The Next Big Steps in Business—with Matt Gartland from Team Flynn

Matt Gartland: Yeah. It’s tremendously exciting, gratifying, and probably, mostly just a humble moment for me, and certainly for the team. Because as we’ve talked about today, we didn’t necessarily know, I didn’t necessarily know it was going to lead to this tremendous moment, right, but it naturally, I think, led there. You have always been . . .

Pat Flynn: You’re listening to one of my team members, Matt Gartland, who I have on the show today, to make a huge announcement with you about the SPI brand, about where I am in business, and about where we are in business. Matt’s been on my team for quite a while. Some of you may not even know what our relationship exactly is, and my relationship with the team is. I’m just going to tell you upfront, right here before we get into it, that up until January 1st, I was the only employee of my business, Flynndustries LLC.

Even though I had a team, I was still the only employee, on paper. I’m going to run through exactly how my business was structured, I’m going to run through exactly where it’s going to go, but we’re going to spend the first half, me and Matt, talking about what his superpower is and really why I love working with Matt. That is business operations, and how the inner workings of your business should progress, and how they should be organized.

Not every business is the same, but there’s a lot of principles that you will be able to take away from this episode—from Matt’s expertise as a manager, as a director, as professional—that you will enjoy, that you will find useful. We’re going to talk about our sprints, meaning how we as a team tackle larger projects and chunk them up. We’re going to talk about how we handle finances. We’re going to talk about how we handle hiring people and all that good stuff.

A pretty meaty conversation we’re going to have. Make sure you stick around until the end because we’ve got a huge announcement about where things are going now in the business, which may be a little bit surprising to some of you. We’ll see. I’d love to know what you think, but we’ll get to that in a minute. For now, que the music.

Announcer: Welcome to The Smart Passive Income Podcast, where it’s all about working hard now so you can sit back and reap the benefits later! Now your host—he and his son have earned a Victory Royale in Fortnite—Pat Flynn!

Pat Flynn: Welcome to Session 354 of The Smart Passive Income Podcast. My name is Pat Flynn. If you don’t know, I’m here to help you make more money, save more time, and help more people too. The goal of this podcast really is to help you grow and scale your business. You haven’t started yet; how do you get started in the right direction? A lot of the conversation we’re going to have today with my friend and birthday mate—I say that because we literally have the same exact birthday on the same year. It was really weird when we found this out, but we share birthdays, which is cool. I think we’re connected in way more ways than that, because we just love the work that we do together. We love what we are putting out. He and I are also partners in SPI Labs, which controls The Smart Podcast Player. We just have a lot of fun together.

As you can see, and you’ll be able to tell, there are moments during this conversation where I literally say, “I would never do what you do.” It just bores me to death. You’re going to see how we are able to complement each other. Hopefully, this may inspire you to, when you start to add more people onto your team, or perhaps start to train the people who are on your team already—how to be able to blend together in a way that can help the mission of your brand, and offer more value to your audience so you can make more money, so you can serve more people, so you can be more successful, and all those great things.

Let’s get right to the conversation today with my fellow team member, the one and only Matt Gartland. Here he is.

Matt, welcome to the SPI podcast. Thank you so much for being here today, man.

Matt Gartland: It’s a pleasure to be back. Thanks, Pat.

Pat Flynn: Yeah, you’re back on from a while ago, and you were featured in another interview with a few other people related to team. A lot of you who are listening to this now may recognize Matt and his name, Matt Gartland, as somebody who worked for me. I would call him my project manager for a while, but you’ve done so much more and we are going much bigger in the future. I wanted to spend this episode to talk to you about just where things were, where things are going, how you are involved, And hopefully, inspire others who are listening to realize just how important building a team can be, and how it doesn’t all have to happen overnight, but also inspire you, to share with you where it could potentially go.

For people who don’t know you, Matt, and your background, how did you even get involved with digital marketing and business in the first place? Let’s take everybody back before you and I met even.

Matt Gartland: Yeah, that’s a great reference point, because it’s been about seven years for me. I had just chosen to leave my enterprise career where I was an IT leader for Johnson & Johnson for the first six and half years of my professional career, right out of school, and had just become enamored with the web, with this confluence of web technologies and content. Because even in school, when I was studying the dawn of the web and modern technologies, computer science classes, I was taking classes about Roman history and Greek mythology, and media, and just loved storytelling.

When blogging really boomed in the mid 2000s, I saw an opportunity there to see and pursue some new growth for my professional career, so I left and started an agency. That became Winning Edits.

