Executive Equity Compensation in a Pre-IPO Company

November 2025 Edition

We are now well into Autumn.  Despite some days of Indian Summer, there is now an increasing chill to our days, with Thanksgiving not too far off at the end of this month.

On the sports scene, one could not but marvel at the exiting MLB World Series concluded just after midnight this past Saturday night. I was rooting for the AL’s Toronto Blue Jays who had not been to the Fall Classic in more than 30 years, but it was hard for me to root against NL’s LA Dodgers with their Manager being former Red Sox player Dave Roberts.  I was at Fenway Park that fateful October night 21 years ago for the ALCS game 4 vs the Yankees. In my mind’s eye, I can still see Roberts taking huge leads from first and then his dramatic steal of second base against Mariano Rivera to spark the greatest comeback in MLB post-season history that led Boston to the 2004 World Series title, our first in 86 years.  But what a Dodgers-Blue Jays World Series game 7 this past Saturday night!  The sight for me, was indelible: Dodgers ace starting pitcher Yoshinobu Yamamoto summoned by manager Dave Roberts  from bullpen with the score tied 4-4, one out in the 9th, with two Blue Jays on base. This, after Yamamoto only the night before, had gone 6 innings and 95 pitches to win game 6.   I was just as electrified back in 2001 at the sight also on TV of Randy Johnson coming in 9th inning relief, also on one days’ rest, to win game 7 for the Diamondbacks.  Plus thoughts of other legendary starters on in relief in other 7th games – Walter Johnson 1924, Grover Cleveland Alexander 1926. As for Sat night’s game 7, 9th inning and Yamamoto, after a hit batsman and force play at the plate, THE CATCH, spectacular in deep CF to save the Dodgers who would win in extras after still more heroics.  Yamamoto went 2-plus innings of scoreless relief for his 3rd series win, and was rightly named Series MVP. 

As for our New England sports scene, Sunday was a reality check for our Patriots. The Atlanta Falcons came back but, when needed, the defense got the stops.  As important, after some setbacks, Drake Maye too, did what was needed so the Pats managed a 24-23 win.  This included the critical last first down pass from QB10 to Hunter Henry so the Falcons got no last chance to win. The win streak remains alive, now at five, pushing New England’s record to 7-2.  The team will next go on the road and we remain hopeful. The buzz is back at Foxboro.  It’s not the old “Patriot Way” but rather something new – the highly positive vibe emanating from our 1st year Coach Mike Vrabel.  As for our winter sports teams, both have had their own small streaks both winning and losing.  So, the Bruins are at .500 and the Celtics just below that.  Hopefully, things will continue to look up them in November and December and for BU hockey as well in November. 

As for Newsletter items, two weeks ago, in IVYEXEC career advancement website, published an article of mine, advising on key protections, equity and other terms to seek to best take advantage of the financial opportunity an IPO can present to you. 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 by CEOWORLD magazine, on two separate subjects of interest to C-level and senior executives.  The first discusses an important technique, keeping and using an ace in the hole in your executive contract negotiations.  The second article discusses an important duty or implied covenant in the law that can enable you, even if you are an employee “at will”,  to have a valid enforceable claim against your employer to be made whole for what you earned and were deprived of. 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 November! 

1.   Executive Compensation in a Pre-IPO Company

Is your private company planning for an IPO?  As a C-Level or senior executive, my new article published two week ago, on October 21, in IVYEXEC career advancement website, advises on key protections, equity and other terms to seek to best take advantage of the financial opportunity an IPO can present to you.   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, executive  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.       Using Your Ace in the Hole in Executive Contract Negotiations

Have you ever considered keeping and using an ace in the hole in your executive contract negotiations?  My article published by CEOWORLD magazine a bit over a year ago (Aug. 2024), discusses just that:  how keeping and using an ace in the hole can help you in negotiations over executive contacts, including job offers, employment agreements, separation agreements and contracts for consulting.   Read the Article Here

