Strategies, Trust & Growth | Easy Health COO, Aaron Schiff (Podcast 201)

Podcast interview (Second in Command) with Aaron Schiff, COO and co‑founder of Easy Health, discussing his entrepreneurial background (founder of Matic), the COO vs CEO roles, hiring and scaling a remote company, fundraising, and Easy Health’s mission to combine Medicare insurance distribution and care. Covers company traction and growth (rapid hiring to ~300 employees, $135M raised), operational lessons (trust, delegation, recruiting), and recruiting/talent strategies.
Questions this video answers
$135 million
Anthemis Group and QED Investors (round included Victory Park Capital, Nationwide Ventures, Healthy Ventures, Brewer Lane and Operator Partners)
Matic; served as CEO from 2014 to 2018
Lives in Venice, California; dog named Maxwell (three‑year‑old German shepherd, adopted from a local shelter)
300+ employees
Chapters
To be a really good CEO, you have to be good at operations, you have to be good at basic company systems, right? That's the exact thing you don't want to do as a CEO. What I would suggest for anyone who wants to have the seat is to say, can you give up the control of being the one who decides how things are done and just start saying here's what I want to happen and have someone that they trust who they who is capable to execute on that. In the most basic form, I would say a CEO should learn how to see farther and a CEO should learn how to see a little closer.
Today is the Chief Operating Officer of Easy Health, Aaron Schiff. Easy Health is a company redesigning Medicare by connecting insurance distribution and care. The company has a simple purpose to help enroll and follow up with people eligible for Medicare to improve health outcomes. They currently have raised 135 million in equity and debt co led from Anthemis Group and QED Investors and included Victory Park Capital, Nationwide Ventures, Healthy Ventures, Brewer Lane and Operator Partners. Prior to this, Aaron founded Matic and served as a Chief executive officer from 2014 to 2018. Matic is a tech enabled insurance agency which simplifies purchasing homeowners insurance, allowing lenders to close loans faster and reduce origination costs. During his time he was recognized as the housing wire Rising Stars and currently resides as a board member. Aaron is a Southern California native growing up in Los Angeles, graduating from the University of Santa Barbara, lives in Venice, California with his three year old German shepherd Maxwell, who he adopted from the local shelter and is the true head of household. So Aaron, welcome to the Second in Command podcast. Hey, you're welcome. Good to see you. I'm actually really looking forward to diving in on this. So I'm going to ask you in a second about, about Easy Health, but I just want to get a little bit of kind of your background and what got you to where you are today. So you know, give us kind of the, the, the one or two minute helicopter tour of who Aaron Schiff is and how you got here.
You know, I never consider myself an entrepreneur even though I think inherently I was one. My first company out of college, I was trying to do every role possible. I would my last name Schiff. I would do what's called the Schiff Loop where I would go when I went to the bathrooms were in the middle and it was a circular office and so you could go all the way in the circle and talk to every single person. So I would go to the Batman on the way to the bathroom. I would literally talk to every single person, say, what did you do? You know, to show me what you, you know, show me your day to day. And it's funny. Everyone wants to talk about what they do. And so I, I learned a lot about the organization. I try to help everyone. And we could do this, we could do that. And I was just put in my box. And so I, and so, and so I ended up switching to a certain department, took a pay cut to do it because I wanted to learn more. And I said, hey, if I do well, you guys have to give me a raise. And they said, okay, deal. And so within a couple of months, I started making $4,000 in net new revenue and net new profit. Excuse me, for them a day. And this was after, this was right in 2008, 2009, crash. So they were like, oh, we're doing a hiring freeze. And I was like, I make what you guys promised me to raise in a day. Like it's not like, you know, I mean like it's not, it's, it's not a lot of money. It's easy. Exactly. And they, they didn't do it. And so from there I was like, okay, I can do this on my own. And that was really the genesis of my entrepreneurial journey. And then from there, you know, a couple failed projects and then, you know, my first real company was an ad network. We made $6,000 in our first three days. We made our first million in seven months. It was just me and a partner and we started doing a lot of revenue and a lot of profit. It was a life changing business for us. And I told myself I'd never be in debt ever again. Fast forward. A couple of years later, I bought my first house. And that led me into my next project, Matic, where my partner and I got together and we said, hey, why