Building businesses with heart: when entrepreneurship meets emotional change

In this World Entrepreneur Day exclusive episode, Kate is joined by Pip Wilson, CEO and Co-founder of amicable, and Ruth Handcock, CEO of Octopus Money, to explore what happens when entrepreneurship meets emotional change - and how building businesses around separation, money and human kindness can transform lives.

Both companies share the same values around challenging the status quo and building meaningful change for their customers, which is why Octopus Money chose to back amicable in 2023.

Building businesses with heart: when entrepreneurship meets emotional change

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About the episode

Pip starts by sharing what sparked the idea to co-found amicable and change the way people divorce. We’ll hear why Ruth and Octopus Money chose to back amicable and how this aligned with Octopus’ goals. Pip, Kate and Ruth all talk about how values like kindness, resilience and emotional intelligence shape meaningful companies, and dig into the link between money and separation, the myths that hold people back and what it really takes to disrupt an industry.

Kate, Ruth and Pip finish with practical and emotional tips for anyone going through a separation - and advice for budding entrepreneurs ready to build something that matters.

A summary of what we cover

• Pip’s reasons for starting amicable
• Why Ruth and Octopus Money backed amicable
• How human values can help companies disrupt industries
• The often-missed connection between finances and separation

About our guest

Pip Wilson is the Co-founder and CEO of amicable, where she leads the charge in transforming the divorce and separation process. A highly successful tech entrepreneur, director and start-up mentor, Pip takes overall responsibility for driving amicable forward, including defining its innovative tech strategy to automate and improve the end-to-end journey, making amicable the kindest and best way to divorce or separate.

Her entrepreneurial journey includes co-founding Bluefin Solutions, an SAP consultancy, which she successfully exited to Mindtree in 2015. Beyond amicable, Pip is a proactive angel investor, actively supporting and promoting female-led businesses. She has also contributed significantly to philanthropy, having served as a trustee for multiple charities including as Deputy Chair of the RSA.

Ruth Handcock is the CEO of Octopus Money, a money advice brand for everyone. She believes everyone should be able to get help with their money, regardless of how much they earn or are able to invest and was awarded an OBE for services to financial services and investments in 2025. Ruth has been part of the Octopus Group – famous for its role in backing Octopus Energy – since 2018. Before Octopus Money, she was CEO of Octopus Investments, an asset manager with £13bn under management. She sits on the Octopus Group Board. Ruth has had more work lives than an octopus has tentacles: her career has spanned roles that have included zoology, strategic consultancy, finance director for Barcardi’s Martini & Cognac portfolios, founding employee of a challenger bank and working in Sierra Leone for the Ministry of Trade. Ruth currently serves as a non-executive director of Aldermore Bank. As a state-school educated kid from Lincolnshire, Ruth is passionate about social mobility. She was Governor at Bolingbroke Academy, a non-selective state secondary school for 6 years. Ruth is saving for a trip to Antarctica to satisfy her scientific roots.

More resources

Learn more about Octopus Money and book a free starter session with a money coach on their website.

You can also get in touch with amicable for more information on the legal, financial and parenting aspects of separation. Book a free 15-minute consultation with an amicable expert today.

We'd love to know how we can help you further. Share your questions on divorce, separation and co-parenting with us at [email protected] . They might just be the topic of a future episode!