How I Became...

Kelly Yefet (01:52.869)
Today, I am thrilled to have Erica Pearson as our guest. This episode is gonna be a little bit different from the typical entrepreneurial story where the entrepreneur is in the middle of the journey, but we'll dig into that and I'll have Erica explain her story. Erica is a multifaceted individual with a diverse background, having transitioned from a career in capital markets, testing out the startup life and a competitive athlete, which I'm curious to hear more about.

Having her entrepreneurial spirit, it truly shone through with the Vacation Fund, a fintech startup in Toronto from 2017 to 2020. And the Vacation Fund operated as a unique software facilitating employer matched vacation savings for employers, which was revolutionizing the way companies approached employee benefits. Currently, Erica serves as the Growth Account Executive at Sprout Social, bringing

her wealth of experience to the table and beyond her professional endeavours, Erica is a passionate about holistic mindset embodying a well-rounded approach to life. So join us as we delve into Erica's journey exploring her entrepreneurial ventures, her insights from the world of fintech, and your current role at Sprout Social. So welcome Erica, thank you so much for joining.

Erica Pearson (03:11.446)
Thank you for having me.

Kelly Yefet (03:12.105)
That was a lot of information. So maybe I'll start there and ask you to break it down a little bit and where you are today, how you got to where you are today, and a bit of your journey.

Erica Pearson (03:16.078)
Thanks for watching!

Erica Pearson (03:23.934)
Yeah, yeah, absolutely. Well, thank you for having me Kelly. Thrilled to be here. I always love meeting new people, talking through giving myself a chance to reflect on where I've been, which is always wonderful. So I think if I were to try to just summarize and like wrap my head around where I am today, so I consider myself an ex startup founder.

a past competitive athlete currently fully invested in my software sales role and really enjoying it while I also navigate early years of life as a working mom. So those are just some key components that have brought me to where I am today, but there's just so many things that I like to consider. I like to consider my 20s, my early career years, my like trial and error period that just showed me, taught me a lot of things about myself.

and showed me what kinds of things I need to feel fulfilled in my own life. So there's lots we can unpack there.

Kelly Yefet (04:28.105)
Erica, sorry, it's starting to cut out a little bit. I don't know if there's background tabs maybe open. I'm gonna try to quit some of mine on my end, but it captured everything. It's just a bit choppy. Okay. Okay, I think I closed everything. Hopefully we'll be better going forward, fingers crossed.

Erica Pearson (04:39.57)
Yeah, no worries. No worries. Yeah, I've closed pretty much everything on my side.

Kelly Yefet (04:54.297)
Okay, well, thank you for sharing everything and where you are today. Congrats on becoming a mom and navigating all of that. I imagine it's very difficult in the early days of it, but also very exciting to be able to have that new, very real purpose outside of work. I'd love to learn a little bit more about what your current role is and what kind of keeps you busy

with the work life right now.

Erica Pearson (05:26.622)
Yeah, yeah, absolutely. I think so. This is my first official software sales role in a way like my first time ever having you know, working for an established company, a publicly traded company in the tech space that where I have an assigned quota and I have assigned clients and I'm working on helping them solve problems and figuring out where

what their objectives on from a social and marketing perspective really is so that I can say, okay, do we have solutions to help you solve your problems? So I love that approach. I've never felt like, you know, like if you think of a salesperson, like the kind of person that could sell anything, like could sell anyone a pen, right? Like that's not me. I like to build relationships. I like to understand like...

where are people trying to get to and how can I help them achieve that thing that they're trying to get to. So that's been really interesting. The nice thing being in the social media management, like software space, is the speed of social is incredible. Like there's innovation, there's changes, everything just moves so quickly. And so being able to keep up to date with where the industry has gone, with where the technology has gone, and then how our clients are thinking about their business goals.

Kelly Yefet (06:21.945)
Yeah.

Erica Pearson (06:45.954)
just gives me an interesting perspective to say, hey, like I'd love to help you. Here's what I'm seeing from all of my other clients. This is what I think could be helpful. And this perspective may add to, I guess your strategies in, for example, 2024. So helping people solve problems and accomplish a goal. So that's been really interesting to figure out.

Kelly Yefet (07:09.545)
And just a quick download on Sprout Social and what it actually is, I believe it goes beyond just scheduling posts and things like that. Is that the...

Erica Pearson (07:24.774)
Exactly, exactly. So I always like to tell our clients if we were doing our jobs absolutely perfectly, you would never have to log into any of the social platforms natively. You'd be able to do everything from within our tool from both an engagement perspective, DMs, comments, responses, publishing and your content calendar, and then reporting, like being able to pull in all of the metrics you need to be able to understand, separate out your paid and organic results.

Kelly Yefet (07:42.917)
Wow.

Erica Pearson (07:53.054)
And then now within this past year, we acquired an influencer management software as well. And so getting a handle on what does the influencer space look like right now? What are content creators doing and how are organizations B2C or sometimes B2B hiring individuals to help get in front of them, right? Like it's a different world than when people used to just pay to put up billboards. Like how do you capture an audience's attention and understand what your audience needs? So from that perspective,

Like social, obviously, I have a love-hate relationship with social, right? Lots of us feel like we spend too much time on it, but at the same time, from a business perspective, I don't know where else you gather more insightful data from your customers.

