Business Talk With Chalfin

Hospitality Investing and Growth

In this episode of Business Talk with Chalfin, Bob Chalfin sits down with Kevin Fleming, Co-Founder and Managing Partner of Avenir Hospitality, an investment platform focused on boutique hotels in upscale leisure destinations. Kevin discusses the firm's approach to hospitality investing, the opportunities and challenges of operating boutique hotel properties, and the experience of building a portfolio that currently spans eight properties across three distinct markets. He also shares perspectives from his career in real estate private equity, including his time on the investment team at Whitman Peterson. The conversation explores hospitality as an asset class, the importance of market selection, and the factors that drive long-term success in the boutique hotel space. Kevin is a graduate of The Wharton School, where he earned his MBA, and Pepperdine University, where he received his BA in Economics.

Personal Guarantee Insurance: A Conversation with Brendan Burdette & Ryan Conner

In this episode of Business Talk with Chalfin, Bob Chalfin sits down with Brendan Burdette, Co-Founder & CEO, and Ryan Conner, Co-Founder & President of Braddock Road Insurance, to explore Personal Guarantee Insurance (PGI) — an emerging and innovative form of insurance that allows borrowers to hedge a portion of the risk tied to personal guarantees. As personal guarantees remain a critical — and often daunting — component of small business lending and entrepreneurship through acquisition, Brendan and Ryan unpack how PGI works, why it matters, and how it could reshape access to capital for business owners. Drawing on deep experience across insurance, legal, and regulated industries, they discuss the development of this category-defining product, the regulatory considerations behind it, and the broader impact on lenders, investors, and entrepreneurs. This conversation offers a forward-looking perspective on risk, innovation, and the future of financing — particularly for those navigating the complexities of acquiring or growing a business.

Value Creation in Children’s Dentistry: A Conversation with Amir Fardshisheh

In this episode of Business Talk with Chalfin, Bob Chalfin sits down with Amir Fardshisheh, Co-CEO of Vitana Pediatric & Orthodontic Partners, to explore what true value creation looks like in the world of children’s dentistry. Amir shares insights on scaling pediatric and orthodontic practices, building strong doctor partnerships, and creating long-term enterprise value while maintaining clinical excellence and patient-centered care. The conversation dives into growth strategy, operational discipline, culture, and the unique dynamics of healthcare-focused private equity. Whether you’re a practice owner, investor, or entrepreneur interested in healthcare services, this episode offers a thoughtful look at building sustainable value in a specialized and highly personal industry.

🎙️ Business Talk Brief: Preparing to Meet the Owner

In this Business Talk Brief, attorney and business advisor Bob Chalfin walks through how to prepare for your first meeting with a business owner — what to research in advance, the right questions to ask, and how to approach the conversation strategically and professionally. This short episode highlights common missteps buyers make early in the process and offers practical guidance to help you make a strong first impression while protecting your interests.

Business Talk with Chalfin Brief: Searching for a Business

In this Business Talk Brief, Bob Chalfin explores what to consider when searching for a business to buy — from identifying the right industry and evaluating opportunities, to understanding deal structures and avoiding common legal pitfalls. Whether you’re a first-time buyer or a seasoned entrepreneur exploring acquisition, this short episode delivers practical insights to help you start your search with clarity and confidence.