Built Piece by Piece: Jimmy Mackin of Curaytor

About Jimmy

Jimmy is from Boston, originally a small town in New Hampshire, a small town called Pienaar Ville. He was born and raised about 45 minutes north of the city and has been in the city now for the better part of about 10 years. 

Jimmy went to college at the University of New Hampshire. He is one of six kids. He has three sisters and two brothers. Many of them work for him in Curaytor and every single kid went to college, every single kid went to the University of New Hampshire. His oldest sister, his older sister, his two older brothers, all went to the University of New Hampshire. 

When the time came for Jimmy to go to college, it was sort of like already preordained. He was going to go to the University of New Hampshire. He went there and for the first year while he was in there, he found himself just completely uninterested in school, completely uninterested in the topics they were teaching, and he dropped out his third semester to start his first company. So he does not have his college degree. He dropped out before they could fail me out.

Jimmy’s First Company

He and his partner in crime Christ Smith were the Yelp before Yelp existed. The first company he started with his partner, Andrew, decided to put menus online, because at the time which was around 2000 to 2003, in New Hampshire, there really was no place where you can find restaurant menus and a central database on a website. 

What Jimmy did is they created a website called NH Dine, which Jimmy actually still owns to this day, for nostalgic, nostalgic reasons he renews every year. But it was a site where they basically had to learn how to code and they got the menus from these restaurants, they took photos of them, converted them into HTML, and upload them to the website. It was the first business they started and it was a categorical failure, but it certainly got him started on the path of entrepreneurship.

Prior to Curaytor, after his first failed company, Jimmy was 19 years old at the time. His friend who was working in a bar with the same bar where he met his wife, got him a job at a mortgage company. This was a company called Aegis lending. If anyone who’s familiar with the subprime mortgage crisis, just lending was sort of the king of subprime, interest rates of 9-10%, five to six points on every loan. 

Jimmy got hired as the youngest salesperson history at this organization and probably had a couple of 1000 employees. And when he got hired, he had no experience whatsoever actually doing any sales that were not an area he had any expertise in. So he read every book and get his hands on Zig Ziglar and the Dale Carnegie’s and the Jim Rome’s and the Guru’s from YesterYear, and more or less just did whatever they told him to do. 

Within a few months, Jimmy became Top 10% of all salespeople in the entire organization making more money than he thought was even imaginable as an 18-year-old. Just being able to live that lifestyle, but like most of these stories go, it was a completely unfulfilling job. And one day after working there for about six months making, upwards of $100,000 in that first six months, Jimmy found himself feeling like he was going through a midlife crisis at the age of 19, which is and he just woke up one day he said, he doesn’t want to do this anymore. He hasn’t done anything in his life.

As he’s gonna move someplace and woke up that morning, looked up where to live. Jimmy sorted through a pennant, data map, and said that he’ll move to Las Vegas. Jimmy bought a ticket got on the plane, and flew to Las Vegas that same day, packed, packed up, just his bag, and then he was out the door. Jimmy lived in Las Vegas for a total of one week, before he realized that a 19-year-old couldn’t be living off the strip in Las Vegas. Overall. There was no plan. Yeah. The plan was to get out of New Hampshire. 

He stated he will either gonna go to California or Florida. Through some guidance of a friend, he ended up in Florida. That’s where he spent the next three and a half years of his life. He continued in the mortgage space because he had to make money. But he started getting into consulting, and at that time, learning about, marketing, that’s really what began a sort of the beginning of his career in marketing, was understanding how to put yourself in a position to attract customers and having to learn how marketing actually works was,  absolutely instrumental at that point.

Marketing Career

Jimmy was doing mortgage loan processing because he was somewhat familiar with the real estate industry. He was doing a lot of Google Ads to attract agents to process their loans. If you talk about timing, timing, being one of the X factors in a business run, timing really matters. 

