This weeks episode we’re talking to Rhonda Ozanian. An NYC founder igniting brand-new tech that delivers $billion-dollar results to companies while closing $trillion-dollar money gaps that 120-million Americans face every day. Stepping out of a fast-paced Wash D.C. career, Rhonda bootstrapped her way to Wall Street to create a new financial backbone for consumers missing today. She is a technologist, economist and behaviorist with a PhD from Columbia University. Before taking on one of the most daunting challenges facing the economy today, Rhonda served as a combat deployed military officer and a Congressional Fellow with the Senate Finance Committee and Brookings Institution.

Rhonda’s Top 5 Leadership Tips:

Below is a summary of the Top 5 Leadership tips shared during the interview this week. Take a listen to the episode to learn more about the thoughts behind these tips –

  1. Don’t Over-Index Your Weaknesses
  2. Learn From Failure
  3. Dealing With Hard Times
  4. Be Careful On Social Media
  5. Never Give UpTip

We hope you enjoy the episode. You can find even more Full Stack Leader episodes here:


Show Transcript

Ryan: Hello everyone and welcome to this week’s episode of the full stack leader podcast. This week. We’re excited to have with us, Rhonda Ozanian. She is the chief executive officer of the second wallet. Great to have you here, Rhonda. We’re excited to talk to you. 

Rhonda: Hi Ryan. 

Ryan: How are you? I’m doing great. Thank you.

Happy Friday. Yeah, I was wondering, maybe you could tell us a little bit about how you ended up at the second wallet, kind of what your path in your career was. Give us a little insight on that. 

Rhonda: Well, it’s been quite a journey actually. So you know, the three things that I always tell people about me, right off the bat, is that number one, I didn’t mean to start a FinTech company.

I was just trying to solve a problem and it required me to start a FinTech company. The second is that I have no pedigree in the financial industry. I have bootstrapped my way, teaching my I’m probably the only living soul that ever 

taught themselves the financial industry. 

Rhonda: And the third thing that I tell everyone is that I am an orphan.

I was actually born in, raised in rural Arkansas, by grandparents who are very poor and they were farm workers like agricultural workers, 

cotton farm. And when I was, 

Rhonda: When I was 18, I did what millions of people before me had done when you’re poor and you want to have a better life for yourself. I joined the military as this scrawny 18 year old kid.

And I went to school and I’m at school at night. I went to school on the weekends in order to go to school. And I did that, but going back just a little bit about making a decision like that to, you know, pull yourself out of poverty, the problem is that you leave other people behind. And that was the case.

And my family was still for 

no matter what I did. And over there. I wanted to help them. I 

Rhonda: tried to help them and really use every opportunity I could to help to pull them out of poverty. But it was really hard because you don’t know, you know what people back home are doing. Somebody needs something you don’t know if they really need something.

Or if, you know, there’s something else going on other way, the information and the signals were very, very weak and it was a, and it was a real burden on me through the years, knowing that there were people and never being certain what happened to the money once it changed hands. And it wasn’t until years later, when I worked on Capitol hill with the Senate 

finance committee 

Rhonda: that I made two important discoveries.

One is 

that a. 

Rhonda: I wasn’t the only person, they were actually 120 million people that had this problem. And number two, there was a really structural problem in our banking system that caused that to happen. So 

that’s sort of a long winded 

Rhonda: way of say, you know, this is, this is sort of the 

journey that I’ve been on.


Ryan: It’s a pretty astounding story. And I, one of the things I know we talked a lot about with founders creating companies is really having a purpose behind the company and it sounds like you just have an amazing foundational purpose behind the things that you’re doing. you’ve got you entered in the military at a relatively young age and, and I think you pretty extensively in the, in the air force, correct?

Rhonda: Well, I started out actually in the army the first four years of, and went to school at night and weekends to get my bachelor’s degree. And then came into the air force as an officer and the rest of my career was spent as an air force officer. And it was during that time when I was in the air force that I was combat deployed to Afghanistan.

