CEO of, Investor, Advisor
John E Derrick | CEO of, Investor, Advisor

"It's not the most complicated technology. In fact, it's almost never the most complicated technology that wins. It's the one that actually does the job."

- John E. Derrick

John E. Derrick on entrepreneurship, investing, and shares fundamental advices for founders and CEOs

Talk Takeaways

John Derrick, CEO of SkyWriter, sits down with (JP) Jeffery Potvin to talk about entrepreneurship, investing, and shares fundamental advices for founders and CEOs.


A global technology executive for private or public companies that leads with a measurable and quantitative methodology that has lead to multiple exits as CEO, turn-arounds at public and private companies, and multiple additional exits as an advisor / interim CEO.

The key strengths and skill sets that I use to grow, transform, or turn-around a business – •Strategy, Communication, •Execution. In other words, figure out where to go, make sure everyone knows where you are going and wants to go with you, and then do everything necessary to get there.

The strategy and operational plan is always based on Market, Product, and Team. Once you have a strategy and the right plan, execution is truly everything.

Extensive global experience having sold products worldwide and led organizations with large teams in US, China, Ukraine, Russia, India, UK, Portugal, Poland, France, and Israel. A key strength has been an ability to adapt existing technologies / products and sell them into new markets such as China (US product) and the US (non-US product).

Private company experience: (3 exits)
Founding and non-founding CEO at venture-backed private companies at Chicory Systems (very accretive exit to Parthus), Conformative Systems (accretive exit to Intel), Jelastic (still private), and Tonomi (acquired by Grid Dynamics).

Public company experience:
Various roles at public companies including COO / President (led rapid turn-around from negative cash flow to GAAP Profit), VP, GM, and micro architect / lead at MIPS, Parthus Technologies, Intel, and IBM.

Trusted Interim / Advisory experience: (>5 exits)
Interim and advisory roles for public and private companies including interim CEO / COO, board of directors, and advisor involving Sun Microsystems, NetApp, ARM, Qualcomm, and others.

The full #OPNAskAnAngel talk

Jeffery: Alright, welcome to the supporter’s fund, ask an angel. I’m your host Jeffery Potvin and let’s welcome our investor today which is John Derrick. Welcome. we’re very excited to have you here today john. I know we’ve had numerous conversations. I’m a big fan of all the things you’ve been doing and have done and what you’re going to probably end up doing, which is, who knows the future is going to hold a lot of bright things. I’m sure especially in the deep tech space but I think the best way for us to kind of start off and kick things off is I’d love to have you share a bit about kind of your past, where you’ve come from the things that you’ve kind of worked on through Yale, all these great things that you’ve done and I don’t want to list them all off because I’ll take away all the thunder but I know you’ve done a lot of great things. so please share that and then a little bit about where you are today and then one thing about you that nobody will know.
Derrick: Okay I’ll have to start thinking about that as I’m starting to talk. I’m gonna have to keep it somewhat secret so that it’s still something I’m okay with you guys knowing but that’s okay. I’ve been doing tech stuff now for about 30 years. I’ve started my career out actually as an electrical engineer, deep text-based doing radar systems, mathematics things like that, joined IBM, did about eight years there, lots of different shipping products, 19 patents at IBM, and then left IBM in 99. I started a company, raised about 5.3 million, sold for you know 10x that, something like that. and within 18 months went to venture funds and worked with a bunch of other companies. I started a second company. We sold that to intel. I went to California, led an IP semiconductor company, and grew that as a quickly public company, and then you know led about three other startups as the second CEO with another exit involved in all that. Additionally, I am always looking for something new, something challenging, to fix the puzzle, solve the solution. I always advised a bunch of other companies through that whole process. So I’ve also advised a few dozen different companies as a consultant, advisor, and board member, served on the board of intel capital investment for example, and software-defined radio among other things but about five or six other additional companies I’ve worked with. I have also been acquired through the years by Arm Netapp, Qualcomm, VMware, and others across all kinds of different spaces, so everything from material sciences, haptic devices, company cards by Chemist to pure software things required by VMware. so that’s a quick background. I have done diligence for literally hundreds of different companies across 20 or so different VC firms through the years, corporate and also just pure financial VCs.

Jeffery: amazing. so you pretty much spend a lot of your time, almost all your time in deep tech but also coaching, mentoring, and helping other companies work through the ecosystem at the same time.
Derrick: yeah. I would say the ratio between companies I’ve assisted to companies I’ve led has usually been six to one because I’m always mentoring, advising, and helping some other first-time entrepreneur coming out of, you know, some research project at Yale. a lot of things that they do I don’t fully understand. I mean I got a grasp of it. I don’t fully understand it. I understand it enough to give them advice on how to build your business, what do you need to worry about and how do you mitigate risk in terms of your funding or your productization of your technology. and so I enjoy that aspect of it. but at the same time, I have to have a full-time gig as well. Right. So, I do those as well. So you know technically, I guess at this point, probably have something that normal people might equate to three full-time gigs plus a few more but that’s fine. I enjoy that. so it’s all good to keep yourself busy. I like the 19 patents leaving IBM in 99 kinds of like the Gretzky thing so a very similar look which I like that I’m going to retire in 99. After all, I don’t know 8 million awards and 999,000 goals.
Jeffery: I think that sounds like the same structure before you left IBM.
Derrick: well I say I hope it’s not abnormal but I like to do new things period. I like to optimize. I like to make things happen that people don’t think can happen. That’s the key part of being an entrepreneur. But hopefully, in the process I figure out how I can make some money as well, whether as an investor or an entrepreneur or advisor or whatever.
Jeffery: So I think that’s a great approach. How much of what you learned and jumping into IBM helped you from that machine side of things? IBM has turned out many amazing entrepreneurs especially in the deep tech space. I know many people that have gone through the engine, the IBM engine. how much of that structure and learning do you think helped you and propelled you over the last well 22 years give or take?

