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Who *we* think should have won the iOi Pitch Battle this year

(TECHNOLOGY) At this year’s iOi Pitch Battle, a very cool, sexy brand won, and while we applaud them, there was a hidden gem that should have won!



nar ioi pitch battle

Congratulations to Feather, the winner of the 2021 iOi Pitch Battle, put on by the National Association of Realtors. Their sexy furniture and decor rental startup stands to be a household name in short order, and they absolutely deserve the $15,000 giant check they were presented on stage, but perhaps there was someone who tied for first? Before we share with you who we think that is, let’s introduce you to the Pitch Battle and to all of the finalists.

Pitch competitions typically pit startups against each other for a cash prize, but they all benefit from getting in front of an audience that might either invest or use their product. The iOi Pitch Battle put a dozen startups on stage, each introduced themselves to bright lights, loud and enthusiastic music, all to a boxing theme (professional photos of them with dukes up). Clever.

I’ve judged dozens of pitch competitions and demo days in the tech sector so it was hard not to scream questions from the audience, but I had pretty strong feelings about each startup. That’s a great sign, as apathy about any competitor is an indicator of a weak lineup – that was not the case here. The competitors came from all sorts of backgrounds, even a West Point grad and a law enforcement officer turned Realtor, all seeking to improve the real estate industry in various ways. They each had four minutes to pitch, and roughly four minutes to answer questions from the expert judges.

Let’s get to know each finalist:

Here they are in order of their appearance on stage (so you won’t know who our pick is quite yet), and the italics are their pitch on the iOi website, followed by our takeaways from their pitches:

  1. Docitt“Docitt examines a consumer’s debts and credit to orchestrate the optimal credit profile and the best integrated and actionable (financial) solution to improve the consumer’s purchasing power.” On stage, they noted that consumers are being denied for loans they shouldn’t be, and asserts it is $30B in lost commissions for agents. They say traditional lending has failed because of the limiting underwriting process. The goal is to unify a bigger picture of a consumer’s financial situation and make the decision “actionable.” We thought this concept was so important in today’s world of otherwise “credit invisible” consumers that shouldn’t be, but we would have asked more about the company’s inspiration to dig into who they are rather than a startup with dollars in their eyes, seeing expansion opportunities across student and auto loans as well. The short timeframe limited their pitch, but I needed a story of nobility to buy into this concept. Lame, but true. I’m a sucker for a good story!
  2. Parafin“Parafin is a cloud-based design platform for real estate developers to instantly generate building designs, budgets, and proformas for their next construction project.” Their brief demo showed how a hotelier, for example, could plug in an address, then flip through the 3D prototypes overlaid onto the exact property and immediately know not only visual fit, but budget and financial models, all in real time. They plan to service the multifamily sector next, then student housing going forward. It was a pretty phenomenal concept and one that we suspect will probably get acquired by a larger brand like CoStar given the limits on how a small team could scale something so ambitious.
  3. Renter Mentor“Renter Mentor is a platform that provides a centralized, secure, and automated way to list, manage, and find affordable housing.” This startup noted that there is a 10M unit shortage of affordable housing and over 500k homeless in America because of an overly complex system that lacks a centralized platform. After his time at a housing agency, it became the founder’s “personal mission” to take action, so Renter Mentor is a platform for finding, listing, and managing affordable housing units. They collect and sell data, and charge software subscriptions to agencies and property owners. The reason this noble startup didn’t win is that the judges (per their questions) could tell it was more of a statewide startup than national, but with the right team and mentors in place, a state program with strong roots is still investment worthy, but could do better by dominating pitch sessions for social good startups as a NPO that could then grow nationally.
  4. Milestones“Milestones is a customer-experience platform for buying, selling, and managing home ownership—provided by real estate professionals to their clients.” Lemme tell ya – the founder of this company came out strong and is clearly a seriously good salesperson (the crowd went wild, no kidding). Her pitch was simply that this is a platform wherein a broker can monetize all ancillary services in a RESPA compliant way (that could have been the entire pitch and it would have had buy-in). From lead to long-term relationships, the startup’s goal is to reduce the effort of relationship management and it already has 8k agents onboarded. Slick sales pitch aside, we’re curious what was proprietary about the software or maybe what relationships they had that could surpass their competitors with market adoption. It’s one of those products that is so simple that if all agents were using it overnight, the industry would be better for it.
  5. Matrix“Matrix is a fintech digital application that provides deeper insight into credit profiles of would-be tenants by automating conditions and providing recommendations to landlords for rejected applicants.” They gather data from tenants (banking activity, tax history, credit analysis, employment verification, resident history) and claim to make it more usable for Realtors and landlords to process that data. They’ve created the “MAIA” score (an alternative lending score) based on that data and even uses computer vision to extract that data and detect fraud, then offers financial services. They really hit all of the magical talking points for 2021, and they pitched themselves as a rental application analysis platform, but what set them apart to us was their scoring which is a win for landlords and the industry, but also for more potential renters whose full credit picture isn’t depicted by the outdated FICO scoring system.
  6. Hospiria by Under the Doormat Group – “UnderTheDoormat Group is a business professionalizing the short-term rental industry and transforming both the property and hospitality industries with three unique products.” Okay… that doesn’t have much to do with what their pitch was on stage, but let’s proceed anyhow! Hospiria aims to address some shortfalls in short term rentals (STRs), noting that several organizations are missing out on the benefits of STRs, so they manage the process and get the listing out to all of the major aggregators. They offer three tiers of service and even a consultancy service to manage a listing for a property owner. They take reservations, payments, and so forth. They say they’re popular in the UK, and to us it appeared like more of a clever lead gen company for STR owners than anything (nothing wrong with that, it just wasn’t the pitch on stage). To be fair, I’m always highly skeptical of any bleeding of STRs into multifamily because of the potential fair housing implications. This one was kind of all over the place, so I’ll look forward to seeing their progress in a year or so and how they refine their model!
  7.“’s suite of AI-powered solutions enable real estate companies to instantly extract insights (room type, home features, styles and condition analysis, and more) from their property imagery.” The example they used was this: Imagine being able to tell with data how a listing’s curb appeal compares to the neighbors’. Heads nodded “ooh, yes” across the room. The founder asserted that 1 million property photos are uploaded daily. That’s a lot of data not being used. Using computer vision (a keyword flaunted throughout the entire iOi event, so keep an eye on it), aka AI’s ability to understand the content of a photo, clients can reduce man-hours and reduce risk. Color us impressed at the next generation concept akin to when Google Analytics launched so site owners could actually capitalize on the data that was just sitting there unused all along. Our only concern is how their Terms of Service will address ownership of uploaded/used photos (it’s an ongoing problem in the industry, and they’ll need to address this head on).
  8. Otso“Otso provides A-rated insurance coverage for lease security, an alternative to traditional cash deposits and letters of credit, which provides landlords increased protection against default.” They note that $250B is in locked capital at any given time, and that “deal costs greatly outweigh securitization,” and that “collecting collateral is difficult.” They claim they can get up to $100,000 approved in minutes. Tenants sign up online, Otso decides that day. They announced on stage that they’ve just partnered with a $2.5B insurance carrier backing their policy so they can now offer coverage up to $500K. This was a rare “duh” moment for us, and it was suddenly difficult to remember a world just moments before learning about Otso, where the stakes were too high for commercial real estate. The timing is so relevant for their launch as the sector struggles more than almost any other in America, and reducing those barriers can bring companies back into the fold that might otherwise have sat on the sidelines.
  9. Zipi“Zipi reimagines a fractured system to easily facilitate and transact real estate with their back office, accounting and digital payment offerings.” This was another with an enthusiastic founder who is a real estate practitioner with badass sales skills. He passionately explained that there is no standardization to running a brokerage, and with his industry-proven standards, he was able to increase productivity in his two top-tier KW franchises. With Zipi, brokers are offered transparency to their accounting from start to finish, and they don’t charge for their open API in hopes that others come build on their platform. We always love startups that come from within the industry to solve a problem they understand so extremely well. Simultaneously, we worry that it’s a saturated sector and wondered what’s to stop a large brokerage like KW from just doing this themselves.
  10. Remarkably “Remarkably is a marketing and business intelligence platform that aggregates disparate marketing and leasing data, monitors and analyzes performance, forecasts future trends, and more.” Their founder announced that $10B is spent annually on advertising in the multifamily sector, with $5B wasted. This is the first multifamily business intelligence (BI) solution. Users get machine learning (ML) powered alerts with leading indicators instead of lagging. The idea is to use AI insights with data converted into a UX that non-technologists can easily understand, even offering goal modeling for better forecasting. For anyone who has ever spent time at a larger multi-family brand, this is pretty exciting in that it ties in to their existing rent rolls and marketing tools – those aren’t typically married. Very cool!
  11. “HighNote Labs is a sales pitching platform that streamlines the sales pitch process for agents listing presentations, offers, new buyers, and agent recruiting.” This pitch was popular with the audience of investors and technologists – it’s basically a customizable sales pitch to send leads to which supports images and videos, and churns out analytics for users beyond the standard (including how long they’re reading what content, etc. which is standard for a site, not standard for an app for your listing presentation and so forth). Lots of well known names in real estate were flashed on the screen as users. It was one hell of a sales tool, but to us, it felt like a sophisticated plug and play Wix for Realtors, so I wonder how the industry (not just me, a known jerk) will perceive it, given that it’s slick and a pretty tight offering.
  12. Feather“Feather is the next-generation furniture and home decor rental service that makes it possible for people to find beautiful furniture quickly, without the upfront cost and commitment of traditional retail.” Basically it’s CORT, but not ugly as hell (all our words, not theirs). It’s really sexy furniture and decor – the founder noted that furniture is the third largest asset class and combined with the nomadic nature of younger generations, their offering has already earned them $60M in venture capital from prominent firms in the VC world. They’ve taken on the very expensive and complicated task not only of warehousing massive amounts of product, but reverse engineering the technical delivery management process. The application to this audience was home staging. I loved the company, but in the context of this particular pitch competition, I felt like it was a stretch as an ancillary product and I was a little pissy that they’d already earned millions in funding when a few of these startups were smaller outfits in need of the injection of funds and exposure. Still cool, though!

