Small Business Survival Conversations

Hosted by Anna Steinfest

Business

Website RSS feed

Episodes

235

Latest episode

Aug 2026

Language

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

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

August 24, 2026Episode 10222 min

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

August 21, 2026Episode 10124 min

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 business Making the transition from practitioner to CEO What people misunderstand about dyslexia The realities nobody prepares you for as a business owner Building and leading a people-first organization Growing without losing sight of your mission Lessons from the Green Bay Packers Mentor-Protégé Program Perseverance through the difficult seasons of entrepreneurship What “survival” really means as a small-business owner About 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.

August 17, 202617 min

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.

August 10, 2026Episode 100128 min

What Nobody Tells You About Hitting Rock Bottom in Business

Send us Fan Mail Most people will tell you to stay positive. Push through. Keep going. Nobody tells you what to actually do when everything falls apart. This Monday morning on Small Business Survival Conversations, Anna Steinfest delivers one of the most honest episodes she's ever recorded — not about how to avoid failure, but about what failure is actually trying to teach you, and how the entrepreneurs who build something lasting are rarely the ones who never hit bottom. They're the ones who learned what to do when they got there. If you've ever lost a client you couldn't afford to lose... launched something nobody bought... made a hire you regret... or opened an email that said "we've decided to go in another direction" — this episode will change the way you see the season you're in right now. Inside this episode: ✅ Why one bad event becomes a story about your entire future — and how to stop it ✅ The house metaphor that reframes everything you think you lost ✅ The most dangerous lie business owners tell themselves after failure ✅ Why "I am a failure" and "my business failed at something" are not the same sentence ✅ How to study your failure like a business tool instead of carrying it like a wound ✅ The three-column exercise that shows you exactly what's still standing ✅ Why your comeback doesn't need to be dramatic — it just needs to move Business Warriors, rock bottom is not where your story ends. It's the first solid ground you've stood on in a very long time. 🎧 New episodes every Monday morning — your weekly reset before the week begins. 👉 Subscribe so you never miss a Monday morning conversation. 💬 Drop a comment below: What's the one thing failure taught you that success never could? Chapters: 00:00 – Welcome & Cold Open: This Episode Is for You 02:30 – When Failure Feels Permanent 05:00 – The House That Fell Down 07:30 – You Are Not Starting Over 09:30 – The Expensive Education of Entrepreneurship 11:30 – Failure and Identity: The Most Dangerous Confusion 13:30 – Turn Around and Look at the Wreckage 15:30 – What Is Still Standing? 17:30 – Don't Rebuild the Same House 19:30 – The Fear of the Next Failure 22:00 – The Next Small Move 24:00 – Someday You May Thank This Version of Yourself 25:30 – Your Action Step This Week 27:00 – A Thought to Leave You With #SmallBusiness #Entrepreneurship #MondayMotivation #BusinessMindset #RockBottom #Resilience #SmallBusinessOwner #FailForward #BusinessGrowth #SmallBusinessSurvivalConversations

August 3, 2026Episode 10025 min

He Bought Useless Land Full of Rattlesnakes. Here's What He Built Instead

Send us Fan Mail He Bought Useless Land Full of Rattlesnakes. Here's What He Built Instead. What do you do when everything you've invested in looks like a complete failure? Most people complain. Most people quit. Most people spend years talking about the terrible hand they were dealt. This farmer did something nobody expected. This Monday morning on Small Business Survival Conversations, Anna Steinfest shares one of the most powerful entrepreneurial lessons she's ever discovered — hidden inside a 2,500-year-old principle and one of the strangest business stories you've ever heard. It's not about luck. It's not about capital. It's not about perfect timing. It's about the one question that separates entrepreneurs who build from the ones who only ever talk about what went wrong. If you've ever felt like your business circumstances were working against you — this episode will change the way you see every obstacle in front of you. Inside this episode: ✅ The farmer who turned hundreds of rattlesnakes into a thriving business destination ✅ Why the best entrepreneurs don't eliminate problems — they mine them for opportunity ✅ The two-line letter that transformed a miserable man in the desert into a published author ✅ How Airbnb, Netflix, and Uber were all built from somebody's frustration ✅ Why complaining has a zero percent success rate — and what to do instead ✅ A simple 15-minute exercise to find the opportunity hiding in your biggest problem right now Business Warriors, your greatest business opportunity may be disguised as the very problem you're trying hardest to avoid. 🎧 New episodes every Monday morning — your weekly reset before the week begins. 👉 Subscribe so you never miss a Monday morning conversation. 💬 Drop a comment below: What's the biggest "rattlesnake" in your business right now — and what could be hiding inside it? Chapters: 00:00 – Welcome & Cold Open: What Are You Carrying Into This Week? 01:15 – The Farm Nobody Wanted 03:00 – When Everyone Else Sees a Problem 05:00 – The Desert and the Stars 07:15 – Every Business Has Rattlesnakes 08:45 – The Question That Changes Everything 10:00 – The Real Cost of Complaining 11:30 – What Are YOUR Rattlesnakes? 12:45 – Your Action Step This Week 13:30 – A Thought to Leave You With #SmallBusiness #Entrepreneurship #MondayMotivation #BusinessMindset #BusinessOwner #Resilience #EntrepreneurLife #SmallBusinessSurvivalConversations #BusinessGrowth #SuccessMindset

