Ep. 201 – Easy Health COO, Aaron Schiff

Our guest today is the Chief Operating Officer of EasyHealth, Aaron Schiff.

EasyHealth 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, Aaron founded Matic and served as the Chief Executive Officer from 2014-2018. 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 a HousingWire Rising Stars and currently resides as a board member.

Aaron is a Southern California native, growing up in Los Angeles and graduating from the University Santa Barbara. He lives in Venice, California with his 3-year-old German Shepherd, Maxwell, who he adopted from the local shelter and is the true head of household.


In This Conversation We Discuss:

  • What COOs must do to adapt as a CEO 
  • How Aaron took the company from 10 employees to over 300 in 18 months 
  • How crafting your unique story attract the right investors 
  • Handling rapid growth of your company 


Connect with Aaron Schiff: LinkedIn 

EasyHealth – https://www.joineasyhealth.com


Connect with Cameron: Website | LinkedIn

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Our guest for this episode 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 by 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 the 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 HousingWire rising star and resides as a board member. Aaron is a Southern California native. He grew up in Los Angeles and graduated from the University of Santa Barbara. He lives in Venice, California with his three-year-old German Shepherd, Maxwell, whom he adopted from the local shelter, and is the true head of the household. Aaron, welcome to Second in Command.

Thanks for having me, Cameron.

You’re welcome. Good to see you. I’m looking forward to diving in on this. I’m going to ask you in a second about Easy Health but I want to get a little bit of your background and what got you to where you are now. Give us the one or two-minute helicopter tour of who Aaron Schiff is and how you got here.

I never considered myself an entrepreneur, even though I think inherently I was one. At my first company out of college, I was trying to do every role possible. My last name is Schiff, I would do what’s called the Schiff Loop where I went to the bathrooms. It was in the middle and it was a circular office. You could go all the way in the circle and talk to every single person. On the way to the bathroom, I would talk to every single person and say, “What did you do? Show me your day-to-day.”

It’s funny, everyone wants to talk about what they do. I learned a lot about the organization and I was trying to help everyone, “We could do this and we could do that.” I was just put in my box. I ended up switching to a certain department and took a pay cut to do it because I wanted to learn more. I said, “If I do well, you have to give me a raise.” They said, “Deal.” Within a couple of months, I started making $4,000 in net new profit for them a day.

This was right in the 2008-2009 crash. They were like, “We’re doing a hiring freeze.” I was like, “I make what you guys promised me to raise in a day. It’s not a lot of money. It’s easy,” and they didn’t do it. From there, I was like, “I can do this on my own.” That was the genesis of my entrepreneurial journey. From there, a couple of failed projects then 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 me and a partner.

We started doing a lot of revenue and a lot of profit. It was a life-changing business for us. 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 to my next project, Matic, where my partner and I got together. We said, “Why can’t you buy home insurance at the point of sale?” When I went to buy my house, I almost lost the deal because I didn’t have home insurance.

My partner on the other side was doing an audit on a lender and he found that we’re going to lose $30,000 a month because of loan delays caused by home insurance. He said to me, “Why don’t we integrate with lenders at the point of sale?” I was like, “I didn’t know you could integrate with a lender. Let’s do it.”

Matic is a 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. I sold part of it in 2019, took a year off, and COVID hit. I was bored out of my mind. I was on Wallstreetbets day trading before Wallstreetbets was a big thing. I was bored, then my now partner reached out to me and said he saw me on a podcast or something related to Matic.

There are only so many insured tech entrepreneurs in LA. He reached out to me and he was explaining what he did. I was like, “I built this business for PNC.” 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 with the goal of better health outcomes. He was explaining to me what he was doing. I was like, “I built this business but this has 3X better economics than 12X bigger market. This is a no-brainer.” That’s how we got started. I know that has been more than one or two minutes.

I’ve got a bunch of questions that even come off of that. With Matic, did you raise money there as well?

My first company was an ad network. We didn’t raise a dime. Just to give you the difference in what’s changed in ten years, that was about 2011, we were doing $1 million in revenue within seven months. We couldn’t get a $3 million valuation on a note. Now, we would have gotten a $50 million to $100 million valuation based on the world that we live in now in the venture community. That was lucky. We didn’t raise money. The first one we didn’t. Matic, we didn’t raise venture dollars. With Easy Health, I went to a lot of my old Matic investors and was like, “If you like Matic, you’re going to like this.” I think it’s a good signal that a lot of the investors from Matic also invested in this.

