Scales Of Success Podcast

#29 - Criminal Past, Legendary Future with Keegan Caldwell

• Marcus Arredondo

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How do you rebuild a life when everything has fallen apart? In this powerful conversation, Marcus chats with Keegan Caldwell, whose journey reads like a testament to the human spirit rising from addiction, legal battles, and self-doubt to founding a global law firm without ever stepping foot in law school. Keegan shares the turning points that reshaped his soul, the quiet force of discipline, and how service to others anchored his new beginning. If you’ve ever wondered whether redemption is possible, this story will reignite your belief in second chances and the greatness within yourself.

Dr. Keegan Caldwell is the Founder and Global Managing Partner of Caldwell, a leading international law firm. Once battling addiction and adversity, he transformed his story into one of resilience, leadership, and service. Today, he stands as a trusted advisor to global innovators, a living reminder that even the heaviest pasts can forge the brightest futures.

Learn more about Keegan Caldwell:
Website: https://caldwelllaw.com/about/
LinkedIn: https://www.linkedin.com/in/keegancaldwellphd/
X: https://x.com/Caldwell_IP1
Linktree: https://bit.ly/42zsyai

Episode highlights:
(3:18) Substance abuse and early struggles
(6:59) Joining the Marines for structure
(8:41) Post-service setbacks and legal troubles
(15:50) Rock bottom moment in Michigan
(22:00) 12-step recovery and rebuilding life
(24:24) Returning to school at 26
(28:27) Why Keegan chose a PhD
(36:04) From the patent office to founding a firm
(43:11) Common myths about IP law
(47:36) Mentorship, fatherhood, and leadership
(51:01) Outro

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Note: The transcript was generated by AI and may contain errors.

Keegan Caldwell: 0:00

And at that point, when I made a decision that I wanted to turn things around, like I said, it was fleeting a little bit, but I was just broke down. Whatever that rock bottom moment is, which it's different for everybody, for me it was this cold, wintry Michigan night where I didn't have any place to go. I'm near the hospital and I decided to go in and be like listen, I need some help.

Marcus Arredondo: 0:26

Today's guest is Keegan Caldwell a Marine, a scientist, an entrepreneur whose life reads like a redemption arc with global impact From being arrested 13 times and facing the revolving door of jail and addiction to founding Caldwell IP, a law firm that started in a windowless room at MIT that now has offices stretching from Boston to Tokyo. Keegan's story is a lesson in discipline, risk-taking and resilience. He shares the pivotal moment a cold Michigan night where desperation turned to hope, and how the GI Bill launched him from high school dropout to earning a PhD in chemistry and passing the California bar, without ever attending law school. But beyond the titles, what resonates most is his commitment to mentorship, bringing intellectual property rights to incarcerated entrepreneurs. Using his past not as baggage but as fuel. He brings that same drive home, raising his kids with vision boards and monthly check-ins, proving that the best stories aren't about perfection. They're about persistence.

Marcus Arredondo: 1:16

Keegan's life serves as a blueprint for turning struggle into strategy. Let's start the show. Keegan Caldwell, thank you so much for joining. I've been chasing you for some time now and I'm really grateful that you're finally here.

Keegan Caldwell: 1:27

I'm so glad to be here. Thanks for being persistent, man.

Marcus Arredondo: 1:31

So you and I have come in contact with each other through a separate group, which I want to talk about, strategic Coach, as it relates to some broader themes within your life. There's so many things that I find interesting about your perspective. I'm looking off to the side because I want to make sure that I don't mince any of this, but you are the managing partner of an intellectual property law firm, but you never went to law school. Is that correct?

Keegan Caldwell: 1:54

That's true. We don't just do IP now, we have a corporate practice as well, but we started with an IP boutique. That's right.

Marcus Arredondo: 2:00

Okay, I'm glad that you clarified that. I find that super fascinating. You have a background. You have a PhD in chemistry and physical chemistry from George Washington University. You've got a background in biomedical sciences. All of that, I think, is super fascinating. How you got into law I want to talk about that. But you're now the third or fourth veteran. You were at the US Marine Corps correct.

Keegan Caldwell: 2:22

Yeah, I was in the Marines too. Yeah, exactly. Yeah, I did that right after high school. Yeah.

Marcus Arredondo: 2:26

So I want to talk about that, but I don't know if it was preceding that or concurrent with it. But I want to talk a little bit about your substance abuse area. I know that there were some felonies, and this area of your life comes back full circle. That I want to talk about as well. Yeah, as well. But this sort of beats on a drum that I've seen relevant in a number of different guests those who are entrepreneurs, those who are successful in their own right, how they incorporate some of the discipline, the mindsets, the challenges that they've encountered through substance abuse and sort of getting through that. So I just wanted to lay a little bit of the groundwork, but I want you to take it in whatever direction you feel most appropriate. But I'm really interested to hear how that, at what point in your life was that? Did that come into fruition, and how did you utilize that moving forward?

Keegan Caldwell: 3:17

Sure to start, and it also is kind of like the beginning of a lot of pain and misfortune, self-inflicted. That, I really think, informs a lot of what I do today and that I'm profoundly grateful for as well. So, you know, like, like anybody growing up, you know, I had a a fairly decent childhood. I have a very loving family. There was no shortage of love, right, we weren't. We're definitely, you know, we're a blue collar family through and through, but we, my folks.

