The Strategic Entrepreneur
The Strategic Entrepreneur helps female business owners and women entrepreneurs move past strategy fatigue to decision precision. Hosted by Cindy Gordon, business strategist and coach who built and sold four digital businesses, this podcast delivers pattern recognition frameworks and data-driven clarity for entrepreneurs ready to stop second-guessing every move. Whether you're a solo entrepreneur drowning in strategies that aren't working, a small business owner managing 1-4 contractors who needs to cut through the noise, or a woman in business tired of collecting advice without implementing it, each episode gives you strategic business coaching backed by real data, not assumptions. You'll discover what's worth refining versus releasing in your business, how to make confident business decisions using your actual numbers, and practical frameworks for operating from clarity instead of overwhelm. From business mindset and strategic systems to data-driven growth and cutting through false urgency, every episode of this entrepreneur podcast helps you distinguish between tweaks and pivots so you can make revenue-generating decisions with confidence. Perfect for female entrepreneurs and women business owners who are done with strategy collection and ready for strategic action. No more second-guessing. No more paralysis. Just clear business strategy guidance for what to do next. Ready to operate from clarity? Your strategic breakthrough starts now. Formerly: The Overwhelmed Entrepreneur (originally Thrive in 5)
Episodes
The Strategic Pause: Your Most Underused Power Tool
You're action-oriented, decisive, quick to execute - exactly what built your business. Now those same strengths sometimes create complexity. Business strategist Cindy Gordon reveals how successful entrepreneurs naturally evolve to use the strategic pause as a power tool for major decisions.
In this episode:
- Why the pause is a natural evolution at your level of success
- How to ...
The CEO Energy Reset: Stop Managing Your Business, Start Leading It
You're the highest-paid employee in your own business, not the CEO. In this strategic episode, Cindy Gordon reveals the CEO energy reset that saved her business when she was running 5 websites with 11 contractors. Learn the weekly CEO Dashboard practice, daily CEO habits, and the data-driven approach that stops you from second-guessing every decision.
In this ep...
The Year-End Review That Actually Feels Good (Your Hidden Wins Revealed)
Your year was better than you think. In this transformative episode, Cindy Gordon teaches the Gain Review Framework that reveals all the small wins you're dismissing - the ones actually driving your growth. Learn how consistency compounds, why boring discipline beats dramatic sprints, and how to build next year on what's already working.
In this episod...
Measure Backward to Move Forward: The Progress You're Missing
You're making more progress than you realize - you're just measuring wrong. In this tactical episode, Cindy Gordon reveals the quarterly gain review system that uncovers hidden progress and builds unstoppable momentum. Learn the exact CEO Dashboard metrics to track weekly and how to turn backward measurement into forward momentum.
In this episode, you'l...
Why Your Competition Should Be Your Collaboration (The Abundance Revolution)
What if the people you see as competition are actually your key to growth? In this game-changing episode, Cindy Gordon shares how a travel blogger mastermind taught her that collaboration beats competition every time. Discover the "hype woman method" for turning competitors into collaborators and why supporting others multiplies your own success.
I...
The 7 Money Mindset Myths That Keep You Playing Small (And Broke)
Your money mindset is sabotaging your success - and you probably don't even know it. In this breakthrough episode, Cindy Gordon exposes the seven money myths programmed into you before age 10 that are keeping you undercharging, over-delivering, and staying broke. Inspired by Jen Sincero's badass approach to wealth, discover how to rewrite your money story.
In...
The 5 Life Domains That Fuel Your Business
Your business doesn't fuel your life - your life fuels your business. In this paradigm-shifting episode, Cindy Gordon reveals the five interconnected life domains that determine business success: Physical Energy, Mental Clarity, Emotional Resilience, Relational Wealth, and Spiritual Alignment. Discover why treating business as separate from life is killing your success.
In this episode,...
Stop Trading Time for Money: The Systems That Build Wealth While You Sleep
Millionaires don't work harder than you - they work differently. In this paradigm-shifting episode, Cindy Gordon exposes the hustle lie and reveals the five systems that actually build wealth. Inspired by Rachel Rodgers' approach to million-dollar businesses, discover why systems, not schedules, create sustainable wealth.
In this episode, you'll...
The Moment I Realized I Was Measuring My Success All Wrong - The GAP and the GAIN
Feel like you're never doing enough even when you're crushing it? In this transformative episode, Cindy Gordon reveals why high-achieving entrepreneurs feel constantly behind and how to shift from measuring against impossible horizons to celebrating actual progress. Inspired by Dan Sullivan's gap and gain concept, discover the neuroscien...
