The Law By Leo Podcast

*Law By Leo Podcast* focuses on exploring the legal landscape of emerging industries, featuring in-depth discussions with entrepreneurs, legal experts, and industry leaders. Join us as we delve into the world of high compliance sectors and uncover valuable insights for business growth and success.

Episodes

5 days ago

20 min

Episode Summary: In this episode of The Law by Leo Podcast, host Sean O'Connor is joined by Alex, a legal expert specializing in highly regulated industries, to discuss the recent Supreme Court ruling in Trump v. Slaughter. This landmark decision allows the president to fire the heads of independent agencies at will, overturning nearly a century of precedent. The conversation delves into the historical context of the Humphrey's Executor case, the implications for regulatory stability, and the potential impact on various industries such as finance, telecommunications, and cannabis. Alex provides insights into how businesses can remain agile amidst regulatory uncertainties and offers practical advice for navigating these changes. Listeners will gain a deeper understanding of how this ruling could reshape the regulatory landscape and affect their strategic planning.
Key Timestamps:00:01 – Introduction0:14 – Supreme Court Ruling Overview0:53 – Historical Context: Humphrey's Executor1:54 – Impact on Regulatory Agencies3:32 – Challenges for Regulated Industries4:08 – Trump's Role in the Case5:24 – Agencies Affected by the Ruling6:28 – Industry-Specific Implications7:19 – Business Planning in Uncertain Times9:11 – Cannabis Industry Outlook11:28 – Gambling and Prediction Markets12:08 – Preparing for Regulatory Changes14:39 – Practical Steps for Businesses16:01 – Identifying Regulatory Agencies17:21 – Rapid Fire: Court's Decision and Industry Impact
About the Show: The Law by Leo Podcast is a must-listen for business owners, legal professionals, and anyone interested in the intersection of law and industry. Each episode breaks down complex legal issues with clarity and insight, featuring expert guests who provide practical advice and analysis. The show covers a wide range of topics, from regulatory changes to landmark court decisions, all aimed at helping listeners navigate the legal landscape with confidence. Whether you're a seasoned attorney or a curious entrepreneur, The Law by Leo Podcast offers valuable perspectives on the legal challenges and opportunities that shape today's business environment.

5 days ago

20 min

Oct 13, 2026

23 min

Episode Summary: In this episode of The Law by Leo Podcast, host Sean O'Connor is joined by Alex Leonowicz, a partner at Howard and Howard Attorneys, to dissect the looming $6 billion cannabis industry debt due by 2026. Alex, who has firsthand experience in building and scaling a cannabis company, provides insights into the industry's current financial landscape. They discuss the concept of the "debt wall," its implications for cannabis businesses, and the potential for market consolidation. 
The conversation covers the challenges of refinancing, the impact of state regulations, and the opportunities for acquisitions in this volatile market. Listeners will gain a comprehensive understanding of how these financial dynamics could reshape the cannabis industry and what strategies businesses can employ to navigate this critical period.
Key Timestamps:00:01 – Introduction0:12 – The Cannabis Debt Wall Explained0:48 – Guest Introduction: Alex Leonowicz1:34 – Origins of Cannabis Industry Debt2:22 – Economic Realities of Cannabis Expansion3:42 – State-by-State Cannabis Legalization Status4:29 – Impact of Debt on Market Dynamics5:52 – Challenges with Federal Legalization7:01 – Refinancing Options for Cannabis Companies8:02 – Market Consolidation and M&A Activity10:04 – Rescheduling of Medical Cannabis11:16 – Impact of Rescheduling on Financials12:32 – Dual Licensing and Business Strategy14:53 – Due Diligence in Cannabis M&A17:40 – Who's Buying in the Cannabis Market?20:04 – Predictions for Cannabis Market Survival
About the Show: The Law by Leo Podcast is designed for legal professionals, business owners, and anyone interested in the intersection of law and industry. Each episode features in-depth discussions with experts who provide insights into legal challenges and opportunities across various sectors. 
With a focus on clarity and practical advice, the show aims to equip listeners with the knowledge they need to navigate complex legal landscapes. Whether you're dealing with regulatory issues, business transactions, or industry-specific legal matters, The Law by Leo Podcast offers valuable perspectives to help you succeed.
Visit the website below to learn more: https://lawbyleo.com/