To start off, doing two companies in a row that were yours, what was it that then allowed you to shift gears and go into the COO role? It’s a completely different role and you’re also a co-founder, so I would like to bracket it.

It’s true. My partner, David, the CEO. I try to honor that delta. It’s easy for me to be like, “I know what I’m doing. I’m the CEO,” but a couple of things. Number one, I was hungry to find something I wanted to work on, so there’s that. Number two, I’m 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 that he can learn from me. I don’t think I could do it with any partner. The one I have now is a special type of person.

We work well together. Honestly, I was very lucky. I would not have thought I could be a CEO. One of my concerns was if I don’t know how to be a CEO. That’s all I’ve ever known. I think luck, just being more mature than I was five years ago and letting my ego on the side and saying, “I just want to win.” That’s what David wants to do. We’re here to win.

Explain to us the differences between what a CEO and a COO are then from your lens because you’ve done both. 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.

One of the nice things, and why this has worked well for me, is that David has given me a CEO-in-a-box role in a lot of sense. There are certain things where there’s a lot of autonomy. I still get that. At the same time, I still have the responsibilities. I’m a 0 to 1. David’s a 1 to 10. It’s nice for him to be focusing on that, “Let’s get that 10X.” For me, what that means is you’re focusing on the 10X but we still have to execute the tasks at hand.

It’s a lot more operations. It’s a lot more granular. It’s a lot more tying the vision into actual processes and operations, which is fun. Also, sometimes the narrative has to be brought down or at least the expectations have to have a certain realistic timeline. As every good CEO knows, there’s a little bit of emphasis on everything you say.

I’m going to ask about that in a second as well, I’m curious. In the CEO Alliance, this network that I run, we’ve got COOs from seventeen countries. Not very many of them, 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 have no desire to play in that seat. For any of the COOs that maybe want to be a CEO, what do they have to do differently? You had to adapt to go from CEO to COO. What would they have to do to go from COO to CEO?

To be a good COO, you have to be good at operations. You have to be good at basic company systems. You’re the person who eventually is responsible for something as simple as making sure employees get the computer on time, to HR problems, to specifically, where’s our BI and how do I even understand the basic metrics? It’s such a wide gamut, so you have to be in the weeds. 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?” Also, start saying, “Here’s what I want to happen,” and have someone that they trust who is capable to execute on that, and be able to say over and over again, “Is this the end goal that I’m trying to hit?” The COO has to see a little closer in front of you versus the CEO, it looks farther. In the most basic form, a COO should learn how to see farther and a CEO should learn how to see a little closer.

Do you think I’m a little bit too close to it to see something? I’m curious whether I’ve always seen the CEO or COO as the real yin and yang in the business, and the other C levels as important but a very different relationship to the CEO and COO. Am I missing something or do you think that’s accurate?

It’s certainly true. In my experience of one or three to be fair. Those are also cofounder rules. I think COOs are typically cofounders for the most part. A cofounder is different. You’re in the investor meetings. You’re doing all the same heavy lifting in terms of the partnership. I would agree that it’s a different relationship for sure.

Also, the CTO or CFO or other C-level roles for sure. I want you to tell us again what Easy Health does in layman’s terms so everybody understands that. I want to get into some of the specifics of how you got to where you are with the company now as well.

We’re the first company to combine insurance distribution and care. What does that mean? There are brokers, insurance distributors, and providers. You go to the doctor or you get a checkup from a nurse practitioner and things like that. These health plans and these carriers work with insurance brokerage, distribution, and provider care.

These services already exist to help a senior but no company has ever combined both. By doing that, we fundamentally improve Medicare and remove the silos that exist today because the person you sign up with and you speak with for 30 minutes and you tell them your clinical conditions, 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.

All that information that you gave the broker is now lost and gets lost in translation. They don’t give you any expectations of what you should do with your plan. Typically, they don’t even tell you how to use a lot of your benefits or you don’t know enough to do on your own, so there’s no help. By combining those two, the insurance brokerage and 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 stopping when the policy starts.