Pat Flynn: Winning Edits is the first agency you mean, that you had?

Matt Gartland: Yes. Yup, precisely right. First and foremost, we started with books because self-publishing was booming. More and more, people such as yourself eventually started to harness these technologies and platforms, and started to publish on their own. Self-publishing in the dawn of independent publishing was a great foray into digital media. Then that eventually grew into helping podcasters on podcasts. I grew into helping with web content, blog strategies, and email marketing strategies, and writing email sequences. It became a natural growth into more of a full-fledged creative agency, or a digital media agency.

Pat Flynn: Right, which is why it was initially called, like I said, Winning Edits, which was to help people with the editing in the process of book writing, which is where we connected first with my book, Let Go, in 2013. I hired you as an editing team to help me through that project, which was such a great experience working with you. Then we put our heads together to see what else we can do, and you offered, “Okay. Well, what else can we do for you?”

Then, like you said, it grew into everything else. Although it’s called Winning Edits, it’s really like a full-on agency that helps with all creative things that entrepreneurs have been able to do, even offline as well. It’s just been an amazing journey that followed, because a lot of you might not know that Matt was one of the first people I had ever hired to work for me, and it was for my book, Let Go.

Then through that, he and I just started to work together more for other projects, like we did some courses, we did some other web-related projects together. A lot of you might not know this about me, but Matt was the person who then was able to find Mindy who you may know edits my podcast and takes care a lot of the systems behind the scenes for me. Through Mindy, I found Jess who is my executive assistant who many of you have spoken to or have communicated with via email. Janna, my project manager for all things SPI, was through you as well. You’ve been an instrumental part in the growth of Team Flynn, but here’s the craziest part: I had still been a solopreneur, the only employee of Flynndustries up until January 1st of this year because I, instead of hiring employees which I was very scared to do, I found it was a great solution to just hire Matt and his agency to essentially become Team Flynn.

Then Matt, you were the one to take care of all the paperwork, the hiring, the firing and all that stuff. I just had to pay the agency, which was perfect for me. That’s been a wonderful relationship all these years. When you created Winning Edits, did you ever think that it would turn into something like that, like a full-fledged support system for a personality and a blogger and a brand like mine? Or like where had you envisioned it going, initially?

Matt Gartland: First, definitely not. I hadn’t envisioned this. I think that speaks to just, the entrepreneurial spirit that drives a lot of us to do our own thing. You do have vision of course. You start with a projection of a certain industry. You want to be in a certain skill. You want to start to develop more a certain impact you want to make, and all that’s written into value. With the folks I started to work with in the online space and just build relationships with, even that weren’t per se in a professional . . . Or definitely in a professional sense, but not in the contracted sense, so they weren’t hiring me. Getting to know Steve Kamb and Adam Baker, folks like that in the space, was just phenomenal. I knew that I wanted to contribute more of my expertise around team building, around leadership in general, in business, certainly build my own skills in that capacity, so I wanted an opportunity to run my own thing, to bring really talented people into the mix.

I love team building as really almost an art form, how you really recruit for talent, train, and develop, and inspire that talent around common goals and visions, and be able to at the end of the day produce results, right? Being in the digital media space where we can move quickly and we can launch websites and develop courses like you’re mentioning . . . Breakthrough Blogging, I think was the first that we were working on together.

It made such a gratifying impact on myself to be able to work on the digital canvas across the media types. I knew that that’s where I wanted go, but I didn’t know how far I was going to go. I didn’t know how big it might get. I didn’t ultimately know where it would take me, outside of the fact that I wanted to stay at that intersection of content and commerce online with these digital platforms. It certainly led me to meeting you.

I think one important thing to mention here in terms of our story and our relationship and how it’s grown is that nothing was ever forced. It was all very natural. It’s like, “Where could I help you,” right? You said as much yourself, coming out of the Let Go project. With all of our clients over the years, it’s never been forced. I almost say as a joke that I’m a pretty bad sales guy, because I don’t like that conventional approach to sales. I don’t want to force anything.

If we can add a value and we can help you, let’s please have a conversation about it. If anything never feels right, no hard feelings. Like, that’s okay, we’ll step back. With the folks we’ve worked with, some awesome brands recently—Courtney Carver of Be More with Less in the minimalism space—like, we tried to add value where we can. That’s led to obviously doing a lot with you, Pat. It’s been just about the most remarkable, grateful experience of my career.

