Rezilient Summit 2025 Jim McKelvey Fireside

At our 2025 Inaugural Healthcare Summit in St. Louis in early August, Danish Nagda, Rezilient CEO and Co-Founder, and Jeff Gamble, Rezilient COO and Co-Founder, were joined by Jim McKelvey, Founder of Square,to discuss his philospohy toward investing and growing disruptive companies.

In case you missed our Summit, catch the whole discussion on the video below and in the transcript.

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Danish Nagda

One of the funniest things about Jim is how we met. I'm going to tell a quick story and then I want to hear his point of view on it because I've never asked him his point of view publicly, I swear it's not prepped.

Doug Ballard, who is a professor at WashU, Jeff and I sometimes speak in his class, he was like, hey, you should go meet Jim McKelvey.

I was like, that sounds great. He said he would write him an email. Jim responded to that email and said, hey, I'm going to be at this event at the botanical gardens tonight. They're giving me some type of award, so I'm just going to be standing by the wall. It's gonna be boring.

So I looked up the event. It was a black tie event. So I got in a tux and I showed up at the event.

I was like, hey, I'm here to see Jim McKelvey. And the lady at the front door says, everyone's here to see Jim McKelvey. And I was like, I know, I know, but he wants to see me as well.

And she's like, do you have any proof? So I showed the email where he said, come meet me here. And she was like, you could have just made up that email. I have no proof of this. Can you have him send a text message or just tell the CEO of this event? Hey, these, these guys are coming to see me. So I emailed Jim, no response. I sit in the car for two hours, no response.

He then sends me an email, 9.30, 10, probably after the event saying, Hey, sorry, I missed you. Why don't you and Jeff fly over to New York? I'll host you at Square headquarters. Me and Jeff were like, oh, this is going to be great. We're going to meet the founder of Square at Square headquarters in New York. This is going to be the coolest experience.

It's on Tuesday. Jeff and I get the tickets. We're about to go to New York on Monday night.

I get an email from Jim saying, I'm going to be in San Francisco. And I'm going to be here from 8am to 11am. You have 20 minutes. Just come by anytime.  

So after I calmed Jeff down, surprising, I know, but I calmed Jeff down, we showed up the next morning. We get to the front of the building and it's a WashU building, but there's no doors that you can get in easily, it's card access only. So I emailed Jim again, an hour goes by, no response.

I'm like, this is not going to happen again. There was a handyman walking by. I was like, Hey, do you have a key to this building? He's like, I have a key to all the buildings. I'm a handyman. He's like, who are you here to see? I was like, here, I'm here to see Jim McKelvey. So he gave me a funny look and I was like, he's on the second floor. You can just go.

There's no way I can know that without that. Just go and ask him if he wants to meet me. So we go up, he goes up, he asked Jim, Jim comes down to the door and doesn't say much.

He says, come here. So we walked behind him and we're shuffling through the hallway. We get to a room and there's one big chair like this and two high chairs.

And Jeff and I sit down at the high chairs. He's sitting at the big chair, kind of sitting down. He's like, all right, what can I do for you gentlemen? And then we pitch.

And at the end of it, he says, I'm so sorry, but this is my process. Most people don't make it this far. And I remember thinking to myself, he's probably right. No one's so crazy. What were you thinking?

Jim McKelvey

A lot of people pretend to want to meet me when, in fact, they just want to meet my wallet. I have probably, I don't even know how many because I've set up all these barriers, but it's dozens a week.

So my screening process is blatant incompetence. I let the schedule and the fact that I'm not really real time responding to emails and it's somewhat hard to get my phone number. It's just a way of sort of downsampling the people who are just full of shit and I don't have the time to deal with. So you guys actually showed up.

And I'm sorry for the gauntlet that you had to run through, because it's like once you make it through, I feel all apologetic. It's like, oh, God, I wasted all your time. You're sitting in the parking lot.

You know, you must think I'm a total jerk. And that is true, but it's the easiest way for me to sort of tell who cares. Because you ask somebody who cares, they always say, oh, yeah, I do.

