S2 Bonus 2 Entrepreneurship with Empathy with Howard Spector, CEO

Howard Spector co-founded SimplePractice—a business management software solution and an industry-leading SaaS company in the healthtech sector that has been recognized as the Best Overall Practice Management System in 2020 by Software Pundit. As CEO, Howard has actively worked to challenge and redefine what it means to be a successful leader. By emphasizing a human-first approach and leveraging his psychology background, Howard has built a work culture that speaks to the very core of its employees and its customers. In 2020, SimplePractice was honorably recognized as one of Forbes’ Best Start-Up Employers and BuiltinLA’s Best Places to Work. Tune in to hear Dr. Pete and Dr. Rubin talk with Howard about entrepreneurship with empathy!




Pete: Well, Nikki with another wonderful guest for season two, ready for this one Nikki, what do you think?

Nikki: I'm really excited about our guest today. This is one we've been waiting to have him on.

Pete: We have been waiting and so for you today, we have Howard Spector, and he is on the path to becoming a therapist in 2012. He co- founded simple practice, which is a business management software solution that's translated into providing wonderful ease to over 100,000 providers, Nikki and I being one of them.

Nikki: Yes.

Pete: And he's gone to expand his portfolio to simple practice learning, which is also providing continued education training. So as CEO, Howard has actively worked to challenge and redefine what it means to be a successful leader. And that's a lot of what we're going to talk about today. Because he emphasizes the human first approach, and leverages his psychology background. And he's built a culture that speaks to the very core of its employees and its customers. So in 2020, simple practice was honorably recognized as Forbes, best startup employers, and built in Las Best Places to Work. So how cool is that? So an and in his spare time, which gets me very excited, enjoys meditation, tennis, hiking, and spending time with his family. So Howard, welcome to When East Meets West.

Howard: Well, thanks for having me. It was a quite an intro.

Pete: We could have gone on and on.

Nikki: Yeah, we could have gone on. I mean as Pete was just saying, for our listeners, we use some micro software, I also do courses with them like Pete and I love to simple factors and we love Howard and this episode is about entrepreneurship with empathy. And, we were just like, there's no better person to talk about this than you, Howard.

Howard: Well, that's very humbling. Thank you. Let's see how it goes.

Pete: So Howard, what about starting off in this intro, you are on your path to becoming a therapist, and then in 2012 something happened, maybe talk to us a little about that journey?

Howard: Well, I mean, it's a long story, right? But [inaudible 02:30. I mean, I'm just trying to give you the abridged version, but every time I tell the story, I feel like I need to go back to my teens because I was kind of [inaudible 02:44] things opened up for me.

Pete: Yeah.

Howard: I was trying to figure my life out in my teen; I didn't feel like I fit in. It's just like, something was off and I discovered Carl Jung actually. The story is basically I used to love the rock group, ‘the police.’

Nikki: Oh, yeah. I also love the police.

Howard: When they came out of [inaudible 03:08] with synchronicity. I actually happened there was a RA in the dorm I was living in, he was a psychologist, he had all of Jung works. And I borrowed on synchronicity, the paper that Jung wrote, and I was blown away by it. I mean, talking about a causal connecting principle and all this kind of stuff and it just really, like spoke to me. And then I bought memories, dreams, reflections, and reading that book, I had like these most incredibly vivid dreams. And I just related to what Jung was talking about, he talked about, like, the number one and the number two person and all that stuff. And it normalized a lot of things for me and it's one of those things where, when that doorway opens up and you kind of see beyond that you can't ever close, it's like you're kind of screwed in some ways.

Pete: Yeah.

Howard: You can’t close that door. Yeah, it's like ignorance is bliss.

Pete: Oh my God, totally.

