So tell me about your early years and where you come from.

I was born in a small suburb in New Jersey, in Central Jersey, a town called Flemington…near Princeton. It’s about an hour and twenty minutes from New York, and an hour on the dot to Philadelphia. Nice little suburban oasis, I suppose, in New Jersey, where like you know, all of our parents worked in one of those cities and that was kind of it. It was extremely homogenous. I’ll make sure that that’s known. [laughter] And to give you a sense of to what degree, I went to a high school of about 3000. My graduating class was 760, and in that class of 760 there were ten African-Americans, male and female.

Wow.

But, I grew up in close proximity to massive cities that had tons of culture, so it never felt—I don’t know, the lifestyle wasn’t as representative as you might think from those numbers. It was pretty urban, as much as it could be from a culture and lifestyle standpoint.

That’s interesting.

It was a lot of fun.

When did you first get interested in tech?

I think elementary school. I have a great aunt and uncle that live in my hometown, and my uncle worked for AT&T. As early as I can remember. We had a computer at the house. Like most people my age, I was the reason that we got AOL in the house [chuckles]. It was always very close and accessible for me. I was super curious because I had never seen anything like that in terms of a physical computer. Elementary school had a computer class, I’m thinking first or second grade, and we’d just play Oregon Trail and things like that. From an accessibility standpoint, I think it was elementary school and that led me to programming my own role play game in the TI-86 when I was in sixth or seventh grade. There was a whole other world out there that I wanted to see, and there was access to it through the internet and that was—and still is to some degree—the allure to me.

That’s amazing. I can’t even imagine. I didn’t know tech existed until I was 20 [laughter]. Describe your experience actually getting into tech, then starting your own company.

I went to school for economics, so growing up close to New York City, at least in my town, the majority of kids are prone to either go into business or finance. Definitely during the late 80s and early 90s, things were going very very well from an economical standpoint so a lot of people were drawn to that industry. I finished college in 2008 and worked on Wall Street for less than 30 days [laughter]. I knew that it wasn’t for me. It just wasn’t what I wanted to spend the majority of my time doing. Thankfully, a sales job opened up at a startup called TheLadders.com. The job market was tough, so I said yes to the position and did B2C sales for about a year, then transitioned over into operations…and that was my first job within tech. Things started to not go so well at The Ladders a couple of years later, and I saw it coming. One of my co-workers left and moved out to San Francisco to work for SurveyMonkey. He sent me over to the job opportunities site and said, “Hey, if there’s anything you’re interested in, let me know.” There was, and before I knew it, I had put my life in three bags and I was flying across the country to live in San Francisco, a city that I had never visited before in my life [laughter]. But I was twenty-five at the time and I was like fuck it, I’ll take this risk. I was feeling complacent in New York anyway.

“I think the analogy of jumping out of an airplane and pulling your chute and hoping that it opens is completely accurate, because you’re not trained for the things that you’re going to encompass in trying to launch something.”

How did your family feel about you just up and going?

I’ve always been that way—free, self sustaining. I’m sure they thought  “This is just what Danny’s doing now.” I always make my own decisions, and I’ve always been independent in that sense, so there was nothing they could really say. I was going to go regardless.

Okay. So you got to San Francisco, you’d never been.

Yeah.

What was it like when you first got here?

Honestly, it was great. I had a really, really positive experience. The same friend that referred me for the job—I moved in with him. We lived in Pac Heights, right off of Clay and Gough, and I lived in Prospect Heights in Brooklyn in New York, so I moved from Brooklyn to essentially the Upper East Side, which was interesting. It was so new. I was in the honeymoon phase, and visually nothing that I was seeing in terms of the topography and all the parks was comparable to anything I had seen in New York or on the East Coast, so it was amazing to me when I first moved out.

How were your early years working at startups, before you became an entrepreneur?

You know, I think they were net positive in terms of…there was definitely a learning curve, a pretty significant learning curve because—

How big was SurveyMonkey when you joined?

50.

