Secret Diary of an angel investor: 15 years investing with Simon Thorpe
- Date
- 2025-11-06
- Host
- Personal
About this event
If you’ve ever wondered what actually goes through an angel investor’s mind before they say yes, no, or not yet, this event gets much closer to the truth than the usual polished startup talk. Secret Diary of an angel investor: 15 years investing with Simon Thorpe is a chance to hear the patterns, judgment calls, lessons, and hard-earned perspective that only come from years of backing early-stage companies and watching what happens next. This is not a generic networking evening built around vague advice. It’s a focused in-person session for people who want a more honest look at how angel investing works in practice: how opportunities are assessed, what founders often miss, where conviction comes from, and how experience changes the way investors make decisions. About the Event At its core, this event is a conversation about decision-making under uncertainty. Over 15 years of investing, Simon Thorpe has seen ideas that looked obvious fail, overlooked opportunities become valuable, and founders surprise investors in both directions. That kind of perspective is difficult to get from surface-level panels or abstract startup content. Expect an event that centers on real insight rather than performance. The title points to exactly what makes the evening interesting: the “secret diary” element. That means getting beyond polished narratives and hearing the observations, instincts, mistakes, and signals that tend to shape investment decisions behind the scenes. Because this is an in-person gathering, the format also matters. It creates space not only to listen, but to ask sharper questions, meet other attendees who care about startups and investing, and continue conversations after the main discussion. The tags around community, networking, meetup, and social suggest an evening designed to be both substantive and genuinely conversational. Whether you come from the founder side, the operator side, or the investor side, the value here is in understanding how long-term investing experience translates into pattern recognition. That perspective can change how you pitch, how you evaluate opportunities, and how you think about risk. What to Expect You should expect a session built around experience rather than theory. The main focus is likely to be Simon Thorpe’s investing journey over the past 15 years, with attention on what has changed, what has stayed consistent, and what the public often misunderstands about angel investing. Topics attendees will likely want to explore include: How early-stage investors evaluate founders and opportunities The signals that build confidence — and the signals that create doubt How investment judgment evolves over time Common mistakes made by founders when raising What makes certain businesses or teams stand out Lessons learned from wins, misses, and surprises Given the meetup and networking focus, you can also expect a more interactive atmosphere than a formal conference talk. That may mean audience questions, informal discussion, and opportunities to compare notes with other founders, angels, operators, and startup-curious attendees in the room. The social element is worth taking seriously. Often, some of the most useful parts of an event like this happen before the session starts or after the main conversation ends: quick introductions, practical advice shared between peers, and conversations that help you place what you heard into your own context. Why Attend If you’re a founder, this event can help you understand the investor lens with more nuance. Not just what investors say they care about, but how they actually think through uncertainty, people, timing, and traction. That understanding can sharpen your fundraising approach and help you communicate your business more effectively. If you’re exploring angel investing yourself, this is a rare chance to learn from someone with a long time horizon. Fifteen years is enough time to build conviction, revise assumptions, and see the full arc of many investment decisions. That makes the lessons more useful than hot takes based on one market cycle. There’s also value in attending simply to become better at judgment. Even if you’re not actively investing, learning how experienced people assess opportunities, weigh incomplete information, and reflect on outcomes can make you better at strategy, hiring, partnerships, and startup decision-making more broadly. You’ll also meet people who are likely asking similar questions: How do good investors separate noise from signal? What do founders underestimate when they raise? How much of investing is analysis, and how much is instinct? What changes after seeing many companies over many years? Practical Details This is an in-person event taking place on Thursday, November 6 at 5:00 PM GMT. If you value being in the room for the discussion and the networking that follows, arriving a little before the start time is the best way to settle in and make the most of the evening. Because the setting is in person, plan for two parts of the experience: the main session and the conversations around it. Come ready not only to listen, but to introduce yourself, ask good questions, and speak with other attendees who share an interest in startups, investing, and the real mechanics of early-stage decision-making. A few ways to prepare: Bring one or two thoughtful questions you genuinely want answered Be ready to describe your work or interest area clearly if you want to network well Think about the lens you’re coming from: founder, investor, operator, or curious observer Stay after the formal discussion if you can, since that’s often where useful connections happen If you want a startup event with more substance than hype, and a chance to hear investing lessons shaped by real time in the market, this is a strong room to be in.
Who should attend
This event will be most useful if you want a more realistic view of startups and early-stage investing, and you value honest perspective over polished talking points. - **You’re a founder** who wants to better understand how angel investors assess opportunities, evaluate risk, and form conviction before writing a check. - **You’re thinking about raising capital**, now or later, and want to hear the kinds of signals investors notice that may not always be said out loud. - **You’re an aspiring or active angel investor** looking to learn from 15 years of investing experience rather than short-term market opinion. - **You work in startups or venture as an operator, advisor, or community builder** and want deeper context on how investment decisions shape company trajectories. - **You enjoy smart, grounded startup conversations** and want to meet other people interested in investing, company building, and practical lessons from the field. - **You prefer in-person events with real discussion and networking** over passive panels or highly scripted presentations. If you want sharper judgment, better questions, and a clearer sense of how experienced investors think, you’ll likely feel at home in this room.