Small Business Survival Conversations

Anna Steinfest
  • 5.0 (8)
  • Entrepreneurship
  • Updated Biweekly

Small Business Survival Conversations is the weekly podcast designed to empower entrepreneurs, solopreneurs, and small business owners who are fighting every day to build, grow, and sustain their businesses in a noisy and unpredictable world. Hosted by Anna Steinfest, business strategist, entrepreneur, and founder with decades of experience helping small businesses thrive, this show delivers practical wisdom, mindset fuel, and real-world strategies that small business owners can actually use.  What to Expect Every Week  Monday Morning Motivation Kickstart your week with a powerful story—drawn from timeless fables, real business lessons, or classic wisdom—paired with three actionable steps you can apply immediately. Each episode is crafted to help you regain focus, protect your momentum, and make better decisions as a small business owner. These episodes are short, energizing, and packed with practical insight. Think of it as your weekly dose of clarity, courage, and direction. Occasional Expert Interviews Throughout the season, Anna welcomes entrepreneurs, industry experts, and community leaders who share their experiences, failures, wins, and lessons learned. Whether you’re looking to scale, pivot, or simply survive another day of running a business, these conversations offer the guidance and encouragement you need. Who This Podcast Is For This show is built for: • Small business owners • Solopreneurs • Startup founders • Women-owned businesses • Community-based and service-based entrepreneurs • Anyone navigating growth with limited time, resources, and support If you’re building a business from the ground up—and learning as you go—you’re in the right place.  Why Listeners Love This Podcast • Practical, real-world strategies (no fluff) • Story-driven insights that stick • Weekly motivation designed specifically for small business owners • Action steps in every episode • Honest conversations about what it really takes to survive and grow • Encouragement without sugarcoating Running a small business is not easy — but you don’t have to do it alone. Subscribe now and start your week with inspiration, direction, and the tools to keep moving forward.  Small Business Survival Conversations Your journey. Your grit. Your growth.

  1. 6d ago

    Too Cheap. Too Expensive. Just Right: What Goldilocks Can Teach You About Pricing

    Send us Fan Mail Your price probably isn't the problem. How you presented the choice might be. This week's Monday Morning Motivation goes back to a story you haven't thought about since you were a kid — a little girl, a house in the woods, and three bowls of porridge. Goldilocks wasn't just picking porridge. She was comparing. And comparison changes how people decide, every time. Turns out that's exactly what happens when a customer looks at your price. One option means they're only deciding if it feels expensive. Three real options, clearly different, and the question changes to "which one fits me" — a much better conversation, and usually a much better outcome for your business. You'll learn why customers don't always want the cheapest thing, why your entry-level offer can't be deliberately bad just to make the middle one look good, and why pricing decisions made from fear almost always cost you more than the discount you were trying to avoid. If you've ever been told "your price is too high" and instantly reached for a discount, this episode is your reset. 🎙️ This is Small Business Survival Conversations — real talk for entrepreneurs and small business owners building something that lasts. 💛 Thought for the week: "The best price isn't the one that gets a yes. It's the one that creates value for the customer and profit for the business." 👉 Subscribe for a new Monday Morning Motivation every week, plus full-length conversations with small business owners on growth, pricing, mindset, and everything in between. TIMESTAMPS 0:00 – Cold Open (the Goldilocks story)  1:15 – Goldilocks Goes Shopping  2:45 – The Problem With One Price  4:15 – The Three-Bowl Problem  5:30 – Won't They Just Pick the Cheapest?  7:00 – Numbers, Fear, and What's Really "Just Right"  8:30 – Your Action Step  9:30 – Thought for the Week  10:15 – Closing #MondayMotivation #SmallBusinessSurvival #BusinessWarriors #Entrepreneurship #SmallBusinessOwner #Pricing #PricingStrategy #BusinessMindset #MondayMorningMotivation #SmallBusinessTips

    Too Cheap. Too Expensive. Just Right: What Goldilocks Can Teach You About Pricing