Yeah. Still pretty small.

Super small. Yeah. But as it pertains to—I don’t know, this might sound a little crazy but the tech companies that were in New York at the time, weren’t doing amazing work, in my opinion, and SurveyMonkey was great, because it was product focused. TheLadders had a large sales force. We had like 50+ sales people trying to make money for the company, and SurveyMonkey was my first time being exposed to extremely amazing senior leadership, and everyone was so bright, energetic, and passionate about what they were working on, which was an amazing experience for me in that the first bay area company that I got to work for, was this amazing company. But for me, I chose to spend a lot of time outside of work learning, so I could be competitive in the workplace. And it was amazing because they had speakers come in like Sheryl Sandberg and Eric Reese, and that’s definitely not common [laughter]. Having access to that type of tutelage from those types of folks was amazing, and being able to read things like The Lean Startup helped me learn what the business was like at a product-focused company. That was good.

What was the impetus for you deciding to go from employee to entrepreneur? It’s such a major jump.

Yeah. I think the impetus was that I had launched a t-shirt line in college. We’ll have to go back a little bit. That was my senior year of college, and during that business, myself and my cofounders recorded a mixtape to cross-promote the t-shirt launch [laughter]. We were recording this mixtape and–

I wish more people did that.

[laughter]

So my other friends, they had gone to school for music management and they knew the business—they had a record label, they had artists that they were managing, and they had recording studios. That was my first introduction to studios and studio operations, et cetera. I’ve been a lifelong musician and I loved it and—

What did you play?

I play the alto saxophone.

Nice.

Yeah, because of Bill Clinton [laughter].

Oh man.

Actually I think it was Arsenio Hall at the time.

Anyway, after we recorded this mixtape, I moved to Brooklyn, but I wanted to continue to either write songs or record a little bit and the process of finding a studio is just ridiculously difficult. And there’s just tons of friction from the artist side to the studio owners. And at the same time I used this service called ZocDoc, which is a site that allows anyone to book their next doctor’s appointment. I figured there should be something like that for musicians, but at the time I had no idea what I needed to do to build a company, let alone a tech company or something that would connect musicians with studio owners. So, that was the driving force behind my startup.

Fast forward to when I was at SurveyMonkey—so about 2 and a half years later—I had reached a kind of glass ceiling I’d say, within SurveyMonkey. I wanted to get into writing my own research, and that was not in their business model at the time. So, you were either an engineer or owned products or business intelligence or sales, and that was kind of it at the time.

What year was that ?

2013.

So I knew that I was looking for something else. Luckily I found a position at Forrester Research, which kind of offered me that. So I was able to work with clients as a consultant and write my own research. That was nice. I was there for about six months, and got poached by SalesForce to do the same exact thing, just internally. And I hope I’m not infringing on my safe harbor [laughter]. So I went to SalesForce and did exactly that, just internally. It was myself and my boss and we helped manage all of the internal and external market research, which was awesome and a dream job. But I had been quietly working on my startup that entire time. About six months, seven months into Sales Force, it got to a point where the most important input into the startup—Freshsessions—was my time. Things were increasingly—well, my time was increasingly getting marginalized because the gig at SalesForce was a very demanding position.

“You figure out how to manage it, and what to focus on. But at the time, you’re just so overwhelmed and you’re trying to like bring in so much information. And you’re reading every article on Inc, TechCrunch, or whatever. And not knowing what to spend your precious attention and energy on, was a huge challenge.”

So you were running both at the same time.

Yes. It was crazy. We had just raised a little bit of money from some friends and family and I had a little bit of an exit, so I had some money from working at SurveyMonkey. Luckily at the time I was dating a girl who was also an entrepreneur and she just kind of told me to take the plunge.  So that was the inspiration, that was the impetus and how that happened.

Walk me through what it’s like to take the plunge into entrepreneurship and the struggles involved, the amazing parts and the bad parts.