Derrick: It’s interesting. so my first role was working at a company that is now part of Raytheon. It was the defense sector and they had a very casual technology-driven culture. you know, wear shorts to work. whatever else doesn’t matter. When I first joined IBM, it was quite free. A right to all of that. Right. So I was like an oddball. everyone else is in slacks, shirts, ties, and whatever else and I’m all wearing my Adidas or 501s, and just you know not sure. but I’m going to be comfortable. I’m going to do what I’m going to do. So that tech-driven thing was fine but when I joined IBM, there were so few people getting hired at IBM that they deferred my orientation class until they had enough people to do it. So when that came around, I was like I’m too busy to tell my boss. He told his boss that this guy can’t do it. he’s too busy doing stuff we need. I never got IBM-oriented so I just did stuff. and so you know it was a great playground, a great environment to learn and I would describe it instead of doing startups within that company. we did upstarts, so the organization has a problem. They have a little bit of funding. they say go do this project. go build it and so I did a bunch of those right and so that was very it’s a very good kind of you know training wheels on learn it figure it out that sort of thing. But the most important part was that you know as you go through a company like that is to learn what’s quite important to the business and then also learn what you just need to take care of so it’s not a problem. Those are two different things. so you know some structure is good. so you just don’t have problems. but you have to always remember what the focus is, which is producing value for the market, creating something people invest in, buy and purchase right and keep people motivated. Well, I like producing value for the market. I think it is strategic in the sense that IBM can’t survive if they’re not producing enough market value. they’re giving you a project which says, hey take this upscale product or business. figure out what you can do with it. see if our clients will like it in the long run but work it right now. figure out the value so while you’re doing that and I loved working with IBM, I think that they carried a lot of that structure and you could always lean on them to help that innovation side find new things. come up with creative ways to solve problems using that deep tech but that process of analyzing things. So in taking that, how much of this helped build street cred for you because now you spend the next 20 years and everybody’s coming to you to advise the coach. So street cred has a short half-life but that said, I will say that you know in that environment, and there’s a lot of large companies that you can quote exist and survive for quite a while with action without actually shaking things up. I would say if you’re an entrepreneur, you’re going to be leaning forward all the time trying to figure out, this doesn’t make sense. We could do a lot better for our company, for our team, for whatever is right for a customer. let’s do that right and you’re going to be doing that as opposed to, hey, it’s not my problem this is the way it’s done. I’ll be fine. I don’t worry about getting paid either way. That’s the real test. do you have it in you to be an entrepreneur or not because if you’re trying to improve it, build it, expand it or create it, you’re saying I want to put myself out there to take a risk to improve what is around me whether that’s a business, the product solution or the customer experience. what it might be if instead, you’re like, hey the system’s working, I’m getting paid. I’m okay. how can I make more money and that’s all you’re worried about that don’t go into entrepreneurship? you’re gonna get crushed right because as soon as you figure out that you know, hey this is hard. this isn’t what I wanted. I just wanted something to make a lot of money. you’re gonna get disillusioned well before you get that chance to make a lot of money right. if that makes sense. it’s kind of either doing punching the clock doing status quo or you’re going to take what you’re doing and utilize the skills and improve its expanded model so that you can challenge what’s going on in the business, so that that’s going to build up more of that street cred for you because people are digging into you, saying hey this guy’s going a little extra mile. here they may be uncomfortable with it, but your clients are loving it because it’s making the money. it’s making them see the vision. it’s letting them understand that, hey this tech might be new but it’s going to be somewhere in the next few years. we better jump into it. so you’ve got to create that funnel and I’m assuming that from that it built up that entrepreneurial side to you, probably thinking, hey you know what, I could survive and do this myself. and a lot of it has to do with a great deal of, I’ll say impatience. things have to happen. They have to happen faster and faster. and so you know sometimes there was a phrase for a while I’m not sure if it’s still in you. so don’t ask for permission, ask for forgiveness. I actually would take a little step further and I’ve used this on board members which are, don’t ask for forgiveness. be an entirely different place in your business. when they even realize there’s a question, just keep blowing through the neighborhood. That’s very true right because you know ultimately people don’t care, you know, do it ethically. do it legally. do it with all the right care and respect for all the different things you need to do but ultimately you know you’re responsible for your company. you’re responsible for your destiny if you’re a CEO or a startup. you’re responsible for the destinies of all your employees which is mind-bending at some point. you’ve got to realize, oh yeah I’m responsible for you guys. you know being able to feed your kids as well. but once you grasp that right, you just have to go with it right and you’ve got to realize that you’ve got to move faster than you ever thought you could before right to make things happen and get rid of all the bureaucracy. we got procedures, we got committees and we got whatever else. when you’re just coming down to results and as a team, the whole team has to realize to release everyone that stays as part of that team. but you’ve gotta move as a team in lockstep. you know creating, delivering, making decisions, and moving down that path. and startups are bobsled runs. The reason I say that is, it doesn’t matter if you wind up coming out the bottom of the bobsled, right side up or upside down or crossways. you’re still coming out the bottom right. and so once you start it, once you start that process, you’re popping out the bottom right. it’s just a question of how intact you are when you get there right. you know how much money you’ll receive, whether you’ll be broke, whether you’d be broken or whether you’re going to be like you know, yay we survived, we made it. we made tons of money right.
