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Grapevine, the travel app for discerning voyagers

Published:  Nov 1, 2019
Noelle Baquiche

Google is overwhelmingly noisy when it comes to travel recommendations; it really has no sense of taste at all. One size does not fit all, especially when it comes to travel. Researching for a city break, you are most likely to come across hotel booking sites and cliched visitor attractions, while all the good stuff is buried deep. This is no use for people who want to get away from all that noise, to enjoy an original travel experience – and to land in that destination prepared with all the best recommendations.

The average person now spends an incredible 10 hours online and visits 38 websites in planning a simple trip. 80% of that time is wasted trying to find the right content, according to Jack Dow, CEO of travel start-up Grapevine, who is on a mission to fix this. Jack has given up a high-flying career in investment, to bring us a powerful new social search tool, where you find unique travel recommendations and can pin high quality discoveries like a scrap book. Perhaps a lovechild between Pinterest and Google Maps, it re-thinks travel search on the web to make planning more visual, with curated recommendations, and the whole search experience much more personal. The platform is ideal for discerning travellers rather than conventional tourists. It certainly saves you time. You can discover great location-based content, or click through to relevant blogs, videos, guides, and user to-do lists linked to your chosen destination, from music venues in Austin Texas, to finding hidden bars in downtown Sydney. When you come across things you like, save them for later. Add them to a to-do list. This makes the best recommendations much easier to check back in on to during your trip, when you need a quick win.

Grapevine’s tech introduces personal profiles, planning tools, scrap-book features, and machine learning to the travel research problem, navigating you to hyper-relevant content, and matching opportunities; whether searching for a romantic weekend in Dublin, or organising dinner for friends in Soho. The secret sauce is linking social recommendations from your friends and wider network, and only connecting you to trusted sources. There is no substitute for human curation, done through crowdsourcing, and augmented through machine learning. Harnessing personal networks and human recommendations is a completely new way to index and scan the web. 

Booking a trip is unique and subjective to each user. Taste matters. Grapevine cross-pollinates, identifying people who enjoy similar tastes; if two matching profiles like a specific restaurant in Paris, for example, you are more likely to enjoy their food recommendations elsewhere. The crowd starts working for you, with relevance determined by soft and social signals, counter to mass popularity. Your profile is learning as you use it, so the quality of search results improves with time. Bringing humans back into the equation promises to deliver much more interesting results. Users further qualify results through tags, like ‘romantic’, ‘hidden’, ‘family friendly’, or ‘foodie’, which helps to eliminate noise – these important terms aren’t often baked into good articles, so Google can’t find the best content. 

Grapevine’s start-up story began in Sydney, with Jack struggling to find fun city recommendations, even though it is one of the most exciting destinations in the world. It didn’t make sense. Search results were failing; a total time sink. Jack knew there must be ways to speed things up, and to get more meaningful results too. So he set about it as a moonlight project initially; collecting friends personal travel recommendations.

It has evolved from bootstrapping this simple idea into a sophisticated tech business, now recommending the best places (for you) globally, to inspire and improve your travel experience. It’s not all about celebrity Instagramers, or plastic influencers either. The users are real people with real insight into the different cities. 

Dow has recruited a top international team to help realise his vision, including the former CIO of Hilton, the ex head of revenue from Time Out, a CTO in Tel Aviv, a Machine learning professor in Moldova, and developers in Uruguay.

To finance the start-up costs, he raised a pre-seed round of £200k for the early product, then a £170k ‘Instant Investment’ round to top this up, managing the whole legal process online, including SEIS approval. Given his investment background, he was well versed in term sheets and the legal jargon, having previously negotiated contracts involving hundreds of millions in value. SeedLegals was a different experience altogether.

“I was blown away by the term sheets and the simplicity of SeedLegals. It was all laid out very well. Options were so easy to understand, and I could easily onboard new investors, and get them to sign [the deal] online.”

The term sheets flow through to the Articles, to the Shareholder Agreement, then on to finalised filings with Companies House – all of this can now be done without the need to engage a lawyer, given the repetitive nature and common needs of start-ups doing investment deals. Acting as an enabling platform for thousands of start-ups, the system is designed to get you through the journey as efficiently as possible.

“Cost wise it is incredibly good value, and as a result, I’ve recommended it to a lot of other entrepreneurs. I’m a big fan. SeedLegals gives you a clear process to manage the transaction. On top of this, we’ve used it for our Advisor Agreements and our Employment Contracts – with next to no push back from anyone.”

As well as walking Founders through each step online, Jack comments, “they are always there and able to answer your if needed” – via instant chat, email or phone. “In fact, their responses to [my] ad hoc questions were brilliant.” Grapevine is once again fundraising now, with all of the documents conveniently housed online in one place, and synchronised as new terms are added round-by-round. His team and investors can access their documents from around the world too, which helps when spread across multiple different continents.


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