Howard: So that was the kind of, something happened for me where I just found like, when I when I read the psychological kind of works I felt like I found home, something was right about it. But you know, it was a time where these weren't things people were talking about, especially men, you know, they're talking other things. So I felt like something was kind of wrong with me that I really resonated to the stuff and I felt like I had to go out in the world and be a man [inaudible 04:36] business and do all those kind of manly things [inaudible 04:40] to use like talking about man so that's how it was about that. Anyway, so I went out in the world to do my thing, struggled a lot, you know, I didn't really have a lot of direction actually suffer from a lot of depression. I went through bouts of unemployment, I just couldn't find my way but I always found comfort coming back to like, just certain books and readings and things like that. Anyway, it isn't all doom and gloom because a lot of it is, but not all of it. But basically, I ended up getting a job in the tech industry when I was like in the early 90s and I really liked it. I tried my hand and working in Hollywood and it just didn't feel right for me. I was living up in Palo Alto at the time and I just, I love the creativity; I love like what people were building and doing. And I always kind of been a little bit of a geek and I liked technology like that about like the first Apple computer for us and stuff like that. So I ended up getting a job back down in LA in a digital agency and, again, long story short, went to an IPO [inaudible 05:53].com bubble bursting. And I literally woke up one day and thought, I want to be a therapist, you know, I'm going to go to graduate school. I'm going to very specific school; I'm going to go to Pacifica Graduate Institute. And I want to go there because I was reading a lot of Joseph Campbell at the time and I was reading Robert Johnson's books, you know, he, we, she was amazing. Really getting into mythology and like, looking at myths as a metaphor for our lives and stuff like that. And I just watched the Fisher King, that movie came out [inaudible 06:28] so everything was kind of lining up. And Pacifica was a school that I had heard about from my therapist. And again, the whole Joseph Campbell connection and everything really resonated with me and I went there, and it was the most transformative experience of my life, because I was finally in a place where there were likeminded people that were speaking the same language. I felt like I finally found my people. So it really was normalizing for me in a lot of ways and really healing for me in a lot of ways. And you know, Pacific as a very experiential program to go through, you live up there for three days a month, the Sundays are your process days. So, you use your break into triads, you start going through the techniques, and it's really, you know, you kind of dread Sunday.

Nikki: Right.

Howard: The cool thing about it was, you know, I would drive up to Santa Barbara, and it was like, I was leaving everything behind to go to this magical place for three days. And then you leave there totally raw [inaudible 07:30] you come back to civilization and process all the stuff that just came up and then you go back again next month. So, it was just an amazing process for me personally. And then, in my second year, like everybody else, you have to start tracking your training hours

Pete: Right.

Howard: You go to this class and they tell you, ‘okay, here's what you got to do.’ And [inaudible 07:51] it is totally confusing and makes no sense. And I started thinking, Well, you know, isn't there like a software product where you can track your hours and try and do all that stuff and it'll generate your forums?

Pete: That was so interesting. Yeah.

Howard: Anyway, long story short, there wasn't so I ended up creating one product called track your hours.

Nikki: Which I also use when I was a grad student, right.

Howard: [inaudible 08:12] I needed it. So that'd be something where I started marketing it myself, I called up the different camps chapters, I told people about it. And anyway, more and more people started using it and it was great. But as I was going through all of my training, when I got out of school, I was working different jobs and I was doing my hours. I got all my hours, I got all my 3000 hours, I did everything but I realized that this wasn't the path for me that the track your hours was really taking off. And I also as I was getting close to being done with my hours, I started thinking about it, what am I going to do? What software am I going to use to run my practice when I'm ready to practice? And I looked at the time that was out there, and nothing really spoke to me and I thought, I'm going to create something. So that's when I had, like, going to Pacific, it was an epiphany moment for me, it's like, I just like I couldn't dance, I got to go do that and I went and did it. Track your hours was something where I was working in an entertainment marketing company, I would meditate every morning in my office on the floor and that's when the track your hours idea just hit me. And then by that afternoon, I was already developing it. And then with simple practice, I thought, there's nothing out there that I really want to use so maybe I can create something that's like intuitive and easy and blah, blah, blah. And there wasn't a little bit later where I just again, had this moment where I thought okay, now I get it, I know how I want to build this product. I like imagined a therapist, like she's sitting in a chair in her office and she's looking at her phone, and she's reviewing the notes from the previous session from the clients she was about to see. So I thought like, you know, the mobile piece of it, I started to really think about the calendar and how it was going to work. Then I just basically, I partnered up with someone that I'd worked with in another company and essentially started the company like that week. And that week of January of 2012, when we started the company, and we basically had to develop for almost a year and a half before we launched the product in July of 2013. And we got our first customer, Katie Molinsky, who's still a customer. We got the first customer in July, and then I'd like to say it's like popcorn, you got one customer [inaudible 10:28]

Pete: Of course.

