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A
Hello and welcome to a special combined episode of the Becker's Healthcare, the Becker Business and Becker Private Equity Podcast. My name is Chanel Bunger. Today I have the privilege of speaking with Chris Palmeri, the founder and general partner at Winter Street Ventures, who joins the podcast today to discuss the firm launching its first independent investment vehicle, Winter Street Ventures Fund 1, aiming to raise 100 million to support technology enabled healthcare companies. Chris, thank you so much for joining me today. Could you get us started out by introducing yourself and talking a bit about Winter Street Ventures?
B
Yeah, Chanel, thanks for having me. So I've been in healthcare now for 30 years and was blessed to be CEO of six different large health insurance and care delivery organizations across my career and have been involved in venture investing for probably the last 15 years. So winter Street Ventures is a platform that I created while I was the President CEO of Commonwealth Care alliance, which is a Boston based health insurance company that serves medically fragile individuals that are also on Medicaid and suffering from chronic illness, physical disability, mental illness and seniors aging in place. And I came to Boston to run CCA in 2015 and at that point we were incredibly astute, pioneering organization looking for ways to innovate care for people that needed it most. And one of the ways that we decided to pursue innovation was to create a venture studio which brought entrepreneurs into our organization to learn about the populations we serve, the way Medicaid works and Medicare, and for those entrepreneurs to develop products and services that would be piloted with our consumers and our staff. And we launched that and had many entrepreneurs come and work with us and bring a variety of products and services to those consumers ranging from things like how to do transportation better to get people to and from their doctor's appointments or to and from social events, to how to dispense medications in people's homes, how to innovate care in the community when someone needs emergency level healthcare but wants to receive that in their own living room. Those are just some examples of things that we had done. And if you fast forward 10 years from that inception to today, CCA grew to be a very large insurance company, over 3 billion in revenue. And we made a decision with the board nearly a year ago that we while 3 billion is a large company, we did not have the sufficient scale to participate in the marketplace today. So we joined forces with another terrific non profit, much more scaled organization called CareSource. And as part of that transaction I was able to step away as CEO and I took over Winter Street Ventures as now an independent venture capital firm.
A
Thank you so much for that overview. And now to get into what you came here to talk about, can you talk about the Winter Street Ventures Fund one and what you're doing with it today?
B
Yeah, so I'm really excited. We acquired the platform, which is effectively the name, all of the web addresses, all the things I created over the last 10 years, and then all of the contacts that we had made along the way and all the deal flow that Winter street had when it was owned by Commonwealth Care Alliance. So today I am raising an independent fund. So historically we had made investments off of the CCA balance sheet. Those investments remain with CCA and its current owner, Care Source. So I'm out raising $100 million to make new investments. And our theme is very similar. We're focused on tech enabled healthcare services. Tech enabled things that help healthcare organizations operate more effectively and efficiently. Could be things in the medical record or portals or things that are just not patient facing.
A
Perfect. Thank you so much. And now kind of zooming out a bit. What trends in the health insurance investing or whatever sort of sector would you like to talk about right now that you're keeping an eye on?
B
Well, I think there's a couple things. So first, you know, we have the most recent healthcare bill which is effectively doing two different things. One of which it's going to take out over a trillion dollars in the healthcare sector over the next decade. And that's going to really create significant constraints and force, I would guess, a major paradigm shift. The other thing that's happening is there's an injection of $50 billion of money that's going to be geared towards technological advancements in health care. So I'm really excited about that and I'm really looking towards this time where reimbursements continuing to decline, dollars are coming out of the system, costs are going up, utilization is going up. I think technology, particularly artificial intelligence and predictive analytics, is going to play a huge role in both finding more efficiency and effectiveness in the system as well as potentially making a better and more seamless positive experience for the consumers.
A
Absolutely. And I've already spoke a bit about what you're focused on and excited about. But going into the end of 2025 and into 2026, you talk about what other initiatives or you can even talk about like how you're doing this fundraising. What are you focused on right now?
