How Startup CEOs Can Protect Their Interests When Stepping Down to Executive Roles

 

July 2026 Edition

We are now into summer. Hopefully, you and your family had a most enjoyable July 4th / Independence Day holiday this past weekend, celebrating the 250th anniversary of American Independence! and perhaps you might even be able to continue with a further family vacation. Whether cookouts, picnics, clambakes, time at the beach and seashore, or the lakes, swimming, sailing, biking, walking, hiking or out at the golf links or taking in a ballgame at Fenway Park, I hope you and yours are enjoying summer fun.

For me, I am back in the office after a short vacation trip with three friends to Maine. We enjoyed a barn-burner of a ballgame where the Red Sox farm team the AA Portland Sea Dogs, closed a 9–0 deficit to get to 9–8 before losing to the Altoona Drive (farm team of Pittsburgh Pirates) — lots of home runs including a grand slam HR on each side. We also enjoyed great dining, beginning with our first lunch at the Maine Diner in Wells, https://mainediner.com/menu/ , where I enjoyed the “The Jim Nantz” special, hot lobster roll plus a cup of their award-winning Seafood Chowder. Our great dining experiences, continued to our last lunch in Perkins Cove, Ogunquit, where at old favorite Barnacle Billy’s, https://www.barnbilly.com/barnaclebillys-menu I enjoyed a scrumptious 1 -1/2 pound boiled lobster and, with my friend Howie Sholkin, shared a delicious whole-belly friend clams appetizer.

On the local sports scene, it’s been something of a case of bad to worse. The Red Sox after a recent spurt, with their surprising 4-win sweep of the Yankees, and 3-game win sweep of the Angels, are still 8 games below .500 and remain mired in last place. Then, the Celtics surprised us with even worse news — the trade of Jaylen Brown, my favorite Celtics player, a league standout and the team’s 2026 MVP, in a lopsided desperation move, a Mookie Betts-like salary dump, trading Brown within our division to the 76ers. In the words of old Sox announcer Ned Martin, “Mercy!”

On a brighter sports note, I have enjoyed watching and following the World Cup. Across the street from our office building at 101 Federal Street in downtown Boston, there is a great viewing area, with a huge TV screen and seating for 100, surrounded by the food court with 20 eateries at High Street Place Food Hall https://www.highstreetplace.com/ . It was there that I had some fun encounters with inebriated members of the “Tartan Army”, fans of the Scotland World Cup team, many clad in their kilts and even some with their bagpipes, and other fans of Norway who demonstrated their rowing used to rouse their team to success. I’ve also had fun rooting for the host USA team. Until the recent controversy and subpar team performance in our 4–1 loss to Belgium Monday night in Seattle in the Round of 16, this had been one of the best USA men’s team World Cup showing since the first World Cup almost a century ago in 1930 when in a vastly smaller field the US advanced to the semifinals and finished 3rd overall. Sad ending. Even more, I’ve enjoyed rooting for underdog teams from across the Globe, including upsets of great traditional soccer powers, Germany and Netherlands, and the great effort of tiny Cape Verde (Cabo Verde) with the team’s tenacious 40-year old goalkeeper , Josimar José Évora Dias, commonly known as Vozinha. In the classic match of Cape Verde vs Argentina, Vozinha made several excellent saves including a point blank save against Argentine legend Lionel Messi. https://www.youtube.com/watch?v=1amv62-LOoc The Cape Verdeans came from behind to tie 2–2, pushing the Argentines to the brink before finally going down 3–2 in the 15-minute extra time. If you have gotten the chance to watch, hope you too have enjoyed this event.

As for Newsletter items, a week ago, IVYEXEC, the career advancement website published an article I wrote on challenges faced by Founder/CEOs who can become victims of success and what protections you should consider if you or a colleagues faces this dilemma. My July 2026 newsletter also offers two other professional article links, these are to two earlier articles I wrote in items #3 and #4. The first article is on covenants to safeguard non-financial executive pay, when you are taking a job mainly for reasons other than cash or equity compensation, published by CEOWORLD magazine in 2021 but still relevant. The second article discusses benefits, but also potential risks, of Board of Director service by C-level and senior executives, published CEOWORLD magazine in 2019 but also still relevant today. There is also a special offer as item #5, an Executive Issues Law Diagnostic. I hope some of these items might be of benefit… and my best wishes to all for the rest of July!

