Small Business Survival Conversations
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.
Episodes
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 b...
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 ...
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 differe...
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 thinki...
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 ba...
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 ind...
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...
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 lasti...
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 en...
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, t...
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...
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.
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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 ...
What do a poor woodcutter from an ancient folktale and the founder of one of the world's most powerful companies have in common?
More than you think.
This Monday, Anna Steinfest takes you on a journey from the caves of Ali Baba to the global headquarters of Alibaba — and reveals the one truth that connects them both: the door only opens for those who keep searching.
In this episode of Small Business Survival Conv...
He wished that everything he touched would turn to gold. And for a moment, it felt like the greatest blessing any king could ask for — until he sat down for a meal and realized his gift had become a prison.
This week on Small Business Survival Conversations, Anna Steinfest revisits the 2,500-year-old story of King Midas — but not the version you've heard before. This isn't a story about greed. It's a stor...
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Burn the boats: the Sun Tzu strategy every entrepreneur needs to hear
In 1519, Hernán Cortés ordered his own ships destroyed on the shores of Mexico — removing any possibility of retreat for his men. Centuries earlier, Sun Tzu described a similar moment: a leader who climbs to a height, then kicks away the ladder behind him.
In this episode, Anna Steinfest unpacks what that ancient idea means ...
Why do so many small business owners quit—not because they lack talent, passion, or vision, but because the mountain in front of them feels too big to climb?
In this inspiring Monday Morning Motivation episode of Small Business Survival Conversations, Anna Steinfest explores a powerful 2,000-year-old lesson from Confucius:
“The man who moves a mountain begins by carrying away small stones.”
Through a ...
What separates businesses that survive from those that truly grow?
In this powerful episode of Small Business Survival Conversations, Anna Steinfest sits down with executive coach and leadership expert Ken Dombrowski to discuss the three core principles behind every successful business.
Together, they break down:
- Why mentorship can accelerate business growth
- The importance of follow-through and execution
- Why evaluati...
Most businesses don’t fail because of competition.
They fail because business owners lose confidence in themselves before they ever reach their full potential.
In this powerful episode of Small Business Survival Conversations, Anna Steinfest sits down with leadership coach and business strategist Ken Dombrowski from Your Executive Life Coaching to discuss one of the biggest hidden struggles entrepreneurs fac...
Feeling exhausted, overwhelmed, or burned out trying to grow your business? In this powerful Monday Morning Motivation episode, Anna Steinfest shares an important reminder for entrepreneurs and small business owners: resting is not quitting.
We live in a world that glorifies nonstop hustle, constant grinding, and pushing harder every day — but what happens when exhaustion starts stealing your creativity, energy...
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