Kelly Yefet (08:37.509)
totally and the interconnectedness of it all really allows as a small business or as a startup to be able to go from having an idea in your head of this is who my audience is to actually building that out and thinking through from the idea of who your target is to actually building out a target audience, your personas, your activation journeys. It's so incredibly helpful. And by building an organic and like

your organic audience and that meaningful insight gathering can become less about what you think and more about who's actually engaging with your content, which I think is never mind just like the organic brand awareness value of building organic, but also allows you to create a sustainable growth funnel through it.

Um, yeah, very cool.

Erica Pearson (09:29.33)
Yeah, absolutely. Absolutely.

Kelly Yefet (09:32.401)
So I also wanna talk about vacation fun, but before we get into like the nitty gritty of the evolution of the business, I want to understand a bit about your experience in entrepreneurship and how you went from, how you started that transition as an entrepreneur. Do you still call yourself an entrepreneur? What does that look like today?

Erica Pearson (09:57.49)
Yeah, I think it was interesting for me. And one of the things that is the craziest when I look back on it is just, it was something that was so outside of my comfort zone. It was so foreign to me. I did not grow up in an entrepreneurial family. I was not building businesses growing up. I was not an expert in the tech space at all. The only thing really that prepared me.

for a startup journey, I think, was being a competitive athlete and just working on constant progress, right? Like always having a goal, always working towards that goal, being able to get coaching and mentorship from other people. But besides being an athlete, I didn't really have anything that prepared me for it. So I was on a trading floor, I was in finance, I was making a good consistent paycheck.

Kelly Yefet (10:44.261)
Yes.

Erica Pearson (10:54.006)
My dad had been on a trading floor for 20 years, so I thought, okay, well, you know, you can make decent money and have your weekends for your family. So that was my mentality going into it. I thought, okay, well, that seems like a decent job. And I got there and I just said, like, I don't feel like I'm adding value to anything. I just, I started to feel like I wasn't doing enough with my life, if that makes sense. And so...

Kelly Yefet (11:02.57)
Right.

Erica Pearson (11:22.886)
I started getting really into all the stories and I was actually, I was reading stories on notable every day. I don't even know if, is notable still around? I don't even know. But I was reading stories on notable every day of young people starting companies and I thought like, that's so inspiring. Like everyone had a really powerful why. Everyone had a really powerful purpose or really powerful mission. And I thought, okay, well, you know, thankfully like I was in a position where

Kelly Yefet (11:32.865)
know either.

Kelly Yefet (11:42.733)
Right.

Erica Pearson (11:51.022)
I had saved some money, I wasn't in debt, I didn't have any real intense financial obligations, and I thought if I were ever going to do something, I just have to do it. If I'm gonna start a startup, I just have to do it now while I'm young, while I have fewer responsibilities and I actually have the ability to go all in on a project or something like this that I can throw myself into, but I wasn't willing to just jump in right away. So what I did was I took.

evening courses at BrainStation in Toronto, so Intro to Web Development, and then UX Design, and started to think through like, okay, what is it, like, what is the problem that I feel such a passion, such a need to solve? And then when I kind of came to that, and I said, well, I want, I really want to help people pay for experiences, like, I don't think travel should just be, you know, for the wealthiest, whatever it is, 5% or whatever it might be.

I wanna help people use their time, use their resources in life, their time and their money in the best way possible. And like buying stuff, like it's very easy to do, it's all over Instagram, it's everywhere, but if I can help people prioritize saving for moments that matter more than stuff does, then that would be really cool. I'd love to help people basically feel more fulfilled in their lives, right? Like big ambitious goals. So that's kind of how it started. And then like by doing those tech courses,

Kelly Yefet (12:52.493)
Mm-hmm.

Erica Pearson (13:15.146)
I was able to build out a clickable prototype just to show people the idea I had in my head and have people take me seriously. And then the biggest, I would say, a moment where I feel like I got very fortunate, like I was going out and networking everywhere. I didn't know anyone in the startup space, but I wanted to start to meet people. I kind of had wrapped my head around based on all my learning on how to start a startup and all the Y Combinator materials.

all the Sam Altman YouTube videos and whatever else I was watching, it was very difficult to start a tech company without a technical expert really invested with you. And so one of the places where I got lucky was meeting someone early on in my journey that was able to be my technical co-founder. And he could tell that I was passionate about it. I was just about to quit my job. I was going all in. And so finding him and having him say like,

I am capable of building this. I want to do this with you. Like that was a moment where I got lucky. And some people spend years unable to find technical co-founders. So that was a huge turning point for me to say, okay, like I'm able to sell this idea and the excitement behind this to someone that's capable of helping me build it. So that was kind of like an early win.

Kelly Yefet (14:33.273)
How did you feel about bringing a co-founder on? Because you have this idea, you feel really passionate about it, you're so excited. And then to bring on, were they a co-founder? Like to give up a bit of what you were building. And of course, like a percent of something is better than a percent of nothing. But I still would feel that there's a bit of, like I've got concern maybe of bringing in a co-founder.

early stage.

Erica Pearson (15:04.99)
Absolutely, absolutely. And one of the principles that you start with when you start to look into like how to start a startup and how to really get going is don't start solving a problem unless you're so passionate about it that you can't not do it. Like you have to solve this problem, but then also like the idea of doing things that don't scale at first. So the idea of trying to offer something to someone and have them pay for it.

without having built out this massive technical solution. So like, are you adding value? Is someone paying you for an idea or for what you're doing already without building out the entire product behind it? And from a technical perspective, that's a huge barrier, right, like the cost to build out a good technical product is not small.

