Why Every Business Owner Needs a General Counsel Before They Sell | With Alessa Huber copertina

Why Every Business Owner Needs a General Counsel Before They Sell | With Alessa Huber

Why Every Business Owner Needs a General Counsel Before They Sell | With Alessa Huber

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In this episode of The Price of Civilization, the host sits down with attorney Alessa Huber, Partner of Cooper & Huber, LLP, based out of Long Beach, CA, to unpack what really determines whether a business sells for top dollar or falls apart at the last minute. The conversation covers why "corporate cleanup" matters long before a sale is on the table, how tax structuring decisions can dramatically change what a seller actually keeps, and why having the right legal team in place from the start can be the difference between a smooth 90-day transaction and a deal that unravels after a year of work.Alessa Huber is a corporate and M&A attorney whose background includes six years as a government attorney with the IRS, followed by a shift into tax defense and tax planning work. That combination of courtroom experience and transactional practice gives her a distinct vantage point: she's seen firsthand what holds up in front of the IRS and tax court, and she applies that insight to help business owners structure deals that hold up under scrutiny. Her work spans general counsel services, corporate transactions, and the tax strategy that surrounds major liquidity events like the sale of a business.A recurring theme throughout the episode is the value of specialization the idea that no single attorney can (or should) handle everything a growing business needs, and that a trusted general counsel can help owners find vetted, reliable professionals rather than getting picked apart by every service provider who comes calling. The host shares a cautionary story from early in his career: a $20 million manufacturing business sale that collapsed after buyers discovered a straw man shareholder and books that were never properly cleaned up, a real world example of how quickly a deal can disappear without the right legal groundwork in place.The discussion also digs into one of the most overlooked decisions in ownership buyouts: whether a departing owner is paid through compensation or through their equity stake. That single structuring choice shifts the tax burden significantly, and misunderstanding it is a common and costly mistake. The episode closes with a broader point that applies to almost any business owner: tax planning isn't something to think about the month before a sale closes it starts the day the business opens.In this episode, you'll learn:● Why business owners need a team of specialized attorneys instead of relying on one generalist● How "corporate cleanup" before a sale directly affects the final sale price● What can go wrong when a business isn't properly prepared before going to market● Why unclean books or undisclosed ownership issues can derail a deal, even late in the process● How a general counsel adds value by vetting and referring trusted professionals● The difference in tax treatment between paying a departing owner through compensation versus equity● Why compensation income is taxed at a higher rate and creates a larger burden for the person being bought out● How litigation experience shapes stronger transactional and contract work● Why tax problems are often really planning problems with more available solutions than owners realize● The importance of starting tax and exit planning well before a business sale closes● Why timing a transaction around the calendar year can limit your tax planning optionsIf you found this conversation valuable, be sure to subscribe to The Price of Civilization, leave a review, and share it with a business owner who's thinking about their next big transaction. Connect with Attorney Alessa Huber:Instagram: @alessa_esq & https://www.instagram.com/ch_counsel/LinkedIn: https://www.linkedin.com/in/alessahuberWebsite: https://chcounsel.com/Facebook: https://www.facebook.com/people/ch_counsel/100083981439300/Connect with Pietro CanestrelliInstagram: https://www.instagram.com/ietaxlaw/ Facebook: https://www.facebook.com/ietaxattorney/ LinkedIn:Law Office of Pietro Canestrelli, a Tax Controversy Boutique, APC | LinkedIn Pietro’s Personal LinkedIn: www.linkedin.com/in/pietro-canestrelli-18032a21 Youtube: https://www.youtube.com/@ietaxattorney TikTok: https://www.tiktok.com/@ietaxattorney?_r=1&_t=ZT-976CgcsahYc
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