113: How Tech Genius Went From Code to Millions with Calvin Correli

Calvin Correli is a serial entrepreneur, speaker, and the founder and CEO of Simplero, a CRM shopping cart marketing automation tool for coaches, consultants, and creators.

The company does $4M/year with 35 employees and has served thousands of customers worldwide.

Up until recently, Calvin wasn’t really aiming for company growth. Instead, he put his energy into the two areas that are most important to him: building a great product and outstanding customer service.

Today, you’ll learn about the project management tools and tactics Calvin uses to improve operational visibility, his vision for scaling his company to $100M, and the specific elements behind creating a client experience that leads to a continuous flow of referrals.

Inspiring Quotes

• “When you have people that actually care about your customers, actually care about giving good service, everything is easier.” – Calvin Correli

• “At the end of the day, yeah, we’re doing business, but it’s a game, right? What matters is relationships, starting with the relationship to ourselves.” – Calvin Correli

• “Accomplishment is not doing things. It’s enabling others to accomplish.” – Calvin Correli

• “I derive so much joy from being of service to other people where it’s not transactional, but I just know that I’m making a positive difference in another person’s life.” – Calvin Correli

• “Success to me is a feeling that I get from having an optimal daily experience that’s sustainable.” – Calvin Correli

• How Calvin grew to $4M/year in revenue without a marketing plan
• Calvin’s process for managing and tracking his team’s progress to ensure projects get done.
• How to cultivate a culture where people actually give a damn.
• What criteria can founders put in place for finding the right employees?
• The idea of “abstractions” and how entrepreneurs can use them to drill down into what customers really want.
• The tie between spirituality and entrepreneurship.
• How an emphasis on interactive customer service can lead to innovations in product development.
• The difference between product managers and project managers — and why the nuances matter.
• How entrepreneurs can use rest to boost productivity.
• Balancing a desire to move forward on a creative project vs. waiting until you have a defined path.
• Leveraging referrals to create a customer base that compounds your success.
• The reason why most recurring billing products suck.

Brad Weimert: Calvin Correli, thanks for hanging out, man.

Calvin Correli: Thanks for having me.

Brad Weimert: Absolutely. It’s good to see you. You are in town for Baby Bathwater.

Calvin Correli: Yes, that’s right.

Brad Weimert: Interesting group. Interesting group of people. Good events. Do you have fun?

Calvin Correli: I did. Yeah, I had fun. Actually, this time I’m getting better and better in doing these events. So, this time, I didn’t feel obligated to actually be part of that group or the events the whole time. So, I just pull back and get some work done and do some, you know, have some meetings, do some other stuff, and then just reenter the group when I want to.

Brad Weimert: Well, one of the things that I find interesting about that particular group, so there are all these for framework, there are all these sort of CEO entrepreneur groups out there and they get dubbed mastermind groups. It’s a terrible label for them really because it’s like they’re just events, right, where you get to talk to people that are hopefully established entrepreneurs and they all have different filters. And the filter for Baby Bathwater is really just the two founders and whether they think that you’re a jackass or not or they think you’re really interesting, right? So, one of the founders, Lovitch, is an outspoken, irreverent human who I love. And one of the things he said very early at an event I went to, this is years ago, he got up day one and said, “Hey, listen, if you want to come in and listen to somebody talk, sit down and f*cking listen to him talk.” He’s like, “If you don’t want to be here, get the f*ck out of the room. Somebody else would like the seat.” He was like, “If you want to go out and drink at the bar while everybody’s doing this and just talk and socialize, that’s awesome. The event can be that for you. If you want to be outside working, do that. The event can be that for you. But if you want to be in the room, be present, be in the room.” And I just thought that permission to do exactly what you just said is one of the cool things about the ethos of that group.

Calvin Correli: Yeah. I find it very open. The culture is definitely a lot of alcohol and other substances like that party vibe. And people stay up to like 4 a.m. or 5 a.m. And then there are some others who just go to bed like 10, 11, 12, and stay sober and have great conversations with people.

Brad Weimert: Yeah. That’s awesome. Well, I also like that the permission is there to do that, if you want.

Calvin Correli: Exactly. Yeah. There’s no shaming for doing that.

Brad Weimert: Yes. Well, depending on who you’re talking to. Cool. So, give me some backdrop about, you know, we’ve been talking quite often as of late about Simplero, which is your current venture and what you’re doing. And I want to dive into that but before we get there, why don’t you give me kind of background on who you are, how you got there.

Calvin Correli: Yeah. So, I was born into software. My parents actually got into computers back in the 70s. There are literally a handful of computers in the entire country of Denmark where I’m from. So, really born into that world. My mom started the software company in 1980 and grew that to 50 people.

Brad Weimert: Wow.

Calvin Correli: Yeah. So, female CEO of a software company in 1980 in Denmark. Yeah. So, it was like completely born into the world of software. As a kid, whenever I was like given crayons to play with, I would sketch out user interfaces and software stuff. Like, that’s how nerdy I was. Yeah. And so, I got really good at the mental stuff but I didn’t get so good at the emotional stuff or the social stuff. Like, I got crazy good at computers because I was terrified of human beings. Bullied in school. People would say stuff and then I would have feelings and I’d feel awful and be like, “No, like, go away.” And so, computers, on the other hand, I could tell them what to do, and if they didn’t do what I wanted them to do is always because I gave them wrong instructions. I could find out what they were and fix it. I was in control. So, it led to later in my life, like period 2003 to 2008 was like a very deep, introspective period for me of learning to feel again, learning to open up my body, my heart, everything, and therapy, coaching, spiritual teacher, all of that.

