Think Outside the Boss

013: You’re Growing Your Business… But Losing Control of Your Money | Jim Rasmussen

What if the reason you’re not feeling wealthy… has nothing to do with how much money you make? In this episode of Think Outside the Boss, Katie Armentrout sits down with Jim Rasmussen, co-founder of Pando Wealth and former Chick-fil-A financial consultant, to unpack the truth most high performers avoid: making more money doesn’t automatically create a better life. After two decades helping business operators increase profit, Jim noticed a pattern. The income was growing, but the clarity wasn’t. Leaders were building businesses without building a financial plan, chasing growth without defining what it was actually for. This conversation flips the script on wealth, legacy, and leadership. From the emotional roots of money habits to the dangerous trap of comparison-driven investing, Jim shares what it really takes to move from reactive earning to intentional living. Because wealth isn’t just something you build. It’s something you steward, shape, and ultimately pass on. If you’ve been focused on growing your income but haven’t stopped to ask what it’s all for, this episode will change how you think about money, leadership, and the life you’re actually creating. In this episode, you’ll discover: * Why making more money without a plan leads to long-term dissatisfaction * The difference between a business plan and a financial life plan (and why most people only have one) * How comparison culture quietly drives bad financial decisions * The real reason high earners still feel financially insecure * Why “keeping up with the Joneses” destroys long-term wealth * The moment that changed Jim’s entire perspective on money and legacy * How to shift from reactive spending to intentional wealth building * The identity trap that keeps entrepreneurs stuck in financial stress * Why generosity is a core part of sustainable wealth, not an afterthought * The mindset shift that moves you from chasing money to leading your life with purpose We talk about: * 00:00 Why building wealth without a plan sets the next generation up to fail * 03:00 Growing up between scarcity and investing, and how it shaped Jim’s money mindset * 07:00 What Chick-fil-A operators taught him about income growth and financial confusion * 11:00 The wake-up call that shifted his focus from business profit to personal planning * 15:00 Why most leaders overspend as their income increases * 18:00 The leadership principle that drives culture, loyalty, and long-term success * 22:00 How comparison and social pressure lead to poor financial decisions * 26:00 Why entrepreneurs tie their identity to their business (and how to break it) * 30:00 The process of defining your personal vision for money and life * 34:00 How Pando Wealth approaches financial planning differently * 38:00 The risks of fast money, investing mistakes, and chasing returns * 41:00 Why steady, intentional growth always outperforms short-term wins * 44:00 Final advice for leaders who feel behind, overwhelmed, or financially stuck Connect with Jim * LinkedIn: personal [https://www.linkedin.com/in/jim-rasmussen-cpa-pfs-cgma-cka%C2%AE-cfp%C2%AE-cap%C2%AE-37804a11/] / company [https://www.linkedin.com/company/pandowealth/] * Website: https://www.pandowealth.com/ [https://www.pandowealth.com/] * Bags of Money * Get Out of Your Head by Jennie Allen https://amzn.to/4mWXp9j [https://amzn.to/4mWXp9j] Connect with me * Instagram:https://www.instagram.com/katie_armentrout [https://www.instagram.com/katie_armentrout] * YouTube: https://www.youtube.com/@katiearmentrout [https://www.youtube.com/@katiearmentrout] * LinkedIn:https://www.linkedin.com/in/katiearmentrout [https://www.linkedin.com/in/katiearmentrout] * Newsletter: http://www.peoplefluence.com/newsletter [http://www.peoplefluence.com/newsletter] * Website: http://www.peoplefluence.com [http://www.peoplefluence.com] #FinancialPlanning #BusinessOwners #WealthBuilding

012: She Saved a Client $30K in 5 Minutes. Here's the Question She Asked | Kendra Ramirez

