution designed to simplify and scale your business. Imagine managing every aspect of your operations — from smart contact segmentation and automated follow-ups to call and text functionality, calendar booking, funnels, websites, and even social media scheduling — all from one intuitive platform. No more juggling multiple tools or paying for endless subscriptions. With built-in AI employee support, Biz in a Box CRM doesn’t just organize your business, it actively helps you run it. It’s like having a full-time team behind the scenes, so you can focus on growth, impact, and freedom.

Book your demo: https://bizinaboxsolutions.com/crm