I was in charge of a detachment of people who, you know, our, our mission was outside the wire. You know, my mission was to place people at these small fire bases across the mountains of Afghanistan, providing 

crisis and mental health 

Rhonda: support to units and soldiers that had, you know, an ID event or some bad outcome that they needed support.

And so we had people all over and my job as the commander and the leader was to, you know, jump on a helicopter in the middle of the night and go out to these different fire bases and rotate people around as much as we could to make sure that nobody, none of our folks got got burned out. So that was what I did.

You know, when 

Rhonda: I was deployed. And then when I came back from deployment Knowledge background. They pulled me up into a presidential commission to serve the presidential commission. And we worked on technology to get wounded soldiers off the battlefield and, you know, safely back to their homes, in Iowa or, wherever they come from.

And from there they pulled me over to the Pentagon where I worked as a senior policy analyst for the assistant secretary of defense. And from there 

I decided, 

Rhonda: I was kind of on a short list for ran fellowships and other things. But I had an opportunity to become a congressional fellow.

And so that’s 

Rhonda: the course I took. So I left my military career there and my 

worked for them for a couple of years. And it was really there that I had that moment of clarity around. Wow. You know, this thing that I felt so badly about all this time is something that families struggle with all the time and 


Rhonda: of the way that our population has changed.

Where we’ve got, you know, there’s massive number of people that are aging and a 

whole lot of 

Rhonda: wealth that sort of concentrated there. And we, the fertility rate of this country is actually quite low. So you have this huge, you know, population at the top, and then you have a smaller workforce. And 

I was like, wow, this is crazy.

I want to go see what 

Rhonda: I can do it. So I left completely left public service at that point and became an entrepreneur 

and just 

Rhonda: started, you know, peeling back the layers of the onion. I didn’t know at that point, what I was doing in terms of what I was starting, but that was before 

Ryan: We got too deep into this.

Cause I really want to go into this. Let’s go back for a second to something you brought up a few minutes ago. You were talking a little bit about your transition into overseeing it, it sounds like a pretty intense and specialized mission in Afghanistan. And then you transitioned into more of a leadership role But when you were in Afghanistan and, and handling that, what was your training to run a group like that? Like, how did, how did you undergo to learn how to do. 


Rhonda: I mean, I think at the military you’re always training, so you’re always preparing for, for something, but it was really because it was an interesting experience in Afghanistan.

There were a lot of people that were deployed in situations that especially like the air force that they weren’t really built for, you know, it was kind of more of an army kind of mission. And so, it, it was, it’s so funny that you 

asked that question 

Rhonda: because one of the first things that I figured out when I got there and with my team is that they actually didn’t have adequate training.

For what they were being exposed to, 

Outside the wire. So a lot of what I had to do as a 

Rhonda: leader was to say, okay, hold up. You know, we really have to make sure that you know how to drive a Humvee, that you know how to use your weapon 

properly. Of course, everybody knows haven’t used her weapon, but we needed 

Rhonda: to use it better.



Ryan: they’re really skilled with it, 

Rhonda: right? You have to be very skilled with it. So there are actually some skills that we had to acquire on the fly in order to keep people safe. 


Ryan: And, and when you’re working with a group like that, and you don’t have a ton of training, you know, they’re looking to you for the training.

Was that, was that hard sometimes? Was it hard to kind of on the fly be thinking about, okay, we’ve got to put these things together and I don’t have a lot of experience doing it. 


Rhonda: was. And especially given that we, none of us were sort of bedded down in the same place because we had to cover the whole theater of operations.

And so I actually 

Rhonda: came up with and this is less about training and more about just taking care of people. I came up with the system around moving how we moved people in the theater, so that. Certain bases that were larger and had food and had hot showers and 

a couple of 

Rhonda: amenities. And then there were some that were just so far on the mountain side.