So I had talked to a number of different tech agencies. I've talked to so many founders that have or have not had technical founders. And when this person that I brought on as my technical co-founder, we met and we kept talking for months before we had sort of agreed to anything. And so just being able to trust someone and say like, okay, I think...

this person wants to be invested with me. This person wants to put their time into this idea. This person wants to help me solve this problem. I think this is the best path forward. Like that just sort of, it came to me naturally enough over the months that we were talking that it seemed like the best path forward because the alternative was, you know, you can use an overseas tech shop, for example. You can try to find a way to...

to hack something together, but then at the end of the day, if you wanted to build a company that's actually scalable, if you wanted to build a product that's scalable, like a technology solution that can be leveraged all over the place across North America or across the world, that's extremely complicated. And somebody's going to have to, at the end of the day, unpack whatever someone overseas did at the beginning, right? So it was just going to be a massive time suck.

Kelly Yefet (17:21.109)
Yeah, it's, I mean, one of the things I want to talk about is luck versus like how luck plays a role in it. But as you talk about and sorry, how luck plays a role in it and the fact that you're mentioning lucky to maybe know to even consider that in the beginning is important. And I'm sure as part of BrainStation and all the learning and networking you did. But I was I do some growth advising and consulting on the side.

company that I was recently working with, they had exactly that non-technical founder, had someone overseas build everything and the company was doing really well and they were at a point that they needed to, you know, evolve the product quite a bit. And they had to invest almost everything that they had already invested and then some to completely move the platform, bring on a CTO, get the thing going. So.

Sometimes it's like, well, I just want to MVP and test it and learn in the beginning, and then we can spend the money down the line or do it right with an MVP from the get-go. So it's probably a huge value add that you even had that insight from early on. And then figuring out what are your skill sets and what are the CTO skill sets so that that's a weakness that you've already identified and someone else can own it, which brings me to the next question of

What were the, what did you own? What was your part? If there was the CTO, what did you focus on growing the product in those early days?

Kelly Yefet (19:12.953)
Did I lose you?

Erica Pearson (19:14.11)
Yep, there we're back.

Kelly Yefet (19:17.092)
Okay, thank you for the end. You want me to repeat?

Erica Pearson (19:19.682)
Yeah, no, I heard you say, so what was sort of your part? What did you own? Basically, what did I have ownership of in evolving the company, right? So I think the nice thing from our co-founder relationship perspective is like there was a very clear divide in whose expertise was what, right? So from my perspective, and I know founders that have done things differently and been successful, but for...

Kelly Yefet (19:27.853)
Right. Yep.

Erica Pearson (19:47.33)
for the idea I had and what we were trying to bring into the world, I just spent three and a half years just selling, just selling the idea, selling the concept to potential new hires, selling this idea to investors, selling the idea to companies, to potential clients that we wanted to bring on. Like my role was fully just all kinds of outbound sales. How can I convince people?

that we are the people to bring this concept into the world and this is why it's important that we do it. So from a fundraising perspective, from a revenue generating perspective, it was just, and CEO really did feel like chief everything officer in a way because you kind of have to have awareness at least of what's going on the product side. And my co-founder and I were very good at communicating between each other.

which is wonderful, but like, you know, he was a full stack engineer, didn't wanna do the front end development stuff forever. So I ended up bringing on someone there. And then even the user experience design stuff, somebody that had more of that eye to say visually, this is where things should go. And this is how the user experience should flow or operate. This is how we're gonna help our users accomplish their goals. So it was...

pretty clear what things I could help with or at least talk through. And I wanted to have awareness of everything that was going on. But for the most part, like I was never in the same place any two days in a row. Like I was at so many events. I was meeting someone new all the time, whether it was from a partnership perspective, from an investor perspective, from a client perspective, from a mentorship perspective, I needed so much coaching because I had no idea what I was doing.

Kelly Yefet (21:26.853)
Great.

Kelly Yefet (21:38.753)
which even if you were prepared to be an entrepreneur, that's a theme that I hear as no one's ever prepared. It's, I imagine, I'm not a mom, but I imagine it's like having a kid, like you can read every book, you can learn everything, but it doesn't really matter until you have, you know, that baby and it's the same thing with a baby or the baby of your business, like it becomes everything to you. So you put in every ounce of your being to make it work. And you did give it your all.

I know that you ended up quitting your full-time job and you were prepared to go two years jobless to pursue this venture. What was that transition like for you? At what point did you say, okay, this is it, I'm going full-time to build vacation fund?

Erica Pearson (22:24.986)
Yeah, it's a great question. I think so I had been moved between different various desks on the trading floor and then I was moved into a specific role and it was something that it just I mean I wasn't loving it, I wasn't enjoying it and I'd been taking the part-time tech courses in the evenings to be able to say okay like I'm starting to understand the steps that I need to take to make this possible.

Um, and so it was one night where I, it was, it was a night where I was expected to sort of stay and work until midnight. And so I wasn't able to go to my very last UX design class. And so I was, I was just thinking to myself, if I'm going to do this, I'm going to have to leave my full-time job. Like there's no way of pursuing both because the full-time job was more than a nine to five. Um, so.

