Ep 26: Brian Schecter (SelfMade)


Ep 26: Brian Schecter (SelfMade)

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So Brian thank you so much for coming on the show today.

Brian Schechter:

Thanks for being here I am excited to chat.


So when you are at an event how do you introduce yourself to people?

Brian Schechter:

Hello my name is Brian Schechter, I am the co-founder and CEO of Self Made, Self Made is a New York start-up, venture backed and we are helping people build their brand on social media.


Nice and concise, I will get onto Self Made shortly before we delve into Self Made., talk to me about your early career; are you from New York originally?

Brian Schechter:

No I grew up outside of Boston, after college I spent a year living in India and moved back to Boston where I began a career as a teacher. I got a Masters in Education then moved to Washington DC where I continued teaching. The first part of my career was really focused on education prior to then diving into start-ups.


I guess… fist of all what was you teaching?

Brian Schechter:

I taught ethics and civics in Washington DC to juniors and seniors. I loved it… I loved the subject matter, I loved the relationships with the students, it was extremely engaging work and I don’t ever miss it, as it was also gruelling, it wasn’t having the scale or impact that I was really looking to have.


So interesting, I think you might be the first teacher that I have spoken to… not in my life but as an entrepreneur. I speak to a lot of founders all of the time and they usually come from a consulting group or this place that place or investment banking none of them were teachers before.

Brian Schechter:

I think that teaching is actually an incredible teaching ground for entrepreneurship, especially for being a founder because as a classroom teacher you have an opportunity to lead a group to accomplish things and that group doesn’t know how to do things when they first start. It requires a lot of flexibility, a lot of give and take, what you really want to go after as a teacher is something that at the beginning seems impossible to accomplish but as you start to make progress you start to see how you can actually get there.

There is a lot of Project Management and logistics, there is a lot of persuasion, there is actually a lot of strategy and curriculum design. So there is a bunch of things that I am super grateful for as a time when I was a teacher and what I do now as an entrepreneur 


You really just sold becoming a teacher, you should delve back in and become a campaigner for the Teaching Association.

Brian Schechter:

It was campaigning that was the bridge between education and entrepreneurship.


Yes I remember you saying so you were actually a part of the Obama campaign?

Brian Schechter:

2008 Fieldburg and I was in Missouri for the Obama campaign.


Wow and what was that like?

Brian Schechter:

It was an incredible experience I loved it. It was the thing that made me realize that I should go and build businesses because when I started working as adults on the campaign where we were going after specific numbers it was just a whole new side of my professional life just exploded and I was absolutely on fire with it and I wanted to continue doing that after the campaign but I didn’t have any interest in going into politics but I wanted to build things and I wanted to compete and build businesses the best that I could.


What was some of the things that you saw or encountered that set off that fire within you?

Brian Schechter:

Part of it was just the realizing how much of a difference leadership can make in the context of a group of people, there would be … there were ten extras on the campaign where they would … the output was very obvious similar to in business in terms of revenue and growth, you could just see how many phone calls were getting made, how many doors someone was knocking on and you could just see the results very clearly and there was a group of us who were able to do just literally 10X what other people were able to do, I was in that group and I wanted to continue doing something professional where I was exercising the skills to have that type of impact.

Running a campaign is like… running even a part of a campaign is a lot like running a business too.


So this then leads you into your first venture, which is ‘How About We’.

Brian Schechter:

Yes so a huge part of that was also about doing it with my best friend from childhood who also had become a teacher, we actually both worked in India for a while. Eh and I really decided together to start a business and then began the process of learning literally from zero, how to get a start-up off the ground. The idea that arrived was ‘How About We’, which is a dating site where couple could say the phrase ‘How about We’ to introduce the date idea.

So ‘How About We’ get drinks at this roof top bar that I know, which is a sentence that I said probably [Inaudible 05:58] in and around 2010- 2011. We were truly green both when it came to business, technology, innovation and we created something that … it was exciting, we built a strong brand but we did not create something that truly disrupted the dating category and I got to watch in that time period of “How About We’, Ok Cupid, moved form being something that was fringe to something that everyone knew about and there true innovation was around free and then I saw Tinder happen really from the inside of the dating industry and there was iteration was not on free but mobile. It was really the first IOS friendly App to hit the dating market and it just crushed it.

There were lots of other specifics there but the big thing that Ann and I didn’t understand when we first started was the nature of differentiation that we really needed in order to create value especially in the context of a saturated market such as online dating.