 4.   “Good Faith & Fair Dealing” Duty that can safeguard your earnings

As a C-level or senior executive, do you face now or have you ever faced employment termination or other employer action to prevent you from receiving a bonus, stock vesting or other benefit you earned from your successful achievement of a target objective for the company? My article published by CEOWORLD magazine, in September 2021, and still relevant, discusses an important duty or implied covenant in the law that can enable you, even if you are an employee “at will”,  to have a valid enforceable claim against your employer to be made whole for what you earned and were deprived of.  Read the Article Here

5.       11/2025 Offer: Good through December 1st  

This 4 weeks’ value-packed offer, is as a way to get introduced to my law work: an Executive Employment Separation Law Diagnostic  – this offer is good through Mon. 12/1/25.   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
LinkedIn: https://www.linkedin.com/in/robert-adelson-b8a1557/
Blog:  https://robadelson.wordpress.com/
X:  @AttorneyAdelson

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.

Equity Revesting When Your Company Is Acquired

 

October 2025 Edition

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 9^th 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 2^nd 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 4^th 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
LinkedIn: https://www.linkedin.com/in/robert-adelson-b8a1557/
Blog:  https://robadelson.wordpress.com/
X:  @AttorneyAdelson

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, 19^th Floor, across the street from the pre-2020 offices at One Federal Street, 21^st Floor, in Boston’s Financial District.

May 2025 Executive Employment Law Newsletter

I hope this email finds you and your family in good health.  We are now into May and after April showers, we are still seeing some showers and chilly days but also now seeing the flowers sprout and many more warm days, with ever later sunsets. Still too early for the beach, but great for biking, hiking, boating, golf, picnics and enjoying the out of doors. 

This has also been a good time for Boston’ s professional sports scene.  Using the no. 4 pick in the NFL draft, the Patriots under new head coach Mike Vrabel appear to have drafted some quality players that hopefully in the next season will move them closer to a return to the  NFL playoffs and again contending for the Super Bowl.  And the Celtics our remaining winter sports team still playing, passed their first test vs. the Magic and gained some needed rest for their next round challenge with the NY Knicks.  I can’t remember that last time it was Boston vs NYC in the basketball playoffs – should be a dandy with Tatum, Brown and rest of our C’s hopefully prevailing and continuing on their road to a return to the NBA Finals and a shot at Banner #19.   And then finally, there are the recovering Boston Red Sox.  Despite recent bullpen collapses losses, the club remains over .500, with strong contributions by the four newcomers – 3B Bregman, 2B Campbell and pitchers Crochet and Buehler. The Sox schedule opened easy and hopefully the Crimson Hose can meet the challenge as the schedule gets harder in May and beyond.  “Keep your Sox on!” *grinz*

As for Newsletter items, this past week, on May 1, CEOWORLD magazine published my article for CEOs, C-level and senior executives, who have faced or may face an “Executive Bait & Switch.” That happens  where the executive is intensely recruited for critical company needs, the executive delivers on all or most of what the company seeks, and then, is promptly fired when no longer needed as much.  The article suggests the Unjust Enrichment claim with its powerful disgorgement remedy, as means for you to fight back against this pernicious employer practice, that, sadly, I see occurring all too against my C-level executive clients.

Newsletter Item #2, is also a recent item, primarily the text of a short oration I delivered on May 3, that featured a tale of, and tribute to, journalistic integrity as part of the 55th anniversary of my college paper, The Daily Free Press, the independent student newspaper at Boston University.  This newsletter also has links, in items #4 and #5, to two other earlier articles of mine, the first on the merits of RSUs vs stock options as a structure for executive equity, the second on negotiations over CMO – Chief Marketing Officer employment offers and contracts, both published in recent years by IVYEXEC, the career advancement website. There is also a special offer as item #6.  I hope some of these items might be of benefit… and my best wishes to all for the rest of May! 😊