And that eventually led to a moment in 2008 whereas like, “Okay. Crap. What is my purpose in life? What am I here to do?” And I sat down, wrote down some questions that I found in different books, and asked myself those questions. And then it just leapt out at me. I’m like, I’m here to integrate spirituality and entrepreneurship. And that’s it. And that’s been true for me ever since. I’m like, “Other entrepreneurs need to know this,” like they need to know their purpose and be aligned with their purpose in life. They need to know, learn how to feel and process emotions, right? Like, the emotional roller coaster is like a cliche because we don’t know how to deal with feelings. We just let them ride us, take us places, meaning knowing how to deal with our minds and the mental like thoughts and beliefs and ultimately learning to be in the present moment and open our hearts. Because at the end of the day, yeah, we’re doing business, but it’s a game, right? What matters is relationships, starting with the relationship to ourselves. Like, damn it, I need to teach this to other entrepreneurs.

I discovered Jeff Walker and Product Launch Formula and online courses. I’m like, “This is great. I don’t have to be in front of a billion people. I can keep staying behind my computer and do this.” And so, I started doing online courses, 2008, and quickly was like, “Hey, I think I can do better on the software.” And that’s how Simplero was born.

Brad Weimert: Awesome. Yeah. I mean, I grew up in pretty hardcore sales and very early found Tony Robbins. And Tony Robbins to me was the starting point of in, you know, in the entrepreneurial space, most people have respect for that, for him as a human. I think globally you get a mixture of respect and sort of disdain for the guru nature and people think that he’s a snake oil salesman or whatever. Like, you see the whole spectrum of people.

Calvin Correli: Totally.

Brad Weimert: And my commentary, generally, with that is, look, anybody that’s been around for 40 f*cking years and he’s making a lot of money, clearly, some people think it’s a very good thing. So, that was the starting point for me having realization and in sales, it’s very easy but having a realization of me controlling my own emotions and mind and focusing on that is the first thing you have to get control over in order to accomplish the goals that you want. And as you go through life, each new chapter introduces potentially a new way of thinking, right? And so, certainly, when you get into business, you look at the different levels of business that you go through. What you have to do operationally changes, right? And then the emotions that you connect to a given outcome have to change. So, one of my current struggles is that I am an executor, so doing things makes me feel accomplished and I’m consistently working on changing that association to accomplishment is not doing things, it’s enabling others to accomplish. And there’s a gap there that has to be jumped and it took getting to a certain level to do it.

Calvin Correli: Totally. Yeah. And I have a mentor or used to have a mentor. She used to say manifestation comes from rest. So, even taking that like actually when I’m like, especially someone like you and I are so driven, always like doing stuff, doing stuff, doing stuff but then the breakthroughs happen when we’re not doing stuff and we’re actually at rest.

Brad Weimert: Yeah, it’s interesting. Years ago, I had this thought that the most productive thing that I could do was nothing.

Calvin Correli: Yeah.

Brad Weimert: And it’s the same sentiment, right?

Calvin Correli: Exactly.

Brad Weimert: So, if I can clear space, then sometimes that’s where I get clarity. Okay. So, tell me about Simplero and the journey with Simplero.

Calvin Correli: Yeah. So, I set out to build just the best product I possibly could for that type of information coaching, consulting business, right? A business that doesn’t sell widgets, but sells some kind of digital service information, typically. It’s a very different thing from selling handbags or widgets. It’s a different way to market it, sell it, all of that stuff is different. So, I was like, “Hey, let me build, do that.” And I got super deep into the Internet marketing world in 2009-2010, and then I had a bad taste in my mouth because it seemed like a lot of people were, you know, they would basically skirt the truth a little bit to make a sale, right? I was just saying. It was like sometimes it felt like you got in a room and it was like remember like from stage, they would say like, “Hey, you notice that like thing that we did that really manipulated you to buy the thing to get here and it felt kind of sh*tty?” He’s like, “Yeah, we’re going to teach you how to do that with your clients.” So, it’s good to pitch, right? I’m like, “Oh, I don’t like that.”

So, actually, I withdrew from that whole world for eight, nine years and just focused on product and customer service. Like, those are the two things that I love the most is just build an incredible product, do incredible customer service. Now, like if I were to do it over, I wouldn’t have pulled out that hard. It was getting out of this super mature reaction on my part. At that time, I would rather have stayed in and just be like, “Hey, you can totally be of integrity in that world,” right?

Brad Weimert: Yeah.

Calvin Correli: Just because other people don’t have it, doesn’t mean that you can’t. But it got me to this point of like actually over, dude, 13 years we’ve been just building the best damn product and offered the incredible product servers and just neglected to tell anybody about it pretty much. I mean, we’ve gotten to this place purely through word of mouth.

Brad Weimert: Well, so two things. One, I think there’s a really important lesson there, which is you can take the good things and leave the bad things.

Calvin Correli: 1,000% right.

Brad Weimert: And keep moving. And I have the same knee-jerk reaction as when I – but for me, it’s with people. When I see somebody that I respect and then they do something that is out of alignment, historically, I would just sort of discard them and be like, “Well, clearly they’re full of sh*t.”

Calvin Correli: Right.

Brad Weimert: And as I’ve gotten older and more mature and actually business has facilitated this, I have adopted a viewpoint of, okay, well, they maybe don’t listen to them about this thing but they’re still great lessons and they’re still a great person over here.

Calvin Correli: Totally. Right, exactly. You don’t have to take everything from anybody, right? Ever. Yeah.

Brad Weimert: Yeah. Look for the one thing.

Calvin Correli: Take what you can use.

Brad Weimert: Totally. So, number two is what Simplero is. So, in simplest form, you can add context to this. This is my understanding. And then we’ll talk about marketing because my understanding is going to be a product of the marketing or lack thereof. But Simplero, as far as I know, is sort of a CRM shopping cart marketing automation tool for people that are coaches, consultants, and selling information.

Calvin Correli: I think that’s pretty perfect.

Brad Weimert: Nice.

Calvin Correli: I love it. Yeah. The way I’ve sort of explained most recently is in terms of what it is, right, is CRM plus payments, plus courses or content and community in one box.