I think the analogy of jumping out of an airplane and pulling your chute and hoping that it opens is completely accurate, because you’re not trained for the things that you’re going to encompass in trying to launch something. All of a sudden you have this free time, you have no manager, [laughter] you don’t have co-workers, so you have to adjust. If you were someone that worked independently or in a field where you were making your own decisions, I think that it becomes more comfortable for those types of folks, but I didn’t work in industries or companies like that. For me I had to figure it out while I was in the air. I had to learn how assemble my own parachute. It was interesting because my other two co-founders were still in New York, so I was managing that relationship and all of a sudden my friends went from people that we would just go out and have beers with with and talk about dumb stuff to people that had to inspire and manage. We were inspired to work towards a common goal. So, what I did was spend time reading. I asked all my friends that were in MBA programs what they were learning, what books they were reading, and asked for all the materials I could get from them, and had a little staycation that didn’t end [chuckles]. I just started reading, and that’s been part of my process up until now, honestly. I’ll have to think a little bit more on some specific stories, but the challenges were, for sure, managing friends that now were co-founders, right? But also like figuring out, “Who’s building this?” We had some talent gaps. We had to find contractors to build some front-end work for us.

Seems just like a daily battle, but exhilarating.

Yeah, for sure. You figure out how to manage it, and what to focus on. But at the time, you’re just so overwhelmed and you’re trying to like bring in so much information. And you’re reading every article on Inc, TechCrunch, or whatever. And not knowing what to spend your precious attention and energy on, was a huge challenge. And that took me like two years to learn, [chuckle] honestly.

Related to learning and soaking in all that knowledge, have you had mentors or people that you’ve looked up to for inspiration along the way?

Yes. But I think the most important source of inspiration has been my other contemporaries—like other friends I have—that have launched companies and learning from them. Even if they have launched a company that was six months ahead of mine, or a year ahead of mine—they still have so much information that could help me save time—most importantly—and money, and help me navigate the landscape more thoughtfully.

I don’t have an official mentor that I check in with consistently. I did have advisors for that first company, so I would check in with them on a monthly basis. But that was it.

Where did you build your support network of other entrepreneurs?

Events. Just getting out and showing face. Undoubtedly, you bump into people that are really either interested in you, or what you’re building, or you just connect on a personal level. And those relationships are extremely important when you’re trying to do something that either has never been done before, or you’re doing something that you’ve never done before and having that support system and people that can relate and either buy into your vision, or offer some feedback is extremely important.

Yeah. Where do you think your risk appetite came from? Like, where do you think your motivation comes from? Because not everyone has that, you know?

Yeah. I think it’s twofold. I’ve been a lifelong athlete, and I think competition is just in me. But in a healthy way, like I don’t need to be competitive in all aspects of my life—

Like the game is fun.

Yeah, for sure. For me it’s fun to exercise that, because it’s been a part of me since I was five. The second piece is that, although I grew up in a nice area, my family’s not extremely well off, and things were good when I was growing up—as the oldest—and I was given a lot of opportunity. And I’ve taken that duty—I guess that opportunity, that access to opportunity as a duty to do as much as I can, take it to the zenith, and try to support my entire family—certainly my immediate family but if I can, cousins, uncles, aunts, etc. So that’s what motivates me. And I’ve been gifted in a lot of things. I’ve figured out how to navigate a lot of different landscapes, so I’ve been successful in a lot of different areas, and I think if I’m able to leverage that to help a lot of other people, then I’ll do so.

How do your friends and family feel about the work that you’ve done and where you are now, all the way on the other coast?

Yeah, yeah. So they’re certainly sad that I’m all the way in California. I see them maybe three times a year now. But, I think they’re blown away by what I’m doing, which is amazing! I think that’s definitely something I’ve been conscious of. But I don’t think they fully understand the path that I’ve chosen to walk down or folks like me that I’ve chosen to walk down. My aunt was a teacher, my mom works in a bank, my dad’s a teacher. It’s not the same. So I don’t think they fully comprehend, but I try to bring them up to speed as much as possible and stay in touch as much as possible so they can get more of a glimpse into what’s happening.