I mean, thankfully I wasn't leaving a job that at the time I had been enjoying. It had been challenging to me. It was long hours. And so I said, like, now is the time. I've done as much homework and preparation I can in advance of leaving. And so thankfully my manager at the time was very understanding. Like, yes, if you feel like this entrepreneurial drive, like you have to go do it.

but asked if I was able to stay on kind of on a part-time basis for two more months. One, it helped me, it was a small team, so it helped them transition a little bit, but then it also helped me continue earning a paycheck for a little bit longer. So that was two months. And then from there, I ended up just getting into, like I was just trying to find someone to give me some kind of playbook or roadmap because I really had no idea where to start.

Um, and so that's when I came across founder Institute as like a pre accelerator, an idea stage accelerator, a, you have an idea, let us tell you why it might or might not work. Um, and so that was a weekly commitment with, you know, commitments, I have team meetings during the week and stuff like that. It was three months, but you would go to these founder Institute sessions once a week for three hours, pitch your idea in front of people that had experience that were successful. Um,

Erica Pearson (24:48.13)
in the startup space, in the tech space, and they would evaluate sort of your pitch, your idea, and give you their feedback. Which was just like, that was the greatest period of transition for me, because I got to hear from their perspective, from their expertise, what would make this really difficult, and what would be the motivation to keep going, because it could actually be possible.

Kelly Yefet (25:13.113)
From that time and the feedback that you got in the Founder Institute, is there anything that stuck with you throughout that journey? Some of the key learnings or key pushback that you continue to reflect on?

Erica Pearson (25:28.958)
I mean, some of it, and this is not as much high level, but it was just specific, like just general industry knowledge because I upfront was like, oh, I'm just gonna help people create kind of like a savings tool, right? Like a wealth simple, but just for people's travel goals. And to me that sounded like, oh, it should be straightforward. People have done this kind of thing, you know, over the past decade, it should be straightforward. And the feedback that I got,

from like over and over and over again was based on sort of the lack of experience and the lack of industry knowledge and not having run any kind of company in the past. And people just kept saying to me, do not start a B2C FinTech company in Canada. Like don't do it. The banking system is a monopoly. We don't have the population for it. Like either take this idea and go to the United States and figure out their banking system.

or figure out how this is actually a B2B offering. And that, like I kept getting that feedback and I was like, no, well, you know, like everyone tells stories about how people told them their idea was crazy and it was impossible and whatever. And so you have those moments where you're like, is this just that scenario? Is it just somebody saying it's impossible, but then I'm gonna prove them wrong? But that feedback was consistent enough that I said, okay, like.

maybe trying to navigate the Canadian banking system to create a separate niche savings tool isn't necessarily the path to success. So it was just, I mean, when you hear something enough, you really, it just makes you start to believe it.

Kelly Yefet (27:09.277)
Yeah, and what did you do with that information? Like how did that transition then to B2B occur?

Erica Pearson (27:17.454)
So it was a successful tech CEO in Toronto that at one point I was talking to, because they gave you a chance to network after, you know, everyone goes up in pitches and receive some feedback and then you kind of are reflecting on it. And then like it was an opportunity to go out for drinks after with the people that had just given you the criticism. And so I was talking to this tech CEO in Toronto and he said, you know, like I have a company full of millennials.

that say they value their vacations and value travel and time off, but a lot of them aren't taking it. They're not taking their vacations. So he said, like, what if, what if I just started to, you know, add money to their vacation fund as a company perk? And I thought, well, that's really interesting. Like that, that is the B2B angle. And so it didn't, it took a while for that to kind of just

for me to sit with it and for me to then say, okay, if a company is contributing towards employees vacations, what does that look like as a portion of compensation? What does that look like if it were like an RSP matching program or a 401k matching program? Like, what could this look like as a B2B offering? And that's kind of how it started, how it kind of turned into B2B.

Kelly Yefet (28:44.161)
And what a great, I mean, I hear that and I'm like, I love it because now my company is helping me pay to not work and I'm sure that there's some data, some story that you can tell on the business side that listen, you have these employees, they're not taking their time off and yet if they take their time off, maybe, I don't know what the stat would be, but like they're more productive when they come back or there's new ideas and you have...

companies, I don't know, new innovation, who knows? So I feel like on both sides, there is a value prop there. So what happened? Where did the story go?

Erica Pearson (29:24.266)
Yeah, absolutely. Well, it's funny. It's funny because like, it sounds so obvious now, then I've obviously gone through so much research around how much more productive employees are when they come back from the vacation. But the biggest value driver for the companies that did end up adopting it was and it's hard to measure without, you know, years of running the program successfully. But it was ultimately retention, like your employee is likely to stay there was something crazy like

18 months longer at the company if they've taken at least a one or two week vacation a year. Right? Like if people go too long without a vacation, they're just one day going to be like, that's it, I'm out and they're going to leave. So it took us several years to get to this point, but there was two different types of companies that were adopting vacation fund as a strategy. They were either using it to solve a problem of like burnout prevention,

Kelly Yefet (30:19.619)
Yeah.

