May 9, 2020

JF2076: Selling Million Dollar Real Estate With Cynthia Cummins


TRANSCynthia is the owner of Kindred SF Homes and she has 33 years of real estate experience. The houses she deals with have an average price point of $1.5 million which can create high emotions and interfere with your decision making. She shares what has helped her sell multiple million-dollar homes through a process of creating, nurturing, and continually finding new ways to build strong relationships which in return create valuable referrals.

Cynthia Cummins Real Estate Background:

  • Owner, Kindred SF Homes. 
  • From San Francisco, California.
  • With 33 years of experience in Real Estate. 
  • In the last 3 years, she’s sold $80M in San Francisco Real Estate
  • She has a popular blog called Real Estate Therapy where she writes about her passion, Secrets about how transaction and transformation meet in real estate.
  • Say hi to her at  
  • Best Ever Book: Lincoln and the Bardoe

Click here for more info on


Best Ever Tweet:

“Having a bigger vision for people and a longer-term view is what makes all the difference” – Cynthia Cummins


Theo Hicks: Best Ever listeners, welcome to the best real estate investing advice ever show. I’m your host, Theo Hicks, and today we’ll be talking with Cynthia  Cummins. Cynthia, how are you doing today?

Cynthia  Cummins: I’m doing really well, Theo. Thanks for having me on today.

Theo Hicks: Oh, absolutely. Thank you for joining us, I’m looking forward to our conversation. Before that, let’s give a little bit of background on Cynthia. She’s the owner of Kindred SF Homes and is based in San Francisco, California. She has 33 years of real estate experience, and in the last three years she sold 80 million dollars in San Francisco real estate. She also has a popular blog called Real Estate Therapy, where she writes about her passions and secrets about how transaction and transformation meets in real estate. You can check out her blog at

Cynthia, before we begin, can you tell us a little bit more about your background and what you’re focused on now?

Cynthia  Cummins: I have been selling residential real estate in San Francisco for more than 30 years, which is kind of shocking to me as I say that out loud. I went into the business thinking “Oh, I’ll give this a try”, and now here I am, three decades later, still doing it.

I woke up this morning, I have a significant listing that just debuted this week. It’s a 4,5 million dollar Victorian, here in one of the nicest neighborhoods in San Francisco, and it is what I’m waking up with every morning – thinking about it, worrying about it, strategizing about it. So this was on my list for today.

And what I’m trying to do is follow my own advice about thinking about that listing and the work I have to do around it in a more holistic way, so that I can give myself a break from all the worrying and the craziness that can go along with it.

Theo Hicks: So let’s talk about that. It’s not every day that people have a multi-million-dollar listing and I definitely wanna talk about more the tactics stuff. We can take a step back and  talk about this advice that you have, about approaching real estate in general or specific projects in a more holistic way… So do you wanna walk us through what that means, how that looks in your day-to-day life?

Cynthia  Cummins: Okay… So I’ll kind of think about the listings that I have on my plate right now. There always seems to be a theme around the listings that I have at any one time, and the theme right now is people who are in the middle of huge transitions, moving from one stage in their life to another after owning a home for many years… And it is like lightning has struck their whole being. Everybody who’s doing this is kind of in bits and pieces, and trying to move forward in a very courageous way. The stakes here in San Francisco are so high… I don’t even know what the median house  price is right now, but I think it’s around 1,5 million. So just to show up, we’re talking about big numbers… And with big numbers come big emotions, and I have to figure out always how to manage my own as I stand and hold space for my clients to go through what they’re going through. I don’t know — did that make sense?

Theo Hicks: Totally. And actually, I can completely relate to what you’re talking about right now, because me and my wife were actually going through the same process from moving across the country for a new job. So yes, it’s definitely very stressful, but I would imagine the stakes are a lot higher when we’re talking about price values that are 4-5 times higher than we’re looking at…

So what’s been the conversations like? For example, you’ve got a person who’s going through this huge transition… Maybe talk specifically about the one you’re having right now; you’re listing it for 4,5 million dollars; I’m sure it takes a long time to prepare and sell a house that large, and that comes with extra stress on their part as well… So what are some of the things that you are doing with them, saying to them, to help them try their best to alleviate this emotional stress from, as you said, having their whole entire being struck by lightning?

Cynthia  Cummins: The “struck by lightning” phrase came to me because every now and then I will pull out a deck of Tarot cards and look at them, just for fun, to see what they might say… And there’s a card in the Tarot deck called “The Tower.” The Tower is actually an image of a tower being struck by lightning, and people sort of falling off the ramparts, and the thing is aflame… And it’s a really scary card. If you get that card, it can make you feel really nervous. But it is such a  great metaphor, because really, when you’re struck by lightning, all kinds of possibilities open up, and it maybe means that yes, this is really uncomfortable right now, but you’re heading for something new and something that’s really gonna serve you better.

So when I’m talking with my clients who are in the middle of having their tower dismantled, leaving one home for another, or leaving one part of the country for another, retiring, getting a divorce, whatever the situation is, I try to help them keep their eye on the fact that yes, this is really uncomfortable; it takes a lot of work, it takes a lot of focus, but you’re moving towards something that is going to improve your situation, usually.  You’re heading for something that’s going to be better.