That is good and so where did the idea come from, so you both leave the campaign, you want to start a business, why dating?

Brian Schechter:

We were both single and 30 years old, we didn’t really understand how to think from the standpoint of what is happening in terms of technology in terms of business, we were thinking in terms of human problems which I think in many ways is good but you have to have both lenses in order to really come up with something that is going to be as explosive as you really need to be if you are taking the route of venture capital and going after a large exit.


Because you guys raised about $22 million, which is insane, so how did you start? You have gone to the drawing board… I don’t know anything about start-ups, I was teaching ethics, what did he teach?

Brian Schechter:

We were both … we taught… I think it was called The Communities, or something like that.



So you both don’t come from a business background?

Brian Schechter:



So have gone on Setup.com and gone on all the blog and their websites, so how did you start?

Brian Schechter:

We worked our asses off, we were just grinding and it was a combination of networking and being good at always asking people who else should we be talking to? Always finding out if there was any way that we can add value and always being genuine and that took us a long way and we always… we had a motto I think even in the very beginning it was something like ‘Always do the thing that we needed to do next’ I think it was within 3 weeks from deciding that we were going to do ‘How About We’ that we were showing mock ups of the website that we were going to design, we designed ourselves on Wicks to people in bars. Saying “Would you ever use something like this?”, “What sites are you currently on?” we knew that we needed to have an experimental and learning approach, I don’t even know how else we could have gone about doing it.

It was just hard work, networking and doing the thing that we needed to do next and if I could do it over I would actually put more emphasis on study, some of the things that I have come to realize I could have come to understand through a it more in depth analysis, like reading up on what are the true classics around books or thinkers or really outline what is the process of creating a start-up, Four Steps and an Epiphany was a book that I read years after and I was like oh man I wish I read this before.

The book was Four Steps and an Epiphany; I think ti was called…[Interrupted]


No, No I have read it.

Brian Schechter:

That book outlines what re the types of innovation that are required to really build massive value and one of them is a new …something truly new.


Ep 29 Derek Flanzraich (Greatist)

Ep 29 Derek Flanzraich (Greatist)

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PHILIP: Okay, Derek, thank you so much for coming on the show.

DEREK: I’m glad to finally do it. 

PHILIP: I’m glad to finally be back.

DEREK: I’m glad that you agreed to let me on.

PHILIP: Yes, I’ve been waiting for this for a while. This is definitely overdue.

When you’re out and about, how do you introduce yourself?

DEREK: Interesting

PHILIP: Depends on the crowd?

DEREK: Sometimes I’ll say “My name is Phil.” but no, you mean like professionally?


DEREK: I always say I’m CEO and Founder of Greatist.

PHILIP: You don’t even tell them your name? You just go…

DEREK: Yes. I try to emphasize mostly that I’m purely my profession and I have no personal characteristics.

PHILIP: So you were born in the west coast and then you moved to the east coast. What was early life like?

DEREK: Yes, I was born in California. My parents moved me to Miami, and then I ended up going back and forth on the coasts. Anyway, now I’ve been here in New York for 6-7 years. 

I grew up struggling with my weight, so that’s a big part of sort of my story is that when I was 8-9 years old cut my hand and ended up with my right arm in a cast for 4 years. And then right at the tail end of that, right as I was sort of drinking the most soda and feeling the most sort of out of sorts , and feeling very alone and reading lots of books, my parents decided to add insult to injury and moved me to Miami, Florida. 

I’m not sure how much they thought about it, but it felt to me at least like that was sort of wakeup call a little bit when I was around sexy people. I’m like “I need to get my shit in order.” I just couldn’t quite get around this notion of why should I get my shit in order to be sexy to please others, like, what do I really need? And it wasn’t until that it was like “Oh, at least it’ll make me feel good.” that sort of started working, started on my journey to try and get more healthy and more fit. 

Yes, I started to turn on these TV shows, and read these magazines, and buy these products, and try these programs, and felt like every one of them made me feel worse about myself instead of better, and wasn’t on my side, and felt so at odds with the way the world should be and what I need. So I started reading all these scientific studies to kind of go straight to the source, sort of bothered all my friends about it. 

The most shocking part of all of this was that they listened to me. They paid attention. That probably laid the foundation for what I do today more than anything else is this feeling like, wow, I am not an expert. I don’t quite know what I’m talking about, but somehow I’m resonating with my friends, resonating with this sort of generation, millennials as a group, because I am talking about it in a more real authentic sort of friend who’s a little further a long way. 

