This Impact Angel Investor Reveals Their Secrets, Plus how Rural Hospitals Can Finally Get Paid - Joseph A. Riddle

How do I find an angel or a seed investor? What are they looking for from me? How do I get ready to prove to somebody that I'm ready to be invested in? These are the sorts of questions that Joseph gives just incredible, solid advice for, as well as, how founders can stay grounded and focused in the work that they're doing. I have purposely stayed away from startup funding conversations because it has seemed too complicated, too nuanced, and too out of my scope of interest. But when I met Joseph Riddle, that changed. Joseph is an expert practitioner in a number of things that I care a lot about, and on this episode, we talk about climate solutions, we talk about tech optimism and why he sees that we can use technology to innovate our way out of some of the world's most difficult problems. Specifically, he's working on tackling climate and healthcare in America. We talk about the work that he's doing at Capital Pulse, which is a surprisingly compelling innovation for healthcare revenue cycle management, which usually means business software. But in this case, it's an innovative approach that builds some really interesting, changes in financials for rural healthcare systems in particular I am so delighted that Joseph allowed me to ask the probing, curious questions that so many startups ask me when they're talking about getting their ideas off the ground. As somebody with multiple exits, Joseph had two exits in three years, right? So this experienced innovator shares some advice that might be hard to hear but is well worth your time. And simply put, hey, founders, like, yes, your novel innovation is absolutely new and unique and necessary, but the kinds of problems you're working on, the infrastructure that you need to build, the types of decisions that you're making have probably been made before, and you don't have to do everything alone. Get out of your head, get out of the boardroom, go talk with advisors, go talk with your users. The answer is out there, and you don't have to start from zero. Incredible advice from somebody who has been to the top of tech innovation a couple times and is still into it, right? And he'll tell you how to get his attention, if you wanna pitch an interesting climate or health tech idea. This is a fantastic episode getting into the nitty-gritty of tech innovation funding and financing with angel investor and chief commercial officer Joseph Riddle Hello, and welcome to The Tech Glow Up. I'm Nathan C., and today I'm talking with Joseph Riddle. He's the Chief Commercial Officer at Capital Pulse and also an early stage and angel investor. it is so great to talk with you again. thank you for joining me on The Tech Glow Up

Absolutely. Thank you so much for having me

Oh, goodness. you do so many interesting things. I'm sure I summarized it, only half as, detailed as you could. Could you, to start us off, introduce yourself and the work that you do?

Yeah, absolutely. so at this point in my role, in my, in my life, I'm a fractional chief commercial officer, and I do, as you mentioned, do, I'm an advisor for early-stage companies. I began my career, well, originally I began my career as a, as a researcher in human resources for a division of Gartner, researching, you know, best practices for, what makes an, an, equitable and harmonious workplace, right? and then I ended up working for a company called SmartBrief, which is actually a really large publisher a lot of people have never heard of because it, it publishes under the brands of trade associations and professional societies. And I, my, my undergrad was in sociology and my master's is, is in economics. And so, eventually I moved into an operations role with SmartBrief, where I was the publisher of a business unit that was publishing all of our materials in education, workforce, and the path to development. So the kind of synthesis between education specifically and the economy has been something really important to me. and then, I had an exit. I was employee, number twenty-five at that company. they sold to Future PLC, a big international publishing conglomerate, and, I took a left turn. I turned into tech marketing. I had seen thousands and thousands of, digital marketing campaigns deployed, so I had a ton of data, but I'd never been a marketer myself. I was like, "I'm gonna try this." So I went to an early-stage company. They took a chance on me 'cause I had not, been a formal marketer before. I took a chance on them. I thought it was a founder with a great idea. they did not pay me. I took an equity stake, so for eight... And actually, I paid them. I gave them money as a backer. but I had another successful exit within three years. so I had kind of two back-to-back, and then I started thinking, "Well, how can I be intentional about this, about my investing?" having seen the power of good ideas, coming to fruition, I wanna do things that really matter. Not that media isn't important, but I, but, you know, I think partly through my work and working in education so long, I, I now spend my time in, in what I consider to be the two big problems facing humanity, healthcare and climate. And I think education is a third, but there's so many policy implications, and I think there's less room for tech to be an innovation tool in education. So, so I've chosen to focus my energy in healthcare and climate tech.

