Merging a 20-Year Real Estate Career with a Passion for Social Justice Through Race2Dinner
Regina Jackson is a dedicated mother, grandmother, and entrepreneur with a multifaceted career and a strong commitment to social justice. Married for 38 years, Regina balances family life with her professional pursuits, which include running Action Jackson Realty and co-founding Race 2 Dinner. With over 20 years in the real estate game, Regina transitioned her company to Compass in 2022, valuing its robust platform that enhances her service delivery. Regina’s career is marked by diversity and impact. Before real estate, she founded Mastery Inc., providing computer training to underserved communities.
Her journey also includes a significant role in anti-racism through Race to Dinner, a venture she launched in 2019 with Saira Rao. The initiative promotes radical honesty in discussions about race and has garnered attention with its New York Times bestselling book and the documentary “Deconstructing Karen.” Passionate about gardening, floral design, and reading, Regina finds solace at her family’s historic mountain cabin in Lincoln Hills, Colorado. Her personal and professional philosophy revolves around authenticity, radical honesty, and a deep sense of gratitude. Regina emphasizes the importance of community support and values personal integrity, mental health, and family. She believes in the transformative power of opportunity and is dedicated to fostering liberation and equity for all. Regina’s work and values underscore a commitment to improving lives and challenging systemic injustices, driven by a core belief in the inherent dignity of every individual.
Tell us about the path that brought you into real estate?
I’ve been in real estate for 20 years and real estate helps pay the bills. But I’ve had four different careers. I retired from the Bell System after twenty seven years and started a computer training company where I would go into disadvantaged communities and set up computer workshops. It was called Mastery Inc. I did that for about five years. Then a friend approached me and asked me to help her in a real estate business. I helped her get everything mechanized in her real estate business. Every other week she would say to me, “I know you’re going to get your license.” So after two years, I got my license and quit. I started my own company in 2009, Action Jackson Realty, and I moved it to Compass in 2022. Compass really has the best platform in the industry. I’m glad to be there. I have a team of five people, that includes me.
Then my last career is a business called Race 2 Dinner. I started that with Saira Rao in 2019. We’ve been called grifters and everything else. But there is a story, Saira ran for Congress in 2018 against a long-time incumbent, Congresswoman Diana DeGette. Saira ran on a platform of anti-racism based on the Trump era racism directed at brown immigrants. People south of the border were being caged. Muslims were not being allowed back in the country. So she ran on a platform of anti-racism. Every time she would speak, white women would line up to talk to her. And what they all wanted to say was, “I’m not racist.” Because Saira was courting votes, she would have those conversations. She’d pay for breakfast, lunch, dinner, cocktails, plus a babysitter, because she had two young kids. A friend of mine, a white woman, said, “I’m done with Saira, she hates white people, but if you can get her to go lunch with me, I would love to do that.” So I went to Saira, I was working on her campaign. She said, “No, I’m not doing that anymore. But if your friend wants to host a dinner, invite her white lady friends and you do it with me, I’ll do that.”
She hosted the first dinner. Saira calls it “White Women: The Broadway musical.” Then we held another dinner and we looked at each other and said, we have a business opportunity here. So we started Race 2 Dinner in 2019 and we’ve been going strong since then. We will be in Austin and in Baltimore this year. We’re currently talking to a theater group in the UK. It looks like we’ll be going back to the UK and Ireland next year. The conversations are radically honest. We encourage people to tell the truth. I always say, if I, as a black woman, have had to spend my entire adult life affirming myself and giving gratitude that I am enough, then white people certainly have to do the work of getting rid of their thoughts, their actions, and their beliefs around people who are not white. So that’s the premise we’re coming from.
What have you noticed since you started doing the Race to Dinner in 2019?
We have a book called White Women: Everything You Already Know About Your Own Racism and How to Do Better. It’s a New York Times bestseller. We’ve sold over 100,000 copies and we’re still going strong. And we have a documentary called Deconstructing Karen. It can be seen on Prime, Tubi (for free), and Vimeo. When we started this business, there was a white woman producer out of LA named Patty Specht, who was watching our work. She called us and she said, “I want to do a documentary about your work.” And we looked at each other, we said, “Yeah, yeah.” Next thing we knew, she was here with a full crew ready to document the work we were doing. That documentary is out there and available. It is an actual dinner. She did a casting call and all these women at the dinner answered the casting call and that’s how they were chosen. This work on anti-racism is my heart. I have children and grandchildren. I can’t afford to not be in this work. It’s not an option for me. White women, white people have the privilege. It’s not a privilege if you’re not white.