Jeffery: I like that and I like to use the line that whatever I don’t do today, I fail tomorrow. so there’s got to be that urgency to keep driving you because I think a lot of the time we don’t always see further than today. We have to keep looking a little bit further out and I think that that is where you know taking the roles that you’ve taken as a CEO. you’ve probably jumped in with this tech because you could see where this is gonna go and right now it’s in its infancy. so you might be at the top of that bobsled run, uh and you know what you might not have the best bobsled. but while you’re going down you’re building it. you’re building some track and you’re making yourself down because you want to get to the bottom. and like you said, put your arms up and cheer that you won. So does a lot of that come from thaT drive and vigor to change the world? it does right on a local level. the other thing is you mentioned that looking out ahead of everything else. At this point, I’ve advised dozens and dozens of different early-stage startups and everything else. and I’ll tell you just as an observation. I’m not sure if we won’t go into it much deeper but many early first CEO type role kinds of leadership, one of the places that they fail is they think of everything fully sequentially. they think, hey this is gonna happen? we make this decision and after that, we’ll worry about everything else right. and so one of the things I think that separates people that can kind of figure this out and those that can’t are people can who can visualize right the whole path, the whole trajectory, the arc if you will right of their startup everything that needs to happen over time and then prior prioritizes when they need to think about when they need to resolve when they need to decide the different things that need to be decided right. and you know it’s a little bit of a mental compartmentalization problem maybe but it’s very advantageous to be able to say, hey, this I don’t need to worry about until six months from now or nine months from now right. and to counter that the other thing I’ve seen is people who, and this is something I’ve tried to ingrain in my management team, some people have hired is, if someone comes to you and says, hey, we’ve got a decision. we’ve got to make it right. The first question you always have to ask is, hey, is this a decision that requires me? Is it important enough that I need to care about it if it’s not delegated? empower them. make them feel good. make them grow right. if it is something it requires me, you know, do we have the data we need to make the decision right. If we do make the decision, move on. If we don’t we can get the data to make the decision, if we can’t in a reasonable amount of time and effort, then make an assumption, make a decision. Otherwise, get the data to make the decision but you always have to move forward. you’re always processing as a leader. You always have to figure out where we are going, what we need to do, what are we encountering now that we’ve got to decide on right now so we can move faster than the competition, whoever that might be. so do you think when you’re in that same context of always moving forward and getting people to repel their mind and their business initiatives forward, Is it the job of the CEO and as the entrepreneur in-house, that is the CEO, is it their job to kind of poke the bear and to get these things moving? and where do they get that learning from? Where do they understand that? What status quo isn’t great? You know Things are calm right now. but that’s not the way to run your business. You always have to be reinventing and changing and trying to push that line further and further ahead. What gets that mentality? How do you train or how do you coach other CEOs while you’re CEO in your own company? How are you getting people to get to that same line that you’re pushing?
Derrick: yeah so for me, it’s probably a personality trait. I’m just not comfortable with the status quo right. things have to change right. we’re either growing right. I have been in both situations. I’ve been to companies where we’ve been growing rapidly. I’ve also been thrown into public company roles. you know officer level, where we had a company that was struggling and I had to go in and say, this doesn’t work we’re changing everything right and rip it up, add new people, switch it over, grow the business. So I think from an entrepreneur the whole thing about entrepreneurs is, an entrepreneur is not comfortable, is not satisfied with what is right now right. whether that’s we need to grow it or we need to rebuild it, remodel it, fix it, whatever it might be right. and so yeah to a large degree as a leader, you’ve got to set that standard but at the same time you also really have to realize that when you’re hiring people into your company or organization, there are people that are not comfortable with that level of uncertainty. When I look at companies from a diligent standpoint or working with them, there are always three things I look at. one is what’s the market we’re trying to reach? What does that look like? Where is it? Can we reach it from where we’re located? The second one is what product or offering do we have? does it match up well with what that is. and those two things you know most people kind of think about that a lot right. The third one is the team. it’s not just the individuals, it’s the individuals. It’s also how the team interacts and whether they’re assigned or structured in a way that works well to address the challenges and the goal that they have as a whole company. and there are people who just emotionally, just for their well-being, should not be part of a startup. they just need a level of structure and every day is good right. everything is kind of structured and predictable that you just can’t offer in a startup. and there’s nothing wrong with that. it’s just don’t torture them with that process. I’ve had VP-level people who worked with me early in my career that were not wired for the uncertainty that was going to come in. what we did and we were successful but they were stressed out of their minds the whole process. So anyway, it’s always yourself first. know your company and know how you’re going to address the problem, the challenge. it’s a different flow than some other companies might be.
Jeffery: Well I like that it all comes back down to, no matter what you’re going to market at, it comes back down to the team. so your team is really important to support all of this and you’ve found this through your multiple company growths and exits. the companies that you support, that you always had to have that team, now being early on in a precede, all the way up to a series e. I could probably say that 99 of that team probably won’t be the same team that you had in the precede that you’re going to have at that series e. but in that growth, as you said, you got to be able to change things, know yourself, know your team, know your company, know the challenge you’re going after. but all of those can change and they’re going to change year after year and you have to adapt. So how do you break through that fears because I think we have this fear that when we build this first team, this is my team you know, this is the best team in the world and they don’t see past that vision? because right now all you see is what you’re trying to hit that first milestone, how do I get over the fear that I have to keep making changes, that I have to force better smarter people in this realm because that’s what’s going to get me to success?
