Gregg Pollack

June 7, 2017

Just as Gregg is a serial starter, I’m a serial networker so we were bound to meet since everyone is a half degree apart in Orlando. About a year ago I had reached out to him. Particularly, I was intrigued by a video he had posted online where he talked about building the ideal workplace. You could tell that he is passionate about this topic. This really inspired me and I wanted to learn more.

I have heard many people label themselves as ‘serial starters’ and I’ve gotta certify that Gregg Pollack is the real deal. He lives and breathes it & his contributions to the Orlando tech community have been immense. Here are a few of the organizations he has founded:

Starter Studio (Orlando’s first tech business accelerator)

Made With Envy (a company that builds web applications)

Code School (an online school that was acquired by PluralSight for 8 figures)

More recently, he has also launched ‘Open SourceCraft’; an online show that shares best practices and knowledge in the code world.

Just as Gregg is a serial starter, I’m a serial networker so we were bound to meet since everyone is a half degree apart in Orlando. About a year ago I had reached out to him. Particularly, I was intrigued by a video he had posted online where he talked about building the ideal workplace. You could tell that he is passionate about this topic. This really inspired me and I wanted to learn more.

How do you build this ‘ideal workplace’? What does that even mean? Where do I start?

Connecting with Gregg led to me being introduced to Laura Gallaher, founder of Key Talent Solutions, who has helped me to continue down this journey of self-development + focus on creating a better workplace. It has transformed my perspective and my mindset for the better. Who would have thought that reaching out to a tech entrepreneur, who is passionate about coding, would lead to me doing a deep dive looking inward?

I have always been impressed by how introspective, generous & forward-thinking Gregg is. There are nuggets and great reminders in our interview for everyone; whether you are new to the workforce or mid-career. I hope you enjoy our conversation:


[Setting: I had set up our lunch interview at a new restaurant, DoveCote, in downtown Orlando. Fortunately, I beat the lunch rush and was able to get a two-top table that was off on its own so we could conduct the interview with some semblance of privacy. A few minutes later, Gregg pulls up on his bicycle. After ordering our meals we had a chance to briefly catch up. Our food arrived just after we started the interview. The music in the background was at a decent volume and there was the sound of plates & silverware clanking as the lunch crowd chatter arrived.]

Dean: Well Gregg, thank you so much for meeting me. I can’t wait to hear some of your answers to these questions.

Gregg: You sound like we’re recording a podcast. Are we recording a podcast?

Dean: It’s a written blog, but I cannot confirm nor deny that [it may be released as a podcast eventually]. Lots of noise in the background though. It may be unprofessional for a podcast since we’re about to be chewing food into the mics.

[Waitress walks up: “I have a turkey burger” Gregg: I meant to ask for some of your ketchup tomato sauce …”]

Dean: So Gregg, I’m always talking about the status quo as something to fight and I’m curious to hear what your take is on what the status quo represents to you.

less afraid of people stealing your ideas

Gregg: Status quo … well if you start from the place of trying to be different you’ll probably be better. You can always do things better. I always tell people that ideas are worth nothing, execution is everything …you know which kind of ties into this a little bit because start with the assumption that you can always do it better, you can always challenge the status quo, and just accept that idea … you’ll enjoy yourself more, I think, be less afraid of people stealing your ideas.

Dean: I’ve gotten into arguments about that … about the idea or execution. There are people who say, ‘well there would be no execution without the idea.’

Gregg: Every idea you can have, someone has already had. Someone has already thought of it. You’re going to win because you can execute better than them. The best thing you can do when you have an idea is tell everyone you know about it.

Dean: Is that what you do?

Gregg: Yeah. Be free and open about everything because you never know when someone is going to have, you know, ‘Oh my gosh, you have to meet my friend, he’d be totally into that idea … he can totally help you,’ or, ‘You know, my uncle would totally fund that, you should talk to him.’ You never know when somebody is going to help you or give you ideas because you just told everyone about it. Ideas want to be free.

Dean: You’ve built lots of things … what is the most remarkable thing that you have built? It is intended to be an open-ended question.

Gregg: Do my kids count? I built my kids.

Dean: How about in the business context?

Gregg: I mean in a business context, it’s probably Code School.

Dean: And what would you say is the most remarkable thing about Code School?