  2. Sep 21

    "Play the Next Ball" — Why Small Business Owners Need to Take Off the Blinders

    Send us Fan Mail You didn't fail because you missed. You're stuck because you're still staring at the shot you already missed while the next one is already on its way. This week's Monday Morning Motivation compares two ways of running a business: like a racehorse with blinders on, charging down a track you already mapped out — or like a tennis player, prepared but never quite sure what's coming across the net next. Most small business owners are trained to think like the racehorse. But business doesn't work like a racetrack. It works like a rally — one unexpected shot after another, and the only real skill is staying in position for the next one. You'll learn why preparation was never about predicting the future, why "that didn't work" and "I'm bad at this" are two completely different sentences, and how to trade the identity of the achiever (who only asks "did I win?") for the identity of the experimenter (who asks "interesting — why?"). If you've been replaying a mistake instead of getting ready for what's next, this episode is your reset. 🎙️ This is Small Business Survival Conversations — real talk for entrepreneurs, small business owners, and anyone trying to keep moving after something didn't go as planned. 💛 Thought for the week: "You can make a mistake without becoming the mistake." 👉 Subscribe for a new Monday Morning Motivation every week, plus full-length conversations with small business owners on growth, resilience, mindset, and everything in between. TIMESTAMPS 0:00 – Cold Open  1:15 – The Ball You Didn't Expect  2:45 – Preparation Is Not Prediction  4:00 – Listen As Much As You Play  5:00 – Don't Keep Playing the Last Point  6:30 – Feedback, Not a Verdict  7:45 – From Achiever to Experimenter 9:15 – Your Action Step  10:15 – Thought for the Week  11:00 – Closing #MondayMotivation #SmallBusinessSurvival #BusinessWarriors #Entrepreneurship #SmallBusinessOwner #Mindset #Resilience #BusinessMindset #MondayMorningMotivation #GrowthMindset

    "Play the Next Ball" — Why Small Business Owners Need to Take Off the Blinders

  3. Sep 14

    The Two Words That Get You Up Any Mountain

    Send us Fan Mail There are two words that got a little engine up a mountain nobody thought she could climb — and they're the same two words behind almost every small business that ever made it past its hardest season. A train breaks down at the bottom of a mountain, carrying toys meant for children on the other side. One by one, the big, powerful engines are asked to help — and one by one, they say no. Too important. Too busy. Not built for that kind of job. Then a little engine — small, unproven, not anyone's first choice — says yes. Not because she's sure she can do it. Because she's willing to try. This week's Monday Morning Motivation revisits The Little Engine That Could — not as a children's story, but as one of the truest things ever written about being a small business owner. You'll learn why belief only matters when it produces action, why "I don't know if I can, but I'm willing to try" has built more businesses than blind confidence ever has, and how to turn an overwhelming goal into one small, doable next step. If you're facing a hill right now — a hard decision, a big goal, a mountain that looks too steep from where you're standing — this episode is for you. 🎙️ This is Small Business Survival Conversations — real talk for entrepreneurs, small business owners, and anyone trying to move something forward, blending practical strategy with real motivation. 💛 Thought for the week: "Don't confuse 'this is difficult' with 'this is impossible.' Those are two very different sentences." 👉 Subscribe for a new Monday Morning Motivation every week, plus full-length conversations with small business owners on growth, resilience, mindset, and everything in between. TIMESTAMPS 0:00 – Cold Open  1:00 – The Little Engine (the full story)  4:15 – What Is Your Hill?  5:15 – Belief Has to Move  6:45 – The First Turn of the Wheel  8:00 – Adaptively Persistent  9:15 – Look How Far You've Already Climbed  10:15 – Your Action Step  11:15 – Thought for the Week  12:00 – Closing #MondayMotivation #SmallBusinessSurvival #BusinessWarriors #Entrepreneurship #SmallBusinessOwner #Motivation #Mindset #Perseverance #MondayMorningMotivation #IThinkICan

    The Two Words That Get You Up Any Mountain

  4. Sep 7

    Everyone Is Working Hard. Nothing Is Moving. Here's Why.

    Send us Fan Mail Nobody's lazy. Nobody's sitting on the sidelines. Everyone is pulling their weight — and somehow, nothing is moving forward. If that sounds familiar, it's not an effort problem. It's a direction problem. This week's Monday Morning Motivation tells the story of the Swan, the Pike, and the Crab — an old fable about three strong, capable characters who all try to move the same cart, and all pull it a different way. It's one of the simplest explanations you'll ever hear for why hard work alone doesn't guarantee progress, why "everyone's busy" isn't the same as "everyone's aligned," and why sometimes the person pulling in three directions at once... is you. You'll walk away with one question to ask this week that can tell you, almost instantly, whether your effort is actually building something — or just wearing everyone out. 🎙️ This is Small Business Survival Conversations — real talk for entrepreneurs, business owners, and anyone trying to move something forward, built for people who want practical strategies alongside real motivation. 💛 Thought for the week: "Hard work creates effort. Alignment turns effort into movement." 👉 Subscribe for a new Monday Morning Motivation every week, and full-length conversations with small business owners navigating growth, setbacks, leadership, and everything in between. TIMESTAMPS 0:00 – Cold Open  1:00 – The Swan, the Pike, and the Crab  2:30 – Working Together Isn't Moving Together  3:45 – Sometimes You Are All Three  5:15 – Hard Work Cannot Fix the Wrong Direction  6:45 – What Is Your Cart?  8:15 – Your Action Step  9:15 – Thought for the Week 10:00 – Closing #MondayMotivation #SmallBusinessSurvival #BusinessWarriors #Entrepreneurship #Alignment #Leadership #Productivity #BusinessMindset #MondayMorningMotivation #WorkSmarterNotHarder

    Everyone Is Working Hard. Nothing Is Moving. Here's Why.

