In this episode of Stake & Soul, Barry speaks with Amy Barry, who sold 75% of her communications agency di:ga into an Employee Ownership Trust in 2023 and completed a careful two-year founder-CEO transition in 2025. A former journalist for The Times and The Mail on Sunday, Amy spent her early career at Oxfam and Global Witness. What began as freelancing from Bristol grew almost accidentally into a 12-person strategic communications agency, working with mission-driven clients including Oxfam, Amnesty International and Chatham House. She now chairs the di:ga board and runs her own strategic coaching and facilitation practice at amybarry.com.
Amy didn’t set out to build a business, let alone an employee-owned one. An unsolicited acquisition approach from a bigger agency was the moment she first realised she had something she could sell and that she didn’t want to sell it to the wrong kind of buyer. A coaching conversation with Simon North, pointed her towards EO as the exit that could protect the mission, the clients and the culture she’d spent twelve years building.
What’s covered in this episode:
- The “accidental entrepreneur” journey from a freelance career in Bristol to a 12-person agency with a non-profit-only client list
- Motherhood as a founding principle: why Amy built flexibility into the agency’s DNA from the start, and how running a business with two small children at home shaped both the decision to sell and the kind of succession she wanted
- Why an unsolicited acquisition approach was the moment Amy realised she had something to sell and that she didn’t want to sell it to the wrong buyer
- How a conversation with coach Simon North, opened the door to employee ownership
- Preparing the senior team two years ahead of the exit and running a deliberately open CEO search “pitting her against the market” so her successor could win it fairly
- Why the first job of a founder planning an EO exit is to make herself “the least important person in the company”
- The identity work of letting go: working with a founder-CEO succession coach, crying through most of the sessions, and not wanting to be a “pain in the neck” exiting founder
- Communicating EO to staff and clients managing fear, misinterpretation and the Google-fuelled expectation that “suddenly everyone gets a say in every decision”
- Opening up financial transparency, the discomfort of disclosing the valuation, and the shift from retrospective quarterly accounts to real-time monthly reporting
- Why Amy kept 25% of the business on her lawyer’s and adviser’s advice and why in hindsight she is really glad she did
- Building a culture of honest, courageous feedback as “a gift”, moderated for different people
- The moment of walking into the office and realising nobody needed her anymore
Quickfire highlights
- Employee ownership is: a natural evolution of the culture we had at di:ga, and therefore the right thing for us
- Biggest EO surprise: how little changed overnight – people were who they were the day after we sold
- Book recommendation: The Eternal Business by Chris Budd – Read in one sitting in the bath before Amy decided to sell plus Matrescence by Lucy Jones as a companion read on identity and transformation
- Confessional: the identity struggle of exiting a business “who am I if I’m not running di:ga? Who am I if people don’t need me?” and why self-work is as important to a successful handover as the legal paperwork
Barry and Amy also touch on the “Ming vase period” of the first post-sale CEO holding deferred consideration, the pressure that comes from suddenly having a valuation and a profit number to live up to, and Amy’s reflection that in a world that doesn’t value parenthood or art enough, finding the right identity on the other side of founder-CEO life is often harder than selling the business.
Follow Stake & Soul and never miss an episode.
Subscribe here to listen on your favourite podcast platform.
The following podcast is intended to be of a general nature, will not be suitable for everyone, and should not be treated as a specific recommendation. We recommend taking professional advice before entering into any obligation or transaction.