Hosta A.I. Profile logo.

Hosta A.I. provides data solutions for corporations to streamline their online property assessment decisions. 

Founder(s): Henriette Fleischmann, Rachelle Villalon

Industry: Tech

Founded in: 2020

Location: Cambridge, Massachusetts

Interview With Henriette Fleischmann

Describe your product or service:

“Hosta A.I. is a data solution provider enabling workflows for corporations who are aiming to digitize decision making related to onsite property assessment. We built technology that enables our customers to leverage our data fast and simple.”

Describe your company values and mission:

“Hosta A.I. provides access to accurate and accelerated property data anytime and through everyone via simple image captures using a smartphone camera.”

How are you funded? I.e. type of funding, number of funding rounds, total funding amount.

“VC funding, total $15.5 million to date.”

How big is your team? Tell us a little about them (I.e. co-founders, freelancers, etc.)

“Rachelle Villalon, CEO, used to work as an architect in the field. She assessed spaces, created new designs, looked into energy efficiency, etc. Over and over, a very manual process. From that experience, Hosta’s mission was born: Hosta A.I. makes everyone an expert in property assessment. Rachelle decided to head to MIT for a Master’s and Ph.D. in Computational Architecture. Always driven by the possibility to extract all the information she would have needed from a simple picture. Her persistence paid off — a couple of years later and accompanied by her co-founder Henriette Fleischmann, COO, Hosta A.I. has raised $15.5 million, built a team of more than 20 people, and has created a huge market engagement. 

Henriette was born in 1984 in East Germany. Henriette witnessed firsthand the powerful influence a single event, such as the fall of the Berlin Wall, can have on human behavior. Passionate about behavioral economics, Henriette pursued her bachelor of science in International Business Administration and pursued her desire to use analytical rigor to reshape behavior. She started off as Chief of Staff to the CIO of Daimler Financial Services, Sales & After Sales, leading strategic, structural, and cultural change. She later joined a consulting practice, heading Fortune 100 projects in restructuring, new business models, and process optimizations. Ultimately, Henriette joined one of Europe’s largest fashion retailers and drove their first aligned strategy outside of expansion of stores, successfully challenging the conventional thinking of the firm’s management. She attended a one-year MBA program at MIT Sloan. While there, she focused on A.I. and entrepreneurship, which led her to meet Hosta A.I. co-founder Rachelle Villalon. Together, they launched Hosta A.I. in February 2020.”

How did you come up with your startup’s name? Did you have other names you considered?

“Hosta is a plant commonly found in New England. It is very hardy and hard to kill — it’s our spiritual animal!”

Did you encounter any roadblocks when launching your startup? If so, what were they and what did you do to solve them?

“I wouldn’t call them roadblocks, but for sure, there were many challenges.”

Who is your target market? How did you establish the right market for your startup?

“We are working with property insurance carriers, contractors, and data providers. 

Our solution allows for a huge variation of markets. We approached our go-to-market strategy (GTM) very analytically — market size, how big is the problem, how strong is our solution, and our ability to fix this problem. We are focused on creating value for our users in the market. 

Creating value in the insurance market was top of the list — millions of properties need to be measured and assessed every year. And there’s so much potential to help adjusters and contractors to make this process easier and less repetitive using artificial intelligence.”

What’s your marketing strategy?

“Classical B2B marketing — whitepapers, webinars, conferences, and GTM partnerships wherever they make sense.”

How did you acquire your first 100 customers?

“We are a B2B business working with Fortune 100 companies. We are not there yet, but Startup Savant will be the first to know when we have acquired 100 of them.”

What are the key customer metrics / unit economics / KPIs you pay attention to to monitor the health of your business?

“Throughput measured in different variations, customer sentiment, acquisition costs, revenue, product margin, etc.”

What’s your favorite startup book and podcast?

What is a song or artist that you listen to for motivation?

“‘More for Self- & Other Reflection,’ a German podcast on psychology.”

Is there a tool, app, or resource that you swear by to help run your startup?

“The classics: Slack, Jira/Confluence, Github, G Suite, etc.”

What is something that surprised you about entrepreneurship?

“How much can be achieved if all people are fully aligned with the purpose and put in the extra effort to get there.”

How do you achieve work/life balance as a founder?

“Quite frankly, a big point to improve on now that we are just more people driving the company forward.”

What is a strategy you use to stay productive and focused?

“Our leadership team is extremely committed to data-driven communication and decision-making. That’s super inspiring and creates strong motivation in itself to hold oneself to the highest standards. The other is listening strongly to advice and looking into ways to create a learning loop.”

Did you have to develop any habits that helped lead you to success? If so, what are they?

“Many. One is to overcome fear of conflict. But rather embracing conflict in a non-violent way. Where everyone feels they can speak up, experiment, and feedback regardless of hierarchy. The learning loop is so essential to a company’s success.”

What was your first job and what did it teach you?

“Chief of Staff for the CIO of Daimler Financial Services. It taught me how to think strategically and yet be able to execute successfully upon many different strategies.”

Tell Us Your Startup Story

Are you a startup founder and want to share your entrepreneurial journey withh our readers? Click below to contact us today!

Request an Interview

More on Hosta A.I.

Founder of AI Startup Hosta A.I. Shares Their Top Insights

Henriette Fleischmann, founder of AI startup, shared valuable insights during our interview that will inspire and motivate aspiring entrepreneurs.

Read More

Here’s How You Can Support AI Startup

We asked Henriette Fleischmann, founder of, to share the most impactful ways to support their startup, and this is what they had to say.

Read More