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Keep What You Earn

Latest episodes

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Jun 27, 2025 • 12min

Essential W-9 Practices for Compliance

Today's episode focuses on the significance of collecting W-9 forms from contractors and why it can save you time and avoid issues at year-end. We'll discuss the purpose of W-9s, how to effectively collect and manage them, and best practices for keeping your records organized. Ensuring you have up-to-date W-9s can streamline tax filing, prevent penalties, and protect your deductions during audits. Push play to tune in for actionable insights.   What You'll hear in this episode: [00:45] The Importance of W-9 Forms [01:50] Best Practices for Collecting W-9s [05:45] Handling Resistance and Special Cases [06:45] Maintaining and Updating Records [08:30] Why It is Helpful to Get a W-9 from a Contractor who has an S-Corporation, Even Though They Do Not Get a 1099   If you like this episode, check out: End-of-Year Financial Prep: Three Essential Steps for Business Owners Hiring Contractors vs. Employees - Pros and Cons Simple S Corp Salary Guide for Beginners   Want to learn more so you can earn more?   Visit keepwhatyouearn.com to dive deeper on our episodes Visit keepwhatyouearncfo.com to work with Shannon and her team Watch this episode and more here: https://www.youtube.com/channel/UCMlIuZsrllp1Uc_MlhriLvQ Connect with Shannon on IG: https://www.instagram.com/shannonkweinstein/   The information contained in this podcast is intended for educational purposes only and is not individual tax advice. Please consult a qualified professional before implementing anything you learn.
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Jun 25, 2025 • 17min

Businesses I Think Are Unsellable

In this episode, I dive into the types of businesses that are typically challenging to sell. We explore why businesses built on personal brands, online courses, and creative agencies often face hurdles in creating enterprise value. I also discuss the effect of low barriers to entry, lack of proprietary intellectual property, and the impact of AI on these industries. Additionally, I offer actionable advice on how to potentially turn these unsellable models into sellable ones by focusing on systematizing processes, creating recurring revenue streams, and building robust sales pipelines. Remember, if your goal isn't to sell, that's perfectly fine, but it's crucial to set realistic expectations and goals for the future of your business.   What You'll hear in this episode: [00:45] Understanding Sellable vs. Unsellable Businesses [02:30] Challenges of Personal Brand Businesses [04:45] The Decline of Online Courses [07:40] Creative Agencies and AI Impact [10:55] Risks of Affiliate and Trend-Based Businesses   If you like this episode, check out: How to Confidently Leave Your 9 to 5 and Embrace Entrepreneurship How Katie Savarise Built a Culture, Not Just a Brand How to Value a Business   Want to learn more so you can earn more?   Visit keepwhatyouearn.com to dive deeper on our episodes Visit keepwhatyouearncfo.com to work with Shannon and her team Watch this episode and more here: https://www.youtube.com/channel/UCMlIuZsrllp1Uc_MlhriLvQ Connect with Shannon on IG: https://www.instagram.com/shannonkweinstein/   The information contained in this podcast is intended for educational purposes only and is not individual tax advice. Please consult a qualified professional before implementing anything you learn.
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Jun 23, 2025 • 10min

The Role of an Owner at $1M, $10M, and Beyond

In this episode, we dive into what it truly takes to scale your business to $1 million, $5 million, $10 million, and beyond. From building and relying on a capable team to evolving your role from a doer to a visionary leader, we cover the necessary steps and mindset shifts required for substantial growth. I'll also share practical advice on managing your calendar, focusing on strategic objectives, and creating a plan B for every major role in your company—including your own. Tune in to learn how to allocate your resources wisely, communicate your vision effectively, and ensure your business thrives without your constant involvement. Check out the show notes for more information on our Power Sessions and how we can create a profit plan that aligns with your personal goals for a successful 2025.   What You'll hear in this episode: [00:45] The Evolution of a Business Owner [02:15] Building Teams and Systems [03:20] Shifting to a Visionary Role [04:25] Balancing Involvement and Delegation [06:00] Practical Steps to Evolve as an Owner [07:50] Preparing for Contingencies   If you like this episode, check out: How to Scale Without Losing Margin Build Like You're Selling Stop Waiting and Start Scaling with Sam Vander Wielen   Want to learn more so you can earn more?  Visit keepwhatyouearn.com to dive deeper on our episodes  Visit keepwhatyouearncfo.com to work with Shannon and her team  Watch this episode and more here: https://www.youtube.com/channel/UCMlIuZsrllp1Uc_MlhriLvQ  Connect with Shannon on IG: https://www.instagram.com/shannonkweinstein/   The information contained in this podcast is intended for educational purposes only and is not individual tax advice. Please consult a qualified professional before implementing anything you learn.
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Jun 20, 2025 • 13min