Oct 13, 2026

23 min

Sep 29, 2026

22 min

Episode Summary: In this episode of The Law by Leo Podcast, host Evan welcomes Alex Leonowicz, a partner at Howard and Howard Attorneys, to discuss the intricacies of legal fees and how business owners can manage them effectively. Alex, who has experience both as an attorney and a business owner, shares insights into the broken incentive structures within the legal industry, particularly focusing on the billable hour model. 
He explains the phases of commercial litigation, from initial retainers to trial preparation, and highlights the importance of having a business mindset when navigating legal disputes. Alex also introduces the concept of fractional general counsel as a proactive approach to avoid costly litigation. This episode is essential for business owners looking to understand and control their legal expenses while ensuring effective legal representation.
Key Timestamps:00:01 – Introduction00:09 – The $100,000 Legal Fee Story00:26 – The Broken Incentive Structure in Legal Fees01:18 – The Billable Hour Conflict02:20 – Business Owner's Perspective on Legal Invoices03:24 – Anatomy of a Legal Case06:36 – Emotional Costs of Litigation07:41 – Why Lawyers Don't Advise to Settle08:35 – Mistakes Leading to High Legal Bills10:05 – Challenges in Collecting Judgments11:09 – Getting a Second Legal Opinion12:05 – Controlling Litigation Costs13:03 – Alternative Fee Arrangements14:22 – When to Fire Your Lawyer15:37 – Benefits of Fractional General Counsel17:26 – Mid-Stream Legal Help with FGC18:14 – Cost Comparison: FGC vs. Litigation
About the Show: The Law by Leo Podcast is designed for business owners who want to navigate the legal landscape with confidence and clarity. Each episode breaks down complex legal topics into practical insights, helping listeners make informed decisions that protect their businesses and bottom lines. 
Hosted by legal experts, the show aims to demystify the legal industry, offering strategies and tips to manage legal challenges effectively. Whether you're dealing with contracts, litigation, or regulatory compliance, The Law by Leo Podcast provides the tools and knowledge you need to succeed.
Visit the website below to learn more: https://lawbyleo.com/

Sep 29, 2026

22 min

Sep 15, 2026

21 min

Episode Summary:In this episode of The Law by Leo Podcast, host Evan Mack is joined by Alex Leonowicz, a seasoned corporate attorney and partner at Howard and Howard Attorneys PLLC. Together, they delve into five critical types of contracts that business owners often sign without fully understanding the implications. Alex, drawing from over 13 years of experience, highlights the dangers of clauses like personal guarantees in commercial leases, auto-renewals in software agreements, and indemnification provisions in vendor agreements. 
He also discusses the complexities of independent contractor agreements and the potential legal challenges they pose. Alex shares practical advice on how to renegotiate unfavorable terms and the importance of having tailored legal counsel, such as through a fractional general counsel model, to prevent costly legal issues. This episode equips business owners with the knowledge to safeguard their interests and avoid common contractual pitfalls.
Key Timestamps:00:01 – Introduction00:09 – The Dangers of Commercial Leases01:17 – Options for Bad Lease Agreements02:44 – Software Agreement Pitfalls03:52 – Importance of Reviewing Auto-Renewals04:24 – Vendor Agreement Indemnification05:54 – Real-World Indemnification Example07:10 – Independent Contractor Misclassification08:58 – Consequences of Misclassification10:26 – Non-Compete Injunctions12:07 – Risks of Using Template Contracts13:36 – AI Contracts: A Better Option?14:39 – Benefits of Fractional General Counsel16:32 – ROI of Embedded Legal Counsel17:46 – Steps After Signing a Problematic Contract
About the Show:The Law by Leo Podcast is designed for business owners and entrepreneurs seeking to navigate the complex world of legal contracts and obligations. Each episode features insightful discussions with legal professionals who break down intricate legal concepts into practical advice. 
The show emphasizes clarity and proactive strategies to help listeners protect their businesses from legal pitfalls. Whether you're a seasoned business owner or just starting out, The Law by Leo Podcast equips you with the knowledge to make informed decisions and safeguard your enterprise.
Visit the website below to learn more:https://lawbyleo.com/

