The Modern Insurance Agent

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What happens when a millennial couple dives headfirst into the insurance world, scales a million-dollar remote business, and decides to share their journey with the world? You get The Modern Insurance Agent!Join David and Elle Denning as they peel back the curtain on the messy, magical, and often hilarious realities of entrepreneurship. From the joys (and challenges) of working together as a couple to running remote teams and traveling the globe, this podcast is your behind-the-scenes look at building a business and a life you love.

  1. 3h ago

    You Insurance Agency Is Growing… So Why Is There No Money in the Bank?

    Send us Fan Mail Your insurance agency is growing. Revenue is increasing. Sales are coming in. So why is there still no money in the bank? In this episode of The Modern Insurance Agent Podcast, David Denning sits down with Anne Napolitano, founder of Anne Napolitano Consulting, to break down insurance agency finances, cash flow management, profitability, budgeting, forecasting, and sustainable business growth. Anne explains why an agency can generate strong revenue and still struggle financially and how better financial visibility can help agency owners make smarter decisions. What You'll Learn Why revenue growth doesn't always mean more cashHow to improve insurance agency cash flow and profitabilitManaging chargebacks and building financial reservesWhy you shouldn't run your agency based on your bank balancHow budgeting and forecasting support smarter hiring and growthHow financial dashboards improve decision-makingThe difference between bookkeeping and strategic financial managementWhy strong financial records matter when financing or selling an agencyHow AI is changing accounting and financial managementIf you're an insurance agent, agency owner, producer, or entrepreneur, this episode will help you better understand the numbers behind your business and build a more financially sustainable insurance agency. Connect with Us: 🔗Download the resources & access the full podcast library – jumpstartgonow.com/podcast Join the Movement of Modern Insurance Agents! Ready to become the agent clients trust and refer to their friends? Start by building your personal brand, using social media effectively, and prioritizing relationships over transactions. Let’s change the way people see insurance one client at a time! 🚀 📢 Join the discussion! Connect with like-minded agents and get exclusive marketing tips in the Marketing for Insurance Agents Facebook Group. jumpstartgonow.com/join-group

    You Insurance Agency Is Growing… So Why Is There No Money in the Bank?
  2. 2d ago