The timing of this was like, 2007, 2008. So it was right at the beginning of the sort of crash, the famous 2008 crash. That business, where people were looking to cut expenses, they were not looking to outsource that time. But one of the things that he learned through that process was just how to attract customers. And that was so interesting because he looks back at that period of his life, and realized that that’s when he really uncovered his passion for marketing, realizing that every business on the planet has got to be great at marketing if they want to grow. They’ve got great marketing. It was a skill he really wanted to hone.

YouTube Channel

Chris Smith, Jimmy’s business partner now for almost a decade. They were both kind of bloggers back in the 2010 era. Jimmy was writing about Facebook, he had this really popular blog called Tech-Savvy Agent. The two of them got connected through that sort of small ecosystem of individuals who are writing about the future of marketing, writing, social media, and they got connected, they became friends and Chris was kind enough to help elevate Jimmy’s brand to a much larger audience. They immediately felt that they can do some amazing work together as a team. They brought a ton to the table, with very different skill sets at the time. 

They were on tour for Agent Reboot where they met the same guy, Jimmy built the Facebook application called the MLS App. And it was a free tool that people could use on Facebook to display their listings. Their belief system was like if the consumer uses Google to find real estate, it is inevitable, they will use Facebook to search for real estate.

People like looking at listings on Facebook, but they don’t search for listings on Facebook. They ended up sort of having to sort of pivot the business because they realized that that wasn’t going to work. But Jimmy did want to say one thing, during that timeframe, in that sort of right when he was getting his PhD in real estate, he had an opportunity to get connected with an individual named Linda Davis. She was his mentor. At the time, she was a 60 some year old REMAX agent, who was he had an opportunity to speak and, and she was someone who just sort of embodied the best of their industry. And he just found out last week she had passed away from cancer. 

He was reflecting on how much she helped me in his early career in real estate, understanding the psyche of an agent understand the challenges that agents face every day. And as a 20 something-year-old individual is looking to sort of break into this industry, she really took me under her wing and really helped me as a business owner. And as a marketer, appreciate the work that you guys do every single day. 

Jimmy would be remiss if he didn’t say for those of you who are listening to this podcast, or looking to start a business or maybe looking to grow your business, Linda was an incredible mentor to him, someone who he’d eternally grateful for, and he thinks this is one of the big, missed opportunities. Jimmy thinks this industry is really lonely. And he thinks not enough agents go out there to seek mentors in or outside. And if you have yet to meet a successful person who has not, yet does not have a mentor, someone, they work with, or talk with or consult with them in their lives. So just some advice.  as he reflect on Linda and her impact for me, it was just so instrumental. Jimmy thinks that he owe so much to her. And he thinks it’s an opportunity for everyone here is listening to realize there are people out there who will help you get to where you want to go.

WaterCooler Podcast

The WaterCooler was a podcast about marketing, sales, and technology. It’s hosted by Jimmy and his partner, Chris Smith. They’ve done now 120, something episodes. And they started it because, at the time, they just felt like there was an opportunity for them to share their ideas to a larger audience using a media, which is video at the time that their customers would really be drawn to. And they did the show at 9 pm. At night, they drank and they burst on air. And they got a lot of people saying more to Chris than to him, you’re making a huge mistake, doing this as it’s hurting your brand. But what they didn’t realize, and what they believed is that this is who they are, they’re gonna be real. 

He thinks a lot of people in and outside the industry, they hide all their scars, where they provide a fake facade and hope that it’s going to appeal to people. And the reality is that, growing a business, trying to market trying to build trying to recruit trying to retain, it’s as hard it’s messy, it’s ugly. They were just honest and open about that. In such a way where people who would watch the show, say, hey, he love your ideas, but even more than your ideas, he loves what you’re trying to do, he wants to be a part of it. It became this thing that just drove incredible growth for the organization because it was, represented the ethos of the Curaytor brand and if you look at the landscape today, there are just there are that many public founders meeting they hide behind their products or services like they’re very public and open. They’re and that’s just one of their superpowers. It’s what attracts people to the Curaytor brand. It’s what did in the beginning, right, and it certainly does to this day.