And if you take a look at what we do today at Greatist, today, all the contents voices that. Now it’s lots better than I was back then.

PHILIP: Yes, of course. We’re going to go on to Greatist origination shortly, but… 

DEREK: I’m sorry…

PHILIP: that’s fine.

Obviously, I’ve worked with you for a while. I had the pleasure of shadowing you. And something that I noticed while I was working with you was that entrepreneurship seemed quite natural. Where do this come from up until the point of starting Greatist?

DEREK: Oh you want to talk about childhood. 

I think I’ve started my whole life. You know I have strong opinions about this. I basically think some people are born to start things, and I think some people pretend like starting things is cool. They’re terribly misled. 

There are times, frankly, in which I would love to not be someone who is a shit employee and who has to start his own thing all the time. But whether it’s a blessing or a curse, from a very early age, I was starting things. 

There’s literally a framed picture of a sort of advertisement I had written in my home in Florida right now where when I was a little kid, I had started a dog-walking business. It was called The Flanzraich Brothers because me and my 3 years younger brother were involved in this. The idea was that we would walk your dog, but I was so small that I couldn’t even hold the dogs. I’m not really sure what I was thinking, but I’m relatively sure that people signed up because I was really cute, and my mom did all the walking. 

But my mom really encouraged me to always do stuff. My dad is very entrepreneurial. He didn’t have the same resources and opportunities that he gifted me, and so the other part of this is the sense of everything that I’ve done—maybe besides the dog-walking business—everything that I’ve started or tried to start has always had a part of it that was about making social impact, and about sort of giving back, and bringing something to the community that was important because I think that’s really important.

In middle school, and high school, and college I started these organizations, and those organizations, many of them are still around, and all of them added something that was missing, and that I could be really passionate about because it was helping others.

PHILIP: That’s amazing. 

So going on to Greatist, obviously, you explained that you had this struggle growing up with your weight, that kind of led you to Greatist by accident or did you always know you were going to set up another media company? Because all the other ventures that you had, like at Harvard and at middle school were in the media space or something.

DEREK: Yes, they were. I think media—alright, so the two questions here, the first one is like media, in general, I’ve always just been enchanted with this notion that you could reach people on a big scale. 

And so in middle school—I can’t believe I’m middle school—but in middle school, I created this online political forum, literally like a chat room and a blog, and we published a monthly newsletter. And then in college, I did this online TV show. So, every time you’re sort of adapting to what the new platforms are trying to get a larger message out and to build a brand because I think brands are—if I reflect back on what I’ve done and what I think I am at least not terrible at, it’s sort of building a brand and the importance of having a brand. 

It wasn’t until I graduated from college that I realized that building a brand and building a business around the thing that you’re most passionate about personally is an unfair advantage. I actually basically assumed that health and wellness, those are my passion and my struggles with health wellness were personal, and that’s a thing I do on the side during my lunch time. Sometimes I actually hide from my friends that I’m doing this on the side. 

It wasn’t until my first job out of college __[07:39] technically my only job, I guess now, besides this one that I realized how important that vision, sort of a contagious heartfelt vision can be and what an unfair advantage, again, it can be to hire people, convince people to rally around your cause and to keep you going at when things are really tough. 

And so, I really took to heart this notion 6 months into this startup I joined out of college that if I were to start my own thing—which by then I was thinking absolutely I wouldn’t, maybe even on a more accelerated timetable __[08:16] planned—that it would have to be in that area that I was the most passionate about. I knew what that was already, but I just hadn’t kind of put it together that that could be my job. 

PHILIP: And then how did you start Greatist? What was the first thing that you’d done?

DEREK: What was the first thing that I did? 

So I joined this company, and it was well-funded SoMa-based company, high-flying and it did spectacularly well, and I had nothing to do with it, but I was totally 


I felt then that the minute I came, I basically was like “Man, I think I know better.” and that is a very dangerous notion. I’ve had a hubris pretty well 5 or 6 years, but I still have no lack of confidence. I, unfortunately, often do think I know better. Again, I’m trying to some of this unfair and I’m often wrong. That sort of part was propelling me to start my own thing, but because I hadn’t clicked with me that I need to just go after health and wellness, I kept thinking like “What is a good idea? What’s the thing?” 

And so, I spent a lot of time coming up with various business ventures, to think a lot of people did. I spent a lot of time feeling the market; talking to people about them, sort of sketching the ideas, talking to experts who knew something about the space, and nothing really felt right until I came back to sort of health and wellness. And think you know about this, but my original plan is to buy a gym. 