Derrick: I think there are a couple of pieces there. one piece is yourself. So I’m very okay with some guys getting an idea in the lab, some university, somewhere we gotta figure it out and I’m okay with you know public company roles. I’m presenting the exact intel. I’ve been there. This is what we needed to do. I got acquired. The guy signed the check. The guy I acquired from Intel was Pat Gelsinger. right before he came back last time, this is the previous time. so comfortable with all of those things, I wasn’t comfortable with stasis. I got to be moving. so that’s my biggest issue but you’re going to have people who don’t scale. you’re going to have people who they’re comfortable with at a certain level with their abilities, take them to a certain level. they’re not going to want to stretch beyond that. the thing you always have to be looking for in a company is even in my role as a CEO, you’re looking for, how do I grow the company to where we can hire someone who can do the jobs better than the people that are there. always a key thing. and this gets back to someone who’s in a startup. if you’re in a startup, if you’re doing it right, you’re very confident in what you’re doing right. you’re very confident that you’re going to be able to create massive value and when the chance comes or when the opportunity happens where there’s probably someone better for the role than you are, then you’re going to find a new role in that company or somewhere else. but the point is the value that you’ve created that company will be in good hands with that next group of people who are going to drag it, push it, move it along. and so if you can get comfortable with that, which a lot of founders can’t, I’ll just say, you know honestly, a lot of founders are like, hey, this is my deal. no one else understands as well as I do and I’ll just challenge anyone that says that to say investors are smart investors. they recognize your understanding of that market but they also have a lot more experience than you probably do in scaling companies. and you know, if you ignore that, you’re going to leave a lot of value behind. If you fight that, you’re going to lose a lot of value because really what you want to do as an early-stage founder is you want to create a company where it can go like a rocket. and if you’re not the fuel for that rocket, you want to get someone in there that can drive it faster farther than you ever could. and then you go do something else. you go create another launch. you go start something else and get that moving. but it’s all a financial transaction. if it’s just for the love of, I want to do this thing because I’d like to create whatever, you know that’s got my mark on everything else that’s no longer a business. That’s your identity. That’s everything else. it’s a hobby or whatever it might be. but if you’re focused on, I want to create enterprise value over and over and over again, you got to get past that and I’m sure that probably raised a bunch of psychological questions on me. But that’s okay, that’s right. no not at all. I remember learning this lesson when I worked in IT at Loblaws and they said, you got to learn to let go. you got to move forward and it’s always about propelling yourself forward. I remember sitting in an elevator and my boss at that time after this big heavy meeting turned to me and he’s like, you okay? and I looked at him. I’m like, yeah this is awesome. I can let this go and move on to the next thing. and he looked at me, like wait for a second no you need to drive this thing into the ground. I’m like no man like we got okay. this thing’s handed off now. Let’s go forward, and that’s that entrepreneurial mindset of how can I keep creating the status quo and break it and make it better and move it forward more. I think founders sometimes get stuck in the position of having too many pain points and I can’t see around the corner and I can’t leverage myself to get over that because the risk is too high. they forgot all the risks they took to get there so then they got to comfort level and then they can’t figure out how to kind of keep bumping it forward. and you know sometimes you gotta throw a bomb in there to kind of shake things up, and that could be a new hire or a changing team, or a new product. Whatever it might be, something has to keep propelling you forward and you have to keep thinking about how to make that change to move one more notch forward. to put it a little bit differently, I was at IBM for about eight and a half years which for an IBM person, that’s not very long. it’s like people talking about being there for their life and all that father-in-law retired their rights spent 30 some years and that sort of thing. but to me, it wasn’t eight and a half years at IBM. It was five different technology projects. Then when I finished one, I looked around. I said oh I can go work on that. they assigned me to that. I went and did it, built it, constructed it, sold it, conquered, and then went to the next challenge. and so it was a series of opportunities. so IBM to me was not so much a company to work for. it was an ecosystem in which to innovate within because that makes sense. and so even if you’re not launched out, you’re not part of a startup, whatever else private company, think about where you’re at, where can you innovate, what can you create, where can you start building value right on that kind of challenge type basis. and the beauty of course in a company like that is if it fails great, you get another chance. that’s the beauty of it because you know you got your retirement. you’re going to still work there. as long as you don’t suck, you’ll be fine. but the downside is the up. The downside is the upside, it is just a better salary, it’s a promotion. It’s a few stock options or RSAs. it’s not that big so you just have to decide where you want to dial it in.
Jeffery: yep agreed. So now taking this, I guess the best parts of what’s occurred through your IBM days and the CEO side and raising funds and building up this business and finding ways to keep changing the status quo and growing the company you started to do a lot of add-ons to your whole journey. and one of them that interested me a lot was what you were doing with Yale. Can you share a little bit of how Yale started and where that ties into your whole journey?
Derrick: so just to put some context in it, I’ve advised a few dozen different VC funds on different investments and things that they’ve done through the years dived into those projects as a coach, to their CEO. so, the CEOs intro CEO roles management team strategy, everything else. I’ve also worked with several different universities that have tried to be working on commercialization of technologies and several years ago through another group that was trying to do a kind of incubation of silicon or hardware-based technologies. I advised a company up in Yale and worked with them, made significant progress, kind of demonstrated that. and through that process, as Yale was trying to create an EIR program to, from industry, help their researchers or teams figure out what to do. I started working with them on that and so I see early-stage tech from different universities. whether that’s material science or computer vision or you name it. from different universities where they’re like, hey, we’ve got this thing. What do we do with this and this is like my sweet spot. To be honest, because I understand some tech, I look at the market and figure out a whole structure of how to drive through it. and really for me, it’s not just an interesting thing to do. It’s something I feel strongly about because if we’re going to develop things, let’s develop things that actually can make a difference in the market. The world creates value. and so I’ve been involved in a bunch of those projects through different things and those arranged in the case of Yale, it’s material science. It’s a memory. it’s battery tech, battery recycling tech. so it’s everything from computers to green tech to other material science stuff.