can't you buy home insurance at the point of sale? And because I almost lost my house. When I went to buy my house, I actually almost lost the deal because I didn't have home insurance. And so my partner on the other side was doing an audit on a lender and he found they were going to lose $30,000 a month because of home insurance loan delays caused by home insurance. And so we said, or he actually said to me, hey, why don't we integrate with lenders at the point of sale? And I was like, I didn't know you could integrate with a lender. Let's do it. So Matic is a really large fintech company. In the space. It's funny, in 2014 there wasn't such a thing as fintech, which is when we started it. And now it's big. And then I sold part of it in 2019, took a year off. Covid hit. I was bored out of my mind. I was on Wall street bets. Day trading before Wall street bets was a big thing. I was just bored. And then my now partner reached out to me and said he saw me on a podcast or something related to Matic and there's only so many insured tech entrepreneurs in la and so he reached out to me and he was explaining what he did and I was like, holy cow, I just built this business but for pnc and now you can do this in a completely different vertical, which is Medicare 65 and over. We help seniors figure out the best healthcare plan for them and make sure they utilize their benefits and with the goal of better health outcomes. And so he was explaining to me what he was doing. I was like, oh my gosh, I just built this business but this has 3 times bigger, better unit economics than 12x bigger market. So I was like, this is a no brainer. And that's how we got started with Matic.
Did you raise money there as well?
Yeah, so my first company was, was an ad network. We didn't raise a dime. Just to give you the difference in what's changed in 10 years. That was in 2011. We were doing a million dollars in revenue within, like I said, seven months and we couldn't get a $3 million valuation. On a note today those numbers would be, you know, we would have gotten a $50,100,000,000 valuation based off of the world that we live in today in the venture community. So that was actually really lucky. We didn't raise money. So the first one, we didn't Matic, we didn't raise venture dollars. And actually with Easy Health, I went to a lot of my old Matic investors. I was like, if you like Matic, you're going to like this. And then I think it's a good signal that a lot of the investors from my attic also invested in this. So.
So to start off, I mean, doing two companies in a row that were yours, what was it that then allowed you to shift gears and go into the CEO role?
Complete question.
Completely different role.
Yeah.
I know you're, you're also a co founder so like to kind of bracket it. Right.
But yeah, no, it's true. I mean my partner, David, CEO, I try to honor that Delta and not be you know, it's really easy for me to be like, I know what I'm doing. I'm the CEO. But I think a couple things. Number one, I was just really hungry to find something I wanted to work on. And so. So there's that. Number two, I. I have a. I'm just very fortunate to have a great partner. There's a lot that I can learn from him and have learned from him, and there's a lot he can learn from me. So I think it takes a special. I don't think I could do with just any partner. I think the one I have today is just a special type of person. And so we just work well together. So honestly, really lucky. And I would not have thought I could be a C. And one of my concerns was, I don't know if I don't. If I don't know how to be a CEO. Like, that's all I've ever known. And so, yeah, I think luck just being more mature than I. Than I was, you know, five years ago, and letting my ego on the side and saying, hey, I just want to win. And that's what David wants to do, too. We're just here to win.
So explain to us the differences of what a CEO and a COO are then, from your kind of lens, because you've done both. I mean, you can read about it, but what are the real differences from what you've seen playing in both roles, not from a textbook, but from an actual practical. You were there.
Yeah. One of the nice things is, and I think with why this has worked well for me, is that David has given me, like a CEO in a box role in a lot of senses. So there are certain things where I can just. There's a lot of autonomy. And so I still get that. At the same time, I still have the responsibilities of, you know, I'm a zero to one. David's a one to ten. So it's actually really nice for him to just be focusing on that. Let's get that 10x. So for me, what that means is you're focusing on the 10x, but we still have to execute on the tasks at hand. So it's really a lot more operations, it's a lot more granular, it's a lot more tying the vision into actual process and operations, which is really fun. But also, you know, sometimes the narrative has to be brought down, or at least the expectations have to have a certain a time, a realistic timeline. And as everyone, every good CEO knows, you know, there's a little Bit of, of emphasis on everything you say.