When NOT to Sell Your Business

In this episode, I get into the critical topic of when not to sell your business. We’ll explore various scenarios that indicate it's not the right time to exit, including emotional burnout and declining financials. I emphasize the importance of having a business that runs independently of you, and discuss the factors that can impact your business's valuation, such as employee satisfaction and dependency on key clients. Additionally, I highlight the significance of solid financials, properly documented SOPs, and understanding market trends in mergers and acquisitions. Listen in as I provide actionable insights to help you make informed decisions and ensure your business is a valuable asset whether you decide to sell now or in the future. Don't miss out on practical tips to prepare your business for a profitable exit strategy in the years to come.   What You'll hear in this episode: [0:45] Preparing Your Business for Sale [1:35] When Not to Sell Your Business [3:05] Key Considerations Before Selling [4:25] The Importance of Founder Independence [7:35] External and Internal Factors in Selling [9:25] Planning for Post-Exit Life   If you like this episode, check out: Build Like You're Selling When to Get a Business Valuation Done The Steps to Selling a Business   Learn more about our CFO firm and services: https://www.keepwhatyouearn.com/   Connect with Shannon: https://www.linkedin.com/in/shannonweinstein Watch full episodes: https://www.youtube.com/channel/UCMlIuZsrllp1Uc_MlhriLvQ Follow along on IG: https://www.instagram.com/shannonkweinstein/   The information contained in this podcast is intended for educational purposes only and is not individual tax advice. We love enthusiastic action, but please consult a qualified professional before implementing anything you learn.
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Jun 11, 2025 • 10min

Transform Your Idle Cash into Active Profits

In this episode, inspired by my experience at the Junior Achievement Steps for Success program, I dive into different cash management strategies for business owners. I cover the essential functions of checking and savings accounts, the benefits of having multiple accounts, and how to leverage high-yield savings accounts for tax savings. Additionally, I explore the options of investing through corporate brokerage accounts for the long-term growth of excess cash. Remember, while these insights are powerful, it's crucial to consult your financial professional before implementation. Tune in to gain actionable advice and keep your business finances in top shape.   What You'll hear in this episode: [01:05] Understanding Different Bank Accounts [01:35] The Importance of Checking Accounts [02:40] Maximizing Savings Accounts [03:45] Liquidity Explained [05:15] Investing Excess Cash [06:20] Tax Benefits of Brokerage Accounts [07:45] Strategic Cash Management [09:00] Conclusion and Cash Flow Management   If you like this episode, check out: Smart Cash Management for Business Owners Building Value in Your Business While Growing with Jill Simonds Exploring Alternative Investment Strategies with Fred Moskowitz   Want to learn more so you can earn more?  Visit keepwhatyouearn.com to dive deeper on our episodes  Visit keepwhatyouearncfo.com to work with Shannon and her team  Watch this episode and more here: https://www.youtube.com/channel/UCMlIuZsrllp1Uc_MlhriLvQ  Connect with Shannon on IG: https://www.instagram.com/shannonkweinstein/   The information contained in this podcast is intended for educational purposes only and is not individual tax advice. Please consult a qualified professional before implementing anything you learn.
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Jun 9, 2025 • 19min