Keegan Caldwell: 4:01

Today, you know, I was in New York City at the NASDAQ studio yesterday and my mom's, like you know, she just calls me crying because she was, like I remember, when you used to work the McDonald's drive-thru window, and to me it's even, you know, kind of surreal too, but it's also, you know, just a blessing and an amazing opportunity that I don't take for granted because of all the life experiences that I've had. Sure. So, yeah, I, you know, self-conscious, not comfortable in my own skin, sort of teenager, trying to find my place in the world, trying, you know, all of this and I think, some combination of that plus just generally not challenged, like at school, I was always, always like a very good student. And then I, you know, started, started smoking a little bit of weed here and there, and then this was before. It was legal everywhere in the world and so still an illegal activity at that point, which is just crazy to me. It's a whole other side thing anyways.

Keegan Caldwell: 5:16

I think I have no real position on the legality of marijuana or anything like that, but it's definitely for those of us that have lived in both worlds. It's definitely for those of us that have lived in both worlds. Um, it's uh, it's bizarre in some ways to be like, oh my gosh, I thought you had to look over your shoulder all the time and now it's just like do whatever you want. Um, and but that quickly progressed for me, right and so, uh, where you know. Then I started to, you know, drink a lot and then got into, got into psychedelics and other harder substances. By the time that I was supposed to be graduating high school, I was dependent on opiates, whatever form, either pain medication or stuff that I was buying on the street, sometimes heroin. It was a tough scenario, but really what it boiled down to, as far as my story is concerned, is that I wasn't, although my freshman and sophomore year I was a maybe B plus A minus student, something like that. I was barely even going to school anymore, something like that. I was barely even going to school anymore. I would barely even show up. I'd given up that part of my life and there was zero effort being set forth and I ended up not graduating high school. I didn't have college opportunities, I didn't have any ambition to want to go to do those things.

Keegan Caldwell: 6:46

And one day a good friend of mine just called me and said, hey, do you want to smoke a joint? And I said sure. And he came and picked me up and we bogged out his little Toyota Tercel and then he was like I have to go to, I have an appointment I have to go to. And I was like why isn't he telling me where it is that he has to go? Is this driving me nuts?

Keegan Caldwell: 7:09

And we like pull up to the recruit Marine Corps recruiting center and I was like oh, dude, I'm not going in there. And uh, and he goes in and I was like I'm sitting in the car and so I sit and wait in the car like five minutes or something like that. And then I was like whatever. And so I go in and we must've had like the best you know that salesman. Uh, that recruiter was one of the best salesmen I've ever met in my life, cause we were there for like four hours and by the time we left I went from like this is the last decision I'd ever make in my life, to America, let's go.

Keegan Caldwell: 7:40

I might argue you're, you were, uh, you were impaired, so maybe and so, anyways, I signed up for the service and you know that provided me with some structure in my life. That was much needed. You know, like I was like removed. There's a zero tolerance policy in the Marine Corps for, uh, you know, any drug use. Right, I mean you can drink, obviously, but uh, um, even that was like pretty limited cause you're so busy. You know you have like a lot of structure and you know every day is uh, this routine that doesn't allow you a lot of time to go engage in something. That would be a huge distraction from those things. And so I, you know, to keep this part kind of short, I guess that gave me some structure. That was useful.

Keegan Caldwell: 8:36

But you know, fast forward a few years when I get out of the service. As soon as I get out of the service, then, uh, it was, I had trouble like finding my place again. You know you go back from like having like a job where you're important and uh, you know I had several meritorious promotions while I was in the service and I had a great Marine Corps career while I was there. And then you come back and you're like, oh shoot, what the heck am I going to do? All of my buddies were getting done, had completed college at this point, for friends of mine that did go to college and I still found myself kind of this guy who didn't graduate high school and although I did complete school in the Marine Corps graduate high school, and although I did, I did complete school in the Marine Corps, but in the same position where I was just trying to find like my place and get my feet underneath me but I just turned right back to the same thing, right, and got got right back into drinking too much and using drugs and and unfortunately at that time it just progressed rap, you know.

Keegan Caldwell: 9:41

It got even worse, where I've gotten heaps of legal trouble. You know, was arrested several times for, you know, possession and, uh, you know, did several stints in jail as a result of of some of those arrests too. So there was like a three-year period, basically from 2003 until 2006, where I was arrested 13 different times and was was basically like a revolving door for me and I, uh, I was a mess, you know. I didn't have a lot of respect for my own life or for the lives of those around me. I think, like many people that are caught in the depths of addiction, like we think that what we're doing is not affecting others. And, uh, um, and I, I certainly thought that, and only after, you know, several years of of being sober, that uh, uh, I think I was able to to be like, oh, wow, Like a lot of my behavior was having a terrible effect on those around me, Right, and I even experienced that in my own life today, with family members that struggle with drinking and substance abuse, and you want the best for them, but there's, you know, there's that they're very loving and always supportive and we weren't a family of means, but you know, I had betrayed all of their trust, you know, in this period of time Interestingly though, I also started like my first business during this time period and was just working as like a general contractor, and or as a subcontractor rather, for a large home builder, like building decks and screened in porches, and that was great.