You, you literally were in a 

tent living on crap. Yeah. And so 

Rhonda: I devise sort of this rotation schedule through these ring routes, which are the helicopter helicopter routes that you take where I sort of envisioned, you know, the main base is being kind of the, the Marriott and those small firebases as being the motel six and then really starting to rotate people through.

So they had time to come in, you know, have a good shower, have some food, pick up some supplies and then kind of go back out so that I really started to kind of rotate people so that we had 

coverage on these bases. We had continuity on those basis, but at the same time, 

Rhonda: people could kind of come in and 

have a couple of days 

Rhonda: And we would kind of go out.

Somebody else would go out and cover them without losing that cotton. That was probably one of the more creative things that I did. And I’m always very creative. 

I mean, even having spent a 

Rhonda: my whole career in a very structured, bureaucratic environment, I have always felt that I had the power to be creative.

And that was one of those examples where it was very, it was very unconventional what I did. But you know, the decisions that you make as a leader and some of the things that you do, you know, the thing is, and this is the hard part of leadership is that you’re always standing alone. And you have to be able to stand alone.

And that was really kind of talking about kind of those leadership 

challenges. You know, you’ve got to be comfortable standing in those shoes. And I think because of my 

Rhonda: background, having come from such humble surroundings and having to make really hard decisions to leave home, to begin with much less to join the military I, I have had to be very comfortable standing alone and standing up for what, you know, those core values 

and that foundation that I have, and being able 

Rhonda: to do that.

And over the years, it’s been very difficult because I’ve always been the one I’ve always been an innovator. Right. I was always the one that said, oh, I think we can do it a better way. That does not always go over very well, even when you’re working or 

Ryan: breaking the status quo. Right. Like it’s not always great.

Rhonda: That’s fine. And, and it’s, and it’s hard because sometimes you have to pick your kit, your friends very carefully to say, you know what, you don’t believe in this direction that I’m taking. And I can’t have that kind of energy. And so whether it was being a leader in the military where I have a, 

you know, official position, 

Rhonda: As a, as a Lieutenant Colonel or, 

but, but, but the, the whole, the thing that’s so amazing about, I, and I’m so 

Rhonda: blessed for the life that I’ve had, but what’s been so amazing is that having gone from this system that was so highly structured and, you know, you were ranked and therefore people 

saluted you in blah, blah, blah.

And that 

Rhonda: there were challenges from a leadership perspective there. But the other part is when I left that. Ryan. I had to start from 

the scratch. Right. I was moving into an industry. 

Rhonda: The technology was the only thing I had now. Granted 

I have a PhD in economics and policy and I know some stuff, but I had to 

Rhonda: create a new power position out of nothing.

Yeah. And, 

Rhonda: And so now it’s about the relationship. I have to lead through my own reference power and coming 

from outside 

Rhonda: of, and going into business right where the rules of engagement are all different. And I had to make a name for myself and do that as I started, you know, as I started this company.

So that has been extremely valuable. And the process of just networking with people and bringing people on board and, the same way as I had my hotel six model when I was deployed in Afghanistan when you’re starting a company you’re faced with having to like, you know, okay, equity and you’ve got to have the cap table and you have to incorporate and do some other things structurally.

And then how do you bring people on, how do you incentivize them? It’s all very murky. You could easily give away half your company just because you’re desperate. And I didn’t want to 

do that. So 

Rhonda: I did 

Ryan: So fast for a lot of entrepreneurs to do that, by the way, as well. 


Rhonda: Really hard. Right. So it was like, I didn’t know exactly where to start.

So I went there was, there was some 

basic guidelines with, I think it was the, I think it was the 

Rhonda: Founders Institute. Maybe that was like, okay, this is the general, , allocation of equity that 

you are in an early stage company. So I said, okay, I’m going to take this. And I’m going to create what we 

Rhonda: call a, choose your own adventure equity stuff.


Rhonda: I know, right. Well, I have to credit Steven Latona

He’s with a company called kava or Casper consulting in Los Angeles, but he came up with the, choose your own venture part. But basically it says, if you want to work with me and you have this much time, this is the, you know, this is the equity structure for that.