But you have to care has to be demonstrated. It has. And so what's the best way to do that? Well, it's to waste somebody's time with hurdles.

And I actually didn't know the building was locked. But that's just me. Like I like and you guys, the fact that you solved it, it was probably great that the building was locked, because if it had just been open, you guys would have been here.

Yeah, OK, they got it. But you got into a locked building that had no sign on the door. I don't know how I'd get into that building, I honestly don't. So that was impressive enough that I took you very seriously from that moment. And I'm glad I did because I was super excited about what I eventually saw and Rezilient.

But yeah, it's not a formal process. It's just neglect.

Danish

Every time you complain about how hard it is, just remember that we got into a locked building. It is not easy. But I will say the beautiful part about this is that when we walked in and we sat down, I'm pretty convinced that I could have said anything and you would have been like, yeah, you got here. It feels like that was a big part of it. And I think people don't realize how much perseverance is important.

That was one of my greatest lessons from this. The other one is how you view healthcare. Can you share with people here what actually excited you about Rezilient, especially having been from St. Louis? Was it that we were a St. Louis startup or was it something else?

Jim

St. Louis was nice. But like I've been hearing health care pitches for decades. It is a known area of just tragedy. We're talking lives in the balance. And it's a known broken system.

So I listen to everybody who's got the idea on how to fix it. But a lot of the times they're either targeting some sort of weird problem that only rich people have. I've heard that pitch a hundred times. Or, well, we have to change the whole system so we'll start with the government. And it just it doesn't work out.

So I wouldn't even call your pitch a pitch because it wasn't a pitch. It was an explanation.

We’ve got a doctor. We've got a human in the room. We have actually access to more than one doctor. So if it's a derm question and instead of having to make an appointment, you could just get a dermatologist, you know, remotely. And it made so much sense.

The fact that it was easy to understand and also your credibility. The two of you guys are not shiny shoe jack offs who are trying to exploit a known weakness. You're a physician and you're you're an accomplished engineer. You guys have the ability to get other jobs if you needed it. You aren't doing this because Bitcoin's down.

That means a lot in credibility. You combine a good idea with a quality team and that magic persistence. And now you have something.

Oh, and a and a giant problem. I studied a lot of companies who had this this amazing trajectory and they all had a lot of similarities. They're rare. It doesn't happen that often: one out of 10,000 companies will fall into this special category. And the category is that they're solving perfect problems.

If you think about all the problems that exist in the universe, some are unsolvable. I always use the example of teleportation. I’ve got to go back to New York tonight. It's going to be five hours commuting. I would love to be able to teleport.

But that so far is an unsolved and I would guess unsolvable problem. It probably violates some law of physics to teleport.

Then we’ve got all the problems that have already been solved. Like there's a YouTube video. There's some expert. There's some dude or conference you can go to solve problems.

But then there's this barrier between the unsolved problems and the unsolvable problems. And you don't know where that is. You don't know if what you're trying to do can't be done or just hasn't been done, and that's the area that these magic companies address. I call them perfect problems.

But this is something that you don't know if it's going to work. But God damn it, if it does, it makes a difference. And it makes a difference because you care about the problem.

And healthcare: we’ve all seen people suffer. That is a problem that will motivate teams. And you come to work feeling great about what you're doing. You don't have to explain, oh, why do you work 14 hours today? That to me is very compelling, and you guys have that.

Danish

We got lucky at some level in that we tried to do a lot of different things. And then we fell into this perfect problem, which was employers are spending too much time too much money on healthcare.

And because the system's been built around government-sponsored health care, employees are being neglected. If we could just provide great care for employees, it would save employers a ton of money, the employees would get healthier, and so on. And that sounds all great until you realize you've created 10 new problems.

Then we solve those and create 100 new problems. But one of the things that I wanted to focus on today was around healthcare in general and your overall thesis. You're somebody who's done a lot of finance, a lot of fintech, but you have a connection to healthcare, especially with your new company and what you're building now. Can you tell us a little bit about the new company?

Jim

My wife and I have pledged to give away all our money. Don't talk to me, talk to her. What we've done is we've discovered that I'm actually no good at giving away money, because I say yes to too much stuff.

