Meeting between Dmitri Sunshine and Jaime Haak — Full Transcript
Date: March 17, 2026 | Duration: 31 min | Speakers: Jaime Haak, Dmitri Sunshine
Jaime Haak: This meeting is being recorded. Hello. Hello.
Dmitri Sunshine: Hello, Jamie.
Jaime Haak: Hi.
Dmitri Sunshine: How are you?
Jaime Haak: Great. Would you say how or where?
Dmitri Sunshine: Well, actually, I want to know both.
Jaime Haak: I’m fantastic. And Santa Fe.
Dmitri Sunshine: Oh, okay. Why Santa Fe?
Jaime Haak: Why anywhere?
Dmitri Sunshine: Yeah. But, like, why now? Like, what? Drew.
Jaime Haak: The opportunity presented, though, and I said yes.
Dmitri Sunshine: Okay, so you’ve got something there that’s pulling you in.
Jaime Haak: Yeah.
Dmitri Sunshine: Oh, okay. I mean, Santa Fe is gorgeous. I mean, I. That’s. I actually miss. So when I would go visit my son in Sedona, we would. We used to drive through Santa Fe, and now we have a Model 3, so we take the. The suggested route, which is, like, through Moab.
Jaime Haak: Totally love that I came through Moab. Coming here too. Yeah. Lovely drive, which I. I. I tend to, like, go to the next place, but this last time, I was, like, A little more time in Moab would have been nice, but I did know Matt there and spent some time there already, so I can’t complain too much.
Dmitri Sunshine: Gotcha.
Jaime Haak: Yeah. Beautiful city. Magnetizing. I keep coming back.
Dmitri Sunshine: Yeah. Well. So, Jamie, what’s. What else has been going on in your world, like, since we had. Since you had this beautiful little birthday party? I felt so honored to be able to attend. Thank you.
Jaime Haak: Yeah. Thank you so much for coming. It was. That was such a random and fun time. Gosh, I don’t know. I was in Dubai for World Health Expo. Was in Boulder a little bit. Right. For friends, but, like, felt like it was in and out in such a frenzy because of Dubai. And then I went to Jordan, and then I had, like, a week, and the guy that I was seeing on my birthday, we were gonna travel together and then ended up stop seeing each other. So that was a bit of a whirlwind, but good. And then I was in Boise helping a friend with her two boys, and now here. That’s the CliffsNow.
Dmitri Sunshine: Okay, sweet.
Jaime Haak: How about for you?
Dmitri Sunshine: Nothing anywhere near as exciting. I mean, we’ve got a baby coming in mid May, and so just preparing.
Jaime Haak: I would argue that’s exponentially more exciting, but.
Dmitri Sunshine: Yeah. Yeah, it depends on which. Yeah, depends on how you look at it. Um. But yeah. And just. And scrambling to get this consulting firm launched in time because I think I went too far without generating revenue with my startup. And now I’m like, okay, do the thing, you know, that works for sure. And, I mean, it’s exciting. I’m excited because I would love to be in the wealth management ecosystem.
Jaime Haak: Okay.
Dmitri Sunshine: Interesting to pave the way for something that I want to do after this. Okay. Yeah.
Jaime Haak: Right on yeah.
Dmitri Sunshine: And you’re still focused in healthcare, right? Like that’s your. Yeah, always. Okay, cool.
Jaime Haak: 100%. Yeah, yeah, totally. Yeah.
Dmitri Sunshine: So, so I’m curious, like what are you seeing right now? Like where are you work? Like what’s your, what’s your main focus right now? What do you see as like these big opportunities coming up?
Jaime Haak: What’s the qu. Sorry, can you ask the question again? What’s my, what’s my focus? Or like where do I think healthcare or what’s the.