  5. Aug 31

    Did You Build a Business — or a Prison?

    Send us Fan Mail Most small business owners start out chasing freedom — and accidentally build a business that can't function without them. Every decision goes through you. Every customer only trusts you. Every problem lands on your desk. Ten years in, the business has grown, but your freedom hasn't. In this week's Monday Morning Motivation, small business coach Anna Steinfest breaks down the difference between long-term thinking and just staying busy — using Aesop's ant and grasshopper fable as the lens. You'll learn why urgent things scream for your attention while the things that actually build a business (systems, reserves, relationships, delegation) stay quiet until it's too late — and five simple things you can start doing this week to make sure your business is working for you ten years from now, not the other way around. If you're a small business owner, entrepreneur, or solopreneur wondering whether you built a business or just a very demanding job, this episode is your Monday morning reset. 🎙️ This is Small Business Survival Conversations — real conversations and practical strategies for small business owners, entrepreneurs, and startup founders building something that lasts. 💛 Thought for the week: "Today's abundance doesn't guarantee tomorrow's security. And today's small preparation can become tomorrow's freedom." 👉 Subscribe for a new Monday Morning Motivation episode every week, plus full-length conversations with small business owners on growth, leadership, burnout, delegation, and everything in between. Topics covered in this episode: small business growth strategy, business owner burnout, delegation for entrepreneurs, long-term business planning, building a business that runs without you, small business succession planning, business systems and documentation, entrepreneur mindset, building financial reserves for small business. TIMESTAMPS 0:00 – Cold Open  1:15 – The Ant and the Grasshopper  2:45 – The Grasshopper and the Ant, in Business  4:30 – Urgent Things Scream. Important Things Whisper.  5:45 – This Changes Your Monday, Not Just Your Future  7:15 – Did You Build a Business or a Prison?  8:30 – Meet Yourself in 2036  10:15 – Five Seeds You Can Plant Today 11:15 – Your Action Step  12:00 – Thought for the Week  12:45 – Closing #SmallBusinessSurvival #MondayMotivation #BusinessWarriors #SmallBusinessOwner #Entrepreneurship #BusinessGrowth #Delegation #BusinessMindset #MondayMorningMotivation #WorkLifeBalance #BusinessSystems #SoloEntrepreneur

    Did You Build a Business — or a Prison?

  6. Aug 24

    Perfectionism Is Just Fear Wearing a Nice Outfit

    Send us Fan Mail You call it research. Planning. Getting ready. Making sure everything is right. But sometimes perfectionism is just fear wearing a nice outfit — and it's the reason your business is still stuck on Version 1. This week's Monday Morning Motivation looks at the Three Little Pigs like you've never heard it before: not a story about hard work, but a story about three versions of the same business owner. Plus, the bakery that changed her cookie recipe forty times before anyone called it "amazing," and a simple system — Try, Track, Tweak — that turns your next ordinary attempt into real progress. If you've been waiting for the perfect idea before you launch, post, or pitch, this one's for you. 🎙️ This is Small Business Survival Conversations — real talk for entrepreneurs building something that lasts. 💛 Thought for the week: "You don't become brilliant by waiting for a brilliant idea. You become brilliant by refusing to waste what every ordinary attempt is trying to teach you." Subscribe for a new Monday Morning Motivation every week, and full-length conversations with small business owners navigating the real stuff — growth, setbacks, and everything in between. #SmallBusinessSurvival #MondayMotivation #BusinessWarriors #Entrepreneurship #SmallBusinessOwner #Perfectionism #TrytrackTweak #BusinessMindset #MondayMorningMotivation #TakeAction