1.       Using Unjust Enrichment Claim to Fight Back Executive Bait & Switch

Have you been a victim of, or do you fear you may become the victim of, an Executive Bait & Switch?  That is, were you, as a CEO or C-level executive, recruited hard because of the company’s special needs you could fulfill, with the bait for you to join, being important promises to you, most often equity or a profits share, only to be arbitrarily terminated after delivering all or most of what the new company wanted and well short of the promises made to you?  My article, published five days ago in CEOWORLD magazine, offers hope.  My article discusses the Unjust Enrichment claim and the highly potent disgorgement remedy to aid you to fight back against the employer, to attain all or most of (and potentially much more than)  what you were promised and was denied after to you, after you “delivered the goods” for the company.   Read the Article Here

2. DFP 55- Celebrating Independent Student Journalism  

“My story stems from an article I wrote as a FreeP assistant editor two years from the founding, in April 1972.  It was a story that almost killed the Daily Free Press in just our 2nd year of existence.” This was part of my 5-minute oration, three nights ago on May 3,  during the 55th anniversary reception for alums of my college newspaper, The Daily Free Press, the independent student newspaper at Boston University.  In this Newsletter post, I share the text of my oration, which was a tale of, and tribute to, Journalistic Integrity, plus further comments cut due to the evening’s speaking time constraint and other comments relevant to my role as a Board Member of the Massachusetts non-profit corporation that publishes this daily student newspaper. More Details Here

3.       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

4.         Merits of RSUs vs Stock Options in Your Compensation Package 

My article published in 2022, by the career advancement website Ivy Exec, describes how RSUs (Restricted Stock Units) differ from stock and options, how they are taxed differently, and important situations where  RSUs can offer significant financial advantages over stock options or restricted stock as executive equity compensation to CEOs, C-level and senior executives.   Read the Article Here

5.       Negotiating Your CMO Employment Agreement

If you have a new job offer or have or soon will receive a draft employment contract as a CMO or Chief Marketing Officer, my article published by the career advancement website Ivy Exec though dated (2021), remains relevant to  advise you on special terms, authority, reliance, equity, bonus structure, severance and other essential terms to negotiate. Read the Article Here

6.      5/2025 Offer:  Good until May 30th  

This value-packed offer, is as a way to get introduced to my law work: Executive Employee Equity Law Diagnostic – this offer is good for the next 3-plus weeks through 5/30/25.   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
E-mail :  rob@attorneyadelson.com
Blog:  https://robadelson.wordpress.com/
Twitter:  @AttorneyAdelson
LinkedIn: https://www.linkedin.com/in/robert-adelson-b8a1557/
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.

This post was published in https://robadelson.wordpress.com/2025/05/03/may-2025-executive-employment-law-newsletter/

April 2025 Executive Employment Law Newsletter

I hope this email finds you well, that you are enjoying the longer days and later sunsets that beckon the arrival of spring.  In April we will have the Boston Marathon and also “AmRev250”.  So April 19, I hope to get a good viewing spot, to view North Bridge in Concord when Concord, Acton, Bedford and other minutemen reenactors recall the seminal events of April ‘75…. 1775, when the embattled farmers stood and fired the shot heard round the world … yes, the Battle of Lexington and Concord, where it all began.  

Also in April, March Madness continues, with Men’s and Women’s Basketball and Men’s Ice Hockey now down the Finals.  

In men’s basketball, my two Division I alma maters Northwestern and Boston University did not make the tournament, and all no. 1 teams are in Final Four.  No Cinderella teams in the Finals this year. 🙁 But best of luck to all, if your alma mater is still in contention or if you are still in the money with your brackets. 

In Men’s Hockey, a large contingent of Hockey East and Eastern teams contended, but only Boston University  survived to the Frozen Four with a thrilling 3-2 overtime win, last Saturday night, over ancient rival Cornell.  Congrats to Coach Jay Pandolfo:  he’s coached three years, and, in all three, his BU teams have gone to the Frozen Four.  I attended the Frozen Four in Tampa (2023) and St. Paul (2024) but cannot go to 2025 in St. Louis.  We lost those two times, and it is still my hope this 3rd time in a row, will be the charm – good luck Terriers! 