    Cold Calling Is Dying: How Insurance Agents Can Build a Digital-First Business

    Send us Fan Mail Buy the leads. Work the script. Make more calls. And if it isn't working… just dial MORE. That's the playbook many new insurance agents are handed. But Chris Chappell believes the future of insurance looks very different. After 17 years in the tech industry, Chris walked away from the highest income of his career because the stress was affecting his health, confidence, and ability to show up as the husband and father he wanted to be. Then he started over in insurance. Today, Chris is a life insurance advisor in Arizona serving millennial parents and he's intentionally building a completely different kind of insurance business. Digital-first. Relationship-first. Low-pressure. A business flexible enough that sometimes his office is the front seat of his Rivian while his kids are at swim practice. In this episode of The Modern Insurance Agent Podcast, David Denning and Chris explore what happens when you stop trying to become the insurance agent the industry tells you to be and start building a business that fits your personality, values, clients, and life. In This Episode, You'll Discover: Why Chris left a 17-year career in tech to start over in insuranceWhat corporate leadership taught him about systems, teams, and business growthWhy earning more money wasn't enough when his career was costing him in other areas of lifeWhat it was really like going from a steady W-2 paycheck to commission-only insurance salesWhy Chris believes the insurance business is surprisingly “figure-out-able”How he's applying software development principles and agile frameworks to his insurance businessWhy he rejected the traditional hustle-and-grind sales cultureHow he works his insurance business around his family instead of forcing his family around his businessWhy he refuses to use pushy insurance sales tacticsHow he's positioning himself as an advisor instead of another salespersonWhy millennial parents are such an underserved insurance marketHow caring for children and aging parents changes the financial conversationWhy cold calling may become increasingly difficult as AI-powered call screening and spam detection improveHow he's using AI for underwriting questions, organization, marketing ideas, and efficiencyWhy he stopped relying on purchased leads and started building an organic, digital-first foundationHow Facebook content is creating conversations without constantly posting about insuranceWhy documenting your actual life and experiences can become part of your marketing strategyWhat Chris would tell new insurance agents transitioning out of corporate AmericaWhy Chris Is Building a Digital-First Insurance Business Chris tried the traditional approach when he first became licensed: Buy leads. Work the script. Keep dialing. But every time his own phone rang from an unknown number especially one marked “potential spam” he realized something. He wouldn't answer it either. As AI-powered call screening and spam detection continue to improve, Chris believes insurance agents who rely heavily on cold outbound calling may need to adapt quickly. So he's building in the opposite direction. Instead of interrupting strangers and trying to convince them to discuss life insurance on his schedule, Chris is creating an online presence that allows people to get to know him first. He's leaning into Facebook, local communities, personal stories, career-transition content, and everyday life as a millennial parent. The opportunity isn't coming from constantly pushing insurance content. It's coming from sharing his life, building relationships, and becoming someone people already know they can talk to when they're ready. A Relationship-First Approach to Life Insurance That philosophy carries directly into Chris's client conversations. He's not interested in pushing someone into a product. He wants millennial parents to understand what they already have, identify potential gaps, explore their options, and make informed decisions without feeling pressured. Chris understands that audience personally. He's raising his own children while also having his mother living with his family a situation many adults are beginning to experience as they support kids, help aging parents, build careers, manage mortgages, and prepare for their own future. That lived experience helps him connect with clients facing similar challenges. The Lesson for New Insurance Agents Chris believes the insurance business is surprisingly “figure-out-able.” Eventually, you're going to hit a wall. But he doesn't see that as evidence you're failing. The wall shows you where you need to grow. The agents who make it aren't necessarily the ones who never struggle. They're the ones who learn, adjust, use the resources around them, and keep moving. If you're an insurance agent, life insurance agent, new producer, agency owner, or someone considering leaving corporate America for insurance, this episode offers a practical look at what building a modern insurance business can actually look like. Connect with Us: 🔗Download the resources & access the full podcast library – jumpstartgonow.com/podcast Join the Movement of Modern Insurance Agents! Ready to become the agent clients trust and refer to their friends? Start by building your personal brand, using social media effectively, and prioritizing relationships over transactions. Let’s change the way people see insurance one client at a time! 🚀 📢 Join the discussion! Connect with like-minded agents and get exclusive marketing tips in the Marketing for Insurance Agents Facebook Group. jumpstartgonow.com/join-group

    Cold Calling Is Dying: How Insurance Agents Can Build a Digital-First Business
  3. 5d ago

    Don't Start Q4 Marketing Until You Watch This

    Send us Fan Mail Every year, Q4 arrives and insurance agents make the same mistake. They buy more leads. Post more on Facebook. Boost a few ads. And start dialing harder than ever. Then, somehow… It backfires. Because Q4 is already the most crowded, expensive, and distracted time of the year. And when everyone starts shouting louder, doing more, and competing for attention, simply increasing your activity isn't always the answer. In fact, the loudest and most rushed marketing approach might be exactly the wrong move at exactly the wrong time. That's why we're putting together a Q4-specific marketing workshop designed to help insurance agents avoid the annual panic and prepare strategically instead. Whether you sell Life, Health, Medicare, or P&C insurance, we'll spend 20 minutes breaking down: ✔️ Why the typical Q4 panic moves buying more leads, posting louder, and dialing harder often backfire, and what to do instead. ✔️ Why the agents who win Q4 aren't necessarily the ones hustling hardest once the season begins. ✔️ The quiet, specific marketing moves successful agents make before Q4 that position them for stronger results. ✔️ A simple 20-day sprint to get your marketing Q4-ready even if you're already feeling behind. And the best part? Everyone who attends live will receive our FREE Q4 Content Calendar Worksheet. It's a simple, plug-and-play tool that helps you plan an entire quarter of content 5 posts per week in about 20 minutes. Plus, it includes an AI prompt that turns your ideas and notes into finished social media posts. So if you'd like to finish the year strong, avoid the Q4 marketing scramble, and give yourself a better chance of writing more policies this season... This workshop is for you. Don't wait until Q4 is already here to start preparing. Get ahead of it now. Connect with Us: 🔗Download the resources & access the full podcast library – jumpstartgonow.com/podcast Join the Movement of Modern Insurance Agents! Ready to become the agent clients trust and refer to their friends? Start by building your personal brand, using social media effectively, and prioritizing relationships over transactions. Let’s change the way people see insurance one client at a time! 🚀 📢 Join the discussion! Connect with like-minded agents and get exclusive marketing tips in the Marketing for Insurance Agents Facebook Group. jumpstartgonow.com/join-group