I'm curious. We are in the CEO alliance. This network that I run. We've got, you know, CEOs from 17 countries and not very many of them, I'd say maybe 5% have aspirations to ever be a CEO. They love being a second in command. They might want to do it for other companies, but they really have no desire to play in that seat. What do you think would allow for any of the COOs that maybe want to be a CEO? What do they have to do differently because you had to adapt to go from CEO to coo? What would they have to do to go from COO to CEO?
I think to be a really good CEO, you have to be. You have to be good at operations, you have to be good at basic company systems. Right. You're the person who eventually is responsible for something as simple as, hey, making sure employees get their computer on time, to HR problems, to specifically, where's rbi? And how do I even understand the basic metrics? So it's really such a wide gamut. And so you have to be really in the weeds. That's the exact thing you don't want to do as a CEO. So what I would suggest for anyone who wants to have the seat is to say, okay, can you give up the control of being the one who decides how things are done and just start saying, here's what I want to happen and have someone that they trust who they, who is capable to execute on that. And that is a very. And be able to say over and over again, is this the end goal that I'm trying to hit versus again, coo? You have to be a little more. You have to see a little closer in front of you versus a CEO. It just looks farther. So in the most basic form, I would say a COO should learn how to see farther and a COO should learn how to see a little closer. Yeah.
Do you think I'm a little bit too close to it to see something? But I'm curious whether I've always seen the CEO COO as the real yin and yang in the business and the other C levels as, as important, but a very different relationship to the CEO. C001. Am I missing something or do you think that's accurate?
It's certainly true in my experience. One, to be fair, but. Or actually, I guess three. But I think the reason for that. Well, those are also co founder rules. Right? I think CEOs are typically co founders for the most part. Yeah. So just a co founder is a different, you know, you're in the investor meetings, you're, you're doing all the same heavy lifting in terms of the partnership. So I think I would agree that it's relatively different relationship, for sure.
Yeah. Than the CTO or CFO or other kind of C level roles for sure. So I want you to just tell us again what Easy Health does in layman's terms, so everybody understands that. And then I want to get into some of the kind of specifics of how you got to where you are with the company today as well.
As you mentioned, we're the first company to combine insurance distribution and care. What does that mean? There are brokers, there are insurance distributors and there are providers. So you go to the doctor or you get a checkup from a nurse practitioner, things like that. And these health plans, these carriers work with both insurance brokerage distribution and providers care. And so these services already exist to for to help a senior. But no company has ever combined both. And so by doing that we fundamentally improve Medicare and remove the silos that exist today. Because the person you sign up with and you tell, you speak with for 30 minutes and you, and you tell them your clinical conditions, you tell them your drug history and all that and they work with you to figure out the best plan for you. As soon as your plan starts, they're done. And so all that information that you gave the broker is now lost and gets lost in translation. They don't give you any expectation of what you should do with your plan. Typically they don't even tell you how to use a lot of your benefits or they don't, or you don't know enough to do on your own. And so there's no help. And so by combining those to the insurance brokerage, the distribution and care, we create better health outcomes because we're helping the member throughout the journey. Easy health persists the senior, AKA the member throughout their journey of Medicare versus just stopping when the policy starts.
And are all. So is Medicare your entire market or do you go outside of the Medicare market then?
Just Medicare.
Just Medicare, yeah.
Which is a $800 billion market and expecting to double to 1.6 trillion by 2028.
You're really not doing very much at all. You haven't been quite successful at all. 135 million. Holy shit.
Paul's.
That's amazing. In like in a few years, it's.
This has been a rocket ship. I, I will say like I've never been at a company like this with this type of growth. It's Every day is a new challenge. And it's, it's funny. You, you know, I used to read about how when you, when you're in a rocket ship, it's, it's, you know, you have different types of problems. And I was like, well, those are like really good problems. You know, it's like, I have too much money, quote unquote is a problem. Not, not that that's my problem. I wish it was. But yeah, you know, it's one of those things that sound, that people frame as a problem. But you're like, that's not a problem. But it is like, I mean, when you grow really quickly, you have your own set of problems. I mean, the reality is the wings are falling off and you're duct taping them in the middle of the air. Right? You have all these things because you're moving so fast and you're getting so much scale so quickly. You know, hiring is challenging. Servicing your customers are challenging. Making sure things don't break is challenging. Making sure you're compliant, making sure that your employees are happy. I mean, it's just really, really hard. And it just gets harder at scale. Especially when to scale quickly. You fundamentally cannot build process quick enough. And so what that creates is chaos.
