Shark Tank Deals That Fell Apart: The Importance of Due Diligence After the Handshake

Longtime entreVIEW readers will know that my colleague and fellow author, Dan Tenenbaum, has been an avid fan of “Shark Tank” since at least 2014 when he wrote this post. Fans of the show have seen it dozens (or even hundreds) of times: the entrepreneur and the shark shake hands and agree to a deal on national television. Deal done, right…not even close. 

Reportedly, roughly 40-50% of Shark Tank deals made on camera never actually close. A 2016 Forbes analysis found that 73% of deals from the show’s first seven seasons either fell apart or were renegotiated after filming—only 27% closed on the original terms. 

Purchase Price Escrows vs. Holdbacks, An Overview

Recently, I’ve worked on several business sale transactions where the parties expressed varying preferences as to the use of an escrow account versus a holdback mechanism in the transaction structure, so I thought a brief overview of those two concepts might be something that readers of entreVIEW might find interesting.

In a business sale transaction, the parties typically (but not always) opt to incorporate either an escrow account or holdback mechanism, both of which generally serve the same role in any transaction—the parties agree to set aside a portion of the purchase price that a Buyer can recover against, as needed, after the closing. This could be for purchase price adjustment, often related to

The Risks of AI Notetaking

While we heard it here first from our very own Dan Tenenbaum (Keep that Bot Out of Your Boardroom), the New York Times’ recent article, “All Those A.I. Note Takers? They’re Making Lawyers Very Nervous,” underscores—and sharpens—a number of risks that companies should be thinking about before inviting AI notetakers into board meetings, strategy sessions, and everyday corporate discussions.

Described as a “ticking time bomb,” AI notetakers create a near-verbatim, searchable, and durable record of every utterance, off-hand remark, inside joke, and speculative comment made in a meeting. In the abstract, that may sound like good governance. In the context of litigation or regulatory inquiry, it can be deeply problematic.

Bitcoin as Property?

Since we’re all just a little over a week from tax day, I thought I’d share some interesting analysis that was recently published by Nicholas Anthony, a research fellow at Cato Institute’s Center for Monetary and Financial Alternatives. He claims that the rules for capital gains have made it nearly impossible to use Bitcoin as money in the U.S.

Currently, the IRS treats Bitcoin and other virtual currencies as property, not as currency, for federal tax purposes. According to IRS Notice 2014-21, transactions are taxed under general property principles – meaning selling, exchanging,

USPTO’s Adoption of AI to Reduce Pendency in Patent and Trademark Applications

In a prior post back in January 2025, I discussed the potential for increased delays in patent and trademark applications due to numerous factors, including increased filings in both patent and trademark applications, hiring freezes for new examiners, possible reduction in the examiner workforce due to eliminated work-from-home positions, and across the board fee increases. In fact, in 2025, the United States Patent & Trademark Office (USPTO) saw major increases in pendency for both patent and trademark applications. The USPTO, aware of complaints from applicants and IP practitioners, has made concerted attempts to improve efficiency without compromising accuracy and quality. The Office has recently taken numerous steps to improve the application process for new and pending applications by introducing new AI tools developed by the agency to help streamline the process.

Congratulations on forming a company!

You’re creative enough to have an idea that can be brought into commerce and disciplined enough to do the work to get here. You have likely defined your concept, conducted market analysis, created a business plan, and formed a company to both establish a liability shield and help you build value in the enterprise.

So…now what? I’m asked this question often by entrepreneurs, and my answer is simple: use your BRAIN.

What Every Startup Should Know Before Signing Its First Office Lease

For many early stage companies, signing that first office lease feels like a milestone—tangible proof that the idea is becoming a real business. But commercial leases are not like apartment leases. They’re dense, heavily negotiated contracts drafted to favor the landlord, and mistakes made at this stage can follow your company for years. It is important to consider a few key lease provisions before making a decision that can influence the success of your business.