Keegan Caldwell: 11:33

It's what felt it, that felt natural to me, you know. So, like that was kind of like my first little sprinkling of like oh man, I've got like this little bit of hustle, Cause I was, you know, I was like framing houses and making like a good wage, you know, per hour doing that, but I had. Basically, I had grown up like on job sites also and I was like, well gosh, I feel like I can make a lot more money if I just did this for myself. And it was like all I need is like a pickup truck and a handful of tools and off I go Right. And so, uh, I remember, like printing up some business cards, you know, going to like a Kinko's and printing up like some you know handyman sort of business cards or whatever, and like I would, I was working a job for you know a framer, like getting paid by the hour, and I'd get done with that day working in the sun.

Keegan Caldwell: 12:21

And then, um, go do like door to door, like handing out my business card, saying, you know, hey, have you ever need somebody?

Keegan Caldwell: 12:30

You know, let me know. And I'd just go drive to like the nicest neighborhood, wherever it was, that I that I was living at the time, which was, uh, in the Washington DC area, and uh, um, eventually people started to call and I got enough work where I could quit the job where I was working, and probably also, unfortunately, though, that gave me some flexibility with my schedule and more money. That allowed my addiction to progress. Right when I wasn't needing to scrape by as much and things you know continued to get worse for me. Right when, even if I had went to jail for a few days or something like that, at that point it wasn't I had to lose my job or anything like that. Right, I still had the business and nothing was that time sensitive as like a subcontractor for most of those jobs that I was working on, so the repercussions were not big for doing that. So, uh, this this period of time uh in my life like that, like 03 to 06, was just, uh, well, super painful that was so what you this.

Marcus Arredondo: 13:38

How old were you at this point? I'm how old were you during the marine corps? You, it sounds like 18 to 21 ish.

Keegan Caldwell: 13:45

Yeah, like, yeah, yeah, 18 to 22, and then got out and then, um, so now, uh, yeah, I'm rough, you know 23, like, basically like 22 to 26, you know, yeah, yeah, and uh, um, and it was.

Keegan Caldwell: 14:06

You know, I had no, even though I had my GI Bill, I had like no intention of like using it to go to school or anything like that. I hadn't even thought about it, right, I actually I had like a grandmother that had encouraged me. She was like listen, like you know, she knew that I was getting in a lot of legal trouble and was just struggling with life in general, and I come from a huge family like this. I grew up across the street from my grandparents. They had nine kids. I've got, I don't know, I think, like 52 first cousins or something like that. You know, like we have, we have a really big family, and so, you know, when you have a family that big you have, you tend to learn a lot about compassion for others, at least hopefully, um, cause you have people from all walks of life, right, you got people that have. You got the haves, you got the have nots. You got the people that are, uh, you know, have, you know, deep faith in their lives. You have people that don't, or practice different faiths, maybe even, um, you got people that are, you know, blue collar people. You guys white. You know you got it all right. And when you what we all get together for the holidays and spend time together and, um, I felt like I got a lot of confidence, learning how to connect with many different types of people. Uh, just like like family events, growing up, right Cause you're uh thrust into these different social dynamics and but you didn't think it was weird. That was just how, uh, how you, how you grew up, and that was what was normal and so you get, you know, you get used to, uh, used to doing that. That's what the norm was for you as a kid. Yeah, so it was uh, all this time was like uh, just just really tough and I couldn't get it to get, couldn't get it together. It was was, you know, substance dependent.

Keegan Caldwell: 15:50

And in the December of 2005, I it was like cold, I was in Michigan and one night I was just like you know I've just had enough of this and I like went to the hospital. I mean I was very sick. You know, like I was probably 60, 70 pounds less than what I weigh now and I'm not in great shape but I'm in decent shape. But you know I was, you know, skin and bones, yeah, and very unhealthy, and you know, I mean maybe I'd eat once every couple of days or something like that, you know, and it would be like some little Debbie's or you know, a couple of oatmeal cream pies you'd take from a gas station or something like that, or like, uh, maybe a hot dog from a Speedway or something.

Keegan Caldwell: 16:45

I was living the high life and uh, uh, so and so, anyways, that was like a big turning point for me. So, like I and it was fleeting too, I don't, you know, I know this whole, I know the podcast isn't a recovery focused podcast, but I think, for a lot of people that are just entering sobriety too, that, like you know, things will get painful enough for you that you're like, oh man, I should really change some things. But then, like two weeks later, after you kind of dry yourself out and do a little bit of spin dry, you're like I'm probably good now. Right.

Keegan Caldwell: 17:16

And so even all the terrible stuff that happened, you know.

Marcus Arredondo: 17:21

I'm glad that you can laugh at this, because I do think it's. I'm sure there was some pain involved here, but I do. I don't want this to. I don't want us to necessarily ruminate on on this particular part of your life, although I think there's a lot of great things here. Sure, um, I what, but what? I am curious about those who go through it, and I've never I don't think I've ever been a problem, but I have.