Most business leaders aren't behind on AI because they lack access. They're behind because no one told them they already have it and no one gave them permission to use it. In this episode of Think Outside the Boss, Katie Armentrout sits down with Kendra Ramirez, CEO of KR Digital, Claude Ambassador, and one of the most trusted AI voices in the B2B space, to cut through the noise, the overwhelm, and every excuse keeping leaders on the sidelines of the AI era. Kendra has been building AI since 2018. She's delivered hundreds of sessions, consulted organizations of every size, and once saved a client $30,000 in five minutes by asking five questions no one else thought to ask. This is not a conversation about AI being the future. It's a conversation about why it's already here and what to actually do about it today. From auditing your current tech stack, to why Claude outperforms ChatGPT for voice-driven content, to the data security questions your team is afraid to bring to leadership, Kendra makes AI feel less like a threat and more like the smartest colleague you've never properly introduced yourself to. If you lead a team, run a business, or have been quietly waiting for someone to tell you it's safe to move, this episode is that moment. In this episode, you’ll discover: * Why most businesses are already sitting on AI they've paid for and never activated * The five questions that saved one client $30,000 before they signed a single contract * Why Claude outperforms ChatGPT for human-sounding content and how to switch without starting over * What AI Skills are and why they permanently solve the "re-explaining yourself" problem * The non-negotiable data security rules every leader needs to understand before putting anything into AI * Why free AI tools are more expensive than you realize * How Kendra built a globally read AI newsletter that generates revenue without ever pushing it * The mindset shift from waiting for organizational permission to leading your team into the AI era * Why human-centered AI implementation outperforms technology-centered every single time * How to use your personality assessments inside AI for stronger leadership and team communication We talk about: * 00:00 The real reason your team is waiting on AI and why it starts with you * 04:00 Kendra's early leadership instincts and what it means to "manage up" the right way * 08:00 Why silencing the person who always asks "why" is a red flag, not a relief * 12:00 From technical recruiter to digital pioneer: building a business before anyone believed in it * 16:00 How to trust your gut when every coach in the room says you're wrong * 20:00 Limiting beliefs don't just live in you, they live in everyone giving you feedback * 24:00 Where to start with AI when you genuinely don't know what you don't know * 28:00 The $30K wake-up call: audit your tech stack before you buy anything new * 32:00 Claude vs. ChatGPT: what's actually different and whether you should switch * 36:00 What AI Skills are and how they eliminate the re-explaining problem for good * 40:00 AI data security: what's actually safe to put in, and what never should be * 44:00 How Kendra runs AI enablement from the C-suite to the front line * 48:00 Why human connection is the highest-leverage business strategy of 2026 * 52:00 Lightning round: personality assessments, faith, $10K lessons, and walking out to Alicia Keys Connect with Kendra * LinkedIn: https://www.linkedin.com/in/kendraramirez/ [https://www.linkedin.com/in/kendraramirez/] * Website: https://kendraramirez.com/ [https://kendraramirez.com/] * Newsletter: https://kendratech.substack.com/ [https://kendratech.substack.com/] * Get Out of Your Head by Jennie Allen https://amzn.to/4mWXp9j [https://amzn.to/4mWXp9j] Connect with me * Instagram:https://www.instagram.com/katie_armentrout [https://www.instagram.com/katie_armentrout] * YouTube: https://www.youtube.com/@katiearmentrout [https://www.youtube.com/@katiearmentrout] * LinkedIn:https://www.linkedin.com/in/katiearmentrout [https://www.linkedin.com/in/katiearmentrout] * Newsletter: http://www.peoplefluence.com/newsletter [http://www.peoplefluence.com/newsletter] * Website: http://www.peoplefluence.com [http://www.peoplefluence.com] #AIforBusiness #Leadership #Entrepreneurship

011: Why Great Ideas Die Inside Companies (And How to Finally Get Them Out) | Fiona Stevenson