1. Protections if you face the Founder CEO Dilemma

Are you a victim of your own success? Do you face the “Founder’s Dilemma”: A Founder CEO after a successful launch, now being pushed by the VCs to step aside for a “professional CEO” to lead the scale up to the liquidity event. My new article published a week ago, on July 1, in the IVYEXEC, career advancement website, offers advice and key protections that might benefit you to navigate the shoals of this situation… 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. Contract Covenants to Safeguard Non-Financial Executive Pay

As a CEO, C-level or senior executive, have you ever been paid in ways other than salary, bonus or equity? Sometimes you sacrifice those and even take further risks for “non-financial executive pay.” Those can be assignments in a new field, making key contacts, gaining skills exposure in your industry. My article published by CEOWORLD in May 2021, and still relevant today, gives two examples of a CFO client who wanted to lead his first IPO, and another client who wanted to be a first time CEO, and discusses the special contract covenants I drafted for them and others to safeguard their non-financial executive pay, to give them the best chance to achieve the career advancement for which they were making real financial and family sacrifices… Read the Article Here

4. Executive Service on Corporate Boards of Directors

Are you a CEO or other senior executive who has been offered the opportunity to serve on corporate Boards of Directors in your own company and another company? My article published by CEOWORLD magazine in 2019 but still relevant today, advises on benefits, compensation, potential liabilities and needed protections to put in place for Board service. Read the Article Here

5. 7/2026 Offer: Good until July 24th

This 2-week value-packed offer, is as a way to get introduced to my law work: an Executive Issues Law Diagnostic — this offer is good through 7/24/26. 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.

Legal and Careers Considerations for Executive Board Service

 

February 2026 Executive Employment Law Newsletter

We are now into February and well into Winter.  There has been plenty of  snow and bone chilling cold in Greater Boston and in Upper New England ski country and much of the rest of the country as well. So if you are a winter sports enthusiast, I hope you are enjoying your winter pastimes in skiing, snowboarding, snowshoeing, ice skating, pond hockey or ice fishing or even making snow men or snow ball fights with the kids.  And for those, like me, who prefer the warmth, I hope you will be able to take at least some vacation time to warmer places.

In sports, the big story is that our New England Patriots quest for a record 7th Super Bowl championship came to an end Sunday night. The Seattle Seahawks were the better team and well earned their 2nd NFL title over the Pats 29-13. When he rang the bell to open the game, Malcolm Butler, the Seahawks’ old nemesis reminded Seattle fans of the last second interception Butler made on the 1-yard line, that gave New England the NFL Championship. That was the one other time the two teams met in the finals, in Super Bowl 49 – in Feb 2015, 11 years ago.

Alas, there would be no such Butler / Brady miracle finish two days ago. But for me, much like the ’67 Boston Red Sox, the miracle for New England was just the sheer joy of seeing the Patriots make it to the Super Bowl at all. After the last two 4-13 seasons, a 14-3 season and 2026 Super Bowl appearance was something I never thought was possible when this season opened. This ending certainly seemed impossible after the Pats were 2-2 in their first four games heading into their first big game as huge underdogs against with the Division dominant Bills for an early season showdown in Buffalo.

This past Sunday, the fans of 30 NFL teams wished their teams were there in place of our Pats. Those disappointed include the Chargers, Broncos, and the Bills too all powerful teams the Pats had to defeat to punch their ticket to the Bad Bunny Super Bowl 60. The last of those 2026 playoff wins reminded me of the Pats’ very first Tom Brady led playoff win that led to their even more improbable Super Bowl run, the first of this 21st century. That was the incredible January 2002 snow game, that featured the “tuck rule” and Adam Vinateri’s 45 year field goal to tie the game in white out conditions and the team’s OT win 16-13 over the Raiders in the last game at old Foxboro stadium. (Kicker Viniyeri was also on hand in Sunday introduced as one the 2026 inductees to the NFL Hall of Fane.) Well, the 2026 Pats march to Super Sunday had its own thrilling snow game Playoff victory with Drake Maye and stellar defense enabling the Pats to win 13-10 in the House of Horrors in Denver over the Broncos, something no Pats team was able to achieve in the Brady era.

So hail to Mike Vrable for giving us some wonderful memories from this surprising and most enjoyable season and high hopes for the franchise future moving forward.

As for Newsletter items, last Friday, IVYEXEC career advancement website published an article of mine on career and compensation opportunities for C-level and senior executives in Board of Director service and also pitfalls to watch for and suggested protections.  Further into this February Newsletter, items #3 and #4 are two older articles of mine published in CEOWORLD magazine, the first on negotiating CFO employment agreements, and the second  on navigating around non-compete covenants, and item #5 is a special offer also on advice regarding restrictive covenants.  As always,  I hope some of these items might be of interest and benefit… and my best wishes to all for the rest of February!

1.       Executive Service on Corporate Boards of Directors 

Are you a CEO or other senior executive who has been offered the opportunity to serve on corporate Boards of Directors in your own company and another company? My new article published last Friday, February 6,  by IVYEXEC career advancement website,  advises on career benefits, compensation, potential liabilities and needed protections to put in place for Board service.  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.       Negotiating Your CFO Employment Agreement

If you have a new job offer or employment contract as a CFO or Chief Financial Officer, my article published in  CEOWORLD in 2019, and still relevant, advises on special terms, authority, reliance, equity and executive compensation package, severance and other essential terms to negotiate.  Read the Article Here

4.       Navigating Non-competes & Other Restrictive covenants

Are you a CEO or other senior executive being asked to sign a non-compete or non-solicitation agreement or an NDA in connection with a new position? My article published in  CEOWORLD in 2017, and still relevant, offers insights and techniques to surmount the perils such agreements could pose to your career.  Read the Article Here

5.       2/2026 Offer:  Good until February 24th   

This 2-week value-packed offer, is as a way to get introduced to my law work: an Executive Restrictive Covenants Law Diagnostic – this offer is good through 2/24/26.   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, LLCExecutive 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.