    Don't Start Q4 Marketing Until You Watch This
  4. Sep 10

    The Leadership Blind Spot Most Business Owners Never See Until It’s Too Late

    Send us Fan Mail What if your employees aren't the problem… but your leadership is? When Ken asked his team whether they always knew when they were doing a good job, only 20% said yes. But when he asked whether they knew when they were in trouble? 80% said yes. That realization changed the way Ken led. Instead of only pointing out what went wrong, he became intentional about recognizing what his team was doing right. And when mistakes happened, he stopped asking: "Who messed up?" He started asking: "Is this a one-time mistake or is there a systemic problem we need to fix?" That shift helped create a culture of accountability without turning every mistake into a personal attack. But Ken learned another powerful lesson: Sometimes you don't have the wrong employee. You have the right employee in the wrong seat. Two employees weren't thriving in their roles. One was introverted but answering the phones. The other was outgoing and magnetic but stuck typing contracts. So Ken switched their positions. Both became happier. The team performed better. And the business benefited. That same philosophy of listening extends to Ken's clients. Today, roughly 75–80% of FUN Enterprises' business comes from repeat business and referrals. His philosophy is simple: Customers are transactional. Clients are people under your care. That mindset became even more important when COVID hit. Ken remembers approximately $350,000 in cancellations in a single week, with total cancellations eventually reaching between half a million and three-quarters of a million dollars. Instead of waiting for things to return to normal, his company adapted—turning in-person experiences into virtual events and eventually rebuilding its live-event business. After more than three decades as an entrepreneur, Ken's advice to anyone building a business today is surprisingly simple: Check your ego at the door. Being vulnerable isn't weakness. Asking for help isn't weakness. Changing direction isn't failure. And admitting you don't have all the answers can be the thing that helps you find better ones. Inside this episode, you'll discover: • How to recognize and reinforce the right behaviors on your team • Why accountability doesn't have to mean blame • How putting the right people in the right roles can transform performance • Why listening is one of the most powerful leadership skills • How repeat business and referrals create long-term growth • How to lead through massive business disruption • Why adaptability matters more than having a perfect plan • The leadership mindset every growing agency owner needs If you're an insurance agency owner, entrepreneur, sales leader, or business owner trying to build a stronger team, improve leadership, create lasting client relationships, and build a business that can survive change, this conversation is packed with lessons you can put into practice. Connect with Us: 🔗Download the resources & access the full podcast library – jumpstartgonow.com/podcast Join the Movement of Modern Insurance Agents! Ready to become the agent clients trust and refer to their friends? Start by building your personal brand, using social media effectively, and prioritizing relationships over transactions. Let’s change the way people see insurance one client at a time! 🚀 📢 Join the discussion! Connect with like-minded agents and get exclusive marketing tips in the Marketing for Insurance Agents Facebook Group. jumpstartgonow.com/join-group

    The Leadership Blind Spot Most Business Owners Never See Until It’s Too Late
  5. Sep 8