Now is this a rebrand of an existing company or did you, you really founded this 18 months ago and, and you've raised 135 million in 18 months?
Yeah, so my partner bought an insurance agency. So we got our license passers, but brand new company, brand new ownership. Like we, like, it was like a 10 person agency.
How many employees now?
300 plus.
300 plus in 18 months. So are you guys, what are you using that money for now? Is it to acquire talent? Like, are you going out and just buying the best senior team you can put together? Are you, is it marketing? What are you spending on tech?
Yes. So certainly our number one priority is smart people. We are where we are today because we've recruited incredible people. I mean, that's, I mean, if you want to have a great company, that's the easiest recipe for success. Especially when you're a market size as big as ours. Having really smart people who've done it before, not just smart, but who've done it before, is really helpful. And we've done a really strong, We've done really. I've never seen a company at our, at least before we raise all this money that had the team that we had. So that's one. And then, yeah, marketing. Yeah, basically marketing just growing faster. I mean, I Think the, the definition, you know, why you should, you should try to get venture dollars. The only reason is to pour gasoline on a fire. If you don't have product market fit, you're just creating a slog for yourself. But if you got product market fit, then the venture dollars, what it should be used for is, is the gasoline to throw in the fire. And that's how we look at it. So it's just essentially a rocket fuel for growth.
How much of it have you spent?
We've been pretty capital efficient. We have about 80% of what we have in the bank still.
What were the key roles? What were the first kind of three key roles, do you think? Or 15 key roles. Like was there or was there an area that you're like, that's the one we got to start?
Well, we're a tech company so you know, I mean we, we are, you know, again brokerage and, and care. But you know, our backbone is technology and I think so having a chief, so, so I would just say it's not necessarily the role, especially early, it's the type of person you have who can play multiple roles. So we have a lot of people on our, on our team who, who play multiple roles. Our chief Product officer, Greg used to be our cmo. So he could, he, you know, he could do to, to have someone who can be as, who can be a legit CMO and also be a legit cpo, is just a rare find. And the guy's brilliant. So we, you know, we got lucky with that going. Our VP of marketing today used to be our VP of operations. He can do both. He's brilliant, right? So we've just been really lucky to be able to get people who can do multiple roles and just, you know, especially to start, especially when you're growing, you need to get things done for yourself. No one's going to help you, certainly not our company, which makes it very challenging. You have to do it yourself. And so we've been really fortunate to find people who can, who can execute without needing, you know, tech resources or they, they, you know, they know SQL themselves or things like that. So I would say it's more about the role and being a versatile player, especially earlier and having smart people, that's.
How are you attracting them? Is, is there equity? Is there long term incentives? Well, is it just. You're paying them. Great.
So. Great question. I think there's, I think there's three things. The first thing is the story. We have a very clear mission of help, you know, better health Outcomes for seniors. There's not very many companies where you can truly help people and also get paid and have a significant amount of upside via equity. So I think the story is one, we do pay and we do give our employees. Every single employee gets equity. But I think the real truth of it is my partner, David, he's an incredible recruiter. I mean, he spent a lot of time recruiting great people. I mean, it is a time consuming. There is no hacks. It just takes hard work and knowing how to source and talk to people and just be a ruthless recruiter. And I don't mean ruthless in like a negative way. I mean just going after it all over and over. And you know, he's the best I've ever seen. And you know, we mentioned earlier, you know, how could I be a CEO? Like, I've learned so much from even just if I learn nothing else but how to recruit, that is the way. And I think typically it's a CEO doing it and that's part of their job. But a COO would be great at it too. Right? Especially for a co founder to really get smart people and bringing them in is one of the most undervalued, underspoken about skills that absolutely makes a company. You hear a lot of companies talking about they were good at raising money or they're good at telling stories or blah, blah, blah. Being a great recruiter is probably the most underrated and best thing you could do, especially early on.
Yeah, if you can't get that one, you'll never scale fast. You guys started this in the midst of COVID like right at the beginning of COVID too.
Yeah. So we had, we had bought an office in, in. In March and then everything shut down or not bought an office. We rented an office basin.
And so you didn't even, you really didn't start with an office, did you? You started, you had to start remote.
