From Hedge Funds to City Hall: Risk, ADHD, and the Making of a Modern Leader

Andy’s journey-from finance to philanthropy to public office-is anything but typical. In this conversation, he reflects on the mindset shifts required to walk away from a lucrative career to take on civic work with no party backing, no salary, and no safety net. He talks openly about how his ADHD has shaped his decision-making, creativity, and drive, and how it’s both helped and hindered him across different environments. With honesty and humour, Andy invites listeners to consider how career reinvention, neurodiversity, and risk-taking aren’t liabilities-but leadership assets in a world that desperately needs fresh thinking.

About Andy Preston

Andy Preston, podcast guest

Former Mayor, Entrepreneur & Policy Reformer

£5.5M+ Raised by CEO Sleepout8,000+ Executives mobilised against homelessnessNational Media TV and radio commentator; Times and Telegraph contributorFormer mayor Middlesbrough civic leadership

Andy Preston is a business leader, philanthropist, and former mayor on a mission to reshape how we think about poverty, community, and leadership. A regular commentator on national TV, Andy presents insights on current affairs and political developments, bringing sharp analysis and frontline experience to public conversations.

With a track record of launching initiatives that create real, measurable change, Andy brings energy and clarity to discussions around civic leadership, social impact, and the future of local economies.

The charities Andy has founded and led—including the one he continues to run—have raised over £12 million to date, funding projects that tackle homelessness, support vulnerable communities, and drive educational outcomes. As the founder of CEO Sleepout, a UK-wide charity addressing homelessness through business-led action, Andy has mobilised thousands of executives to step up—literally sleeping outside to raise awareness and funds. He offers sharp, contrarian insights into why traditional charity models often fall short, and what it really takes to activate meaningful giving in corporate spaces.

Andy also brings bold views on political leadership from his time as Mayor of Middlesbrough, where he disrupted outdated systems and refused a salary to prove his commitment. He shares what he learned from fighting entrenched bureaucracy, working with limited budgets, and standing up to political tribalism in service of local people.

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