Podcast: Interview with Ryan Pfleger - CEO of PayWhirl, Inc.

Join us as we sit down with Ryan Pfleger from PayWhirl, Inc. to discuss personal mindset, company culture, cryptocurrency, and working with a distributed team in the midst of a global pandemic.

Luis: all right so hello and welcome to the Sendlio podcast my name is Luis

Brandon: my name is brandon

Luis: and today we have Ryan Pfleger from PayWhirl. How you doing, Ryan?

Ryan: i'm doing great thanks for having me

Luis: alright thank you for being here. Why don't you just give us a little bit about yourself - you know, tell us who you are - what your business does and where you're coming from

Ryan: yeah so as you mentioned my name is Ryan Pfleger and i was born just north of Seattle, Washington. I grew up here and ended up going to school in Santa Barbara, California where I went to UCSB originally and then transitioned into a film program at a school called the Brooks Institute in Santa Barbara and I eventually transitioned my major from film to digital media and ended up working on software projects. I met Brandon along the way and basically our business PayWhirl - which is our main business - we actually have a suite of apps now but our main business PayWhirl focuses on e-commerce tools. And our goal is basically to make subscriptions easier for merchants. So we focus on recurring billing and recurring payments specifically and we integrate with a bunch of different e-commerce platforms and provide merchant tools that make it easy to manage subscriptions and bill customers on a recurring basis so most of our software is all B2B working with other businesses

Luis: nice

Brandon: yeah awesome. So yeah so what do you do to prepare for the day? Like how do you get your mind right and how important is your mindset to your business?

Ryan: so for me it's simple- it's pretty much coffee. Straight to the coffee pot that's the first thing i do pretty much every day. You know the kids are we have two little kids and they're up early so we you know fend them off as long as possible and then straight to the coffee pot. And i usually try to take, you know, 30 minutes in the morning and just kind of scan emails and you know, make sure that I at least know what's coming for the day. But yeah coffee is the key.

Brandon: You doing the Keurig? Or you back on the regular coffee pot?

Ryan: Definitely not a Keurig. i've got just a drip machine currently but i do have something special on order which is back ordered. It's a new machine called a spin that actually spins the beans and and uses centrifugal force to percolate the coffee so pretty excited about that if it ever ships it's
been ordered for a couple months now and

Luis: oh man just back ordered?

Ryan: yeah i'm patiently waiting so…

Luis: goodness

Ryan: i'm pretty excited about that. That should definitely help my mornings - at least i hope so

Luis: oh man - I can understand that. Coffee for me is crucial. It's a lifestyle and it's just something that
if i don't have it during the day i kind of go nuts without it so

Ryan: yeah I - I always shut off by about you know 11, 12 but i it's it's a requirement for sure. Yeah usually with mindset you know it's important for sure. You know, being positive and and enjoying what you do is obviously really important and I'm lucky because I do enjoy what we do. We've been doing this for almost eight years now in various aspects with different apps and things and you know i'm lucky. Got a great family and I get to work from home. i was actually doing that prior to you know the COVID situation.It's a good fit for me and we've got a great team so you know just having people behind you that support you and you trust and being able to build on that having a good mindset across the
board for the whole team is definitely a key part of our business.

Luis: So let's stay on that for a second because that's actually the next thing we wanted to go into you know company culture is such a big thing. How you work and interact with your team is super important. What do you believe in as far as company culture? Is there like an overwhelming theme that you have? How do you like to interact? How do you like your personnel to feel about you? could you give us a little bit of insight on that?

Ryan: yeah so our team is actually kind of interesting. We started this business and it was literally in a bedroom, you know, grinding.And we've slowly added members over the past eight years so we have an
actual team. Everybody that works on our team currently is a friend and has a good attitude. I actually shared a dorm suite at UCSB with our key support manager, Larry, so we've been friends since college and you know pretty much everybody including our developers we've met through other projects and just had a good relationship with. We really do use tools every day to keep the team together. We use Slack - it's probably our number one tool - and everybody uses Slack to communicate. We have you know giphy turned on in there so it stays positive and light and everybody, you know, can laugh throughout the day. Yeah so attitude is kind of important for sure and probably our biggest factor when it comes to the team.

Luis: Do you think that like that concept of friendship - is it really crucial for making the business run better or do you think that it kind of, you know, it can create some pain points? Because obviously friendships are so dynamic, you know, so how do you balance that in the workplace?