We started remote. You know, we were an essential service. So we got to use the office if we, if we wanted. But now no one, we have an office still. I think it's like five or six people go to it out of 300.
Really. So will you stay as a remote company, do you think?
Yeah, we have to. I mean, and that's really helped us. I mean, look, there's a lot of challenges with remote. I don't think anyone's cracked the culture code. We certainly haven't. It's really challenging. I mean, we have great culture, but it's not, you know, there's nothing that replaces being with Someone in real life. Yeah. But the pro is that we've been able to hire some incredible talent. And because of the talent, you know, what we do, Medicare is somewhat niche. Niche. And so to be able to find the best talent, no matter where you are, has been a huge win for us. We would never have been able to do what we've done if we just had a hire in Los Angeles.
I can't even imagine getting ready to start a company, having the office leased and then going, oh, shit, now what? So did that throw a wrench into plans at all, or were you just like, adapt, move fast? Like, we'll figure it out.
Yeah, I mean, just. You get stuck in the unknown, I think. Oh, it's just a different type of unknown than entrepreneurs used to. But it's just the same. Same sort of thing. You know, things get thrown at you all the time. It's definitely challenging. But again, I also, you know, again, we were essential workers, so we got to go back relatively quickly. So it also didn't affect us as. As much as it could have. I think it was just more about what's going on with the world that was probably a little bit harder, but everyone went through that. So I don't think our experience was any different.
Did you sell Ad Network or what did you do with the Ad Network that you built up?
Yeah, I sold it to my. I sold it to my partner at the time, which I didn't. That was a. That was a great. It's still a great business. And.
But in Matic, you sold to another, like an acquiring company or PE or.
Who did you sell to? Yeah, I sold a portion to some investors. Yeah.
Okay. So I want you to give us kind of the operational. Even though you were CEO at Matic, what kind of. Can you give us an operational lens that went well and that you could have done better on the sale of that company. And then I want to start talking about, you know, what it was like in raising money as well.
So on the sale of Matic, it was more of a. I think my partner and I at the time, we just wanted to go separate directions. And so that sale was more of a facilitation of that. It wasn't more of a traditional company sale. It was just part of my shares. So that I would say that my experience there is maybe not so helpful to the. To the general public or general public, to the general CEO of. Again, it was more of a. Let's figure out how to. How to move forward on this.
Let's talk about the raising money. Then in going through and raising money and working with so many different venture capital firms, what do you think are some of the lessons that you can impart from, from that journey?
So the first thing I would say is run a really solid process. And what does that mean? It means you'll get a lot of, if you're doing something right, you'll get a lot of inbound interest and you'll get a lot of people trying to have meetings with you. And you'll take those meetings, but you should not take those meetings. You should learn a process and you should have a CRM or a spreadsheet and be very methodical about what you're sending to them. Having different touch points. Okay, we had a pitch meeting. I sent them an investor memo, I sent them the data room, I sent them a case study, whatever it might be. And then that way you have those touch points. You know, you can color code red, green, blue, you know, red, yellow, green. Where are these people? And just be really focused on, on that contacting and trying to lay up as many investors as possible in the same day so you can also get your flow right. You have a great story. So I would say that having a great process is rule number one. Rule number two is having a great story. So investors are listening to your story. They either buy it or they don't. That's it. So a lot of people are like, well, do I have to have financials as the team slide at the beginning? Is it the end? None of that matters. It's just a story. And so your ability to tell that story and your ability to tell a compelling story and your ability to have an investor deuce themselves, the right answer versus you telling them is the difference between you winning and you losing. If I am, as an investor, can see this and say, I know how this wins without you telling me you're going to get money, if you can't do that, then you don't have a compelling story. It's not simple enough, it's not clear enough, super hard to do. Your first pitches are always going to suck. So at least, at least that's for us. Our first pitch is always absolutely terrible. So it's just practice.
And I don't know, the list was like six or seven companies that have invested. How many do you think you talk to?