Sep 15, 2026

21 min

Sep 1, 2026

20 min

Episode Summary:In this episode of The Law by Leo Podcast, host Lisa Mosbey welcomes Alex Leonowicz, a partner at Howard and Howard Attorneys, PLLC, to discuss the recent reclassification of medical cannabis and FDA-approved marijuana products from Schedule One to Schedule Three under the Controlled Substances Act. Alex, with over 13 years of experience in corporate law and a background in the cannabis industry, breaks down what this change means for businesses. 
The conversation covers the implications for IRS Section 280E, potential retroactive tax relief, and the ongoing challenges with banking and financing in the cannabis sector. Alex also highlights the importance of maintaining separate tracks for medical and recreational operations to optimize tax benefits. This episode is essential for cannabis business owners looking to adapt to regulatory changes and leverage new opportunities for growth.
Key Timestamps:00:01 – Introduction00:12 – Cannabis Reclassification Overview01:30 – DOJ and DEA Actions Explained02:33 – Distinction Between Medical and Recreational Cannabis03:08 – Understanding Schedule One vs. Schedule Three03:50 – Impact of IRS Section 280E05:45 – Retroactive Tax Relief Possibilities06:46 – Tax Strategies for Dual License Operators08:37 – Banking Challenges in the Cannabis Industry10:02 – Potential Effects of the Safer Banking Act13:04 – Institutional Investment Opportunities14:13 – Misconceptions About Legalization16:02 – Upcoming June 29th Hearing17:02 – Immediate Steps for Cannabis Business Owners18:21 – Importance of Fractional General Counsel
About the Show:The Law by Leo Podcast is designed for professionals navigating the complexities of high-compliance industries, with a focus on legal strategies and regulatory insights. Hosted by Lisa Mosbey, the show features expert discussions on topics like cannabis law, corporate compliance, and business growth strategies. 
Each episode aims to equip listeners with practical knowledge to make informed decisions, ensuring they stay ahead in a constantly evolving legal landscape. Whether you're a business owner, attorney, or industry stakeholder, The Law by Leo Podcast delivers valuable content to help you thrive.
Visit the website below to learn more:https://lawbyleo.com/

Sep 1, 2026

20 min

Aug 18, 2026

23 min

Episode Summary:In this episode of The Law By Leo Podcast, host Lisa Mosbey delves into the challenging topic of business partnership breakups with Alex Leonowicz, a seasoned corporate attorney and founder of the podcast. Alex shares his insights from over 13 years in corporate law, discussing common reasons partnerships fail, such as unequal workloads, financial mismanagement, and life changes. He emphasizes the importance of a solid operating agreement, likening it to a business prenup, and details key components like clearly defined roles and buy-sell provisions. Alex also explains complex clauses like shotgun, drag along, and tag along, and offers advice for minority partners. The conversation highlights the need for proactive planning to avoid costly disputes and the benefits of having a fractional general counsel to foresee potential issues. Listeners will gain valuable strategies to protect their business interests and ensure smoother transitions in the event of a partnership dissolution.
Key Timestamps:00:01 – Introduction00:19 – Importance of Planning for Breakups00:43 – Why Business Partnerships Fail01:47 – Common Patterns Leading to Failure03:35 – Timeline for Partnership Cracks04:54 – The Business Prenup: Operating Agreements06:10 – Key Components of a Good Agreement08:41 – Understanding Buy-Sell Agreements09:56 – Shotgun, Drag Along, and Tag Along Clauses11:07 – Valuation Disputes in Partnerships12:28 – Protections for Minority Partners14:07 – Freeze Out and Squeeze Out Tactics15:17 – What Happens When Partnerships Break Down17:21 – Mistakes During Breakups18:44 – Steps for Partnerships Without Agreements20:10 – Benefits of Fractional General Counsel22:01 – Rapid Fire: Partnership Scenarios
About the Show:The Law By Leo Podcast is designed for entrepreneurs, business owners, and legal enthusiasts who want to navigate the complexities of business law with confidence. Hosted by Lisa Mosbey, the show features in-depth discussions with legal professionals who provide practical advice and insights on topics like partnership agreements, compliance, and dispute resolution. With a focus on clarity and actionable strategies, the podcast aims to empower listeners to make informed decisions that protect and grow their businesses. Whether you're starting a new venture or managing an established company, The Law By Leo Podcast offers valuable guidance to help you succeed.
For more information, visit our website:https://lawbyleo.com