You Don't Have to Choose: Both-And Success for Overwhelmed Entrepreneurs
Stop believing the lie that success requires sacrifice. In this game-changing episode, Cindy Gordon reveals how to create "both-and" success instead of exhausting either-or choices. Inspired by Steve Houghton's rich routines philosophy, discover how to have business success AND personal fulfillment without the guilt.
In this episode, you&apos...
Episode 250: The Evolution of the Reality Check Method
In this milestone 250th episode, Cindy Gordon shares the 10 reality checks that transformed her from an overwhelmed entrepreneur drowning in chaos to the creator of the Reality Check Method helping thousands bridge the gap from paralysis to action.
Discover the three reality checks that started everything, the three that clients credit with changing their businesses, and the thre...
Broke-Ass Decisions vs. Million-Dollar Decisions: What You Choose Daily
Every decision you make is either keeping you stuck or moving you forward. In this raw, honest conversation, Cindy Gordon breaks down the difference between broke-ass decisions (based on fear and scarcity) and million-dollar decisions (based on strategy and abundance) - and why this matters even if your bank account isn't there yet.
Inspired by wealth mindse...
Black Friday Special: Shopping Your Own Business First
Before you open your wallet this Black Friday, pause and ask yourself one question: Have you shopped your own business first? In this timely Black Friday special episode, host Cindy Gordon, creator of the Reality Check Method and execution coach for overwhelmed entrepreneurs, reveals why your next big win might not be in someone else's course - it might be in the Google Dri...
Pre-Thanksgiving Special: The Permission Slip You Need This Holiday
Feeling like you need to earn your rest before the holidays? This pre-Thanksgiving episode gives you the permission slip you've been waiting for - but probably wouldn't give yourself. Host Cindy Gordon, creator of the Reality Check Method and execution coach for overwhelmed entrepreneurs, reveals why rest isn't something you earn - it's something...
Thanksgiving Week Reality Check: Gratitude Without the Guilt
Gratitude without guilt for overwhelmed entrepreneurs. Cindy Gordon shares how to practice real gratitude during Thanksgiving week without performing or proving you're grateful enough.
In this episode of The Overwhelmed Entrepreneur, business coach Cindy Gordon breaks down why entrepreneurs feel guilty about gratitude - and how to practice gratitude without ignoring t...
Holiday Business Boundaries: Protecting Your Energy for What Matters
Holiday business boundaries aren't selfish - they're essential. Cindy Gordon shares how to protect your energy during the busy season without burning out or letting your business suffer.
In this episode of The Overwhelmed Entrepreneur, business coach Cindy Gordon breaks down how to set Holiday Business Boundaries that actually work - so you can end the ye...
The 3-Minute Work Setup Routine That Doubles Your Focus (Works Any Time of Day)
Struggling to dive into deep work after interruptions? You're not alone. Most productivity advice focuses on morning routines, but what about when you're starting work at 2pm after client calls, or 8pm after the kids are in bed? In this episode of The Overwhelmed Entrepreneur, business coach Cindy Gordon reveals the 3-minute work setup routine ...
From Survival Mode to CEO Energy - Real Talk for Overwhelmed Entrepreneurs
Are you running your business or is your business running you? In this conversational episode, Cindy Gordon explores the difference between operating from survival mode versus CEO energy, inspired by wealth mindset principles from thought leaders like Rachel Rodgers.
Learn why you're stuck responding to every "urgent" email, undercharging for yo...
Stop Task Switching: The Task Batching Method That Creates Business Momentum (For Overwhelmed Entrepreneurs)
How to stop task switching with task batching. Cindy Gordon shares the batch processing method for overwhelmed entrepreneurs who lose focus constantly switching between different types of work.
In this episode of The Overwhelmed Entrepreneur, execution coach Cindy Gordon breaks down the task batching method - a way to group si...
The Momentum Stack Method: How to Build a Productivity Chain Reaction (Task Stacking for Entrepreneurs)
How to use the task stacking method to build a productivity chain reaction. Cindy Gordon shares the Momentum Stack Method for overwhelmed entrepreneurs who know what to do but can't get started.
In this episode of The Overwhelmed Entrepreneur, business coach Cindy Gordon introduces the Momentum Stack Method - a way to turn sma...
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