It depends on which company. I mean, we had a fundraiser, matic, that lasted 912 months because we didn't have this process, which was absolutely brutal. And it actually ended up working out well for us. Because we end up getting more money than we had asked for originally. But still it was. It's not fun. It's very time consuming. In terms of easy health, it was a little bit easier. We probably spoke with 25 at the beginning and we got four or five, which was. We got a couple that four or five into the company and we had a couple that were interested but couldn't meet the valuations we wanted. That was really lucky. I think a lot of that was because of A, we had great traction and B, it's a lot easier when you're a known commodity. You know, I was talking to some of the same investors or I was talking to other investors who I had history with and they introduced me to somebody. So the second time around is always much easier for sure than the first time around.
Does that equate to the team that you're hiring as well? Like to hiring some of the people that have been through this before? Does that lend itself to working with some of these VCs too?
Like just a story, right? So I think it's a story. Having someone who has a credible company, who has built something credible makes it a lot easier for me as a VC to invest in you. So I think that, yeah. So if you, and so if you have someone in your team who looks very investable, that's why people strike any fang, right. I went to Yale, I went to Harvard, I went to wherever. People put that on there as a, as a social proof, it really does work. Oh, you made it to Harvard. You must be competent, right? It's the world to live in, right? So you, oh, you built a very large fintech organization. You must know how to run a company or you must have done something right. You know, even if you even. You sound like an idiot on the phone and you know, whatever. It's like that is a proof point that they cannot argue.
I would argue, I would argue that if they made it to Harvard, it's more than being competent. I know you're kidding, but the.
I said competent, not confident.
No, competent. Yeah, no, I know.
Oh yeah, Confident. Yeah, yeah, yeah, for sure.
They're like the best of the best. But you're right, it is proof. It is great social proof. So you said something that was interesting when you were first starting your career that I thought was intriguing. Tom Peters used to call it mbwa. It was management by walking around, but you were just kind of learning by walking around. Do you still do that today as a coo or when you're doing it, when you Were a CEO, do you spend time just walking around and talking to people and show me what you're.
Working on or favorite thing in the world to do? I don't do it as much anymore because we have five people in the office. But at Matic, we had a large Columbus, Ohio office. And I would get so energized. I loved walking around and just walking into people's offices and just bothering them and saying, what's going on? I would pour, you know, people working late, I would drink wine with them. And while doing stuff on the side, like, I would just do whatever I could to be involved and to seek because selfishly, just gives me energy. And I like. I like seeing the machine work. I'll never forget the first time I realized that Matic was going somewhere, was somebody walked past me. They said, you know, they said hi, and three people went to a conference room. And I had no idea what they were talking about. I had no idea what they were working on. And I was like, this is great. I love that. I love that I don't have to know and things are just getting done. That was. That was a big deal for me at the time.
That's kind of the 100 to 300 employees zone, right?
Yeah, yeah. Or even. Even. Even. Man, that's so long ago. Yeah, 50. Yeah, 50 to 100. Yeah, something like that.
What are you doing right now with the transitions you're in now, like at the 300 employee zone? Politics is coming in. I'm sure.
I mean, I'm sure it is. I just haven't felt it yet, you know, I'm sure it is. I just haven't felt it.
Do you think that your skills have to change and evolve now, or are you working on your skills in any area?
Yes, 100% has to change. The thing that's interesting is even though we're scaling so quickly. Well, the first thing is I'm just hiring as many smart people as I can to not do the things that if I'm doing it, it's probably not gonna be done as well as someone who's their one job or their. That's part of their main responsibilities. So certainly moving to delegation or not trying to be a hero, quote unquote, and just doing the work has been hard and challenging, especially when you want something done in a certain way. So, yeah, that learning how to trust somebody is very challenging. I learned that a lot in Matic, but it's still always hard to remember. And I think a lot of people don't understand what Trust is like most people think trust is. Once you trust someone else to do something in the way you want it to be done. That's not trust. Trust is when you let someone do it in the way that they would do, even if you would do it differently and you think your way is right and you let them do it their way. That is a really hard thing to do. Undervalued skill, something that I do well sometimes and not well other times. So I think that's probably the biggest thing in terms of skill set. And then just, you know, managing, managing a big team of people and getting culture and doing remote work and getting everyone to buy into the mission remotely is very challenging. So I'm still trying to figure out how to get good at that.
Where do you learn that stuff? From doing, from talking to others? Where do you go to learn or how do you learn?