Ryan: Yeah good question. You know it does have challenges sometimes. You know professionally there has to be a bit of a wall up. But for the most part you know because we're friends or have become friends even through just working on the business we really know each other and we know
what our buttons are and each other's buttons are. And there's been definitely learning experiences along the way. I'm not gonna lie like we've had, you know, we've had ups and downs. And sometimes you tend to take things more personally maybe because they're a friend but at the end of the day it's you know for me it's you know even though it's a business it's kind of friends first. And one thing that contributes to this too is that we've been bootstrapped since day one so you know we don't have constant pressure from a VC or other investor to really add an additional level of stress and management. Like we run this business ourselves and we take a real team approach to it. So I feel like we're able to work through most issues that come up. And we have had some blow ups and some things but we usually just get on a call when that happens and and everybody syncs and
rips the band-aid off so to speak and we're able to work through issues like that.

Brandon: cool so i guess so the team's distributed. So are there any sort of challenges with the distribution of the team or do you feel like that's a better way to work than in an office? You know there's
there's competing ideas around that

Ryan: yeah you know when we started, as you know, we had an office in downtown Santa Barbara and we were small then. We've had an office here in Seattle too for a little bit at times but honestly with all the tools that have come out in the last few years, it's easy to manage, you know, you have tools like Slack. We use intercom for the customer side of things so you know that that aggregates chat and email into one place. You know, there are times when i feel like we should do more video calls like we just kind of rely on chat and things can be a little bit removed when you do that but it works really well for us we've been doing it since - gosh - what 2015 really or i guess no 2016-ish probably is when we made the full transition across. And it took a while to find the tools, right, when we were just using email
and other you know traditional communication methods it wasn't as effective. Now that we have the right suite of apps to support it, it makes life a lot easier you know - Zoom, Slack, Intercom, we use a project tracking software called Pivotal that's - it's awesome we've used it since day one at the business. And i think you know getting people up to speed on those tools is a bit of a curve but then once everybody's got it - it's just a set process everybody knows where they need to go. And then we, you know, we do check-up meetings at least once a week. I do a development meeting on Wednesdays with our lead developer, Dan, at PayWhirl and I communicate with Larry, you know, four times a day usually who's the head of customer support and he also has calls with other team members and they're usually short and sweet. It's nice - we can screen share within Slack so if we need to show something you know it's not like it used to be you can just pull up your screen and click a button and you're showing, you know, whatever the issue is right there and then. Which is you know it's just not the challenge it used to be. I think you know post COVID a lot of businesses are going to stay in this model and I've heard that large companies are adopting it and allowing you know people to stay remote whereas that wouldn't have been an option a couple years ago. So it's been interesting to see how that
how COVID basically kind of forced it so to speak on businesses and now it's being adopted widely you know. I think a lot of these SaaS applications that help teams, you know, manage and manage their products and communicate are doing better than they've ever done before and I don't see it slowing down. I think the market's gonna grow for years to come.

Luis: yeah not only to mention like the cost of your bottom line will go down significantly when you don't have to have a physical space and everybody can kind of be in their own

Brandon: yeah just that office building alone

Luis: yeah that's huge cost just to run that

Ryan: You know it felt weird we you know when we first started PayWhirl, we pitched to some VCs and you know they kind of asked us about company culture and and what the office was like and even back then we weren't - we didn't have an office and it felt a little taboo. Back then to even mention like oh we're distributed but now it's it's you know it's widely accepted.

Brandon: you don't have to be ashamed

Ryan: yeah and you know there's no fear around it anymore. i feel like back in the day you had to have an office and you know 100 employees in the same location to be considered to be you know effective

Luis: legitimate

Ryan: but now they don't even look - yeah legitimate and they don't even you know balk at that question anymore.

Brandon: awesome all right so going back to, you know, the team itself. What do you think is more important in a team member - skills or attitude? I know you said attitude was really important earlier but is it something you can teach or is that something you try to go for from the start?

Ryan: you know i think you have to have an underlying skill set for sure.And we've you know we've worked through some - we've been lucky i'll say to start off. So we've been a bit lucky with our hires
like you know i mentioned that we have a lot of friends working here. Just so happens that a lot of the friends are pretty skilled at what they do. But there's been a few of our team members also that started from scratch so i've kind of seen it both ways.You can teach to a point for sure but you need to have a good foundation and a good base I would say. I do think attitude trump's skill set but you've got to have a mix of likes at least 60/40.