Gregg: So like two things come to mind … the jury is sort of out on what comes first. The first thing about Code School is the people and the culture … it’s an amazing group of people who love what they do and they have a lot of fun doing it. Talking about the status quo, I always try to, when it comes to people and work spaces … I probably heard this somewhere: start from the assumption that you’re always getting in the way of your people doing their best work. Just start there. So it’s about constantly pushing yourself and saying, ‘What am I doing or not doing that’s getting in the way of people being innovative, being creative, and doing their best work?’ Because there’s a million ways to get out of the way and so that’s what we did at Code School, and tried to do that. We created this amazing family of people who care about each other, who feel like work is a safe space where they can be themselves. When it comes down to it, you want to hang out in some place where you can be open and feel free to be yourself … and do your best work and know that someone’s got your back and know that you’re going to get the right feedback that you need to succeed … and that you’re listened to and that people there have your best interests in mind and are helping you succeed on the terms that you’re trying to succeed, whatever success means to you.

Dean: What does that say about the status quo of the workplace when it’s remarkable that a place is safe and you’re listened to and people get out of the way?

Gregg: Most work environments, most companies, are created by people who value significance and competence. They get value from that and most of the time they want to feel significant, they build a business. They’ve been in other work environments where they haven’t felt competent because they haven’t been allowed to do their thing. They create their own business so they can fill that part of themselves that wants to feel competent, so it’s no surprise that the whole openness gets ignored. What’s missing in workspaces is openness … people are not open to sharing how they’re feeling … so I worked pretty hard at that, at Code School, to create that. The second thing that made it really significant is that it was just our aim to create the most effective way to learn programming online, which I think we succeeded at in lots of different technologies and to this day, people often refer people to our courses when they’re first getting started on a new technology because they know they’re going to be most likely to succeed.

Dean: Going back to Code School, when was the first time you knew that you were going to build it? I know before that you were working on video and online media and had an interest in it. When is the moment that you decided, ‘I’m going to definitely going to do this.’

we really figured something out here

Gregg: So every six months, I got into a pattern of creating educational content. Like, I was building a consultancy or doing web application development and so I was surrounded by some pretty smart people that I could trust to get the job done and I could focus on building more video content for developers, which I always had a passion. And so I would build a big project and put it out there for free and that would lead to more consulting work and then I would do it again every six months. One of those projects was Rails for Zombies, which was the first time that we took high quality video that I really enjoyed producing and combined that with the interactivity, the coding in the browser, the gamification and that did so well and got popular really quickly and so we saw that and we were like wow people really love this format. And I got a call from a book publisher that was like, ‘Gregg, we need to talk, I don’t get into conversations with anybody here about the future of publishing without Rails for Zombies coming up somehow’ and so people were really starting to pay attention. So we were like, well okay, we think we really figured something out here. Maybe we should do it again and this time charge money for it. So that’s really where Code School came from. It was just sort of seeing the success of this free educational tool and how much people wanted it and then going, okay, let’s take it a step further and create another course and have people just buy that next course. So we did, we launched Code School, and we probably put like $20,000 worth of work into it and within two months, we got back $40,000 because we would have a course come out and people would buy it and then we do that again … and spend more money building the course and then over the course of two months we get back about $40,000 and we thought okay. So we’re pretty lucky in that respect that it was just very instantly profitable, but it wouldn’t have been if I hadn’t spent the last … you know … the prior five years building an audience, producing content, so by the time we produced Rails for Zombies and paid content, I had a pretty big personal audience, speaking at all the conferences, and what not.

Dean: What you’re touching on is something that I heard you say before in a video online, and that is really a key point: ‘Listen to your customers and what they’re asking for.’ It’s interesting, I heard that probably over a year ago and that stuck with me. Since then, I’ve truly been listening [in a very active way] and it’s amazing by just using your existing customers and your network as almost a crowdsourced focus group on what’s next. It’s such a great tool.

Gregg: Yeah and I’m starting to learn that my next adventure down that road is not just doing survey work. It’s easy to do survey work, like hey audience, fill this out let me know what you want. What I’ve learned from the user experience side of the world is that it’s not good enough just to do survey work. You have to really learn how to do customer interviews, which is something that I will probably start pushing myself to do more with what comes next. It’s what I need to do.

Dean: That’s exactly what I’ve been doing. I took a handful of top clients and just set up interviews to discover ‘what other problems would you imagine Blezoo fixing for you?’ and just listened. I got some interesting and unexpected responses.

Gregg: What did you ask specifically?

Dean: ‘Are there any other marketing challenges that you can imagine Blezoo fixing for you?’