Howard: Then you get a couple more, and then a few more, and it just starts to go. And we basically just were heads down in building up the product, building out the roadmap, you know, started in 2012, and we're still going. And now we're a company where we've got close to 250 employees [inaudible 10:47] almost 100,000 customers. They're serving millions of clients and patients and I'm very proud of the team we have that work for you and for our customers. We’re credibly passionate and committed to the mission that we're on; can I just talk about the mission real quick?

Nikki: Yeah, absolutely.

Pete: Please, that would be a good segue probably into the empathy.

Nikki: I think we're on the same wavelength here, yeah.

Howard: So, I really look at this simple practice. I mean, I say this a lot so for people listening that have heard this before, I apologize for the repetition. This is really a mission based company because, you know, when I was in school and when I was training, I was working with some really amazing people that were called to do this work. And a lot of people don't think of it as work, they think of it as like, wow, it's come so natural, I'm called to do this and they don't really think it's a business. There was actually someone, you know, I used to sponsor some of these, like, local campus events. And I remember this woman, I think, was the San Gabriel Valley camp, or something like that and she stood up, and she was saying how her husband thinks what she does is a hobby. And I think about that a lot because that's what she lives with, like, Look, she's doing this great work, but or her husband's not taking it seriously as [inaudible 12:13]. So for me, simple practice, the mission around this is, everyone doing this work, how do we help them really understand, like, their small business owners and entrepreneurs and I want them to embrace that part of the work that they're doing. And that, to me, is the overall mission. Because, look, you know, as a business owner, with simple practice, we have to get people in what we call the upper funnel. We have to get trial accounts in right and then once we get trial accounts in, we want to convert people that are in trial to pay customers. we don't want those customers to what we call in technology, like we don't want to cause them to churn out to leave us. So therapy, it's as for a clinician, it's the same thing.

Pete: It's absolutely yeah.

Howard: You want to get the word out there and get people to come and see, you want them [inaudible 13:05] and then you want them to leave until of course maybe their course of therapy is done and stuff like that. And the mission idea really applies to a lot of the decisions that have been made even with simple practice learning and we [inaudible 13:18] can talk about the practice website and some other things. It's not driven by money; it’s driven by this mission to do the right thing. Like the financial success of simple practice has, is a byproduct of, we have an unbelievable team of people that we treat very well that are bought into this mission that do great work. They collaborate really well with one another, they take really good care of our customers, whether it's through building the product or supporting the product, and that leads to success. And to me, that's, again, it's a byproduct. So the focus wasn't when I started this company on how do I make a product that's going to make a lot of money, that had nothing to do with it. You know, it's like, I had this idea and I tell people, I couldn't not do it. I just had to build this product, and do these things and we're very successful. I think just because, I think we have good intention, do this for the right reason. And we deeply care about our customers. And we're all here working for them.

Pete: It's like, if you build it, they will come.

Nikki: Yeah.

Howard: Yeah, feel the dreams.

Nikki: Thank you for sharing the background heart because I actually think it's really important to sort of frame this conversation that we're having today. And the reason that we really specifically wanted to have you on for this episode because in what I hear from your journey as a teenager, through your training at Pacifica, to you know, beginning simple practice is that there's this dialectic that keeps showing up that I hear of like, connecting with your values. Right connecting with what feels meaningful to you. Like, I hear that a lot when you're talking about like a Pacifica; it's like, it just it felt, right. It's like this was speaking to you, it's almost like, you correct me if this word isn't aligned, but I almost hear that, like, there's like a spiritual component to it a little bit. And Pete and I talk a lot about how like, sometimes for us, like spirituality and values are kind of one in the same, and how using your connection to those values then informs your behavioral choices. And I think that's a really powerful idea, both, obviously within business, because of course, you know, there's probably, like, a stories out there of like, businesses it's only greed, it's only bad. And it's like, well, actually, no, like there's a way to contribute to the world, and have successful also staying really connected to things that are very meaningful.

