From guest to host to company president, David Jacoby takes Hostfully from start-up to highly sought-after software.

Through the Eyes of a Traveler

5 Continents. 27 countries. 38 homes. Over the course of a year, David Jacoby, president and co-founder of Hostfully, discovered what it is truly like to be a guest.

“My wife and I took a one-year sabbatical and traveled around the world. We had our year of fun before having kids!” laughs David. “We stayed in people’s homes in Lima, Cairo, Jerusalem, Rwanda … real random and cool places.”

David and his wife, Kim, in Cairo, Egypt.


After their year of travel, David and his wife Kim settled back in San Francisco where they had two children, now ages 6 and 7. Being far from his parents who lived in Connecticut, he made an in-law suite for them to visit three months out of the year to ensure his children had a strong relationship with their grandparents. “It’s all about the grandbabies now. They don’t care about me anymore!” jokes David.

The in-law suite was created out of a desire to see family often, but nine months out of the year that space wasn’t occupied. Having seen tons of rental properties over his one-year sabbatical, David decided to give the Airbnb world a try to make some extra cash, but more importantly to meet new people and bring the best of San Francisco to travelers. “We’ve had well over 200 guests in our home now and I’ve been a Superhost for over four years,” said David.

But as you can imagine, hosting guests isn’t all that easy.

“I experienced the pain points that come with being in the rental world – of being in constant communication with guest after guest and all the questions that they have before their trip, as well as during their trip,” said David.

Simultaneously, there is the pleasure of connecting with and hearing from guests – that they went to David’s favorite coffee and brunch spots. “Of course, guests did all the touristy stuff, too. But it was staying in my home and going to all the places that I suggested that made their trip unique and memorable, which resulted in the consistent 5-star reviews that brought more people to my place.”

David wanted to keep those positive reviews coming! And as the number of guests continued to grow, so did the need to provide more information.


Transforming the Business of Vacationing

A cup of fresh coffee in hand, he spent hours one evening making “a mediocre looking guide document in Word to give to my guests. It was clunky and took me forever to make. So I started to do some research thinking, ‘there has to be a better way to do this.’”

To his discovery and disappointment, there wasn’t much. Software for travelers to coordinate their trip and find all the things they want to do does exist – but the industry was lacking a modern tool for property managers to present their offerings in the best way, to share favorite and local spots, check-in details, house rules, etc. Perhaps a new technology was the solution.

That’s when Hostfully was born.

“Hostfully truly came out of my own personal experience as a guest and a host, and the good and bad fueled my passion to provide a toolset that makes the life of a property manager easier, and the experience of a guest better.”

The software itself allows property owners to create and adjust >guidebooks to effectively communicate with guests during their stay. But it doesn’t end there.

In June 2018, Hostfully merged with Orbirental, a property management software. With this new addition, Hostfully completely modernized rental management through automation and a robust backend solution for the industry. This combination gave Hostfully the competitive edge needed to serve customers from tip to tail.

“We started getting attention from professional vacation rental managers saying, ‘This is awesome. I want this for all 50 houses that I manage!’ We spent a lot of time building a B2B enterprise software that makes it easy to manage hundreds of listings,” said David.

The best part for users? Everything within the software can be branded to the user’s company, enhancing their brand awareness and increasing future bookings to their site.

“You’ll find that a lot of guests think ‘I booked an Airbnb’ not ‘I booked Joe’s Vacation Rentals of Jersey Shore.’ We help increase their visibility.”


Finding Balance with Accounting Seed

Hostfully is streamlining management for 11,000 properties in 80 countries. Naturally, the team has their hands full.

“All of us are definitely ‘Chief Cook and Bottle Washer’ right now. I’m doing a combo of sales and demos for new clients, onboarding, and all general operations – payroll and our accounting,” said David.

David and the team continue to wear many hats, but realize that they can’t do it all. With thousands of properties to manage across the globe, David struggled to be everywhere at once and looked to technology to find the answer.

“I’m very much about balance in life and I’m grateful that we can build a culture of balance at Hostfully. This is why I was thrilled when I came across Accounting Seed being that it is native to Salesforce and I could take what we were doing manually on Excel documents and connect that to Salesforce through Accounting Seed.”

Hostfully’s other co-founders, CEO Margot Schmorak and CTO Stephan Osmont were a huge help to David as they managed their finances manually. But there was one person in particular that helped Hostfully go from spending hours on end with their accounting to a seamless process without hassle:

His dad, Raul Jacoby.

Raul lives and breathes accounting, having been a CPA and CFO in his past careers. They worked together to get Accounting Seed up and running, which not only improved Hostfully’s business processes through automation and reporting, but it also improved David and Raul’s relationship.

“My relationship with my dad grew tremendously through Accounting Seed. We worked together to get Accounting Seed up and running,” said David. “He knows what everything should look like – what should be debited, what should be credited, and what needs to move over to the P&L. And me, I know Salesforce. And as a small company, we did the Accounting Seed onboarding ourselves, and we spent a lot of valuable time together, which had a positive impact on our relationship.”

David with his family. His father, Raul, is center.


David and Raul continue to work together today, with Raul acting as Hostfully’s CFO. As Hostfully seeks to expand its customer base, the need to easily manage accounting and see ROI has increased.

“We didn’t have the visibility that we have now. We use custom objects that speak to Accounting Seed so that we can see how much money we are bringing in from different types of customers. As a growing company, this is giving us a unique lens and it makes the reporting easy that would have otherwise taken hours in our old way. Accounting Seed took me off of Excel!”

Hostfully is running full speed ahead out of their start-up phase, which requires more reporting for company investors.

“On the fundraising side, we need to provide financial statements to secure funding as a growing start-up. Before, we did not have a clean record of that, but now it is so easy to pull that up from Accounting Seed and Salesforce.”


Doing What Really Matters

The days for David and his team are still long, but they are working smarter and focusing on what really matters – their customers.

“At the end of the day, hearing from our users – how passionate they are about what we are building – that keeps the drive and passion going for us.”

In the rental management world, that’s what it’s all about – people helping people receive the rest and rejuvenation they deserve. “It is really exciting to see the users and knowing that we are helping them make their guest’s vacation the best experience.”

So, what’s next for Hostfully on their journey from start-up to a growing B2B software?

“We will keep working very hard. Thanks to Accounting Seed, I now have more time to focus on making our clients successful.”


To learn more about Hostfully, check out their website.