Brad Weimert: Great. Love it. Which is why we’ve been talking a lot more lately because we have a huge chunk of people that fit squarely into that wheelhouse, right, that are selling information, doing courses, etcetera, at Easy Pay Direct. So, where…

Calvin Correli: And on that note, so, this is where, again, because I’m a product guy like I didn’t realize that I had… It’s kind of a pattern of my life of like I’ll go into a cave and then I’ll work hard and stuff, and then I’ll come up and look around and be like, “Where is everybody at?” like gotten from feeling inferior to being so far ahead of everybody else. I’ve done that over and over again and here with payments, it turns out that we’ve built apparently like probably the most powerful payments engine that exists on the market. And I didn’t know that that’s what we did. I just built it based on customer feedback and just me being an engineer and a product person and be like, okay, what does it need to look at to be powerful?

Brad Weimert: Yeah. And for clarity, in this case, we’re talking about sort of what makes it powerful is the flexibility in recurring payments.

Calvin Correli: Or installment payments.

Brad Weimert: Right. Yeah. So, the ability to break apart exactly how you run the transactions when, why, etcetera. And I’ll outline some of that. So, specifically on the payment front, one of the challenges that anybody with a high ticket product or a subscription, I think these are kind of the two boxes that this is most relevant for, they’re limited. Actually, trials are another one like, “Hey, test this, and then we’re going to change the pattern of payment later. Like, here’s a dollar trial and then ten days later or 30 days later, we’re going to bill you whatever, whatever.” Those rules are very rigid in almost all platforms. They’ll say, “Yeah, we do recurring payments,” and you can either bill people monthly or annually and like those are your options, right? Or you can start it on this date and you can skip a payment. But they’re really structured and limited.

And one of the things that one of our clients brought to our attention was inside of Simplero you have the ability to like you can set a schedule for a monthly payment and then you can go in and say, “Yeah, but this third payment, we want to use a different card and we want to do it a different day in the month.” And you can just modify and you see the whole payment schedule in front of you right there. So, it is definitely a cool user experience for them and cool you on.

Calvin Correli: Yeah. And I didn’t realize this was a problem. So, yeah, you can do trial however long you want it like four days or like 18 days or like it doesn’t matter. Or recurring billing in different like it’s 97 a month for the first couple months and then it drops to whatever or increases or you can do like any sequence of payments in a payment plan. You can find all that stuff upfront. You can do a custom plan for a given client and these sales rep can easily do that themselves on the fly. And then on the accounts receivable, just like you said, change all the payments for a given client if you need to and we’ll still keep track all of it.

Brad Weimert: Yeah. So, this is a good segue way because the reason that almost all recurring billing products are sh*tty is because, or limited, I’ll say, is because most software developers and we have – so we get software companies at least once a week that come, that are looking for Easy Pay Direct to do the payments for their platforms. So, we had these conversations over and over and over and over about integrating payments into a platform. And so, I’m speaking from a lot of experience with this. Most software developers take the laziest possible approach to do to integrate payments. And so, what I mean by that is they’ll take and that’s actually why Stripe has become so popular because they look at Stripe’s SDK, which is the software development kit, which for those that don’t know, is basically a bunch of snippets of code that you would put all over your product that would leverage Stripe’s recurring billing, and Stripe’s ruleset, and then you’re limited to whatever Stripe’s ruleset is. And the same thing is true with most payment providers because they’re not out to have a super robust, flexible, different option. They just want to facilitate the payment.

So, when people build these integrations, they’re either doing that and leveraging like Easy Pay Direct’s recurring payments, which are functional but not nearly as robust, right? Or Stripe, same thing, functional but not super robust. Or they can build out the whole thing themselves and then every time a payment needs to fire, they just request one specific payment. So, they’re not leaning on our recurring engine. They’re building their own. But it takes a tremendous amount of additional time to do that so developers don’t do it. So, it’s really uncommon to see that. But I walk through that as a segue because, at the core, you are a product person, as you mentioned. So, I want to talk about how you build a product and how you structure it because I think we’ve gotten into an era where so many businesses are dependent on technology, and more and more entrepreneurs are looking at, “Where is the technical element that I can integrate?” And so, you’re ending up with more and more non-technical founders that are trying to build software.

And so, building software is a b*tch and it behooves you to have some structure and idea of what the f*ck you’re doing. So, how do you approach like, what does your team look like right now and how do you approach it? And I’ve got a series of granular questions that I’m curious about.

Calvin Correli: Totally. It is hard. It is hard. All right. So, we have six engineers right now. We have two designers, one QA person, and then I’m the product owner, the product visionary, the product manager. Like, we don’t have any product management right now. One of the challenges for me has been that. Like, for me, it always came natural because I’ve been doing it my whole life and it took me a while to realize it doesn’t come natural to other people to do what I do. So, I was like pretty much the only person writing code for a very long time until I found this one guy who is a genius. And he took over and his brain kind of worked like mine so he did really good work and he basically took it over. Then he left to start his own company. I was back to just me being the only programmer. Then when I finally solved that and figured out how to hire good programmers, I didn’t give them the direction and the leadership that they needed because I didn’t realize that programmers don’t think the way that I do.

Brad Weimert: Interesting.

Calvin Correli: Because it’s like I know the business, right? I’ve been in the information marketing since 2008. I know that very, very well. I’ve been doing software my entire life. I’ve been head of user interface. I love user experience and user interface. I’ve been studying that for years and years as well. And I’m the engineer, right? So, I put all of that together in one head. But you get an engineer, they don’t know user interface, they don’t know the business, they don’t know the business, the information marketing world. And then I had a product manager for a while who I made the mistake of making head of product. He was a great product manager but then I elevated him because I looked at an org chart and like, “Hey, we need a head of product.” And all of a sudden, he was making decisions that he wasn’t qualified to make because he doesn’t understand the business use case the way that I do and/or the engineering.

So, right now it’s me doing that and I’m very, very good at it so I can do it very, very effectively with minimum time but what it is, is it’s listening, always listening to what people say they want or need, and then figuring out the right abstraction. And for us, we always think about like making it simpler and it’s really taking the time back to what we started about manifestation comes from rest or like not doing stuff. Wait until you know the right abstraction before you start implementing.