So tell me about what you’re working on now.

Yeah, so I recently launched a mobile tele-health app called Level, that provides access to psychotherapists. So through our mobile app you can have a session with one of our therapist. The inspiration came back in March or April of 2015, when I used one of our competitors and had a terrible experience—with the service as well as the therapist—that left me feeling like a number. At the time there was a lot of chaos going on in my life and I just needed to figure out how to get to some sort of baseline so I could manage it all. After having that negative experience, I walked away thinking I could build something better. I started doing some research about the industry, what kind of barriers existed, what would work with the current legislative landscape, etc. and it seemed to be a pretty smart time to start a business like ours. So I went out, assembled a team. We have a licensed therapist on our team, and an amazing CTO. Starting in August we’ve just been churning away and started seeing patients a couple weeks ago.

“I was feeling pretty depressed and definitely experiencing acute symptoms of anxiety. The first start-up wasn’t going so well and managing that along with life in general was doing damage that I could not see until it affecting my everyday life. I was trying to do too much and brute force something that wasn’t working and I should have known to fold a little earlier. But through trying to brute force a business back to life, I started to experience symptoms of different mental health disorders.”

Do you have a lot of clientele in tech?

Oh yeah.

I feel like mental health is such an issue and so stigmatized for entrepreneurs.

Yeah, you hit the nail on the head. That’s what was going on in my life in early 2015. I was feeling pretty depressed and definitely experiencing acute symptoms of anxiety. The first start-up wasn’t going so well and managing that along with life in general was doing damage that I could not see until it affecting my everyday life. I was trying to do too much and brute force something that wasn’t working and I should have known to fold a little earlier. But through trying to brute force a business back to life, I started to experience symptoms of different mental health disorders, I suppose. I believe a lot of entrepreneurs take the plunge because they have a safety net, and/or an abnormally high tolerance for risk. For me, it was the latter. I think this tolerance for risk stemmed from being able to survive—often thrive—in most circumstances life had thrown my way up to that point. Malcolm Gladwell would probably describe me as a “remote miss” in his book David and Goliath. This…survivors exhilaration, I believe, is what was driving me to continue to push the business forward, while things—around me were unraveling. And I don’t think that’s uncommon in the valley. I think there are a lot of entrepreneurs that are feeling the same way. This is certainly something entrepreneurs should be conscious of.

“I believe a lot of entrepreneurs take the plunge because they have a safety net, and/or an abnormally high tolerance for risk. For me, it was the latter. I think this tolerance for risk stemmed from being able to survive—often thrive—in most circumstances life had thrown my way up to that point.”

Yeah, I still feel this way, where we’re all pressured to have our peer-face on and be like, “Everything is great. Everybody’s great. I’m great. Look at my Instagram. Look how good my life is. Look at my lifestyle.” I think it creates a lot of people who feel lonely.

Yeah, I can see that.

It’s like everybody’s pretending.

But how do you manage that? Because you’re the face of a company. So when the face of the company is so close to what you’re actually experiencing because it’s the same person. What parts do you show, right?

Yeah. Knowing that people have so much access to you.

Yeah. I don’t know the answer.

Yeah. I think some people just either get off the grid, right? They’re not on Twitter. They’re not on Instagram.

Yeah.

Right. And they don’t do events, things along those lines. And they just kind of pop up with products.

Yeah.

But yeah. I don’t know what the answer is.

In a similar vein, what has been kind of the hardest or lowest points for you in this whole tech journey? It might be work-related, it might be personal.

Definitely it was personal.

So my ex-girlfriend that kind of like gave me this inspiration to take this plunge—it’s interesting because that part of my life was progressing pretty quickly, and the first start-up was great and going well, reasonably well…but for about the last six months of the business, it was certainly not going well. And figuring out how to be a good partner and not bring pretty stressful work circumstances into the house was hard to manage, and I didn’t manage it well, if I did at all. So that was a part of it, but I think ultimately just managing when things aren’t going well and knowing when to fold, and knowing how to manage a decline because there are things more important, like family and relationships.