Gregg: Cool. Even that is less open-ended than I thought you were going for. More open-ended would be, ‘what marketing problems are you having?’

Dean: That is something we ask often [so we can create referrals for partners mostly], but also to see which tools in our toolbox could help them. Gregg, so I wanted to switch gears a little bit here for my readers. You’ve stood out in so many ways in your career and you’ve also hired and met a lot of people who stand out. What is a tip for my readers’ careers on a way that they can stand out from the crowd?”

take advantage of these pieces of value

Gregg: There are lots of answers to that question. Companies are all made up of systems, that’s why they function. That’s why people buy into franchises … when you buy into a franchise, it comes with a book of systems. Like, follow this marketing plan, follow this business plan, follow this hiring plan, and this training plan, and you are going to succeed. That’s why franchises are attractive; they come with the recipe book. So, if you really want to stand out what you can do is sort of look at the company that you’re in, look at the systems that you have, and ask yourself: how can I improve upon them? What, right now, is perhaps inefficient? What, right now, is producing waste or even where are we producing things that we could reuse in new ways? That we could take advantage of? And try to help the company, you know, take advantage of these pieces of value that they are not doing anything with or fix the waste that they are producing or the time waste that they’re producing? Make things more efficient. Don’t assume that your boss knows how to run the business perfectly and what he or she says is the right way to do things … look for ways to improve the system.

Dean: In a word, I’m hearing ‘proactive’ because I think that’s what everyone is looking for: proactive teammates that aren’t just waiting for the problem but are seeing ahead.

Gregg: Also, one more thing. What you made me think of when you started that question is, ’In your career, how do you get to your dream job?’ The easiest thing to do is, step one, is find someone who has your dream job. Whether it’s at Disney Pixar animator or whatever, go find those people. And what you find when you find these people who have your dream job is that they’re a lot more accessible than you think they are. So you just reach out to them and say, ‘I’m going to be in the area next week’— even if that’s a total lie — ‘and I’d love to buy you lunch, are you interested? I’d love to talk to you about your career and how you got there’ … and then you just make friends in the industry that you want to be in, that have your dream job, and you make friends with those people, and you hang out with them, and you can say, ‘Hey, how do I get in there?’ It’s just that simple and a lot of people don’t even do that.

Dean: I agree, networking should be a proactive function [for everyone], too, you know? When I ask you, ‘Who the most remarkable person you know?’ who comes to mind and why are they the most remarkable person you know?

Gregg: Who is the most remarkable person I know … I saw an interview with the Dali Lama last night. [I don’t know him, but] he’s pretty remarkable. I liked what he said … he said something that stuck with me. ‘I practice showing compassion and understanding when people are angry at me or frustrated at me.’ I thought that was interesting, the way that he said that ‘I practice this.’ Is it that he does that or that he practices that? How could you practice that? Anyways, that’s just a thought.”

Dean: Who is just the first person, that you personally know, that comes to mind when I say that?

Gregg: I mentioned one remarkable person earlier, Shana [Moore], who I interviewed at the open-source craft show. In less than two years, was able to completely switch her careers from administrative assistant to full-time software developer, so she was pretty remarkable with her determination.

Dean:  If you could just put your humility aside for a second … what is your secret to being outrageously remarkable?

confront the uncomfortable

Gregg: Don’t try. The more pressure you put on yourself to be remarkable, the more miserable you’re going to become. It’s one of those things. The more you try to be happy, the more miserable you’ll become. It’s sort of that … what’s it called … it’s like a reverse law or something. The more you try to be positive, and you try to work hard, and you put pressure on yourself to accomplish, the more miserable you’re going to be. The more you can seek out the things that scare you, confront the uncomfortable, the more positive you will get … the more results you’ll get. It’s all about what’s uncomfortable and what you’re willing to do to be remarkable. What was it, there’s a quote that’s stuck with me over the last few weeks. ‘Happiness is all about solving the problems you enjoy solving,’ so the bottomline is that no matter where you are in life …whether you’re at the very beginning struggling for your first job, or whether you’re retired … every day is a series of problems to solve, even if you’re famous, and if you’re not solving the problems you enjoy solving, you’re going to be miserable. The best thing you can do is figure out what kind of problems you enjoy solving and if you can get yourself in a position where you make money doing it, then you’re pretty lucky.

Thank you, Gregg. I feel even more excited to continue to build the ideal workplace after getting the chance to interview you.


Check out Gregg Pollack’s website to connect with him!

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