Equity Revesting When Your Company Is Acquired
- Robert Adelson
- 20 hours ago
- 7 min read
We are now into Autumn with Columbus Day next week (also called Indigenous Peoples Day in Boston) and Halloween the end of this month. Time for foliage viewing, apple picking, raking the leaves, and still lots of outdoor sports, hiking, biking and the like.
Sadly, there will be no further October baseball for our hometown’s beloved Boston Red Sox. Our club did make the post-season but that meant a best of 3 series, played entirely on enemy turf… in THE Bronx. The Yankees prevailed so no post-season games in Boston. Still.. I’m not too disappointed because I thought all along that we were playing with “house money” given the fierce competition we faced just to get that far. Nor am I ready to move on, saying “wait ‘til next year.” Nope, I am still savoring the MLB season we just had. This Sox team led the majors with twelve walk-off wins, and I had the pleasure of seeing the boys notch two of those wins at Fenway in the “walk off greens”. Plus, there were even more games where I did stay through the 9th to see Aroldis Chapman close the game. This Sox reliever (the best we’ve had since 2013’s Koji Uehara) never disappointed. And just as much was enjoying the wonderful exuberance of Chapman’s entrance – To see once again El Tiante smoking up the Fenway skyline, to hear the Latina sounds of “La Reina” Celia Cruz, and view the salsa dancers as Chapman delivers his heat. Please do check it out one more time before we close the book on these BoSox of 2025 – https://www.youtube.com/watch?v=IHYfnJC3uE0
As much as I don’t want to close the chapter on Boston’s Boys of Summer 2025, Boston MLB has now concluded. Yet, as one door closes, a new door opens, and Boston’s sports scene is a lot brighter today than it was a week ago. This past NFL Sunday Night on NBC was a total surprise and joy to watch. I gave the 2-2 Patriots, with their up and down beginning against some of the weakest NFL teams, not a snowball’s chance in Hell of beating the 4-0 Buffalo Bills, on the road, at Orchard Park in Western NY. Facing Josh Allen and the AFC’s top team, incredibly, QB Drake Maye, wide receiver Stefon Diggs, and a stout Pat’s defensive unit, pulled off a huuuuge upset, taking the Bill’s 23-20. At half-time, I was amazed the Pats led 6-3. So, I decided not to go to sleep. Then, we all saw New England rally twice in the 2nd half, with Maye then leading a final drive to set up the 52-yard field goal to win in the last 15 seconds. We are now 5 games into the 17-game NFL season, with the Pats now 3-2. New England would be a wild card entry if the season ended today. With their soft schedule ahead, hopes have now soared that in January, Mike Vrabel’s overachieving NE squad might play (even if briefly) in the NFL playoffs.
Beyond pro sports, there was further good news this past weekend. Saturday night, I also had the pleasure of attending the BU Hockey season opener in a packed Agganis Arena. The Terriers open the season no. 2 in national college hockey rankings. With another strong group led by potential Hobey Baker contenders Cole Eiserman and Cole Hutson (who both scored Saturday night), we can hope that coach Jay Pandolfo can again lead lead the scarlet to our 4th consecutive Frozen Four, this time, in Las Vegas, next April. Opening night fun even continued post-game. My best friend Bob Imperato and I were able to partake in some fascinating opening night story-telling, in the Friends Lounge, when Brian Zive joined our table. Brian amazed us both with a number of fabulous tales from his 30-plus years’ reign as the legendary “Sasquatch” of BU Terrier Hockey . Ol story link - https://www.bu.edu/articles/2015/sasquatch-dog-pound/ That BU Today story was from 2015, ten years ago. At some point The Daily Free Press / Hockey Blog should do an update, the FreePress / Hockey blog’s own feature length Sasquatch story. Such a wonderful man, and Brian has just so much to share with all of us. Anyway, good news for the Terriers Saturday and for the Patriots Sunday: fingers crossed that good news will continue as October goes along.
As for Newsletter items, nine days ago, CEOWORLD magazine published an article of mine, directed to founder CEOs, CTOs and other founder C-level officers, on navigating re-vesting of equity and other perils you are likely to face when your company is being acquired. A link to that new article is featured as item #1. This newsletter also has links, in items #3 and #4, to two other earlier articles of mine both published in IVYEXEC career advancement website, on two separate subjects of interest to C-level and senior executives. The first discusses an important technique, using “QSBS”, to achieve zero taxation if your stock gains are up to the greater of 10x growth or $15 million. The second article is on employment contract terms to seek in negotiations by life science C-level and senior executives. There is also a special offer as item #5. I hope some of these items might be of benefit… and my best wishes to all for the rest of October!