Yeah, so like, groups like yourselves. I, I do, I, I do CEO groups. I've never done a CEO group, but that sounds great. There's other things. You know, the Internet is. Twitter is just an unbelievable resource. It's actually probably a better networking tool than LinkedIn as well. And just hearing from other entrepreneurs and hearing their stories and their pain, I mean, everyone. The interesting thing about where we are in the us Especially in terms of how strong we are as an entrepreneurial country, is there's so many entrepreneurs, which means that there are people who have had the same problem you have. Have had. And there's almost nothing new about the problem you've had. And so there's always someone who has done it. And so what I think that I could be better at too, is just finding that per try. And one thing that I've been really poor, done a poor job in the past, and something I've learned from David is never try to solve the problem yourself. Always try to find someone who's already solved that problem and talk to them and then talk to someone, solved it, and then triangulate, triangulate. And that is something that is just so much quicker than saying, oh, listen, I'm a smart guy. I can figure it out. Doesn't matter.
When I was 16, my dad said, you know, you'll never be smart enough to figure out all these business problems on your own, but your R and D should stand for rip off and duplicate. And he said, millions of companies have figured out everything that you'll ever try to do. Try to find out who they are and what they've done and just take the best ideas and run with them. They'll get you most of the way. And for me, that was always the shortcut. Right.
So by the way, that relates to hiring great people who've done it before because they'll know those shortcuts because they've already done it. They've already gone through the pain of learning the things that you know will slow you down. And I think that's another difference that between Matic and Easy Health. And one of the reasons why we move so much quicker is because we all had the benefit of having other startups where we learned from and getting other people who had already built what we wanted to build and saying, hey, let's not find smart people, let's find smart people who've done it before.
How did you divide your roles between you and the CEO now? How did you guys decide who was going to do what?
Yeah, I think just we basically said very early that I'll be 0 to 1 and you'd be 1 to 10 and so you don't get in the weeds and I won't. And I'll. And I'll just follow your strategy. And we kind of. Do we actually do that all the time? No, but that is the, that is how we, how we've tried to, to, to divvy up the business. And I will say it's been, it's been pretty effective for the most part.
I want to talk about that whole. Go back to that NBWA again. You said it's kind of one of your favorite things to do. How do you wander around the office and talk to people when it's virtual?
That's the challenge that I haven't been able to do that as much. I mean, I do it with the five people who I work with today. But, you know, sometimes what you do is you just call someone, you know, send them a, a Slack video request and see if they pick up. You know, it's just not the, it's not the same, honestly, because people can decline. People might be in a meeting, you know, you can see when people are busy. So you don't mess, you know, you don't bother them. So it's just. I haven't figured out the good way to. A good way to do that. And it's, it's tough because it's not. It's not. That's really my most fun thing to do.
Well, I think, I think so. It's interesting. I'm sitting here thinking about how would I do it? And then you just mentioned it earlier. Our job isn't to figure out how to do it, it's to find the people that are doing it. I think you and I need to find the people that are doing it because somebody out there, or more than one are, are doing it in a good way. Because I think we need to find that. Because that was a huge thing for me as well. And I think it's a, I think it's a big opportunity when, I think when companies can crack that code, that's going to be big for them. All right, I want to go Back to the 22 year old Aaron, graduating from college, getting ready to start off on your career. What advice would you give the 21, 22 year old that you maybe you know it to be true today, but you wish you'd known back then.
Read more, listen more, talk less. And also I would say, you know, be, you know, I got to where I was. You know, I think, I think just like comedians typically, they always say, oh, there's some like darkness to them. I don't think I have that darkness. But I do think there's like a chip on my shoulder that I, that I have. And so that that chip is both good and bad. And so I would say just to not come, like, take it a little easy on myself now. It's easy for me to say that now, but at the time it was, you know, you got that pain drove me. So I would try to see if I get to the same place without the pain being the engine or the fuel more of just like a place of strength and like love versus like just, you know, anxiety.
Aaron Schiff, the CEO co founder of Easy Health, thanks so much for joining us today on the Second in Command podcast. Really appreciate the share today.
Thanks Cameron. Thanks for having me.
My driver has been sort of being that savior, you know, having that savior complex, really helping people who need the help, that underdog. I want to go in as soon as I hear that they're not doing well and sometimes that's not the right thing to do when it comes to your team. Sometimes they need to figure things out. Being there and doing everything for them is not necessarily the best solution.
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