In this episode, Michelle Orr of Live Oak Bank shares her decades of experience working in SBA lending and partnering with entrepreneurs looking to acquire businesses. She explains what makes Live Oak’s process unique and her quarterback-style approach from prequalification through closing. Michelle outlines key SBA rules, deal structures, limits, and expectations for both first-time buyers and seasoned acquirers, as well as common red flags such as unstable revenue trends, customer concentration, and heavy seller dependence. She walks listeners through timelines, diligence requirements, and transition planning, emphasizing the importance of proactive communication and building the right team of advisors. Michelle also highlights current SBA updates and why she loves helping buyers navigate the acquisition journey.

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In this episode, trust and estate attorney Michael Clear, Partner of Wiggin and Dana discusses how thoughtful estate planning can help business owners preserve and protect the wealth created through a lifetime of work. He explains the strategic use of trusts—revocable and irrevocable—to minimize estate taxes, provide asset protection, and ensure family continuity. Clear emphasizes the importance of starting planning well before a sale—ideally two or more years in advance—to take advantage of valuation discounts and tax benefits. With a counselor’s mindset, he guides clients through not just the technical but also the personal aspects of planning, helping families clarify goals, communicate effectively, and set up structures that reflect their values and future aspirations.

TRANSISTOR

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In this episode, we sit down with Brad Malicki, an experienced M&A attorney with Halloran Sage to discuss the crucial role legal counsel plays in getting a deal to the finish line. Whether you’re buying or selling, the goal is always the same—negotiate to “yes” and close the deal in a way that works for both sides.

Our guest explains why having the right attorney—one who understands M&A transactions—is essential. From interpreting the Letter of Intent to drafting detailed agreements that prevent future disputes, an experienced M&A attorney knows how to ask the right questions, balance legal protection with deal momentum, and ensure both parties walk away satisfied (if only a little bit happy and a little bit unhappy).

You’ll also hear insights on what differentiates a transactional attorney from a litigator, the importance of clear communication between all parties, and why the best contracts are the ones that get signed, filed, and never need to be revisited.

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In this episode, Deborah sits down with Jason Correia, a Principal at CLA and an expert in Quality of Earnings (QoE) analysis for M&A transactions. Jason breaks down why QoE reports are essential for verifying the accuracy of financials, understanding true cash flow, and normalizing earnings to reflect what a business will really look like under new ownership.

Discussed are key topics like normalizing owner-related expenses, determining net working capital, and how these analyses impact deal value and negotiations. Jason also shares insights from his career journey—from auditing to M&A—and how his team at CLA supports both buyers and sellers through every phase of the transaction.

Tune in to learn how QoE can reveal the real earnings story behind the numbers.

www.claconnect.com

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In this episode, Deborah sits down with Joseph Jaffe—Professional EOS Implementer, Executive Leadership Coach, 6-time author, keynote speaker, and host of Joseph Jaffe is Not Famous and The Entrepreneur’s Journey.

Joseph shares how entrepreneurs can break free from the myth that building a business must be painful. Through the Entrepreneurial Operating System (EOS), he helps leadership teams gain clarity and alignment, instill discipline and accountability, and foster trust and healthy collaboration.

From reframing entrepreneurship as discovery instead of struggle to creating “harmonic resonance” among diverse personalities, Joseph offers insights for leaders who want to build thriving teams and sustainable businesses without accepting dysfunction as the norm.

Jaffe is @jaffejuice on all the major socials.

For all links, please visit

https://linktr.ee/jaffejuice

or

www.eosworldwide.com/joseph-jaffe

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In this episode, we sit down with Jeffrey Rich, one of the three partners at Touchstone, to delve into his journey from a proprietary trader on Wall Street to becoming a key figure in mergers and acquisitions. Jeffrey shares his experiences in the high-stakes world of finance and his transition into the M&A industry, highlighting the emotional and intellectual challenges he faced along the way. He discusses the philosophy behind Touchstone's team approach, the complexities of closing deals, and the factors that influence successful business exits. Jeffrey also reflects on his passion for working with business owners, the importance of thorough pre-market evaluations, and his personal aspirations beyond the financial sector. Tune in to gain valuable insights from a seasoned M&A advisor who is dedicated to helping clients achieve their business goals.

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In this episode, Carlos Salmon shares an inspiring journey from teaching tennis in the Hamptons to breaking into the world of finance. Through chance encounters, determination, and seizing opportunities, he reflects on lessons learned, career growth, and the unexpected turns that shaped his path. A story about ambition, resilience, and following doors that open when you least expect it.

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In this episode, the conversation dives into the world of mergers and acquisitions through the lens of patience, process, and precision. The guest shares lessons on why shortcuts backfire, how attention to detail can make or break success, and what it really takes to achieve the best outcome in business transitions. It’s a candid discussion about discipline, resilience, and the mindset required to navigate big changes.

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In this episode of Touchstone Talks, we sit down with Cosmo to explore his journey transitioning out of his business, 4All Promos. With Touchstone’s guidance, Cosmo found the right partnership to grow his company while giving him the freedom to move into what he calls “pretirement.” The conversation dives into lessons learned as a business owner, the challenges of letting go, and the exciting opportunities that come with redefining retirement.

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Touchstone Talks delivers real-world insights from trusted advisors and professionals to help business owners prepare for the future. Each conversation is designed to guide owners through the key components of a successful exit strategy—always with the goal of maximizing the value of their life’s work. By educating and empowering business owners, we create the foundation for successful transitions and lasting impact.

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