If you have this much time, this is what you get. And what it did though, is it took the mystery. It took the negotiations and the headache out of it. So the advisors that we bring on and that we work with have a very clear picture about what that, what, how much they’re supposed to contribute and what they get in return for that.

And I’ve been using the, choose your own venture adventure equity structure now for about four years. And it’s been. 

Ryan: Well, this is a blessing to hear you talk about this, because I know I do a lot of advisory work. I work with a whole host of different entrepreneurs on their startups, and I am often recommending something similar to this actually.

Because I think that understanding the equity trade for a really valuable time, not just time itself, but valuable time is really where you get the most out of your advisory board. But more importantly is the entrepreneurs like, like you actually coming in and thinking about what that value is to the organization and coming to the table with that, like, that’s a huge thing.

And I think it’s really underrated. 


Rhonda: absolutely. It just takes, you’ve got enough to do when you’re a founder without having to get involved in, in things where you could make mistakes, you could, let’s just try to systematize it. So that we can save some time. The other thing is that , my philosophy about being a founder and this goes back to the leadership part, is that starting a company doesn’t need to be a mercenary experience that, the people that I I’m going to take the risk, I’m the founder I’m taking the risks, the people that I bring on as advisors and to help along the way they don’t need to take on that.

Right. So 


Rhonda: able to bring people in, giving them a small 

amount of equity and investing and doing 

Rhonda: that allows me to assume the risk and allows them to participate while still keeping their day jobs and keeping their lives and the things that they need to do, because how many people would love to start a company, but they can’t because they’ve got a, they’ve got a family to feed, , they can’t just sort of take off and do that.

So the amount of risks that we expect founders to take on, sometimes I think we can even be creative there. And I certainly feel like I am not putting anybody 

on my team at any huge financial risk. At this point, Yeah, 

Ryan: appreciate that. So you, so you have transitioned at this point from this more bureaucratic military and governmental background into a completely new world.

And you’re shifting into leader, tell us like the early stages of how you even got started on the path of starting a second page. 

Well, I didn’t. So if 

Rhonda: you’ve known me for any amount of time, one of the things 

you’ll know about me is that 

Rhonda: I have iterated through even the name of the product and the company over time.

Our we’re incorporated as generation finance technology incorporated. And that’s been our official company name for, since like 2017 or 18. And then as part of my own product development is to look at how some different terms are, or are resonating with people in second payer was one iteration of that.

Now we know that the product is actually called the second wallet. But I kind of took the Liberty of just sort of letting the names 

and testing the names in the market, 

Rhonda: Throughout that transition. But remember when I started, I didn’t know exactly.

I didn’t want this to be a nonprofit. 

I set out to find a market 

Rhonda: solution to a very real problem, a very large problem that millions of people had. 

I didn’t know that it was going to be a FinTech, but I knew it wasn’t going to be a nonprofit. I took some time to do a lot of research and development in the area of, just business and learning business and economic development 

and really studying.

This particular area of, of economics. And 

Rhonda: Just again, you’re building a product, testing it out, and then, here’s the thing about being a founder, right? You wake up in the middle of the night and you, you have a talk with 

yourself and you say, is this, is this 

Rhonda: the right product? And if the answer is, no, you need to start over.

And I did that a couple of times until we got to where we are right now, but here’s the amazing 

thing is that, and this goes 

Rhonda: over to some of the five leadership tips . That I know that we’re going to be talking about, but there are some 

dark days. And 

Rhonda: As a founder, you have to.

Live to fight another day, right? You, you have to survive those dark days. 

And four months, 

Rhonda: I was, I was talking with banks and talking with financial institutions and they loved it, but it would get second while it would get to the investment committee and there would be like, Nope, go get some traction, go get some traction, go get some traction.

