Caroline Hobbs - Bringing Silicon Valley Tech To Real Estate


Having a mom who was a successful Realtor, Caroline Hobbs has set a goal to transform the process of finding homes and making it an enjoyable journey. Living in Silicon Valley, she has a prime seat to make that happen. Caroline is the visionary founder and Chief Broker of Reward Realty, established in 2013. She works closely with families and investors to deliver memorable experiences while helping them save money,time, and stress. She's also developing a new technology to help disrupt how agents, admin, and clients navigate a transaction and bring all parties together to create a client-first culture.

In this episode, you will be able to:

  • Learn how Caroline was able to adapt to real estate industry changes to help create success for herself.
  • Hear how Caroline was able to grow and sustain a profitable real estate businesses.
  • Simplify technology for efficient real estate operations.
  • Identify ways that you can harness your existing skills to transfer into real estate success.
  • See how embracing teamwork and growth opportunities can help you find success in real estate.

The key moments in this episode are:
00:00:00 - Starting Reward Realty
00:03:27 - Changes in Real Estate
00:05:42 - Challenges with Technology
00:10:24 - Building Strong Habits
00:13:58 - The Power of Teams in Real Estate
00:16:30 - The Flexibility of Real Estate
00:18:42 - The Wealth-Building Potential of Real Estate
00:20:45 - Balancing Responsibilities
00:23:34 - Real Freedom Investor Agent Tribe 










🎧 Apple Podcasts:
🎧 Google Podcasts:
🎧 Spotify:

👉 Facebook:
👉 Instagram:
👉 TikTok:
🏠 Minnesota Real Estate:

Caroline Hobbs
And so I went out on my own and started reward realty. When I started it, I like to think that I was creating an agents brokerage, and I still feel that way. It's been about 15 years that I've been in business. And so in the last 15 years, we've seen huge, huge changes, not just in the market, but in the way that agents and brokerages make money.

Mike Swenson
You welcome to the REL Freedom show, where we inspire you to pursue your passion to gain time and financial freedom through opportunities in real estate. I'm your host, Mike Swenson. Let's get some REL Freedom together. Hello, everybody. Welcome to REL Freedom real estate. Leveraged freedom, talking about building time and financial freedom through different opportunities in real estate. And today I'm so excited. We're going to share Caroline Hobbs, and she's talking about her journey going from being in real estate to leading a brokerage, also having her hands in some technology tools and then also investing a little bit herself. And so this is the cool thing about real estate, is you get to pick and choose what you're involved in. It's an entrepreneurial playground, and so everybody can make it whatever they want it to be. And so we're excited to hear more about your journey. You are the chief broker of Reward Realty and so would love to have you share more about your background in brokerages, why you started reward realty, building that, providing great value add for agents, and as we know, now is a very different time in real estate and providing a great platform that people want to be a part of, attracting people to be a part of that, and kind of executing what you want to do in life through helping other people. And so would love to have you share more on this episode. So welcome to the show. We're so excited to have you.

Caroline Hobbs
Thank you for having me. Yes, I started reward realty about ten years ago. It was ten years actually, this past April, and I came from Keller Williams. I was trained by their internationally recognized number one agent in the Palo Alto office. Palo Alto is right near Stanford, so there's a lot of money in that area, a lot of investors. So anyway, I started working on her team. I hosted open houses, worked in the office, I worked as her admin and took care of her database, which this is prior to realtors ever having databases. And she had one of over 10,000 people. And so I really learned how to organize people early and understand how to use that data and converting them into actual transactions. Ultimately, after going out onto my own as an agent, still with Keller Williams I've always been one of those people that's kind of an outside the box thinker. So anytime people put constricting boundaries on me with what I can or cannot do, especially when it comes to my business, it's not something that agrees with me. Well. And unfortunately, there was a lot of corporate ties and ways of doing things that I was just not pleased with. And so I went out on my own and started reward realty. When I started it, I like to think that I was creating an agent's brokerage and I still feel that way. It's been about 15 years that I've been in business. And so in the last 15 years we've seen huge, huge changes, not just in the market, but in the way that agents and brokerages make money, in the way that they learn. It used to be that the brokerage, 30 years ago you had to go to a realtor to purchase a home because you needed to get the list of homes that were available. Then we had Internet, and brokerages were still the main source of training. You couldn't just go learn online how to be a realtor. There weren't YouTube channels left and right on marketing your business and scaling your business. And so I really wanted to create an atmosphere where people could make a business that reflects them. I think that some of the most successful agents I know, a large portion of their transactions will come from sphere marketing because they've helped somebody and then they get referred or their kids soccer team or whatever. And so I've just found that teaching agents how to harness these skills that they have already built into them, teaching them how to lean into their sphere, teaching them how to do online marketing, teaching them how to really grow and scale their businesses to be profitable. It's something that I've really just become very passionate about. There's a lot of different theories out there on how you should be doing those things. For me, it's always come back to the systems, and I know that you have a little bit of history and working in the background with the admin systems and things like that. And so I think one of the reasons why a lot of realtors struggle is there's so many shiny objects to grab all the time. And then you also have these super systems like KVcore or chime, and they're great. But in all honesty, I think nowhere else is it more prevalent than in technology where a master of all is a master of none. And so I think it's very difficult for realtors who are not necessarily the most tech savvy people to get up, run a business, scale their business, grow their business, and have to wear hats for 15 different professions. We're coordinators, we are project managers, we are photographers. We make it all happen. And so that's what my team has been working on for the past year, is really developing some strong systems and building some proprietary software in order to help agents organize their businesses and scale.

