Small Business Survival Conversations

Hosted by Anna Steinfest

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Episodes

245

Latest episode

Nov 2026

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EN-US

About the show

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.

Listen to episodes

60 recent

November 2, 202612 min

Your Business Isn’t Finished. It’s Just Doing the Wrong Job.

Send us Fan Mail What do you do when the world stops needing what you've always been good at? Maybe customers are buying differently. Maybe the service that used to pay your bills isn't as popular anymore. And a quiet voice keeps asking, "Am I falling behind? Is it too late to change?" This week's Monday Morning Motivation goes back to a Brothers Grimm fairy tale, The Bremen Town Musicians: four animals (a donkey, a dog, a cat, and a rooster) who were all told they were finished. Instead of giving up, they asked a better question: "What else could we become?" Their answer led them somewhere they never planned to go. You'll learn why your old success can hold you back, how a business can keep what it's learned and use it differently (like a printing company that moves into signage and packaging), why you don't have to do everything yourself, how partnering can help a small business compete with a company ten times its size, and what to do when the plan you started with isn't the best one anymore. You'll also get a 15-minute exercise called the Bremen Challenge: pick one thing that's not working, list three strengths you already have, and take one small step this week. If you've ever wondered whether your best days are behind you, this episode is for you. 🎙️ This is Small Business Survival Conversations — real talk for entrepreneurs and small business owners building something that lasts. 💛 Thought for the week: "You may not need a whole new business. You may just need a new way to use what you've already built." 👉 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 – The Bremen Town Musicians (the story) 5:00 – Your Old Success Can Hold You Back 7:00 – Nobody Walks to Bremen Alone 9:40 – They Never Made It to Bremen (When the Plan Changes) 11:30 – Your Action Step: The Bremen Challenge 13:00 – Thought for the Week 13:50 – Closing #MondayMotivation #SmallBusinessSurvival #BusinessWarriors #Entrepreneurship #SmallBusinessOwner #BusinessMindset #MondayMorningMotivation #BusinessPivot #Resilience #SmallBusinessTips

October 26, 2026Episode 11122 min

Trying to Please Everyone Is Quietly Killing Your Business

Send us Fan Mail Who's really running your business? You? Or the last person who gave you an opinion? This week's Monday Morning Motivation is built on an old fable attributed to Aesop: a miller, his son, and a donkey on the way to market. Every group they pass has a different opinion. They try walking, riding, switching places, and finally... carrying the donkey. By the time they reach the bridge, they've lost the sale, the donkey, and their dignity. All because they tried to please everyone. Sound familiar? Lowering your price because a customer said it was too high. Adding a service because someone suggested it. Saying yes to something that doesn't feel right, just so you don't disappoint anyone. You'll learn why the people giving you opinions rarely have a stake in your business, how one "reasonable" suggestion after another can turn a focused company into a confused one, why not everyone is supposed to be your customer, and the difference between listening and obeying. You'll also get a 15-minute exercise called the Donkey Test, with three questions to ask before you say yes to your next big decision. If you've ever changed direction because of one loud opinion, this episode is for you. 🎙️ This is Small Business Survival Conversations — real talk for entrepreneurs and small business owners building something that lasts. 💛 Thought for the week: "You can listen to everyone without following everyone." 👉 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 – The Miller, His Son, and the Donkey 5:00 – Are You Carrying Your Donkey? 6:30 – Not Everyone Is Your Customer 8:40 – Listen, Evaluate, Then Decide 10:40 – Your Action Step: The Donkey Test 12:15 – Thought for the Week 13:00 – Closing #MondayMotivation #SmallBusinessSurvival #BusinessWarriors #Entrepreneurship #SmallBusinessOwner #BusinessMindset #MondayMorningMotivation #Leadership #CustomerFeedback #SmallBusinessTips