A friend of mine owned a gym in SoMa, San Francisco and he needed help. He was a really good gym runner, but bad at all these other things, you know. He was like “Well, come be my partner.” I thought about it. And in that thinking process, I thought I don’t really know what people need. It brought me back to the experience going through Weight Watchers growing up. It brought me back to the experience of the media things I had done before and how you can build an audience over time and then learn from them. And sort of my response back to him was “Can I build a big sort of media company around this notion, so that we can eventually figure out how to scale a big multibillion dollar business?” And this guy sort of was like “I really just want to build a gym.” And then I thought, well, that’s the least appealing part to me. I want to do all this other stuff with rest. 

And so I decided to do all this other stuff, and it dawned on me that I could bring these two passions: my personal passion and sort of my business ambitions together. It sort of reinforces notion that I didn’t just want to build a business, but I wanted to build THE business. You’ve known me. No ambition because I want to build fitness theme parks one day. So getting to build fitness theme parks, you don’t just build one. 


DEREK: And then the other thing was it also sort of humbled me in the sense that I did not know really what the billion-dollar business in this space. I didn’t really know what that product and service would be. But because I’m a white dude who went to a good school and grew up on the coasts—and even though I feel like I’ve struggled in the sense that I’ve dealt with body image issues, and continue to struggle with my weight today, I kind of know what that struggle is like—it’s very different from being the target audience of almost every single health and wellness product. I, frankly, never wanted to build health and wellness solutions for people that already figured it out. 

And so that was when I said that what I need to do is build an audience for those people. I need to learn from them and then I’d figure out what the right product and solution is. 

And so I started media company because in many ways it was to learn. And because I thought I was a huge nerd reading everything online, I thought there was a big opportunity, big hole and a void of a brand that spoke to people like a friend further along. That way, I spoke to my friends and the voice that I felt was missing in the space. 

PHILIP: And then you were the first writer?

DEREK: Yes. I mean, I can’t remember if technically I was the first writer. I knew from the beginning that I didn’t—even today, people call it a blog. For some reason, a blog always like I imagined is like some dude in his pajamas…

PHILIP: Making $100k a month

DEREK: But I, from the very beginning thought, again, very ambitious about where this was all going to go. And so from the beginning, I had multiple people who I sort of brought on, people I’ve worked with in college or people that I had begged my friends to introduce me to to basically be sort of help. And so they were editors and writers, and I was definitely the main editor and I wrote a lot of the early stuff as well. And we spent 2 or 3 months actually writing content before we even went live because a big part of my theory was you wanted to come to a site that already had—I wanted you to come to Greatist and say “Where has this been? How have I missed this?”

PHILIP: And how were you like funding at the beginning? Will they these people or you guys like—how scrappy was it?

DEREK: Totally. Nobody was paid anything. I was working on a 24-hour Starbucks at San Francisco with my 4 roommates in the Inner Richmond in San Francisco. It was about as scrappy as it gets.

PHILIP: And then what was like the turning point for you when you were like ‘Okay, this is actually going to be a real thing’? We need to raise some money. We need to get more people. People actually come to the site. What was that day if you can remember?

DEREK: My first answer to your question is I always believe that. 

PHILIP: You have to

DEREK: Yes. And I have never doubted it since. 

But the moment in which I first saw—man, it’s not just me who thinks this—is when we launched in April of 2011 and people liked it. There was not 100-200 people on the site, 5,000. I just remember the feeling like my sort of creative growth hacking strategies, and my vision about what a brand could be, and what was missing in the space that I was not wrong about some of that, and that felt really validating, and it felt exciting. 

It’s what actually prompted me to move across the country and move for the summer of 2011 into an Airbnb, which believe it or not, Airbnb has existed 6-7 years ago, and move in that summer with a couple people who had been helping me who were just about to graduate from college. So I sort of sold them on this notion of “Hey, you two are my trusted hands. Let’s spend a crazy summer in New York. You guys are on the east coast. I’ll just meet you there. I can’t afford to pay you, but we’ll get an apartment. And so we all moved in, one of them I’ve never met before and we had a crazy summer.

PHILIP: I’m sure.

DEREK: There were ups-and-downs. By the end of summer, I think we all knew that there was something that. There was something to this and we kind of found our kickstart sort of the fuel. Sort of the place where it all started was on Pinterest for us. When we launched, it was sort of like “Oh, this is a thing?” and then Pinterest was when we said, “We’ve got that up into the right curve.” So we found Pinterest. There’s a lot of stories around that, but basically, we found Pinterest, that took off and we took off along with it, and that’s when I actually convinced some people to try and give me money so I can keep this going. 