“We’re all pressured to have our peer-face on and be like, ‘Everything is great. Everybody’s great. I’m great. Look at my Instagram. Look how good my life is. Look at my lifestyle.’ I think it creates a lot of people who feel lonely.”

Yeah. Well, having gone through that myself, it’s like when your work is your life and it’s your baby, and your heart, and your soul, and it’s going really hard, how do you separate yourself? I don’t know if you can.

I don’t think you can either.

How do you not bring that home because you are your start up.

Exactly. Yeah. I think you try to figure out how to communicate through it. And that’s probably the largest lesson I learned. How to clearly, objectively communicate—not communicating to prove a point, but to gain understanding and share information the right way. And, yeah that’s been valuable for me not only in my personal life, but professional as well.

Yeah. It’s so nice to have a support network of people who get you, who understand why you’re an entrepreneur because they’re similar. I’m personally very grateful for friends who understand why I would do a hundred interviews [laughter] for some random project in addition to my own work.

If you don’t, what else do we have? I’m sure you feel this way—I don’t want to speak for you, but I feel this way—if this is something that came into your head and you figured out a plan on how to do it and you think it’s a worth-while cause, do it. To not to is like…

Exactly. You just got to do it.

How do you feel about the state of tech in 2016? You’ve been in it for a little while and you’ve seen change—what are you pumped about and what are you frustrated with?

I am pumped that there is a huge push into increasing accessibility to different groups of people, I won’t even say minorities, I think it’s just people in general. Not only from the standpoint of getting access into jobs at certain companies, but learning different skills, or even having internet for the first time in their lives—when you start to think internationally. I think that is going to breed amazing opportunities, products, and services that are not only useful, but are just really really cool because so many different types of people have access to the tools to create things.  so that’s what I’m most excited about. And I’m excited that there are a lot of companies that operate on massive scales to actually make an impact—like Facebook or Google for, example. What I’m most frustrated with is—I think it’s a product of people being able to quickly create products or solve problems—but I don’t think people are working on great things. And maybe that’s some kind of bourgeois comment, but I see a lot of BS companies getting getting worked on. This is valuable time. I would much rather spend time thinking a little bit more and working on something that impacts people’s lives versus the next sophomoric Uber for X app. There actually is an Uber for puppies going around. Yes, people love puppies, but at the same time, spending a little bit more time in trying to create something that increases a lot of value or injects a lot of value into people’s lives is far more worthwhile to me.

“This is valuable time. I would much rather spend time thinking a little bit more and working on something that impacts people’s lives versus the next sophomoric Uber for X app. There actually is an Uber for puppies going around. Yes, people love puppies, but at the same time, spending a little bit more time in trying to create something that increases a lot of value or injects a lot of value into people’s lives is far more worthwhile to me.”

Are there any companies that you’re really excited about who are doing meaningful work?

I think Good Eggs is a great example. I know they just had to lay off a decent amount of folks, but increasing access to sustainable foods, and employing a lot of people in the process, is pretty cool to me.

And I think they did a good job from a branding perspective as well. The whole package is pretty cool.

What are some of the biggest lessons you’ve learned while you have worked in tech?

Ask, “why?”

And this is—I’m just really interested in getting to the root of things, and the more that you ask, “why?” , the less time there is for the opportunity there is from miscommunication and I’ve already mentioned I’m pretty big on communication now.

Secondly, act fast and ask for forgiveness not for permission.

Lastly—this is a life motto—find your passion and inspire. I believe fulfillment is inevitable with this motto in mind. That has certainly been true for me. I’ve always had a passion for helping people and I think that is what led me to launch this second company.

Yeah, I love that. I love that both of your projects are autobiographical in a way you know it’s like—

Yeah, they are.