Shannon's Appearance on The Rainmaker for Contractors Podcast

In this episode, I'm thrilled to reshare an episode from when I was a guest on the Rainmaker for Contractors Podcast. I share practical tax strategies specifically designed for businesses. We'll discuss how recent IRS changes might impact you, the importance of understanding your financial statements, and actionable tips to optimize your tax liability. We'll dig deep into why contractors might avoid their financials and how better cash flow management can drastically improve business health. Grab a notepad and prepare to transform your approach to managing your finances and taxes effectively!   What You'll hear in this episode: [00:45] Guest Introduction: Shannon Weinstein [01:10] Shannon's Background and Career Journey 03:35] Common Financial Mistakes Contractors Make 04:45] Importance of Cash Flow Management [06:15] Proactive Tax Strategies for Business Owners [11:35] IRS Audits and What to Expect [16:25] Onboarding New Clients and Tax Optimization   If you like this episode, check out: Why The Rich Pay No Taxes and You Feel Left Out Why You Need a Financial Storyteller A Cash Flow Reframe You May Need   Check out the Rainmaker for Contractors Podcast https://podcasts.apple.com/us/podcast/rainmaker-for-contractors-podcast/id1547992713   Want to learn more so you can earn more?  Visit keepwhatyouearn.com to dive deeper on our episodes  Visit keepwhatyouearncfo.com to work with Shannon and her team  Watch this episode and more here: https://www.youtube.com/channel/UCMlIuZsrllp1Uc_MlhriLvQ  Connect with Shannon on IG: https://www.instagram.com/shannonkweinstein/   The information contained in this podcast is intended for educational purposes only and is not individual tax advice. Please consult a qualified professional before implementing anything you learn.
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Jun 6, 2025 • 16min

From Founder-Led Sales to Sales Machine

In this episode I dive into the often overlooked topic of founder-led sales. I discuss the common struggle many business owners face in handling various roles, especially holding onto the sales process for too long. I highlight the importance of delegating parts of the sales process, such as discovery calls and lead generation, to create a more scalable and efficient sales machine. I emphasize the need for documented, repeatable processes, clear client qualification guidelines, and the use of enablement materials. Additionally, I provide actionable insights on setting achievable sales goals, tracking key metrics through a CRM, and gradually transitioning to a role of sales coach while hiring sales reps. This episode is filled with practical advice to help you refine your sales strategy and overcome the bottlenecks that hinder your business growth.   What You'll hear in this episode: [00:45] The Importance of Sales in Business [01:20] Challenges of Founder-Led Sales [02:10] Outsourcing and Delegating Sales Processes [04:45] Creating a Scalable Sales Machine [07:00] Setting Sales Goals and Metrics [08:45] Transitioning Out of the Sales Process [11:05] Leveraging Technology and Personal Touch in Sales [12:55] Incentives and Forecasting for Sales Teams   If you like this episode, check out: Increase Your Earnings Without the Sales Struggle Sales Conversations That Convert with Nikki Rausch Stop Waiting and Start Scaling with Sam Vander Wielen   Want to learn more so you can earn more?  Visit keepwhatyouearn.com to dive deeper on our episodes  Visit keepwhatyouearncfo.com to work with Shannon and her team  Watch this episode and more here: https://www.youtube.com/channel/UCMlIuZsrllp1Uc_MlhriLvQ  Connect with Shannon on IG: https://www.instagram.com/shannonkweinstein/   The information contained in this podcast is intended for educational purposes only and is not individual tax advice. Please consult a qualified professional before implementing anything you learn.
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Jun 4, 2025 • 16min