PHILIP: When you were like trying to get Greatist off the ground, were you tinkering with other platforms or was Pinterest the first thing that went and you’re like “Holy crap! This is actually a thing.”?

DEREK: Oh, definitely not. We were tinkering with everything. 

The moment where we found Pinterest was because we all sat around and acknowledged the fact that we had no strategy and that this notion of just create great content is I think the number one strategy, but it’s not enough on its own. If you build it, they won’t come, basically. So the question was ‘Where are they?’ and ‘Who are they?’ And so we sort of decided that we would start narrowing down who our audience was. And the audience we decided on were basically millennials trying to get healthier, and then we asked where that audience is, and looked around the table, and we were all on Pinterest – this new cool thing – and no real brands and businesses like ours were there. So we sort of decided that was our ticket, and look, spent months and months trying to figure it out and kind of being on the cutting edge of what was needed on that platform, figuring out a couple things that worked that I actually think we were really innovative actually on Pinterest, and that paid off when Pinterest took off. 

PHILIP: One thing I’ve always found very fascinating about Greatist is the fact that you guys, you don’t play the media game the same way everyone else does. But you guys get awesome peak. 

Last night, literally last night I saw an LED sign on the taxi for. You guys just don’t do stuff like that. You spend 0 marketing dollars. How have you been able to still stay relevant with such a huge audience whilst not spending any money?

DEREK: I just don’t like playing games. I think it’s all about what you’re trying to build. So if you take a like a big step back or then you say “What is this all for?” I told you I didn’t even attempt to really build only a media business. I intended to use media as a springboard, actually, for this like “THE brand of the future”. If that’s your goal, then you can’t mess with the audience. You can’t play games, and you can’t juice page views and skew the numbers just for one quarter or just for one month because it’s fake. It’s only the real stuff that matters long term. If you’re really building a long-lasting brand, it’s a lot, actually about being willing to take short-term compromises for long-term gain.

PHILIP: And what does that look like?

DEREK: Well, I mean, the obvious example is not creating lots of clickbait-y bullshit content, you know. We want content to do really well on the internet. We package and frame our content in a way that we think is really shareable, but we don’t do sensationalize clickbait-y titles. We are scared to overpromise in the title something of an article because the one time you click in expecting one thing and get another is the time in which your user no longer trusts and cares about us and believes we’re on their side. 

And so, again, that is maybe not the best way to build a 100-million unique visitor a month $50 million advertising pageview business, but that’s not what I want to build, right?

And so I don’t think that’s the wrong approach for some people, but for me, we don’t play those games. And if we can’t build it organically, we try to find another arena in which we can win the right way. And I actually think most of these platforms increasingly move towards celebrating, encouraging and promoting the better stuff. 

And so there, I think it’s about just time. If your job is to kind of get huge on Facebook and sell, I’m not  that. That is a hard, tricky game to play, but some people play it beautiful. 

DEREK: Yes, so that would be a great example. I mean, there are 3 or 4 other examples of people who’ve tried and tried to do exactly what they did and don’t exist anymore. It’s a dangerous game to play. 

I tend to think of all this in a longer-term sense which is if we’re going to change the way people think about health, how do we build a business that will be sustainable, that will build on itself over time, and that doesn’t need to maximize one tiny window to succeed or fail. 

PHILIP: And I think a lot of companies now are trying to produce good value content. Because you guys are so intentional in building an organic audience, what are some of the things, if you can share some tips or tricks that you have done in order to be sustainable and like rank number one on Google every single time?

DEREK: Yes, I mean, the biggest trick to ranking number one in Google is write great content in a space that there’s very little of it and they get a lot of people to share it because it’s that good. The crazy hack. But I will be the first to admit that our “SEO strategy” was exactly what Google told people to do which was write great content. I mean, nobody wanted to do it. Nobody wants to do the hard work. 

I’ve been working my ass off for 6 years and there’s nothing more I would love to do than work my ass off for another 50 years because I think hard work, and attention, and care to the details, I think doing it right long term pays off. It’s maybe not as sexy, but it’s just like health,  trying to put this together, maybe you can help me.

It’s kind of like health. Losing a ton of weight in a short period of time rarely sticks, right? What you need to do is adopt healthy habits that you enjoy that you keep doing over a long period of time and then your life is long and happy instead of full of guilt and shame over something you didn’t accomplish or the yoyo effect of always looking for what’s next.

