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Certified Financial Planner™ Greg Blake joins Jerry to talk about serving clients who often feel overlooked, how to get the most from a financial advisor, and why empathy is a financial superpower. Greg also shares his own story—serious health challenges, divorce, and a looming court date—and what it’s like to feel invisible in systems that should help. A raw, hopeful conversation about money, identity, and respect.
Content note / disclaimer
This episode includes discussion of serious health issues and legal stress. Nothing here is legal, tax, or medical advice. For personal guidance, consult licensed professionals.
💔 Note: Greg M. Blake passed away in 2024 after ongoing health challenges. This episode remains up as a tribute to his honesty and insight. May he be remembered with compassion and respect.
In this deeply personal episode, Jerry sits down with longtime friend and Certified Financial Planner™ Greg Blake to discuss serving diverse clients—including LGBTQ+ folks, military families, and seniors—and why trust and full transparency matter in financial planning. Greg also opens up about his own hardships: severe health issues, divorce, child-support court battles, and what it feels like to be judged and unheard. It’s a candid conversation about dignity, empathy, and getting the right help when life turns upside down.
Key takeaways
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Advice works best when you’re fully honest. The more context you share (income, debts, goals, constraints), the better a planner can tailor a plan.
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Underserved doesn’t mean undeserving. Military, LGBTQ+, seniors, and anyone who’s felt judged still deserve unbiased, high-quality guidance.
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Life events reshape money plans. Divorce, disability, and job changes demand updates to cash flow, insurance, taxes, retirement, and estate docs.
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Respect is a prerequisite. Choose advisors who create a judgment-free space; if you don’t feel seen, find someone who gets you.
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Empathy goes both ways. Professionals face struggles too; bridging that gap makes planning more human—and more effective.
This episode is in his memory.
SPEAKER_01:
With your host, Jerry Williams. The podcast that's all about money from a gay perspective. Hey, everybody. And this is Jerry, and this is a brand new episode that we're going to record here today for you. And I've got a special guest that's going to be joining us today. His name is Greg Blake, and Greg is a Certified Financial Planner™, and he's been doing this for quite some time. And I've known Greg for a long time as well. He's a fantastic financial advisor. And I've always learned a lot working with him and listening to him. So I think he's going to have some terrific insight for us. And I'm really excited to have him with us today. Unfortunately, due to the coronavirus, I don't have Greg in the studio, so I can't look at his handsome face. But I do have him on the phone, and we're going to go ahead and bring Greg on. Hey, Greg.
SPEAKER_00:
Hey, thanks, Jerry.
SPEAKER_01:
It's
SPEAKER_00:
so good to talk to you again.
SPEAKER_01:
Absolutely. I'm so glad to have you with us. And since this is still early on in this podcast, who knows what can happen during this podcast. I'm really excited, like I said, to have you. And I think there's going to be a lot of questions that you're going to help answer for a lot of people. And really to kick things off, like I said, you're a certified financial planner and you've been doing this for a long time. Tell me a little bit about the range of people that you've helped during the time that you've been an advisor.
SPEAKER_00:
No, sure. That's a great question. So I... you know, since I've been in the business, I've been doing this for about 20 years. You and I met back in 2008, I want to say. So it's been a dozen years that we've, we've been together. You know, I help, you know, I served in the military, so I really enjoy helping military folks. I enjoy helping elderly folks because quite frankly, they seem to get taken advantage of a lot. And then, um, I've worked with a range of folks. There's a number of clients that I've worked with. I'm not going to get the acronym wrong. I'm a straight man, but I have complete sympathy because I have family members. They're part of this, the LBGT, help me out. Yeah. Yeah. Right. It
SPEAKER_01:
changes all the time. Yeah. The LGBTQ plus, that's where it is today, but you know, yeah, that could change.
SPEAKER_00:
Yeah. So there's a plus now on the end of it. All right. So the point being is I, I've worked with a lot of folks from all walks of life, but I do have an affinity for the military, for the people, less, given the opportunity to work with somebody. And I think that part of society is, is they don't, you know, you got underserved. Yes. Thank you. You know, I'm, I'm struggling here. I'm a professional. I'm supposed to speak and sell, you know,
SPEAKER_01:
you're doing
SPEAKER_00:
good. I know it's a little, I know exactly what to say, but the point is that underserved. Yes. Underserved. You know, so I just, because I am going through my own, issues right now you know I'm very sick from a health standpoint and I feel like I'm underserved I feel like the legal system is not doing justice for me and I'm being cast out I'm 50 years old and I feel like I'm being cast out to die and anyone who feels that age whether you're 20 or whether you're 50 or whether you're 70 is it's wrong it's just there's something fundamentally wrong about it so I really appreciate what you're doing just to have a voice and talk and support the issues.
SPEAKER_01:
Well, I think a lot of people feel, like I said, underserved, and it could be for a wide variety of reasons. They feel that they don't identify with the people that they think that they would ordinarily speak to. Like, you know, if the financial advice they typically hear on the radio doesn't really resonate them because it's either highly Christian or it feels so judgmental or, again, if it's somebody that... they just feel like it's going to put them down versus help them, then certainly they're going to turn away from that advice. And that's what this podcast is really all about. It's saying, hey, you can be however you want to be. You can identify however you want to be. And you can have your issues dealt with from a professional. I have, like you said, we've been doing this for 20 years. I have a master's degree in financial planning. And all that being said, that's not going to help anybody, all the credentials of the world. If you really feel like this person doesn't have your best interests at heart. And just like you said, if it's a military or elderly people or anybody from whatever stripe of life, there are financial advisors out there to help them. And just like you said as well, we all have our individual struggles, you know, health and otherwise. And that's okay. Cause if you're struggling, let's say as a transgendered person and you're just figuring that out or you haven't yet come out of the closet to anybody yet, well, Those are very personal issues, and those have to be dealt with. Just like your financial well-being, that can't be totally ignored either. But all of it works in concert together.
SPEAKER_00:
Well, you know what, Jerry? Here's a funny story. Well, it's funny to me, but when we first met back in 2008, we were both working at, well, are we allowed to say the company name, USA? I mean, whatever is what it is. I really respected you as an advisor. And yes, I was this guy who's relatively recently coming out of the military and all that stuff. But it wasn't until you left USAA that somebody said, you know, Jerry's gay, right? I'm like, what? It just didn't register because I didn't treat you any differently than I would anybody else. But I'm telling you, and I'm not exaggerating about this, October, 15 months ago, or whatever it was, when I just surprisingly ran into you and Dalton at the Whiskey Festival. Yeah, the distillery, right. That just warmed my, I mean, I just reached out and grabbed you and hugged you. Yeah, it was so good to see you. That just warmed my heart. That was an incredible moment. And even though, you know, oh yeah, there's this military guy and there's this, you know, but that never bothered me. It has never bothered me.
SPEAKER_01:
Yeah, and I don't think it really
SPEAKER_00:
should bother anybody. Have I had experiences? Have I had experiences in the other side of the field? Yes. And I'm not going to call it out on air, but you were well aware of it. But the point is that it doesn't change the fact that you deserve the respect. You deserve the confidence and the support to be able to live the close as normal life as everyone else has been afforded in this country.
SPEAKER_01:
And
SPEAKER_00:
the fact that you're different doesn't make it wrong. No. And I, and I, that, that kills me. And I hate that. So,
SPEAKER_01:
and I think when you are, you know, as a financial advisor, I know when I've helped people to me, when it, when I've helped them the most is when I get the most from them, meaning they are able to tell me, a lot about their circumstances and about the situation that they find themselves in. And that's helpful to me because I can always tailor then my advice based on, yes, these are some good, solid, you know, financial planning principles that, you know, really are universal. But given your unique circumstances, again, I may tailor my information to you in a certain way and help you achieve that goal because it could be just something that that is different than anybody else's circumstances. And we just have to be aware of that. So the more freedom you feel in speaking with an advisor, just like your doctor, right? You want somebody you can be perfectly honest with and be able to be as comfortable as possible in a judgment-free zone. And that's tremendously important.
SPEAKER_00:
I couldn't agree with you more. I mean, I tell you the more that people share with me, the better I'm going to be able to help them.
UNKNOWN:
Mm-hmm.
SPEAKER_00:
They say, well, I'm having financial problems. Okay, how am I going to give a reasonable, detailed financial plan based upon that as opposed to saying, I make this much money, I spend this much money, I have these issues going on, I have this amount in a 401k or old IRAs that you can roll over. I mean, there is a huge difference. And so... As hard as it hurts, and I know, and quite frankly, because, listen, as a financial advisor, I've had to go to a financial advisor and open up the kimono. Open up the kimono, right? I'm standing naked, right, in front of the emperor, just like, all right, these are my issues. But if the people don't know what you have going on, they're not going to be able to help you. So that's the part. You have to expose yourself. with the fear of being hurt, but knowing that the possibility is that you're going to be helped. And it's hard. It's a hard thing to do. Listen, I eat my own cooking, okay? I've had to do this, and it's not comfortable.
SPEAKER_01:
Well, like some of the most difficult– times in your life, like let's say, and you know, there's some firsthand experience. I hope I'm not, you know, opening up a Pandora's box here for you. I shouldn't be, but when you go through a divorce, you know, that's very, very difficult emotionally and financially. And someone's probably going to be on the losing end of the stick. And that has far reaching implications are going to have to be dealt with. And there's, tax situations that need to be reviewed, retirement plans that need to be adjusted. You have to look at your whole estate planning that needs to be reconfigured and your day to day living, your budget, all that has to be really all thought out all over again because your circumstances are going to be flipped upside down.
SPEAKER_00:
Yep. No, Jerry, you nailed it. I mean, listen, yes, you know, I was married 25 years. a woman and quite frankly in the last four years of it was pretty basically it was just coexisting you know together it took four years to get through the court system so it got finalized about two years ago after 27 years of being together with a woman and it was not pretty and you know she never worked outside the home because she didn't have to because I provided but I'm paying for that. But the point is, is that I, you know, now I'm, you know, I'm sick. I know I've shared this with you, but I certainly haven't shared it with the audience. I lost my pancreas two and a half years ago. So I became a type two or I went from a type two to a type one diabetic, insulin dependent diabetic. I was in the hospital. I was in the ICU. 15 months ago, I was in the critical ICU. I was in a coma for 17 days because my liver started to fail in addition to the fact that my pancreas was gone. I'd been in the ICU five times in the past 15 months. So I'm 50 years old, but I'm dying. And I accept that. I have to go to court tomorrow because I've not been able to work because I'm You know, mostly as a certified financial planner and the things that we do, mostly that's commission related jobs. So I've not been able to work. So I have fallen behind on my child support and my ex-wife is taking me to court to put me in jail because I'm behind on my child support. That's what I'm facing tomorrow. Tomorrow.
SPEAKER_01:
Well, I feel for you, Greg, you know, and I'm really hoping that that doesn't happen. You know, I know that some things are out of your control, but I also really feel that given this,
SPEAKER_00:
there's just something fundamentally wrong. You know, I have a disability, you know what I mean? I get treated differently. I have people look at me when I give myself insulin shots in a restaurant when I eat out because I have to do that in order to live. So when it comes from the sense, the community that we're talking to right now, being looked at, being judged, being viewed and being, I feel that it's just a different angle. That's all. And I, and it's wrong. It's
SPEAKER_01:
wrong. Yeah. Being ostracized and cut out and viewed as different is something that, you know, people in the, LGBT world have a lot of familiarity with, and it's a struggle every day. I know plenty of people who, you know, I've had an ex-boyfriend and a, one of my best friend, both of them actually committed suicide because of their circumstances. And a lot of it had to do with their financial circumstances that things got turned upside down. One was married and things just, didn't turn out for them the way that they had hoped. And I'm not saying that's exactly what caused it, because quite frankly, I don't really know. All I can say is that the end result wasn't good, and both of them are not walking on the earth today. Well,
SPEAKER_00:
Jerry, listen, I think you have a wonderful platform here. I'm glad to be part of it. I'm part of it in a different way. I mean, I am sick and ostracized. by society and by, by life, you know, but.