Pat Flynn: It’s been a lot of fun, man. I had always envisioned that I was going to be a one man show. That’s why it’s called Smart Passive Income, like, let’s create these systems and find the tools to make everything automated. I eventually found out that I couldn’t do everything on my own and it’s not just about the tools. There’s a lot of human touches and people that are needed to grow and scale and run a business.

Now, I was by myself for nearly six years before I started working with people. That’s not to say you should hire a team right away. I felt it very valuable to work on things on my own, to edit my own podcast, to edit my own blog and create my own website. That was all very valuable, but it made me appreciate more what it was like to hire people who could do those things better and faster than me.

It made it worth the time and the money to find those people and obviously, pay those people as well. You were really huge in the development of me, understanding that I could actually hand things off and things would still be taken care of. Like I said earlier, you were initially coming on in my eyes and in my head as the project manager, the person who I was the idea guy and you would be the implementation: “Let’s get everything organized,” and, “Pat, I’ll let you know when I need you for the implementation of this thing.”

It’s grown to become that, but then so much more. Now you are in charge of things like the other members of the team, the HR related things, the business side of things, a lot of the finance side of things as well. Again it’s just like, I think about what it was like when I first started. No, I didn’t even think I would ever have a team like I have now, but it’s been so important, and as far as like, the bigger goals that I have with FlynnCON coming up, the big ambitions to help make a change in education, I wouldn’t be able to A, get this far but B, even think that far ahead without a team behind me.

I think what I want to ask you first, Matt, for everybody who’s listening right now, is when it comes to team building—and a lot of the solopreneurs who are listening right now, I know they’re on the fence of like, their first hire and finding people to help them. What would you say in terms of those people who really want to make an impact and balancing, starting a team which costs money and it takes time to learn how to manage those people, versus just the perhaps ceiling that they’re at now with only doing things themselves? How do you help a person through those decisions with finding other people to help them?

Matt Gartland: I think the first thing that you need to do is to embrace empathy, and try and start with some measured risk. I think that as entrepreneurs, as business owners, you can never avoid risk completely, so do start reaching out to folks and asking for, first and foremost, sort of one on one introductions. The big sites that are out there where you can search and post job recs and hire freelancers are great, and I’m not disparaging of that, but I think that if you can get personally verified introductions like, quite frankly, you and I have, right?

You didn’t find me through some job posting websites. I’m pretty sure it was Adam Baker that made the introduction between us. If you can find people that you know and trust to give a very verified recommendation then take that risk and put them on contract, definitely recommend a contractor status first, especially for first time solopreneurs that are inviting other people into their orbit.

Do a three month project to six month project. Do that as a 1099 contractor. Especially for folks that are yeah, the “idea guy,” step a little bit further down the road there and be sensitive to the contract, get excited even about some of the details and try to work on what the success looks like. How do we define success together so that the outcome of this project, whether it’s a fixed project or whether there’s some continuity to the engagement? Sometimes those materialize retainers or other forms of agreements.

I think being united in a common definition of what success looks like to both parties continues to foster goodwill and continues to align incentives. It continues to promote value exchange, because value at the end of the day has to be at the center of everything. That’s the serve first ethic that obviously you champion. It’s imbued in a lot of the core values that I’ve had through my career, through Winning Edits, through my other agency that was in the ecommerce space.

So long as we can, at the end of the day, feel good about the hard work that we put in and the value exchange, now that’s where you start. Don’t rush into hiring people, I don’t think, unless maybe you’re listening to this and you’re raising venture capital, and you’re in the tech space, and you’re going to build the next great startup, and you’ve been really successful with fundraising—then that’s a different conversation.

I have some little experience there where okay, if you have major investment, you’re going to need to hire a lot of people. That needs to be full-time focus. I don’t think that’s the conversation we’re having today. I think this is about trying to build, dare I say, lifestyle businesses, right? Things that maybe grow a little more organically and slowly, and then build trust with each other through these stepping stone experiences, toward what might become a more permanent, longer lasting relationship.

Pat Flynn: When it comes to hiring, I know one of the hardest things to do is find the right people. You’ve always impressed me with how you’ve been able to hire people that just seem to fit my mission, our culture with SPI, and everybody else who’s already on the workforce. How do you even start that process? Let’s say people listening, it’s them and one other person but they’re ready for their next hire. It’s such a scary thing to insert a new person into their lives who they’re going to be working with.