Mike Swenson
You mentioned that chasing shiny objects, it's a hard thing. And for agents, yeah, because most agents aren't gifted in knowing and understanding systems, it's hard for them. You're right. There's a lot of tools out there that can do a lot of amazing things. But for agents, if they're not able to log into a system or even figure out the most basic thing to use, it's kind of pointless. And so I would always tell agents, start out with a spreadsheet, it's okay, you've got your contacts in a phone, which is a good start, but you've got to get them down somewhere. You can then do something with it. But, yeah, so many agents get tripped up because, yeah, these technologies can do 87 different things, but they don't really know how to make a call, log some notes for a call, and figure out who they need to call next. And so you've got to start small and build those systems. And, yeah, large brokerages sometimes struggle with being able to teach those basic fundamentals and to be able to help people out with what they really need when they need it.

Caroline Hobbs
Yeah, well, I think part of that also is a lot of real estate systems are not built to work together. And so you'll have your brokerage systems, and then you'll have a CRM, which has its own way of recording and doing things. And then maybe you have something else that you're using. And so I think, just like anything else, the more steps you add into the equation, the more kind of falls through the cracks. And the more times that you're asking people to duplicate efforts, the more they're going to build a resistance against using it. And so that's kind of what we've taken to the core of our platform, is we have built initially off of follow up boss as a CRM. And honestly, the reason I chose it is, in my opinion, follow up boss is a blank rolodex. They don't have a lot of the bells and whistles as a lot of these larger CRM companies do, but it has an open API that makes it easy to connect tools to and makes it easy to customize to your business. And in our instance, it makes it easy for us to customize versions of their software to run a forward facing client, portal and transaction manager all through the system in synchrony.

Mike Swenson
So for an agent that works in your brokerage, how are you helping them to see the value of this tool for maybe a tech averse person? Now, I will say you're in Silicon Valley, so you probably have more technology savvy people than most areas of the country. But for agents that do chase shiny objects, how do you help them? See, like, this isn't just a shiny object, this is something, a foundational tool that you can really build your business and grow your business off of.

Caroline Hobbs
Well, I think it's breaking it down and making it simple. The first thing I do when I sit down for an agent training and bringing them onto the systems is we have steps, we have it all outlined. We use Monday to kind of help us onboard people and we have it broken down. So first thing is putting in your CRM, making sure all the information looks good. The next, we help you set up the lead flows. So that way, as new people come in to your systems, they automatically get assigned onto different touch points and different nurture systems. We have a marketing company within our office that helps us put out newsletters and put together emails about new listings within the office and things like that. And then we use a few different systems in the background like Homebot and Ylopo, to provide the listing alerts, to provide home valuation data, and to kind of help stay top of mind with the people that are in our database and how I get people to adopt this. I show them the value and then I break it down into what I expect from them every single day. And follow up boss makes it so easy for me to do that because each day they send out a hot list and that will show you all of the new leads that have come in and have been assigned to you, and it'll show you any leads that come in and are assigned to you where there are tasks that need to be completed. Basically, my agents are only required to check their email daily, pull up their hot sheet, and make the calls that are assigned to them for that day. And by having it organized with different follow ups and tasks and things like that, it makes it easy for my agents to not feel overwhelmed by seeing that they have 150 clients that they're currently rotating and calling and following up with. It keeps them engaged with them and it keeps it manageable.

Mike Swenson
Yeah, and I think that's the thing is helping agents to be able to focus on a few things and do it really well versus having to do a lot of different things and just there's so much time that gets wasted between bouncing from thing to thing to thing to thing to thing. And if you're able to just focus on a couple of things, do it really well and build those skills over time, that's going to make a great long term agent, versus I'm trying to do all these things, and if you try to chase two rabbits, you'll catch none. So how do you really build sequentially and help them have the great skills to grow their career? So for the agents that you're working with, do you like to work with newer agents or do you like to maybe have agents that have had some experience and kind of see maybe they don't know what they don't know and you can really help take them to the next level or what's really kind of the fit for people that you like to work with at your brokerage?