Dmitri Sunshine: Yeah, yeah, like what are you, what, what specifically are you doing in healthcare and where are you seeing like these biggest, the biggest opportunities right now like for the, I mean besides you know, the typical AI disruption. But yeah, am I, I feel like
Jaime Haak: you’re asking me vastly different things that I’m not totally sure what you’re asking or what the context is. Maybe. Okay, I, I have a little health tech consulting business. That’s what’s like making me a little bit of money now. I consult founders on how to make money in healthcare and it’s all over the board and very people centric less than do I think this is the next unicorn centric, you know, so I’m not really focused in this like bleeding edge space that maybe you’re asking about my other business that is small. We only have a couple clients but we’re only a year old, growing quickly, hopefully closing a big contract here in the next couple months. But we move money from health insurance companies to providers using. Ideally we’re not like quite there yet because the healthcare industry isn’t there yet. But we’re the first ones who are bringing real time payment technology to healthcare. So it’s not sexy, it’s not something I ever thought I would do. But I think it’s an important disruption moving some of the business away from these extortionist middlemen who historically charge like 2 to 5% from a provider for basically doing nothing. So we’re like kind of becoming a commodity in a way which is not that exciting, but it’s better than not doing anything. And I think the technology that we’re leveraging might be interesting in the future to other things that I eventually want to do and, or just like it’s going to be a no brainer that the whole industry is using this RTP technology. The rest of the world uses it. Like you buy a churro in Mexico City from a vendor, from a cart vendor, right, like, and you’re using rtp. But we, it only came to the United States just a few Years ago in 2023, FedNow became a thing. So. Yeah, that’s what I’m doing.
Dmitri Sunshine: Okay. So that’s, that’s the main focus right
Jaime Haak: now, those two things. Yeah. And arguably it’s more than two because I have numerous clients and I have an executive coaching client that, you know, so lots of irons and different fires, so not an easy question to answer really.
Dmitri Sunshine: Okay, got it. Okay. So there’s a, there’s both my way of asking and then there’s also the complexity of how much you’re doing.
Jaime Haak: Yes. Lots of, lots of things swirling, which is really fun. Yeah.
Dmitri Sunshine: Yeah. Where do you guys need the most help right now?
Jaime Haak: Like with the small startup, the fintech startup.
Dmitri Sunshine: Yeah.
Jaime Haak: I don’t know.
Dmitri Sunshine: We’re.
Jaime Haak: We’re help in what way?
Dmitri Sunshine: Just, I mean, what should I keep in mind in case if I know people that can help out or if our firm is actually, you know, positioned for this even though we want to focus more on wealth management. But fintech is definitely such an interesting nut to crack.
Jaime Haak: Yeah. I mean we’re importantly for us bootstrapping and feel like we have, I mean my co founder was the chief product officer of Elevance. So like between the two of us, we have all the kind of expertise that we need to kind of do what we need to do and are keeping resource expenditure like very, very low and importantly like growing really slowly on purpose. So honestly nothing because we just like we kind of have what we need in house and. Yeah. And are like again being pretty methodical about the way that we’re looking at growth. I’m sure that won’t be the case forever but like, you know, we have what we need at least for these few clients and then I think once we get to a point where we’ve got volume which means we’ve got revenue to invest more in growth, you know, that conversation might change but it’d probably be like full time, you know, engineer kind of talent that we would, would be the next kind of thing that we would look to source which for my, you know, Palantir alumni roots and things like that of a good network to pull from and anish to having, you know, been in product and engineering in healthcare for most at Apple and then in healthcare at Cigna and Aetna and Elevance like I mentioned. So we probably pull from like, you know, our first degree kind of connections for that kind of thing which is nice to be able to do after so many decades like beating your head against the wall in healthcare. Now we’ve got like some things that, you know, or life is easier in some respects because of all that grind that we had to go through, but. Yeah, yeah, yeah, yeah, yeah. But I mean, if you tell me a little bit more about what you mean by wealth management and how fintech relates to that, I mean, again, I’m consulting for a bunch of different health tech founders and there might be something there, but it’d be too hard for me to like, rattle off who I’m advising and working with and like, what they all need. Way easier for you to tell me what you do and then maybe I can identify something that way.