Howard: Yeah, so for me, I learned how to wear the masks [inaudible 16:06] that were required to go out and work and have different jobs doing different things, and being resourceful, but I always felt empty, and I got to life. And I think it's when I decided,  I am going to go be a therapist, that was a moment in my life where I felt like, I can't, be inauthentic, I have to be very deeply passionate and connected to the work that I'm doing. And that's how I feel now I mean, that's why I started this business. And that's why I love working with this community of our customers, because there's a lot of depth and a lot of meaning to it. And if you follow your heart and you follow your passion, and you're curious, and you seek out those things, you're going to end up where you need to be. And [inaudible 16:55] you're going to be like, oh, okay, yeah.

Nikki: yeah, it makes sense.

Howard: [inaudible 17:00] here. So, I just think that's really cool. The other thing about how we got where we are, as a company, there's so much that's written about the unicorns. and I just read today, like those two other companies like kind of trying to get in our space, it just did their series D round, and  they're raising hundreds of millions of dollars. And I just think to myself the message to young people, young entrepreneurs, is if you don't build a unicorn business, or if you don't raise a bunch of venture capital money, you're a loser. And that is the message out there. And I want to know that message and say, you know, what, I bootstrapped this company, I didn't go raise VC money, you have to do that. And you can build a business that makes a million dollars a year and that's a massive success. And I just thought, like, those things are out there enough for people to understand you don't have to be Mark Zuckerberg. That sells papers and I totally understand the psychology around that. And I want to talk more to people and encourage them to follow their passions and do the business [inaudible 18:04. Don't worry about the money.

Nikki: Yeah, worry about your values, worry about what you connect with, and use that as the guide, not as like, again, the money is like the care, and that’s the problem when people get stuck on external things. And that leads them astray, right, and it's not going to end like that you wear the mask, and it feels empty. So no, this is fantastic.

Pete: Howard, this is so great. We're looking at entrepreneurship with empathy. And I think that your training and this specific experience really brought that to you. So, one of the things that I'm passionate about is organizational psychology. And it's something that we do at Rutgers University, which is really about just the humaneness of running a business that's the definition, essentially, of organizational psychology. How do we look at the behavior? How do we motivate people to want to be a part of the mission and we had some faculty, clowder, for who took Maslow's hierarchy of needs, which everyone, all listeners that have taken a basic psych course heard of that. But he took that and said there's this ERG, existence, relatedness and growth. And so what I'm hearing is like your existence, and your suffering that we all have kind of led to this relatedness of your colleagues and now employees at the company, to really significant growth. So I wonder if you would maybe talk a little bit about that aspect of applying this organizational psychology theory to the growth of this beautiful business and product.

Howard: I mean everything has grown very organically in this company. So I mean there's two ways I'm thinking about what you're asking me. One is, well, there's the growth of the company which is the people in the company. And then there's the growth of the business, this gets the bigger and more quote unquote, successful because we have more customers generate more revenue. So do you want to focus on the company one?

Pete: But those of two are a part of it. So whichever feels more organic for you? It's a great way to tease those two out.