Brad Weimert: Let me break apart this concept of abstraction and see if I understand it so other people can. When somebody kind of ties to the notion of Henry Ford’s famous quote, which is to the effect of if I ask people what they wanted, they would have said, “A faster horse,” when building a car. So, the car in that case is the abstraction of what they’re after. And what they’re after is what they tell you is not necessarily literally what they want but somewhere built into that statement is conceptually the outcome that they’re after. And in software and how you phrased it, you’re using the term abstraction. Is that fair?

Calvin Correli: Yes.

Brad Weimert: Okay, cool. So, you’re thinking like somebody says, “Hey, you know, this checkout page should do this.” And your thought is, “Let me take some time and figure out what they’re actually trying to convey to me and what problem I can actually solve.”

Calvin Correli: Right. Exactly. Yeah. They’ll tell you like, “I want a checkbox here or I want this feature or whatever,” and then you have to ask like, “Well, okay, what’s the context? What are you actually trying to solve here? What is the problem?” and really to drill into that. And then you give me. “Okay, good. Now, I understand that. What is a more general solution that I can come up with that’s simple that solves this problem and other related problems and doesn’t screw us in the future?” Because it’s very, very easy to build a ton of stuff and now you have to maintain it. But now you have to like, “Well, oh, now if we add this one, it screws us over here,” and it’s incredibly easy to do. So, like now I don’t let anyone tell my engineers what to do on anything unless it passes through me unless it’s like a quick, obvious bug. That’s fine. Go fix that. But anything else, like I need to make sure that we get the right solution for the problem. And then I coach my team to be able to do that. I’m going to hire a product manager obviously.

Brad Weimert: Yeah. I want to talk about that structure and framework because I think that it’s something that when you dive into software, people don’t have any grip on at all of how the team is supposed to be structured. But this idea of adding one thing on top of another on top of another, you end up with sort of a Frankenstein structure. And the term that I am becoming more and more familiar with is technical debt. So, once you put these things in place, you don’t have any choice but to maintain them or get rid of them. So, yeah, it’s…

Calvin Correli: Or refactor and simplify. But now if you have customers that are depending on those features working that way, that becomes a whole process of like, “Okay. Now, we can’t just change it. Maybe we need to work with them to migrate off of that.” And there’s a lot of work involved in that. And that work pays off like I pay that price so that we can simplify the code going forward. All right. But it is a price to pay.

Brad Weimert: Okay. So, let’s talk about the structure. So, you started as, you mentioned some titles that if you’re not in, if you are a smaller entrepreneur and you’re certainly just starting out or multi-seven or even into multi-eight, I guess it’s more of a product of how deep you are into software development, but people don’t know product managers.

Calvin Correli: Right.

Brad Weimert: And the difference between a product manager or a project manager.

Calvin Correli: I didn’t either, right? So, a product manager is essentially the person who figures out what needs to be built. So, the product manager works with designers and customers, etcetera, to find out what needs to be built. And also, engineers, right, because like how complicated something is to build is an important factor of our decision of what to build but that essentially is what they do product, figures out what to build, and engineering figures out how to build it. So, that’s the distinction. And again, for me, I was always the engineer who also figured out what needed to be built and I didn’t realize that that was a whole separate career path for people. And then the other piece was that like head of product thing, and I think that’s more general. If you have someone on your marketing team or sales team who’s a great individual contributor, now you make them head of that department because like me, I was looking at an org chart and be like, “There’s no one there.” So, that’s not usually a good decision, right?

Brad Weimert: Right. Yeah. So, in our world, we have a five-person internal development team and we largely are building tech for our onboardings or internal staff. Most of our technical effort goes towards our internal staff and analyzing data. We’re dealing with a tremendous number of transactions like there’s just a lot happening in there as you are with payments, right, in the payment engine. You’re integrating for it. Anyway, different conversation.

Calvin Correli: Yeah. I mean, we just have our system say who needs to be charged, what, when until Easy Pay Direct or some other payment processor, yeah, to like now go dang the card.

Brad Weimert: Yes. You know, use transaction. So, anyway, we’ve got this development team and we have two core things that have become very relevant. One is the idea of the product manager and who’s actually owning what direction we’re going with the product and what the product should look like, what we’re trying to create and when and where, and how we do it. And then they’re working with the engineers on a routine basis, the software developers on a routine basis, to iron out the best way to do that and, say, “Well, the way that it’s being built currently, does it align with what we’re actually trying to accomplish?” And developers need that because most of them are tremendously literal. And if you say do this, they will literally do that, missing the whole point of the thing. But what we have lacked and what we found over time that was so necessary was a project manager. And that’s somebody that just keeps things on course and says, “Hey, are we on track with this? Did you do this? Did you add notes? Did you comment things out? Is this being managed the right way?” Do you have a project manager? Are you the project manager? How do you make sure that things get done? Like what methodology do you use to create the software?

Calvin Correli: I don’t have an official project manager. I have some people on my team. My QA person, I lean on her to do some project management. My number two, my chief of staff, does some project management for me there. It’s a good idea but what I do like I might need to hire a project manager actually. It’s not a bad idea. But what I do is I’m really good at creating systems and automation. So, what I have, we use Linear to manage the workload in on our product team or engineering team which is so much better than Jira. I don’t know if you guys use Jira.

Brad Weimert: Oh, really? We are.

Calvin Correli: Jira is terrible. Everybody hates it. There are websites dedicated to how terrible Jira is. I was so blessed that I found Linear.

Brad Weimert: Interesting.

Calvin Correli: It’s so much better. Yeah. It’s actually a joy to use. So, we use that tool. It’s similar in a way like it’s just a to-do management system specifically for engineering and it integrates with GitHub and things like that, which makes it really cool. But then I have my engineers do a daily project update in Slack. So, we have engineers all over the world, so different time zones. So, we don’t do a daily stand-up meeting but I have all my engineers, in the beginning, they do a stand-up check-in, and then at the end of the day, check out. So, here’s what I plan on doing today. Here’s what I’m blocked on. And then at the end of the day, here’s what I got done. Here’s what I plan on doing tomorrow and here’s what I’m blocked on. So, they post that in Slack every day and it gives me a tremendous, you know, at a quick glance, I can just see what’s going on and I can drill, drill down, and stuff.