And I hypothesized all sorts of reasons for that. Right. And this is one of the truths is don’t over-index on your weaknesses because I’m 

like, oh, it’s because I’m a woman. I’m a 

Rhonda: girl. I’m, you know, middle age, all these 

sorts of things. But I had a moment of clarity 

Rhonda: after one particular founder or excuse me like, accelerator venture fund had, had turned me down and it, and it came to 


I was like, wait a minute, maybe this is about 

Rhonda: the product. 

Right. Maybe 

Rhonda: the product 

just isn’t that good. And I, I jumped up and I grabbed a piece 

Rhonda: of paper 

and I thought, you know what? Finance 

Rhonda: People don’t like to talk about money. Right. That’s why a lot of finance platforms just don’t do very well because we don’t like to talk about money.

What we do like to talk about 

is saving money. And, and we don’t like to 

Rhonda: talk about accounts. We talk about apps, right? So it was really like, wait a minute. I’m thinking about this whole thing wrong. So I sat down and I did some design on a piece of paper and I threw it on a PowerPoint slide. And I started going to my team and my advice or something like, look, I think, I think this 

is it.

Because up until that point, we had 

Rhonda: built out an MVP beta version. Great engineering, you know, really core. We did exactly what we were supposed to do, which is make it lean, 

make it only do one thing, 

Rhonda: But here’s the part they don’t tell you is that if you try to put an app in the market that is lean and only does one thing, you are unlikely to get any traction.


Rhonda: I had not built out the consumer phase. I kept it very enterprise. This is how it would work incorporated as part of the core banking experience, which is where we really believe this product belongs. But it was very mean. And I think that investors just couldn’t put themselves in the story because it was so lean.

So I sat down and I put it on paper. I threw it on a slide. I started talking with people 

and it was like night and day. Because I missed it. Right. 

Ryan: So maybe we can go back to this, this point, go into a little more detail on it. I think it’s interesting because as a leader, you are always having to try and discern what the right next path is.

And sometimes the guideposts are really unclear. There was something that you spotted within, within the feedback you were getting over and over again, that helped you realize that the simplicity of the original product was leading to nos essentially. Right. How, how did you, like, do you remember, like, what was the kind of trigger that allowed you to see that thing.

I, I 

Rhonda: do remember the trigger. And it was, 

it was just 

Rhonda: and I can tell you even where it came from, it came from a fund called the Anthemis, which is a woman, 


Rhonda: kind of fund. And I actually called them up a couple of days ago and talked with one of their, one of their partners.

And I thanked 

them. I said, do you know what 

Rhonda: I was missing something? And, and it wasn’t until, you know, you guys said, no, I’m sorry. We can’t work with you. That it happened. So being told no yet one more time. And it happened to be them. 

It was at, that was the, that was what I told her. I said, you have given me.

Yeah. I had a 

Rhonda: meeting with myself and what I discovered is that the product was wrong, but nobody 

was telling me that. 

Ryan: Yeah, it’s just so interesting because like, it really came from a clear visionary place. And those moments are really beautiful. They really are like that, sometimes you can’t describe exactly what it was in it, but the thing that brought it together and allowed you to see adjusting this direction is really interesting.


And I was going to also say that it’s you’re right. It is, it is a more global truth. I think we hear a lot of generalized tech speaker or venture capital speak, reading blogs or articles, or talking to people that say all kinds of different things about it has to be like, this has to be like this, but you come to realize like over the course of time that it actually, sometimes, sometimes everything you’re hearing, isn’t actually the way it is in terms of, of making it a spark for people.

Rhonda: Yeah, 

That’s right. And you, and you know, here’s the thing is that 

Rhonda: I think founders mostly misunderstand 

the role of venture capital venture 

Rhonda: capital is they’re not going to 

start the fire for you 

Rhonda: right there. They’re going to tell you to go start your 

own fire. 

Rhonda: And they do not care. If your fire doesn’t start, they’re going to push 10 people to the edge of the cliff, encouraging you to jump.