1. Equity Revesting & Other Founder Executive Concerns When Your Company Is Acquired
Are you a founder CEO, or co-founder CTO and other founder executive looking forward to the acquisition of your company? Are you now looking forward to a long-awaited liquidity event? The transaction is certainly good news, but, for you, there are certain risks you ought to know about and plan for. These risks include required re-vesting of your founder shares or your vested equity position, and a potential double trigger barrier to your own liquidity. My article published nine days ago in CEOWORLD magazine offers a roadmap to help you navigate through the potential minefield of these critical issues when your company is to be acquired. This article analyzes these key issues and others from your viewpoint, as founder / C-level executive, and how you can respond to protect yourself while still being supportive to close the deal. Read the Article Here
2. Work with CEOs, C-Suite and Senior Executives, exclusively.
Robert Adelson is an attorney specialized in the representation of CEOs, C-level and senior executives. He no longer represents companies or employers. Learn about Robert Adelson’s work with CEOs, C-level and senior executives to advise on and improve job offers, employment contracts, stock, RSUs, options, bonuses and other executive compensation matters, plus advice and aid on issues of wrongful termination, severance, exit terms, retention, change of control, other executive issues and more … More Details Here
3. Achieving Zero Taxation on Sale of Your Appreciated Stock
Are you the CEO or in senior leadership at an early stage company or are you considering joining an early stage company, in either case, where executive equity is or will be an important part of your executive compensation package? My article published earlier this year, by IVYEXEC career advancement website, discusses how proper structuring of your equity grant can produce a huge cash benefit to you. My article shows how use of qualified small business stock (QSBS), and other key techniques may enable you to have zero Federal taxation on all or most of the appreciation on a sale of shares. Since my article’s publication in March 2025, the 2025 tax law increased the amount that QSBS can shield from taxation to $15 million. Thus, proper use of techniques I share can potentially save you over $3.5 million in capital gains and net investment income taxes you would otherwise have to pay out of pocket. Read the Article Here
4. Employment Contract Terms for Life Science Executives
Whether you have just received a job offer, have a chance to renegotiate your current contract, or are facing a change of control or termination situation, my article published a year ago, in October 2024 by IVYEXEC career advancement website, advises medical device, biotech and other life science executives on the essential terms to negotiate including performance targets and equity geared to the stage of your life science company and its exit goals and key terms for your equity. Read the Article Here
5. 10/2025 Offer: Good through Halloween, Oct. 31th
This 3-plus weeks value-packed offer, is as a way to get introduced to my law work: an Executive Employee Equity Law Diagnostic – this offer is good through 10/31/25. More Details Here
It’s always a pleasure to get back in touch with you and other clients, friends, and colleagues. I hope the links and information provided will be useful to you and that there will be an opportunity for me to work with you on legal matters in the near future.
Let’s keep in touch!
Best regards,
Rob
Robert Adelson
*Adelson & Associates, LLC
Executive Employment Attorney
101 Federal Street, 19th Floor
Boston, MA 02110
(617) 204-5601 Law Firm
(617) 204-5602 Direct
(617) 204-5604 Fax
Email : rob@attorneyadelson.com
Website: www.executiveemploymentattorney.com
Note on Adelson & Associates, LLC:
* Robert A. Adelson is the Principal of Adelson & Associates, LLC. For fifteen (15) years, from October 2004 through December 2019, Robert Adelson practiced law and referred legal work to associates of his, trusted and experienced colleagues, as a partner of Engel & Schultz, LLP. In December 2019, the lead partners of the firm announced they would go into semi-retirement, go their separate ways, and the office lease would expire in January 2020. In response, Robert Adelson formed Adelson & Associates, LLC in December 2019 and commenced the new firm’s operations on January 1, 2020, with the new firm taking over, on that date and going forward, all current Robert Adelson clients, matters and operations, as well as all referral of legal work to associates of Robert Adelson. Since 1/1/2020, the firm’s offices have been and remain at 101 Federal Street, 19th Floor, across the street from the pre-2020 offices at One Federal Street, 21st Floor, in Boston’s Financial District.
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