How do you find that person? I know you said recommendations and things like that, but how do you even know they’re going to fit in, not just with doing those tasks, but like into the culture and to just the mission of the brand overall?

Matt Gartland: Great question. I suppose there’s a couple dimensions here. One is, first and foremost, know yourself. Know yourself first going into it. What is your mission? Have you written it down? What are your core values? Have you taken the time to really critically think through what those things are to you? Write those things down. What is even the business plan for the year, right? To accomplish that business plan so that the business plan fulfills the mission, what talent do I need to bring to bear to accomplish the work that supports the plan that supports the mission?

These things stack. I think first and foremost—as you and I have worked on together for SPI, and so are we maybe a work in progress, but getting these things down on paper so that you can communicate this, and you can say it to a potential candidate that is interested to work for you and with you that like, “Hey, this is what success looks like at your company. This is what we believe in. These are our core values,” whether those core values are just three or five.

Knowing it yourself so that you can clearly articulate it is part of the recruiting process, and then even further down the road so that you can hold people accountable. Accountability, when we speak of culture, cultivating culture, nurturing culture, and then expanding that culture especially when you have a distributed team like we do, as like, most work forces are tending to shift toward, having this . . .

There’s like, content. It’s a version of content, albeit for an internal audience. You have to develop that well. It has to have a story, it has to have a purpose and has to be something that you know so intimately well yourself before you can get others enrolled in that vision. That’s number one. Number two is you got to start before you need it. Yes, lean on your direct relationship. Yes, start building out your potential org chart, not in any super crazy formal way, but just start thinking about, again, the things you might want to be doing in terms of major projects to support your brand and grow your audience and add more vitality into the business.

Identify that in advance. I know that’s a little bit of a cliché, and then it pops up in different aspects of life, but if you need it tomorrow, you’re starting too late. Start that process now so that when you do need to activate something, a potential new role, job rec or something, you have a network more established in that regard.

Pat Flynn: Totally. One thing you mentioned was like, business organization and including systems and those things. That’s one thing that you’ve been able to bring and inject into what I do very well so that we can scale, so that we can grow. I know a lot of entrepreneurs are like me, where when you get started, you just figure things out as you go. You’re on your own, it’s a Frankenstein contraption that you’re creating as you go along.

Some of it works, some of it doesn’t but hey, it may help pay the bills a little bit and you’re growing slowly. When you can add a little bit of professionalism and a lot of organization on top of that, which is a lot of what you brought to the table, Matt, things can then start to grow exponentially. This is the difference between, in the first few years of my business, generating mid six figures per year, to now we’re in the millions of dollars per year.

You’re somebody who had a major factor in that. How do you, for the scrappy entrepreneur, begin to inject a little bit of organization into what you do? This is one of your specialties, Matt, is just the organizing the thoughts of a business and turning it into something that’s manageable and can more easily grow because of that. Like, where do you begin when you . . . Yeah, go ahead.

Matt Gartland: I start on the finance side. I definitely love and geek out over the numbers as you will know in my insane spreadsheets. You don’t have to immediately go, however, to complicated spreadsheets to apply organization and method to your business operations, though I would start with numbers. I would start with some finance things. First and foremost, understand your costs. So many freelancers and small businesses that I interact with, that I tried to help in some capacity, don’t really have a good handle on just how much they’re spending.

Two basic counts here. One is to organize what would amount to your fixed costs, the things that are either truly stable cost for month to month, or that have very minimal viability to them. It’s sometimes like, your utility bills fluctuated a little bit. Figure out what those things are for your business, and that establishes your first baseline. Second are your variable costs, the things that are more discretionary spending, the things like your meals and entertainment if you travel, if you go to conferences, if you’re coming to FlynnCON.

All of that would go into a professional bucket of expenditures so that you just know truly, “Okay, what am I spending?” That’s in the red. That’s on one side of the ledger. The other is certainly revenue; it’s the money that you make. To understand that and to do that purposefully—of course, understand the business that you want to have and make sure that you’re building the business you want. It’s really easy to chase dollars, especially in the short term.

I can definitely speak to that in the services arena, when you think about the services space, if you think about agencies, if you think about growing agencies. I’ve struggled and made mistakes in the past, both with Winning Edits and the ecommerce agency. It’s like—it’s easy to grow a new service line just because maybe you have one client asking for it, or because it’s the hot new trend, but is that really the caliber and the quality of work that we want to be doing?

For a brand like SPI, are we investing in the right products? What’s the next course that we want to make? Is this something that adds real value, that adds lasting value? Structure your revenue streams around the things that you want to be doing. How can you add more value over time in those same revenue streams?