And in  professional sports, one of Boston’s winter teams will both soon start the playoffs.  The Bruins had a awful March (3-11) and will finish their season April 15 far from playoff contention. But the Celtics, happily, have gone in opposite direction.  With a record of 13-1 in March through March 30, we can hope the C’s stay hot as they seek to repeat as NBA champions despite stiff competition.  Despite recent losses we also start the Red Sox season with high hopes after several acquisitions in the off season.  I do look forward to attending Opening Day at Fenway this Friday, with an opening day first:  the Sox will host their frequent past World Series season opponents,  the NL’s formidable St. Louis Cardinals!

As for Newsletter items, last week, IVYEXEC career advancement website published an article of mine on using QSBS to potentially shield from taxation  up to $10 million in gains on executive and angel investor stock. 

Further into this April  Newsletter, item #3 is an older article of mine,  published in CEOWORLD magazine, reposted today, around the time of April Opening Day around the Major Leagues, offers an especially grim and powerful example of misalignment in incentive compensation.  In that case example, incentive compensation misalignment of a baseball team’s  ace starting pitcher sparked the worst episode in Major League Baseball’s almost 150-year history (since the founding of the National League in 1876).  In that infamous episode, the “Black Sox Scandal”, the American League champions, the favored Chicago White Sox, played to lose the World Series.  Star White Sox players accepted cash bribes from Boston and New York based gamblers to “fix” the 1919 World Series in favor of the underdog Cincinnati Reds.  Amid the public uproar, and the grave threat posed to the future of the sport itself, in 1920, the MLB team owners appointed the first-ever  Commissioner of Baseball.  Despite Illinois court cases and acquittals of all the accused players, that new Commissioner delivered baseball’s own verdict. Commissioner Landis ruled “8 Men Out” – the accused eight professional ballplayers were barred from baseball, each of the eight accused lost their livelihoods, thrown out of organized baseball …for life…and it all happened due to misalignment.

That 4th  Newsletter item is another older  article of mine published by IVYEXEC,  on startup C-level executive salary, equity and severance terms.

The last Newsletter item, Item #5 is a special offer on negotiation of C-level and senior executive job offers.  As always,  I hope some of these items might be of interest and  benefit… and best wishes to all for the rest of April!  😊 

1.       Achieving Zero Taxation on Sale of Your Appreciated Stock

Are you considering joining an early stage company where stock will be an important part of your compensation package?  My article published ten days ago, on March 21,  by IVYEXEC career advancement website, discusses how proper structuring of your equity grant as qualified small business stock (QSBS), may enable you to have zero Federal taxation on all or most of the appreciation on a sale of shares after 5 years, including several key techniques you might find beneficial… 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.         Protecting yourself against Executive Compensation Misalignment

Are you a C-level or a senior executive with performance compensation based on cliff vesting? Is your performance opportunity subject to discretionary actions of an owner, a Board of Directors or the investors, whose interests might at some point become averse to your own?  That situation – executive compensation misalignment – was the root cause of the biggest scandal in US sports history. Due to that misalignment, star players of the Chicago White Sox fixed the 1919 World Series. That example and others are discussed in my article published by CEOWORLD  Magazine 3/31/2021  to coincide with MLB Opening Day.  My article is reposted now to coincide with the 2025 MLB season, with opening day around the Najor Leagues last Thursday March 27.  In this CEOWORLD article, I also offer ways for you, as executive, to avoid such harmful misalignment in your own executive compensation negotiations.  Read the Article Here

4.       Startup C-Level Executive Salary, Equity and Severance

Are you a senior executive looking to move up to C-level by joining a startup? Being a startup C-level executive can be rewarding in many ways.  But taking that role has many risks too.  My article published in 2023  by the IVYEXEC career advancement website, advises on key protections to negotiate as well as other terms to seek to ensure that  if the startup succeeds, you too will share financially in that success. Read the Article Here

5.      4/2025 Offer:  Good until April 30th  

This 4-week value-packed offer, is as a way to get introduced to my law work: Executive Employment Job Offer Law Diagnostic – this offer is good through 4/30/25.   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
E-mail :  rob@attorneyadelson.com
Blog:  https://robadelson.wordpress.com/
Twitter:  @AttorneyAdelson
LinkedIn: https://www.linkedin.com/in/robert-adelson-b8a1557/
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.