Building Curaytor

Approximately two decades ago, Curaytor embarked on a pioneering venture into the realm of digital content creation, driven by a steadfast commitment to innovation. Their journey, while spanning a considerable timeframe, remains pertinent today as a testament to the power of forward-thinking strategies in the ever-evolving landscape of online engagement.

At the core of Curaytor’s ethos lay a profound belief in the symbiotic relationship between innovation and growth, encapsulated by the mantra repeated by their CEO, Jimmy, to their team: “When you innovate, you grow; when you don’t, you don’t.” This philosophy underscored their approach to content creation, leading them to explore a multitude of video platforms, from established players like YouTube to emerging platforms like Blab and Facebook Live. Their aim was not only to disseminate content but to foster genuine connections with their audience, engaging in real-time conversations and soliciting feedback through hashtags and live interaction.

The Curaytor podcast emerged as a pivotal platform for their innovative endeavors, featuring a diverse array of guests ranging from industry luminaries such as Gary Vee and Tom Ferry to top-performing agents like David Acosta and Mark Spain. Each episode was meticulously curated to provide actionable insights and valuable perspectives, ensuring that every moment spent listening was an investment in personal and professional growth. This dedication to delivering unparalleled value to their audience fueled the podcast’s meteoric rise, solidifying Curaytor’s position as a trailblazer in the realm of digital content creation and community engagement.

Curaytor Launch

They launched Curaytor alive at Inman Connect in 2012, 2013. Brad Inman is one of the other people that they look to as a mentor and someone who’s helped their careers, both his and Chris personally, but also Curaytor. He gave them a shot and allowed them to sort of present that new kids in the block at Inman Connect. But he wanted to remind everybody that when they launched Curaytor, they didn’t launch it as a consulting service and a technology solution because they didn’t have any of those things. 

What they did is they launched it as a search engine for real estate conversations. The time they had all these different groups that they were managing tech support group, which has 15,000 members, the what should he spend his money on group which he like 20,000 members, and a few others and what other ones out there, and they aggregate all this data from Facebook. 

They scraped all this data and they put it into the database and then built a search engine on top of that to allow people to basically search for the most popular conversations that were happening with these groups. Someone might come in there and say, What’s the best CRM and they can cross 10 different groups, and they’d be able to display all those conversations.

Same day that they launched Curaytor, curating all these conversations in one place, the same day that they launched it. Facebook introduced something called Graph Search, which was basically the equivalent, which is you can now search Facebook groups, which you couldn’t do beforehand. There’s a famous article written by them by its publication called Pando Daily, and it’s called the Startup Blues, and the story of how Curaytor built this product and launched it the same day that Facebook introduced a search tool. 

They had really no choice, but to shortly thereafter, pivot the organization towards not being a search engine, but now being a professional service that helped people with their marketing and advertising. Then they slowly over time, began to build technology. They started with using everyone else’s tech and bringing it together. They were effectively the ones were plugging everything in to make sure it worked for people. That was their initial business model, professional services, managing your kind of tech stack and your marketing. And it wasn’t for quite some time or began to build their own proprietary technology.

Curaytor’s Technology

Around the same time as their technological endeavors began, Curaytor recognized the pivotal role of content-rich websites in engaging consumers. This realization spurred the development of their initial service, Marketer, wherein their adept marketers crafted and disseminated compelling content across social media and email platforms, fostering client retention and audience expansion. This service garnered substantial success, embodying Curaytor’s ethos of high-quality, consistent marketing as a catalyst for real estate business growth.

