Protections for Founder CEOs When Stepping Down to Executive Roles
- Robert Adelson
- 12 hours ago
- 6 min read
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
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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