Brad Weimert: Is that in one channel?

Calvin Correli: In one channel. Stand-up engineering channel.

Brad Weimert: Love it.

Calvin Correli: Yeah. And I do that for my marketing team and my sales team as well. Same format.

Brad Weimert: That’s great.

Calvin Correli: And then what I’ve started doing is a project status update precisely for that reason to keep my engineers focused on, “Hey, we’re not just doing tasks. We’re actually accomplishing projects.” So, I have them do, at the end of the day, for each project that they individually own, whether they’re the ones doing the actual work or not, there is a project owner, and they post here’s what was done today, if anything. Even if nothing is done, I want to see a bunch of report.

Brad Weimert: Yes.

Calvin Correli: Here’s what was done today. Here’s the next step that’s going to be done like the very next thing, tomorrow when I pick it up or when someone needs to see what they’re doing. Course of action is like at a high level. What are all the things that need to happen to completion? Most days they can just copy-paste from yesterday’s report, right, because it doesn’t change but I still want to see that report pushed to me in Slack. So, course of action to full completion and their current estimated completion date, given workload, vacation, everything else, like a specific date that they think this is going to be done. And then again, anything that’s blocking for this project. And that lets me at a glance see, “Oh, like that date is not going to fly or that’s not realistic given the course of action or other things that I know,” and then I can course correct.

Brad Weimert: I love that. So, I want to ask you about kind of overarching planning for this because you just went into it. But I also want to highlight, you hit on all these things, when I think about project management, we live inside of Asana, which I have mixed feelings about but is functional enough. And honestly, the pain of moving is the thing keeping us there. But I think about the purpose of project management tools for me is describe definitively what it is we’re trying to accomplish, have visibility from all parties involved, and have accountability. And there is one owner and one date associated, and that owner is responsible for that date, whether the dependent tasks are theirs or not. And we do not ever change the ownership of a given thing unless it’s being definitively changed. So, you don’t hand off a project or a task. You create another one that’s a dependency because that prevents people from throwing the monkey on somebody else’s back. There is not a situation in our world where it’s acceptable to say, “Oh, well, I’m waiting on blah, blah, blah. That’s why it’s past due.” No, no, this is your date, your deadline.

And inside of the construct of project management, that’s it. One person, one date. Everything else, that’s full accountability. I love the check-ins on Slack or whatever mechanism you have, but that visibility, even when there’s no progress, is so important because that visibility element of project management, if you don’t look at it, it’s not valuable. And so, if you force people to give a check-in and say, “Yeah, we didn’t do anything on this today. We’re focused on XYZ,” fantastic, right? That’s great.

Calvin Correli: I know.

Brad Weimert: But we don’t want to lose visibility of it. Yeah, that’s super cool, man.

Calvin Correli: And for me, most of these projects, like Linear and Asana, allows you to set a weekly cadence where you get project updates to you. I want a daily. Like, for me, it’s just not…

Brad Weimert: I love that.

Calvin Correli: Yeah. A week is like too long.

Brad Weimert: Yeah, totally.

Calvin Correli: To not know that we’re off track or something’s going on.

Brad Weimert: Also, if a week passes and there’s an oversight and somebody doesn’t give the update that week on, “Oh, nothing happened here,” then that can turn into two, three, four weeks because it just falls off the radar. If it’s every day, it’s easier for people to maintain that top-of-mind mentality for something. Yeah. And we use Asana for actual project management, but we use Jira for all engineering-related projects.

Calvin Correli: Until?

Brad Weimert: Until now. Until maybe Linear, which by the way, when our CTO hears this, he, unlike me, is immediately checking out all new things. So, he’s always digging into anything new. And it’s a distraction totally at times but it’s also the way that you uncover huge competitive advantages. It’s like, “Oh sh*t, this new thing came out that solves all these things we’ve been struggling with.” It warrants time, right?

Calvin Correli: Yeah. One thing I want to add is the creative process that I think a lot of people overlook. When it comes to product software engineering, it’s a very creative endeavor on every level, both in terms of a product, what do we build, and engineering, how do we actually implement it. Both are very creative endeavors. So, it’s important to when you project manage it, you can’t just push, push, push because then people are just going to do whatever they happen the best idea was at that moment. So, being willing to be like, “Hey, we really want to get this done. I just haven’t figured out what the right way is yet, so I’m not going to move on it,” I’m going to let it steep. I’m going to let it sit. Yeah, I would love to be able to complete this right now, but I’m not going to complete something where I don’t have that feeling in my gut like that clarity that this is the right way to do it.

Brad Weimert: I love that. Yeah. I mean, look, there are a lot of directions we could go with that. But in general, how do you approach that from a management perspective? So, let’s say you have this project that you’re trying to pursue. You’ve got some clarity and outcome. And as you start to go down the path, you’ve got a list of independent tasks to accomplish that end goal. Does an engineer just not work on the thing while they’re thinking about it? Does the deadline move? Is that part of the daily update in Slack? How do you interact with that relative to creating the space to have flexibility to change?

Calvin Correli: Yeah. So, that particular thing is mostly where I’m involved. That’s my role is to figure that out because they don’t really have the engineers that don’t have the… There might be something that’s purely engineering related but most of when it gets to engineering, it’s pretty clear what needs to happen or they’ll start down some path and I’m like, “No, this is not the right way to go.” Like, something about this feels off. Like, let’s explore some alternatives and I’ll give them some ideas or have them come up with some ideas, or I’ll just be like, “Hmm,” go in and pull up the code editor and try some stuff out. I literally did that yesterday who like, “You coming up with solutions?” I was like, “No, too complicated. There has to be a better way.” So, it mostly happens at that level that involves me.

Brad Weimert: Let’s back out to kind of overarching goal setting, planning, longer timeframes for projects.