Is Medicare your entire market or do you go outside of the Medicare market then?

Just Medicare, which is a $800 billion market and expecting to double to $1.6 trillion by 2028.

One of our members of the CEO Alliance is with a group called Redirect Health but I think they’re in a different space than you guys are playing in. You’re not doing very much at all. You haven’t been quite successful at all, with $135 million in a few years. That’s amazing.

This has been a rocket ship. I’ve never been to a company like this with this type of growth. Every day is a new challenge. It’s funny, I used to read about how when you’re in a rocket ship, you have different types of problems. I was like, “Those are good problems.” It’s like, “I have too much money” is a problem.” Not that that’s my problem. I wish it was but it’s one of those things that people frame as a problem but you’re like, “That’s not a problem,” but it is.

When you grow quickly, you have your own set of problems. The reality is the wings are falling off and you’re duct-taping them in the middle of the air. You have all of these things because you’re moving so fast and you’re getting so much scale so quickly. Hiring, servicing your customers, making sure things don’t break, making sure you’re compliant, or making sure that your employees are happy is challenging. It’s hard and it gets harder at scale, especially to scale quickly. You fundamentally cannot build the process quickly enough. What that creates is chaos.

SIC 201 | Easy Health

Easy Health: When you grow quickly, you have your own set of problems. The reality is the wings are falling off, and you’re duct-taping them in the middle of the air.


Is this a rebrand of an existing company or did you founded this eighteen months ago and you’ve raised $135 million?

My partner bought an insurance agency. We got our license but a brand-new company and brand-new ownership. It was a ten-person agency.

How many employees now?

300 plus.

Three hundred plus in eighteen months. What are you using that money for now? Is it to acquire talent? Are you going out and buying the best senior team you can put together? Is it marketing? What are you spending on, tech?

Certainly, our number one priority is smart people. We are where we are now because we’ve recruited incredible people. 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 smart people who’ve done it before, not just smart, is helpful. I’ve never seen a company, at least before we raised all this money, that had the team that we had. That’s one, and then marketing.

Marketing is growing faster. I think that the definition of why 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 creating a slog for yourself. If you’ve got product market fit, then what venture dollars should be used for is as gasoline thrown in the fire. That’s how we look at it. It’s essentially rocket fuel for growth.

SIC 201 | Easy Health

Easy Health: If you don’t have product market fit, you’re creating a slog for yourself. If you’ve got product market fit, then venture dollars, what it should be used for is the gasoline to throw in the fire. It’s essentially 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.

You mentioned some of the problems. I’m rocking because I’ve built so many fast growth companies but this one is really fast with bringing on that much cash. What were the first three key roles do you think of fifteen key roles? Was there an area that you’re like, “That’s the one we got to start?”

We’re a tech company. We’re brokerage and care but our backbone is technology. It’s not necessarily the role, especially early. It’s the type of person you have who can play multiple roles. We have a lot of people on our team who’ve played multiple roles. Our chief product officer, Greg, used to be our CMO. To have someone who can be a legit CMO and also be a legit CPO is a rare find, and the guy is brilliant. We got lucky with that.

Our VP of marketing now used to be our VP of operations. He can do both. He’s brilliant. We’ve been lucky to be able to get people who can do multiple roles, especially when you’re growing. You need to get things done for yourself. No one is going to help you. Certainly not our company, which makes it very challenging. You have to do it yourself. We’ve been fortunate to find people who can execute without needing tech resources or they know SQL themselves or things like that. It’s more about the role of being a versatile player, especially earlier, and having smart people. That’s helpful.

How are you attracting them? Is there equity? Are there long-term incentives as well? Is it just you’re paying them great?

There are three things. The first thing is the story. We have a very clear mission of better health outcomes for seniors. There are not very many companies where you can truly help people and also get paid and have a significant amount outside the equity. The story is one. We do pay and every single employee gets equity. The real truth of it is my partner, David, is an incredible recruiter. He spends a lot of time recruiting great people.

It is time-consuming. There are no hacks. It takes hard work and knowing how to source and talk to people and be a ruthless recruiter. I don’t mean ruthless in a negative way. Ruthless as in going after it over and over. He’s the best I’ve ever seen. As we mentioned earlier, how could I be a CEO? I’ve learned so much about how to recruit. That is the way.