Dmitri Sunshine: Yeah, yeah. We’re focused on the, what we’re calling operational resiliency or operational robustness. Because, I mean, what I see whenever I get an inside view into a company is it’s like essentially it’s like really long, untied shoelaces that people are getting ready to trip on at any moment and they’re like, no, it’s fine. I don’t. You ever been walking with someone and they’re like, shoelace, they’re untied and you know.
Jaime Haak: Because I would stop them immediately.
Dmitri Sunshine: Yeah, yeah. So it’s, it’s a hard sell. I mean, but what we ultimately want to do is be able to come in as like the, it’s kind of fractional operating like almost a CIO or csio to help information, not innovation. Yes. Yeah, Information innovation. Yeah. But just keep them running along because I feel like, I mean, a lot of people know what they need to do. Like, there’s a lot more people that know what they need to do but aren’t doing it than there are people who don’t know what to do. So we’d love to come in. I mean, cyber security assessments is kind of like our wedge of like coming in. It’s like, let’s just make sure, like you’re not going to get hacked tomorrow. Right. Like. Or that, like some old employee doesn’t have all the keys kind of thing that. Yeah. You don’t have like a huge exposure. It’s kind of our way to start working with engagement so people can see like the level of detail that we go into.
Jaime Haak: Yeah. And that you have specific healthcare expertise in that because that is a pretty, like, it’s a discrete thing that is different than like if you wanted to do that for other industries.
Dmitri Sunshine: Yeah, yeah.
Jaime Haak: So the, the software regulatory environment is so different.
Dmitri Sunshine: Yeah, yeah. The software company that I ran, so we were doing child welfare management, so we were getting into HIPAA and a Lot of medical information in there. And that was a shit show. Yeah, it was really bad. I mean, it’s because, like, from like a software provider standpoint, you, you know, you provide the tools, but then the real work is up on the clients and, you know, they’re not doing it. Yeah, yeah, yeah, yeah.
Jaime Haak: And for not there, usually, I think that’s the, that’s the problem too with the startups that I’m at. I would argue most of them don’t know actually what they don’t know. And they know there’s a lot that they don’t know. And they don’t necessarily know how to approach all of that because there’s just a thousand different threads you could pull at any moment. And knowing which and when and why is really, really hard for anyone. So it’s not like they know, oh, this is exactly what I would do. But also, the resource constraints are so extreme usually that they’re not. Even if they did know, which in many cases they don’t, they still wouldn’t have the resources to put behind doing the thing unless they have to. And then they figure it out. Right?
Dmitri Sunshine: Yeah, yeah. I spoke to, had a discovery call yesterday and they were in that same place where it was like, we really need an operator come in, but we can’t afford to have an operator come in. But if we could, if we could somehow get the funding, then that would get us to the next level. So it’s this weird, like, chicken and egg thing. I’m like, wow, you guys are stuck.
Jaime Haak: Yeah, exactly. Yep, I see that a lot. And then I go, cool, call me when you raise capital or call me when you want to spend some money on somebody who can help you raise capital. Right. But in the meantime, can’t work for free. I once did a no twice now. The second time worked a little better. Well, I don’t know. Anyway, I’ve taken equity for, like, to discount my rates and I don’t. I’m not doing that anymore. I’m not. Almost certainly, like, I’m gonna get paid and get equity. Not one or the other. You know what I mean? It’s just. Yeah, yeah, yeah.
Dmitri Sunshine: What would you recommend for us? I mean, specific, like, it’s mostly me right now handling this firm. And like, how did, like, you got started? Because I assume you had this network from your past jobs. I feel like I’m kind of starting over. Like, I can’t really go to past clients in that child welfare management world because, I mean, I actually don’t want to work with them. I want to work with maybe foundations just because I want to get more experience with special assets handling for this next thing called Lasting Legacy foundation that I would love to work on. It’s probably like five, ten years out, but. Yeah. How would you get started if you didn’t have a network?