    Stop Firing Your Sales Team: Your Sales System Might Be the Real Problem

    Send us Fan Mail Your sales team looks busy. The calls are happening. Meetings are on the calendar. Everyone says they're working. But the revenue isn't following. So… do you have the wrong salespeople? Or did you put good people inside a broken sales system? In this episode of The Modern Insurance Agent Podcast, David Denning sits down with Deborah Newton, founder of Newton Steele, to unpack why sales teams underperform and why hiring, firing, motivating, or demanding "more hustle" won't fix a business without the right foundation. Deborah calls herself a Sales Architect of Success, helping business owners and sales leaders build and rebuild the structure, processes, accountability, and systems behind predictable revenue. And her philosophy is simple: Structure creates consistency. Consistency creates revenue. In this episode, you'll discover: Why your underperforming salesperson might NOT be the real problemHow to tell the difference between a people problem and a system problemWhy you can't hold salespeople accountable for expectations that were never clearly definedWhat happens when an agency hires producers and essentially tells them to "go sell"Why sales training can't fix a broken foundationHow undefined systems create micromanaging agency ownersThe difference between a sales team that's busy and one that's actually productiveWhy revenue can flatline even when everyone appears to be workingHow clearly defined KPIs and processes create accountability without constant hoveringWhy the sales-to-service handoff can quietly destroy the client experienceHow assumptions and "they SHOULD be doing that" create expensive gaps inside a businessWhy onboarding doesn't stop being part of the sales process after the client says yesHow consistency BEFORE, DURING, and AFTER the sale affects retentionWhy the sales systems that worked 10 years ago may need to be rebuilt todayWhere AI fits into modern sales systemsWhy AI should give your team MORE time to build relationships—not eliminate the human element One of the most important ideas Deborah shares is this: You can't hold someone accountable to a process that was never actually defined. If the agency owner thinks the sales process works one way, the sales manager teaches it another way, and the producer executes something completely different… who's actually failing? Before deciding someone is the wrong salesperson, Deborah recommends getting granular: ask the owner, sales leader, producer, and operations team to independently explain the same process. You might be surprised by how different their answers are. And this becomes especially important when an agency owner transitions from being the person who personally generated the revenue to leading a team responsible for generating it. Without clear activity expectations, KPIs, processes, and checkpoints, owners often start hovering because they don't have enough information to trust what's happening. That's when management turns into micromanagement. Deborah also makes an important distinction between winning the client and keeping the client. The things you did to earn the relationship can't disappear once the policy is written. Someone else is still calling. Someone else is still following up. Someone else is still trying to earn that client's business. Consistency has to continue before, during, AND after the sale. And when AI enters the picture? Use it. Deborah believes AI can remove work from your team's plate—but that extra capacity should be reinvested into the part of sales technology can't replace: Human relationships, communication, consistency, and follow-up. If you're an insurance agency owner, sales leader, manager, or producer trying to build a team that produces consistent results without constant micromanagement, this episode will make you look at your sales problems differently. Connect with Us: 🔗Download the resources & access the full podcast library – jumpstartgonow.com/podcast Join the Movement of Modern Insurance Agents! Ready to become the agent clients trust and refer to their friends? Start by building your personal brand, using social media effectively, and prioritizing relationships over transactions. Let’s change the way people see insurance one client at a time! 🚀 📢 Join the discussion! Connect with like-minded agents and get exclusive marketing tips in the Marketing for Insurance Agents Facebook Group. jumpstartgonow.com/join-group

    Stop Firing Your Sales Team: Your Sales System Might Be the Real Problem
  6. Sep 3

    Your Insurance Leads Aren’t the Problem Your Follow-Up System Is

    Send us Fan Mail Buying more insurance leads won't fix a broken sales process. If your producers call a lead once, forget to follow up after a quote, take too long to make first contact, or let old opportunities sit untouched in the CRM… more leads may just mean more wasted money. In this episode of The Modern Insurance Agent Podcast, David Denning sits down with Kenzie Scott, National Business Development Manager at Ricochet 360, to break down how modern insurance agencies are using CRMs, dialers, automation, workflows, and better processes to get more value from the leads they already have. And one of the biggest takeaways? Sometimes the lead isn't the problem. The system around the lead is. Kenzie shares what she's seeing inside insurance agencies across the country and why the agencies growing fastest aren't simply telling producers to "make more calls." They're building systems that make it easier for their teams to do the RIGHT activity at the RIGHT time. In this episode, you'll discover: Why insurance agencies may be blaming their leads for a process problemWhat speed-to-contact means and why it mattersWhy calling an insurance lead once isn't enoughHow a CRM + dialer can remove dozens of tiny decisions from a producer's dayHow Ricochet 360's "Shark Tank" approach keeps leads from sitting untouchedWhy old leads, requotes, recycled leads, and win-backs shouldn't disappear into your CRMHow automation can help producers consistently follow up after a quoteWhy dedicated sales producers can outperform hybrid sales/service rolesHow agencies can use technology without turning producers into automation expertsWhy buying the right software isn't enough if your team doesn't actually use itHow gamification can help create team buy-in around new technologyWhy service workflows may be one of the most overlooked growth opportunities in an insurance agencyHow AI could change service, reporting, certificates, and other repetitive agency tasksWhy technology should give insurance agents MORE time for human conversations not replace themWhat insurance agencies need to do now to stay competitive in 2026 Kenzie shares some eye-opening observations about follow-up. According to the data she discusses in the episode, 41% of producers call a lead only once, while 48% don't follow up after providing a quote. That's a huge problem when agencies are spending thousands of dollars generating opportunities. Instead of constantly feeding producers new leads, Kenzie explains how the right system can continually prioritize new leads, recycled leads, requotes, and win-backs so producers always know who they should contact next. But there's another important lesson: Technology alone won't fix your agency. You can buy an incredible CRM, dialer, or automation platform, but if your team doesn't learn the system and change its habits, you're essentially putting an inexperienced driver behind the wheel of a Lamborghini. The tool AND the behavior around the tool have to work together. And this isn't only about sales. Kenzie believes service automation and workflows are a major untapped opportunity for growing insurance agencies. The right systems can help service teams manage follow-ups and repetitive tasks while freeing humans to spend more time doing what technology can't replace: taking care of clients. If you're an insurance agent, agency owner, producer, or sales manager trying to close more business without simply working more hours, this episode will make you rethink how leads move through your agency. Connect with Us: 🔗Download the resources & access the full podcast library – jumpstartgonow.com/podcast Join the Movement of Modern Insurance Agents! Ready to become the agent clients trust and refer to their friends? Start by building your personal brand, using social media effectively, and prioritizing relationships over transactions. Let’s change the way people see insurance one client at a time! 🚀 📢 Join the discussion! Connect with like-minded agents and get exclusive marketing tips in the Marketing for Insurance Agents Facebook Group. jumpstartgonow.com/join-group