Typically, it’s a CEO doing it and that’s part of their job, but a CEO would be great at it too, especially for a cofounder. Getting smart people and bringing them in is one of the most undervalued and under-spoken about skills that makes a better company. You hear a lot of companies talk about raising money or being good at telling stories. Being a great recruiter is probably the most underrated and best thing you could do, especially early on.

If you can’t get that one, you’ll never scale fast. You started this in the midst of COVID and right at the beginning of COVID too.

We rented an office in March, then everything shut down.

You didn’t start with an office. You had to start remotely.

We were an essential service, so we got to use the office if we wanted. Now, we have an office still. I think 5 or 6 people out of 300 go to it.

Will you stay as a remote company, do you think?

We have to and that has helped us. There are a lot of challenges with remote. I don’t think anyone has cracked the culture code. We certainly haven’t. We have a great culture but there’s nothing that replaces being with someone in real life. The pro is that we’ve been able to hire some incredible talent. Because of the talent, what we do in Medicare is somewhat niche. 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 had our hire in Los Angeles, which is where our headquarters are.

I can’t even imagine getting ready to start a company, having the office leased then going, “Now what?” Did that throw a wrench into plans at all or were you like, “Adapt, move fast, and we’ll figure it out?”

You get stuck in the unknown. COVID is a different type of unknown than entrepreneurs are not used to but it’s the same thing. Things get thrown all the time. It’s challenging but we’re essential workers, so we got to go back relatively quickly. It also didn’t affect us as much as it could have. It was more about what’s going on with the world. That was probably a little bit harder but everyone went through that. I don’t think our experience was any different.

Did you sell the ad network? What did you do with the ad network that you built up?

I sold it to my partner at the time. I wish I didn’t. It’s still a great business.

Matic, you sold to an acquiring company or PE? Who did you sell it to?

I sold a portion to some investors.

I want you to give us the operational, even though you were CEO at Matic. Can you give us an operational lens that went well and that you could have done better on the sale of that company? I want to start talking about what it was like raising money as well.

On the sale of Matic, my partner and I at the time wanted to go in separate directions. That sale was more of a facilitation of that. It wasn’t more of a traditional company sale. It was part of my shares. My experience there is maybe not so helpful to the general COO group. It was more of, “Let’s figure out how to move forward on this.” That had a financial great outcome for me.

Let’s talk about 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 that journey?

There are so many. The first thing I would say is to run a solid process. What does that mean? It means if you’re doing something right, you’ll get a lot of inbound interest. 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 run a process and have a CRM or a spreadsheet, be very methodical about what you’re sending to them, and have different touch points. We had a pitch meeting. I sent them an investor memo. I sent them the data room. I sent them a case study. I sent them a case study or whatever it might be.

That way, you have those touchpoints. You can color code, red, yellow, and green, where are these people, and be focused on that contacting and trying to lay up as many investors as possible on the same day. You can also get your flow right and you have a great story. Having a great process is rule number one. Rule number two is having a great story. Investors are listening to your story. They either buy it or they don’t. That’s it.

SIC 201 | Easy Health

Easy Health: Have a great story. Investors are listening to your story. They either buy it or they don’t.


A lot of people were like, “Do I have to have financials? Are the teams at the beginning? Is it the end?” None of that matters. It’s just a story. Your ability to tell that story, your ability to tell a compelling story, and your ability to have an investor deduce themselves the right answer versus you telling them is the difference between you winning and you losing.

If I am an investor and I 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. It’s super hard to do. Your first pitches are always going to suck. At least that’s for us. Our first pitch is always terrible. It’s just practice.

If the list was 6 or 7 companies that have invested, how many do you think you talk to?

It depends on which company. We had a fundraiser at Matic. In the last 9 or 12 months, we didn’t have this process, which was brutal. It ended up working out well for us because we ended up getting more money than we had asked for originally, but it was 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. We got 4 or 5. We had a couple that were interested but couldn’t meet the valuations we wanted.