Okay, I just wanna call out that education is a harder go to market than healthcare or climate. I mean, I, I'm oversimplifying what you said, but, like, the, to just point out the complexity that, you know, something that's, like, legislated and mandated at so many different levels, it's so regional, so cultural, amazing

between investment and results is less clear in education because quality matters so much versus quantity, right? So there's just a lot of intangibles that make that a, a very, tough nut to crack. Obviously, healthcare and, and climate are huge. There's regulatory hurdles, there's all kinds of hurdles, but there's a director...

Absolutely. thank you for, taking us through that journey. This idea of, being the connection between the education and the economics, I think is such a powerful perspective. You know, every time I talk with a startup, typically the biggest question is, like, how do I get funding? What's the right kind of funding? You know, how do I go forward with this? How do you build those cases, and get the right kinds of, both attention and support? I love that, like, your curiosity. And it, and it seems like almost... Th- this, like, the, the curiosity, and also that, like, consistent connection to, like, how are we talking and communicating and educating about these ideas we are also, like, building viable models and, you know, getting behind products actually make a difference, founders that are actually, you know, doing it for a reason that you can get behind on so many levels.

Mm-hmm.

There's a question I wanna climate and healthcare are, like, two of my top special interests.

Right

I'm curious, how do... But, like, they feel very different, very nuanced, very, like, similar and yet totally different worlds.

Mm-hmm.

Are there, from your perspective, either as, like, a product or a marketing mind or as an investor, that you, see similarities or threads between, what it takes to be a successful innovator, in climate and in healthcare?

honestly, no. I don't, I don't see... I mean, I think they're, they're very distinct kinds of entities. The, the, the real common thread, I suppose, in my mind is the, is the, the critical importance, the role they play, each of them in, both in, I think, what will be a ver- the version of the healthy economy we're moving toward and in, you know, human life. we all have to deal with healthcare. We all have to live in this world. if there's two areas where I think innovative thinking needs to be applied, it's those. There are fires to put out everywhere, but if I had to rank order them, I really do think those are two of the most pressing challenges facing humanity and particularly facing the United States because of where we are right now and sort of the political and economic transitions we're making, in this, very, very tense moment, so

When, as an early stage investor, as a angel investor, often, and, and as a, a startup advisor, often one of the roles that you play is, not just to, you know, give specific advice around tactical or technical or network things, but also to, sort of share that perspective, that encouragement to keep going, to stay focused. Looking at those challenges that, you're kind of running straight at,

Yeah

how do you stay inspired or how do you help, the startups that you work with, stay inspired and focused and, patient, in times like this?

Yeah. gosh, there is a quote I love. It's, and it's, "The antidote to anxiety is action." and, and I think as we think about, you know, these are vast, complex problems, what's the way to do any big task? You just do it one little bit at a time. The, the way to eat an elephant is one bite at a time, something like that. and It's just getting in there and doing it and realizing that, that if you have a unique perspective on the problem, the chances are really good that it's complementary to the... It's that someone else isn't doing exactly what you're doing, but it is probably complementary and will have compound effects as you link up with people who are doing, who are looking at the problem in a similar way. and, and I think it's those unexpected, unlooked-for little, you know, those little moments of serendipity when you realize, "Oh yeah, you're doing this this way, and I'm doing it this way, and if we collaborate..." Or sometimes it's just sharing thinking. It's not even necessarily a business collaboration. I think that can be so motivating, right? when you're thinking about problems that are so complex, is to realize you're not in it alone, that other people are coming at it from, from angles similar enough to yours that eventually you'll arrive at a point of, of crossover.

That I, in the co-working space that I'm in now, the, are many founders and, and when there's even just like a scent of like a common struggle or a shared perspective or, or like, whoa, we're like synergistic, th- like it's euphoric. Like you can hear it, you know, across the hall so

Yeah

Joseph, you alluded earlier when we were talking, right, that im- impact work to correlate to measurement and being able to prove the impact, to prove the economics, prove the change that's happening. and so I'm curious, pick, you know, the example that, that fits best for you. when you're pushing, you know, the boundaries o- of a, of a new idea or a new technology, are your favorite ways to, to learn about and to measure the impact, that you're having for, for customers or, you know, healthcare users or, you know, inhabitants on the planet? how do you learn, what works and, and what to double down on?