Calvin Correli: I want to add to this is like, again, I’ve been so focused on my own product and customer service in my own business, like I recently started opening up and looking out at what other products exist. And I’m like it dawned on me, I don’t know if this resonates for other people but I’m like, “Holy crap. Like, I’m really world-class when it comes to creating software.” And I didn’t know. I had no idea. So, it’s kind of exciting to experience that.

Brad Weimert: Well, we definitely have gotten really good feedback from a few noteworthy clients that use the platform that are raving fans. And it is hard to create raving fans for any software but specifically, a software that has the complexity necessary to run a business. So, I can say that about your product for sure. So, how do you create that is the question, right? So, we talked about sort of granular task management, the team that you have in place for it, backing out a little bit saying, hey, this is a particular project we’re trying to accomplish, which might be building a feature into the software. But how far out do you plan and do you run on an Agile methodology? Like, what’s the framework for the development cycles? What does that look like?

Calvin Correli: So, I have sort of the master vision in my head of what the product wants to become, which is not like necessarily super detailed but it’s more directional. And I communicate that with people but I don’t expect them to hold that vision to that level that I do but it’s kind of always evolving in my head. So, that’s the long-term high-level version. And then when it comes to the actual work that we’re doing, I’ve mapped out the next, let’s say, 2025 projects in Linear and then we’re addressing like we’re working on probably ten of them in parallel because some of them are just like, “Okay. Get it done,” and the others still needs some of that creative time of like figuring out what it is, becoming clear. Then we’re not using any formal Agile frameworks or methods.

Brad Weimert: Interesting.

Calvin Correli: Yeah. I find that they’re like it’s just actually being agile, right? And staying close to the team and the people and the code and it’s just, okay, day-to-day. Like, you know what you’re working on, you know what you’re not working on, and then we see how it progresses, and do we need to make some adjustments? All right. You know, put that on hold. Go over there. Help that guy. Let’s get that one across the finish line.

Brad Weimert: Well, let me ask about that because if you have sh*tty developers, that sounds like a terrible approach.

Calvin Correli: We don’t.

Brad Weimert: So, the only way that that can work in my head is if you have really high-class developers that are very good at what they’re doing. Is that your approach? Like, you want to bring on developers, less developers, but that are very good at what they’re doing?

Calvin Correli: 100%. Right. But it’s also coaching those people and motivating them. If they’re motivated by the bigger vision of what we’re doing and they get it, they’re bought into the mission, and they’re hard-working people that are grateful for the opportunity, not just like the money. That’s obviously part of it but for being part of the bigger mission and for all the coaching and education that they get and just being part of the team, yeah, that works super well. We have a hiring pipeline. We’re always hiring and we weed out like 99-point whatever percent of the people who apply because we’re just looking for those special few.

Brad Weimert: What’s the criteria to find those people?

Calvin Correli: So, we run them through some engineering problems like super simple engineering challenges which weeds out because like, that’s the first thing. If they’re not able to solve that, there’s no even point in having a conversation. So, I’m looking for people who address that smartly. It literally like takes you 5 minutes, maybe 10, to do some of these exercises. But I can see so much in how good you are in how you approach it. And so, that weeds out most of the people. And then we’re looking for culture fit. Are they people who are into growth and optimization and who want it? And then we trial people. So, like first 90 days is a trial like we take you through a bunch of steps but still you don’t know until you’re in and we’re just like, yeah, not a fit if they’re not, if it doesn’t work out.

Brad Weimert: And no geographic barriers to bringing people on.

Calvin Correli: No, except for like we’re not going to hire people in China because they might be CCP-influenced. So, we look at some of the legal environment of the country that they’re in. Yeah. Aside from that, no. And we have people right now in India. We’ve got a Russian who’s fleeing Putin’s conscription. So, he’s moved, him and also his family, to Thailand. And we got a guy in Canada. We’ve got a guy in Venezuela. We got a little bit all over the place.

Brad Weimert: Got it. What about background? How much weight do you put on previous experience versus how they handle your test?

Calvin Correli: Almost none on previous experience.

Brad Weimert: Oh, really?

Calvin Correli: Yeah. We want to see that they have experience with our core technology of Ruby on Rails because it’s too much of a learning curve if they’re completely blind and new on that. And JavaScript, everybody has to know JavaScript these days. But aside from that, not really. I tend to go after people who’ve been coding their whole lives and who have hobby projects, like people who love coding so much, they actually do it in their free time. Those are the kinds of people that I want. Like, that’s me, right? I will say I hired a guy recently who was a doctor and then transitioned into coding later only a few years ago, and he’s doing phenomenal. Like, he’s definitely more junior on the programming side but he’s so motivated and so hungry and he has all like where most programmers I think get really, really good at programming because we’re emotionally broken. He wasn’t, right? And so, that adds some of the other advantages to have an engineering team who’s not actually emotionally broken.

Brad Weimert: That’s interesting and makes sense to me.

Calvin Correli: Yeah.

Brad Weimert: Cool. I like that. So, before we got going, one of the things that you mentioned you take a lot of pride in is the client experience inside of Simplero and onboarding. But I guess let me back out. Can you give me, before we go into client experience, for reference, can you give me some construct kind of where you are right now and I guess we talked about employees. Are you okay talking about revenue?

Calvin Correli: Sure.

Brad Weimert: So, where are you now in terms of revenue? And where do you anticipate going or what’s the next steps to growth? What are you working on now?

Calvin Correli: Yeah. So, team size is about 30 people, revenue, 4 million, and my focus right now is building that customer acquisition engine that allows us to consistently get customers because we’re virtually unknown in most of the world. We’re more known in Scandinavia where I’m from, just because that’s where I started and had the biggest network. And so, more people heard of us because that’s the only way that people pretty much hear about us is through word of mouth. And so, that’s my focus now is actually building the marketing that matches the product and the customer service.

Brad Weimert: Yeah, I love that. So, product and customer service have been the focus forever, basically. You grew up a developer in a software company, so that makes sense. That’s all you’re doing. And now you’re embarking on a journey to actually market the product which you have not been doing. All accurate?

