EPISODE · Aug 21, 2024 · 55 MIN
Nick Telson-Sillett: From Design My Night to Angel Investing… and more!
from Scouting for Growth · host Sabine VdL
On this episode of the Scouting For Growth podcast, Sabine VdL talks to Nick Telson-Sillett, a renowned entrepreneur, angel investor, and public speaker based in London. He has an impressive track record in the startup ecosystem and has made significant contributions to the industry. Today, we will dive deep into Nick's journey as a startup founder and angel investor, and explore his latest project, Trumpet. We'll discuss his strategies for evaluating investment opportunities, his advice for aspiring entrepreneurs, and gain his insights on the current startup landscape. KEY TAKEAWAYS If you just look at the reservation market, you’d think you find an open table at a restaurant, reserve the table, etc. We drilled in a bit further and found the niche of bars that you couldn’t book into in 2012. We went to the industry and pitched the idea of an app like OpenTable that worked for bars, they and the customer base were positive about it, and we went and built the software and signed up all of the best bars in the UK because there was no other app out there that was catering to them at the time. Because we’d built such a flexible booking system for bars, there was a boom in casual dining, which didn’t exist back in the day for experiential, different types of restaurants that needed the flexibility. We then made a play for that niche. Early start-ups: Don’t get distracted. Focus is so important; everyone promises you the world, but partnerships and sponsorships only add noise. Surround yourself with the work; 3 hours in front of my laptop is more worthwhile than going to a founders' event. Becoming a founder has become a fashionable sport; people forget that being a founder is really hard work, building your business, and putting your head down. I love the start-up world. I was mentoring founders, so Angel Investing was an obvious route because I could help financially and mentor the companies I’m financially invested in. A lot of founders I’ve met aren’t investor-ready, and the first thing I say to founders is, " Have you thought about what you want out of your business? If it’s just you and you don’t need to raise money, and if £3m is life-changing to you, you can build a business worth £3m, and you hold 100% of the equity, and then you can sell it. BEST MOMENTS ‘You can’t please everyone: If you build a product and you’re at the whim of your customers, you’ll never have clarity or be able to build strategically, you’ll always be chasing your tail.’ ‘We were the first app to introduce putting your card down or paying a deposit because we found no-shows were a big problem.’ ‘Sales is going to be the new engineering, finding great sales people that know what they’re doing is tough, determine your ICP (ideal customer profile) and go after them specifically.’ ‘Learning to say no to people doesn’t have to be rude; it’s about preserving your time to drive your business forward.’ ABOUT THE GUEST Sillett is a London-based entrepreneur, investor, and public speaker. He is known for co-founding DesignMyNight, a B2C platform that attracted over 8 million views per month and a B2B platform with over 5,000 clients. DesignMyNight was acquired by The Access Group in November 2017 for $30 million. After DesignMyNight's successful exit, Nick Telson-Sillett continued his entrepreneurial journey and co-founded Trumpet, a buyer enablement software solution. He is also the founder of Horseplay Ventures, a venture arm that invests in startups, and has invested in over 55 startups as an angel investor. Nick Telson-Sillett is actively involved in the startup community and has hosted his own podcast called Pitch Deck, where startup founders pitch their businesses to him and guest angel investors/mentors. They discuss the pitch, the business itself, and the investment opportunity. YouTube ABOUT THE HOST Sabine VanderLinden is a corporate strategist turned entrepreneur and the CEO of Alchemy Crew Ventures. She leads venture-client labs that help Fortune 500 companies adopt and scale cutting-edge technologies from global tech ventures. A builder of accelerators, investor, and co-editor of the bestseller The INSURTECH Book, Sabine is known for asking the uncomfortable questions—about AI governance, risk, and trust. On Scouting for Growth, she decodes how real growth happens—where capital, collaboration, and courage meet. If this episode sparked your thinking, follow Sabine VanderLinden on LinkedIn, Twitter, and Instagram for more insights. And if you’re interested in sponsoring the podcast, reach out to the team at [email protected]
What this episode covers
Great startups don’t start with big ideas. They start with small, painful problems that everyone else ignores. In this episode of Scouting for Growth, Sabine VanderLinden sits down with Nick Telson-Sillett—serial entrepreneur, angel investor, and co-founder of DesignMyNight and trumpet—to unpack what it really takes to build, scale, and exit a startup in today’s noisy ecosystem. Nick’s story is a masterclass in focus and timing. DesignMyNight didn’t begin by trying to reinvent dining. Instead, it zoomed in on a neglected niche: bars that couldn’t be booked. In 2012, restaurants had reservation systems—but bars didn’t. Nick and his co-founders validated the pain directly with venues and customers, built a flexible booking platform, and signed up the best bars in the UK before anyone else noticed the opportunity. That flexibility later unlocked something bigger. As casual and experiential dining took off, the same system adapted naturally. What looked like luck was actually deliberate design. The conversation pulls no punches on early-stage reality. Nick is blunt: being a founder has become fashionable—but building a company is still brutally hard. Focus beats networking. Three hours doing the work often beats three hours at a founder event. Distractions—partnership promises, sponsorships, shiny side projects—are usually noise. As an angel investor, Nick brings the same clarity. Many founders, he says, aren’t truly investor-ready—not because of their product, but because they haven’t decided what they want. Not every business needs venture capital. If £3m is life-changing, building a profitable company you fully own and selling it can be the smartest outcome. Optionality starts with self-awareness. Nick also shares sharp insight on product strategy and go-to-market: You can’t please everyone—trying to do so kills clarity Sometimes the most impactful innovation is behavioural, not technical (like introducing deposits to reduce no-shows) Sales is becoming as critical—and as hard to hire for—as engineering Defining your ICP and saying no are leadership skills, not weaknesses The discussion also touches on Nick’s latest venture, trumpet, where he’s applying hard-earned lessons to buyer enablement in B2B—another space full of noise and opportunity. This episode is packed with practical wisdom for: Founders building in crowded markets Operators navigating focus vs. distraction Investors assessing founder readiness Entrepreneurs deciding whether to raise—or not 🎧 If you’re building, investing, or questioning what “success” really means for your startup journey, this episode is essential listening. Because growth doesn’t come from doing more. It comes from doing the right things—consistently and deliberately.
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Nick Telson-Sillett: From Design My Night to Angel Investing… and more!
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