Marcus Arredondo: 17:42

Between drinking and other stuff, I have increasingly become aware of its involvement in my life and there are times where my productivity might go down, certainly earlier in my life, where when the end of the day might come by and it's like I really haven't done jack shit and I don't feel good about that and that's what it compounds. I mentioned that because I'm curious what you see from my perspective. What I've witnessed from those who've come out of recovery successfully are a number of things. One is sort of hitting rock bottom. It's sort of losing, acknowledging that you've lost touch with yourself in some way or not ever, maybe, had a knowledge of who that self was. But what I'm most interested in is, at that moment, for those people who have met that nadir, what do they do? What do they find? What is that element, that is the motivation, the inspiration that says, okay, I got to get my shit together. I am now ready to do this work, because I think that same thing is also what may have likely been what's made you successful in your entrepreneurial endeavors. And in some ways I sort of think I'm offering this because I could be wrong, but my sort of view from this it actually seems like you know drugs in many ways.

Marcus Arredondo: 19:10

I know that there are chemical components to people's brains that are certainly that, that contribute to this, but there's also I have from those who have overcome substance abuse, who have become productive members of society have an itch. They have something that they are hungry for, something in life. They are looking to be productive, they are looking to do different things, but if they're not actively engaged with that, it gets supplanted with these other fillers that just completely change your trajectory. And I guess in your take is there any truth to that. What have you found most specifically? I'd welcome any input that you have to this, but I'm really interested in what ultimately pulled you out right. I mean like going to the Marine Corps with your buddy who was stoned and said, hey, I'm going to go sign up and you sitting in the car for 15 minutes and saying I'm going to go sign up. Maybe that's a stroke of inspiration from the Lord above or something.

Keegan Caldwell: 20:10

I don't know.

Marcus Arredondo: 20:12

But I'm more interested in it. Like you know, now it starts to get a little bit real. When you get out you struggle to find your footing. A lot of people who have been in the military struggle with that same thing. But then you get into subcontracting, you start to find purpose, you start to find money and then it rears its head again because now it's not just now.

Keegan Caldwell: 20:30

the availability, yeah exactly, and, you know, some of it was like in waves. I mean, that's what's so tricky. You know, I always tell people like the hardest thing about diagnosing, you know, alcoholism or addiction is that you have to diagnose it yourself. You don't just go to the doctor and they're like you're an addict or you're an alcoholic. You know, usually that's not the case. Um, it's something that you have to diagnose yourself, and it's the last thing that you want to diagnose yourself with. Right, you're like right, I don't want to have that. I'm really enjoying myself doing this. Right, even if you're not enjoying yourself, you don't want to have to have that affliction and uh, so um, have that affliction and uh, so um.

Keegan Caldwell: 21:12

Yes, it was a, it was a super tough time, and I do think, though, that those uh like at that point, when I, you know, made a decision that I wanted to turn things around, like I said, it was fleeting a little bit, but I was just broke down, you know. You know, whatever that rock bottom moment is, which it's different for everybody For me, it was this cold, wintry Michigan night where I didn't have any place to go. I'm near the hospital, and I decided to go in and be like listen.

Marcus Arredondo: 21:39

I need some help, you know when you didn't have a place to go. You mean homelessness.

Keegan Caldwell: 21:43

Yeah, I mean, you know, sometimes I'd be staying in hotels. Sometimes I'd be, uh, um, you know, sometimes I'd be staying in hotels, sometimes I'd be, uh, um, you know, crashing on somebody's couch or something like that. But it, you know it was, it was, you know, a mix of those things. No-transcript alienated a lot of my family, and so I was really just focused, like on trying to take care of myself and trying to just make it through each day, Cause some days you were like, oh yeah, I need, I need to get out of this. I don't want to go back out, uh, um, into doing, you know, in relapse, but, uh, you know, that voice inside your head is really loud too. And so, uh, I just focused on taking care of myself and doing my recovery.

Keegan Caldwell: 23:09

I've been involved with 12 step recovery for about two, two decades and, um, it's uh, that's been a great thing for me. I know there's people that do things different ways, but for me that is uh, I was just doing another podcast with someone else and I was saying like that's my secret weapon. You know, like all of my personal um, introspection and cause I'm not focused on, um, you know, it's always my goal to not pick up today, but most of the time I'm just, you know, I've developed some great tools for identifying you know who who it is that I am, great tools for identifying you know who who it is that I am. What am I contributing to the world? What's my role in certain, in certain things? And just getting out of this mindset that the world is happening to us and, uh, you know, and that you know, no one's really to blame for any of this that there's some things that I can do.

Keegan Caldwell: 24:01

And even if I'm in a really tough spot, which I was at this particular point in beginning of 2006, very, you know, tough, you know negative amounts of money, uh, no, education. Um, I still had my GI bill, which was great, and some people encouraged me to go to school, and so I decided to take advantage of that and, uh, I applied to a bunch of different um universities and, amazingly, I got in um everywhere I applied. I'm still, to this day, a little bit confused about that, cause I was such a terrible student, but I think it's just because maybe I had the GI bill and they're like he can pay, let's let him in, and so, uh, that worked out and you're not taking any financial aid, you know. And so maybe that, you know, I don't know, maybe those are factors, maybe those are factors, I have no idea, but it's less important for this. Uh and um, and then even that was very uncomfortable, right, I hadn't been to school. Now I'm 26 years old, I hadn't really even been and been to school in like 10 years, basically, right. And then, uh, by the end of high school, I just wasn't even going and was thrust into this. You know, these classrooms with bright eyed, you know fresh face looking, uh, 17 and 18 year old people and I felt like an alien in there and was, you know, very uncomfortable.