    Perfectionism Is Just Fear Wearing a Nice Outfit

  7. Aug 21

    Nobody Prepares You for This Part of Running a Business | Dr. Nicole Boyington

    Send us Fan Mail What happens when your business is more than a business—when it's deeply connected to your purpose? In this episode of Small Business Survival Conversations, I sit down with Dr. Nicole Boyington, President and CEO of the Dyslexia Achievement Center, for a conversation about entrepreneurship, leadership, purpose, and the realities of building a mission-driven business. Nicole's work is centered around helping individuals and families navigate dyslexia and learning differences, but behind that mission is another story: the challenge of becoming a business owner and CEO, building a team, leading people, making difficult decisions, and continuing to grow without losing sight of why you started. We talk about the transition from practitioner to business leader, misconceptions surrounding dyslexia, people-first leadership, the lessons Nicole has learned along the way, and what running a purpose-driven organization has taught her about perseverance. Nicole also shares insights from her experience with the Green Bay Packers Mentor-Protégé Program and discusses what she's learned about leadership as the Dyslexia Achievement Center has grown. This conversation isn't just for people in education or healthcare. It's for any small-business owner who has discovered that passion may get you started—but building something sustainable requires an entirely different set of skills. If you've ever wondered whether you're doing it right, struggled with the weight of leading others, or discovered that entrepreneurship is very different from what you expected, this conversation is for you. In this episode, we explore: Turning a personal mission into a sustainable businessMaking the transition from practitioner to CEOWhat people misunderstand about dyslexiaThe realities nobody prepares you for as a business ownerBuilding and leading a people-first organizationGrowing without losing sight of your missionLessons from the Green Bay Packers Mentor-Protégé ProgramPerseverance through the difficult seasons of entrepreneurshipWhat “survival” really means as a small-business ownerAbout the Guest Dr. Nicole Boyington, OTD, OTR, OGA/A, C-SLDI, is President and CEO of the Dyslexia Achievement Center, LLC, an organization dedicated to supporting individuals with dyslexia and learning differences. 🎙️ Small Business Survival Conversations goes behind the success stories to have honest conversations about what it actually takes to build, lead, adapt, and survive in small business. If this episode gives you something you can use in your own business, share it with another entrepreneur who needs to hear it.

    Nobody Prepares You for This Part of Running a Business | Dr. Nicole Boyington

  8. Aug 17

    Breaking the Patterns Holding Your Business Back

    Send us Fan Mail Most small-business owners don’t have an information problem. They already know they should raise their prices, delegate more, make the difficult sales call, hire the right person—or finally let the wrong person go. So why don’t we do it? Ken Dombrowski returns to Small Business Survival Conversations to explore the hidden patterns that can keep business owners stuck, even when they know exactly what needs to change. Drawing on his experience as a former construction business owner, business growth coach, and hypnosis practitioner, Ken and I dig into the psychology behind procrastination, fear, control, self-sabotage, and resistance to change. We also tackle hypnosis head-on: What does it actually have to do with running a small business? Can changing an internal pattern really change business results? And where does mindset work end and good old-fashioned business strategy begin? If there’s something in your business you’ve known for months that you need to do—but you keep finding a reason not to do it—this conversation is for you. Because sometimes your next business breakthrough doesn’t come from learning something new. It comes from finally doing what you already know.

    Breaking the Patterns Holding Your Business Back
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Ratings & Reviews

5
out of 5
8 Ratings

About

Small Business Survival Conversations is the weekly podcast designed to empower entrepreneurs, solopreneurs, and small business owners who are fighting every day to build, grow, and sustain their businesses in a noisy and unpredictable world. Hosted by Anna Steinfest, business strategist, entrepreneur, and founder with decades of experience helping small businesses thrive, this show delivers practical wisdom, mindset fuel, and real-world strategies that small business owners can actually use.  What to Expect Every Week  Monday Morning Motivation Kickstart your week with a powerful story—drawn from timeless fables, real business lessons, or classic wisdom—paired with three actionable steps you can apply immediately. Each episode is crafted to help you regain focus, protect your momentum, and make better decisions as a small business owner. These episodes are short, energizing, and packed with practical insight. Think of it as your weekly dose of clarity, courage, and direction. Occasional Expert Interviews Throughout the season, Anna welcomes entrepreneurs, industry experts, and community leaders who share their experiences, failures, wins, and lessons learned. Whether you’re looking to scale, pivot, or simply survive another day of running a business, these conversations offer the guidance and encouragement you need. Who This Podcast Is For This show is built for: • Small business owners • Solopreneurs • Startup founders • Women-owned businesses • Community-based and service-based entrepreneurs • Anyone navigating growth with limited time, resources, and support If you’re building a business from the ground up—and learning as you go—you’re in the right place.  Why Listeners Love This Podcast • Practical, real-world strategies (no fluff) • Story-driven insights that stick • Weekly motivation designed specifically for small business owners • Action steps in every episode • Honest conversations about what it really takes to survive and grow • Encouragement without sugarcoating Running a small business is not easy — but you don’t have to do it alone. Subscribe now and start your week with inspiration, direction, and the tools to keep moving forward.  Small Business Survival Conversations Your journey. Your grit. Your growth.

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