John Berkowitz and the Space Between Searching and Deciding

Before John Berkowitz tried to help people choose a home, he tried to help them choose a restaurant. His early product, Map Mojo, sent personalized suggestions by text: somewhere to eat, somewhere to drink, something to do. The question was pleasantly small. Dinner rarely requires a thirty-year commitment, although an unfortunate tasting menu can feel that way.

What interested him was the conversation. People could ask for advice, refine their preferences, and explore options without the social pressure of having another person waiting for a decision. A modest recommendation service offered a way to study something much larger: how people decide what they want when they cannot quite explain it yet.

That question carried Berkowitz into housing. He co-founded OJO Labs with David Rubin in 2015, acquired home-search portal Movoto in 2020, and became president of real estate at Lower when the mortgage lender bought Movoto in May 2025. Across those changes, his work has kept returning to the moment when browsing needs to become a conversation.

A napkin before a business plan

Berkowitz grew up in New Haven’s Westville neighborhood. His father was a general contractor; his mother worked in early childhood education. His older brother, Ben, became a co-founder of SeeClickFix, the company that helps communities report problems and request local services. Making something useful was a familiar family occupation.

He remembers his father sketching ideas on napkins. Childhood friend Ben Rubenstein later brought him into Yodle, the online marketing business that became his first major company. The family connection and the friendship belong near the beginning of his story: the people around him were already turning practical frustrations into things they could build.

Berkowitz attended George Washington University from 2001 to 2005, studying international business. Yodle followed in 2005. Its customers were small businesses trying to reach people online, businesses for which being good at the work and being easy to find were increasingly separate jobs.

The company grew to more than 1,400 employees and served over 50,000 small-business customers. Web.com completed its acquisition in March 2016, under an announced $342 million cash deal. For Berkowitz, it was an education in the distance between putting a business on the internet and helping that business acquire a customer.

The restaurant recommendation that outgrew dinner

OJO began with an interest in better consumer decisions rather than a predetermined allegiance to real estate. Map Mojo let the founders watch how people responded to a conversational assistant. The housing focus came after they considered where the technology might be useful and where a difficult decision carried substantial consequences.

There is a certain ambition in moving from choosing a bar to choosing a house. There is also a practical continuity. Both require discovering preferences. Housing adds money, timing, unfamiliar procedures, and several other people with calendars. A recommendation that feels right has to survive contact with all of them.

Berkowitz’s answer was to combine machine intelligence with human expertise. Software could help people explore, learn, and articulate what appealed to them. Professionals could help them act. The business would have to manage the handoff between those activities, with enough context preserved that a customer would not feel obliged to begin again.

One early example was Kitchen Fit, introduced in 2020. It used images to help people identify their kitchen preferences through OJO’s text-based assistant. Berkowitz observed that people cared intensely about having an attractive kitchen even when they did little cooking. Apparently the oven can be ornamental; the aspiration remains fully operational.

Buying the front door

The next problem was distribution. An assistant could help a homebuyer, but it needed to meet that buyer somewhere. Movoto already had a home-search audience. Combining the portal with OJO’s guidance would give Berkowitz’s company a place to start the relationship, then remain involved as a visitor moved toward finding an agent and buying a property.

The acquisition was announced in June 2020 alongside a $62.5 million funding round. It joined two different assets: a place where people searched and a system intended to help them work out what to do next. For a founder concerned with decisions, owning that starting point mattered.

Growth required experienced people as well as technology. OJO’s leadership hires included Chris Heller, formerly chief executive of Keller Williams and Mello Home; Karen Starns, who had worked on brand and customer experience for Amazon’s smart-home devices; and Charles Myslinsky, whose product background included Jet.com and Walmart.

Those appointments suggest how many different kinds of judgment the company needed. Real estate brought relationships and operating knowledge. Consumer technology brought lessons about how people use a product. Building a service across both meant recruiting people who understood different portions of the same customer’s day.

Recognition followed. Berkowitz won an EY Entrepreneur Of The Year Central Texas award in 2021. OJO placed No. 49 on that year’s Inc. 5000. The distinctions recorded a period of expansion; they also raised the less glamorous question every growing business eventually faces: whether the organization can keep delivering what attracted people in the first place.

His preferred weapon: a warm introduction

By 2024, competition among property portals had become a contest in which advertising budgets received almost as much attention as houses. Berkowitz publicly declined to make an advertising arms race his strategy. He argued for technology, efficient operations, distinctive data, and experiences that helped agents and consumers succeed together.

His explanation became particularly concrete around introductions. He wanted consumers and agents connected in live conversations, with a concierge team following up on how the relationship was working. A name delivered to an inbox and two people actually speaking occupy very different places on the road to a transaction.

It is an unusually human preoccupation for someone whose company started with conversational AI. The machinery makes an introduction possible; the introduction still has to be useful. In his account, an agent’s experience and a consumer’s confidence are connected. A badly handled lead wastes time on both sides.

“I'm going to fight in other ways.”

John Berkowitz, on competing beyond advertising budgets, 2024

He has been equally willing to puncture the appearance of effortless progress. In a public reflection in early 2025, he called 2024 the hardest year of his entrepreneurial career. Awards had arrived, but the operating reality had often felt defensive. He described the team emerging more focused and efficient, a more revealing account than a procession of trophies.

A mortgage lender enters the conversation

Lower’s purchase of Movoto in May 2025 added financing to the arrangement. Berkowitz joined as president of real estate, working alongside Lower co-founder and chief executive Dan Snyder. A home-search audience, agents, and local loan officers would now sit within the same broader business.

Lower reported that Movoto had attracted more than 150 million visits in 2024. That figure measures visits, including repeat activity, rather than distinct people. The distinction matters: a person considering a move may return many times before being ready to act. Berkowitz’s approach is concerned with what happens during and after those returns.

The combined operation’s proposition was to connect consumers with agents and lending professionals earlier, bringing questions about location and affordability closer together. Financial terms were undisclosed. Its practical promise was straightforward enough: fewer disconnected conversations between discovering a home and finding a way to buy it.

In April 2026, Lower formally launched Movoto Advantage, a subscription program for individual agents. It limited membership by market, vetted applicants, and used live transfers to connect them with prospective buyers and sellers. Lower said roughly 200 agents had enrolled since the rollout began in late 2025. The product gave a specific form to his longstanding preference for conversations over contact lists.

In discussing OJO’s purpose, he has drawn a distinction between the work a business performs and the difference it intends to make. Personalized guidance, in his telling, should help people who might otherwise struggle to obtain attention and support. That ties the commercial model to an ambition to make homeownership more accessible. It also supplies a practical test for the technology: whether somebody gets useful help at the point when uncertainty would otherwise stop them. A product demonstration can show a clever answer. Following a customer through a decision asks considerably more of the organization behind it.

The extended executive team

Berkowitz describes company-building in terms that extend beyond the office. In a 2023 conversation with Alexa von Tobel, he explained that he treated OJO as a family business and considered his wife and four children an extension of his executive team. That is quite a large committee before anyone from finance has joined the meeting.

His advice to aspiring founders has emphasized having a co-founder and choosing partners who will remain committed through difficult periods. His own OJO partnership with Rubin gives that advice a practical context. He has also served on CASA of Travis County’s board and joined RealWork Labs’ board in 2021, supporting another Austin company working with local service businesses.

The connections are consistent with the problems he chooses: local businesses trying to find customers, homebuyers trying to find guidance, founders trying to find someone who will stay in the room. Berkowitz keeps building technology around those encounters. The question that began with a dinner recommendation has acquired mortgages, agents, and corporate transactions along the way. It still ends with a person deciding whom to trust.