Calvin Correli: Yeah.

Brad Weimert: Yeah. Well, I think that that’s also a really great lesson for certainly the people that are sort of just at the, you know, obviously, the audience are people that are in that space and leveling up and there are definitely people that are brand new entrepreneurs that listen at sort of every threshold on the way to that number. People look at it and think, “What am I supposed to be doing right now?” Everybody wants to have this perfect system. I shouldn’t say everybody. A lot of people have in their head this notion of other businesses have it all together and they’re all perfect. And the reality…

Calvin Correli: They are. For the record, they are, especially ours.

Brad Weimert: Yeah. Okay. Aside from ours, no businesses are perfect and everybody’s sort of just trying to f*cking figure it out. But I think it’s super important to look at businesses and realize that you can grow to 4 million or well beyond without even a marketing plan, right, without actually putting energy into that.

Calvin Correli: Yeah. When you put that energy into product and customer service and just making sure people have a great experience, you get referrals, which is the only source of new customers that compounds.

Brad Weimert: Yeah, totally.

Calvin Correli: So, even as we’re adding the marketing or customer acquisition side of things, we’re definitely going to keep that because that makes everything else work so much better.

Brad Weimert: Yeah. Well, based on and we’re on the front end of this, but based on the feedback that we’ve gotten from our clients that use your platform and based on kind of our initial view of it, we’re excited about helping with the marketing side of things and getting exposure to the coaches, consultants that work with Easy Pay Direct to be able to see the platform. But what I want to hear about is what that customer service or client experience looks like, what the elements are, how you built it, what’s great about it that allowed you to functionally get your business to a notable size without any market.

Calvin Correli: Yeah. So, in all honesty, actually, our onboarding experience wasn’t that great. So, new customers come into the platform. It has all of these features and tools, and it’s like, “I don’t know where to start.” So, that problem, we haven’t been that great at. What we have been outstanding at is whenever people reach out, we treat them really well. We listen carefully to what they’re asking for and we give them a thoughtful answer, oftentimes record a video showing them, “Hey, here’s exactly what you need to do,” and all of that stuff. And it’s kind of simple stuff. It came from me. First of all, I’m someone who just, personally, I derive so much joy from just being of service to other people where it’s not transactional but I just know that I’m making a positive difference in another person’s life. That gets me off. And if I can really relate to that person on the other side and be human, I enjoy that. Flip side, I enjoy receiving great customer service also. So, it’s really something that I’m passionate about.

And so, in the beginning, it was me doing that customer service and I would just be like, “Hey, Brad, that makes sense. Yeah, I see what you’re saying. You know what? That’s actually a little confusing how the product works. Let me go change that,” and then write back and say, “Hey, now I changed it.” And we like to do that whenever we can of like, hey, if there’s something that you’re struggling with, that’s clearly something that is just unclear, we could do better or it’s a great idea and it’s a small effort to implement that we can do that right now in like 30 minutes, like, let’s just do that. But the whole thing is about empowering the people on the team now that it’s not me doing it but empowering the people on my team to relate to our customers as a human being. And it’s not natural for most people to do. It’s weird. Like, once you start to speak on behalf of the company, people want to start talking like, “We apologize in advance for any inconvenience,” like talk like robots or something. And, yeah, it works.

Brad Weimert: Yeah. We have a theme in our office which is be professionally relaxed and it starts from the beginning of training and is the through line because the last thing that I want to be as a financial institution is perceived as a financial institution. And actually, let me say that a different way. I definitely like the perception of a financial institution but I want sort of fintech, not traditional banking. Right? I don’t want the stuffy canned responses.

Calvin Correli: Totally.

Brad Weimert: Right? And nobody really wants it. What people want is respect, comfort in knowing that there’s credibility in the response. People know what they’re doing and that they’re going to be able to take care of you. But then they want relatability, right? They want somebody that they can just communicate with. Yeah, I love that.

Calvin Correli: And empathy, right? Like, hey, like people oftentimes when they’re angry or frustrated or scared and seeing that like and usually if they come off as angry, it’s because they’re scared underneath or some other emotion. So, just acknowledging that like, you know, seeing through that surface to, hey, there’s a person there that’s actually really struggling. Let’s see if we can help them feel heard, seen, respected, calmed down so that we can, but not in a patronizing way, in an empathetic way so that we can solve the action problem here. And in general, too, is like we treat our customers as if they’re actually smart, intelligent people, and not like, great, which is, I don’t know, it sounds pretty obvious but I think a lot of times we’ve all had the experience that the customer service rep is responding to us as if we’re morons. And like, “No. Yeah, I tried that. And if that worked, I wouldn’t have reached out to you.” And on that note, too, we make an effort to give a complete answer even if we got an incomplete request.

That back and forth where like you say something like they need to hear from you again, and then you need to write like that’s so annoying. So, we built a lot of tools into the platform that allows our customer service reps to figure out what’s going on, even if you didn’t tell me. So, for example, if you submit a review, if you reach out to our customer service people about like something like, it won’t do the thing and you’re not telling us what it is that you’re working with. They can see the last 10 pages in the app that you visited so they can try to, “Oh, it’s probably that thing,” and a bunch of other tools that we’ve built so that they can try to figure out what you’re actually asking, even if you’re not asking it.

Brad Weimert: Very cool. I love that. Yeah. One of our core values is we make things easier and we explain in our basic training what that means. And one of the parts of that is we do things that other people don’t have to, even if it takes more time. And your frame of one of the things I’m about to say is we give complete answers even when people give incomplete questions. And so, we go through a couple of examples of this in our basic training. I love the parallel here, which is if somebody sends you a one-sentence response and it doesn’t make sense to you, don’t respond to them with a question mark or that’s my least favorite thing in current text communication. F*ck off with your question mark. What does the question mark mean? Instead, you respond and say, “Hey, I’m not totally clear on what you’re asking, but if you’re asking this, here’s an answer. And if you’re asking this, here’s another answer for you.”

