Episodes

In this episode of the Founders & Funding Podcast, Philip chats with Kieran Greene, Founder & CEO of Shinka, an adtech platform powering ultra-fast real-time advertising auctions. Kieran shares his journey as a solo founder from bootstrapping and early debt financing to raising pre-seed and closing a seed round. They discuss how investor expectations change at each stage, building a technical MVP without a co-founder, and why having a clear vision has been critical to Shinka’s growth. A pract...

Philip Smith is joined by angel investor Matthew Stafford, co-founder of Nine Others and founder of Stafford VC. Matthew shares how 9others grew from a simple monthly dinner into a trusted global founder community, why honest peer conversations matter, and how founders can better navigate the challenges of building a company. He also discusses his approach to early-stage investing, what he looks for in founders, and why ideas that start niche or obscure often become the most interesting opportu...

Philip and Frank discuss when bootstrapping makes sense and when it limits ambition, why founders should raise if there’s a real path to $100M ARR, how to think about investors as partners not just capital, what Frank looks for when investing in startups himself and the startups he's invested in including Boardy and Clay, why red oceans don’t matter if you build your own lane and why founders should “engineer for luck” instead of building in silence

Philip and Leroy discuss why co-founder fallouts are one of the biggest causes of startup failure, what bootstrapping really looks like day-to-day, why sales is a non-negotiable skill for founders, how “easy money” can quietly destroy startups, what investors actually respond to (and what they ignore), when to take funding — and when to stop chasing it and much more.