Ventures

Assen Plevneliev, Chief of Staff @ SigmaSquared: What Makes An Incredible Founder


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The best communities aren't built on transactions but on curation and forward-giving.Sigma has 1,000 founders across 35 countries who've raised $2.7B with no fund attached, just genuine connections and support.When you remove commercial incentives, people build deeper relationships that create more value.In this episode, we sit down with Assen Plevneliev, Chief of Staff at Sigma, for an exclusive deep dive into building the world's most selective entrepreneurial community. Discover how this invite-only network of 1,000 founders under 26 has generated over $2.7 billion in funding, why they intentionally rejected the traditional VC model, and the "third door thinking" that separates exceptional founders from the rest.Thank you to the team at Loaft Covent Garden for looking after us! 🎯 On the Docket:00:03:00 - Why personal spaces and authentic conversations trump traditional interview formats00:04:55 - The strategic importance of personal branding for early-stage founders00:07:20 - LinkedIn as the most undervalued platform (and how to win against weaker competition)00:12:10 - Sigma's curation philosophy: why quality trumps growth every time00:16:49 - The controversial decision to abandon their fund model (and why it saved the community)00:21:36 - Inside Sigma's brutal selection process: 500 nominations, less than 100 accepted00:23:58 - "Third door thinking": the resilience trait that predicts founder success00:31:04 - European vs American startup ecosystems: leveraging the talent arbitrage00:38:10 - Advanced networking tactics: why "what do you do?" kills conversations00:42:38 - Operating a 1,000-person community with 60 volunteers and one paid employee00:46:32 - Creating ego-free environments: how Sigma's Global Summit works differently00:51:06 - Scaling challenges and the financial sustainability question00:53:17 - The founder Assen would bet his life on (33% market share in 3 years, bootstrapped)⚡ Key Insights:Why forward-giving communities outperform transactional networks by massive marginsThe "arbitrage opportunity" European founders miss when scaling globallyHow automation can manage 1,200 angel investors with just two peopleThe psychology behind why curation creates exponentially better outcomes than growthWhy most networking advice is backwards (and what actually works)The hidden cost of mixing investment funds with authentic community buildingHow 95% of Sigma's $2.7B in funding happened after members joined the community💬 Notable Quotes:"Any two people we put in a room together should be able to have a great conversation - that's our hypothesis for 1,000 people across 35 countries.""If you want to go fast, go alone. If you want to go far, go with others. But I'd say if you're working with others, you're not only going far, you're going much faster.""The third door is when you've been rejected from the first two, you run around the building, find an open window, jump through it, and you're in the club.""Don't start by asking 'what do you do?' - it shuts the conversation because you're asking someone to pitch what they've pitched 100 times before."📚 Resources Mentioned:The Third Door by Alex BanayanShow Your Work by Austin KleonChatGPT for Developers (prompt engineering course)🔗 Connect with Assen:Sigma CommunityLinkedIn

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VenturesBy Viraj Acharya

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