Jeffery: So awesome. So in that part of what you’ve been doing with Yale, are you tied into many startups and working through that ecosystem as you’ve built out kind of the process on how to scale and how to commercialize? it sounds like a lot of it’s on commercializing innovation. So are you doing that with a lot of products and businesses? so I think at the moment, I’d have to check the list. I don’t have a list in front of me. I think I am probably working with like eight different companies right now, early-stage startups. We’re trying to commercialize a technology that originated in a university lab. In addition to that, I also work with a couple of groups that are trying to commercialize technology coming out of national energy labs. so for example, one of the companies I’ve worked with, they’re out of Oakridge National Labs. They did research here in my area. another one’s doing a project to do miniaturization of technology at Argonne. Another one came out of yale. It’s just a pretty long list and kind of geeky. To say the least, which is fine, which I’m okay with because I’m more of hard science, technology, or something. how do we then create value from that and minimize the length of time it takes from IT work on a lab bench. Now how do we build a product? so I’ve been through that project trajectory. at least at this point at least a dozen times with different companies. and so it’s pretty you know. Even if the technologies are considerably different, the process of getting them out is pretty similar but you did help kind of build that commercialization. I think that makes a big difference especially when there’s going to be a lot more companies over the next 20 years coming out of Yale and they’re going to need that understanding of how to commercialize it and you’re sharing that down and helping others learn more about what this kind of vertical looks like. and how to get not just with them but any of the universities generating deep tech. Whatever it might be and from my perspective, it doesn’t matter. If someone says this, it doesn’t matter so much. if someone creates this magical breakthrough in a lab that’s going to create green energy, clean water, nuclear fusion. Whatever it might be, it doesn’t matter if someone builds that in the lab. but it never actually happens so I’m just throwing some effort and brainpower behind. Let’s take some of these things and get them in the market where it makes a difference. that’s it right. pretty simple.
Jeffery: I think that’s pretty exciting regardless and especially being able to do that with a lot of the companies on technology that may never even hit the world so there are some fascinating things that people have created and you’re theoretically right. That would be great. be wonderful. if we could put some energy behind that, not look for the magical next thing that may or may not happen.
Derrick: But so much of it. I would say so much of the role of the entrepreneur is not quote raw research technology development and I’ll confess to a couple of things here. my first startup we built a technology that was co revolutionary. but it combined hardware processors like co-processor type technology and just-in-time compilation technology in a single tool. Both of which were well established. we just kind of meshed the two together differently and it was a phenomenally good idea. but how much raw research new technologies it would. we’d develop not a ton. A lot of it had to do with just making it palatable to the market. And so one thing I would challenge any entrepreneur that’s looking for a deep tech entrepreneur that they’re doing to think about is one thing: to build something no one else can build. It’s a whole nother thing that will have more impact. if you can take the thing that you can build, someone else could too. but you just do it first and you just do it in a way that is more packaged, more palatable to the market than anyone else because you understand that market space better right. and get it out there and get it done. How many times have people said apples don’t do anything that other people can’t do? it happens. People say that a lot. it just happens to be that they are packaged better. They focus on what people need. package it and then turn around and sell it. So many times it’s not the most complicated technology. It’s rarely the most complicated technology that wins. it’s the one that actually does the job but is packaged well that does it and that’s the one that has the most impact. so if you’re trying to green up the planet, have better energy efficiency, solve the computer security problem. These are all things I deal with every once in a while. do the thing that people will use right but do the thing that has market share. That’s the thing that’s going to have the most impact.
Jeffery: I agree. I like that. and learn to commercialize because I think a lot of what you’re doing is and commercialization can mean a lot of things. but it’s creating a great supply chain. It’s processing things, making sure that you’re running lean and mean and with no errors, and finding ways to keep reinventing and building values. so there’s a lot of different ways to commercialize. but I think it’s a big piece of how this motion has to happen for the business and that leader has to be able to take that with their team and help that ball keep moving forward. and commercializing is just a lot of its process and a lot of it is to change a whole industry. create something that you can sell that replaces the way that industry works with something cheaper, more efficient, and makes more money. and it’ll take it over whether you gain all the market share for it or not. it doesn’t matter. you will change that industry and that’s letting the economics work for you. don’t fight the economics of the whole process.
Jeffery: I love it. three things that you want to share about being a CEO of a startup and building a company. What are three things that you would teach to somebody today that stood out in your experience that you could say that, you know what, look at these three things when you’re building your company?
Derrick: always hire above yourself. if you’re hiring people that you don’t think are smarter than you for doing different roles then you’re an idiot. they’re not. they may still be smarter than you but it’s not because you’re thinking properly yourself. it’s just because you’re an idiot for hiring people that aren’t better than you are anyway. so that’s one. The other thing is always to make sure that not only do people understand the vision of your company, what you’re trying to do, but also make sure that every individual in your company can understand what role they play in that. because if they’re part of a company where they believe in the mission but they don’t understand how they fit doesn’t help them feel secure. It doesn’t help them feel motivated. so make sure that they know that. and then the last one is to be pragmatic or honest. I should say be honest about yourself regardless of what you accomplish. you’re just a person trying to figure this out with everyone else. you just happen to be in a different space than somebody else. so don’t be a jerk with other human beings. treat them with kindness, respect and work through that problem and see if you can get other people to join you to do that. because I will tell you, in the CEO ranks of startups, everything else, there’s a lot of idiots. there’s a lot of us that screw everything up in our lives and with other relationships with other people. don’t do that because companies kind of come and go. relationships that you have with the people you work with, your family, your kids, everything else, those hopefully, if you do it right will last a lifetime.