Like you show me some suffering kitten, and I'm like, here's a check. That’s not good philanthropy. So the rule now in the McKelvey family is Jim doesn't get to give away anything. So what am I allowed to do? Well, I'm allowed to go out and take risks that somebody probably couldn't take unless their family wasn't in danger.

If you have to go and put food on the table, you probably don't want to do what I do every day. But since my family's safe and my kids will be fine, I get to take crazy risks. So I look at problems that I think could have an impact.

One of the things I look at is healthcare and particularly something called Eroom’s Law.

Eroom’s Law, which is not a joke, I'm not making this up, is Moore's Law backwards. So if you spell Moore backwards, you get Eroom. If you think about Moore's Law, think about all the amazing stuff that you have, these supercomputers that are in our pockets, all of the cool things that are happening are happening because of Moore's Law, which is the exponential improvement of technology.

But for some reason, in health care, there is an exponential decrease in the drugs that we get to take. And there is an actual slowing down of the drug pipeline that actually gives you an approved, safe, known drug. We get about 30 drugs a year right now.

We should be getting 1,000, but we're not. And if you look at the entire system, one thing is painfully obvious is that it is hugely, absurdly expensive to go through the FDA approval process. It's insane. It's like $100 million to take a shot on goal if you have something that might save a life.

And you think about it, you got all this AI, I got all this cool tech, you got all this amazing discovery. That's all Moore's Law stuff. We're getting exponentially more of that. What we have not improved is the pipeline that says this is actually safe or not.

That pipeline goes to the FDA, and it costs $100 million in round numbers to try something. If you need to raise $100 million to take a shot, then you probably need a billion-dollar payoff if that shot lands, because some of them won't land, and you need investors to take these shots. So the math really kills a lot of people, because a lot of projects, but those projects can save lives.

I've seen pancreatic vaccines, I've seen pancreatic cancer vaccines. I've seen AIDS vaccines. I've seen all sorts of amazing stuff.

We just don't know if they work. So what I'm doing now, I've got a very small team, and what we're doing is essentially partnering with companies that have drug assets that they can't afford to test. And we say, we'll pay for the test, and we'll take a piece of the action.

This is actually for profit. We'll take a piece of the action if it works. My hope is that we will be able to cut 90% of the cost out of drug trials.

90% is a crazy number, but I've actually run the numbers on what you actually have to spend, because you have to pay patients, you have to manufacture drugs. I mean, certain things you have to do, but I think a 90% savings is possible. So the thought is, if fast trials works, it will be a model that others will copy.

Much like Southwest Airlines was this discount model for air travel, and other companies eventually copied them, so now we have fairly cheap flights. As a matter of fact, the reason my Delta flight tonight is going to cost $200 is because of Southwest. Because believe me, Delta in the old days would be charging me $1,200 to fly me back to New York tonight.

So that's what I'm working on, and I have no idea if it's possible, but we start our first trial in a month at WashU.

Danish

I would like to believe that we inspired you to go into healthcare, but I don't know if I can say that. One of the big things that I think our folks that are in our ecosystem, in our community, our employees, would like to know, is how do you view decision making at this scale? We're going from product market fit to now scaling.

What advice do you have for our people about how we get from here to scale? We are growing at such a rapid rate, and the number one thing that keeps me up at night is, how do we take care of our existing customers to make sure that they don't suffer the consequences of scale that's all I think about because I want to make sure that they're taken care of.

Jim

I'm jealous, and I'm also incredibly sympathetic. As you're saying that I kept picturing the rock and roll roller coaster at Disney World? You sit in it and it's not a traditional roller coaster, it has a ratchet thing it goes up a hill and if you're in it it just pins you to the back of a chair worse than any Tesla, and you just go whipping into the darkness. That's the beginning of this ride and it lasts for second and a half.

That's what you're in right now: you're in that second and a half. It is insane to be in a company that innovates and does something new, then all of a sudden you have this market with this tremendous vacuum force, because what you have can't be delivered by anybody else. Nobody else has figured it out and for a brief period of time you're the only people who can deliver it.