Calvin Correli: Exactly.

Brad Weimert: And, yeah, it takes you a lot more time as the support person. But really it’s the Stephen Covey quote of, “With people, fast is slow, and slow is fast.” If you take your time on the front end, you’re going to reduce the amount of back and forth, which reduces the ultimate friction, frustration, etcetera, and hopefully, that’s ultimately faster.

Calvin Correli: Yeah. And then there’s the culture of actually giving a damn, right, which really helps too. When you have people that actually care about our customers, actually care about giving good service like that, everything is easier.

Brad Weimert: So, how do you cultivate that? Is that start with hiring? Do you do weekly meetings? How do you build that culture with a distributed team?

Calvin Correli: Yeah. That is, I mean, it starts with hiring. And it’s all of those things, right, the weekly meetings, the culture we do. We’ll do ticket checks, we call it, where we just go in and dive into like how do we handle a random situation and just see what can we learn, how can we make that better? But I was very fortunate to hire these two incredible ladies early on. Beth is Head of Customer Success. She’s actually kind of transitioning to be my Chief of Staff now, and Deanna, who runs our customer support team. And they’re just incredible and they’ve just run with this and built it based on like what I started and what I envisioned and they’re just executing on it like gangbusters. And it’s really like when you see it, if you go to Trustpilot and see the reviews there, like probably three-quarters of them mentioned our customer support.

Brad Weimert: Yeah, that’s big. So, on an ongoing basis like, tactically, what are the check-ins that are reinforcing the cultural elements that you want?

Calvin Correli: For this support team, it’s different because engineers are very different from the customer success staff, right? So, on the customer success team, it is that weekly cadence of checking in with everybody meeting and setting. You know, they have an amazing culture and camaraderie on the team. Also like just internally, the way we operate is like there’s no politics, there’s no backstabbing. One of our core values is real talk. Just be real with people that goes internally as well as externally. All right. As you can see here, me, I’m just like sharing some of all my things that I’ve messed up along the way and all of that stuff, right? On the engineering side and on the whole team side, we do an all-hands call once a month. On the engineering side, it’s honestly more tricky but like, again, hiring for culture fit and then also just to some extent just letting engineers be engineers, right? Some are more, you know, social than others. But as long as they show up with the right attitude and they are bought into the mission, that’s good.

Brad Weimert: Dig it. Okay. Where do you want to take the company? So, you’ve been building the platform, the product, the service for years. How long at this point?

Calvin Correli: Thirteen.

Brad Weimert: Thirteen years. And it started with just you and your software project and it’s grown. Where do you want to take it in the next three to five? How far out do you think and what do you want to do?

Calvin Correli: Yeah. I want to grow it. I want to keep growing it into I think it can be like, what does that nine-figure company like $100 million company? Like, I don’t see why I wouldn’t be able to do that. Stay private. We’re bootstrapped. I own 100%. I’ll probably do some like employee/strategic advisor equity thing at some point but at this point, I own 100%. I don’t plan on taking on any venture funding or anything like that. I like that we’re only accountable to our customers and our team members. So, keep growing in that company. I don’t have any plans to sell it. Usually, like for me, the joy is in my everyday life. Success to me is a feeling that I get from having an optimal daily experience that’s sustainable. That’s success to me. I’m always successful. I don’t have any like destination that I need to get to. I’m already successful. I want to create that feeling of success consistently for me and my team members and my customers. All right. That’s my goal. And we’re there. So, then now it’s just fun. Like, how can we grow it so you can have even more resources to make it even better? And just keep doing that, keep growing it.

And then for me, personally, I’m interested in I want to create other things. Like, what else can we create with this kind of spiritual approach to entrepreneurship? Again, I love customer service, so I have a vision of creating a series of coffee shops/co-working spaces. I don’t know if you ever like the laptop people were everywhere, and we’re like, “Where do we go?” There’s WeWork, which is kind of depressing and boring, and there’s not much of a sense of community and you can’t just, like, easily drop in. And then there’s coffee shops but it’s always like then they play weird music or like it’s not really a good experience either. So, I have that concept, like, I have this concept for hotels that I want to do one day like I have all kinds of business ideas. I’m super big on health. Actually, I have a meal replacement powder and some workouts that I’m going to rebrand as Simplero Health. So, the plan is to do Simplero Health, Simplero Lounges, Simplero Hotels, Simplero all of the different things. So, that’s where I’m going.

Brad Weimert: Fun. Do you have a sense now of like, if you think about your current structure framework that you’re operating from now? Obviously, it started as one, right? And you’ve got kind of the structure framework that you’re using now. Do you envision that changing at the next benchmarks in revenue as you grow or as the size of the company changes?

Calvin Correli: Oh, 100%.

Brad Weimert: What do you think kind of the biggest shift in product development is going to be?

Calvin Correli: It’s going to be hiring the product management and maybe project managers and coaching them up to be able to do what I do at a certain level, right? You know, I think if you look at a company like Facebook, Zuckerberg is still ultimately the product visionary. If you look at Elon Musk just bought Twitter like Elon is the product person at Tesla as well, right? So, he has obviously a bunch of product people at each of those companies but at the end of the day, he is the ultimate product visionary, product person that says, “This is where we want to go.” So, I envision that always being the case but having that middle layer that I can coach up and thinking the way that I do so they can handle most of it and I only need to set the high-level direction.

Brad Weimert: Dig it. Well, I know that we both have things going on here very shortly. So, there’s a lot of things that we talked about that are super tactical for people that are building, certainly software, but also principles that apply to everything else. If people want to find out more about Simplero or you, where do you want to point them?

Calvin Correli: Well, there’s websites so Simplero.com and my personal website. CalvinCorreli.com. And then I’m Calvin Correli on all the platforms, Instagram, Twitter, TikTok, YouTube, all of it.

Brad Weimert: Dig it. Well, there are 15 other questions I could ask you about those things, but we’ll leave it at that, man. I appreciate you carving out some time.

Calvin Correli: Appreciate it.