Jeffery: Well said. Those are great things to keep in mind. I like the last one. they’re all good but the last one stands out because you treat people the way they should be. and be good to everybody and things will work in the right direction for you. and part of that last one also is not just family and close friends and things like that, but it’s also how you treat other people in business. and the reason I say that is I’ve always taken the approach that companies come and go. I’ve been married for 29 years. I’ve worked with all the different startups, engagements, everything else, a few dozen companies literally and held probably different full-time jobs and your real relationship with other people, your reputation, what people say about you will carry across every single one of those companies. you know the company will come and go. what people think about you as a brand, think about you as you do. I want to do business with them or not, can I trust them with everything else that goes on forever? And so I do a lot of business randomly with people that, oh yeah, I know this guy. Just as an example, you’ve asked me to introduce one of your companies to a guy that I used to work with literally 24 years ago. So if I screwed him over then sorry. but, if it was not a relationship, no way would make any sense to even try to have that conversation. and so be a decent person to the people around you. you can be an aggressive entrepreneur and not be a jerk. so I’m hitting the like button like crazy right now. there’s like going up on the screen. but I completely agree with you. I think sometimes we get caught up in our own thing and we forget that we’re all human and we’re all working on the same trajectory. \we’re all trying to figure it out. optimize for where we’re going and for others hopefully those around us. So yeah, I like it. Well, we’re going to kind of transition a little bit into one of the one areas that I always like, which is a great story. and looking for and all of the startups and the businesses that you run and the people that you come across, the stories that you hear, is there any kind of heartfelt story where it blew your mind away from how this entrepreneur, how she or he was able to overcome the barriers and take off like a rocket ship or they at least survive? uh, maybe it was a coveted story who knows. but he was just kind of looking for a story that shows what it takes to be an entrepreneur.
Derrick: wow. a little forward warning on this one. It would have been great. I’m thinking it’s okay. so I’ve been involved in companies in all kinds of different places. one of them I’m drawn to is, I was hired as a second CEO. kind of replacing a scale-up for a company that was based in Ukraine. and so this was before the revolution. whatever you want to call 2013. and there were I think15 out of 50 people there. sorry, most were men. Most had served in the Ukrainian army in the IT service. There we started scaling the program. we got things moving. It grew revenue in the first year, about 350 percent. so pretty good revenue growth for a staffing company. I got a bunch of telcos, things like that. but in the backdrop, we were raising capital. and so we’re raising capital from a US-based firm. when the revolution happened, and I can share pictures probably, not right now. but I can share pictures like in the square with the barricades, the bonfires, riding and shooting all that kind of stuff. but these guys were like, this is where we live, we want to build a tech company. We want to be important. We want to make this work. and so they kept going. The funding source in the US didn’t happen because the firm didn’t name them. but the firm in San Francisco was not wiring three million dollars into Ukraine. that doesn’t make any sense. and so they started raising another capital raise out of Europe. and got that sort of moving along and then the jetliner got shot down. but these guys are still building their stuff. they’re still selling. we’re still plugging along and so you know here in the US, I can’t continue with this pack, my marketing sales team that we’ve built up here. we can pay for them, the current investors won’t do it. We couldn’t get new investors and they are still going. The point is they’re still going and so even in the interim of all of that, a bunch of them got drafted right to the Ukrainian Army. I was going to get sent off to the Eastern Front. They went to a different country for a while leaving their families behind to keep working. and so laptop’s hotel rooms typing away working while I’m here in comfort but they were just dedicated to make this work. We don’t care about geopolitics. We don’t care about getting deported. whatever else is going to happen. and they’re still going. and so I think you know the thing I would just say, there is just the tenacity and you got to have a certain level of this tenacity and the stubbornness to make this work. and you know believing in it enough to do that it’s not a gig, it’s not a job. it’s a mission that you set out to do because this is something important enough. I think it should be made. it should be built. and maybe not as dramatic as stories you might want, but it’s one that kind of sticks with me. it shows that nothing can get in front of your dream and it doesn’t matter if the funny didn’t come in here and this person didn’t like this. It’s the fact that they were going to war in front of their window that they got. It’s also a reminder that sometimes when you go into this, you do need to recognize that it will put some stresses on your system that are unusual. So if you’re used to an easy, normal nine-to-five type job, this is not that right. you’re going to be thinking about this or you should be thinking about this 24/7 with an occasional break for mental health. but that’s about it.
Jeffery: yep. I like that, that’s a great story. and I love it, tenacity and the desire to make sure you get success out of something. you’ll just keep working hard. Alright, we’re going to transition now into the rapid-fire questions. These are going to be business questions. it’s one or the other. so it’s an easy quick snapshot and then we’ll jump into some personal stuff. so alright first question, founder or co-founder? pick one or the other. Would you take a founder or a co-founder? like which one do you represent. which one would you rather invest in, either unicorn or four-year 10x exit for your CPG tech brand or tech ai or blockchain ai? First-time founder or second or third-time founder? what they did the first and second time is not an option. That’s the mystery. first money in or series a first? angel or VC angel? okay alright, we’re gonna jump into the personal side now. These are the fun ones, maybe a book or movie?
Derrick: movie.
Jeffery: Superman or Batman?
Derrick: batman.
Jeffery: pizza pop or ice cream bar?
Derrick: I’m gonna go with ice cream.
Jeffery: That’s alright. five minutes with Bezos or Oprah?
Derrick: oh Bezos.
Jeffery: Arsenal or Manchester United?