For SPI, as we think about podcasting being a critical pillar to the brand, how can we continue to add value around the skill in the podcasting channel? What new products and experiences can we develop and add a ton of value in that will make a difference in the lives of other podcasters and other content focused entrepreneurs? Structure it that way. Start having then, some basic math like, “Okay, this is what I want to charge for this thing,” whether that’s a service coaching relationship or podcasting.

“How many new clients do I need to get at a certain price point?” You can plug it into a spreadsheet if you want, just start to get that structure. Then when you start to marry up those two sides of the ledger, you’ll start to figure out your profit. I know that, Pat, you’re a proponent of the profit first mantra and methodology. I know it’s taking off more, it’s becoming more popular. I think that’s a really good starting point for our folks that maybe get a little bit nervous when they think about, “My goodness . . . like, a P&L, what is that?” Right?

A profit and loss statement like, “My goodness, these numbers are scary.” They don’t have to be scary. Taming anything is what takes the fear out of it. You got to look at it. You got to stare it down a little bit. Start slowly. Think about profit first I think, especially when you are starting to think about transitioning from maybe side hustle freelancer to full-time freelancer. Then maybe from full-time freelancer to a little bit solopreneur, starting to work with other people.

Pat Flynn: Can you explain a little bit about what the profit-first mindset and principles are?

Matt Gartland: Yeah, certainly that the common thinking is that you take your revenue, you take your expenses, and you hope that you have some positive number at the end of the day that would represent your profit when you subtract your expenses from your revenue. That’s the traditional approach, in the most simple and basic of terms. What that . . . At least the argument goes, what that potentially allows for in terms of habits and behaviors, even mindset, is a certain maybe disregard for expenses, or not being as disciplined with how you’re allocating your expenses into the business model.

It might even have some perverted incentives: “I’m going to go to ten conferences a year and spend all of this money on airfare to get there, right, because I’m investing in networking.” That’s true. You need to invest in networking, but that might be a backwards justification for all of this expenditure, right? If you flip that around and then say, “Okay, if I am working a nine to five day job but I’m really trying to plan my exit from that and I want my side hustle to become my new full-time thing. At the end of the day, how much profit do I need to be making, as a business of one, to be able to support myself and my family? Okay, here’s my number.”

Okay, now to get to the number at least on annual basis like, “if I need to be making $100,000 a year, how do I reach that number? I need to probably be spending a little bit of money to do some networking and to start a business, get the legal entity stuff formed. I’m going to need to be spending some money maybe with a ConvertKit or Teachable, or other SAS-space software platform, just to help run the business. All the platforms like Harvest or FreshBooks for like, invoicing during the services space.

You need to establish your cost basis, but you need to know what your profit number is first so that again, you’re supporting your family. Then you can back into that cost basis. You can also back into the revenue number. The revenue number is not going to be your profit number because again, you’re going to have a cost basis somewhere.

Pat Flynn: Right. It’s almost like revenue minus profit equals expense, so you build the business that would reflect the money that you need, or that you would want.

Matt Gartland: Yeah. It’s not a sexy term, but it’s like cost controls, so it’s like, “Okay, if I do that equation and I arrive at the expense budget . . .” right? It’s like, “Okay, that’s a constraint.” I have to operate within that constraint around what choices I’m making around those expenses so that I can hit my profit goal.

Pat Flynn: Right. It’s almost like when you are planning for a retirement and they always say like, pay yourself first. Instead of paying the bills after you get your paycheck and then seeing if there’s anything leftover, you have a little bit of money that you know is going into your own accounts for building a nest egg, and then you pay your bills. It’s like a reverse way. I’d definitely recommend reading the book by Mike Michalowicz I think is his last name—Profit First. [Full Disclosure: As an affiliate, I receive compensation if you purchase through this link.]

A lot of people in my Accelerator Program are really enjoying that process. It’s one of my top recommended books for last year that I read. Now when it comes to . . . Another thing that you help to add value with what I do, is not just organization of just the business and the finances and how that’s all run—which again has been just massively game changing—but also just how projects have been completed.

You brought something into my life that I’ve never done before, which is sprint planning. I’d love for you to explain to somebody who like I said is a scrappy entrepreneur, or they’ve got a small team, and they work on a, “Let’s just take it as we go,” thing. How do we migrate from that feel and approach to what it is that’s called sprint? Where did that come from and how was that implemented?