Howard: I mean, I think that like, as I alluded to earlier, I've had a lot of careers, I've had a lot of jobs, I've done a lot of different things. And for a long time in my life, I carried a lot of shame around that, because I had a resume that a lot of stuff on it. When someone asked for my resume, I kind of like had it broken to a cold sweat, [inaudible 20:18] like you're going to ask why I had so many jobs or why are all these times in my resume where I'm not working and stuff like that? But it wasn't till later when I really realized that, and hopefully, I'll get back to your career question we'll circle into this is that. now I love the fact that I've had all these different jobs doing all these different things, because I've met all sorts of different people, I've had to put myself in different situations to learn how to be resilient, and learn how to be resourceful, and do the things even when I was wearing the masks. But at least I had different experiences and different things. And I think that's really helped me understand and how to work with different kinds of people, or even recognize the fact that everyone is truly an individual. And that's something and that really hit home when I was at Pacifica, when I realized even the people in my class that were a little bit annoying, it's like [inaudible 21:08]. Everybody was needed, and everybody was unique, and everyone was an individual, but it really helped me understand, and I don't think this was a conscious thing; it was just an unconscious, intuitive kind of thing that played out. Like, look a company is made up of individuals and I recognize that, and I feel like because I recognize that I think people in this company feel like they're really truly seen for who they are they're not just an employee with a job description. I even tell people that when the interview here, it's like, you're not a job description, you don't work in an apartment, you're a human being that comes here with a lot of experience and a lot to offer. So let's make sure that we've got you doing the right thing. And the company is very dynamic, because, life is about change [inaudible 21:57] so it was all about transformation. And I was talking about how we're constantly in a state of change and transformation my business is, I am, my customers are, our customers are in the business of transformation so it's everywhere. For me as a business owner and I guess this ties into the empathy piece as well, it’s like the business is this dynamic system that's constantly in a state of movement. And as a business owner, I'm trying to be as attuned to that as I can to understand when we need to make shifts or changes or do things or move people around or change a process or something like that. To me, that's actually the most fun part of it because a lot of people forget kind of thing with the business like, you're in this department, you go work over here, you go do this, you go do that. But my feeling is, like the product that we produce, software is evolutionary and iterative, you're getting feedback from your customers, they're telling you what you want them to do. You’ve got to continue to evolve the product so why should a company be any different? So I feel like that's what I do as the owner of the leader of this business is understanding that we have to always be attuned to the shifts in the changes that are happening, and make sure that we're staying up to date on those things. And we're evolving the business to accommodate the individuals and the unique individuals that work here. And I feel like that's really been a big part of our success, because a lot of people come in through a kind of one door and go to one place, but they end up somewhere else. And it's really kind of cool, because we're recognizing their strengths and weaknesses and we're saying, hey, you know what? You should be over here. And one of the proudest things for me right now, for this company is really watching the evolution of have some people have really grown that have been here for four years, five years, or three months, whatever it is. Just watching them grow, and seeing how they've taken on more things or done different things, that's really cool. And I think a lot of these ties into maybe the needs that I was looking to fill when I wanted to be a therapist. Going back to your initial question about practicing, being a therapist, it's like I did all the training and everything, but I never got licensed because this was on a different path. And I'd like to joke and say that my mom still doesn't understand like why I’m not a therapist? But I feel like I'm doing better work for the community of clinicians, because I'm trying to provide for them a great resource in many different ways for them to be able to go and do the work that they're doing.

Pete: My mom still doesn't understand what I'm doing either so we can share in that.

Nikki: I think it’s interesting, like this concept of like, even though you didn't become licensed, but that's an important part of what you're doing in the business. It's also because, and I love hearing that you're saying you can come back to this concept of like being a human. Like, we're all humans that are doing this and it's a company made up of individual humans, serving humans in the community  that are providing human clients, patients to the opportunity to just change and evolve.

Pete: I love that he said that his customers are in the business of change that was beautiful, a transformation.

Howard: A butterfly is a logo. A butterfly is about soul psyche [inaudible 25:32] that wasn’t by accident.

Pete: Beautiful.  

Nikki: And there's such a, by honoring that first and foremost, like Pete and I talk about that, like, all the time on this podcast, we're constantly going coming back to life, and we're humans, this is human experience. And we discuss it, obviously, through these lenses of both, like Eastern spirituality and Western behavioral science, though; this is a concept that applies across contexts and including in business. and even what I'm hearing her talk a lot about, is practicing flexibility, right creativity, there's a mindful component to what you're describing to it's being attuned and present to what the needs are and shifting with that.

Howard: Yeah. And that plays into the culture of our company. I mean, a couple things and I’ll come back to the culture piece in a second, but going back to the mission idea, its humans, but it's really about individuals. Like you need to [inaudible 26:27] but, the mission, I think most people, probably everybody, but it's hard to say everybody, right? But people here in our company, are really connected to the human mission that we're connected to. We are in some small way helping people like you that are out there actually on the frontlines doing the work. I say healing the world, one person at a time, right? And there was one I bring this up a lot, because it's something that's like really profound, it's hard not to cry when I bring it up. And there was like that Parkland shooting, there was an image that I came across these three young kids holding a candle in this candle that visual. We have a Friday meeting with the company, every Friday, and I put that picture up there around the shooting, and I just said just a reminder our customers are dealing with people like either that are directly related to the Parkland shooting, or just people, anyone that's affected by the horrors of those things. Those are our customers are dealing with that stuff so making that connection between the work that we're doing to provide a software tool and other services to support them. That's pretty powerful stuff to know that that's what you're connected to on a daily basis, when you go to your job. We have a really incredible group of people that work at this company that are really connected to that mission, and understand the impact that our customers have on the world. Especially with all the politics that have gone on and the racial justice and all these things, it’s a pretty cool place to know that you're, again, in some small way connected to all these things that are happening.

