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Scouting for Growth

Nick Telson-Sillett: From Design My Night to Angel Investing… and more!

Scouting for Growth

Sabine VanderLinden

Business:entrepreneurship, Business, Entrepreneurship, Technology

4.835 Ratings

🗓️ 21 August 2024

⏱️ 55 minutes

🧾️ Download transcript

Summary

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.

Transcript

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0:00.0

The Welcome back to scouting for growth, the podcast where we explore the journeys of successful

0:22.2

entrepreneurs and investors too. Today we have an exceptional guest joining us. Nick Telson,

0:30.0

Cilat. Nick is a renowned entrepreneur, angel investor and public speaker based in London.

0:35.6

Yes, my city too, he has an impressive track record in the startup ecosystem and has made a significant contribution to the sector or industry.

0:48.0

We are excited to have him here today to share his insights and experiences with us. Nick is the

0:56.2

co-founder of Design My Night, a highly successful B to C platform that quickly gained popularity here in London

1:05.2

attracting over 8 million views per month. The platform also had a B to B arm

1:12.0

serving more than 5,000 clients. I'm sure many of you have probably used

1:16.7

Design My Knight if you have been looking for a bar or a pub and you wanted a unique experience.

1:23.0

Design My Knight's remarkable success story

1:26.2

accumulated in its acquisition by the Access Group in 2017

1:31.4

for approximately $30 million.

1:34.8

After the successful exit of Design My Knight,

1:38.6

Nick continued his entrepreneurial journey by co-founding Trumpet, a buyer-enabled software solution. a

1:45.0

Bower-General Nair-enabled software solution in addition to his ventures is a founder of

1:49.7

Of course play ventures a venture arm that has invested in over 55 startups and has become a well-respected

1:58.0

angel investor.

2:00.0

Nick's expertise and experience in the startup world has made him a thought after speaker.

2:07.0

I mean, Nick shares his knowledge on stage and on digital,

2:15.0

digital, he even hosts his own podcast called Pitch Deck,

2:20.0

where he provides valuable insight to startup founders and

2:24.8

in angel investors as well and how you know one should engage with the other

...

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