B
So our source of funds on the fundraising is we're targeting high net worth individuals and family offices predominantly that are interested in investing their money in alternative investments like venture and we're having a great success so far. We really just launched officially right after Labor Day, but we've been having conversations throughout this past summer. And you know, particularly in healthcare, I continue to be focused on moving the location of healthcare services into the home and the community, which is where the consumers, I think, are best served that really need health care. I continue to be focused on people with chronic illness and individuals that are using the healthcare system quite a bit and how to make that experience for the consumer more effective, more efficient, more user friendly, and hopefully less costly for the entire system. I have been focused on the behavioral health sector, which includes substance use disorder, people with severe and persistent mental illness, people really focused on wellness and outpatient mental health services. So that continues to be an area. And in the background, artificial intelligence is going to be the engine that powers all of this. So I think that we're going to continue to see the adoption of more artificial intelligence type technology that's going to enable all aspects of health care. And we're looking for companies that are really leveraging this and any of the things that I just described, as well as a variety of other areas.
A
Got it, Got it. And now I could tell, like in this short conversation that you're very passionate about what you do. And with that, can you share some advice for evolving leaders looking to have that same passion drive and success in their careers as you have?
B
You know, I jumped into healthcare when I was very young and was sort of, I should say, pulled into it because all of my family in some way or another worked in healthcare. My, my uncle owned nursing homes, my older siblings were nursing home administrators. And I decided nearly 30 years ago that I wanted to also enter healthcare, but I wanted to focus on care delivery and managed care and at that point, health maintenance organizations that I was really fascinated by the push for an insurance company to try to keep somebody as healthy and well as possible and accessing primary care. And I learned over 30 years that that's actually pretty difficult to get people to both engage in primary care and live the healthiest lifestyles on their own. And I continue to be really focused on those aspects. I'm also focused on individuals that use a lot of health care, so people that have physical disability and mental illness. One of my siblings suffers from physical disability. He was born with and some mental illness. And he continues to live independently now at 67 years old in the community and is doing quite well. So services and companies and technology that's going to support folks with that profile is something that makes me very Passionate. So, you know, my advice to people that are entering this field is, first of all, you know, it's, it's more than just a way to make a living. It has to be, in my opinion, a calling. And you have to get excited about this because these are, these, these are services that are people's safety net and people's lifeline and people's, you know, access points to having a full and better life. So if that gets you super excited and you want to jump out of bed and do it, despite all the challenges that we read about each and every day in the newspaper of what's wrong with health care, then I would say you got to jump in with two feet if it's something that you don't feel really good about. You know, there's a lot of other ways, I think, to make a living. So. And I think for a lot of people, healthcare truly is a calling, whether you're on the administrative side or you're a registered nurse or a physician that's on the front lines.
A
Excellent advice. Well, Chris, I want to thank you for your time today, but before I let you go, is there anything else that listeners should know?
B
No, I think you covered it. And for me, this is a bit of a pivot. I've stepped away from being a full time CEO to be a full time investor with my own fund. And, you know, my hope is to help aspiring CEOs and entrepreneurs that are learning and building companies for the first time, maybe the second time, be better at what they're capable of doing and, and enable their products and services to see the marketplace and for consumers to access them and see all the good that can come of it. So I really appreciate your time today, Chanel.
A
Of course. Well, Chris, I want to thank you once again for your time today and for sharing your insights on the Becker's podcast. Thank you so much.
B
Take care. Have a wonderful day.
Podcast: Becker’s Healthcare Podcast
Host: Chanel Bunger (Becker’s Healthcare)
Guest: Chris Palmieri, Founder and General Partner at Winter Street Ventures
Date: October 8, 2025
This episode features Chris Palmieri, an industry leader in healthcare innovation and venture investing, discussing the launch of Winter Street Ventures Fund 1. The conversation dives into the fund’s mission—to raise $100 million to invest in technology-enabled healthcare companies—and explores major trends, fundraising strategies, and advice for aspiring healthcare leaders.
In this episode, Chris Palmieri shares a rare blend of personal motivation, professional insight, and market vision. With Winter Street Ventures Fund 1, he aims to drive healthcare innovation by funding technology-enabled solutions, focusing especially on underserved, high-need patient populations. From bold shifts in market dynamics to heartfelt leadership advice, Palmieri’s perspective is a valuable guide for anyone aiming to build or invest in the future of healthcare.