Caroline Hobbs
I think it's a mix of both. Honestly, I'm looking for people that are hustlers. I want people that want to get in there and work. I want people that want to be successful. I don't want to waste my time training somebody and setting them up and getting them going. For them to just say, I don't feel like it today, I'm going to go do this instead. It's not helping anyone. And so I think that one of the things is building strong habits from the beginning. That's why I say it depends on the person. If they really want it, then they'll build new habits. But building those healthy habits and not correlating negative feelings around it. I know a lot of teams will have new agents come in and sit down and just sit at the phone and call for hours and hours and hours. And it's like, if you made me do that, I would then dread calling clients. And I don't want anybody to start the career with saying, oh, I hate making cold calls. I'm like, suck it up, buttercup. You've got these ten people to call today, or you've got these seven people to call. Whatever the hot list says for the day, that is what they need to be focusing on. And that's what we try and keep it positive and keep them focused on just the day's tasks, not the overall daunting month worth of leads.

Mike Swenson
So I think about when people come to real estate, they come from another industry. Maybe it's a sales industry. Or something like that. And I've seen agents be short sighted in their thinking, where they look at, hey, I made x amount of dollars over here, and I didn't make this my first year in real estate. And so now maybe I'm going to go think about going back to that industry. And I tell people there's so many great things that can happen. Year two, 3510 20 in real estate. And obviously, I love talking about investing in real estate and how that can be a future thing where you can spend your time, but showing that longer term vision, because an agent might just look at their pocketbook or their bank account for year one and not see, like, oh, when I'm in real estate, I can build year over year and have year two be two x, three x or four x, and continue that for however many years. Do you help them see the bigger picture and how, yeah, I might suck really bad that first year, two or three, but it's going to get a lot better the more that I focus on my craft and get better, I.

Caroline Hobbs
Think that's challenging for a lot of people. There's several new brokerage models out there where they're giving salaries, and you get kind of like a bonus at closing. I have an agent that's been with us four months now. She's on our team. For my team members, we provide all the leads for them. I spend about $20,000 a month in marketing and provide all the leads to my team, and then everybody's on a 50 50 split. And she came from a brokerage of that type where they paid her a salary and she hosted open houses and did all these showings and maybe did a thing or two, but was really just salaried employee didn't get to sell. She has closed two transactions so far with just over $4 million in volume in the three months that she's been with us. So it can happen. You have to focus, and I think making sure that you align yourself with the right team. Teams, I think, are a great stepping stone for agents. It's the reason why I have one within my brokerage. So I run the team as well. And I do that not because I want the higher splits, because I want to empower these agents to get the confidence to transact, to understand what it's like to follow up with online leads, to learn and build those healthy habits so that eventually they can graduate from being on the team and become an independent agent within the brokerage and potentially even start their own team as well. So really, I've always thought of my team as kind of a stepping stone for agents as they move to become more independent and more senior.

Mike Swenson
Well, I think it's great that you're doing that because not everything's going to work for the rest of your life, and so you have to provide a career path here and provide a larger vision because, yeah, teams are fantastic. I love real estate teams, and I think there's a lot of value, but not everybody's a fit for the team, and the team isn't always a fit forever. And so finding ways where you can help people along different stages of their career is really important. And in real estate, too, not taking it personal when somebody leaves a team or leaves a brokerage, because change happens. I would love to provide an atmosphere where people would want to be long term, but at the same point they might go, but they might come back, too. And it's no different than friendships. Sometimes you have friends that you're closer with for a while, and then you kind of lose touch, but then you come back and it's okay. And so real estate is a long journey and we need to be here and help each other out for the long haul. But, yeah, I love how you're addressing people at different stages of their career and helping them along the way.

Caroline Hobbs
Yeah, definitely real estate. I'm third generation real estate, so it's been in my blood and I don't really know anything different than that. When I started in real estate, I was still in college. So it's opened so many doors for me in life and has given me the flexibility to be at home with my kids when they were young and to be there and be class mom every year. So it gives me a lot of flexibility and freedom in that way, and it also opens the door to a lot of different opportunities when it comes to investing. I'm a part of the Tom Ferry networking group, top agents from all across the country. I go to probably three or four of his conferences a year and network with people, and it has opened the doors to a lot of different opportunities investing throughout the know. If you were to call me and say, hey, do you know anyone in Palm Beach, Florida? I say, yeah, I got a person for you. You know anyone in Phoenix? Oh, yeah, you're going to call Corinne de Blanc. It makes it more fun, too, and more collaborative, from my point. So last year, my family, my husband and I, we had an open heloc on our house. So we took that money and we put it into three different investment properties in El Paso, and we basically break even on them, but they will pay themselves off and eventually bring in additional income for us for retirement. So right now, between the duplex and the two single families, we make about 7500 a month in rental income. One day, when we go to retire, we're going to be looking at at least $8,000 a month in additional income, which is great.