Aug 18, 2026

23 min

Aug 4, 2026

17 min

Episode Summary: In this episode of The Law By Leo Podcast, host Sean O'Connor sits down with attorney Alexander Leonowicz, a seasoned business attorney specializing in high compliance industries such as cannabis and gaming. Alexander shares his insights on the complexities businesses face when expanding into new states, using his own experiences in the cannabis industry as a backdrop. 
The discussion highlights the pitfalls of assuming uniformity across state lines, covering critical topics like wage differences, tax liabilities, and non-compete agreements. Alexander emphasizes the importance of understanding each state's unique regulations to avoid costly legal issues. He also introduces the concept of fractional general counsel and the benefits of creating playbooks and contract cheat sheets to streamline operations and ensure compliance. This episode is a must-listen for business owners looking to expand their operations while minimizing legal risks.
Key Timestamps:00:01 – Introduction00:35 – Challenges of State Expansion01:14 – Common Misconceptions in Business Expansion02:09 – Alexander's Cannabis Business Experience03:17 – Wage and Leave Differences Across States04:57 – Non-Compete Agreements in Different Jurisdictions05:49 – Tax Implications of Multi-State Operations07:06 – Understanding Nexus and Its Implications08:32 – Major Mistakes Businesses Make09:27 – Creating Playbooks for Compliance11:20 – Benefits of Fractional General Counsel14:44 – Costs of Non-Compliance and Legal Risks
About the Show: The Law By Leo Podcast is designed for business owners, entrepreneurs, and professionals navigating the complexities of regulated industries. Hosted by attorney Alexander Leonowicz, the podcast offers practical legal insights and strategies to help listeners manage compliance, structure growth, and mitigate risks. Each episode delves into real-world challenges and solutions, providing valuable guidance for those looking to expand their businesses while staying within the bounds of the law. With a focus on clarity and actionable advice, The Law By Leo Podcast is an essential resource for anyone operating in tightly controlled markets.

Aug 4, 2026

17 min

Jul 22, 2026

18 min

Episode Summary:In this episode of The Law by Leo Podcast, host Sean O'Connor sits down with attorney Alexander Leonowicz, a partner at Howard and Howard Attorneys, to explore the evolving legal landscape of psilocybin in Michigan. Alexander, with over 20 years of experience in corporate law and high compliance industries such as cannabis, breaks down the complexities surrounding psilocybin's decriminalization in several Michigan cities. He explains the crucial differences between decriminalization and legalization, highlighting the potential legal pitfalls for consumers and businesses alike. The discussion covers the federal classification of psilocybin, its comparison to cannabis, and the implications for business owners operating in this gray area. Alexander also shares insights into the legislative efforts in Michigan and the role of research in shaping future policies. This episode is essential for anyone interested in the intersection of law, business, and emerging industries, providing listeners with a comprehensive understanding of the current and future legal environment of psilocybin.
Key Timestamps:00:01 – Introduction0:14 – Michigan's Psilocybin Decriminalization1:25 – Current Legal Status in Michigan2:57 – Decriminalization vs. Legalization Explained4:32 – City-Specific Decriminalization5:27 – Federal vs. State Law on Psilocybin6:09 – DEA's Increased Psilocybin Research7:41 – Comparison to Cannabis Legalization9:01 – Michigan Legislative Efforts10:51 – Other States Leading the Charge12:13 – Consumer Considerations and Risks14:14 – Business Risks and Legal Exposure16:00 – Fractional General Counsel Services
About the Show:The Law by Leo Podcast is designed for business owners, entrepreneurs, and legal enthusiasts interested in navigating the complexities of law in emerging industries. Hosted by Sean O'Connor, the show features in-depth discussions with experienced attorneys like Alexander Leonowicz, offering insights into high compliance sectors such as cannabis, psilocybin, and other regulated markets. The podcast aims to demystify legal challenges and provide actionable advice, ensuring listeners are well-equipped to make informed decisions. With a focus on clarity and practical solutions, The Law by Leo Podcast is your go-to resource for understanding the legal landscape in today's dynamic business environment.

