Community wisdom #3
Nick Telson-Sillett: Operator angel investors
Community Wisdom features intimate conversations with accomplished angel investors, distilling their most profound insights into focused stories. Every two weeks, we dive deep into one key lesson that shaped their investment journey.
Meet the investor
Nick Telson-Sillett is the co-founder of trumpet, ideator and first check investor into sequel, and founder of designmynight, which was acquired by the Access Group in 2018. After the exit, Nick began his angel investing journey. Despite his naiveté going into the new space, Nick became instantly hooked. So much so that he’s now made 45+ investments across the UK, US, LATAM, and Africa. Today, Nick splits his time between investor and operator archetypes and we were curious to understand if there’s any hidden advantages to being both an investor and operator. Nick was clear, there’s no hidden advantages. In fact, there are very obvious ones.
The advantages of being an operator and investor
The modus operandi for learning combines experiential practice with shared learning from others. As an investor, you’re primarily learning from others. As an operator and investor, you’re benefiting from both modes of learning. “If you’re only learning through reading, listening, and your investments, you’re probably not learning enough”, argues Nick. Reflecting on his ongoing journey as an angel, Nick expands on how both the investor and operator archetypes reinforce one another - “If you’re no longer an operator, you can quickly fall out of touch with reality on the ground, especially as technology, playbooks, methods, and go-to-market methods evolve”.
Operating in the startup trenches provides asymmetrical information advantages. Financing aside, founders aspire to partner with sparring angels who can have friendly but serious dialogue that goes beyond the surface. Information sourced from analysts, market reports, (prospective) customers, competitors, and alternative products, is not enough. As a concurrent operator, you can bridge the gap between theory and practice through a real-time pulse of the market. You can get deeper and understand the details and nuances that data can often overlook - like the emotional triggers behind a customer’s purchasing decision or the real-world friction caused by a clunky onboarding process.
This heightened awareness of product, technology, and customer trends, enables Nick to share a more accurate and real-time view of the market with his portfolio companies. “I’m facing the same challenges as them, so they know that the advice I give them is very relevant to their journey”. The indirect benefits are also significant. On the ground exposure creates a dynamic feedback loop, where insights aren’t static and constantly being battle-tested against real-time developments. The iterative process leads to more refined judgments and reliable guidance for portfolio companies. So operating in the same space not only sharpens both intuition and analysis but also helps Nick spot trends and outliers more effectively.
The amount of groundwork required to fully understand a startup’s opportunity is cumbersome, and in some instances, you may choose not to proceed with an investment. But Nick has learned that being an operator has enabled him to more easily ask the right questions, and use his insights to understand potential outlier opportunities more quickly. “Investing is tough, and the amount of work needed to be a very good angel investor is a lot higher than I think most people give angels credit for”.
Nick acknowledges that although understanding an opportunity takes a significant investment of time, it’s part of the learning process. Going through the motions, reviewing decks, speaking with founders regularly, and building your own conviction is how you level up as an investor. “With my other commitments as a founder and operating the likes of Pitch Deck podcast and Horseplay Ventures, I realized that the best way to manage my energy was to operate in short, sharp, pre-booked bursts throughout the day”. To manage effectively, he divides his day into focused 30-40 minute blocks for deep work, following principles from Cal Newport's time block planning.
The benefits don’t end there for those functioning in both modalities. His founder-led experience goes beyond sourcing and understanding investment opportunities, and extends to the way he supports his companies post-investment. Post-investment, Nick can continuously validate and monitor portfolio company performance because he’s able to discern what good looks like. The analysis helps with ensuring portfolio companies are meeting or exceeding standards and enables Nick to better diagnose areas where he can be most helpful. His multi-threaded analysis also fuels his own effectiveness as the founder of trumpet as he can exploit a collection of novel startup knowledge.
Fundamentally, it all boils down to the personal relationship that Nick has with his fellow founders having ‘earned the right to advise’ as Vinod Khosla proclaims. He can actually empathise with the evolving needs of his fellow founders, strengthening his emotional and social capital with them, as evident in their reactions - “I earn their trust and respect because they know I’m operating too”.