Mike Swenson
And yeah, depending on people's appetite for risk, too, you can continue to pull out that equity, if needed, and build more and more. And that's the freedom and flexibility that real estate offers you. And not everybody is ready to invest right out of the gate. And you don't have to be a full time investor, but you can pick up a couple of properties along the way, or you can find something that stumbles across your plate, you can take advantage of that opportunity. And so because you've built skills in real estate and you've been in the industry for a long time, number one, you can recognize hopefully some good deals. And number two, take advantage of them. And then three, you can decide what you want to focus your time on, what's going to be the best use of your time, and the things that you're most excited about building. And so not a lot of people would be excited about building tech tools, but you are, and you're in a good spot to do that. And you can offer, and then if you want to spend more time doing investments, great. If you want to spend more time growing your brokerage, great. You want to spend more time working with clients, great. You get the power to choose that with the different spaces that you've invested your time over these last few years.

Caroline Hobbs
Absolutely. And 87% of the wealth in this nation is built through real estate, whether it's your primary residence or investment properties. So I think that if you ever have a time where you have an extra 15, 2030, $40,000 in your account, looking at opportunities where you can invest that, and maybe whether you're break even or making a small return, ultimately it's going to pay off in the long run, whether it's through equity growth or an income approach. I know for our homes in El Paso, I didn't buy it for equity growth, we bought it for income. But all three of those properties have gone up 15%. So we've probably made about $70,000 just in the past year and a half of owning these properties. There's a lot of opportunity out there, whether it's by chance or whether it's something that you're searching for. But I think ultimately, when you're looking at investment properties. Taking as much emotion out of the experience as possible has been beneficial for me. So much of it is just a numbers game and you can really think of it as being black and white. A lot of the investors I work with for flips and whatnot, they actually have an algorithm that they just type a few key metrics into hit go, and it tells them if it's a go or if they should pass on it very cleanly. And so I think just understanding what your goals are with your investments is really important.

Mike Swenson
Yeah. And that's a cool thing, is follow what you're passionate about. Pick something that's going to keep your interest and keep you excited moving forward. And there's lots of opportunities, there's a lot of different ways to make money in real estate. And so some people choose to do. If we're just talking, just investing, it's like some people flip, some people hold, some people do apartments, some people do storage units, some people do mobile home parks, some people like to invest in the city, some like to invest in the suburbs. There's lots of different opportunities. And you get to pick and choose what you're passionate about and hopefully find stuff that makes you money. I'm curious for you, how much of your time between the technology tools you're working on, being a mom and doing that, how do you divide your time up throughout the week?

Caroline Hobbs
That's a great question. My calendar is full daily, but we time block a lot. That includes making time for myself. So I know personally that I need to have an appointment with my trainer if I'm going to make it to the gym, meet Shay. So we do, as long as it's on my calendar. I show up and I have an amazing team. We have two staff members in the office that help support me throughout the day in making sure that I have everything I need for each meeting and that we're on track for the day. My email, I think probably the same as a lot of people. My email kind of regardless of the meetings going on, it's like a running to do list of things that need to be completed. And so that's where I really rely on my team to help support me. So that we're always providing the highest level of customer support. We're always providing support to all of our agents. And like, for example, my guy sitting right next to me, he is in charge of our media, so he films all of our trainings and things like that. So that way if our agents can't be there, we're still supporting them and able to add this to a library where they can go and watch it later and still get that valuable information and that valuable training. So lots of different levels.

Mike Swenson
I talked about this before. That's the cool thing, is you get to pick and choose what you want to do. I had interviewed somebody previously and they were kind of in their full time job and they were sitting there wondering if they were going to get let go because they heard there were some round of layoffs coming. And it's like in real estate, you can spend your time anywhere. It's not always income producing or the most productive way, but there's so many different things you can do. And I just love how you've created a path that's unique to you and you're changing it as you go and finding different ways to serve different people and ultimately having a vision of what you want to accomplish later in life and taking some steps today to make that happen. That's the beauty of real estate.

Mike Swenson
You and cheer you on along the.

Mike Swenson
Want to have some skin in the.

Mike Swenson
Thank you so much for coming on and sharing for people that want to know more about you or reach out to you or hear more about what you're working on. How can they do that?

Caroline Hobbs
Yeah, absolutely. Our website is and then is the name of our tech company. That website is not live yet, but probably will be in the next month or so. Until then, just check out reward realty.

Mike Swenson
Well, thank you so much for coming on and sharing your story. We appreciate it and best of luck as you continue to carve your path in real estate in the future.



50% Complete

Two Step

Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua.