Business Startup Spotlight: Hostfully


Hostfully helps hosts (both individual hosts and vacation rental management companies) be better hosts.

Name: Hostfully, Inc.

Location: San Francisco, CAHopefully


Product / Service Offering: Hospitality platform for vacation rental management companies

Co-founder Interviewed: David Jacoby, Co-founder and President

Other Key Management Team Members: Margot Schmorak, Co-founder and CEO; Noah Neiman, Co-founder and Head of Product

This article is part of our Business Startup Spotlight series featuring entrepreneurs and their companies. We hope that these founders’ interviews will inspire and motivate you as you undertake your own entrepreneurial journey.

Tell us a little about yourself with a focus on what motivates you.

I am a startup enthusiast and have worked my whole career in startups. I enjoy getting my hands dirty and solving real-world problems and improving efficiencies. I love learning by doing, and learning all aspects of how a business is run.

On a personal note, I love to travel, as well as host travelers in my home from around the world. I think travel makes the world smaller. It creates more connections and understanding of different cultures, which is what we need in times like these.

When did you establish your company and where did the idea originate?

In 2010, my wife and I took a one year sabbatical and traveled around the world. We visited 27 countries in five continents, and stayed in 38 people’s homes during that journey, including places such as Lima, Cairo, Jerusalem, Kigali, Hanoi, and Phnom Penh (from traditional vacation rentals, to Couchsurfing, to friends of friends). It was then that I realized the incredible influence a host has on a guest’s stay! Anything my host told me to do immediately was at the top of my priority list, above other travel guides like TripAdvisor, Lonely Planet, Yelp, etc.

After that trip we moved to San Francisco and started doing home sharing in our home, on both Airbnb and Couchsurfing. We’ve had over 100 guests in the past few years and I’ve become an Airbnb Superhost. During this experience, I’ve realized two things:

  1. The incredible pain-point of having a full-time job, trying to provide a consistent five-star hospitality experience to my guests, and being in constant communication with guest after guest (both before their visit and while they are here).
  2. The pleasure of hearing that they went to my favorite local recommendations. Sure, they went to Alcatraz and Fisherman’s Wharf, but it was visiting my local favorite brunch spot, coffee shop, etc., that made their trip truly memorable and unique.

In looking into the vacation rental, I realized there are many platforms (like Airbnb, HomeAway, etc.) that focus on getting the booking, and there are other tools (like property management software and dynamic pricing companies) to help with that. Once the reservation is made; however, there are not many services to help the host be a better host and provide five-star hospitality to their guests. That’s where we come in.

What need or needs does your company seek to fill for its customers?

Providing five-star hospitality on a consistent basis is hard work. Equally hard is communicating with a never-ending flow of guests and all their questions. Hostfully helps hosts (both individual hosts and vacation rental management companies) be better hosts.  Our value proposition is two-fold:

  1. We help hosts provide a more professional-looking experience to their guests. Our flagship product is beautiful guidebooks, available both digitally and in print.
  2. We save hosts time and money by decreasing the amount of unnecessary questions they get from guests. We make important information and local recommendations more readily accessible than the traditional, old-fashion method of out-dated and ugly binders.

What is the one thing that sets your company apart from its competitors?

We are vacation rental hosts ourselves, with a deep knowledge of the industry and pain points. We combine our personal knowledge with the Lean Startup principles. We are regularly testing and iterating on our UX and design based on user feedback.

What was the biggest challenge you faced while getting your company up and running, and how did you overcome it?

Our biggest challenge was “not letting perfect be the enemy of good”, and launching our MVP as soon as possible. There is a never-ending roadmap of new features and design changes, but at some point, you need to trust the Lean Startup philosophy and release what you have, even if it’s not 100% what you want. The benefits are huge, as you get to see real-time customer usage and feedback, which might be different from what you thought.

Are there resources you have utilized that other founders might find compelling or useful?

Your network is your best resource. LinkedIn has been a surprising way of endless introductions. It’s amazing how many people, even distant colleagues and connections, are genuinely rooting for you and are happy to help make introductions upon request.

We also send a monthly “business update” email to connections that have expressed interest in what we’re doing; in those emails we have specific requests for help.

On a daily basis, we use Salesforce, Slack, Pivotal Tracker, and Podio, which are all essential to our business operations.

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What steps have you taken to secure funding for your company and what, if anything, would you do differently if you had to start over?

We would take less qualified meetings at the beginning so you have some low-pressure situations to practice and refine your pitch. By the time you successfully raise, your deck will most likely look completely different from your first version. We actually had some meetings with Series A investors pretty early, and that was quite helpful as the stakes were low. They weren’t a good fit, but we got great feedback.

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Have there been any questions you have had as an entrepreneur of a fledgling startup that you had a particularly hard time finding the answers to?

“What if another company like Google decides to do this?” Unless you are doing a deep-tech heavily-patentable startup, “defensibility” will always be an objection. Don’t stress over it, and don’t keep what you’re doing a secret. There are more important things you need to worry about, such as execution and first-mover advantage. Your ability to be learn, adapt, and execute is your best way to overcome the defensibility objection.

What challenges, if any, are you grappling with?

Staying focused on the big goals and not being bogged-down with all the minutiae of running a business is always a challenge. Luckily we have three senior co-founders and a great team as a whole. Speaking of focus, it is important to know the demographics of your target customer and focus on targeting them specifically.  In our situation, we have seen many unique cases of people using Hostfully for guidebooks. Not only are vacation rental hosts and management companies using us, but so are bed and breakfasts, hotels, travel agents, weddings, office managers, and more. While we embrace everyone using us, we can’t stretch ourselves too thin by trying to market, sell, and customize our messaging to everyone.

What is the most helpful tip or “hack” you’ve ever learned, stumbled across, or been given?

The Couchsurfing community allowed my wife and me to travel the world with free accommodations and local insight pretty much everywhere we went.

Is there anything else you would like to share about your company?

We value strong work-life balance. Many of us are parents, and we try not to work on weekends. We make sure to have some social time before/after meetings, and we don’t micro-manage employees’ hours and tasks. Company culture is important. Make sure you’re having fun. Otherwise, why are you doing this?

Are you familiar with other startups you believe should be spotlighted? If so, we would like to hear from you. Tell us about them, sharing your comments below!

Want to learn about other businesses in the spotlight?  Check out our Business Startup Spotlight Series.

Sandra Sloan

Sandra has previous supply chain and business operations experience which she is leveraging as an author with FundingSage focused on spotlighting entrepreneurs and their startup efforts.