About SaaS ScaleUps: Pearls of Wisdom from Entrepreneurs
SaaS ScaleUps – Pearls of Wisdom from Entrepreneurs is the go-to podcast for B2B SaaS tech founders looking to scale. Hosted by tech entrepreneur, founder, and investor John O’Connell, we dive into fundraising strategies, the power of AI in SaaS, and growth insights from top entrepreneurs. Whether you're securing Series A funding or planning a successful exit, get actionable wisdom from those who’ve been there.
Brought to you by ScaleUp Group—helping B2B SaaS tech scaleups secure Series A funding, co-investing alongside institutional investors and providing post-investment support.
Publisher
John O’Connell, tech entrepreneur, founder, and investor
How to Build a Business That Investors and Acquirers Want, with Deborah Frost
Deborah Frost is a Portfolio Chair, former CEO, Board Mentorand Partner at Scale Up Group.
In this episode John and Deborah discuss entrepreneurship,leadership and scaling. Deborah shares her experiences of building and growing a business, and explores what makes a company investable or acquirable. She highlights the importance of combining strong numbers with a compelling story that gives investors confidence in the founder, leadership team and future of the business. She also stresses the need for robust financial, tax and contractual foundations, trusted professional advisers, and founders who canstep out of the day-to-day, delegate effectively and focus on the bigger picture. As businesses grow, she emphasises the value of surrounding yourself with the right expertise and support to avoid issues that could derail future growth or an acquisition.
The conversation also explores the opportunities andchallenges AI presents for technology businesses, with Deborah highlighting the importance of protecting the value created through expertise, experience, relationships, proprietary data and human judgement. Ultimately, her message to founders is one of perseverance, continuous learning and perspective: successful businesses are rarely built overnight, and the journey requires resilience, support and a willingness to keep evolving. Drawing on her own experiences of navigating uncertainty, leading through change and building a business for the long term, Deborah offers a candid and inspiring reminder that while entrepreneurship is challenging, it can also be one of the most rewarding journeys a leader can take.
10 Sept 2026
Fundraising and Scaling: Both an Art and a Science
Julian Stone is an Investor/Chair/NED dedicated to guidingtechnology entrepreneurs to success, based on multiple exits, as well as a ScaleUp Group Partner.
In this episode John and Julian discuss the lessons he haslearned from building, scaling and exiting technology businesses. Drawing on his experience founding Hummingbird and building Pythagoras, which supportedaround 4,000 clients and delivered 16,000 projects before being acquired by EY, Julian explores the realities of entrepreneurship — from the fear of failure and the importance of having the right people around you, to making difficult product decisions and knowing when it’s time to change direction. He also shares why founders should seek external advice early and recognise that the people and leadership approach that work at one stage of growth may not be right for the next.
John and Julian also discuss the growing impact of AI ontechnology businesses, from product development and go-to-market to HR and customer operations, and why companies raising investment today need a credible AI strategy. Julian highlights the opportunities presented by agentic AI while stressing the importance of data governance and human judgement. The conversation concludes with advice for founders preparing to raise funding, emphasising that fundraising and scaling are both an art and a science —requiring preparation, strong leadership and the ability to build trust with investors, while recognising that founders don’t have to navigate the journey alone.
5 May 2026
The Truth About Scaling Through Enterprise Partnerships with James Bennet MBE
James Bennet MBE is a corporate advisor supporting The Kings Trust, an entrepreneur, a ScaleUp Group Partner and former EY partner.
In this episode John and James unpack the realities ofpartnering with large organisations. While many founders aspire to collaborate with big brands, James explains that these relationships are often slower and more complex than expected. Success starts with understanding incentives—whythe partner would engage, how they generate revenue, and whether the partnership genuinely drives growth. Rather than relying on large firms to create traction, he suggests that businesses often achieve better results by winning customers first and using that demand to attract partners.
The conversation also highlights the importance of product–market fit, focusing on solving real customer pain points, and building trust through empathy, influence, and consistent delivery.
The discussion also explores the evolving role of AI, with James emphasising the need for “trusted AI” supported by clear guardrails and realistic expectations. He notes that while many organisations talk about AI strategy, the real challenge lies in adoption and execution. Across both partnerships and technology, the key message is human-centric: be clear on your goals, understand the motivations of those you work with, and invest in relationships over time. By asking the right questions, aligning expectations, and following through on commitments, businesses can build lasting trust andunlock more meaningful growth opportunities.
Who has been a guest on SaaS ScaleUps: Pearls of Wisdom from Entrepreneurs
Names identified in recent episode analyses. Showing up to five guests.
Giles Fraser
Michael Tobin
Adam de Courcy Ling
Martin Neale
Podcast Authority Score: 14 / 100
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Questions about SaaS ScaleUps: Pearls of Wisdom from Entrepreneurs
Who hosts SaaS ScaleUps: Pearls of Wisdom from Entrepreneurs?
John host the show. Published by John O’Connell, tech entrepreneur, founder, and investor.
How often do new episodes come out?
The show publishes monthly, based on its RSS feed.
Does SaaS ScaleUps: Pearls of Wisdom from Entrepreneurs take guests?
Yes. Guests have been identified in episode analyses.
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