Now if you don't deliver, eventually others will catch you but if you accelerate into that you can end up essentially defining the whole market. That’s what Apple did with the iPhone. It's what Square did with small business payments.

But it only lasts for a very brief brief time and it's tough, especially if you have lives on the line – which you do. If I drop all the ball a guy loses a sale; if you drop a ball somebody could not get in to see a physician or something could go wrong. These are serious consequences.

It's not going to last that long. Square for the first two and a half years doubled in size every other month – the company had twice as many customers, twice as many servers, twice as many customer service complaints, twice as many investigations, and twice as many situations where we had to tell employees that that's not appropriate at work. Everything doubled every other month and it was crazy, but it's magic. Most people never get a chance in their life to be part of anything like that. Most people will spend their entire lives doing stuff that has already been done.

The acceleration can make you want to black out at times and you’ve got to hold on but most people never get to look back and realize it’s magic.

Danish

How do you focus on what's important?

Jim

It should be obvious what needs to be done short-term. You've got good leadership here, you've got smart people and I assume there's some good systems for feedback in the organization.

Nothing we did at Square past the first three weeks was not obvious. There are a lot of distractions and there are a lot of people who will say oh do this. AI is a giant distraction right now. I would simply focus on the problems that are stacking up, like how are you going to onboard the new healthcare group? How are you going to make sure that your systems don't break?

Just understand you don't get to live on the rollercoaster forever. It's just that very very brief moment, and we burnt out people we had people. But the ones who made it – I see them on the other side now there is a bond. I never served in the military but I I've seen people in the military talk of this camaraderie of being in battle and perhaps it's kind of along those lines.

Danish

A lot of our employees have been the ones doing the day-in-day-out work and we're now getting to that point as we're scaling where they're kind of hiring the people that are going to be below them. A lot of them are scaling up as managers. What advice do you have for them as they're hiring?

One thing that comes to mind is the the impulse to want to just put a butt in the seat because you've got to solve this problem. What is your advice to them as they're thinking through this?

Jim

Marriage is easy, divorce is hard. Marriage you can do in ten minutes for a ticket to Vegas. Divorce takes a bunch of lawyers and a lot of government approvals.

As much as you want to fill that seat, you don't want to put the wrong person on the ride because this ride’s accelerating. They probably don't know it because what in their life has ever been analogous to what you're living through? You got zero experience. So they're saying yes to something that they have no concept of, so even if they're not lying to you they're probably not ready for it. Of course it's a job interview so you better assume they are lying to you because that's what job interviews are. The job interview game is: I offer you this job and you try to say whatever the hell you can to get me to hire you because you figure what's the worst gonna happen I could just quit.

First of all, I would be brutally honest with them so you can scare some people away with what's going on. I always try to scare people away when they're joining one of my teams and I'll tell them all the reasons it's not gonna work. I'll tell them all the problems. I'll tell them what they're in for and that this is unique and they have probably a dozen other options that nobody would blame them for taking.

Don't force the fit and be brutally honest during your hiring process: this is what we're going through this is what’s next, you are jumping on to a very very fast-moving platform.

Danish

What do you mean pay to play at the FDA?

Jim

You got to spend money. To use the Disney analogy again: did you know that you can buy your way to the front of every line at Disney World? Not fast pass, you give some dude five grand and they'll just take you to the front of the line.

With fast trials, we just leave the FDA alone. There are all these players who charge way too much money for patient recruitment. Our next drug trial is gonna be eczema. It's not hard to find people with atopic dermatitis and if you are in that category it shouldn't cost $20,000 for us to find your name and say “would you like to try this goo that might cure your eczema”. That should be cheaper.

As far as the personal advice goes, you’re in a magic spot if you're in with Rezilient. One of the benefits of being in a hyper growth company is that there are hyper opportunities. The people who are running Square today the guys who are all getting you know 7 to 10 million dollar salaries. Those those fall into two categories: one, they either were superstar recruits that we pulled out from some other super organization, or they were in the trenches at the right time in the work their asses off and they rose. We hired this guy who turned out to be sort of a knucklehead we had to fire him but his personal assistant is now a multi-millionaire making 10 million a year because of the way he performed during that moment.