What if your ideas aren’t failing… you’re just not built to carry them through? In this episode of Think Outside the Boss, Katie Armentrout sits down with innovation strategist and CEO Fiona Stevenson to unpack the uncomfortable truth behind why great ideas stall, die, or never make it out of the room. Because it’s not strategy. It’s not creativity. And it’s definitely not a lack of ideas. It’s human nature. Fiona shares what really happens inside innovation, from fear and perfectionism to leadership blind spots and the emotional resistance that quietly kills momentum. Drawing from hundreds of innovation projects and her new book Built for Breakthrough [https://amzn.to/4203tnN], she reveals why even “foolproof” processes fail when humans are involved… and what actually gets ideas across the finish line. This conversation goes beyond innovation. It’s about leadership, identity, risk, and the courage to move forward when you can’t see the path. If you’ve ever felt stuck between having an idea and actually executing it… this will shift how you think about everything. IN THIS EPISODE, YOU’LL DISCOVER: * Why innovation fails even when the process is “foolproof” * The hidden role fear plays in killing great ideas * Why not seeing the path ahead is actually a good sign * The difference between having ideas and executing them * How perfectionism quietly destroys leadership and innovation * Why your team mirrors your energy, not your intentions * The real reason leaving a stable career feels terrifying * How to build momentum when everything feels uncertain * Why energy, not time, is your most valuable resource * The mindset shift that turns ideas into reality We talk about: * 00:00 Why innovation isn’t actually the problem * 04:00 Fiona’s early leadership instincts and entrepreneurial mindset * 08:00 From corporate comfort to taking the leap into the unknown * 12:00 Why not seeing the path is a sign you’re on the right one * 16:00 The emotional reality of leaving stability behind * 20:00 How Fiona built a million-dollar business in year one * 24:00 The “say yes, make friends, experiment” growth strategy * 28:00 Why energy, not time, determines your output * 32:00 The power of working in your zone of genius * 36:00 Perfectionism, leadership, and the cost of hiding failure * 40:00 Why vulnerability transforms team performance * 44:00 The real reason great ideas stall inside organizations Connect with Fiona * LinkedIn: https://www.linkedin.com/in/fiona-stevenson/ [https://www.linkedin.com/in/fiona-stevenson/] * Website: https://fionastevenson.com/ [https://fionastevenson.com/] * Kindness At Work: https://www.kindnessatwork.com/ [https://www.kindnessatwork.com/] * The War of Art by Steven Pressfield [https://www.amazon.ca/Steven-Pressfield/e/B000AQ8R8Q/ref=dp_byline_cont_book_1] https://amzn.to/3OxunjR [https://amzn.to/3OxunjR] * Built for Breakthrough: https://amzn.to/4203tnN [https://amzn.to/4203tnN] Connect with me * Instagram:https://www.instagram.com/katie_armentrout [https://www.instagram.com/katie_armentrout] * YouTube: https://www.youtube.com/@katiearmentrout [https://www.youtube.com/@katiearmentrout] * LinkedIn:https://www.linkedin.com/in/katiearmentrout [https://www.linkedin.com/in/katiearmentrout] * Newsletter: http://www.peoplefluence.com/newsletter [http://www.peoplefluence.com/newsletter] * Website: http://www.peoplefluence.com [http://www.peoplefluence.com] #Innovation #Leadership #Entrepreneurship

010: Why Most Company Culture Fails (And How to Build One That Actually Scales) | Tim Metzner

What if your culture isn’t what you think it is… but what your team actually enforces? In this episode of Think Outside the Boss, Katie Armentrout sits down with entrepreneur, investor, and founder Tim Metzner to unpack what really builds great companies, and why most leaders get it wrong. Because culture isn’t built through mission statements, perks, or leadership speeches. It’s built in the moments where your team decides what’s acceptable, what’s not, and whether they believe you. Tim shares his journey from early startup exposure to building companies that prioritize people, purpose, and performance, and why the best cultures don’t stay top-down for long. If you’ve ever felt like your team isn’t aligned, your culture isn’t sticking, or your leadership isn’t landing the way you want it to… this episode will change how you see everything. In this episode, you’ll discover: * Why culture is reinforced by teams, not leaders * The hidden difference between saying values and living them * How great cultures become self-policing systems * Why most leaders unintentionally create disengagement * The real reason employees don’t feel valued * How to build trust, care, and accountability inside teams * The missing link between leadership and employee buy-in * Why scaling makes culture harder, not easier * How to create alignment between individual work and company mission * What it actually takes to build a culture that lasts We talk about: * 00:00 How great cultures become self-reinforcing * 04:00 Tim’s early startup experience and entrepreneurial spark * 08:00 First failed startup and lessons on execution * 12:00 Where Tim’s obsession with culture began * 16:00 What happens when employees feel truly valued * 20:00 The gap between leadership intention and impact * 24:00 Aligning personal growth with company growth (The Alliance model) * 28:00 Why scaling breaks culture, and how to fix it * 32:00 Building culture through core values in action * 36:00 When teams start holding each other accountable * 40:00 Should you start a business? The real answer * 43:00 Final leadership lessons and closing insights Connect with Tim * LinkedIn: https://www.linkedin.com/in/timmetzner/ [https://www.linkedin.com/in/timmetzner/] * X: https://x.com/TMetzner [https://x.com/TMetzner] * Website: https://www.fireroad.io/ [https://www.fireroad.io/] * The Alliance: Managing Talent in the Networked Age by Reid Hoffman, Ben Casnocha, and Chris Yeh https://amzn.to/4cFL1Wn [https://amzn.to/4cFL1Wn] Connect with me * Instagram:https://www.instagram.com/katie_armentrout [https://www.instagram.com/katie_armentrout] * YouTube: https://www.youtube.com/@katiearmentrout [https://www.youtube.com/@katiearmentrout] * LinkedIn:https://www.linkedin.com/in/katiearmentrout [https://www.linkedin.com/in/katiearmentrout] * Newsletter: http://www.peoplefluence.com/newsletter [http://www.peoplefluence.com/newsletter] * Website: http://www.peoplefluence.com [http://www.peoplefluence.com] #CompanyCulture #LeadershipDevelopment #BusinessLeadership