Erica Pearson (30:19.682)
So really trying to help people say like, we need you to go on vacation or else you're not gonna be here as long as you think you're gonna be here. So like this is what's best for you and what's best for the company. So burnout prevention or for companies that were really good at encouraging people to take their time off already and employees were very happy. It was just another sort of icing on the cake way to attract talent. Is that the time pre-pandemic like the tech market was still very hot.

Kelly Yefet (30:27.522)
Right.

Erica Pearson (30:50.144)
And so being able to say we're going to win you over because we're going to invest in your annual vacations, that was that was powerful.

Kelly Yefet (30:59.09)
Yeah. And where did it go from there? So what were some of the hard decisions that you had to make and what did that evolution look like?

Erica Pearson (31:08.522)
So because I really valued some kind of playbook or instructions or somebody like nudging me in the right direction, I ended up doing another accelerator. So I did Techstars in Chicago, which was just sort of, you only got into Techstars if you had someone technical that was able to help you like actually build out the platform. And then they, Techstars invests in the company, which is very helpful in the early days, especially when you're

Kelly Yefet (31:20.953)
Yeah.

Erica Pearson (31:38.342)
operating based on nothing. And so I went to do tech stars with my co founder, we moved to Chicago for three months to say like, let's just go all in, let's accept obviously the investment, let's get more mentorship. Now, what I did not realize at the time, is that it would send us backwards in a way, because our existing

We had a handful of paying clients saying, like, it was, it literally started as a type form survey where I went into a company, asked employees what vacations they were saving for, coordinated with their HR side to do a payroll deduction so that employees are contributing and then the company is technically matching. It was a very manual process. It was a very much a version of like doing things that don't scale upfront.

Kelly Yefet (32:35.114)
Right. Which is where you have to start sometimes.

Erica Pearson (32:36.266)
But exactly, exactly. Now the reason that became a problem is because working with so many different kinds of partners from a payroll perspective, from a banking perspective, I ended up splitting my resources and priorities between trying to navigate both the Canadian banking system and the American banking system at the same time. That was a big mistake.

Kelly Yefet (33:03.959)
Yeah.

Erica Pearson (33:04.074)
It was a big mistake. And so I needed to have focused just somewhere. And really, like, I probably should have just focused on maybe coordinating processes with one payroll provider. The challenge with doing something like that is, and I'm sure somebody at some point recommended that to me, but the challenge is, oh, well, like, then I can't go after just any company. I would be limited to the companies that are served by that payroll provider. And so as much as it would feel like a limitation,

that's ultimately what it came down to is we were trying to do too much at once. We were trying to figure out how to sell this into HR teams and company leadership as a great idea for their employees. So we were navigating the HR tech space, the HR sort of sales world. But then we were also trying to use the value of, okay, well, what we're really doing is we're going to end up with by knowing where people want to go, what time of the year and what their budget is.

we are creating lead gen gold for the travel industry, right? Like if people have a bucket of money sitting aside and they're gonna tell you exactly where they're gonna spend it, and you can then put offers in front of them that are aligned with their needs. So we were trying to figure out the HR space, the travel space, and the financial institutions all at the same time. Like that was not smart. That was way too much to take on at once. So.

because it was just too much to figure out. And we were constantly, I mean, we'd raised half a million dollars, never from venture capital, because they thought this was more of a feature of a bigger platform rather than its own standalone platform. So, but half a million dollars gets spent very quickly when you're growing a team and you're trying to scale a product. So.

Kelly Yefet (34:45.515)
Interesting.

Kelly Yefet (34:54.373)
Totally.

Erica Pearson (34:57.246)
So we were very quickly running out of money. We had maybe three months of runway left when the pandemic hit. And when the pandemic hit, no one was picking up the phone anymore, right? HR is trying to figure out how do we just, you know, have employees continue to work during a pandemic. And everyone's wondering, well, is travel gonna be a thing again? When does that happen? And people are just trying to, people are just, you know, alarmed by, like we've never seen something like this happen before in our lifetime.

Kelly Yefet (35:12.814)
Yep.

Erica Pearson (35:28.978)
And so it really just ended up being like, okay, nobody's picking up the phone anymore. There's a bigger thing. There's a bigger area of concern. And so what I always tell people is like to summarize the reason why it failed and timing and luck can be a factor. But vacation fund as an offering was viewed as an expensive nice to have by most companies and expensive nice to have does not does not.

Kelly Yefet (35:51.395)
Right.

Erica Pearson (35:56.702)
warrant a phone call or a meeting during times of crisis or a time where things feel more urgent. So it was just, it was a natural time for me to shut down something that just hadn't been establishing itself fast enough. I just, I wasn't getting to where we needed to be quickly enough.

Kelly Yefet (36:17.485)
Yeah, it's hard because expensive, nice to have, I hear you, but there probably over time would have been a story about what you were talking about, the retention, the thought, but also during COVID, no one was traveling. No one even wanted to think about traveling. It was like, you know, if anyone went on a road trip, you'd be like, oh my God, what are, how dare you, right? Like the mindset of travel also shifted. So

I can't imagine how you were feeling during that time. How did you officially call it quits? What was, like, how did you feel emotionally about it? How did you, you know, work through all the process? And I know you mentioned you like the playbooks or the playbook of it, but what was that experience also while you're going through a pandemic yourself? Like it's scary as an individual too.