Jaime Haak: Gosh, I don’t know. I mean there’s kind of two, two avenues. One is like go full time doing the thing you want to do fractionally so you have the. Because like you, I feel I don’t know how I could do what I’m doing without having done it a hundred times before. You know what I mean? So. And I don’t know, I guess I don’t know whether you’ve or not you have done it a hundred times before, but if you haven’t, then I would say just find avenues to get at bats. Right. And the easiest way in my mind it would be to do that as a like executive at a company and then move into like doing it more broadly for more kind of clients. Barring that, I mean I, I guess like become a good storyteller to connect the dots between what’s hypothetical, right. And like what you could actually do and when and how. And then the like for whom just I, it is still networking, right. Figure out the, the like for whom and make some assumptions about like what your sales funnel will look like. So if you want to have three clients, how many proposals do you, will you sell three out of three proposals? Probably not. Right. So like do you need to issue 10 proposals to, to make some assumptions about what you think is reasonable and then keep working your way. So I typically structure a sales funnel. Like you’ve got top of funnel. Usually I’ve got two buckets within that top of funnel, warm and cold warm. I tend to convert at like 20% cold 1 to 3%. So how many of those inputs do I need to get to introductory meetings? Just like pitch meetings. It could be informational interview type things to see if I’ve qualified that buyer. How then how many of those are going to convert into like actual discovery. They’re a qualified buyer and now they’re spending time with me to actually move them along in the sales process to that next stage of like, great, I’ve issued them a contract and now the final output of I’ve closed a contract and I would just do the, do the math and then divide your time up accordingly to know you’ve got the right number of inputs. And, and then you can say okay, my week, my monthly, weekly Daily goals to just really work the system that way and then check your assumptions. Like, I thought my conversion rate between these two elements of the funnel was going to be X, but it’s really Y. So I’ve got to change some lever within there to either increase that conversion rate or bring in more inputs. And how do I do that? Like, that’s probably where I’d start to like try to figure out how do I achieve what I want to in the time period, especially with the baby on the way. Right. The time period that works, given are you taking time off for, you know, for new baby? Are you, you know, what are your financial needs and things like that to like force myself to, you know, have a hypothesis that I can get behind. But yeah, I don’t know. So there’s, I answered a little bit on the marketing side, but really, you know, that maybe it’s probably starts with the funnel and then you can figure out how the marketing pieces fit into that accordingly.
Dmitri Sunshine: And were you doing outreach on LinkedIn or how are you connecting with people that like, what’s your cold outreach strategy? Or you don’t need.
Jaime Haak: I don’t, I never have. No. And again. But like, I’m such an anomaly. It’s not, you know what I mean? Like, I, I don’t know anyone else in this fractional space who has had it as easy like, and I’m not also not trying to have 10 clients, right. I have like one to three clients usually at a time. So what? And maybe I’ve had a couple more than that at a time, but one to five still. Like, you know, I, I’m also carved out. I’ve carved out a lot of time for myself and I’ve carved out a lot of time to be flexible for this fintech startup. So I have pretty reasonable and low goals and very low kind of overhead requirements for my life. So that’s made it really easy, I think, to close deals. But the truth is it’s just because I’ve been in one industry, in one function for decades. So the moment I started putting the feelers out, it was just immediate, the lead start coming in. I sometimes see things like people send me stuff, even if it’s not for their company necessarily. So that helps in a lot of cases. It’s like health tech nerds. It’s Pepper, which is a New York City like healthcare community. There’s a group called Fractionals United, but that’s not the one. Wait, what is it? What’s that?
Dmitri Sunshine: I think so. I mean, I’ve been Hearing a lot about this.
Jaime Haak: Oh yeah, no, that is one. Sorry, that’s not the one. I’ve. I’ve never gotten business from Fractionals United. I didn’t mean to say that’s not a group. It is a group it now costs to be part of and I’m. I didn’t see value in paying for. Is. What is the name of the group? Taylor Crane runs it.
Dmitri Sunshine: I don’t know that.
Jaime Haak: Yeah, I’ll. I’ll say I’ll forward you the next newsletter. He. He sends them all the time. Let’s see, we’ll just pull it up. And so there’s a bunch of other. It’s. I think it’s just called fractional drops. Yeah, here it is. This is the one from yesterday. So like things like that. For sure. Are you at Sage Dot Solutions?