Executive Service on Corporate Boards of Directors – Benefits, Liabilities and Compensation

On February 21, 2019, CEOWorld magazine published an article I wrote on “Executive Service on Corporate Boards of Directors – Benefits, Liabilities and Compensation” The magazine advised me that I can use “Featured in the CEOWOLRD magazine” and the CEOWORLD “Logo” on my website. 

This article is designed for CEOs and other senior executives offered the opportunity to serve on corporate Boards of Directors in your own company and particularly in other companies.

This article discusses the benefits that Board of Director service can offer to an executive to advance his or her career, including the following:

• Stock, options and other compensation that can be quite lucrative,
• Opportunities to network and learn from peers,
• Observation of other organizations manage their affairs,
• New source of information (in your own company or in business generally),
• Source of new contacts to take the next step up the career ladder.

The articles also discusses pitfalls and potential liabilities of Board service including the significant responsibility to oversee management of the business, due diligence expected to review the transactions before it and record those deliberations, and the fiduciary duties Board members owe to the shareholders so it is important to assure proper care and diligence, and also insurance coverage.

To see my full CEOWorld magazine. article, go to LINK:  https://ceoworld.biz/2019/02/21/executive-service-on-corporate-boards-of-directors-benefits-liabilities-and-compensation/

or on my website at https://www.executiveemploymentattorney.com/articles-section/board-of-directors-service/

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.

It is my hope that this article will be helpful to CEOs, other C-Level and senior executives who are offered the opportunity to serve on their own or other corporate boards, and need to pay attention to both benefits and pitfalls of Board service. If you or any colleague of yours has a need in this area, please do reach out to me at radelson@engelschultz.com.

About Robert Adelson, Esq.

Robert Adelson has been a corporate and tax attorney since 1977. He began as an associate at nationally prominent New York City “mega” law firms, first at the Wall Street firm Dewey Ballantine Bushby Palmer & Wood and later at the Park Avenue firm Weil Gotshal & Manges. In 1985, Adelson returned home, where he has since established himself as a respected Boston business attorney. He has attained partner at several small and midsize Boston law firms, most recently at Lawson & Weitzen LLP and then Zimble Brettler LLP, where he was a partner from 1994 to 2004 before becoming a partner at Engel & Schultz LLP.

Joining a board of directors as an executive can be rewarding

Joining a board of directors as an executive can be rewarding, yet has its pitfalls. Boston executive employment attorney Robert Adelson serves the role of an employment advisor to help executives weigh the costs and benefits of joining a board, as well as negotiates their compensation package. The many benefits of joining a board include but are not limited to lucrative stock and options, networking opportunities and access to a new source of information. However, despite these rewarding benefits, an executive who joins a board takes on a large task – one which, if left unfulfilled can expose them to shareholder lawsuits.

In November of 2013, executive Maxwell Vanderburgh* was asked to serve on a board of directors for an outside company, Mr. Vanderburgh’s C-level executive experience, knowledge and day-to-day management made him the perfect man for the position. When making his decision, Mr. Vanderburgh called on executive employment attorney and advisor Robert Adelson to help him advise the position and negotiate his terms. Attorney Adelson expressed the importance of understanding his rights and duties on the board and potential liabilities he could be exposed to. After Mr. Vanderburgh weighed the pros of cons of this position and realized serving on a board would advance his career and be a rewarding experience the two sat down to negotiate. Upon negotiating Maxwell Vanderburgh’s compensation package, Attorney Adelson implemented proper protections to limit risk exposure and negotiate lucrative stock and options. To ensure protection, Attorney Adelson made sure that there was proper liability insurance in place to protect executive Maxwell Vanderburgh in the event of any suit.

When negotiating the executive’s compensation package, Attorney Adelson explained the responsibilities that must be upheld by a board director; most importantly being a director’s fiduciary duty. This duty is comprised of three separate duties: a duty of care, a duty of loyalty and a duty of candor. In short, these duties require the executive to make informed decisions, act in the interest of the organization it is representing and always provide correct information to shareholders.

Executive employment attorney Robert Adelson was able to help and advise CEO Maxwell Vanderburgh on his decision to become a board director. Attorney Adelson also worked with Mr. Vanderburgh, hands on, throughout the stages of negotiation so Mr. Vanderburgh would receive a compensation package that would be rewarding as well as protect him from any potential suit.

If you or one of your colleagues is a CEO or senior executive who is considering taking on a board of director role, I am glad to assist.  Please do reach out to me at radelson@engelschultz.com.