I think similarly about building a business, actually – that our job is to continue to get better and better and better, and it’s okay if we mess up sometimes, not mess up so bad that you have to start from scratch—I don’t know. I haven’t fully figured that out. 

But there’s something there about how we are trying to build a healthy long-term business that lasts. I think lasting, doing it right in a market that’s really lucrative and with very ambitious agenda is the best way to build a multibillion dollar business, and I still believe very much we’re going to. It’s what they talk about when they say you’re an overnight success. It takes 7 to 10 years. We’re on our way.

PHILIP: Yes, exactly. Absolutely. 

So I want to switch gears a little bit now and talk a little bit more about culture. 

You guys are notorious for your amazing culture here. You’ve won many awards over many years, and you’ve created this culture that is like unparalleled to anything. Obviously, a lot of thought has gone into this.

DEREK: So nice for you to say

PHILIP: No, no, no, I mean it. Obviously, a lot of thought has gone into this and it’s created this work environment which is really authentic and genuine. How did you create that and why was it so important to you to create such a good culture here?

DEREK: Yes, it’s so nice. It’s nice coming from someone who’s actually been here.

I don’t think it’s that hard to create a great culture, actually. I think people talk about culture a lot because they don’t want to do it. They just want to talk about it. 

I got to start from scratch, so in that sense it’s easier because a lot of people are trying to fix things that are already wrong whereas I got to and very simply create the culture. I wanted most to do my best work. And so, my job is to create a culture that enables everyone to do their best work however they work best. I had some ideas about what that would be for me, and since then I’ve incorporated lots of other people that are not just like me who feel strongly about what they need. 

And so, a lot of companies offer the same benefits we do: flexible hours, and no vacation policy…

PHILIP: Snacks, everyone 

DEREK: Snacks, and fun events, and drinking or whatever, fitness activities, iced coffee. I think none of that shit matters at all. It’s all about ‘Why?’ What is that they’re for? And also, how you hire people that will not abuse that but actually use that as fuel to be the best professionals they could be.

I would say, first, the most important part about building a great culture is to have a leader who cares about it at all. I do a lot. You’ve seen how much I care about it. And the second thing is hire people who are going to thrive at it because, I mean, that second part is really key. And fire people when they even if they’re talented, even if they’re good people. I think you also have to allow it and embrace they’re changing over time which it definitely has. Just even since you were here, it’s changed.  

PHILIP: You’re even sitting somewhere else, yes, it’s crazy. 

DEREK: I’m sitting in another seat, I know. Wow!

That’s really crucial to me. 

I think it actually goes back to building a business right. I’d like to think we’re an example of a business that has succeeded far and above its resources and its amount of people, and far and above the amount of time that it’s been around, in part, because we’ve empowered people to do the best work while they’re here however that is.  

PHILIP: So when is the right time for a startup to start thinking about culture? Is it you’re pulling on 5, 10, 1? Like, when do you start incorporating this culture?

DEREK: Core values before the business start. Whenever someone says “We’re starting to work on our core values.” it sounds like it’s an insane thing to me. How can you work on your core values after existing? It’s your core. If you haven’t created them—sometimes I scare people and I tell them “If you think you’re creating core values now, you just don’t know what your core values’ already become.” or you don’t want to admit that. 

I think you do have to be very intentional.

PHILIP: Now, like most on the top, you’ve fallen hard times. Early last year, Greatist had to make some pretty tough decisions and let a good portion of the company go. Now, this happens to startups all the time around the world:  issues, happen. 

How did that, I guess, affect the team and how did that affect you?

DEREK: Yes. So, we did have to make a hard call at the beginning of this year, and yes, it happens at all these companies. Of course. Of course it happens at startups all the time. But no founder—at least not me—ever thought that it’s something that would happen here. I always thought “Sure, that happens to other people, but I won’t do that.” And then of course it is. 

I made bad decisions. We put our faith in like the wrong industry at the wrong time. We hired poorly. I made calls that knowing what I know now, if I had known that then, I would have done them differently. 

But it ended up being that we had to let go of a meaningful portion of our team. It sucked. Just honestly, like for me, it was terribly painful, and I was the one being let go. That part is killer. 

It’s just like I remembered sitting there and being like, okay, we have no way out. The last thing we want to do is—there’s nothing worse than running this into the ground so that have a chance to succeed. That’s the ultimate disservice to the people that work here and have worked here. 

