5 years ago

A new way to stay: Startup Stay connects galavanting entrepreneurs together with locals

Services that connect travelers to locals have been growing in popularity ever since the launch of CouchSurfing back in 1999. Since then, commerce has been steadily creeping into what was once a middleman-free P2P marketplace.

CouchSurfing has become a for-profit, Airbnb has gained enormous traction, and the “stay with a local” model has become a competitive industry in its own right.

While Airbnb’s Brian Chesky touts a “new consumption model” that has people owning less stuff – including homes – he tiptoes around the issue of the transactional nature of these newly-formed relationships. What was once the pure old-fashioned hospitality of welcoming weary travelers into one’s home with a warm meal has become a revenue stream for thousands of people across the world.

For entrepreneurs looking to stay with locals and build their networks as they travel, the only options have been participating in one of these marketplaces or working traditional networks to make local connections. A new startup aims to take the headaches out of this process by connecting traveling entrepreneurs with their local brethren.

The promise is right there in the name: it’s called Startup Stay, the “entrepreneur’s travel community.”

Combining travel and entrepreneurship – two of the most passionate communities that are also au courant in popular culture, is a smart idea. Dave McClure of 500 Startups has brought the two communities together with Geeks on a Plane, a tour group for entrepreneurs of sorts that focuses more on creating and curating trips for entrepreneurs all over the world.

Startup Stay is more of a fusion between CouchSurfing and LinkedIn.

The idea is that like attracts like, and that both hosting and stay with other entrepreneurs can invigorate ideas, encourage connections, and facilitate cross-pollination across segments and industries. With entrepreneurship as the common thread, the idea mimics the groups and other affinity segmentations on other sites like Airbnb and CouchSurfing.

Startup Stay was the brainchild of co-founder Fred Caballero. Launched in June 2012, the site was born out of a demonstrated need to connect entrepreneurs in-person globally.

Q & A with Startup Stay co-founder Fred Caballero.

What is Startup Stay?

Entrepreneurs in start-ups can stay with and host other like-minded entrepreneurs when travelling for business. Both guests and hosts give back by sharing knowledge, skills or even tapping into their business network as part of the experience. You don’t pay to be hosted and membership is by invitation-only.

This platform serves entrepreneurs that want to meet other fellow entrepreneurs while travelling or at home, and that also value:

a) Building meaningful face-to-face business connections with entrepreneurs worldwide.
b) Gaining access to local insights from a host entrepreneur.
c) Increasing productivity and eliminating accommodation costs

How is the way you are solving this problem more special or effective than previous attempts you or the market has seen before and how different do you have to be to succeed?

Currently, there are no hospitality exchange platforms serving entrepreneurs only. The “Stay with me for free” or “Pay to stay at my place” value propositions that are out there, are simply not enough. People in startups live and breathe a unique lifestyle and attitude and Startup Stay is here to bring a contagious chutzpah into business travelling experiences, sparking new relationships, collaborations & business opportunities.

The idea is to keep everything as simple and raw as possible. This is a platform for entrepreneurs to find other entrepreneurs, communicate and meet face-to-face. The more we enhance that once thing only and avoid adding “shiny”, useless stuff, the better. 

Why should people or companies use your startup?

LinkedIn is out there to add professionals connections (that you have ideally met/know already) so you can stay in touch/visualize your business network.

Startup Stay works the other way around. It’s a network of entrepreneurs that is expecting to meet face-to-face with other like-minded entrepreneurs. There are countless reasons why companies or start-ups should use it. For example:

  • Gain local insights about a specific city or industry through the right people.
  • Save time by getting introduced to key professionals by your host or guest.
  • Maximise your time while travelling for business by learning from another entrepreneur while avoiding accommodation costs.
  • Expand your business network in every trip or at home.

Other than going viral and receiving mountains of positive PR, what is the strategy for raising awareness and getting customers/users? 

We’re still learning a lot from the members so, number one would be to work on the improving the stickiness of the web app and making available our mobile app to easily access the platform on the go to J. We deeply believe that spending almost 100% of the time in the platform is what is going to impact directly the usage, therefore the increase in number of experiences and member growth.

This is a service that’s all about the experience. If we want entrepreneurs to produce quality word-of-mouth we must facilitate that from a technical perspective (platform) but also from a strong community angle, being there to talk to them, answer any questions, help them find entrepreneurs, etc. This human aspect is paying off very well. 

What other options have you considered for the business and the team if the original vision fails?

Our big goal is to connect millions of entrepreneurs face-to-face around the globe while helping them also avoid accommodation costs. One of the things we’re learning now is that entrepreneurs use a lot as well the platform for meetings. I guess we would shift from a hospitality exchange platform to something slightly different but would love to serve the same goal ideally.

What mistakes have you made in the past in business and how have you learned from them?

We meet a lot of people, read loads of posts and books about the subject. While that helps tremendously and then, we seamlessly apply it to our day-to-day activities… it’s simply never enough since you encounter new situations all the time.
One of the things we’re doing much better now is not wasting time with too many meetings, and doing proper due diligence on everyone we meet or conference with.

What is wrong with the travel, tourism and hospitality industry that requires another startup to help it out?

What’s wrong is that most of what’s out there is pretty much for “everyone”.