Erica Pearson (37:12.834)
Yeah, yeah, absolutely. So, I mean, by the time the pandemic hit, so we were we had been generating revenue, but we were operating at a significant loss. By paying our employees, we were running out of money fast. And there was no indication of how long any of this was going to go on for. Right. So, so at first, in my mind, I thought we've built a great team, we've got a great idea, this can be valuable.

Kelly Yefet (37:23.918)
Right.

Kelly Yefet (37:31.897)
course.

Erica Pearson (37:40.586)
And like basically the venture capitalists were ringing in my head saying, this could be a really interesting feature, a part of a broader platform. And so in my mind, I thought we've got a great team. We've accomplished enough to be valuable to somebody. Let's go have acquisition conversations. Let's go talk to a payroll provider and say, what if you could offer this as an, a unique incentive, a travel add on.

so that the company's like the payroll space is very competitive as well, right? Like how do you make someone stick to your payroll provider specifically? I realized that it's sticky, but like when, when a company is starting, you know, like getting them onto your payroll product, like that initial win them over is worth so much. So having learned that, I was thinking, okay, let's talk to payroll companies, let's talk to other broader benefits companies, let's talk to.

anyone where this could either be a unique differentiator for them or they have a similar mission because we're very passionate about the problem that we were solving. So the first few months, I mean, I feel like in a way I blacked out for a lot of it. Like I was kind of cohabitating, my husband and I were cohabitating with his parents at the time. We were in a remote location.

We were just like, I was hardly processing what was going on with the world. I was just thinking, well, we couldn't stay in our small condo in Toronto or else we'd probably both go insane. I'm sure lots of people felt that in Toronto. So I was grateful at least.

Kelly Yefet (39:15.399)
We went through that too, it was a lot.

Erica Pearson (39:19.254)
Yeah, exactly. A small space during a time of crisis. You're just like, I need a change of scenery. So I at least, we were at least able to get out of the small condo. But like, yeah, any calls that I could take, I was just trying to talk to our investors saying like, this is where my head's at, you know, like, nobody, no, investors weren't going to give us new money when they didn't even know what the state of the world was looking like. Right. So as much as people wanted to help us and wanted to motivate us to keep going.

no one really gave me that hard of time by saying like, okay, let's figure out what's next for our existing team. Let's figure out how to take what we've done and make it valuable to someone, right? Like we knew we created something of value. We had paying clients, we had some great partners. So how could we make this valuable to someone else? So that initially in my head was like, okay, it's not dead. It's just

becoming like the direction is just changing. It's just going to become a part of something else. And so that's actually how I the first role I took because I also hadn't been earning a paycheck for several years. And when the world is in crisis, you just want some level of comfort, right? I was like, I need somebody to give me a paycheck again, because I'm tired of, you know, not making any money watching all my savings go into this company.

Kelly Yefet (40:36.725)
Right. There's enough scary things right now and not having that sort of stability probably wasn't one you wanted to add onto the list.

Erica Pearson (40:46.318)
Exactly. And it's like, and it's interesting because there's so many there's so many entrepreneurs that will talk about this, I think. And I think, Elon Musk talks about like, you have to have a very high pain tolerance to go through times like that and not basically find like reach for things reach for feelings of comfort, reach for something of comfort. And I was reaching for, I want to pay check now, like I'm tired of not making money. And so that's how I ended up at League.

which is a tech startup out of Toronto. So they were doing something in the employee benefits space and doing kind of like lifestyle spending accounts. And I thought, well, they do a version of that a lifestyle spending account is kind of like just a different version of vacation fund. So this is something that would be possible to spin up. And I was talking to the founder and he seemed at least inspired by what we had done so far and like wrapped his head around the idea that

this could be a thing. And so in my head, it was kind of like a way to say, I'm not quitting, we're not shutting vacation fund down, we're just, I'm going to a place where I can earn a paycheck in the meantime, and maybe what we've been working on could become a part of league. So in my head that was, and I had many other acquisition conversations, but it was also like a time where not a lot of people were going to.

make any dramatic business decisions because there was just so much uncertainty, right? So for any business taking any financial resources and putting it towards something related to travel when we didn't know when travel would be a thing again was just it was going to be considered a risky decision. So that's how I ended up at League and then just being at League it became clear to me pretty quickly that

as much as vacation fund is a great idea and lots of people were interested in it, that was not necessarily an area of focus. Like League wasn't going to go out of its way to build all of these travel partnerships that we had on our radar, that we had on our road map. So League is still around, still making great money, but it wasn't going to make sense for them to build in a vacation fund, at least not while I was there.

Erica Pearson (43:10.502)
So it ended up being a slow progression for me to kind of wrap my head around. And people have still reached out within the last year or two saying, hey, what's left of vacation funds? Like, what if we technically like, acquired what's left? But we from between myself and my co-founder, we agreed at some point, we just kind of had to shut down the technology and to integrate the technology into someone else's technology, it would cost more than it was worth.

Kelly Yefet (43:38.105)
Hmm. Do you have visions or hopes of bringing it back to life at some point or thinking of another, you know, problem area that you might want to explore in the future? Or is that part of your chapter complete?

Erica Pearson (43:55.622)
Um, sorry, it cut out for a minute there. Um, was that, sorry, go ahead.

Kelly Yefet (44:00.781)
So yeah, I was just gonna ask if the entrepreneurial if the vacation fund itself, are you going to explore that as an opportunity in the future now that we are more in an endemic state and the you know, all of that is done or Do you have other entrepreneurial like aspirations for the future.