Brandon: right

Ryan: and, you know, basically being digitally savvy nowadays is super important and so it's not even so much that you have a skill set in like you know programming or, you know, just being great with customers sales you have to be kind of digitally savvy. So if anything that's kind of the base that i would say that we that we look for. You know, can you handle your own in four or five different applications like Slack and Intercom and email and not get overwhelmed, right? and so that's kind of like the biggest hurdle is just making sure that that base is there. But, you know, we recently hired a developer who's in Poland and he's incredibly talented. And you know it's nice when you quote/unquote get lucky and you get something like that - because we could have done more diligence for sure - it was a recommendation as most of our employee hires have been. Just a recommendation from somebody and so you kind of have to trust the people that are on your team to make those recommendations if you're gonna go that route.

Brandon: Sure

Ryan: And we've been lucky more than once so we've got a really strong backbone on our team and kind of people in each role that really can hold their own weight.

Luis: I know we're kind of dancing around a little bit but when you think of your company and the things that you go through, what truly defines success for you? As the owner of the company - as the CEO - as well as you know what is defining success for a team? What are those kinds of things that really you know make it feel right?

Ryan: sure yeah so we have several key metrics that we watch to determine the company's success and as long as they're going up and we're meeting our goals, you know, that's pretty much the company side. But ultimately success is - is everybody happy? Do people resent coming into work? Are they frustrated? We focus a lot on that. We implemented an unlimited vacation policy last year just because we want to make sure everybody's getting the time off they need and keep the team right. And you know success can definitely be measured in different ways on the company side. You have your key performance indicators - your KPIs - and things like that and we track all of that but ultimately are the people you're helping happy and successful? Right? And when you're able to provide a service like that you know makes your customers happy, then, you know, you sort of get something out of that yourself. And so first off we are definitely focused on like, you know, making customers happy and we're lucky that we've got some good software and usually we keep people pretty happy. So you know I guess the underlying thing i'm saying here is that happiness is kind of the key to success in my eyes. Even on the business side everybody's friends and happy to come into work every day. But you know on the business side, are your customers happy? And if they're not, what can you do to
change that, right? There's a lot of times when a customer's being challenging and you want to, you know, you want to be short or you know you have a - just like yeah you want to be short is a good way to put it - but you really have to go the extra mile and make sure that they're happy. And you know if your customers are happy then ultimately i think you'll be happy as well and find success. So yeah that's a good way to summarize it - you know happiness is success in my eyes.

Brandon: I guess there's those customers who are frustrated, too, those are generally the ones you can
turn around to be the most vocal supporters.

Ryan: You know we've had a lot of good results with that. If somebody leaves a negative review, we jump on it and more often than not we can flip it from a negative review to a positive review because, if they're passionate enough to speak out and are angry for some reason, then chances are they'll engage with you and, you know, let you turn that around. And we've done that more than once. We've had a one-star review come in or something like that and then we immediately reach out, get a hold of them
and usually we can flip them to a five-star review which speaks to that whole thing about keeping your customers happy. And then we feel good obviously when that happens because we know we were able to work through an issue that would have otherwise just driven maybe the customer mad or led to lesser lifetime value for that customer. If they've got something underlying that they're just not speaking out about or they didn't speak out about and it's not addressed then it's not gonna it's not gonna go well long term. So yeah for sure, Brandon.

Luis: You know it's funny Brandon and I were working on some projects together and that's something that i really had to become accustomed to was the idea that when you have any kind of engagement with customers it's great whether it's negative or positive because it's an opportunity. It’s an opportunity you can do something you can bring somebody back into the fold or you can create a long-standing relationship. So on that theme, right, challenges are always arising at the business. What keeps you motivated to keep rising to the challenge and going past it? Is there something that, you know, is there something that you keep as a goal oriented in your head that you're like when it gets hard I focus on this and I push forward? Why don't you give me a little insight on that?

Ryan: Yeah so you know it's hard to say that there's like a specific goal that, you know, really pushes me there, but ultimately to keep things moving you have to stay positive. And so when stuff gets tough, you know, a lot of times i'll take a walk. It's easy to stay in this office and you get you walk in at 8:30 and you look up and it's 5:30, but when something's challenging sometimes you just have to take a walk and change your mindset a little bit, clear the head. When you do that - or when I do that -you know i usually can come back, sit down and be a lot more effective at whatever i was going to do previously. So yeah you know that that five minute walk about that i do from time to time definitely helps keep things moving and clear the head for sure.

Brandon: See i thought you were going to say when things get tough i just think about the seahawks winning.

Ryan: Yeah no i mean that helps too.

Luis: I'm a dolphins fan so i'm kind of stuck, you know, like

Ryan: yeah I feel you we have the Seattle Mariners up here too if that makes you feel any

Luis: we haven't done much and since, like, what - the perfect season in 72 which
is like our claim to fame?