Would you say women in your daughter’s generation are more empowered?
Absolutely. I also have a course that I’ve developed called Race 2 Self-Actualization. It is a course that helps people identify and create their own life plan. You decide what your purpose is. You decide what your vision for your life is. When I say vision, I mean, what do you want to do? Be? And when I say be, I mean, characteristics. What are those things? You develop your values. When you act out of values, you are consistent. We’ve lost a lot of support around supporting Palestine. But you know, if you are in the work of liberation, abolition, and freedom for all, you don’t say, “Well, these people don’t matter.” Everybody matters. That’s what race to self-actualization helps people define, who you are on your own terms and how to live by your own values and goals.
Would you call yourself a humanitarian?
An abolitionist, trying to abolish all the isms, all of them. Let’s get right down to we’re all human beings, we all deserve dignity and respect and a safe place to live and work that has value and allows us to maintain a decent life.
What advice would you give to your younger self?
Affirm yourself. Affirm yourself every day, and give gratitude every day. Those two things really allow you to be who you are. Because the more we’re grateful for what we have, the more it comes into our lives.
Tell us a little bit about Compass. How long since you’ve joined their group?
In 2022, I took my company into Compass. I love the Compass’ platform. I have been recruited a lot around my career in real estate. I never really felt the need to take my company any place else because when you do that, you give up part of your commission. Compass gets a part of my commission, but what I get back from Compass– I used to pay $500 to do a video to send out to my customers. It’s part of Compass’s platform. So I can send out a video every month if I want, every week if I want, to all my customers. And I have a database of over 4,000 people. So Compass gives me the tools I need to be a very effective realtor.
What are the current locations you focus on when it comes to real estate?
I basically do the Denver Metro area. I feel like technology has allowed us to have a larger market. As a seller’s agent, you may have to know the market, but pretty much the Denver Metro market looks a lot alike. All the different cities and communities look alike. As a buyer agent, it’s really interesting. We used to have to find properties for our buyers and show them. Now buyers are calling you and saying, “These are the properties I want to look at.” It’s made being a buyer agent much more easy and convenient. So you don’t have to show them properties that you think they may like. I think what’s really taken a toll on the market is the interest rates. Prices have gone up. Denver has really become an unaffordable place for a lot of buyers. But we’ve got all these little suburbs around that people can still afford to buy. I have a 2.5 interest rate on my home. Why would I sell that to get something smaller that’s going to cost me more money? That doesn’t make any sense.
I believe in radical honesty. To people who say, “We want to sell our house,” I go “Okay. You have this 3% interest rate. They’re building smaller homes. Why would you give that up to go into a smaller home that’s going to cost more money? That doesn’t even make any financial sense to me.” That’s part of our job as realtors, especially if you’re in an agency agreement. You represent your buyers and sellers as their agent. You are giving them your very best real estate advice about the market. I don’t try to be a financial person. I have really great lenders that I will refer my buyers to. And I choose the lenders I choose because they’re good at what they do. Nothing’s worse than showing up at the closing table and your lender doesn’t have the loan approved. You get one time with me, that’s it. Because the people I suggest to my clients represent me.
If I’m giving them someone who can’t deliver, that’s on me. I want my clients to be delighted in the service they get from the Action Jackson team. Customer service is number one. I came out of the Bell System. That was AT&T. I started in customer service. We were trained from the very beginning that when you excuse yourself from the line, you get the customer’s permission. When you come back, you acknowledge, “I’m back.” Just top customer service. It’s really hard nowadays because you will call these companies, you get on hold, you don’t know if someone’s there or when they return., Always in the back of my mind is that customer service representative that I started my career as.
What do you want to see for Race2Dinner?