Derrick: Manchester United but sorry I gotta give a caveat here only because I had a VP of marketing that I worked with at two different companies who are huge Manchester fans. It is about relationships. Unfortunately, he passed away several years ago from pancreatic cancer. and so I’ve got to say Manchester United for the team.
Jeffery: it’s good, I will find an arsenal fan. I’m working on it. I know a few. I just don’t talk to them. All alright now, with a couple of political sides, one question on the political front. So based on all the things that Trump’s done, he thinks he’s good. Do you think anything’s going to happen with this tax issue, yes or no?
Derrick: no not at all. you don’t think that’ll be the little thing that’s going to take him down. I’m not sure what the audience here is but in terms of the bureaucracy fine print of tax processing legal stuff, whatever else on businesses tax and accounting, almost nobody can say their tax return that they file is accurate because it’s just too complicated. so it’ll be at best a minor white crime, white-collar mistake, fines whatever else. I don’t think anything will happen. Now Capone got taken down by taxes but that was a little different. you said a little bit more on the other side of the track so I get it. well, or at least known, the size and magnitude of the discrepancy were larger. So who knows.
Jeffery: true. Alright. favorite sports team?
Derrick: I don’t have time for that much. I’m more of a college guy. so the University of Texas. I used to go to a bunch of Stanford football games which are not very good but they were great. so it’s not good.
Jeffery: I like it. Just before the pandemic, I was down in Pittsburgh and catching some college football. so it’s really good. College football is a big thing so my team where I went to school was really bad. but it’s still fun. it doesn’t matter. you don’t need to win in football to be happy in companies. you need to win to be happy. so I know this may not work but what favorite movie and character would you play in the movie?
Derrick: I’m throwing this out there. I’m not huge into that but I’m going to throw in the Truman Show. Alright. so you may not hear that one very often and the reason is that it kind of realizes the whole process that he needs to be himself and don’t worry about how the system is trying to drive him. I think from an entrepreneurship perspective, I say that only because we’re in this call. but be yourself. understand who you are and figure that out. and that’s pretty important whether you decide you’re going to be an entrepreneur business guy. whatever else you’re not a business person or not, doesn’t matter. The most important thing is to understand who you are so you can be what you want to be right and that’s what I got out of the movie. but that’s probably highly tainted by my wiring.
Jeffery: That’s good. I’m going to have to check that out. It’s been a long time since I’ve seen the show but it’s great. Alright. our second last question because we didn’t answer the first one, what is your superpower?
Derrick: My superpower is probably figuring out people’s personality traits pretty quickly, understanding them. so I’ve tried to become a student of understanding. How people are wired is incredibly important and so it’s more of a long answer to the question but I believe strongly in a bunch of different psychological personality tests. and so one of them is a circle, a square, a triangle, and either zed or a squiggle. It kind of tells you a lot about the person. Most people can tell them what they’re going to score on the thing before they even take the test.
Jeffery: nice. Can you tell me what I’d score? Because now I’m super curious.
Derrick: I would say you’re probably a square or as or a z. but I’m gonna go with the square. so you can go look online to take the test but now you can’t take the test. if you search on google, you’ll find it. just personal disclosure, I’m a z. you’re a z. alright, you can look the thing up, and then you’ll figure it out and then it’ll make perfect sense. Jeffery: I’m going to check this out. Alright. so the last question was the first question, one thing about you that nobody would know.
Derrick: I try to run pretty transparently in life. So I’m not sure if there’s anything that other people, at least someone, would not know about me already. I could go through a whole list of things that you guys don’t know about me. I have an identical twin, for example, that’s essentially a mirror opposite of me. So he got my BS double E in Mathematics Electrical Engineering type stuff. He got his degree. He got a Ph.D. in biochemistry and then a law degree at Berkeley. he serves as a patent judge, taking forever to make decisions. I tend to make decisions super fast. we’re kind of like mirror images. We understand each other but we’re different. I don’t have a lot of what no one else knows about me. I got almost nothing.
Jeffery: I think that works so john. I appreciate all your time today. Fantastic. I learned a lot. I took a ton of notes. great journey. love that we got to share that today. I appreciate all of your time.
Derrick: I’m going to say the other thing because I mentioned the personality test thing with the squares shaped or whatever else. The other one is very different if you look at the different personality profiles, Myers-Briggs. I don’t know which order because I’m kind of dyslexic. That might be a secret. I don’t know. so I’m a very strong ENTP on that profile, so slightly extroverted. everything else, intuitive thinking, and perceptive is kind of off the chart. And so I spend a lot of my time interacting with other people trying to remap, hey, here’s the solution. This makes perfect sense to me. this is why it makes sense whatever else I spend a ton of my time trying to figure out how to explain it to the people who oftentimes are engineers or technical developer type people who think about things not as being perceptive, like here’s the answer but rather, going through a whole process set of steps of how to get there. I’ve spent a ton of time in IBM, even got some performance reviews of, ‘John usually has the right solution. He listens to what he says and he just says what he’s going to say.’ it all kind of boiled down to thinking about this in a non-linear path and we’re thinking about it linearly. and so I think the other thing, encourage people to understand yourself. understand what’s going to make you happy. understand how you think about things. understand how you react to the environment around you, not necessarily compensate for it. This is the last word I would like to leave with you guys. understand how you’re wired so that you can optimize that value. For example, I’m not going to be a long-distance runner or a sprinter or anything else for that matter because I’m just not that person. but if you’re a sprinter, you’re not going to start saying, hey I’m a sprinter. I don’t do well at long-distance running. I need to improve on that and focus on that. so I can be better. don’t do that. understand what your strengths are. focus on that. understand a little bit about what your weaknesses are and if you’re developing your team as a CEO or whatever else, hire people to cover those spots. hire someone to compensate for the fact that you’re not good. for example at sales, or not good at marketing or not good at whatever. cover it but don’t smother what you’re good at because you’re trying to compensate for that.