Keegan Caldwell: 25:23

But I, I stuck with what I was, what worked for me, which was just, you know, getting up early, going through my little routine, you know, creating a routine for myself, just like I had in Marine Corps, where I'd get up, you know, do basic stuff and get my day started and get to my 12 step meetings and handle whatever. You know, between school I worked basically fulltime during my undergrad also, but just for the university, catering. Then I did some side jobs doing things like that here and there. I had several criminal convictions also. It was really hard to get jobs nearly impossible At that time. I would do a decent amount of work like under the table, not paid cash.

Keegan Caldwell: 26:13

So when I did, once I got done with like my first year of school, I realized that I wanted to. I figured I would be a dentist. My grandfather was a dentist and he was like one of the most he was you know where I grew up. I thought he was a pretty successful guy. So that's what made sense to me and so I studied to do that, which is why I have my biomedical science degree for my undergrad.

Keegan Caldwell: 26:43

And but in the process of doing that, because I had these criminal convictions, what I realized was that even if I was to get into dental school and go to dental school, it wouldn't be until after that and I would apply to get licensure, that I'd really find out I'd be able to get a license to do that and, more importantly, if I'd be able to get a DEA license to be able to write prescriptions. So I mean, and I even went as far as like reaching out to the dental board of you know, examiners or whatever and asking them like hey, you know, like is this something that's going to be possible? This is what the scoop is. I've been sober this long, you know. They're like, well, we can't guarantee anything. It's like, well, I don't have $300,000 I can do on a maybe, right, you know, maybe, and especially years of my life. You go to dental school for, you know, three or four years, you know, and then uh, and then just to find out that you couldn't even have that as a career path.

Keegan Caldwell: 27:32

So I ended up, uh, I also thought it would be cool to go to law school. Uh, but that was the same thing. It's like you go to law school, you're done, you apply, you take the bar exam, and it's not even until after you had passed the bar exam that they examine your character, fitness, and so you know, that's again several year path, just to find out that, you know, could be, you make it, could be you don't. And so I didn't want to rest my hopes and dreams on those sorts of maybes and I thought, well, all right, well, I knew that if I went and got a PhD, I could put some more letters after my name. By doing that. Also, I put myself.

Keegan Caldwell: 28:12

You know, by the time I finished my undergrad and I did my PhD, I'd at least have eight years in between me and this really tough sort of existence that I was living as long as I could continue to stay sober. So there was a guy that I one of my professors that was like you know, listen, you can go get a phd and that's basically free. You teach, uh, you know chemistry, labs or whatever, and you can do that and you have a gift for doing this. You've been working in my lab for a couple years. Why don't you go do that? You know he. He knew my situation.

Keegan Caldwell: 28:42

I kept most things pretty close to the vest at that point, like I certainly wasn't going to talk about it openly like I am now. Yeah, and that was just because of the stigma that surrounds addiction, and I was just so desperate to dig myself out of this massive hole that I found myself in, right, and to create some new opportunities for myself, and I didn't want to stifle any of those opportunities by, of course, you know, talking too much about what my past was like and uh. And then you know, and I'd gotten a lot of advice too, from very smart people that were like oh, you could never be a lawyer, you could never be a doctor, you know, to that was why I would go to, like the, the actual people that made the decisions, because I wanted, I wanted to know directly from them and it was a lot of work for me to figure those things out who those people were. I can get in contact with them, um and to have conversations with those folks. So, anyways, I did all that.

Keegan Caldwell: 29:37

I did the PhD. That's why I got the PhD, um was cause I wanted to avoid any uncertainty with what I'd be able to do. At least this way I could. Worst case scenario, I could have some sort of academic job teaching, uh, uh, physics or chemistry or something like that, and uh.

Marcus Arredondo: 29:55

I and at this point, have you had any relapse?

Keegan Caldwell: 29:58

No, no. And so, like my third, my third year, um, my third year of, uh, my PhD program, I decided to do this internship at the patent office. And so I did, like an internship at the USPTO, the third year of my PhD, I had a PhD advisor that was nice enough to let me do that, because I did get paid by the school, I didn't have to pay for it. And so, um, I did, and I worked in like a special unit at the patent office where they would look at these high-tech companies that were disputing over patents and it would be like, you know, google and Apple and Facebook, and I thought this is pretty cool, you know, and I was like I think I want to get into this. But I was like I don't want to work here at the patent office. I wanted to do it in private practice because those guys seem like they're doing a little bit better and I've worked really hard to get where I'm at now. I'd like to have at least a couple bucks to rub together and at the time I still had nothing right. I mean, I was renting a room in this lady's basement in Washington DC while I went to grad school and I mean that's a common kind of a grad school story, but I, you know, I was an older student and was, uh, was hoping that there'd be some sort of silver lining at some point. Uh, but nothing was seeming to appear.

Keegan Caldwell: 31:17

Because even by the time that I got done with my PhD and I'm applying for jobs everywhere, I mean, I think I applied for, you know, well over 200, if not 250 sort of jobs. It was so challenging to get it, with previous criminal convictions, to to be able to get a job. You know, and interestingly, or ironically, one of the one of the only offers that I had was from the defense intelligence agency. Just, I think, because of, like my prior service and because of you know, they have a process for disclosure of all those things, and so you go through and you tell them all the stuff and they know it, they have access to all your files through government systems and things like that. Anyways, and as long as you're just, you know, my experience has been, as long as I'm being honest about what my past is, that it's generally viewed favorably by most people. Some people you can't get them over the hump, and maybe they probably got their own story of getting burned by someone that treated them like crap right.

Marcus Arredondo: 32:18

Well, I would like to take a minute here, because there are a couple of things that you've mentioned that I want to peel on. But where you left was that you got an interview with the defense agency. Oh, yeah, yeah, yeah, but before you dive into that, you got an interview with the defense agency. Oh, yeah, yeah, yeah, but before you dive into that, you mentioned some skills that you've learned to utilize to help identify more of who you are, and as you're talking about this, the word identity keeps coming up in my mind, which is that it's not just who you are, but who you're not.

Marcus Arredondo: 32:44

In many ways, and I think a lot of people think of identity as something you add on to, you put more components on, but in a lot of ways, it seems like identity is actually removing parts of you that are not yourself, and what might be scary about that is, I think all growth requires some form of death, and that death is part of your former self in some ways, and it's the people that you used to hang out with with, or the groups that associated with something that you're no longer trying to associate with, and that's sort of a hard thing, because if every Friday, saturday night, you're spending time with these people. You're no longer doing that, so you have to find something else to fill your time. So I guess I'm just curious. I'm really fascinated by what skills you've developed that help you. Obviously, the 12-step program is something that you talk about the discipline you integrated from the Marine Corps of getting up early and sort of having a routine. What are those things?

Keegan Caldwell: 33:38

Yeah, I think super disciplined about finding the goals that I want to pursue and sticking to just those things. Like, even when I was in my PhD program, like I, I stopped watching TV um then, cause I was like, well, this is just a waste of time, and I felt like I had years to make up for, and I had uh like a belly full of ambition of what I wanted to do. And I was doing my PhD program and I'm getting a PhD in you know chemistry, by the way, and I was doing my PhD program and I'm getting a PhD in you know chemistry, by the way, and I did not have an undergraduate degree in chemistry and so, like the mathematics and the, the people in my PhD PhD program were far more skilled than I was and I had to put in a lot of work and effort just to get up the learning curve. Sure, but uh, I also think that, uh, having some of those experiences, you become resilient, you don't beat yourself up too much and you stop kind of listening to the peanut gallery. You know, a lot of that applies in my entrepreneurial life today as well.

Keegan Caldwell: 34:43

I used to read a lot of books. This is probably super unpopular, but it's a I know I heard like hard I. It's a very rare day that I would read a book now. Um, maybe if I was reading something that was just for pleasure, or something like that but I don't know read anything on like business or anything like that, and uh, um, but it's mainly just because I uh.

Keegan Caldwell: 35:02

I'd rather be doing yeah, I need to be doing it and most of what I've learned is through my own experience. Yeah, so that my experiences have informed me to make like objective decisions about figuring out what those goals are. I always like the. I think it's like the pilot story with Warren Buffett, where he's like, oh man, how could I be as successful as you, or whatever. And he says, well, write down the 25 things you want to accomplish in your life. And then he's like, okay, pick five of them. And he says, or write down the 25 things you want to accomplish in your life. And then he's like, okay, pick five of them. And then he's like you see, the rest of those 20 things, avoid those, like the plague, you know.

Keegan Caldwell: 35:34

And I like that made sense to me you know, and I was like, oh, man, cause it's like a sacrifice, you know. But you're like, oh, okay, but this is what I have to do. I like, yeah, wrote down my five things and I'm like, if it's not any of these things, then I'm not gonna do it, you know, and like an example that is in, I don't want to get too ahead of myself. I know we're going to be limited on time eventually and give myself, you know, some time to talk about, uh, a little bit about with the firm.

Keegan Caldwell: 36:02

Today, a lot of that is discipline, and resilience continues to play a significant role in what it is that I do, and objectivity and not making emotional decisions allow myself to zoom out and to stay focused on whatever the goals are and, in things that are not my goal, if it doesn't look like success, then to not do it. And uh, um, you know like sometimes people will be like, oh, why don't you do this, or why don't you do this particular program, or why don't you do this? And I'll be like, well, cause I don't know anyone there, that's what I want to be. And um, uh, and so I stay disciplined about that stuff, recognizing that I only have so much time, and I'm disciplined about my time as well. There's only so much time that we get and I try to use it very wisely, and between having a very quickly growing law firm today and a family, it doesn't leave you with much.

Marcus Arredondo: 37:16

I hear you, so let's jump into that. So you were at the patent office. I am curious how you went from the patent office to starting this law firm, which was originated as an IP law firm. It has since broadened Is that correct.

Keegan Caldwell: 37:27

That's right, so I am curious.

Marcus Arredondo: 37:29

Talk us through just from the patent office to creating the IP firm. I think that's super interesting, but I want to leave a couple of minutes to ask some dad questions and talk about your help with incarcerated entrepreneurs. So let's start there, from the patent law.

Keegan Caldwell: 37:48

Well, I got done with school, I was able to get a job at a law firm and I, uh, in patent law you can get these jobs where you're not, uh, you haven't taken any bar exams, but, uh, you are kind of working as like a technical specialist, because it's so, everything in patent law is very technical and so, you know, I was able to get a job like that because I have my PhD.

Keegan Caldwell: 38:11

Um, I worked that job for, uh, you know, two or three years.

Keegan Caldwell: 38:21

Um, I also learned when I had that job that I knew that I could take the patent bar without going to law school, and so I did that and I took the patent bar past that, and that's like a federal bar that allows you to practice in any state, and I figured that as long as I could pass that, then I could probably pass a state bar, because they still do the character fitness for the federal bar and if they let you do it at a federal level, then they must let you do it at a state level, was my logic.

Keegan Caldwell: 38:44

And then it turns out like in California and Vermont you can also take the state bar without going to law school, and so they have different requirements depending on which state you're going to do it. But in short, basically you're like in a mentor, mentee sort of a program. Yeah exactly, you find some other attorney that's willing to work with you for a few years and to sign off on that. You're studying what you should be studying and then at the end of that you can go take the bar exam.

Keegan Caldwell: 39:19

And that was what I did. Somewhere in, though though I so I had taken the patent bar, and then I started my law firm after that with the idea that, uh, I could create something that was more, uh, flat fee based, and that, you know, I saw some law firms move like at a glacial pace. They're not particularly innovative. They have these big, arduous partnership structures where it's challenging for them to make decisions in any sort of nimble fashion, because there's too many decision makers wanted to have something that was a bit faster growing and to incorporate new technologies as well. So I started something like in a one room co-working space office on MIT's campus about 10 years ago. That was financially ruining me, and like one room, windowless office. It was like the cheapest co-working space office that they had, and I was like this is. It was like a huge financial risk. It was still like $1,750 a month for that whole one room, and I was like this is crazy. But I knew that I was like on MIT's campus and I was doing patent law at the time and I thought, man, if I can just get the scraps of what's going on here, I might do okay. And we built like a very, we incorporated some technology and we built like a very you know, we incorporated some technology, we developed, like this AI tool that really changed our trajectory a lot in the area of patent law, and we went from being the small kind of one man shop to having offices around the globe today, adding a corporate practice.

Keegan Caldwell: 40:56

Like I said, we work with a lot of startups, from solo entrepreneurs that are just getting started to global corporate companies, some of the largest global corporate companies in the world. We started with just our office here in Boston. I'm actually talking to you today from my office in Boston at the top of the Hancock Tower. I have an office in Santa Monica overlook Santa Monica Pier in Malibu. That's my favorite office. I wish I was there. And then we have an office in Mayfair in London, and we're opening an office officially in Tokyo May 1st and bringing out a team of people there as well, so that we can work across multiple continents and be able to provide we're the only firm that exists on the planet that's our size like this mid-sized law firm that has that global reach, which means we can beat people up on price point and stuff like that.

Keegan Caldwell: 41:49

But anyways, the goal, though, in asking what are those things that I use today from those experiences that I've had in the past. I use today from those experiences that I've had in the past Uh, there, uh, you, you learn how to make quick decisions as well. Right, yeah, you learn. Uh, I don't you know, get in the mud and try to figure out all the little nits of everything. Um, I generally tell people you don't want me to be your lawyer, you want someone that works here to be your lawyer. I'm really good at high level strategic thinking. I'm good at helping businesses position to make money, but getting into the legal weeds of things is not exactly what is my particular specialty. But we have plenty of people here that are much smarter than me, and that's another thing you know. Like making sure that you're hiring people that are smarter than yourself. You never want to be the smartest guy in the room, as they say here.

Marcus Arredondo: 42:44

For sure. Well, let me ask a quick question, not to discredit the corporate law, but I think the IP law is something that I think has a lot of tailwinds right now, given where we are in technology. And I'm just curious if you could just highlight what most lay person, lay people don't know about IP law. What do you think they misinterpret about what it is?

Keegan Caldwell: 43:11

The things that I, when I'm having conversations with my like prospective clients and we're just getting on the phone, I'd say the biggest misconception is them thinking that whatever it is that they've done is not innovative Because it doesn't feel particularly innovative. Maybe they've been doing something for 20 years, they're an accountant that's been, or an engineer that's been working on the same sort of thing for 20 years, and when you're doing something for that long, nothing that you're doing seems that innovative because you know, oh, other people are working on something like this, or other people like this are working on something like this. But really an invention is, for something that would become a patent, the combination of two known elements, right? Unless, of course, you're coming up with something new on the periodic table of elements which is quite rare, uh. And so, uh, no, one's doing chemistry joke. Yeah, it's, it's. Yeah, it's kind of a joke and kind of, you know, also like a good frame of reference. So that's the only thing that would not be a combination of known elements, right? Yeah, everything else is. And so I love this example.