This post was originally published in https://robadelson.wordpress.com/2025/03/29/april-2025-executive-employment-law-newsletter/

March 2025 Executive Employment Law Newsletter

I hope this email finds you and your family in good health.  We are now into March, with this executive employment law newsletter reaching you on March 4th, which date has a place in US history. On this date, on a cool mostly cloudy afternoon in Washington D.C. 92 years ago, March 4, 1933, Franklin Delano Roosevelt took the oath of office to become the 32nd U.S. President.  He told a nation, during some of the worst days of the Great Depression, that the “only thing we have to fear is fear itself”. With his courage, candor, intelligence, and indomitable spirit, he would go on to lead America through those hard days and then through World War II that would follow, as our nation’s longest serving President.  See link – https://www.youtube.com/watch?v=khFwYWWF6Tc

Meanwhile winter continues.  For those like my wife who relishes her winter sports, I do hope there will be sufficient snow and ice this last month of winter.  For those like me who look forward to warmer weather, perhaps you will get a chance to sneak off for time in the sun in warmer places.

March madness will soon begin and to all with your brackets and betting favorites, and for those out there with alma maters in the NCAA Basketball Tournament  – all best of luck! For my two tournament-eligible alma maters, this has not been the best of years, but both still do nurse their slim NCAA Tournament chances. Boston University – with four Patriot League wins in its last five games, the Terriers will host Navy in a first round PL tournament game at the “Roof” this Thursday.  Northwestern, after recent 20-win seasons, has been well below that this season, near the bottom of the 18-team “Big Ten.”  However, with 3 recent Big Ten wins, the Wildcats may finish among the top 15 to at least compete in the Big Ten Conference Tournament, March 12-16 in Indianapolis. So, hoping both BU and NU can stay hot through their respective Conference Tournaments though both are long shots for the 2025 Big Dance.

Meanwhile in men’s college hockey, BU won the Beanpot 4-1 in an upset over BC at TD Garden on Feb. 10, but BC remains firmly no.1 atop the college ice hockey national rankings. Hockey East remains strong with five New England college teams ranked among the top ten in national polls. So perhaps we will see a rare all-Eastern final at the Frozen Four in St. Louis April 10 to 12. All the while, in our professional winter sports, the Bruins are struggling and the Celtics are having a solid season and we can hope both will make the playoffs with a decent playoff run for the Celtics beginning next month. The Celtics will be defending their NBA championship but competition will be stiff.

As for Newsletter items, last week, CEOWORLD magazine published an article of mine on FAQs – my answers to Frequently Asked Questions that I receive on executive compensation, executive equity and negotiations.  Further into this March Newsletter, items #3 and #4 are two older articles of mine, both published in IVYEXEC career advancement website,#3 published in 2022 on leveraging  your strengths in negotiating for key terms in executive retention packages, #4 published in 2023 on terms to negotiate for in your new job offer or employment contract as a Chief Technology Officer (CTO) or a Chief Information Officer (CIO). Item #5 is a special offer also on executive retention. As always,  I hope some of these items might be of interest and  benefit… and my best wishes to all for the rest of March!

1.       Answers to FAQs on Executive Compensation and Equity Packages

My article published a week ago, on Feb. 25, in CEOWORLD magazine, gives answers to a series of frequently asked questions over executive compensation, equity packages and negotiations.  These include when to seek and what to seek for a signing  bonus, how much to seek and how to structure your executive equity, what terms to seek for triggers and benefits in severance, plus my answers to other key questions C-level and senior executives have asked me… questions that you have as well. 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.         Executive Retention Packages – Terms and Negotiations