Jul 22, 2026

18 min

Jul 7, 2026

18 min

Episode Summary:In this episode of The Law By Leo Podcast, host Leann Lyon sits down with Attorney Alexander Leonowicz, a seasoned business attorney and founder of Law By Leo, to explore the concept of fractional general counsel. Alexander shares insights from his extensive experience in regulated industries such as cannabis and gaming, discussing how being a business operator has shaped his legal perspective. The conversation delves into the evolving role of general counsel, the benefits of flat fee structures over traditional hourly billing, and the critical first 30 days when a company hires a fractional general counsel. Alexander emphasizes the importance of legal strategy in high compliance industries and offers practical advice for business owners considering this innovative approach. Listeners will gain valuable knowledge on how to integrate legal services into their business operations effectively, ensuring both compliance and growth.
Key Timestamps:00:01 – Introduction00:42 – Understanding Fractional General Counsel01:10 – Lessons Learned as a Business Operator02:11 – The Modern General Counsel Role03:10 – Challenges in High Compliance Industries04:31 – The Rise of Fractional General Counsel05:05 – Why Flat Fees Are Gaining Popularity06:49 – Initial Steps with Fractional General Counsel08:29 – Common Legal Mistakes by Founders10:01 – The Importance of Contract Management11:48 – Legal Risks in Regulated Industries13:40 – Assessing Your Business's Legal Needs15:22 – Future of Legal Industry and AI
About the Show:The Law By Leo Podcast is dedicated to helping business owners and entrepreneurs navigate the complex world of legal compliance and strategy. Hosted by Leann Lyon, the show features in-depth discussions with legal experts, offering insights into various legal challenges and solutions. Whether you're in a high compliance industry or a traditional business setting, this podcast provides practical advice and innovative strategies to help you stay ahead of the curve. With a focus on clarity and actionable insights, The Law By Leo Podcast is your go-to resource for understanding the legal landscape and making informed decisions for your business.

Jul 7, 2026

18 min

Jun 23, 2026

19 min

Episode Summary:In this episode of The Law by Leo Podcast, host Leann Lyon discusses critical upcoming changes in the hemp and cannabis industry with Alexander Leonowicz, founder of Law by Leo. They delve into the implications of the new federal definition of hemp, set to change on November 12, 2026, which will redefine THC limits per package. Alexander explains how this shift will affect operators, particularly those who have been leveraging the current loopholes in the farm bill. The conversation covers the importance of proactive legal strategies, including inventory management and banking relationships, to prepare for the regulatory changes. Alexander also introduces the fractional general counsel model as a cost-effective solution for businesses needing comprehensive legal oversight without the burden of a full-time legal department. Listeners will gain valuable insights into staying compliant and competitive in a rapidly evolving legal landscape.
Key Timestamps:00:01 – Introduction00:15 – Upcoming Changes in Hemp Definition01:25 – Impact of the Farm Bill Loophole02:28 – Federal Definition and Market Impact03:14 – THC Limits Per Package04:10 – Products Affected by New Regulations05:00 – Regulatory Discrepancies Between Hemp and Cannabis06:03 – Preparing for Regulatory Changes07:12 – Banking and Inventory Management09:03 – Adapting Products to New Regulations10:07 – Importance of Proactive Legal Strategy11:32 – Navigating Federal and State Regulations14:24 – Fractional General Counsel Model
About the Show:The Law by Leo Podcast is a podcast dedicated to helping businesses navigate the complex legal landscape of high compliance industries such as cannabis, gaming, and more. Hosted by legal experts, the show offers insightful discussions on regulatory changes, legal strategies, and compliance best practices. Designed for business owners, legal professionals, and industry stakeholders, the podcast aims to provide clarity and guidance in an ever-evolving legal environment. With a focus on proactive legal planning and strategic growth, The Law by Leo Podcast empowers listeners to make informed decisions and stay ahead of the curve.

Jun 23, 2026

19 min

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