Employee Incentives for Growth-Stage Companies

In this episode I discuss the significance of aligning employee compensation with desired behaviors and business outcomes. Learn practical tips on implementing incentive-based compensation plans, such as cash bonuses, periodic performance reviews, and the concept of phantom equity. Understand why giving away equity isn't always the best solution for fostering an ownership mindset and explore alternative methods to motivate and reward your team. Tune in to discover how to create a compensation plan that truly drives performance and enhances employee satisfaction.   What You'll hear in this episode: [00:45] The Importance of Incentive-Based Compensation [02:00] Real-Time Rewards and Spot Bonuses [03:30] Flexible Performance Reviews and Bonuses [05:35] Creative Bonus Structures [06:58] The Misconception of Equity as Incentive [09:40] Phantom Equity: A Smart Alternative [10:45] Optimizing Compensation Plans   If you like this episode, check out: Creative Benefits You Can Offer Employees Crafting a Profit Plan That Drives Your Business Forward Unlocking Business Success: Mastering the Art of the Accountable Plan   Want to learn more so you can earn more?  Visit keepwhatyouearn.com to dive deeper on our episodes  Visit keepwhatyouearncfo.com to work with Shannon and her team  Watch this episode and more here: https://www.youtube.com/channel/UCMlIuZsrllp1Uc_MlhriLvQ  Connect with Shannon on IG: https://www.instagram.com/shannonkweinstein/   The information contained in this podcast is intended for educational purposes only and is not individual tax advice. Please consult a qualified professional before implementing anything you learn.
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Jun 2, 2025 • 10min

How to 10X Your Strategic Capacity as a CEO

In this episode, we expand on the $5 million bottleneck and discuss how to multiply your strategic capacity as a CEO to catalyze your business growth. Tune in as I share tactical insights into delegating decision-making, auditing your calendar, and prioritizing high-impact activities. Discover how to empower your team to make strong decisions, allowing you to focus on strategic vision, relationship building, and your zone of genius. Get ready to transform your business operations and elevate your strategic thinking!   What You'll hear in this episode: [00:45] Expanding Beyond the $5 Million Bottleneck [02:50] Empowering Your Team for Strategic Growth [04:05] Delegating Decisions, Not Tasks [06:50] Prioritizing Impact Over Effort   If you like this episode, check out: What Do Fractional Officers Do? with Jill Simonds Building Value in Your Business While Growing with Jill Simonds The 5 Financial Building Blocks of a Business   Want to learn more so you can earn more?  Visit keepwhatyouearn.com to dive deeper on our episodes  Visit keepwhatyouearncfo.com to work with Shannon and her team  Watch this episode and more here: https://www.youtube.com/channel/UCMlIuZsrllp1Uc_MlhriLvQ  Connect with Shannon on IG: https://www.instagram.com/shannonkweinstein/   The information contained in this podcast is intended for educational purposes only and is not individual tax advice. Please consult a qualified professional before implementing anything you learn.
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May 30, 2025 • 18min

The $5M Bottleneck

In this episode I discuss a common hurdle many business owners face: the $5 million bottleneck. Drawing from my experience as a CFO, I outline how business growth often stalls around this revenue point due to the founder's over-involvement in day-to-day operations. I highlight the importance of developing systems, delegating responsibilities, and creating clear organizational structures to overcome this challenge. Join me as I share actionable strategies to help you scale your business, empower your leadership team, and transition from a reactive to a proactive management style.   What You'll hear in this episode: [00:50] Symptoms of the Bottleneck [03:10] The Importance of Systems and Processes [04:05] Risks of Inconsistent Decision Making [05:05] Breaking Free from the Bottleneck [08:12] Creating Functional Accountability [10:00] Empowering Your Team [12:35] Mindset Shifts for Effective Delegation [14:50] Taking Ownership as a Leader   If you like this episode, check out: Harness the Benefits of an Accountable Plan in Your Business Use This Hack to Hire Financial Experts in Your Business How to Scale Without Losing Margin   Want to learn more so you can earn more?  Visit keepwhatyouearn.com to dive deeper on our episodes  Visit keepwhatyouearncfo.com to work with Shannon and her team  Watch this episode and more here: https://www.youtube.com/channel/UCMlIuZsrllp1Uc_MlhriLvQ  Connect with Shannon on IG: https://www.instagram.com/shannonkweinstein/   The information contained in this podcast is intended for educational purposes only and is not individual tax advice. Please consult a qualified professional before implementing anything you learn.

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