Do you have now, or Do you soon expect an attractive job offer to leave your CEO or senior executive position?  Is your company “in play”?  Are you nearing a funding milestone?  Are there other reasons why your company has dependence on you and strong desire for you not to leave now.  My article, published in 2022 by IVY EXEC career advancement website, discusses the negotiation and terms for retention agreements in those and other circumstances, where you, as the executive have leverage, and seek to realize important protections and benefits in connection with the company’s need to retain your services.  Read the Article Here

4.       Negotiating terms of Your CTO or CIO Job Offer

If you have a new job offer or employment contract as a Chief Technology Officer (CTO) or a Chief Information Officer (CIO) in a tech or life sciences company or another company involved with the internet or innovation economy, my February 2023  article published in IVYEXEC career advancement website,  advises on terms for authority, interface and support for your position, protection of your own ideas and inventions, compensation, equity and other essential terms to negotiate   Read the Article Here

5.      3/2025 Offer:  Good until March 31st  

This almost 4-weeks value-packed offer, is as a way to get introduced to my law work: Executive Employment Retention Law Diagnostic — this offer is good through 3/31/25.   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
E-mail :  rob@attorneyadelson.com
Blog:  https://robadelson.wordpress.com/
Twitter:  @AttorneyAdelson
LinkedIn: https://www.linkedin.com/in/robert-adelson-b8a1557/
Website: www.executiveemploymentattorney.com

Note on Adelson & Associates, LLC:
*As mentioned in bullet no. 2 of the January 2020 Business Law Newsletter, Robert A. Adelson is now 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.  The new firm’s offices, at 101 Federal Street, 19th Floor, are across the street from the prior offices at One Federal Street, 21st Floor, in Boston’s Financial District.

IP Ownership as Leverage for Founder Equity Negotiations

One week ago yesterday, on Sunday May 28, 2023, CEOWorld magazine published an article I wrote on “IP Ownership as Leverage for Founder Equity Negotiations.”

This new article is designed for CEOs and C-level executives, who are also company founders, who have relinquished control of the company in favor of greater growth but where you now find yourself out-lawyered by investors, ending up with terms that result in loss of much of the equity value you expected to receive and hold.

This article discusses how intellectual property that you developed, that has in the past and continues to form an integral part of your company’s value and identity, and which you my potentially still have ownership claims, can be tapped into and leveraged to protect your interests, rights and distribution share in the success of the company you founded or co-founded, in connection with any of these important events that presage organic changes in the company –

• Significant round of funding,
• IPO — the company’s first public offering or its shares
• Merger, acquisition or sale of significant assets .

For any of those events, if the founder can raise a potential cloud over the company’s title to its core IP, this can provide leverage for an equitable adjustment to assure the owner’s fair share of the proceeds of the success event.

To see my full CEOWORLD magazine. article, go to LINK: https://ceoworld.biz/2023/05/28/ip-ownership-as-leverage-for-founder-equity-negotiations/

Or on my website at https://www.executiveemploymentattorney.com/ip-ownership-as-leverage-for-founder-equity-negotiations/

This was my 42nd article published in CEOWORLD since 2016. Previously, the editor advised that I can use “Featured in the CEOWORLD magazine” and the CEOWORLD “Logo” on my website and add CEOWORLD magazine in my LinkedIn profile’s “Experience Section” as an “Opinion Columnist.” and authority in the field.

On its own initiative, CEOWORLD magazine created on their website a library of Robert Adelson published articles. You can peruse this library and/or read as many of my 41 published articles as you wish. See https://ceoworld.biz/author/robert-adelson/

With more than 12.4+ million-page views, CEOWORLD magazine is the world’s leading business magazine written strictly for CEOs, CFOs, CIOs, senior management executives, business leaders, and high net worth individuals worldwide. https://www.linkedin.com/company/ceomagazine/

It is my hope that this article will be of benefit to CEOs, C-level and senior executives who are company founders and who seek leverage in negotiations after seeing diminished value to your equity position as result of vesting, re-vesting, participating preferred, investor anti-dilution and other investor-friendly terms that have worked to your disadvantage and might have a self-help remedy in IP ownership. If you or any colleague of yours has a need in this area, please do reach out to me @ 617–875–8665 or rob@attorneyadelson.com.