Central to Curaytor’s ethos is its vibrant community, characterized by a commitment to collaboration and a rejection of the myth of automation for efficiency’s sake. Instead, members like Veronica Figueroa and Jason Cassidy exemplify a culture of diligence and innovation, eschewing shortcuts for hands-on dedication to their craft. This ethos permeates throughout the Curaytor network, fostering an environment where sharing ideas is encouraged, and ambitious goals are embraced, driving continual business evolution and success.

Tips in Starting a Real Estate Team

New agents venturing into the real estate arena often underestimate the challenges of going solo, according to Jimmy. He stresses the vital importance of aligning with a supportive team or brokerage. For Jimmy, a great brokerage ticks several boxes: rockstar admin staff to handle non-revenue tasks, a leader who’s not overly immersed in production but can provide mentorship, and a robust tech stack including CRM and effective marketing tools.

Furthermore, Jimmy advises new agents to prioritize growth opportunities within the team, seeking evidence of their ability to elevate agents from modest to substantial transaction volumes. He dismisses fixation on commission splits, emphasizing the significance of support and mentorship over a higher split elsewhere. To Jimmy, the real value lies in a supportive environment conducive to growth, rather than fixating on immediate financial gains.

What’s Next for Curaytor?

Jimmy’s journey from co-founder to CEO epitomizes the shift from wielding power without responsibility to bearing the weight of accountability for every facet of the business. As he reflects on this transition, he delineates the allure of co-founding, where autonomy reigns supreme, against the pragmatic demands of CEOship, where necessity dictates focus.

Over the past two years, a formidable leadership cadre has been assembled, comprising individuals like Tim Harvey, a former Marine Corps major, who spearheaded operational enhancements, and Tricia Turk, a seasoned Director of Customer Success. Bolstered by strategic acquisitions, such as the recent addition from Toronto, boasting top-tier engineering talent, Curaytor’s trajectory underscores a steadfast commitment to a singular mission: attracting more listings.

Central to Curaytor’s vision for 2022 is an unwavering dedication to mastering the art of listing acquisition, eschewing the trend towards all-encompassing platforms in favor of specialization. Understanding that market dominance hinges on controlling the listings landscape, they’ve harnessed data as their linchpin.

Through the acquisition of Four Walls, a data-driven venture founded by ex-Microsoft engineers, Curaytor augments its arsenal with refined insights into effective marketing strategies. In the words of Andrew Yang, data may be the new oil, but without refinement, it remains inert. Armed with this metaphorical refinery, Curaytor aims to distill raw data into actionable intelligence, charting a course towards sustained growth through software and services tailored to their singular objective: empowering top teams to secure more listings.


For anyone who has read the book measure what matters by John Doerr. It’s a framework which objective and key results and what he will say is this whatever structural organizational framework you use to establish your goals, the single most important thing this is a Steven Covey quote is to keep the main thing the main thing.

He meant that is if your organization has 25 different initiatives, all have which make complete sense. But the reality is, is that creates chaos yellow surface. For their, what they had to come to a consensus on was to use the leadership because they were just in Boston together for three days. Us on together say what is their primary function? Why do they exist? Can you tell the concept?

It’s and then you look at that say, okay, you’re in customer service, how would the function of your job be to enable customers to get the most out of Curaytor? How do you do that through this lens? Yeah, you help people, you know, on one-to-one calls on group coaching or mastermind help them attract more or less.

Jimmy thinks, whether whatever, whatever framework you end up using, because there’s a bunch of different flavors to it, it’s the main thing is to keep the main thing, the main thing, make sure that every meeting, you start getting with it, make sure you’re communicating as a leader, often to the point where you’re sick of hearing yourself say it, that’s when they really begin to listen. That is the type of consistency and focus from the top that any organization needs to be successful.

Connect with Jimmy

Follow Jimmy Mackin on Instagram where he shares advice, tactics, tips on how to grow your real estate business.

To listen to more of our podcast episodes, visit The #RealtyHack Podcast Page. The #RealtyHack Podcast is also available to listen to on SpotifyGoogle PodcastsApple Music, and your other favorite podcast directories.