That was lucky. A lot of that was because we had great traction, and it’s a lot easier when you’re a known commodity. I was talking to some of the same investors or other investors who I had a history with and they introduced me to somebody. 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 you’re hiring some of the people that have been through this before? Does that lend itself to working with some of these VCs too?

I think it’s a story. Having someone who has a credible company who has built something incredible, makes it a lot easier for me as a VC to invest in you. If you have someone on your team who looks very investable, that’s why people strike anything, “I went to Yale, Harvard” or wherever. People put that on there as social proof that it does work, “You made it to Harvard? You must be competent.” It’s the world we live in. “You built a very large fintech organization? You must know how to run a company or you must have done something right” Even if you sound like an idiot on the phone or whatever, that is a proof point that they cannot argue.

I would argue that if they made it to Harvard, it’s more than being competent. I know you’re kidding.

I said competent, not confident.

I know. They’re the best of the best. You’re right. It is great social proof. 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 learning by walking around. Do you still do that today as a COO? When you’re doing it when you were a CEO, do you spend time walking around and talking to people and “Show me what you’re working on?”

It’s my favorite thing in the world to do. I don’t do as much anymore because we have five people in the office. At Matic, we had a large Columbus, Ohio office and I would get so energized. I loved walking around and walking into people’s offices and bothering them and saying, “What’s going on?” People working late, I would drink wine with them while doing stuff on the side. I would do whatever I could to be involved and to see. Selfishly, it gives me energy and I like seeing the machine work.

I’ll never forget the first time I realized that Matic was going somewhere. Somebody walked past me and they said hi. 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 getting done. That was a big deal for me at the time.

That’s 100 to 300 employees, right?

Yeah, something like that.

I remember that when we were building 1-800-GOT-JUNK?, there was somebody in the office elevator and we were going up. He started chatting and he said something, then we got off the elevator. He came up to me later and he’s like, “I’m so sorry. I didn’t know you were a CEO.” I’m like, “Dude, relaxed. It doesn’t matter. We’re good.” He goes, “No, but the company is so big now.” I’m like, “You’ve only been here for three days. How do you know that?” “I spoke to your class. I talked to the class coming in.” It’s a strange transition to go through. What are you doing with the transitions you’re in now? At the 300-employee zone, politics is coming in, I’m sure or is it?

I’m sure it is. I just haven’t felt it yet.

Do you think that your skills have to change and evolve now? Are you working on your skills in any area?

Yes, 100% it has to change. The thing that’s interesting is even though we’re scaling so quickly, the first thing is I’m hiring as many smart people as I can to not do the things. If I’m doing it, it’s probably not going to be done as well as someone who’s their one job or that’s part of their main responsibilities. Certainly, moving to delegation or not trying to be a “hero” and doing the work has been hard and challenging, especially when you want something done in a certain way.

Learning how to trust somebody is very challenging. I learned about that a lot in Matic but it’s still always hard to remember. A lot of people don’t understand what trust is. Most people think trust is when 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 it, even if you would do it differently. You think your way is right and you let them do it their way.

That is a hard thing to do. Undervalued skill is something that I do well sometimes and not well other times. That’s probably the biggest thing in terms of skillset, then just 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. I’m still trying to figure out how to get good at that.

Where do you learn that stuff? Is it from doing or from talking to others? Where do you go to learn or how do you learn?

Groups like yourselves. I’ve never done a CEO group but that sounds great. There are other things. Twitter is an unbelievable resource. It’s probably a better networking tool than LinkedIn as well, and hearing from other entrepreneurs, hearing their stories and their pain. The interesting thing about where we are in the US, especially in terms of how strong we are as an entrepreneurial country, is there are so many entrepreneurs, which means that there are people who have had the same problem you have and have had.

There’s almost nothing new about the problem you’ve had. There’s always someone who has done it. What I think that I could be better at too is finding that. One thing that I’ve done a poor job in the past and something I’ve learned from David is to never try to solve the problem yourself. Always try to find someone who has already solved that problem and talk to them, then talk to someone else to solve it, and then triangulate. That is something that is so much quicker than saying, “I’m a smart guy. I can figure it out.” It doesn’t matter.