    Your Insurance Leads Aren’t the Problem Your Follow-Up System Is
  7. Sep 1

    $0 to $2 Million in 4 Years: How This Insurance Agent Built a Referral Machine

    Send us Fan Mail What does it actually take to build an insurance business from $0 to more than $2 million in premium in just four years? For Stacie Warner, it wasn't buying leads. It wasn't spending hours every day cold calling. And it definitely wasn't constantly pitching insurance on social media. In this episode of The Modern Insurance Agent Podcast, David Denning sits down with Stacie Warner, owner of Warner Twins Insurance Services, to break down how she built a thriving commercial insurance business by choosing a niche, building genuine relationships, using social media consistently, and turning happy clients into a powerful source of referrals. Stacie specializes in helping contractors with their commercial insurance needs and she built her practice almost entirely through relationships, referrals, and social media. You'll discover: How Stacie went from the restaurant industry to owning an insurance businessWhy she chose contractors as her insurance nicheThe two major insurance problems she sees contractors struggle withHow she grew from $0 to $2M+ in premium in four yearsWhy buying leads never felt right for the way she wanted to build her businessWhat changed when she started intentionally using social mediaHow she went from HATING being on camera to consistently showing up onlineWhy she focuses on relationships instead of pitching people in the DMsHow contractors started finding her through FacebookWhy roughly 50% of her book of business now comes from referralsHow Centers of Influence and strategic referral partners accelerated her growthWhy Facebook groups became one of her biggest opportunitiesHow she manages her social media in roughly 25 minutes a dayWhy personal content is an important part of her insurance marketing strategyHow clients started tagging and recommending her even when she wasn't actively marketingWhy AI won't eliminate the need for a knowledgeable insurance agentHow Stacie balances building a growing agency while raising twin boysHer vision for eventually building a $1 million revenue insurance agency One of the biggest turning points came when Stacie stopped wondering where her next lead would come from and started building a system around relationships and visibility. After implementing the strategy, contractors began reaching out to her on Facebook. Then those contractors referred other contractors. Eventually, clients started tagging her whenever someone in their communities asked for commercial insurance recommendations. Today, Stacie estimates approximately 50% of her book comes from referrals including referrals that originated from relationships she initially built through social media. And here's what makes her social strategy especially interesting: She's not spending all day creating content. Stacie says she spends about 25 minutes at most on Facebook, sharing a mix of her personal life, helpful content, and occasional educational business posts. Instead of constantly saying, "Buy insurance from me," she lets people get to know her and understand what she does over time. That consistency has created something even more valuable than another lead source: A community of people willing to advocate for her. Her clients and sometimes people who haven't even worked with her yet tag Stacie when contractors ask for insurance recommendations inside Facebook groups. If you're an insurance agent who's tired of transactional lead generation and wants to build a business around relationships, referrals, social media, and becoming the go-to agent in your niche, this is an episode you don't want to miss. Connect with Us: 🔗Download the resources & access the full podcast library – jumpstartgonow.com/podcast Join the Movement of Modern Insurance Agents! Ready to become the agent clients trust and refer to their friends? Start by building your personal brand, using social media effectively, and prioritizing relationships over transactions. Let’s change the way people see insurance one client at a time! 🚀 📢 Join the discussion! Connect with like-minded agents and get exclusive marketing tips in the Marketing for Insurance Agents Facebook Group. jumpstartgonow.com/join-group