Pete: Well, it's clearly the apple doesn't fall far from the tree by based on their leader, and I think that that's a lot of what you're, I mean, what a powerful image to put up there. And I think we could continue talking forever. We're almost out of time, believe it or not. So lastly, I wondered if you could talk a little bit about trusting your gut and meditation. So maybe a little bit about like how you've integrated meditation, because that'll be the eastern spiritual stuff that we often bring into your company.

Howard: Yeah. So someone gave me Jon Kabat Zinn's book ‘full catastrophe living’ long time ago and it literally sat on my shelf for maybe 10 years. At one point, I just felt like it just it was time for me to read it, it just called out to me and I said, okay, I'm going to read this book and if it makes sense, I'm going to do what it says to do. So as soon as I start reading it, I'm like, oh, my God. I read the book and at the time, there were only cassette tapes, like you could send away for John's cassette tape. So I did and I basically tried as best as I could put myself through the course in the body scan the whole thing and it was totally transformative for me in my life. I never felt more grounded. I never spoke more clearly. I said what I meant, I meant what I said it was like a tennis game was amazing, because [crosstalk 29:44] it was unbelievable how transformative that was. So I ended up actually, I went did some trainings, and I opened up a wellness center and taught the six week MBSR form  because I felt like facilitated and I teach it, I help people do that work, because I just felt it was so powerful. So for me, and I've been on silent meditation retreats at spirit rock and other places.

Pete: I love the silent retreats. Actually, we talked a lot about that in this podcast, because that's what I missed the most of the pandemic, there's silver lining somewhere, but that's the Silent Retreat option, I'm just missing to like, recharge. Because you know session in the Zen world, like you need that longer period of sitting, you can sit every morning and night but that longer period for that discipline…

Howard: You got to give yourself like, a few days to just…drop in, and then it's just like, you know.

Pete: That’s the best.

Howard: that’s amazing.

Pete: Maybe one day, we could do that together.

Howard: Yeah, let’s do it. I think that training for me and doing that work, and practicing meditation, it grounds you in the present so I have a very present kind of outlook on life. When people say, hey, I'll see you tomorrow. I'm like, well, how do you know?

Pete: Exactly, yeah.

Nikki: No, we talk about it all the time, it's very literal.

Howard: If we have a great month of simple practice, I don't assume next month will be that way, it's like next month so I don't take time for granted. Your time is our most precious resource. That sounds cliché, but I really believe it. I don't want to waste my time. I don't want to waste other people's time, I want to make sure that the things that we're doing we're not wasting time. So having that level of attention, I pay attention to things. So when we talk about our company culture and things like that, these are just words that just get spit out there and not followed up on. I'm very mindful of making sure that the things that we talk about at our company that we want to do and then the things we want to embody culturally and ethically. We have to vigilantly guard those on a moment by moment basis as our employees are the people that work here, they kind of say this thing, but they don't really mean it. And things like that, and it totally disintegrates the trust and the bond, the people that are working and the people that are leading. So I'm very mindful of those things as best I can. I'm not perfect, but you know, that's where that comes into play where if you want to have a great culture, you got to define what it is and you got to be hyper vigilant about it moment by moment and guard it because it's a slippery slope. Once you let things go, you're done. And I don't want to be done.

Pete: This has been When East Meets West. I'm Dr. Pete Economou.

Nikki: And I'm Dr. Nikki Rubin. Be present. Be brave.

Pete: This has been When East Meets West all material is based on opinion and educational training of Doctors Pete Economou, and Nikki Rubin.

Nikki: Content is for informational and educational purposes only.