And the one that makes it is, is the one 

that they can maybe put some gasoline on that fire. Yeah. But they’re, they’re not there to see you succeed 

Rhonda: Until you, they write you a check, then they’re very happy. They want you to succeed. But until then they just want to 

see who survives. 

Ryan: Yeah. This is like a survival game or like a, like a great competition.

And you don’t even always know you’re in it. 

Rhonda: You 


Rhonda: And it is a shame though, that there is not a mechanism to get more honest feedback and somebody saying, you know what, it’s okay. But it kind of sucks. Because that would have been really painful. And I’m sure that’s part of why nobody will tell you that.

But for me, 

As I say, 

Ryan: have you learned how to hear the, it sucks even within the language that is not clear and direct? 

Rhonda: Well, apparently I apparently I didn’t for a long time, I get it now, and this is one of the other, leadership tips is that we learn a lot more from failure than we do from success.

Ryan: Absolutely, absolutely. 

Rhonda: But here’s the thing, but here’s the thing. It did not stop me, I didn’t, I didn’t lay down my weapon and there were, again, we were talking about those dark days. There are some very dark days there. There was a period of several months of just sort of, I could only look at the computer for an hour and then I had to just go.

Take a nap, 

Rhonda: I had to just step away from it and then get back up and come back to the computer. But I always came back since I backed down at the computer and kept going. I’m just looking forward to a better 

day, but, but this wasn’t it. Do you think 

Ryan: That you just have such a rich past, do you think that that kind of stamina and recommitment to what you’re doing?

Is it, does it come from your childhood and, and going through being an orphan, does it come from the military? Do you think it’s a combination of the two? 

I think it mostly comes from my childhood. So when I was a little girl. 

Rhonda: You know, a little homely girl, I mean like super homeless. I’ve always been very homeless.

I’ve never been somebody. Oh, she’s so beautiful. So I’ve always been sort of that wallflower, right. And with my grandparents and being so poor, 


Rhonda: didn’t even have, you know, things I could read. You know, well 

beyond what I had from school 

Rhonda: and I had some extended family, not even biological family that would bring like magazines when they would come visit.

And I would just sort of just pour through books, any books and magazines I could find, but it was also really self-conscious my favorite game to play when I was a little girl, of course I was playing alone because there was nobody around, but was, , 

office, I love to play office, 

Rhonda: But it was very, I was very self-conscious about how poor we were and we didn’t even like, you know, the walls needed to be painted and we, we didn’t even have paint.

Right. And I was like seven, by the way. And I would get a bucket of water and put some soap in it and get like an old rag. And I would wash 

the walls 

Rhonda: because in a world where there’s so many things you can’t do, there’s always something you can. 

Right. Oh, that’s 

Ryan: such a great piece 

of advice for all right.

Ryan: and being a leader, you have, you have to be able to find those because you will upon dark days, 

just like, and that, and that’s always, the hard 

Rhonda: thing is because that’s generally not the way people do things. You know, if it’s not easy to 

do it, it’s not going to be done. It’s 

Rhonda: going to be, the number of things I’ve worked on over the years has been told you can’t do that.

It’ll never work. But again, as a leader, you have to separate yourself. You have to have a true north. 


Rhonda: got to follow that. 

Ryan: That’s really great. Thank you for sharing. All of that is, it is an amazing, amazing experience hearing about your past and all the things that led up to where you are now at your second wallet.

Like it’s, it’s just absolutely. We’re, we’re excited to go into your top five tips and we’ll be back in just a minute with 


Break One 

Ryan: During my interview with Rhonda, I was reminded that one of the most powerful tools in our entrepreneurial bag is resilience. She’s put this tool into use throughout her entire professional journey, as well as her life. Her experiences with poverty early on transformed into a powerful asset during her time in the military.

And then both of those became central to creating the foundation of a successful startup that is trying to change the world of finance throughout it all. She reminds us that resilience makes anything possible.