Theo Hicks: Yeah, I really like that metaphor. Moving to more specifics on this deal – or you could talk about a different large deal like this, because I was browsing through your website and saw that you do deal with these multi-million-dollar deals… From your perspective, besides the more emotional side of the deal, what else is different between these larger deals and the smaller deals?

Cynthia  Cummins: Well, I must say that everybody, whether they’re selling a million-dollar condo or a six-million-dollar house in Hayes Valley here in San Francisco, their house is big to them. So it doesn’t matter what the price point is, everybody’s concerns are really similar. So I repeat it again and again. But I think that for everybody, but especially in this higher price range, when you are a wealthy person and one’s idea of luxury begins to change… Luxury becomes meaning. When you get to a certain point in your life, everything’s Jake, you’ve got a good job, you’ve got good income, the family is fine, you aren’t thinking so much about survival as you are thinking about the quality of your life, and is there meaning in your life. So that’s going on with these multi-million-dollar sales.

At the same time, that person is also concerned with really nitty-gritty stuff, like “Is there a powder room on the main level, and if there isn’t, how am I going to get one?”

Theo Hicks: Okay, that’s something else I wanted to talk to you about… So let’s say  I’ve been an agent for a few years, and I want to eventually build up to the point where I’m representing clients in higher and higher price ranges. What are some of the things  I should start doing today, so that in 5-10 years from now I am where you are?

Cynthia  Cummins: I think that there are all sorts of resources and coaches and guides for how to build one’s business, how to try and aim for a higher price point, and that sort of thing. There’s all sorts of different approaches to marketing. But the thing that I keep coming back to is that pretty much 95% of my business comes directly from sphere, from word of mouth, from referrals by past clients. From the beginning and still, my whole focus is on serving that client, doing my best to build a relationship with whoever I’m working with, so that they feel completely seen, held, and like I’m looking out for them. And I am looking out for them.

Then I go out of my way to continue to nurture that relationship after the closing, after the transaction. And I’m also always looking to tell them the truth; for example, just in the last two weeks I have talked four different sets of buyers out of writing offers on properties. They were gung-ho to proceed with writing an offer on a property, and I made a point of telling them why they shouldn’t do it. So I think having this bigger vision for people, and a longer-term view is what makes all the difference.

If you do a great job for someone and they feel like you really got them and you listened to them and you spoke the truth to them, then they will tell everyone they know about you, the agent… And especially whenever somebody sends me a referral; whether that referral transacts or not, I immediately send a gift to the person who referred them. That might take the form of a gift certificate for food delivery service, or I’ll drop off a couple of bottles of wine, whatever it is. I acknowledge that in a physical way immediately, and that helps keep me top of mind.

Theo Hicks: Could  you give us a few examples on some of the things that you do once the transaction is over to continue to nurture that relationship?

Cynthia  Cummins: Well, I always circle back immediately to be sure that all the logistics have been handled. For example, if somebody’s moving into a condo complex, I wanna make sure that they’ve connected with the homeowners association to get all the information that they need to reserve the elevator for their move-in date, and stuff like that… So it begins right then. And then afterward I make a point of circling back every few months with a phone call. I also send out newsletters, I send a link to my blog to people if I think there’s a topic that might  interest them… And then I’ll have little client events every now and then… So just continually finding a way to touch base with people.

One form it takes is touching base with my clients not to talk about real estate necessarily. Just to connect as a human being, and then the real estate just comes along with that.

Theo Hicks: Alright. Now for the money question – you can apply this to investors, or agents, or just in general… What is your best ever advice?

Cynthia  Cummins: I actually have two answers for you. The first one goes like this – real estate is a lot like sex; you want to get lots while you’re young.

Theo Hicks: I think that’s the title of the episode there, so thank you for that. [laughter]

Cynthia  Cummins: But [unintelligible [00:15:00].01] I think it’s to always remember that it’s a home. This is for residential real estate, and residential real estate happens to be one of the best investment vehicles for the ordinary person, because there’s so much value that comes with owner occupancy… But it’s a home, not a house, primarily. First of all, it’s shelter, it’s where you live, it’s where you die… It’s the sanctuary, it’s the place where you raise your family, where you rest, it’s where you’re at home… So first and foremost, a piece of real estate that you’re gonna live in is a home, and then it’s a house. It’s important not to let the details of the transaction get in the way of making it a home.

Theo Hicks: Alrighty. Are you ready for the Best Ever Lightning Round?

Cynthia  Cummins: I am. I’m kind of excited. We’ll see how I do.

Theo Hicks: You’ve talked about lightning in the beginning of the episode, so it’s only happened we have a Best Ever Lightning Round.

Cynthia  Cummins: Okay…

Theo Hicks: But first, a quick word from our sponsor.

Break: [00:16:15].10] to [00:16:55].06]

Theo Hicks: Alright, Cynthia, what is the best ever book you’ve recently read?