Ryan: Yeah had a couple good prospects in there for quarterback two
Tannehill and all that just didn't work out.

Luis: It’s painful.

Ryan: Ebbs and flows its all cycles. It’ll come back.

Brandon: So yeah so where where are you headed over the next like five to ten years? Like what do you see is the future for PayWhirl and for the other apps you're running? And and how do you think that new technologies are going to affect your industry?

Ryan: Yeah good question so you know the e-commerce industry has grown double digits for i think 15 years now maybe even 20 years, and I don't see it slowing. The market is massive so there's all sorts of niches that you can get into, and we have several apps - we do recurring payments, we have a loyalty app and, as you know, we just acquired an upsell app. So we're focused on e-commerce and i think over the next decade even that that market's gonna continue to grow, there's gonna be more and more merchants that on board into different ecosystems. We work a lot on Shopify and BigCommerce which are, you know, major platforms that help people host their websites but there's new platforms coming up all the time including social platforms - there's some really cool stuff coming out where basically it's formats like this that are live for your store where you have video and there's overlay tools that are coming to help with things like subscriptions and closing sales in in live video and in you know Zoom and other platforms. So we're always kind of looking around to see what platforms would be good to integrate with. That's one of the things we've done pretty well at PayWhirl over the years. We've always selected really great partners. You know larger ecosystems that have customers that need or businesses that need something specifically right and I don't think that that's gonna change anytime soon. There are some big things coming for the payment space - like cryptocurrencies had a year. And we've been watching that closely since you know 2017 / 2016. i think even you know prior to that we actually technically had support for bitcoin like a long time ago through Stripe and so we know that that's coming but i don't think the tools are there yet. As they say the pioneers get slaughtered and the settlers get the gold so to speak so we don't want to be too early to market there but we're keeping an eye on it because I think that will change the landscape of transaction fees. You know as some of this layer two crypto stuff comes down the line where you know you can get truly free processing or fees we're gonna have to look hard at that and how we how we stay relevant because a lot of our billing models are based on a percentage of the transaction and so like we have a free plan you can sign up for free but because of that we take a percentage of the transaction when you're on the free plan. And so with you know with crypto coming we're gonna have to look closely at that and see how we can adapt. And i think that the tools are progressing so i don't you know i don't anticipate it as some monental thing that will change the landscape of our business but if we're not careful, you know, we definitely could lose market share to new tools that come out. So like as I said we're always looking for platforms that we can build on and expand from and I think as long as we do that we'll be, you know, set up for success long term.

Brandon: Yeah i guess, you know, we've seen over the past year a lot changed with COVID obviously and i know that the Shopify ecosystem has seen a great deal of change as well with, you know, more businesses moving online, you know, you’ve seen a huge suite of apps come out over the past year for curbside pickup and things like that. How do you see the changes that have been implemented due to the pandemic, you know, how do you see those going into the future? Do you think any of them will
be sticky and we'll, you know, that we'll be talking about, you know, curbside pickup here in five years or do you think a lot of this, once people go back to business as usual, will just sort of like roll back to how it was two years ago?

Ryan: yeah i think it's here to stay. You know, I had dinner with a close friend recently and he was like “You know, there's one thing I'm not giving up after COVID and it's Instacart.”

Brandon: right

Ryan: it's just so much better than going to the grocery store and going down every aisle eight times and you know all of that, you know, pain that you do to go to the grocery store which is funny because even a year ago it seemed like a total luxury, a novelty type product and we used it a little bit prior but now we rely on it. And i think, you know, because of the the pandemic a lot of people have been forced into using these tools but kind of like in a good way, you know, you - force maybe isn't the right word

Brandon: but now they're used to it

Ryan: yeah so everybody's kind of you know used to it now and realizing that this technology is here and it can be utilized going forward. You know i think google just extended - they were talking about forcing people to go back to work for 2022 but i think that they - at least a friend of mine who works for them said - that they are allowing them to choose now because the tools are in place everybody's had to adopt them. They're now in place and so companies are invested in these tools and, you know, even on the consumer side you know i'm invested in Instacart now. I love it. I don't have to go to the grocery store it's here within two hours and I don't think that these tools are gonna get worse right they're just gonna keep getting better so i think a lot of these changes that we've experienced are gonna be here for the long term. And yeah and we're lucky because we kind of you know we were ahead of the curve and so we saw a huge influx last year and even through this year you know we had eight out of 12 months last year were all-time highs for us which you know usually it's about with our growth it's four to six months you know we do all-time highs but it was like every single month and with the launch of our new Shopify app that leverages a bunch of internal technology that they have to keep checkouts more native, and things like that you know our our growth has been really explosive in the last year and i just don't, you know, i don't see it - i don't see it wanting. I think that it'll continue to pump. You know people may back off - you know, when everybody's vaccinated and you can go out again and everything's open i think there might be a period where people sort of you know their pent up and so they'll, you know, they'll go out and experience that but i don't foresee a lot of businesses just cutting off the digital tools they've implemented - at least the ones that are helpful, that are truly helpful that are adding value to their business which, you know, hopefully we're in that category.