So then we have to make the best of a real shit situation. And how do we do that? And look, we did a lot wrong, frankly. It was my first time letting meaningful people go and we tried the best we could, and I think we did okay, but it sucked so bad and we probably only started recovering, I want to say, 6 months after that. I think it took that amount of time for us to kind of poke our head out and say “Okay, we’re starting to get back to growth.” That’s the plan. The plan was always—we grew too fast. Our revenue didn’t pace our expenses. We realized that later than I would have liked, but in time for us to turn it around, and this business still has a lot of potential and opportunity, and we need to rebuild. That’s what we’ve been doing.

I think we’re very much on track now. But emotionally, it was a real toll for everyone here. People who left, of course, but also the people who stayed. As a founder, it feels like a terrible failure. In some ways it is, but in other ways, this is the way all things are. I’m a first-time founder. I’ve been doing this for 6 years, and I’ve learned so much in this experience. 

I’m such a better leader than I was when I first started out. I think maybe there are some people who are just amazing at this, and perfect, and flawless, just like maybe there are some people who in health never struggle remotely with anything. But I find I need to make mistakes for myself before I really learn them. It is so sad that it has affected other people in the process. So my hope is that this learning would prevent that from happening again, but you know, it could happen. 

Maybe many more people in the future—I hope not—but it’s always possible and—so it was a real learning experience, and it really sucked, and I don’t wish that on anyone. I think it’s making us, as a business, stronger and smarter. We have profitable. We are effectively a business that now is not only paying for itself but headed in a direction where it’ll be profitable from what we’ve built already, and that is exciting. I’m only sorry that it had to take some of these hard decisions to get there. 

PHILIP: I had left before that time, but I kind of saw the run up to that: board meetings, and this and that and the other. I know you guys did everything that you could to avoid that situation. So I guess like post that happening, what did you learn most about yourself coming out of that situation?

DEREK: It’s a good question.

I mean, you were there so you saw a lot, and I appreciate you talking about how hard we’re working to prevent the situation.

PHILIP: Yes, I know.

DEREK: Because we really were and very few people would know that for somebody who just works here day to day where, I think we’re relatively transparent company. People heard from us every month. Multiple people that were let go said it wasn’t a surprise. You were telling us everything. But for a lot of other people, they were really caught by surprise. They’ve only been here for a little bit or, frankly, they just didn’t think it was going to happen. 

I think the thing that I learned about myself, definitely financially I learned the importance of having great advisors. It’s something that I’ve struggled with finding, and it’s something that I personally had especially early on at Greatist—we didn’t make a lot of revenue early on. That was kind of the point. The point was build trust, build an audience, and fund the company through the investors. And then we started to sort of make a little bit of money, but the minute we started making a little bit of money, we raised more money and then started spending it. And so it was a real sort of forced lesson in financial responsibility, honestly. 

It helped me recognize some of my weaknesses that I need to find other people to complement me on. Recognizing that is not always that great because that means you actually have to find someone who will help you. As you know, we’ve been trying to find people to fill in certain gaps here that for timing reasons, or budget reasons, we couldn’t afford to bring in. But I am not everything. It used to be, at one point, at Greatist I have to do almost everything mediocrely. Now not only can I not do everything mediocrely, I can do most things, and a few things that I focus on I’m supposed to be amazing at but everything else I need help with. And this really helped me organize some of those things that I was kidding myself about being good at. And so, I hope that I have learned that lesson, and I think I have. 

PHILIP: That’s good. 

I want to work towards wrapping up now. So you’re a health and wellness company, how can you stay healthy whilst running a business? Because it’s not easy, right? What are some of the things that you do?

DEREK: Well, a lot. And I’m going to define healthy very broadly. 

But people who know me know I’ve got like my routine and I’m very obsessive about my routine. 

PHILIP: I know.

DEREK: But today, I wake up every morning at 5:30. I work out in the gym 3 times a week or I work basically in the morning. I have like my standard breakfast that I eat every morning.

PHILIP: Which consists of?

DEREK: It’s now 2 to 3 eggs and steel-cut oats. 


DEREK: Always with cinnamon and sometimes with some almonds


DEREK: Fresh blueberries, but they always go bad in the.

But for me, the gym, that’s stress relief. If I don’t go, I feel it. It’s not really for any other part of my health. And actually, I worry sometimes that I’m in the gym like working too hard at the gym, but I do it because some of that just sweating it out is very crucial to me. And then I’ve realized—I don’t think this is true for everyone but for me at least—that I’m extraordinarily in the morning. 

