In this episode, Ben Burch, co-founder of Allegr, joins host Rob Woodhead from Old Street Labs for a wide-ranging conversation on building products, purpose, and community, without boiling the ocean.
Ben shares his journey from a non-linear career path to founding a mission-driven startup focused on the UK military and veteran community. They dig into why most so-called “social” platforms miss the mark, and what it really takes to design for meaningful, real-world connection.
From navigating go-to-market without big budgets to avoiding common product-building pitfalls, this episode is full of sharp insights for anyone working in tech, community, or purpose-led businesses.
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In this episode of the OSL Podcast, Rob sits down with Nick Sales to unpack what a fractional CTO actually does, how outcome driven retainers work, and why strong product, team, and technical foundations matter for growth stage companies. Nick also shares his non linear journey into consulting and startup advisory, plus his perspective on GenAI, where it shines for prototyping and where it can become risky in production if you do not yet know what good looks like.
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Real stories from the people building tech, founders, designers, consultants & creators. Honest convos. No fluff. Just the human side of innovation.
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Jason Margolin shares how AI is reshaping software development, where “vibe coding” falls short, and how non-technical founders can prototype smarter without a CTO.
