Ryan Barone

The mechanics of the apartment application, in New York City, around 2015, went roughly like this: a landlord or broker requested a stack of documents - two pay stubs, the most recent W-2, three bank statements, a credit pull, a letter of employment - and the prospective tenant, usually in their early twenties, tried to assemble all of it before someone else got the apartment. The person who got the apartment was often the person who could produce a PDF the fastest. This was, and remains, a strange way to allocate housing.

Ryan Barone was one of the people trying to produce the PDFs. He was a Pace University undergraduate, class of 2016, working through internships at Goldman Sachs and then The New England Consulting Group, then landing an associate role at PwC in banking and capital markets. He wanted a place to live in New York. He did not, at any given moment, have a folder of clean scans on his phone. Neither did his roommates.

So he started building an app. Not a company, initially - just an app. Somewhere he and his friends could park their pay stubs and W-2s so that when a broker asked for documents, they could send them over without a scanner. The app was for tenants.

Then Barone did the thing that turns a project into a business, which is talk to the other side of the market. He started asking landlords what they hated. It turned out landlords also had a document problem. And a rent-collection problem. And a screening problem, and a listing-syndication problem, and a maintenance-ticket problem. All of them essentially boiled down to running a small business in Google Sheets and email.

By 2016 the tenant app had become a landlord app that was still a tenant app. Barone left PwC after roughly five months. He spent the next two years, by his own account, building the software before letting anyone use it.

He has since concluded this was a mistake. "Don't wait for perfection," he told Authority Magazine, phrased with the gentle regret of someone who has watched two years of runway convert into a v1 that early customers would have accepted at v0.3.

RentRedi's market is what the proptech industry, when it is being honest, calls the "long tail" of landlord. These are people who own between one and fifty rental units. They are dentists, retired teachers, real-estate investors with a W-2 job. They are not sophisticated enough to buy Yardi or Appfolio - or, more accurately, they are too sophisticated to want to. Yardi is priced for management companies. The mom-and-pop landlord wants to accept rent, screen a tenant, and get a text when a toilet breaks.

This is not the sexy part of proptech. The sexy part of proptech, until recently, was the iBuyer. Opendoor, Zillow Offers, Compass. Companies that were going to reinvent the transaction. What happened, roughly, is that the transaction proved harder to reinvent than the operating layer, and Zillow Offers was wound down in 2021, and the entire capital stack that had been pointed at iBuying started looking around for something to do.

The operating layer - the software that lives between a landlord and a tenant after the sale - was still up for grabs.

RentRedi's numbers, cited by the company and by Inman when it named Barone to its 2025 Future Leaders in Real Estate list, are as follows: nearly 200,000 landlords and renters on the platform, roughly $33 billion in assets under management, and appearances on the Inc. 5000, HousingWire's Tech100, and Fast Company's Next Big Things in Tech. The company has partnerships with REI ecosystems including BiggerPockets, which sits at the center of a very online cohort of small-portfolio landlords.

The $12M Series A closed in April 2022 - not a great vintage. Rates were rising. Proptech multiples were compressing. The check went in anyway. In the intervening years, RentRedi has done the unglamorous version of what venture-backed SaaS is supposed to do: added accounting, added tenant-communication features, layered in credit-boost and renter's insurance, deepened integrations. There was no rebrand. Barone did not step aside.

The company's headquarters, per its Apollo record, is at 800 Troy Schenectady Rd in Latham, New York - a stretch of upstate strip mall that would surprise anyone who assumes a New York City founding story implies a New York City office. RentRedi is 52 employees, distributed. The About page describes a workforce that includes a lot of landlords and real estate investors, which is the sort of detail that reads as marketing until you realize the customer base is landlords and real estate investors.

Barone lives in New York. He is a Forbes Business Council member and a contributor at Inman and Inc., where he writes short, operator-flavored columns about running rental businesses and running startups. The writing is the writing of an engineer: declarative, checklisted, sparing.

The interesting question about Ryan Barone is not the origin story - the apartment application, the friends, the app in the bedroom, all of it fine and well-worn - but the fact that a decade in he is still holding two jobs. Founder-CEOs get diluted into executives. Founder-CTOs get replaced by SVPs from Segment or Stripe. Barone has done neither.

It is possible this is ego. It is also possible that RentRedi's product is complicated enough - rent flows, ACH, credit reporting, listing syndication to Zillow, Realtor.com and Trulia, maintenance orchestration, lease e-signing - that the person who designed the schema is still the person best positioned to change it. In a world where most proptech founders quietly become CEOs of sales organizations, Barone has stayed the architect.

The extracurriculars, per the RentRedi About page, are basketball, chess, food, and travel. Chess is the most on-brand of these - a game of positional patience with a hard finish, played by a certain type of engineer-founder who is not going to be talked out of a plan by a term sheet. Barone does not, from public evidence, do much of the Founder Twitter thing. The RentRedi Twitter account is functional and largely product-focused.

He has, however, done a lot of podcasts: BiggerPockets, Growth Think Tank, The Weekly Juice, Icons of Real Estate, How Did They Do It. The pitch across all of them is roughly consistent - independent landlords are underserved, the platform they need is not the platform enterprise property managers use, and the app should feel less like accounting and more like a phone. The most common piece of advice he gives young founders is to ship earlier than they think they should.

Which brings the biography to a kind of shape: an undergraduate builds a document app because he cannot find an apartment. He talks to the people on the other side of the market, discovers the software problem is bigger than he thought, spends two years building, launches too late, wins anyway, and refuses to give up either job.

The through-line, if there is one, is that Barone did not particularly want to be a founder. He wanted the app to exist. The company was the container the app came in. This is why the details in every interview keep coming back to the software rather than to Barone himself. It is also probably why, ten years in, he is still, per LinkedIn, in the codebase.

The apartment application, in New York, is still a mess. There are just now roughly 200,000 more people managing around it.