Dmitri Sunshine: You could send that one. Yeah, that’ll get to me still.
Jaime Haak: Solanasis.
Dmitri Sunshine: Solanasis. This is such a weird thing. It’s one of those things where I’m like, I don’t know how this came to me, but it’s like the thing that stuck and ended up going with it and I’ve never heard it pronounced correctly on the first try.
Jaime Haak: Yeah, I mean like, because I. I was saying it as I was reading it. I didn’t take a beat to like, you know what I mean? Maybe if I thought about it. But I think I need like a little soul. And so you want to start saying soul, you know, anyway, which is one of those two that I should forward this to.
Dmitri Sunshine: Yeah, the Solanasis one. That’s a lot. Yeah, they’re all get back to me.
Jaime Haak: I mean, great, cool. So, yeah, that’s just fractional jobs. IO so there are groups like that that I think there’s one called like nex, I think K, N E X. That was free. They’re now charging. But I. Again, I’ve never gotten any business from them. They’re not. Neither of those two are healthcare focused. So every once in a while maybe I’ll see something. Fractional jobs. I did just apply for this like fractional chief of staff role at a company that. A health tech company. So we’ll see. I don’t know that it’s. That will go anywhere, but I just. I don’t know, I keep an ambient sort of, you know, eyes open and otherwise, but really things are just sort of falling into my lap. And I’ve. I’ve never liked that funnel that I was recommending for you. I’ve never done for myself, not for my own consulting Business. I do it for my clients, but I’ve never done it for my business. I’ve done it for the fintech company, but not the consulting business that I have. Yeah.
Dmitri Sunshine: God, you’re so lucky.
Jaime Haak: I know, I know. Trust me. I am grateful for that luck every single day. And also that I remind myself, like, I worked my fucking ass off and went through some really, really tough shit to get to this point where things are coming more easily and in the flow. But yeah. And I’m not so arrogant to think it will be forever. So. Yeah, I don’t know. Which maybe it will be, I don’t know. But have other irons in the fire on purpose. Because I also don’t know if I want to do it forever. Maybe it’s pretty fun. But what.
Dmitri Sunshine: What else would you consider doing?
Jaime Haak: I don’t know. If I did I do it. I mean, I have a business idea that we don’t have time. It’s too. It’s too complicated and nascent.
Dmitri Sunshine: Really?
Jaime Haak: Yeah.
Dmitri Sunshine: Interesting.
Jaime Haak: But that’s probably like 10 years down the road or something.
Dmitri Sunshine: God, you’re building up so much anticipation for it now.
Jaime Haak: What the hell is it? I thought I was gonna build it like two years ago with Stand Together Ventures Lab, and they didn’t get it. Like, they got it initially. They were like, yes, come and be this entrepreneur in residence. And they’re like, never mind. It’s too difficult. And I’m like, fair. I know that. But I haven’t given up on it yet. I had this idea that I was going to pitch Alice Walton eventually with it, and did you see she just opened a med school?
Dmitri Sunshine: No.
Jaime Haak: Yeah, like last week maybe or something. I don’t even know that much about it yet. I have a bunch of articles open on my. My tabs to read about it, but that’s all I know. It’s from the headlines. Yeah.
Dmitri Sunshine: Okay. Interesting. Okay, well, so we’ll come back to this then. Cause I definitely want to hear. I mean, that’s. That’s one of my most exciting things, is to like to meet with people who have business backgrounds and share their visions. Because I meet with people who don’t have business backgrounds and share visions. You’re like, shit, that’s never happening.