Erica Pearson (44:24.43)
So I think I definitely see my entrepreneurial side coming back to life in the future. What did not resonate with me at all from the vacation fund journey was fundraising. Like I can't like the word fundraising gives me anxiety. The idea of trying to raise money for something that wasn't fully figured out that I hadn't already proven could work just gives me a lot of anxiety and I can't believe I did it for more than three years.

trying to convince people to give me money for something that was not guaranteed to succeed. Like as a, like I think I'm, I am despite the fact that I left a paycheck to go do something, you know, different, crazy out there, I'm relatively risk averse. So that was like a big, like, and now having like, having a family, having a child at home, I'm like, I'm not gonna go do that. So I would go with a bootstrapping approach for sure.

But that just changes how you approach so many decisions. So based on my areas of expertise, I don't think I would start a tech company Just because especially now seeing what the Sprout Social has been around since 2010 Seeing like a very successful, you know Tech startup that is now a publicly traded company Like I can't even believe all of the good decisions that they've made. I'm in awe

with leadership at Sprint Social because they've just made so many good decisions, but there's definitely luck and timing involved. And that's just a gamble that I'm not necessarily willing to take, especially just being at a different stage of my life. So I'm honestly in a different kind of direction of entrepreneurship. I'm just, I'm fascinated by content creation.

So I mentioned I have a love-hate relationship with social media, but when it's used in the right way, it's so powerful, right? Like we have access to more people and ideas and information than ever before. Like sharing perspectives can help people see things differently or embrace a new idea, and it's just so powerful when that happens. So I'd love to be a part of the group of people that you know really try every day to use social platforms for good, and I get inspired by things that I see or hear on social media every day.

Erica Pearson (46:43.454)
if I could do that for others as well. Like my brother's a full-time YouTuber, so I get enough exposure to, you know, the content creation space, and there's so many different ways to use it, and so many different areas of passion that I have that I'd love to learn more about and then talk to people about. But yeah, I think that would be more in the direction of my future.

Kelly Yefet (46:55.289)
That's pretty cool.

Kelly Yefet (47:06.677)
It's funny that we kind of led the conversation here this past weekend. I was at my brother's place, he lives up north, and we were having a full debate about whether content creators today is today's version of an art form. Like, are they artists? And I was arguing, absolutely. Like, even if there's a lot of iteration within the craft, it is, you're holding the whole world's attention and you're creating...

You have to be so on top of it, so with the trends, so much research into each piece, which is, it's just as, you know, it's so difficult. It's a full, it can be a full-time job. So I think it's a really fascinating space that is still, I think, in pretty early days and gonna grow more and more and become so interesting, especially now that we're seeing the.

boom of AI and that the everyday person is using it and seeing how that's starting to get into excuse me integrated into content creation. It's very interesting. One one of the things I want to ask as you were talking about your thoughts towards entrepreneurship is this being risk averse or being comfortable leaning into risk and for individuals listening to the podcast. Would you say that if you are

If you have an aversion to risk, it will be a detriment to you being an entrepreneur.

Erica Pearson (48:38.542)
I don't think so necessarily because there's just so many different ways to be an entrepreneur. And so like what I would say to people is based on the timing in your life or based on the amount of risk that you're willing to have, like none of that should stop you from necessarily pursuing an idea where you're like, I can't get this out of my head. I have to do this. I would just say like, you like regardless of whether you go all in and quit your job and do everything like 18 hours a day for seven days a week.

You just say, okay, I'm gonna start working on this thing on the side a couple hours a week and see what it becomes. Regardless of which path you take, you end up experiencing trial and error. Obviously one path gets you through the trial and error faster than another, but at the same time, either way, it's experimentation, right? You're figuring out what works for you, what works for your idea, what works for your customers. So there's nothing wrong with starting small.

And there's so many posts and there's so many things that inspire people where it's like, this person didn't start, like Vera Wang didn't start until she was, I don't even remember the age, but like so many posts where it's like, age or timing should not be a limiting factor. Like you have time. I think the big thing to remember is like, just make sure you're not doing something just to achieve the end result.

Like just enjoy the pursuit of whatever it is that you're working on because regardless of whether that thing turns into something or not, right? Like vacation fund doesn't exist today, right? Like it doesn't exist. Does that mean I wasted three and a half years? I don't feel like I did because it changed me so much as a person, right? So like if you are pursuing something that you're excited about, then it'll just like, it'll have an amazing impact on.

your perspective and what you're able to accomplish in various areas of your life. So I think, I think just telling people like, regardless of your risk tolerance, like there are ways to get started and there are ways to pursue things that you're really passionate about. And you just have to sort of put your own parameters in place because your risk tolerance is going to be very different than someone else's.

Kelly Yefet (50:50.933)
Yeah, that's great perspective. I have a million more questions for you, but I know we're getting close to the end and I want to ask you about myths that you would dispel for future founders. I think when we start in entrepreneurial journeys, we're told a whole host of things and a lot of them often turn out not to be true. So if you were to think back as a founder, what are some of those myths you would dispel?

Erica Pearson (51:20.31)
Yeah, it's a great question. And like, I find, I do find that I was thinking a lot about this question because I kind of wanted to prepare myself, but I find that question so tough because everyone's experience is so unique and so different. So I could say, hey, this is a myth. It might've actually been true for someone else, right? Like, so I think for me, the idea that you will ultimately be happier.