Brandon: what a world to live in - you know - oh we're gonna go out and have an exciting experience of buying our own mayonnaise at the grocery store

Ryan: yeah going to a restaurant. i mean it's - it's bizarre. We're slowly opening up here which is nice and i think Georgia's a bit ahead of us - how it in Vermont, Brandon?

Brandon: oh i don't think vermont's ever going to open up. Everything is really really locked down they just they just opened up people who have been fully vaccinated and have both doses can now come to the state without quarantining for two weeks

Luis: since when?

Brandon: Tuesday

Luis: Ah. Georgia is weird. Georgia is like it's been - we've been open for business

Brandon: They never stopped

Luis: not really i mean like i mean i mean obviously you know at the beginning of COVID you know there was this definitely curve, but then after a while i think people just became acclimated to the situation or some just kind of just they gave threw up their hands they're like forget it i'm just doing what i'm gonna do and you know people are very very free about that kind of stuff here. So it's weird. What's weird to me
though is that how you know COVID - i mean obviously you know the negative aspect of it is of course you know the virus itself and the effects on the human body and people, you know, having deaths and all that but it's been such a great accelerator for you know ecommerce and online businesses and all these different platforms. It's amazing how it's like before COVID you know you were, when you're strategizing you're looking more like oh the next five years the next 10 years maybe. This thing came in and it was like a matter of months and people just had to transition so fast that you know it just it's you know exactly what you're saying it's just like the influx of clients and people and consumers it's just

Ryan: yeah excuse me absolutely yeah i agree

Luis: all right well so you know you know we're almost at the end i guess so so really i guess the last thing that we would like to ask is you know give us you know three things that you want to you know tell us about yourself it doesn't have to be business related it can be anything just three items of whatever go for it - go

Ryan: You know, i can give you my favorite color

Luis: okay

Ryan: but that's not that important you know

Luis: i mean it might be

Brandon: well now i want to know what it is

Ryan: You’re gonna have to wonder. You know I tend to like blues and greens. Those are my favorites. You know a little orange for flash sometimes. You can probably tell by the color scheme of our website actually yeah which colors are my favorite. But you know one thing I'll say just in closing is that you know it has been a trying time for a lot of people. I think we're near the end of it and you know as much as we need to stay you know focused on our businesses and whatnot it's also important to take
a bit of a digital detox from time to time. And something i've been trying to implement in the evenings a little bit is really you know shutting off the device and disconnecting. Especially now because we're all working from home so you know that's something that i'm trying to do personally and i think it's awesome when you can just disconnect a little bit. So you know as we get over the hump here with the COVID thing, I'd recommend that people you know try that. You know they even have these lock boxes you can put your phones in if you have if you have issues and can't and can't put it down where you lock your phone in a box and unless two people provide keys you can't get into it

Brandon: yeah i was gonna say that's just you lock it in the box and then cross your fingers you don't have an emergency

Ryan: yeah that's actually what i need is a lock box otherwise i'm pretty glued to it but you know i'd say go hawks too love - the seahawks. Excited about our new hockey team here in seattle. We've got the Seattle Kraken starting later this year

Luis: that's right

Ryan: and yeah you know be well. And yeah that's pretty much that's all I’ve got

Brandon: awesome awesome. Well thanks again, Ryan, for joining us today. How can people find out more about PayWhirl? You want to drop some urls out there for some folks?

Ryan: yeah it's app.paywhirl.com for PayWhirl, we also have, you know, Glow Loyalty which is glowloyalty.com and Upsell Wizard which is upsellwizard.com. So feel free to take a look at any of those they're also listed in the Shopify app store, the BigCommerce app store and other places so we'd love to help if you have any needs for recurring payments or any of those other things - loyalty or upselling your customers.

Brandon: awesome man. Awesome. Well we appreciate all our listeners for tuning in. You can find all of our episodes at sendlio.com or wherever you get your podcasts and we'll see you next time.

Ryan: thanks guys

Luis: thank you


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