I want to see white women really understand that all of our liberation is connected. That they can’t be free from patriarchy, misogyny, any of the things that we deal with unless all of us are free. We’re in this together. I really want white women to recognize that. I think they have an opportunity to say either, “I want to continue to be capping for white dudes,” or “I want to put my own liberation first.” It’s a for-profit. We started as a for-profit. This work is not easy for black and brown women and we burn out. They need to pay us for our labor. All of our suppliers and the people we use are black and brown women.
How do you find inner balance?
It’s the affirmations and the giving of gratitude. I know who I am, so what anybody else thinks about me or writes about me or says about me doesn’t matter because I know who I am.
Are you a faith believer as well?
I’m not a religious person, but I am a spiritual person. I believe that there is a creator and that my job here is to develop myself, create the person I want to be, and to help other people do the same thing. That’s what I believe. I think there’s really only two emotions. You’re either acting out of fear or you’re acting out of love.
How do you set yourself up for a successful day?
I’m an introvert. I know people find that hard to believe. I like to get my coffee and sit down and spend about an hour just being by myself. Part of my affirmations are songs that I listen to, songs that uplift me. I have four songs that are part of that, I do my affirmations, I drink my coffee, and then I’m ready to go. I lift weights two times a week, one’s for upper body, one’s for lower body. It’s been too hot to walk. If the weather were decent on the days that I don’t lift weights, I would go out for a walk. I try to meet friends for coffee or lunch, or people I relate to. I generally have at least two or three Zooms a week that I do religiously. When I’m not doing that, I’m working on promoting both of my businesses. Oh, and picking up grandkids. I’ve been picking up grandkids from school now for 22 years.
What are you calling in currently? We call it active manifestation.
I really want us to learn how to just love each other. And if you can’t love somebody, then look at them and say, “How is their behavior hurting me?” Because generally, it isn’t. My 84-year-old aunt came to Christmas Eve dinner and she made the comment, “I just hate when those gay people show affection in public.” So my question was, “How does that harm you?” It doesn’t. I said, “Okay, you don’t get to be homophobic in this house.” I want us to understand that if people are living their lives and they’re not harming you, leave them alone. Leave them alone. How hard can it be to mind your own business and let people live their lives? I want people, when they see other people being harmed, to speak up. It can’t be that hard to say, “You know what, I’m not okay with that language,” or “I’m not okay with that behavior.” Just protect each other. That’s why we’re here.
What is your superpower?
My superpower is authenticity. What you see is what you get. I was at the farmer’s market with my daughter. They hold it in a parking lot, so asphalt. There’s all these people walking around with dogs and it’s like 80 degrees. I’m saying to people, “It’s too hot to have your dog here.” My daughter goes, “Mom, mind your own business.” I’m like, “I’m not minding my own business, these dogs can’t talk. It is too hot. If they want to take their shoes off and walk around barefoot, fine. But it’s too hot for these dogs.” That’s who I am. They always say if you ever see a dog lock in a hot car, you should tell someone. You should always report that because some people don’t understand how hot it is. A lot of women are scared or still have fear from using the power of their voice. You have a voice for a reason. Speak up.
Were you one of those kids that always spoke their truth?
Yes. There’s nine of us. I have an older sister and then a brother that’s two and a half years younger than me. I was always the child who was taking care of them. Nobody picked on them because I was always out there taking care of them. My older sister is pretty passive. She would say, “Well, hit me,” and somebody would hit her, and I go, “Oh no, you can’t hit her.” I have four brothers and four sisters on my mother’s side. My parents divorced when I was a babe in arms. I have another sister and three brothers on my father’s side. That’s why I have to be in this anti-racism work. I’ve got nieces and nephews and great nieces and great nephews all over the place.
That’s really important for black people because we are so far behind in this society. And people talk about reparations, I don’t believe we’ll ever get reparations. If we can support HBCUs and we can cultivate places that help black children to have opportunities, that’s what I want. Because I think when you have opportunities, you can go far, but we’re so limited in the opportunities. I think that’s what’s important. My work at the Bell System started with a consent decree. AT&T was sued for racism. I was at the right place at the right time and I got that opportunity.