SPEAKER_01:
Well, I don't think it's the right for you, my friend. I just don't, I just really feel that. Well, I
SPEAKER_00:
hope so. You know what? Like I said, if it's courts at eight 30 in the morning tomorrow, if you, if I'm talking to you at eight 30 tomorrow night, then you know that everything turned out. Okay. But you know, potentially looking to go away. And when I, when I'm looking to go away, they're not prepared. They are not properly prepared. set up for me. My fear is I'm going to walk in, but I'm going to go out feet first, or I'm going to spend half my time in a hospital setting. I'm sick. I have no pancreas. My liver is gone. I'm a type 1 diabetic, and you're just going to put me in general population with people coming in and coming out. What I'm going to be exposed to, I have a 20 times chance higher likely to die than anyone, than a normal individual. So am I worried? Yeah, I'm worried. I'm worried. I'm scared. And reach out to your friends, the community. I am humble enough to ask for prayers. Oh,
SPEAKER_01:
definitely.
SPEAKER_00:
Whatever that looks like for people. Because I'm scared. I'm scared about what's going to happen tomorrow and what's going to happen in the next couple of months. They put me away for bad child support. I'm not a violent criminal. It's child support. It's child support based upon the facts that I couldn't present because of some statute and some screwed-ass rule from 1878 that says I wasn't allowed to present my information. So all the job sees the fact that this is a deadbeat guy who hasn't paid his child support in 17 months with no idea about why it really happened. And so the feeling, and I say this to you, Jerry, you know, the feeling of being ostracized, the feeling of being not heard, the feeling of not having a voice, the feeling of, you aren't recognized for the truth and the value of the worthiness of an individual that you are, I feel it. It's just different, you know?
SPEAKER_04:
Yeah.
SPEAKER_00:
And I know, I know the community deals with that on a daily basis, but you know, I deal with it too. It's just, it's just different, but at least we can have, we can empathize with each other. The fact that we can relate that it's the same. Right. That's all.
SPEAKER_04:
I hear you.
SPEAKER_00:
I'm sorry. You know, I've been running my mouth. I'm sorry. But hopefully this works for getting the word out. And I would love to hear if there's any responses from anyone about our conversation. Well,
SPEAKER_01:
yeah. I mean, if you want to reach out to Greg and you want to comment about this, go on my Facebook page, Pink Money. Just do a search for Pink Money and you'll find it. I'm going to Our website as well, you have a contact link, and I'm going to add a link so you can specifically reach out to Greg as well, whether you want to get financial advice and guidance for him or something else different. positive, hopefully, you know, then definitely as well. So I would encourage anybody, you know, who feels like they've, your story resonates with them and they maybe just want to say, Hey, you're in my thoughts and prayers. Definitely go to our social media sites and go to my pink money website and you'll be able to hook up with Greg as well. Well, and you know, I've taken some of your time, Greg, I know you've told us a lot of personal things. I've certainly, you know, have you in my thoughts and prayers and i wish you all the best i will be following up with you tomorrow you know hopefully everything goes well yeah you know i you know whatever happens to you know you're always my friend and i respect the hell out of you you know not only for your service you know i appreciate you know you're serving but i also appreciate the fact that you're my friend and you're such a smart guy and anybody who works with you is really going to benefit And I know that whatever their circumstances are, they're going to get the best advice and guidance and end up with a friend as well.
SPEAKER_00:
Yeah. Well, Jerry, I, you know, I love you to death brother. I really do. Thank you for this opportunity. There's just with everything that's going on, it just really feels good to be able to, you know, just admit and just, just talk and maybe get, get some things out and not just bury them so deep because I, I've been bearing stuff for years, you know, and, and, and the, the deeper I dig, the more stuff I find, but every now and then it's just like, all right, just take a break and just breathe. And, uh, you gave me a chance to breathe today and I share, and I know I kind of dumped a lot of stuff, but you know what? You are a true friend and I appreciate you and I love you. And, and, um, I'll let you know how things go again. If you don't hear from me, then you know what, what's happening. And then, We'll go from there. But it's not going to be the last time we talk, my friend.
SPEAKER_01:
Never. No, definitely not. Well, again, all the best. And we will have Greg on again, and maybe he'll share part two of his story, and we'll see where that goes. And you will keep tuned in to the Pink Money podcast. So everybody have a great day.
