Business owners face a costly tension when planning an eventual exit: the decisions that may shape taxes and deal outcomes often need attention years before a buyer appears, yet the legal language and tax rules can be difficult to understand. Josh Lowenthal joins Craig Andrews to explain why effective advisors should translate complexity into clear choices so owners can make informed decisions about their companies and futures.
Josh distinguishes the perspectives a CPA and a tax lawyer may bring to the same business. CPAs often concentrate on accounting, reporting, compliance, and completed activity, while tax lawyers examine statutes, regulations, entity structures, and proposed transactions. For reorganizations, acquisitions, and exits, these perspectives can work together when advisors stay focused on the owner's goals.
The conversation also explores Qualified Small Business Stock, or QSBS, and why owners may want to investigate it well before a sale. Section 1202 may permit eligible shareholders to exclude some federal gain from qualifying stock, but the requirements are detailed and fact-specific, including rules concerning the company, the shares, business activity, and holding period. Eligibility and tax treatment are not guaranteed, so owners should seek qualified legal and tax advice based on their circumstances.
Josh connects that commitment to clarity with his experience hiking the John Muir Trail alone for roughly three weeks. Moving toward one destination each day created space to be present and reflect. In his legal work, the same preference for simplicity means drafting understandable contracts, reducing ambiguity, and helping clients grasp the consequences of decisions that remain theirs to make.
Want to learn more about Josh Lowenthal's work? Check out his website at http://www.joshualowenthal.com.
Connect with Josh on LinkedIn at https://linkedin.com/in/jlowenthal.
Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.
Want to learn more about Craig Andrews' work at allies4me? Check out his website at https://allies4me.com/.