My dad told me that when I was sixteen because I wasn’t the smart guy. I wouldn’t have been allowed on Harvard’s campus, let alone walk around it. They probably would have banned me. When I was sixteen, my dad said, “You’ll never be smart enough to figure out all these business problems on your own but your R&D should stand for rip-off and duplicate.” 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 take the best ideas and run with them. They’ll get you most of the way.” For me, that was always the shortcut.

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 will slow them down. That’s another difference between Matic and Easy Health. One of the reasons why we moved so much quicker is because we all had the benefit of having other startups which we learned from, and getting other people who had already built what we wanted to build and saying, “Let’s not find smart people. Let’s find smart people who had done it before.”

I like that you were saying that when you’re looking for talents. The only reason I was ever in Columbus, Ohio, which is where you built Matic, was I was there to learn. I was in the auto body industry years ago. We built a group called Gerber Collision in the US and it was Boyd Autobody in Canada. We went down to Columbus to learn from a guy named Bob Juniper who ran Three-C Body. Did you ever hear of Three-C Collision or Three-C Body in Columbus?

He used to have these advertisements that were like icy pink, and he was always against the insurance industry. He ran million-dollar ad campaigns against the insurance companies of how they were scamming people. We went down to learn from him. He was open arms, willing to teach us everything that he was doing. Is that how you’re using Twitter on the networking side just reaching out and saying, “What have you done?” How are you using Twitter?

It’s either that or you follow people. There are some people who give some great advice. It’s not rocket science. Sometimes, it needs someone to tell you. One was, after every call or after every meeting, the format is we’ll break them down and we’ll summarize it and action items and all that fun stuff. We’ll send it out every single time after the meeting. It’s super simple, super easy, and incredibly effective. Things like that are how you can stay fresh with new things. Going back to the skill question, another way you can learn is to have your employees tell you what you suck at. If you have a good cultural relationship, they’ll happily tell you.

SIC 201 | Easy Health

Easy Health: One way you can learn how to improve is to have your employees tell you what you suck at. If you have a good cultural relationship, they’ll happily tell you.


They’ll happily tell you for sure. How did you divide your roles between you and the CEO now? How did you guys decide who was going to do what?

We basically said very early that I’ll be 0 to 1 and you’d be 1 to 10, so you don’t get in the weeds and I’ll just follow your strategy. Do we do that all the time? No, but that is how we’ve tried to divvy up the business. It has been pretty effective for the most part.

Go back to MBWA, you said it’s one of your favorite things to do. How do you wander around the office and talk to people when it’s virtual? What do you do?

That’s the challenge. I haven’t been able to do as much. I do it with the five people who I work with now. Sometimes what you do is you call someone. You’ll send them a Slack video request and see if they pick up. It’s not the same because people can decline. People might be in a meeting. You could see when people are busy, so you don’t bother them. I haven’t figured out a good way to do that and it’s tough. That’s my most fun thing to do.

I’m sitting here thinking about, how would I do it then you mentioned it earlier, our job isn’t to figure out how to do it. It’s to find the people that are doing it. You and I need to find the people that are doing it because somebody out there or more than one is doing it in a good way because we need to find that. That was a huge thing for me as well and it’s a big opportunity. When companies can crack that code, that’s going to be big for them.

I haven’t seen anyone do it. If you find that person or if I find that person, we’ll let each other know and we should look because I agree with you. I’m more pessimistic that someone has cracked that code. I don’t know how you replace seeing someone in real life.

I’m going to do a couple of videos and post them and ask because there’s got to be some people out there that are doing it. I want to go back to the 22-year-old Aaron, graduating from college, and getting ready to start off on your career. What advice would you give the 21 or 22-year-old that maybe you know to be true today but you wish you’d known back then?

Read more, listen more, and talk less. Also, I got to where I was. I think like comedians. They always say there’s some darkness to them. I don’t think I have that darkness but I do think there’s a chip on my shoulder that I have. That chip is both good and bad. Take it a little easy on myself. It’s easy for me to say that now but at the time it was, that pain drove me. I would try to see if I could get to the same place without the pain being the engine or the fuel, but more of a place of strength and love versus anxiety.

Aaron Schiff, the COO and co-founder of Easy Health. Thanks so much for joining us on the Second in Command. I appreciate your sharing.

Thanks, Cameron. Thanks for having me.


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