Jaime Haak: Exactly. Yeah. Which might be your reaction to this idea too. But, like, the economics of healthcare, that’s the idea, though. It’s like you have to change delivery, access and the economics all at once. There’s no way to really make change or create a new health, not sick care system without all three and you have to divorce health insurance from employment, ideally health insurance and the concept of it goes away. We’re not in our lifetime going to see that at a federal level. So it’s like it needs to happen at a local level. And imagine what you would like with what kind of services and community yields health promoting and sustaining activity. Right. Actual health, not health care. Right. Not sick care, but actual health. How do we encourage people to live in an environment where access to nutrition and physical activity and intergenerational communication and community. We’re pack animals, right. To have that, that social element and spiritual health and creative health and housing and financial health. Right. Like these are the things that on a day to day basis lend to us being vibrant, happy humans who can bring our talents, our unique talents into the world. Right. Like that’s what I want to build.
Dmitri Sunshine: Wow. Wow.
Jaime Haak: I love people slowly extract them from, from the incumbent sick care system into that. Giving them the option, self selecting the people who get it, the vision, giving those people access then to like, yeah, we still need operating rooms and tables and infusion centers and let the health like let the hospitals do what they do. Let the surgeons cut, let the phlebotomist needle. Right. Like we don’t need, we don’t need them on a day to day basis ideally. Right. So like, and then you can operate without a network and go, what is the healer that I need for the specific sick care that I need? And then you, you go get it.
Dmitri Sunshine: Yeah. Love it.
Jaime Haak: And we have excited $738 billion to play with in theory. Right. Like that’s what employers are spending on self insured products alone.
Dmitri Sunshine: Yeah.
Jaime Haak: We could spend $738 billion to make people employed, people healthier. Like what would we design? Right.
Dmitri Sunshine: Yes. Yeah. Okay, so we gotta come back to this because there’s a lot of overlap between this, this Conexus community concept. I don’t know if I ever pitched you on it, but it’s very similar, but it’s much more nuclear approach of like you’ve got these communities. So it’s not widespread. But imagine like in every city you’ve got the entrepreneurs, you know, these kind of like thought leaders that are. It’s a living, breathing day to day mastermind. And you have all your food supplements, everything’s provided, it’s one fee, so you can’t opt out. It’s kind of like all or nothing anyways. But we’ll come back to this. Yeah.
Jaime Haak: In the first place, was it health tech nerds, something like that? Right.
Dmitri Sunshine: I think it was a random LinkedIn outreach, but maybe it was through because I was at Human Potential Summit, and I think. I don’t think you were there, but I think you’re. Because you were involved with the Stand Together. Yeah, that might have been the rap, but.
Jaime Haak: Yeah, could have been.
Dmitri Sunshine: No matter.
Jaime Haak: Yeah.
Dmitri Sunshine: Well, it’s good to see you.
Jaime Haak: You too. Thanks for reaching out. Yeah. And I’ll let you know, I’m probably going to be back in your neck of the woods. I’m just working on my schedule. It went totally topsy turvy, but it looks like probably the month of May. Most of May.
Dmitri Sunshine: Oh, okay.
Jaime Haak: We’ll see.
Dmitri Sunshine: Let’s see. Because our sun is due in mid May, but. But, you know, hopefully it’ll be really clear closer to the time frame. So if that’s before. Because afterwards it’s gonna be like nesting.
Jaime Haak: Yes. He’s due when?
Dmitri Sunshine: Mid May. Like, May 15th, essentially.
Jaime Haak: Okay, cool. Yeah, I mean, I’m planning to be back by May 2nd, probably.
Dmitri Sunshine: Okay, cool.
Jaime Haak: I’ll keep you posted regardless. Yeah.
Dmitri Sunshine: And hopefully we’re going to start doing these, like, early morning, like, weekday morning hikes up and down Sanitas. I don’t know if you did that before, but it’s really fun. Great group. We were doing that last year. Nobody want to do in the winter. Surprise, surprise. Like, because getting, you know. Well, I mean, we were starting at, like.
Jaime Haak: I’m kidding. Yeah, I’m fickle like that, too. I would not be. I. I was 100 kidding.
Dmitri Sunshine: Yeah. All right, Let me know when you’re back.
Jaime Haak: Okay. We’ll do. Absolutely. Thank you. Thank you.
Dmitri Sunshine: Jumping on. Yeah. Ciao.
Jaime Haak: Bye. Bye.