Look around the company – what needs to be done and are you qualified to do it now? You can't do something on a patient that you're not legally qualified to do, but that doesn't mean you can't help out in a bunch of areas. That sort of spirit is what happens when you're understaffed. When you don't have enough people in the right roles and you haven't had time to organize it because it's doubling so quickly, then you you multitask and that's a great opportunity especially if you're a person who wants to grow. You may say “I started off over here but I'm gonna end over here”.

I didn't know anything about payments, and now I know payments. You don't have to have expertise in something that is new because nobody has that expertise. What you guys are inventing at Rezilient is invention and therefore there's no expert in this new thing that you're creating. You just have to embrace the fact that while you may not technically be qualified you may be the perfect person to take some role and you'll see.

Danish

One of the Jim-isms that I take with me is that being understaffed and having less people is the feature not the bug. One of the great things that we have learned is you put people in a position to succeed and then they do things like help out on areas that they don't know much about. Jenn walks by Andrew’s office and Andrew is sitting there trying to figure something out. Jenn can jump in and help, and that actually helped bring people in the company closer. If everybody had everything they wanted they probably wouldn't talk to each other.

Jim

The Square reader – which I designed and built – was flawed. It was that little white square and you'd swipe a credit card through, and if you weren't careful the credit card would wobble and it wouldn't read correctly. I'm a good engineer and I recognized this after the first one and realized I need to make it wider so the card doesn't wobble. It's an easy solution – you make the track wider and you solve the problem.

I actually manufactured both a small reader and a big reader and tested them both. The results of the test were really interesting – if I tested them together everybody preferred the big reader because it worked perfectly, but sometimes – and this was almost an accident – sometimes because the big reader didn't fit in my pocket, more specifically the useless pocket in your blue jeans. The square reader fit in here, the big one didn’t.

I always had the square reader on me and sometimes I tried the little one without the big one present, and the results were magical. People were mesmerized by this little thing because they'd never seen anything that small. It was this moment where I had their full attention, so when we released the product we intentionally chose to ship the small reader and we never shipped the big one.

The small reader in the hands of a million customers turned into a million advertisements because it turns out it wasn't that hard to swipe. After 20 minutes of practice people would do it perfectly. What do you do if you've learned a skill that took you 20 minutes to acquire – you want to show it off to somebody: “oh look at this thing I got, it's called Square, it reads a credit card, it's free”.

Amazon came after our market when we were a three-year-old startup, right in the middle of that acceleration. Amazon decided they wanted to take the whole thing away and when Amazon does this to a startup they always win, it was 100% the case back when it happened to us. Amazon always won that battle, and we were terrified. But there wasn't much we could do, because when you are resource-constrained and growing at that exponential rate, you want to fight Amazon but you’ve got all these other fires to put out. I didn’t have their budget, I didn’t have their teams, I didn’t have their balance sheet, I didn’t have a listening device in all your homes. It's not a fair fight.

We eventually won. I was happy and then I was confused – what the hell just happened? Why did this happen? Has this ever happened before? And it turns out it actually has happened. There are examples of a similar philosophy or a similar phenomena.

What ultimately happened with us and Amazon was we did some stuff that to them seemed stupid and to us made sense, like released a little reader that didn't work very well. Amazon released a reader that worked perfectly and nobody liked it. We had this cool little thing and they couldn't understand because they probably studied it with a bunch of engineers and go “the Square thing doesn't work, we can do better than this”.

So let's say a Rezilient is already successful. How long will you be able to sustain it? The copycats will come. They will fall mostly into the category of other organizations that want a slice of the money they see you making, but the thing they won't know is why you do it. You will have certain systems that you have organically created because of the stress that you're under right now. I know you guys are stressed – you have to be there's no way to be in that acceleration and not be taxed – but that forces you to do things and you understand why you're doing those things. Some guy coming from the outside doesn't know so even mighty Amazon with their listening devices and their armies of flying robots and their giant balance sheet couldn't take on a startup that was in that growth moment. They just didn't know why we were doing what we were doing and they couldn't copy it.

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