We strongly believe that the future lies in niche communities, tribes that feel identified with a topic and are passionate about it. There are still an infinite amount of profitable niches to be served in the travel industry.

Choose the one you want to serve and don’t listen to investors that will only advise you to become a replica of AirBnB, just to get a chance of getting investment. They’ll also make you believe that if you’re not a potential US$1 Billion valuation startup you should give up.

Tnooz take:

The concept of connecting entrepreneurs as they travel is brilliant, and is most definitely something that we’ve seen before in various capacities.

The specific focus of hosting/meeting visiting entrepreneurs has appeal to locals looking for exposure to new people and ideas, and the prospect of staying with an entrepreneur while traveling appeals to the implicit understanding entrepreneurs have of the lifestyle – as in, they are more likely to understand that you are not being anti-social by furiously typing away on a computer late into the night.

All that being said, the niche is small and with any social network, the risks of profile fatigue are large. The company will need to continue to promote the value of the connections it facilitates, and ensure that every user is reaping benefits from participating in the network.

Startup Stay points to a Global Entrepreneurship Monitor report that describes 400 million worldwide entrepreneurs, 18 million of which sell services and products internationally in a market valued at $8.6 billion.

Perhaps this niche is not so small after all – and given the growth of Airbnb and the newly for-profit status of CouchSurfing, Startup Stay has a solid chance to create an active and engaged niche of traveling entrepreneurs that build networks and strengthens ties globally.

Snap poll:

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Nick Vivion

About the Writer :: Nick Vivion

Nick is the Editorial Director for Tnooz. Prior to this role, Nick has multi-hyphenated his way through a variety of passions: restaurateur, photographer, filmmaker, corporate communicator, Lyft driver, Airbnb host, journalist, and event organizer.



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  1. Adam - Tropical Nomad

    I think this is such a great idea. You never know who you will meet on your travels and the right person might be put in your path at the right time via this. Or, you might just meet some cool people who share similar interests and have a good chat about business and life.

    • Nick Vivion

      Nick Vivion

      Agreed – a great way to connect with other entrepreneurs in a direct way not offered by other services. Also, they’ll understand when you spend the day typing away on your laptop as you work as you travel!


      • Psycho

        Going to use StartupStay in my travel to Prague where we’ve joined SartupYard accelerator. Find me on StartupStay if you’re planning your trip Prague in the following 3 months. 🙂

  2. Fred

    Thanks Bart! …and welcome on board mate! You’re fast 🙂

  3. Bart van Poll

    Wow, I haven’t been this enthusiastic about a web service for a long time!

    I travel frequently, and I really like meeting inspiring entrepreneurs on my travels. It’s always on my to-do list to check out who’s interesting in the city I travel to, but most of the time I don’t. It takes too much time to research and set up appointments.

    This service seems to solve my issue. I will know who’s where, and who’s interested in meeting other entrepreneurs. Needless to say: I’ve applied!

    From a business perspective I also wonder where the money will come from, but as a user I must say I don’t really care 😉

    • Nick Vivion

      I’m thinking they should ask for a “friendly commitment” of a small slice of shares from businesses born out of connections created on the site!


  4. Rentini Travel

    Sounds like a fun idea and there is a great potential to spread quickly across the Silicon Valley and NYC. It would be a little bit more challenging to push it beyond major hubs though. Still in all, like minded folks all want to be connected. That’s a great driving factor!

    • Psycho

      It has some viral effect – the word spreads all over the world through enterpreneurs themselves. I live in Moscow and I use this service as I had mentioned already. 🙂

    • Fred

      Thanks Rentini

      The main hubs make a big difference indeed. We think though, that in a very good way, we’re “early to the party” since everyday, we learn more how underlooked entrepreneurial hubs are experiencing fantastic growth (Singapore, Lisbon, Sao Paulo, etc). These spots are the areas of opportunity for us and where the word travels faster at the moment.

  5. Drew Meyers

    Love the concept. Totally agree the future of the web lies in niche communities, and this is an interesting proposition to a passionate group of travelers.

    My questions — 1) how will this remain top of mind to people when they are in a non travel scenario? 2) What’s the plan to make money?

    • Psycho

      One of the things to be engaged with the service are notifications about enterpreneurs coming into your area and messages and stay requests from them.
      I don’t know what Fred thinks about monetization but I see some advertising possibilities right now – for example, there are some “partner events” already, though I don’t know exactly what it means.

      • Fred

        Thanks very much Drew and Psycho for the comments!

        The platform is now doing a percentage of what we want it to do. Drew had a great point about the non travel scenario and as Psycho said, the “entrepreneurs coming to your area” is one point. This experiment went very well to keep locals engaged while helping guests.
        We’d love for the platform to become more of a place where you can get also some key info such as city events (funnily enough, this is not easy to get at the moment) and key activities.

        Regarding monetisation, we’re in talks with a couple of brands. In parallel, we’re learning a lot, especially from power users, to build a premium service. We’d like to test this in Q1 2013.

      • Nick Vivion

        I also could see coffee shops, restaurants or other service providers targeted traveling entrepreneurs with the service.

  6. Valentin Dombrovsky

    That’s a great product – I’ve already used it to have 2 awesome meetings with foreign enterpreneurs in Moscow. Find me there to meet for coffee if you’re planning a trip to Moscow. 🙂


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