009: You Built a Business You Can’t Escape From | Kevin Rains

Why does your business feel harder… the more successful it becomes? In this episode of Think Outside the Boss, Katie Armentrout sits down with EOS Implementer and former multi-location business owner Kevin Rains to unpack the hidden truth behind growth that most entrepreneurs never see coming. Because scaling isn’t just about making more money. It’s about what happens underneath the growth. Kevin shares how he grew a family business 40x, hit breaking points that put everything at risk, and the exact moment he realized that more revenue wasn’t solving the problem, it was exposing it. What most leaders call “growth pains”… are often signs of something deeper. Lack of structure. Lack of clarity. Lack of a system that can actually support what you’re building. If you’ve ever felt like your team isn’t stepping up the way you need, or you’re making more money but enjoying it less, this episode will show you why, and what to do instead. In this episode, you’ll discover: * Why growth can increase chaos instead of solving it * The leadership gap that shows up as your business scales * What “hitting the ceiling” really means (and how to break through it) * Why simplifying your business is the key to scaling it * The real reason profit disappears, even when revenue increases * How to build a business that doesn’t rely on you for everything * What EOS (Entrepreneurial Operating System) actually does inside a company * The shift from reactive leadership to structured, intentional growth We talk about: * 00:00 The hidden cost of growth no one talks about * 01:00 Kevin’s journey from small shop to 40x scale * 05:00 What it feels like to “hit the ceiling” in business * 06:30 Why doing more stops working as you grow * 08:00 Scaling through acquisition and what changes * 09:00 When growth creates risk instead of stability * 10:00 The moment everything almost fell apart * 11:30 Why leaders can’t do it alone (even if they try) * 13:00 Building the right team vs. carrying everything yourself * 14:00 Discovering EOS and creating structure * 16:00 Why most businesses operate in chaos without realizing it * 18:00 Revenue vs. profit, and where leaders get stuck * 19:30 How chaos impacts your team and culture * 21:00 The power of simple systems in complex businesses * 22:00 Doing it yourself vs. getting the right support * 25:00 The real ROI of structure (time, clarity, peace of mind) * 27:00 What a true leadership team actually looks like * 29:00 The weekly meeting that transforms your business * 31:00 Solving the right problems, not just reacting * 33:00 Why most teams avoid hard conversations * 35:00 “Enter the danger” and leading through discomfort * 37:00 Lessons on profit, purpose, and long-term impact Connect with Kevin * LinkedIn: https://www.linkedin.com/in/kevinrains/ [https://www.linkedin.com/in/kevinrains/] * Instagram: https://www.instagram.com/kevin_rains/ [https://www.instagram.com/kevin_rains/] * EOS: https://www.eosworldwide.com/ [https://www.eosworldwide.com/] * Fierce Conversations by Susan Scott: https://amzn.to/48MILLG [https://amzn.to/48MILLG] * Radical Candor by Kim Scott: https://amzn.to/485dELf [https://amzn.to/485dELf] * Profits and Purpose by Kevin A. Rains: https://amzn.to/3Q9p0aV [https://amzn.to/3Q9p0aV] Connect with me * Instagram:https://www.instagram.com/katie_armentrout [https://www.instagram.com/katie_armentrout] * YouTube: https://www.youtube.com/@katiearmentrout [https://www.youtube.com/@katiearmentrout] * LinkedIn:https://www.linkedin.com/in/katiearmentrout [https://www.linkedin.com/in/katiearmentrout] * Newsletter: http://www.peoplefluence.com/newsletter [http://www.peoplefluence.com/newsletter] * Website: http://www.peoplefluence.com [http://www.peoplefluence.com] #BusinessGrowth #LeadershipDevelopment #Entrepreneurship