Oh, gosh. well, in a, in a business-specific context, I think, y- you know, I, I, I'm not one of those people who treats anecdotes as, as meaningless. I mean, there's, there's data and there's anecdata, right? And I think y- I think the best, the best way forward is to synthesize the two in as much as possible. It's, it's... I think it's a combination of, of, of talking to people, hearing what their problems are, proposing solutions, and asking them to... and, and iterating s- solutions. surveys, testing marketing data. Te- te- testing messaging can actually, I think, be a way to do product refinement. Because if you get it the best way the client is framing the problem in their mind, that will get you closer to a solution that, meets their need.

And, anytime, you're advising, like, take your ideas and put them in front of the people you're trying to connect with and, like, watch how they respond, like, that's amazing data. And, just, a week or so ago- couple weeks ago, Katie Tucker at GM was talking very much about how she loves to take the qualitative data to her quant team and be like, "We got some signal. Like, what does this speak to you?" Right?

Yes. What, what luxury to have the resources to be able to do that?

To have both sides.

Yeah

I think I would be remiss, Joseph, and this is a little bit of a sidebar on, I've got an angel investor in the room, and, like, can I, can I give a hand up to all the startups that I talk to, the ones that looked at me for advice. one of the big questions that I've heard pretty frequently, right, is, I don't know where find the kinds of investors that I need now, and I'm never quite sure when I'm ready to talk with an early investor. do you have advice, maybe in general or, you know, as, as specific as you care, you know, to, to climate technologies or others. how do you, how would, how do you recommend, you know, connecting with and finding the right kinds of advisors?

Mm-hmm.

you have an early idea, when, what do you need to have ready to sort of open those first conversations?

I hate to pile more on an entrepreneur's already full plate, but I think, you know, I'm gonna recommend a couple of really good books. a book called Angel Investing by David Rose and, one called Venture Deals by Brad Feld. And I think that that will help any entrepreneur really get in the mindset of, of how investors are thinking about evaluating early-stage startups. What, you know, what they're looking for, what they care about, how they're-- what kind of deal structure they're gonna be looking for to assess your credibility, your viability. so I think, I think those are really good resources. you know, I obviously having, having a presence on all the, all the len- the, the platforms where investors meet founders like Dealum and Gust. making sure that you have a profile there that, Let's, Let's Play Money is another one, which feels, you know... It's, it's sort of funny how they're, they're trying to gamify investing. I'm not sure I love that, but it, but it is a valid platform, and I think making sure that your, you know, your profile there is, is complete, you have a comprehensive pitch deck that describes the strength of your leadership. people invest in startups for different reasons at different phases. and at, at, at the beginning, if you're looking for seed money, obviously it really is just, just... It's the strength of the idea and whether the person you're talking to thinks you are the person who can do it, thinks you have not, not necessarily even the best technical answer, but the, the, the chutzpah, right? I think it can be, Yeah. And, you know, for, for companies with a really high CapEx, like where it's gonna be super expensive to even produce a, an initial prototype, sometimes it's really just you and the idea that the founder is betting on. Obviously, the closer you can get to producing something workable that's proof of concept, the easier those conversations become. and then a little further down the line, when you're past your kind of pre-seed and you're getting in more into Series A, then they're gonna start looking at, you know, you're t- really getting the fine-tooth comb out to look at how you're evaluating the total addressable market and your path to getting X percent of it, and whether that's viable via the, via the leadership you have and the marketing you have planned and the, you know. so the scrutiny gets a little finer with each level you rise up. And of course, you're asking for higher sums of money and the return gets lower, honestly, because that becomes a safer bet. the further a startup is up on that growth cycle, the more leverage they have in th- that negotiation with an investor, right? because the proof of concept is already there. So, you're gonna have a much bigger risk with your early-stage investors. but if you can get buy-in from them, I, I don't know if I'm answering this from the entrepreneur's perspective. I c-

Oh,

for me to get out of my investor frame

I totally wanna thank you for first suggesting like, hey, do the research and like, you know, know the fundamentals before you start, you know, asking, you know, people to do the work for you. I think w- in my experience, early investors, seed investors, advisors are always glad to share their time, especially when they know it's gonna be worth it.