July 27, 2026Episode 9912 min

The Pound of Butter Story Every Business Owner Needs to Hear

Send us Fan Mail Every business runs on trust — but trust isn't measured by your website, your logo, or your marketing. It's measured in hundreds of small, everyday moments. This week's Monday Morning Motivation tells the story of a farmer, a baker, and a pound of butter — and the surprising twist about who was really being weighed. If you've ever wondered what your business would reveal if it were put on a scale today, this one's for you. 🎙️ This is Small Business Survival Conversations — real talk for entrepreneurs building something that lasts. 💛 Thought for the week : "Profits may build a business. But trust builds a legacy." 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. TIMESTAMPS 0:00 – Cold Open 1:30 – The Story 3:30 – The Mirror We Don't See 4:45 – Every Business Has a Scale 6:00 – The Small Things Are Never Small 7:15 – Your Customers Are Always Weighing You 8:15 – The Hardest Person to Fool 9:15 – What Goes Around... 10:00 – The Businesses That Last 11:00 – Your Action Step 11:45 – Thought for the Week 12:30 – Closing #SmallBusinessSurvival #MondayMotivation #BusinessWarriors #Entrepreneurship #SmallBusinessOwner #Trust #Integrity #BusinessMindset #MondayMorningMotivation #CustomerTrust

July 20, 2026Episode 9814 min

You Can't Climb the Ladder With Your Hands in Your Pockets

Send us Fan Mail Every entrepreneur knows the temptation to wait — for more money, more confidence, more perfect timing. This week's Monday Morning Motivation starts with one line from Arnold Schwarzenegger: "You can't climb the ladder of success with your hands in your pockets." From there, it's a story about two farmers, the hidden cost of "someday," and why growth almost never happens inside your comfort zone. If you've been staring at your ladder instead of climbing it, this one's for you. 🎙️ This is Small Business Survival Conversations — real talk for entrepreneurs building something that lasts. 💛 Thought for the week: "You can't climb the ladder of success with your hands in your pockets." 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. TIMESTAMPS 0:00 – Cold Open 1:15 – The Ladder 3:00 – The Illusion of "Someday" 5:15 – The Farmer's Lesson 7:00 – The Hidden Cost of Comfort 9:15 – Every Rung Looks Small 10:45 – Thought for the Week 11:30 – This Week's Action Step 12:15 – Closing #SmallBusinessSurvival #MondayMotivation #BusinessWarriors #Entrepreneurship #SmallBusinessOwner #TakeAction #BusinessMindset #ArnoldSchwarzenegger #MondayMorningMotivation #GrowthMindset

July 13, 2026Episode 9710 min

Don't Hide the Crack, Fill It With Gold | Monday Morning Motivation

Send us Fan Mail Every business owner has a crack in their story — the launch that flopped, the client who left, the year the numbers didn't work. This week's Monday Morning Motivation tells the story of kintsugi, the Japanese art of repairing broken pottery with gold, and what it teaches us about turning our business setbacks into our most valuable asset. If you're in the middle of a hard season right now, this one's for you. 🎙️ This is Small Business Survival Conversations — real talk for entrepreneurs building something that lasts. 💛 Thought for the week: "Don't hide the crack. Fill it with gold." 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. TIMESTAMPS 0:00 – Cold Open 0:45 – The Story of the Shogun's Bowl 3:30 – What Kintsugi Teaches Us About Business 7:00 – If You're in the Crack Right Now 9:30 – Thought for the Week 11:00 – This Week's Action Step 12:00 – Closing HASHTAGS #SmallBusinessSurvival #MondayMotivation #BusinessWarriors #Entrepreneurship #SmallBusinessOwner #Kintsugi #ResilientBusiness #BusinessMindset #FailureToSuccess #MondayMorningMotivation

July 6, 2026Episode 9615 min

The Spider Who Saved a Pig (And What It Teaches You About Business)

Send us Fan Mail She had no money. No power. No influence with the farmer. Just a web — and she used it to save a life. In this week's Monday Morning Motivation, we're going back to a barn most of us know from childhood — Charlotte's Web — but looking at it through a business owner's eyes. What starts as a story about a spider and a pig turns into a masterclass on branding, mentorship, reputation, and leadership. If you're building a small business and some weeks it feels like no one notices your value... this episode is for you. Here's what we cover: ✅ Why your business is only as strong as the story people tell about it ✅ Why your greatest competitive advantage might be one person who believes in you ✅ Why great reputations are built one thread at a time — not overnight ✅ Why the best leaders help other people shine instead of chasing the spotlight ✅ Why your legacy was never your business — it's the people you leave better than you found them Grab your coffee, take a breath, and let's start this week the right way. If this episode encourages you, share it with one entrepreneur who needs to hear it — and don't forget to subscribe for a new Monday Morning Motivation every week. Chapters (paste directly into YouTube description) 00:00 Welcome — Monday Morning Motivation 00:30 The Story of Charlotte's Web 03:30 Lesson 1: Your Business Is Only as Strong as Its Story 05:00 Lesson 2: Someone Who Believes in You 06:30 Lesson 3: Reputations Are Built One Thread at a Time 07:45 Lesson 4: Great Leaders Help Others Shine 09:00 Lesson 5: Your Legacy Isn't Your Business 10:15 Two Questions to Ask Yourself This Week 11:15 This Week's Challenge 12:15 Closing Thoughts Hashtags #SmallBusinessSurvivalConversations #MondayMorningMotivation #SmallBusinessTips #Entrepreneurship #BusinessLeadership #CharlottesWeb #BusinessMentorship #SmallBusinessOwner #BusinessMotivation #StartupAdvice