Kelly Yefet (51:39.597)
Great.

Erica Pearson (51:49.258)
and more at peace in your life. If you are pursuing something, pursuing an idea, solving a problem that you're so, so passionate about rather than having a full-time job. Like if I look at that, I mean, there's a time and a place I think, but it's not necessarily true. And to put that into perspective, because it was so foreign to me, this idea of just doing something on my own and creating something from scratch.

I wanted to like, you know, as soon as people started to invest in the idea or like give me their time to pursue this thing, I started working 18 hours a day, seven days a week, because I felt like I owed it to them. I'm like, if somebody, somebody invested in this thing that I'm doing, I owe it to them to put my heart and soul into it and all of my hours into it. And I ended up hospitalized with like neurological issues, right? Like that's, that's not okay. That wasn't the happiest version of me. I thought.

I was like, oh, well, I'm working on something I'm passionate about, like, that's the ultimate goal, right, in life, that's the ultimate goal, is to do something, go all in on something that you're creating from scratch. And it wasn't, like, that ultimately was not the most successful I've ever felt when I'm lying in a hospital bed being like, my health has really been sacrificed here. Like right now, even, right now being a pregnant mom of one, having a nine to five job.

and being able to feel like I'm investing time with my daughter, like this is the most successful I feel like I've ever felt. And this is a full-time job where like, at least I like the job that I'm doing, but I think the feeling of, oh, like being able to create something and run towards it is the most successful you'll feel, that didn't end up being true in my case.

Kelly Yefet (53:23.906)
Yeah.

Kelly Yefet (53:41.513)
I know we didn't get into that part of your story, but whoever's listening, I highly encourage you. I know Erika has some YouTube videos about this experience, so I highly encourage folks to go listen to that. But a lot of what I hear in this myth section has to do with this in a way of like...

you can have work-life balance, you can put parameters on, and I think everyone is going to do it in a different way, but I get that feeling of people aren't investing in you as an individual, so you feel like every waking moment, every second needs to go back to the business, because otherwise, are you as passionate about it as you thought, or are you giving it everything to make it work? But it's really important that

you have to be healthy to run the business. You can't run it from the hospital bed. So I'm sure that was quite a rude awakening for you to go through that.

Erica Pearson (54:45.17)
Yeah, yeah, exactly. Well, and yeah, I think I think it's hard because sometimes it's glorified like all of the sacrifice that a lot of successful people have put in to get to where they are. And, you know, like, you just have to wrap your head around everyone's journey is different. And people have different levels of pain tolerance. And some people are okay with spending a month sleeping under their desk in the office because they want to spend every hour working. But

That doesn't have to be everyone's version of entrepreneurship. That doesn't have to be everyone's version of getting to where they're hoping to be.

Kelly Yefet (55:17.314)
Yeah.

Kelly Yefet (55:24.101)
Totally, and it's almost like the, I mean, the sleeping under the desk. It's a visual that I'm getting. I don't know if you've read the Elon Musk biography by Walter Isaacson, but that's exactly what comes through to me of this. Nothing else in your life matters except for your business. And that can be true, and maybe that is your pain tolerance, but it absolutely doesn't have to be for you to have a successful business. And I think more and more we're starting to see this health and wellness approach.

become part of the story, which is so important to know that you can do it both ways.

Erica Pearson (56:01.434)
Yeah, yeah, absolutely.

Kelly Yefet (56:03.793)
My last- oh sorry, go ahead.

Erica Pearson (56:06.666)
No, no, go ahead.

Kelly Yefet (56:08.417)
I was gonna say my last question for you. As you know, the podcast is called How I Became and I wanted you to name the episode. So if you were going to say how I became fill in the blank, what would you name this episode given everything we've chatted about today?

Erica Pearson (56:25.914)
I think, I know we, yeah, I think something along the lines of how I ended up becoming or how I became a happy, balanced working mom. Because I honestly, I honestly growing up did not know if that was possible. I did not know if by the time I got to the stage of being a mom, if I'd be able to feel like that idea of, oh, women can have it all. And reality is, it's really hard. And there's so many things. Like it just has to.

Kelly Yefet (56:44.889)
Yeah.

Erica Pearson (56:55.658)
You have to figure out what works for you at various stages of your life. But right now, thankfully, after one year of being a working mom, thank you, thank you. Like this year, I felt like a happy, balanced working mom. And I thought, I didn't know if this was possible. So I'm extremely grateful for that. My second will be born next month.

Kelly Yefet (57:05.605)
Congrats.

Erica Pearson (57:21.318)
and we'll start the chaos all over again and then we'll see. We'll see if a year from now or two years from now I feel the same way, but for now, for now I'm in a good place.

Kelly Yefet (57:21.445)
Oh.

Kelly Yefet (57:25.87)
Yeah.

Kelly Yefet (57:29.318)
Absolutely.

Kelly Yefet (57:34.189)
That's an amazing title and amazing end to this episode. Erica, thank you so much for coming on, being so vulnerable and sharing your story. I really am excited to release this episode and have everyone listen in. And that's everything for today.

Erica Pearson (57:51.854)
Thanks, Kelly. It was wonderful to chat.