Mm-hmm.

and that, you know, like you said, a lot of times those early relationships are about how the founder is showing up, how the founder is prepared, how they understand their customer and the, you know, the differentiation on the question. And, right, the bells and whistles, the, the deep tech, you know, those are things that can help. but really, you know, the clarity of your mission, you know, the work that you've done to understand the space that you're playing in. I, I think something that early founders struggle with, right, is, is that, that confidence to be the one to solve the problem. and I really love, right, like, that you called out, it's like, show me why it's you. and I, I, I think a lot of founders, they feel like they have to prove it some other way, and I, I, I totally wanna double down on the like, you know, make it undeniable that you're the one. So Joseph, usually, you know, the, the... often I like to ask, you know, when we're looking at new ideas, how we test and learn and grow quickly is usually, like, determines how quickly we grow as an organization. can you talk, you know, at any level that you're comfortable with, about how, you know, that information that you're hearing from your customers, your advisors, you know, your audiences, has changed how you've understood a product that you're working on? And, you know, whether it is in response to, you know, new opportunities, or challenges, you know, how, how do you, you know, take those, new data points and, and bring them into a product's, success journey?

Ah, that's an interesting question. I'm having two thoughts. One, is about sort of the marketing and, and you... It seems like your question was specifically about how that influences product. so I'm gonna give you a sort of tangential answer there. But, but with regard to the marketing, th-the critical error is to make... this is so obvious, it's marketing 101, but it's one of those things that bears constant repeating because we keep making the mistake. Your marketing is not about you. It's not about your company. Stop talking about you. Right? Just stop. Talk about your client. Talk about their problem, talk about their framing, what is urgent for them, how they're going to prioritize the implementation of solutions and, and if you're, if you're keying everything off that and making sure that you have a clear place in their, in their list of priorities based on their perspective, it's just so much more interesting. And I do think that that, you know, as I said ear-earlier, I, I think you'd be foolish not to incorporate that into, into product as well. When you're, when you're getting a consistent message from, from your hopeful end user, "No, this is the way we're thinking about the problem," and you're coming at it from a different angle, you're wrong. Now, there are truly, you know, like sui generis products like the iPhone that come along and revolutionize. No one knew that they needed that, right? So, so sometimes there are, there-- I think there are ideas that are so revolutionary that it may not be, it may not always make sense to ask your, your client what they're looking for. But I think nine times out of 10, in the B2B world specifically, your client has a better understanding of their problem than you do. so, so, you know, let that be your, your, your guide, and if you're convinced that you're wrong and you know more, have the goods

Have the goods. Bring the data. Oh my goodness, Joseph, this is like one of my favorite pieces of advice, right? Like, stop talking about what your product is made out of, and

Right

about how people are using it to make their days better. Like, you don't talk about like how you use an oven, you just talk about the delicious lasagna, right?

Exactly

the name of the show is The Tech Glow Up, and a glow up is a notable transformation. use it to talk about goals, like six month midterm kind of goals. In the work that you're doing or, you know, yeah, in the work that you're doing, what's the glow up that you're working on?