—it’s like you’ve created something essentially for yourself, like to resolve a problem within yourself and so like you’re kind of your own primary case study. I just feel like, I wouldn’t do this project if it didn’t have something to do with me. I just feel like the really high-quality work comes from personal experience.

Absolutely I agree.

Where do you see yourself in five or ten years? Do you think you’ll still be here? You seem to love San Francisco.

I like San Francisco. No, I do. I love San Francisco but I can’t spend all of my time here. I just know what it is and I love it for what it is, but at the same time it leaves me yearning for things that it’s not—and instead of speaking in the abstract—and it leaves me yearning for diversity in my day-to-day life. Not just racially but socio-economically as well. Although I love the area and all that it can offer in a three-hour radius and all the amazing things that I can do. There are very few places in the world that you can have access to that type of stuff, those types of opportunities. I’d like to have a home here, but probably not stay here year round. So then I start to think about where else I might go and I don’t think there’s anywhere else in the US, I’ve done New York, I love New York.

Me too.

But I’m not ready to get back yet. Europe I think is probably next.

I totally understand where you’re coming from. In this project even I feel very prompted to just talk about how it’s not just a problem of recruiting. It’s a problem of keeping, in terms of diverse folks. It’s not just the pipeline problem. It’s that people come, and then they leave because it doesn’t feel quite right and I don’t know what the solution is, but I just feel like it’s worth talking about.

You’re right. I think it’s certainly changing because—I was vocal about this when I first moved here. Just having access to the lifestyle I had when I lived in New York took a long while to find. When I moved here there weren’t bars that played amazing music. A lot of the bars, if they played music, it was super corny [laughter].

New York restaurant music is astronomically better.

And people don’t dance here. Well, they do now, but not as much. Exactly, you know [laughter]! But I think people are recognizing that and there are amazing companies like Toasted Life, for example, which some of my friends own, that cater to black millennials, and they put on awesome events at venues in the Bay Area, and they play awesome music. The more that people do things like that, the more palatable living in San Francisco will be for people moving from other cities and countries.

One of my favorite things about New York—I lived there, just for a little bit. Every time I go back there, it definitely feels more culturally vibrant and diverse, but there’s more equalizers, like the subway. Everybody rides the subway. Everybody eats dollar slices of pizza late at night. Everybody gets bagels. I just feel like the lifestyles converge, of everyone, at certain points. I still use public transportation here, because I live next to a BART station, but I don’t feel like there are those unplanned collisions in the same way here.

Not at all. Where would they be, you know?

What advice would you give  to folks from similar backgrounds to yours and similar perspectives to yours who are hoping to get into tech? Or in tech now and are struggling?

I think—and I’m speaking from experience because this has helped me—I think dedicating yourself to learning helps you dedicate yourself towards growth. The only way that you achieve growth—in my opinion—consciously is through consistent effort to learn new things and step outside of your comfort zone. So I would recommend folks that are trying to get into tech to definitely try to learn as much as possible, but also step outside of their comfort zone often because again, that’s where the growth is. And this is a place where you’re consistently expected to create things that don’t exist yet, so you’re going to need to figure out how to be comfortable in that space because it’s not a comfortable space initially.

“The only way that you achieve growth—in my opinion—consciously is through consistent effort to learn new things and step outside of your comfort zone.”

So—if you’re currently in tech—I recommend to work on worthwhile problems. Don’t waste your time at a company or working on a project that  you don’t believe in. Clearly, there’s some leeway there, right? But ultimately if you can align yourself with a company that has similar values as you, then you can be confident in the majority of the work—or the net of the work—that you do is going to be positive and be in the same direction that you would already be going. I think, again, that that breeds quality, but I also think it breeds happiness because you’re working on problems you care about and it increases the likelihood you’re going to ultimately end up fulfilled…versus going to some other company and hitting the same type of keyboard, but working on something you don’t believe in, and in two or three years you’re not going to feel fulfilled about how you used your time. And your time is very, very precious.

“Work on worthwhile problems. Don’t waste your time at a company or working on a project that  you don’t believe in.”