October 19, 2026Episode 11011 min

The Truth You're Avoiding Might Be What Saves Your Business

Send us Fan Mail Is there something in your business you know isn't working... but you keep doing it anyway? This week's Monday Morning Motivation goes back to a fairy tale you probably remember: The Emperor's New Clothes. An emperor, two clever weavers, a suit that doesn't exist, and a whole kingdom too afraid to say so. Until one child says what everyone has been thinking. Turns out that story is a lesson every small business owner needs. The most expensive mistake in business isn't making the wrong decision. It's refusing to admit you made one. You'll learn why your team (and your customers) may have stopped telling you the truth, how falling in love with your own idea can keep you pouring money into something that isn't working, the difference between looking successful and being successful, and why the emperor's biggest mistake was that he kept walking after he knew. You'll also get a 15-minute exercise called the Emperor's Check that you can do this week, to find out where you might be pretending everything is fine. If you've ever said "I'm fine" when you weren't, this episode is for you. 🎙️ This is Small Business Survival Conversations — real talk for entrepreneurs and small business owners building something that lasts. 💛 Thought for the week: "Being wrong doesn't make you a failure. Refusing to learn from it can." 👉 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 – The Emperor's New Clothes (the story) 3:00 – When Nobody Will Tell the Boss 4:35 – Falling in Love With Your Own Idea (Sunk Cost) 6:30 – The Parade: Looking Successful vs. Being Successful 7:45 – The Child Who Told the Truth 9:35 – Your Action Step: The Emperor's Check 10:55 – Thought for the Week 11:45 – Closing HASHTAGS #MondayMotivation #SmallBusinessSurvival #BusinessWarriors #Entrepreneurship #SmallBusinessOwner #BusinessMindset #MondayMorningMotivation #Leadership #SunkCostFallacy #SmallBusinessTips

October 11, 2026Episode 10912 min

Your Competitor Isn't the Problem. Your Mirror Is.

Send us Fan Mail Your competitor's success isn't taking anything from you. Comparing yourself to it might be. This week's Monday Morning Motivation goes back to a story you remember from childhood: the Evil Queen and her magic mirror. She had a castle, a fortune, and a whole kingdom. And the moment someone else had something she wanted, she lost her peace. Sound familiar? Today's mirror just fits in your pocket. It's LinkedIn, Instagram, and the competitor's website you promised yourself you wouldn't check. You'll learn why the mirror will always have another answer, what happens when you start reacting to a competitor instead of learning from one, why a shiny opportunity (like a big contract) can be the poisoned apple of your business, and how to swap "Am I better than everyone else?" for a question you can actually win. You'll also get a 15-minute Magic Mirror Check you can do this week to find out whether your comparisons are helping you make better decisions or just making you feel behind. If you've ever scrolled past someone else's big win and felt your own good year shrink, this episode is for you. 🎙️ This is Small Business Survival Conversations — real talk for entrepreneurs and small business owners building something that lasts. 💛 Thought for the week: "Someone else's success is information. It's not a verdict on your worth." 👉 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 – The Evil Queen and the Magic Mirror 2:30 – Your Modern Magic Mirror 3:45 – When Comparing Turns Into Reacting 5:45 – The Poisoned Apple (Beware the Shiny Contract) 7:35 – Ask a Better Question 9:30 – Your Action Step: The Magic Mirror Check 11:00 – Thought for the Week 11:45 – Closing #MondayMotivation #SmallBusinessSurvival #BusinessWarriors #Entrepreneurship #SmallBusinessOwner #BusinessMindset #MondayMorningMotivation #SmallBusinessTips #CompetitorAnalysis #EntrepreneurMindset

October 5, 2026Episode 10811 min

Peter Pan Would Be a Terrible Business Owner

Send us Fan Mail Peter Pan would make a terrible business owner. And a lot of small businesses are living in Neverland right now without realizing it. This week's Monday Morning Motivation revisits the story you loved as a kid: the boy who never grows up, a magical island full of adventure, and a girl named Wendy who quietly keeps everything running. Peter is great at starting things. Wendy is the one who makes them last. And as a small business owner, you have to be both. You'll learn how to tell if your business is still stuck in Neverland (hint: if the answer to "how do you price this?" is "it depends," listen up), why a business that can't run without you isn't really growing, how to hear the "crocodile" of cash flow before it gets close, and how to keep the magic that made your business special while building something that lasts. If you've ever thought "only I know how to do that," this episode is for you. 🎙️ This is Small Business Survival Conversations — real talk for entrepreneurs and small business owners building something that lasts. 💛 Thought for the week: "Imagination may help you start a business. Discipline helps you keep one." 👉 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 – Welcome + the Peter Pan story 2:15 – The Peter in You 3:35 – The Wendy Your Business Needs 6:25 – The Crocodile (Know Your Numbers) 8:30 – Keep a Little Neverland 10:00 – Your Action Step 10:55 – Thought for the Week 11:30 – Closing (Timestamps are estimated from the script. Adjust to your final recording.) #MondayMotivation #SmallBusinessSurvival #BusinessWarriors #Entrepreneurship #SmallBusinessOwner #BusinessMindset #MondayMorningMotivation #SmallBusinessTips #CashFlow #BusinessGrowth

September 28, 2026Episode 10715 min

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

September 21, 2026Episode 10611 min

"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

September 14, 2026Episode 10511 min

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

September 7, 2026Episode 10412 min

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

August 31, 2026Episode 10312 min

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