So I'm gonna talk first about the company I'm working for part-time, my fractional role, and then I'll talk, about, my more personal perspective, if that's okay. so with regard to the company, The Tech Glow Up is, we are using AI in a kind of revolutionary way. we view ourselves as, I'm gonna use an analogy. It's, it's something I'm testing out right now, so we're gonna see how it plays. But, you know, there's, there's a, a familiar problem with a lot of, of infrastructure, solutions called the last mile problem. You know, and this is true-- I think, I think people think of it a lot in terms of the telecommunications sphere, the last mile of copper or the last mile of fiber optic. Meaning you can do all of the work to build out a system, but then, you know, a good half of the work or more is that final 10%. It's getting, you know, from the last node of the infrastructure to the end user, to the individual home in the telecommunications context. And so we think of our product, we're using AI to fill in to become the last mile of revenue cycle management. Because we're in a phase-- we're facing a place in the healthcare industry right now where there's no more margin squeeze, right? you've done all of the operational efficiency things. you can project out exactly, you can have all the data points on exactly, what the cost per unit is gonna be for X medical unit and X initiative. But no RCM software, even though they can tell you exactly what your allowable billable is for any given procedure, they can't make Aetna pay you in two days instead of 60. and so the fact that hospitals have to go to-- when they go to loans or financing from banks, you know, they have all of these receivables that are from triple A-rated payers. The US government is the most reliable obligor in the world. And, particularly like rural and critical care access hospitals, the majority of their receivables do come from government payers, and they're viewed with the most skepticism when they go to a bank. And so any loan they secure has to go against their buildings and their medical de- like, their medical equipment, instead of this high quality collateral they have, these receivables from triple A-rated payers. S- And the reason for that is simple. It's because the banks can't package the risk. They can't quantify the risk for these receivables. There are too many unknowns. AI is able to give an actual, you know, greater than 95% accuracy valuation of any medical receivable, give you the early heads-up on whether it's going to, to be denied, whether there will be a delay in payment. so banks can loan against colla- against your collateral for the first time instead of going against your hospital's credit, right? So, so if we can close that last mile of revenue cycle management, then we truly do have a predictable revenue flow that people can model their future expansion plans, facilities upgrades, you know, if they wanna bring on an ambulatory care unit, they can, they can project all the financials with accuracy 'cause they know exactly when the money's coming in.

I totally, you jogged, the excitement I had from our initial conversation on this topic and how it, it's so silly, That, if there's, like, literally money that you could be, you know, taking loans against rather than, putting the b- putting a health system at risk,

Right

it makes so much more sense. and that the data then also isn't just protecting your investment, but helping you build a, a model and, for growth and expansion that's really kind of based on your actual receipts,

Yes

Like, it, it's, it's very, it's very

All we need to know, you have all this money coming in the door and the bank looks at it and says, "No, no, no, all that's junk." Because you can't tell exactly what, how much money it is and when it's coming in. And if you could do that, then it's suddenly collateral. So yeah.

oh goodness, Joseph, we are having such a good time. I think, You know what? Actually, I'm gonna ask this. As a, as an investor, as somebody who ha- has been, you know, sort of at the peak of, of an innovator's journey a, a few times, I've talked to enough, like, innovators on this show to know that, like, they're... Almost every founder or, you know, successful, entrepreneur has had a moment, where they were facing problems that felt insurmountable, and, you know, all it took to get them to the next level was, you know, a, a coach, a mentor, even a fan, you know, to share some advice, to say, "I believe you can do it. I'm curious, can you share a, a story of how, your guides or mentors have, helped you in finding the, the success and passion, for the work that you do?

I think, I've had, I've had a few different mentors. And I will say that, I've, I've been very explicit about going out and seeking. And sometimes these people, like, maybe they weren't even necessarily seeing themselves as a mentor to me, but I, I knew that they had some special juice and I wanted to like figure out a little bit more about what they're doing. So I've just found ways to spend time with those people. They, they may not view that as a formal mentor-mentee relationship, but I very much view them as people who have mentored me. I try to be more proactive about it in my own work when I, when I offer to mentor people. I, you know, I, I, I'm acknowledging that that's what I'm doing. I don't think necessarily that someone has to. I think, some of the best insights that I've gleaned have been from people who I just observed and watched. And I do ask them how they think about things. in the media space I worked with a wonderful guy named Bob Simmons. he just was-- he had been around the block and seen a lot of the same things that I was encountering in my work. And I think that by itself can be a really helpful... When you're feeling like you're facing an insurmountable problem, almost always someone has looked at a version of this problem before. Nothing is really that as new or unique as we think it is. And, and there's, you know, there might be a wrinkle, but but, but once you see, how similar the problems can be and how people have addressed it, it just, it's, it's that same, back to that same metaphor, you know. Eating an elephant happens one bite at a time. And any thorny problem, you just, you, you take the, the, the thread you can see, that you can understand how to pull, and you pull that thread, and then more will come out. I'm mixing my metaphors terribly but I think you're getting...

so beautiful.

Yeah.