Sometimes you have to see it to believe that it could be possible for you. I happened to work for the first black officer at Mountain Bell. His name is Bruce Bond, and he was head of strategic planning. I was a first-level manager, my second-level manager retired and they brought a new woman in. At that time I was on the board of the YWCA downtown and we met once a month. I came into the office one day and my manger said, “I didn’t see you at your desk, where were you?” I said, “Well, Kathy, (that was our receptionist), she knows I have this monthly meeting”. She says, “From now on, when you’re not here, I need to know where you are.” I said, “Do you mean when I’m not in the office or when I’m not at my desk?” She said, “Yes.” I marched into Bruce’s office. I was going to go complain. He says Regina, “I have a second-level manager job available. I want to appoint you to this new position.” I had an office with a couch in it. Me and my black girlfriend would sit in there and giggle — because this was in the early ’80s.
How did you step into this role of leading your own company and your brand?
My last boss at the telephone company is still my mentor. He’s a white man and he is a really special person. He basically promoted me to a director, supporting him directly. Before I started working for John, I kept getting these calls from his secretary saying, “John Kelly wants to meet with you,” but then she’d call and cancel the appointment because he had something else to do. So I go to my director and I say, “Why does John Kelly want to meet with me?” And he said, “Well, he wants to offer you a job.” So I finally met with him. As I’m in the meeting, he’s packing his bag to go to another meeting, so I left him a voicemail message and I said, “John, thank you, but I’m not interested.” He called me back the next day. He says, “Regina, I thought we got along so well.” How do you tell your executive vice president and general manager no, twice in two days? So I took the job. He was, and still is, an amazing human being. I’m glad I got the job because I learned so much from him. He gives and gives.
Now, one of the things I knew is that I didn’t want to be a corporate executive. I didn’t want that life. They’re always busy, they’re flying around. We used to fly on a private company jet. I’d get on there at six o’clock in the morning and I’d go, “You don’t talk to me and I won’t talk to you.” But I knew I didn’t want that life. I always liked the idea of working for myself. When I left the Bell System, the work I had been doing was with those community centers so I continued that work and wrote training to train people how to use the computer. This was in the early ’90s and the internet and computers and everything were coming in. I put together classes. When I shut that down, I told you my friend approached me to help her mechanize her real estate office. So I knew I could do the work.
I like being my own boss. I’m a Capricorn. I don’t want anybody telling me what to do. So I went the entrepreneurial route. I’m like, “Okay, I’m going to be my own boss and I’m going to tell other people what to do.” I have great intuition and I have never been let down by my intuition. I have been let down when I haven’t followed my intuition. I have great intuition about people and everything. When you’re acting out of personal integrity, your life lights up constantly because you have nothing to hide, nothing to show, this is what it is. You’re like, “I know I’m clean. What you see is what you get. I’m not going to change my values for anything or anybody.” It operates out of values. I value family. I value integrity. I value mental health. I value physical health. I live that. I value community. You take that everywhere you go, into every brand that you build.
What do you have coming up in terms of events and projects?
We’re going to be in Austin, Texas, and then in Baltimore, Maryland in October with Deconstructing Karen. We’ll be showing the documentary and having talkbacks with the audience. Tickets are being sold on Eventbrite. We’ll be telling the radical truth as we see it. I want to give a shout out to my partner, Saira Rao. She’s an East Indian woman and she’s the one who ran for Congress. We don’t agree on everything, but I come from a place where you get to be you. You are not me and I’m not you. But in terms of doing the work, we’re solid. We have this big election coming up. I mean, I love Kamala, but you know what, we’ve got to stop killing Palestinians. Sorry, we have got to stop killing. That’s my priority. Congo and Sudan and every place else where the United States is complicit in murdering innocent people, it’s got to stop. At the same time, I would love for a woman to be at that level too. I’m already out there on social media and putting those demands. I’m like, “Come on, girl, you gotta stop this. This is not okay.” That’s who I am, authentic all the time.
What are your words to live by?
I believe that I can have everything that I want, but it may not be all at once. Every day and every night I give gratitude. That’s part of who I am. I am thankful for my family, for my community, for my work, to do work I love, for opportunities. I’m grateful to be having this opportunity with Goss Magazine. I’m grateful.
Race2Dinner Vision :
The Race to Dinner is committed to radically honest conversations about racism. Radical honesty is our number one value. Our vision is liberation for everyone. Visit race2dinner.com