After the competition, before the winner was announced, we spoke to investors in the audience.

It’s no surprise that there was no unanimous winner between them, but as we spoke to each one on one, what was clear is that the priority was investing in teams. The pitch was almost secondary. Yet another concept that wasn’t surprising.

Investors don’t just invest in an idea, a product, they’re focused on the founding team and their processes, their differentiators. Many were drawn to Milestone and HighNote which tells me there’s still tons of money and attention left in the till for agent-focused products.

We also spoke to a few technologists whose preferred winners were inconsistent with only Remarkably and standing out. But this specific panel of judges chose Feather (which we did not for reasons mentioned in the blurb above about them).

Our chosen winner is…

This was an impossible choice, because we are most rooting for Renter Mentor to thrive, as they could have such a meaningful and deep impact, and if we only had $100 dollars left to our name and had to invest it, we’d choose Otso.

But remembering that the conference (and therefore the Pitch Battle) was focused on tech innovation, we felt that should have won.

What they’re talking about doing with AI to harvest billions of data points from a gajillion existing photos is pretty mind blowing, and it feels so relevant to this moment in time. It’s like we’re watching website analytics be born – if they can corner this segment of the market and dominate before saturation hits, they’re going to be a serious player in the industry, both residential and construction.

So congrats to Feather, but also congrats to which wins exactly zero dollars from us, but if they run this startup well (which we believe they will), they will be a ubiquitous brand very soon. on stage

Lani is the Chief Operating Officer at The American Genius - she has co-authored a book, co-founded BASHH and Austin Digital Jobs, and is a seasoned business writer and editorialist with a penchant for the irreverent.

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Real Estate Technology

How deepfake images could infiltrate the market

(REAL ESTATE TECH NEWS) The rise in quality of deepfakes has even lead to the development of fake images in geography and housing. Here’s what to look out for.



A digital map open on a computer, where one has to be wary of fake images.

With the onset of the computer age, we have seen a great deal of false information spreading around the world. From photoshopped images to presidents broadcasting fake information, there is a lot to be wary of. The internet is rife with data that truly needs to be verified at any given turn. The dangerous part is not only what people can do with that information, but also how they can hide things with it.

Satellite imagery has been on the rise for a few decades. An image that is already grainy and hard to see would be child’s play to alter. Maybe even to create from scratch. Tagging GPS coordinates are a simple alteration inside of photoshop too. Fakes, upon fakes, upon fakes.

In 2019, the US military warned about the possibility of fake geographical information being perpetuated across the internet. It then actually came true to the embarrassment of the Chinese government. Satellite “evidence” was used to report detention camps hidden away in the countries. The “camps” turned out to be re-education facilities for China’s mentally deviant populace. However, that’s another rabbit hole to run down. The point here is that the images that were released in 2015 showed absolutely no facility and then pictures in 2018 showed a massive facility.

An assistant professor, Bo Zhao, with the University of Washington decided to illustrate this again with a study. His opinion was “the first step to tackling these issues is to make people aware there’s a problem in the first place”. He and his colleagues published a paper on “deep fake geography.”

They conducted experiments in generating and detecting imagery for suburban homes, which clearly demonstrated the affect of this technology on our economy. They were able to easily convert the shape and layout of a neighborhood in their images.

From this work we have a few new terms to be aware of. Threats of “paper towns” and “trap streets” are two of the new resounding terms. These new ideas can lead to a modicum of potential issues. The team actually created a software that has the ability to create these fake images. They did the work themselves, leading one to believe that the basic knowledge is there for anyone with a little know-how.

The moral of the story is, don’t trust anything from the internet. It’s all an opinion coming from some other flawed human being, and you don’t ever really know why people are putting that information out there. Always know and check your sources.

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Real Estate Technology

Value privacy? DuckDuckGo is the answer to breaking up with Google

(TECHNOLOGY) DuckDuckGo is a search engine that doesn’t listen to home recordings, sell you stuff, or track your every movement. They just provide search results.



DuckDuckGo search engine

A popular Wired editorial caught our eye, urging folks to consider using DuckDuckGo instead of Google. We continue revisiting this story. And as someone who does use DuckDuckGo as my default search engine, it made me smile.

In the modern world of telecommunications, the only real currency is trust. When you buy an iPhone or an Android, you’re not really buying a set of features. You’re buying assurance that the cell phone company you’ve chosen isn’t going to screw you over too badly. You have a device in your pocket that tracks you, everywhere you go.

Even when you have location services off, your smartphone knows where you are through a combination of the Wi-Fi networks nearby and your phone’s motion sensor. Here’s an article from nearly a decade ago talking about how this process is 90% accurate. How much better do you reckon it’s gotten since then?

The thing is, Apple and Google both kinda suck at the privacy thing. Here’s an article about Siri recordings being made when Siri isn’t meant to be turned on, and the quality assurance contractors who then have to listen to people having sex. (Apple is ending the contractor program, after a public outcry.) Here’s an article about a big ol’ leak of Google Home recordings, many of which were made without the user activating Google Home. Here’s an article about Amazon leaking 1,700 audio recordings from someone’s Alexa to a complete stranger!

So your phone companies don’t really protect you that well. Apps take advantage of this too. If you still have the FB app, you should probably delete it! Here’s a story about a psychiatrist realizing that Facebook was suggesting that her patients add each other!

So privacy matters, and Google sucks at it. Google is also a HUGE business. It’s an enormous company that wields so much influence on ours lives that there is an entire industry now called “search engine optimization” dedicated to unraveling its whims.

And what whims! One major update a few weeks ago caused a 30-40% drop in traffic for some websites. These updates are pretty opaque, and a whole constellation of websites has arisen to help the search engine optimization workers (or SEOs, for short) untangle what those updates mean, and why their traffic has suddenly gone down.

And at this point, Google only kinda wants to serve you results. Mostly they wanna serve you ads, and highly-optimized shopping results. One of the big problems facing SEO workers right now is that you can bust your ass to get a company to the front page of results, and it may not matter if you don’t crack the top 3. Because people do most of their Internetting on their phones now, and ads take up most of the screen space when someone Googles.

So Google isn’t great at privacy AND their priorities are skewed. But this is an article about DuckDuckGo, right? And we’ve barely covered it! So let’s talk about that a little.

DuckDuckGo doesn’t save your searches. It forgets everything you search. And you know what? That feels incredible. There are drawbacks. When I type the letter L into DuckDuckGo, it doesn’t immediately suggest “Leonard Bernstein shirtless” like Google does. But the ten seconds it takes to type that out is worth the knowledge that my data isn’t being stored by my search engine.

And yes, Google pours a ton of money and attention into their algorithms, and they’ve got a years-long head start on DuckDuckGo. But usually, DuckDuckGo still manages to get me exactly what I want. Sometimes, it’s even better at giving me what I want. Because it’s not serving me ads, or trying to second-guess me. It just…gives me the thing I asked for.

There are still some instances that send me to Google. If I’m looking for a specific image or gif, for instance. Or if I’m looking for a certain news story. And there are certain niche searches where Google’s experience is necessary. But for the vast majority of what I need, DuckDuckGo is there, serving up only what I want and protecting my privacy while it does. And it feels GREAT.

This story was first published in December 2019.

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Real Estate Technology

20 of the best free professional tools for your business

(TECHNOLOGY) Running a small business is a ton of work and you need all the help you can get. Here are 20 free tools that help make it a little easier.



digital tools

When running your business, big or small, you’re only as good as what’s in your arsenal. This applies to your ability to be creative and think on your feet, as well as to having tangible tools at your disposal.

Below, we’ve outlined 20 of the top free tools that are designed to help grow your business – let us know in the comments what you love or what you’d add!

  1. Google Analytics – this is a definite need. With the world continuing to grow more and more digital, it’s necessary to know how your business is operating in the online realm. Google Analytics provides data about your small business, including traffic to your site and clicks on links. It gives you an idea of who is visiting and when, allows you to track your goals, and generate audience reports. Google also offers virtual classes that teach you how to master the platform.
  2. Hotjar – want to understand exactly how visitors are using your site without getting lost in the shuffle of numbers and data? Hotjar is where it’s at. You can see a user’s behavior and their exact process of perusing the site. There are also tools like feedback polls that allow your audience to interact with you when using your site.
  3. Canva – this is one of the best visual tools to create graphics for your company, both to print for physical display and to use on social media. The platform is easy-to-use and allows for a myriad of sizing options, backgrounds, and stock images.
  4. ProProfs Help Desk – this is a ticketing system that allows your visitors to contact customer service and start a thread of communication; all while keeping everything ticketed and organized. This also allows for shared inboxes, ticket resolution via chat, and ticket reduction up to 80 percent with knowledge base.
  5. JungleScout – this is your best friend when it comes to learning to sell on Amazon. Regardless of where you are in your seller journey, this tool will help you maximize your skillset.
  6. Kickstarter – crowd sourcing for your business without giving away the equity. This lets you recruit micro-investors and donors for your new business venture.
  7. MailChimp – This is an all-in-one tool that is necessary for all small business users. According to their website, “Bring your audience data, marketing channels, and insights together so you can reach your goals faster. With Mailchimp, you can promote your business across email, social, landing pages, shoppable landing pages, postcards, and more — all from a single platform.”
  8. Shopify – this platform has helped over one million businesses around the world and is continuing to help small businesses thrive. Shopify allows users to create and design an ecommerce website that is backed by helpful tools that help discover new customers, drive sales, and manage your business’s day-to-day operations.
  9. Buffer – provides simple social media tools that receive authentic engagement. Tell the story of your brand while growing your audience. The platform includes publishing, analytics, and engagement.
  10. Qualaroo – this is a customer and user feedback software that states its value as ten times higher than email surveys. It comes with what you need for useful feedback, including AI-powered analytics and reports.
  11. Zapier – a platform to connect your apps and automate workflow. Zapier moves information automatically between your web applications, allowing for more focus on the most important work.
  12. Doodle – a scheduling platform that allows meetings to be booked faster and smarter. No more need for an hour of back-and-forth emailing in order to nail down a meeting time.
  13. Docracy – a home for contracts and other legal documents, created by the community that uses them. The idea is to make these common documents easily available for everyone.
  14. Slack – the ideal way to communicate with your team and keep everyone on the same page at all times. This is a central communication hub where you and your team will stay in the loop, ask questions, and share updates.
  15. GoDaddy Website Builder – this is an extremely user-friendly tool that allows you to build websites that looks as though you paid someone hundreds to build it for you. There’s many options for customization, and they have the tools that help your site look great on both desktop and mobile.
  16. ToDoIst – For many, it’s impossible to stay organized without use of a to do list. With this tool, you (and your team!) can stay organized with the most important tasks and priorities.
  17. Grammarly – When writing copy for your business’s brand, it is important to have as many eyes read through it as possible for any errors. Grammarly is a tool where you can plug your copy in and it will automatically find and highlight any grammar errors or typos. You can never be too careful!
  18. AdobeSign – Formerly known as EchoSign, this tool allows for paperless signatures that help make signing contracts and agreements as easy as the swipe of a finger.
  19. Sumo – a platform filled with tools to help you grow your website. It’s a free email capturing tool that takes only seconds for sign up.
  20. Pixabay – We don’t always have the time or the money to take photos to go along with our website copy and social media posts. Pixabay helps alleviate that need with free stock images that will help your message pop.

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