I highly second that, right? Like, if there are people that you think you can learn from, reach out to them, you know, find ways that you can engage and, you know, be a positive, part of a, of a connection with them. it almost always is a really good idea to follow those instincts. Thank you so much. So it's time for the speed round.

Oh, good.

ready.

Oh my gosh, yeah. All righty. Sorry.

so, first question, and in a sentence or so, is there a key... If there was a key idea that people should take from our conversation today, what do you think it should be?

I think it's this, the one I started with, that, that the antidote to anxiety is action. Like, if you are worried about a problem, if you are feeling like it's insurmountable, the worst thing to do is to stand back and dread it. The, the, the more you can just... it sounds so obvious, but you just need to start, and that starting often just creates its own momentum

And even though you're, you totally have a one of a kind unicorn idea, other people might have looked at problems like this

Yes. exactly.

to start everything. I mean, it's, it's like the number one thing for startups, honestly, is like, you don't have to do everything from scratch. Somebody's probably done

Right

I'm a nerd about strategic planning,

Yeah

so I'm curious, right now we're basically right at the end of the second quarter of '26.

Mm-hmm.

your strategic brain focused now?

I never really finished my answer about my own personal tech look. so there's a part of my strategic plan that's focused on the things I'm doing. Right now I'm invested in eight startups. I started this relatively late. Really, I only began my career as an angel investor kind of by accident because I had these successful exits and I saw the power of it. I was like, "Oh, if I became intentional about this." so, so I'm I'm ramping up. I'm, I'm being judicious. You know, it's not just about numbers. So I'm deliberately going slowly and base, basing my decisions on the strength of those founder ideas. So, so that's my own, you know, kind of personal strategic plan, is I would like to invest in at least one more, in th-this calendar year. I'm already thinking about the problems of scale. Even though we're brand new and we are r- just rolling out our first pilot, I'm trying to, to be thoughtful about thinking about, okay, what happens when we suddenly have six clients and, and, you know, the, the constraints of the team are fine right now, but if all six of those clients had the same problem at the same time, how would we deal with that kind of thing? I think as much as I can trying to get ahead of thinking about the problems of scale, having done startups now a bunch of times, that's a real tricky sticking point. when you're transitioning from your first few loyal clients to kind of a scalable operation, that's when of the really hard stuff happens.

I'll take it. it's good advice no matter the percentage. Joseph, you kind of... I mean, that was kind of a spicy, soundbite or a hot take, but I'm curious, do you have a hot take about, health, climate, technology, culture or otherwise that you wanna share?

I am a tech optimist, and I think it's hard to be one right now. we're in a moment where we're seeing that some of the, most successful tech founders are not necessarily being 100% responsible. so I think this is a tricky moment to be a tech optimist, but I am. I think we can innovate our way out of our problems with regard to healthcare and climate, and we're going to

lastly, Joseph, how can people follow up to learn more, a- or connect with you, if they wanna learn more?

I hope they'll connect with me on LinkedIn. I'm Joseph Riddle at Capital Pulse on LinkedIn. I also write a Substack, Rebalance the World. if they wanna connect with me on a personal level, whether it's a founder with a great idea who wants some advice, or in particular, if you're in green tech and want an investor or an investor's perspective, yes, please reach out. I would love that

Amazing. Riddle of Capital Pulse. And, does your, have a firm name for your advising or your in- investing?

I'm loosely affiliated with, with a, an organization called Cold Spring Harbors, but it's mostly something I just do on my own. we're an informal collection

when we first connected, I was so excited about seven of the many things that you do, and I am so delighted that we could dive into many of them here on The Tech Glow Up. I feel like we might need to do a whole additional episode to really get into, tech optimism around climate. but I so appreciate, you know, the, the patient, the human, first perspective on how to make and develop great products and, some really sound advice about, hey, startup founders, you're working on big, important problems, but not every problem needs to start from zero. And there are books, there are frameworks, there are mentors, and many others along the way who can help you, level up way quicker, if you reach out, and, and build, you know, the right group of advisors. I feel like this was a masterclass in, innovation and, and a surprise, inspiration about healthcare revenue cycle management, which I'm always, tickled when I get excited about. So it's been such a pleasure to have you on The Tech Glow Up. Thanks for

Thank you so much. Take care, Nathan

Amazing. Boom