$40M for a Big Fish in a Small Pond

Nick Telson-Sillett and his co-founder built what you could call “OpenTable for bars and nightclubs” in the UK. 

Instead of chasing the US (the move most founders are told to make), they went big fish, small pond: dominate their home market first. That focus helped them build DesignMyNight into a business that sold for more than $40M. 

In this episode of Built to Sell Radio, Nick shares what happened, so you discover how to: 

• Turn one clear customer frustration into a business idea you can explain fast 

• Choose focus over hype when everyone tells you to chase the biggest market 

• Set a “financial freedom” number and use it to make cleaner decisions 

• Run a sale process without tipping off competitors too early 

• Negotiate an earn-out tied to revenue so the targets stay in your control 

• Plan for the morning after the deal, when your identity gets reset 

Show Notes & Links

Connect with Nick on LinkedIn

horseplay.ventures

Nick’s website

Definitions

Due-Diligence: This is a comprehensive appraisal of a business or investment undertaken before a merger, acquisition, or investment. It seeks to validate the information provided and uncover any potential risks or liabilities.

Earn-out: This is a financing arrangement for the purchase of a business, where the seller must meet certain performance goals before receiving the full purchase price. It reduces the buyer’s risk and aligns the interests of both parties post-acquisition.

Roll Over Investor: A rollover investor, in the context of selling a business, refers to an individual or entity that rolls some of their proceeds from the sale with the buyer. This strategy allows the seller to defer capital gains taxes and potentially leverage their expertise or resources in a new venture.

About Our Guest

Nick Telson-Sillet

Nick Telson-Sillett is a British entrepreneur and co-founder of DesignMyNight, one of the UK’s leading hospitality discovery platforms. Launched in 2011, DesignMyNight grew rapidly by helping people find the best bars, restaurants, and events, and was later acquired by TripAdvisor in 2017.

Following the acquisition, Nick went on to co-found Scape, a venture studio and accelerator that supports early-stage startups through funding, mentorship, and hands-on growth support. Known for his practical, operator-led approach, Nick focuses on building scalable businesses, nurturing founders, and fostering entrepreneurial communities.

Nick is also a speaker and mentor within the startup ecosystem, sharing insights on product, growth, and company building drawn from his own experience as a founder.