All right. Welcome back. We’re again, we’re here today with Rhonda Zenia. She’s with a second wallet and she has some amazing leadership tips for us today. So let’s go ahead and start with tip number one. What do you have for restaurants? 

Tip One (Don’t Over-Index Your Weaknesses)

Rhonda: Well tip number one is don’t when you’re a founder and leader, don’t over-index on your weaknesses because it can hide certain realities.

You know, as a founder early-stage company and VP looking for funding really out there trying to, trying to meet people and work deals. 

And there’s obviously a high 

Rhonda: rate of rejection there. And you know, if you start to look at the fact, 

which is my 

Rhonda: mistake, which is, oh, you’re a woman, oh, you’re this or that.

You’re hiding behind that. And part of really listening and opening yourself up to feedback to investors, you’ve got to get past that. 

You’ve got to get 

Rhonda: past the, the the, those weaknesses. So if you’re hiding behind that and saying, oh, it’s because I’m a woman, it’s because. Whatever then it keeps you from seeing what the issue 

might really be.

Ryan: Yeah. I really liked that term over indexing and putting too much value on something. It really, but there are good spots to notice, but also not to be caught 

up in. . 

Tip Two (Learn From Failure)

So tip number 

Rhonda: two is something that I mentioned already again, is that we learn more from failure than we do from success.

I credit myself with being the world’s most successful failure. You know, I came from way, you know, I’ve had a lot of catching up in the world to do as an adult. I have 

failed and I haven’t just failed. I don’t want to see even use, I have 

Rhonda: not been good at so many things that I believe in and that I’m passionate about.

You know, economics is my love. It changed my life. And it’s very much the backbone for second wallet, 

but as an economist, a horrible economist. But it doesn’t matter. I’ve done 

Rhonda: more. 

My economics professors in school would be like, oh my gosh, you know, how are we going to get her through this? 

Rhonda: But here’s the thing, even though I was 

bad at it, it has 

Rhonda: been so important in creating the company and the 

backbone that, 

Rhonda: that we’re working from today.

So, you know, even when you’re not good at something, it doesn’t mean that you can’t take 

and do something amazing. 

Ryan: Well, and I think that’s a great point. Your relationship with resilience and sticking with something, even if you struggle with it is super important. Because one person’s experience with failure can be very different from another person.

A lot of people use it to actually power them. 


Tip Three (Dealing With Hard Times)

Rhonda: three, tip number three, 


Rhonda: with the dark days. As a leader, you know, you do have to stand on your own a lot and when you’re a founder you, it it’s all the more true, you know, when you are, 

it’s a 

Rhonda: heavy burden being responsible for other people, being responsible for a company, 

Sometimes things don’t go well and you have to be able to deal with those dark days in a measured way.

Rhonda: Very purposeful kind of way, understanding that there will be good days, but they may not be coming. 

Maybe not today. 

Rhonda: It may not be coming anytime soon. So really being able to give yourself room to, you know, take a break, go do something to, you know, produce some dopamine or something in your system because those dark days are just what they are.

It doesn’t mean you should quit. That’s the thing. It doesn’t mean you should quit, but it does mean that you’d need to get real honest 

with yourself.

Are you 

Ryan: able to effectively notice when you’re in the dark days or do you sometimes find like, oh, I realized later I’ve been in it for a little bit. 

Rhonda: I’ve gotten much better at it. You know, there were a couple of months recently that were really dark and. And I knew that, I could not even sit at the computer for longer than hour before it just became overwhelming and I had to step away, but then I always came back to it because I knew 

that there was going to be a better day.

Ryan: Yeah. The consistency in response and commitment and to come back to them. That’s really powerful. All right. Let’s jump into tip number four. What do you have? 

Tip Four (Be Careful On Social Media)


Rhonda: number four is pretty practical and 

That is, be careful with social media. And I know that that’s, 

Rhonda: Now, that’s a very practical thing. Social 

media, the anonymity, 

Rhonda: And our ability to post, whatever the hell were they thinking about at any given moment.