    $0 to $2 Million in 4 Years: How This Insurance Agent Built a Referral Machine
  8. Aug 29

    10 Weird Ways Insurance Agents Are Getting Clients (That Actually Work)

    Send us Fan Mail Tired of buying leads, cold calling, and competing with every other insurance agent for the exact same prospects? Maybe it’s time to get a little weird. In this episode of The Modern Insurance Agent Podcast, David and Elle Denning count down 10 unconventional ways insurance agents are getting clients—without relying on the same tired lead-generation strategies everyone else is using. And these aren't gimmicks. They're practical ways to become useful, memorable, and trusted BEFORE someone needs insurance. We’re counting down all 10, including: #10 — Create a resource people keep for YEARS Think new homeowner manuals, Turning 65 cheat sheets, new parent checklists, and other genuinely useful resources. #9 — Sponsor the pain, not the game Forget another banner at the little league field. Sponsor the annoying things people actually want help with. #8 — Become the helpful neighbor online Instead of advertising to your community, become the person everyone already trusts for recommendations and answers. #7 — Make insurance entertaining Turn crazy real-world insurance situations into recurring content people actually WANT to watch. #6 — Give referrals before asking for them Become the person who knows the roofer, CPA, realtor, plumber, attorney, and other professionals your clients need. #5 — Teach where your prospects already gather Libraries, employers, community organizations, churches, and other trusted spaces can put you in front of an entire room of the right people. #4 — Find referral partners at overlooked trigger moments New babies. Retirement. Moving. Divorce. Tax season. Open enrollment. Find the professionals already present when someone's insurance needs change. #3 — Give gifts that actually DO something A great client gift can strengthen your relationship, keep your name around, AND help your client. #2 — Adopt the chaos season Instead of trying to sell when everyone is overwhelmed, become the person who helps them prepare BEFORE the chaos begins. And finally... #1 might sound ridiculous at first but it could be one of the most powerful organic marketing strategies an insurance agent can use. Own a weird, hyper-specific micro niche. Night-shift nurses. Food truck owners. Tattoo artists. CrossFit gym owners. Classic car enthusiasts. Teachers approaching retirement. Heck... even people with backyard chickens. Small communities talk. And when you're the ONLY insurance agent who understands their world, your name can spread quickly. The big lesson behind all 10 strategies is simple: Become useful or memorable before you ever have something to sell. You don't need to try all 10, either. Pick ONE idea that fits your personality, audience, and business and start there. Whether you sell life insurance, Medicare, health insurance, annuities, P&C, or employee benefits, you'll walk away from this episode with ideas you can actually put into action. Connect with Us: 🔗Download the resources & access the full podcast library – jumpstartgonow.com/podcast Join the Movement of Modern Insurance Agents! Ready to become the agent clients trust and refer to their friends? Start by building your personal brand, using social media effectively, and prioritizing relationships over transactions. Let’s change the way people see insurance one client at a time! 🚀 📢 Join the discussion! Connect with like-minded agents and get exclusive marketing tips in the Marketing for Insurance Agents Facebook Group. jumpstartgonow.com/join-group

    10 Weird Ways Insurance Agents Are Getting Clients (That Actually Work)
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About

What happens when a millennial couple dives headfirst into the insurance world, scales a million-dollar remote business, and decides to share their journey with the world? You get The Modern Insurance Agent!Join David and Elle Denning as they peel back the curtain on the messy, magical, and often hilarious realities of entrepreneurship. From the joys (and challenges) of working together as a couple to running remote teams and traveling the globe, this podcast is your behind-the-scenes look at building a business and a life you love.

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