Cynthia  Cummins: This has nothing to do with anything, but the best thing I’ve read recently is Lincoln and the Bardoe by George Sanders. That is a novel. I love to read for pleasure, so that was a real pleasure.

Theo Hicks: If your business were to collapse today, what would you do next?

Cynthia  Cummins: [laughs] Oh, I think I would go to move somewhere where it’s really quiet and beautiful, and I’d get a job working the counter at a diner.

Theo Hicks: Besides your first deal and your last deal, what’s the best ever deal you’ve done?

Cynthia  Cummins: Well, the first thing that popped into my mind was not necessarily the best deal, but it was the most lucrative, and that was selling a 17-million-dollar este in Atherton, CA.

Theo Hicks: The next question is what deal did you lose the most money on, but I’m gonna change it up a little bit and say “What deal you did had the greatest difference between what the property was listed for and what it actually sold for?”

Cynthia  Cummins: Ha-ha! Well, things in San Francisco tend to sell at or over their asking prices, but I had a condo for sale that I personally had developed with my then husband, and we had a buyer for it who was willing to pay — I forget what the price was. Like 1.7 million, or something like that… And there was some negotiating that went on… This buyer got a close look at the neighbor in the building, who was not the nicest person ever, and after a couple of months the buyer withdrew from the contract. So we put the place back on the market, asking 1.5, and the morning of our debut, Tuesday’s broker’s tour, was 9/11. We eventually sold the property for (I think) 1.2. But that was just some bad timing… But it’s okay, we survived.

Theo Hicks: What is the best ever way you like to give back?

Cynthia  Cummins: I like to listen and hold people in positive regard, and where I can, I like to tell them the things that are going to help them feel supported, and courageous, and happy, and I also wanna tell them, if I can, what’s getting in their way; trying to help them see that.

Theo Hicks: And then lastly, what is the best ever place to reach you?

Cynthia  Cummins: You can get in contact with me via email, cynthia [at] And then there’s my blog site, or at my retail real estate website, which is

Theo Hicks: That’s actually funny, when I read that, for some reason I thought it was single-family; I didn’t connect it to San Francisco. So thank you for sharing that for me.

Cynthia  Cummins: [laughs] Yeah, I meant to do that… I’m kidding.

Theo Hicks: Exactly, it’s got dual meanings. Alright, Cynthia, I really enjoyed this conversation. We started off deep, talking about your holistic way of thinking. You said that you identified themes around your listings in certain periods of time, and right now people are in the middle of huge transitions in their lives, and you used the metaphor of the Tarot card of the tower being struck by lightning, and the clients that you’re representing, the theme is that they’re being struck by lightning… And some of the things that you do to help with this emotional burden that they’re going through is to let them know just like strike by lightning is that it opens up a lot of possibilities. Sure, it’s gonna be uncomfortable, it’s gonna take a lot of work, and focus, but it can open up something new, and you reinforce that they are moving towards something that is going to improve their situation.  I really liked that approach.

Then we moved into talking about the differences between small and larger deals. You did mention that regardless of how low or high the prices, it’s still a home. The concerns are generally gonna be similar, but when you’re dealing with these larger deals and wealthier people, the idea of luxury changes, because it’s less about survival and more about finding meaning and quality in their home… And that there’s obviously still a concern with the nitty-gritty; you gave the example of the powder room on the first floor.

We also talked about what agents can do; agents who are just starting out, or have been doing it for a long time and want to increase the price ranges that they’re dealing in… And you said that 95% of your business comes from word of mouth referrals. Then some of the tactical things that you do is you will send someone a gift if they’ve referred you to someone, even if that doesn’t result in a deal or anything.

You said that your whole focus is on serving the client and building relationships so they feel like and actually are being looked out for. Then you talked about some of the things that you do after the transaction is closed to continue to nurture and grow that relationship, make sure all the logistics are handled… You gave the HOA example.

Circling back, the phone call – it’s not just talking about real estate, but trying to connect on a human connection basis. Sending out a newsletter, your blog, client events, and then just telling the truth; your example was you’ve recently talked four clients out of writing offers on deals, for reasons why it probably was not going to work for them… You told the truth, rather than just making something up, so you can get the deal done.

And then my favorite part of the episode, the best ever advice, which is gonna be the title, the quote of the episode: real estate is a lot like sex – you want to get lots while you’re young. Obviously, saying that the earlier you get it, the more time you’ll have to grow that portfolio and the value of the property.

And then also, to always remember that the property is a home first, and then it is a  house or an investment or something else. Ultimately, what it comes down to is it’s a shelter, it’s where you live, it’s where you raise your family, it’s where you sleep, it’s where you ultimately die.

Cynthia, again, I really appreciate you coming on the show. I really did enjoy this conversation. Make sure you check out her blog at Pick her up on her offer to send an email to ask her questions, especially if you’re an agent and want to  learn how she does what she does. That was Cynthia, at

Cynthia, again, thanks for joining us. Best Ever listeners, thank you as always for listening. Have a best ever day, and we will talk to you tomorrow.

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