You don’t know who’s seeing it and you don’t know how they’re reading it. And in 

business, I think that this is especially 

Rhonda: true. I’m, I am on Twitter for example, and I follow I’m very strategic. So I follow all the best venture 

capitalist I have never, and 

Rhonda: some of my best friends are VC, 

so don’t get me wrong.

But I have 

Rhonda: never lost respect for so many venture capitalists then just following 

them on Twitter I’m kind of at a point where I’m 

Rhonda: gonna have to stop following people 

because it’s negativity, but it’s also arrogance. 

Rhonda: It’s also their real feelings about founders. And sometimes that’s not very positive.

And I can’t do that. That’s not, this is not where my head is, so I’m going to have to tune out. But anyway, for people that do post a lot other 

stuff, you know what I mean? Keep it positive, keep it real. 

You don’t need to post everything you think. 

Ryan: Yeah. I think that’s great advice. I know for me, and I know my team, we talk a lot about posting things that help people to like, like actually being helpful.

There’s great opportunities 

for that. I think that’s where people focus on that piece.

Tip Five (Don’t Give Up)

I think the fifth tip is really don’t give up. 

Rhonda: None, none of us are perfect. And whether you’re taking a leadership job at a, at a large corporation, whether you’re a founder like me there’s always going to be people saying, do it this way, do it that way. And it’s going to be discouraging and you’ve got to get past that though.

Right. Having that true north and knowing that, don’t give up whatever it is that you’re aiming for whatever you’re trying to pursue. 

You know, 

Rhonda: Sometimes you’ve got to step back. Sometimes you’ve got to go left, you’ve got to go. But don’t ever give Yeah. And I think

Ryan: All this, all this storytelling you’ve been doing up until now kind of that concept of being able to pivot and evolve and change and at the center of you you’re always being driven by the thing that you have vision for me of hard work and you feel that.I mean, I’ll 

Rhonda: I’ll tell you one thing, and this is I’m, I’m giving you a tip. Number six here. You’re welcome to edit it and call it something else. 

Here’s the bonus tip 

Rhonda: is that when you’re a leader, you sometimes have to let people go, you have to fire them. You have to redirect them. You have to do those kinds of things.

In business, sometimes not everything is a winning deal, right. But it there’s nothing that brings me more pleasure than having somebody reach out to me on 


Rhonda: when things didn’t go well and connect them. 

Because I know I don’t have to, I don’t have to be light to be a good leader. 

If somebody respects me and I I’ve done well by them, even 

Rhonda: if we don’t agree and they reach out to me later because they want to connect with me, that’s 

that feels it’s much better than 

Rhonda: having somebody just simply like you. Right. 

 And that happens to me. That happens to me a lot where people 

Rhonda: that I’m like, you know, 

it didn’t work out very well, but sometimes, the 

Rhonda: dust settles, tempers, settle down.

And, but I love it when people can come back together. Even when they’ve had those kinds of differences. And that’s one of the, probably the things about being a lifelong 

leader that I love the most. Well, thank you. That 

Ryan: It’s amazing. I really liked that perspective because you’re right. When the desktop.

We are all people that work together and learn from one another. So truly powerful. Rhonda, it’s been amazing to have you here today. I really appreciate all of your insight and the ability to experience everything you’ve been through in the past and experience you have a incredibly varied career and and appreciate your level of, of resilience and 


Ryan: That I’m experiencing.

You bring to everything that you’re doing. It’s great to have. 

It was great. Sharing 

Rhonda: it with you, Ryan. I appreciate the 


Ryan: What amazes me is that Rhonda never set out to start a FinTech company. Instead she wanted to solve a broadly important problem facing millions of people. She saw that this financial weakness in the marketplace was something where she could grow a successful business.

It’s clear that Rhonda leadership is very much about overcoming the challenge. And learning from the failures until you get it just right. Most importantly, she reminds all leaders that we need to know when to get back up, understand how to get back into our work and ultimately start again and start again until we get the vision just right.