Jeffery: I love it. Well, John. I like to end the show by giving you the last word on things that you want to say to the investors of startup people. and you’ve done a great job by actually doing that now. so I don’t even need to use that line but I appreciate it. Thank you very much for that. optimize your value. You said a lot of valuable things. I appreciate your time again John. Thank you very much. Awesome.
Derrick: Great. glad to share it and look forward to talking more. Bye guys.
Jeffery: Okay that was John Derrick. a lot of great stuff there. I liked his journey. he’s done a lot of great things in the entrepreneurial space not only from building companies, working at IBM, filing 19 patents by 99 but just the sheer value of and you use that a lot of value finding value expanding, building products in the business that can bring value and solve problems. he’s done a lot of great things. you gotta understand yourself. I think that was a real key point: figure out who you are and then figure out what you’re trying to solve and then build a team around that and understand how that team’s going to do it. Commercialize, learn how to commercialize your product. He does that a lot working with lots of different startups and businesses. He has a vision. understand how to execute the vision and then commercialize it. I’m starting to love that commercialization piece because I think it’s going to make a big difference in how businesses and startups look at everything. Thank you again for joining us today. If you enjoyed this conversation, please subscribe to our YouTube channel and follow us on Spotify, Apple Podcast, or Stitcher. You can also check us out at or for our startup events visit Thank you and have a great day.

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