I basically, when I come into the office at like 9:00 – 10:00 am full days’ worth of work and then I’m just in meetings, and I’ve started ordering from the same place lunch every day. Like, my dream is basically to be Barack Obama in terms of just like picking which color of suit I get to wear and then just go with it, or even somebody else choose it for me. 

PHILIP: I’d like that probably

DEREK: Oh my god! That’d be great. How do I know?

But yes, and I meditate every morning for 10 minutes. 


DEREK: My goal is to eventually get that up to 20. But I started with 5, I moved up to 10. Every morning after I do my little back exercises, routine. 

I try to eat relatively healthy. I’ve recently been getting into craft beers which is not healthy, but it can be healthy. Otherwise, I live a pretty balanced life, I would say.

PHILIP: Cool. What is your biggest productivity hack? And I know you have many, so narrow it down to one.

DEREK: Just one?

PHILIP: Just one, if you can.

DEREK: How long do we have? No, I’m just kidding.

PHILIP: Oh man, those Gmail tutorials. 

DEREK: Frankly, my best productivity hack is always time locking. I think multitasking is the biggest time killer. The more I can bulk process, the more interviews I can do back to back, the more in-person meetings I can do back to back, the more emails I can check and not get out of my email inbox, I do this on a week to week basis, I do it on a day to day basis, every moment of my time, I want to be focused on one chunk of type of work and then move on to a new chunk of type of work, not just do it all at once because that way I’m not reactive, I’m actually proactive. That’s basically, I think, the most important thing. 

PHILIP: That’s actually something—one of the many things I’ve taken from you. I time lock everything. Waking up, today’s product, today’s every hour is accounted for.

DEREK: Good. That’s great. 

PHILIP: And what’s been the biggest lesson…

DEREK: Do you have the time lock that is don’t do anything?

PHILIP: No. I mean, I do, but I never stick to it. It’s usually at 10:00 pm…

DEREK: …30-minute pause during the day and I’m supposed to not do anything. 

PHILIP: What’s been the biggest lesson that you’ve learned since starting Greatist, if you can narrow it down to one?

DEREK: The largest lesson learned, man, so many. 

The one that comes to mind for some reason is that people are always first. Think life is short and building a business is hard. You can’t build a business on your own, and so nothing matters more than the people. That means both in terms of you need to find great people, and when I found great people they have been met and exceeded my expectations and helped us do things I couldn’t have imagined doing on my own. And when real shit happens to people, remembering that this is important what we’re building, but that the people are the most important is something that I think has kept me grounded, and I think that has humbled me, and that continues to be sort of why I think we have a good culture, and why I get to go home every night proud of what we’re building and who I need to build it with. 

PHILIP: It’s been awesome.

And what’s the single piece of advice you would give to anyone right now?

DEREK: Usually my number one piece of advice is don’t do it.


DEREK: Because I want someone to fight with me. I want someone to tell me “No, you’re wrong. I have to do it.” And then I try to help however I can, and introduce them to everyone I know, and support them in any way that I possibly can because building a startup business is not sexy. It’s horrible. It’s hard and takes years off your life. It hurts your personal life. No matter what people say, it messes with your relationships. It means you’re going to spend less time hanging out with your friends and your loved ones. It means you’re not going to know what TV shows are cool or you have to watch as many. There’s so many implications of being uniquely focused, passionate and having a priority in your life that almost nobody does which is building something. Make sure it’s worth it for you. 

Go get a job, come home at 5:30, and watch Netflix. When people tell me their hobby is watching Netflix, I can’t deal with it, but I also kind of admire that and envy that. There’s a part of me that wishes that that was enough for me and that that was satisfying. But for me, it’s not. I sit there, I watch this, and I go “Man, I wish I was creating the show myself. I could do a better job.” or “I wonder what the next Netflix is.” Like, I sit there, and I think in a very different way. And so I don’t think that’s true for most people. I’m not trying to wish it on those people. 

PHILIP: It’s awesome. I think that’s a good place to end. 

Derek, thank you so much for coming on the show. 

Where can people find you if they want to reach out?

DEREK: I’m all over the internet. I’m just Derek Flanz on Twitter and Facebook, I think. I’m just derek@greatist.com if you want to email me. I like emails. 

Just launched a new video series called “What’s Good” which you should check out, and www.greatist.com

PHILIP: Those videos are very funny. Awesome.




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