Keegan Caldwell: 44:21

I worked with a car wash over the last few years to help them build a patent portfolio. We don't think of car washes as being particularly innovative, but we worked with them to develop a patent portfolio of like 40 to 60 patents on things that they were working on and just new systems that they had made over the years, because most car washes have been using the same sort of systems for the last 75 years and when there's a breakdown, it's like these are mom and pop shops that until you can get the new part, it's going to be down for two weeks or something like that and you need to make money. So anyways, by way of example, like if a car wash can get uh, 60 different patents on new sorts of technology just by combining known things like um payment processing systems and license recognition and, uh, you know, you sandwiching those things together in in unique, new, not obvious ways, uh, then many other people, you can do something too, and I wrote an article in um entrepreneur magazine last fall. It's called like patent the boring stuff. I think it was the title of it or something something to that effect. That's because many of the things that have the most value in the patent world are not the things that are these bleeding edge innovations. They're not the rockets that take up from the launch pad and land back in the exact same location, because no one else will ever do that.

Keegan Caldwell: 45:47

That sort of a patent on something like that. The likelihood that that's going to be high value is basically very, very low. But where people maybe you have an HR company and you build some sort of you know software tools over the years that help that process flow, probably lots of people will need to use something like that Right, and so it doesn't seem particularly innovative to you, but most likely it is and it's worth doing that. You know we. I know we have mutual friends that talk about this being your greatest asset is your IP, but it depends what you're going to do with it. You know Right, and does it fit in your business? Yeah.

Marcus Arredondo: 46:24

So I'm going to ask one last question before we start to wrap it up. I know that you counsel incarcerated entrepreneurs who are coming out. One just stood out in my research, talking about Thomas Alston. Oh yeah, you know, what I saw was someone who was an entrepreneur, caldwell says, and were really good at helping entrepreneurs. He decided to assist Alston through the long, expensive process of obtaining a patent, monetizing it, potentially worth hundreds of thousands or even millions of dollars in billable hours, entirely for free.

Marcus Arredondo: 46:59

So I just was wondering if you could speak to mentorship and maybe hit with two birds with one stone how you approach some of these skill sets. As a dad with your own children, you know what are the lessons you take away. How do you communicate with them about resilience, about recovering from setbacks earlier in your life? You've done a remarkable amount of work in less than 20 years. I kept thinking about the phrase most people overestimate what they can do in one year, but severely underestimate what they can do in five. I think that's a testament. You're a testament to that phrase. So I'm just curious the role of mentorship and leadership as it relates to the work you're doing and as a dad.

Keegan Caldwell: 47:36

Yeah, we've done some great pro bono work. What the work you're doing, and, as a dad, yeah, we've done some great pro bono work. I think the easiest way for me to summarize that, though, is at some point in my own trajectory, I began to do some volunteer work and to give back to the community, mostly to help me get into grad school, but what I realized over time was that when I stopped doing that, it didn't feel right, and so that, um, that's always been, you know, doing some form of service outside of my work, I believe, is very important for me to do, uh, and it's core to what I want to accomplish each day, anyways, is just to be of service to others, and you know the ways that I bring this, you know, as a, as a, as a dad, oh, you know, honestly, it's tough, tough. You know, like my life's very, very different from like when I was growing up, was very different from the lives of my children. Today they have, you know what I would consider to be pretty cushy, I mean, I feel like that's what all dads say, but, like you know, it's like. What do we do, though, to make them be decent human being that respects the respect, uh, other folks and the value of the dollar and have some good core values.

Keegan Caldwell: 48:42

Yeah, um, for me, that's helping my children. You know I work with them to set goals, uh, I mean I have like a 10 and a five year old and we do like vision, do vision boards with them. I have like a monthly family meeting that we do where we are. It's so awesome. I have like a monthly family meeting that we do where we keep track of what it is that we accomplished the last month. Um, and this teaches them accountability, uh, and what it is that the goals that we're going to set for the next month, um, if you can't measure it, then how will you do it and how will you know you accomplished it Right? And so that's like the best way that I I feel like that I can teach them some skills that uh will have some real world application. You know it, it is.

Keegan Caldwell: 49:29

You know, I'm sure you know being a parent is one of the hardest things in the world and, um, we love, we love them so much and we just want them to have it easy. But the other thing that I know is that most of everything that I do today didn't come from things that were easy, and so I want to. I'm like it's like, how can I carefully push them to do some things that will create some discomfort for them? But not, you know, hardships, you know. Like, you know, it's kind of like towing that line, you know.

Keegan Caldwell: 50:01

So that's, uh, it's so important, and I think the the big one there, though, is that it just deepens our relationship, right, like we really build trust together, uh, with the children, by doing those things together, right, because we're not just doing it we, we do it too, and, um, that allows us to to all, like everyone as a family, to be like okay, cool, we're all on this together. This is what we do to be successful. We know we've done some, we know we're a little bit different than some families, and but this is how we do it. We do it together and we're we do it as a team, yeah, that's a great way to end.

Marcus Arredondo: 50:36

I want to open it up to you. Any closing thoughts or things you think I might've missed.

Keegan Caldwell: 50:43

I don't know. The only thing that I would say in closing that I'm just, I'm very grateful to be here today, and the number one principle in my own life is gratitude. Right, like, even on the worst day, it's a pretty good day, man. So you know, count my blessings every day.

Marcus Arredondo: 51:00

Well, the feeling is mutual here. Thank you so much for being on, I appreciate it.

Keegan Caldwell: 51:05

Marcus, thank you brother.

Marcus Arredondo: 51:09

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