Matt Gartland: This is then geeking out on the operational side for sure. The sprint planning process comes from the world of Agile Software Development, that I’m betting a lot of listeners have heard before if you’ve read Eric Ries’s book, The Lean Startup. It’s this concept of breaking down what you want to accomplish, whether it’s a web project, a content project, just building in the information production into smaller component parts. Then being able to sequence those into a set unit of time intervals. So we use two week sprints so that you can have more focused, measurable progress, you minimize your sense of overwhelm or the team’s overwhelm, you can have more progress. You can be more flexible, even through that process where in the first sprint, there’re two things you’re going to accomplish, but you get those built-in feedback loops. [Full Disclosure: As an affiliate, I receive compensation if you purchase through this link.]

You can be more either, say agile, which is probably where the term comes from, responsive to that feedback and adaptability to creating that end product. When we think about—especially again with how flexible and adaptable we can be with content, with podcasts, with blog posts, with even the creation of again the information products that we do—an iterative-based methodology to organize the work, organize the people, the staff, keep them aligned to promote high-touched communication, this two week process . . . It can be one week, it can be four weeks, but we have found that two weeks works well for us. It promotes that caliber of productivity and closeness within the culture that we need to be successful.

Pat Flynn: Yeah, absolutely. We’ve found that, or I found that we’re able to produce a lot more stuff when we break it down. We have different things that happened within a larger project happening in a shorter time period. We know who’s responsible for what and those things. That’s been really helpful. Can we just go over an example of how one might approach the creation of an online course? We’ll have Janna on later in the year to talk about the more specifics of project management, which is what she’s on board on Team Flynn to do.

This really stems from you, and I’d love to know like, let’s say that we are creating an online course and we’ve validated it. We’ve talked to people about it. Maybe we even for example pre-sold it, but we want to build it now and create it and then launch it. How might you approach that in a sprint-like manner?

Matt Gartland: Certainly. There’s the concept of the beta group and the beta tester that may not even need to have all of the content available for that group in terms of a beta release or a beta roll out, so we can structure our sprints to accommodate maybe a smaller portion of the overall curriculum or of the overall content experience that we need to create. We can chunk that down further into certainly the different aspects of an integrated media experience.

It’s like an online course. That’s the video production that you and Caleb run with a whole bunch, developing of the scripts, doing the raw video recording before production and post-production. We can break out the copywriting for the landing page and for the email launch’s components for a nurture funnel, if we have a nurture funnel. We can break out the graphics certainly in all the branding that we do for the courses, and making sure that that’s really tied into the brand identity across the board for SPI.

We can find all those individual items. We can put those into individual backlogs per person or per functional groups. Again, for the content team that’s doing most of the copywriting, for the creative design team that’s doing all the graphics and the branding production, for the videography team, which is chiefly you and Caleb and his team, we have the individual backlogs of all the work scope that needs to get done.

Then we can plot that against those time intervals. We can shorten those time intervals in how many we need. Again if we’re doing of a more phased rollout, where it’s a beta group and then we go primetime later—and that even packs up further like we just did with Amp’d-Up Podcasting, right, in Q4 of 2018, where we did a pre-sale, which was great. Certainly, the course wasn’t even fully done at that point, so we were able to compress, within a much smaller sprint window, all that we need to get done just to support the pre-launch component and then mature that forward in the future sprints to get ready for the beta launch.

Pat Flynn: What are some of the tools that a person might be able to use to help them with this management at this level of, in terms of detail for these projects and these sprints?

Matt Gartland: Yeah. In terms of say software tools, Trello was a fantastic starting point. It’s built around what’s called a kanban concept, where you can build lists which would amount to backlogs of different work scope. You can force-rank that based on your priority, simply drag and drop, and it’s free. I still love Trello. We use Trello still within the team to organize your sprint forwards and your sprint plans.

If you want an upgraded experiences, we had certainly geeked out a whole bunch on Airtable. It’s a spreadsheet on steroids. We’ve been doing some amazing, powerful things with it. It’s definitely a more complex system and you do have to pay for it. We have used that very efficiently for what we do in terms of our almost multigenerational planning. We do try to plan ahead not just really one sprint at a time, but really have a vision and intentionality to what is the first quarter and what’s coming up on the horizon.

Certainly when we talked about FlynnCON and everything that’s involved there, we have multiple sprints starting to get stitched together; we can still be flexible as the sprints roll along and as sprints get completed. That’s a big part of their value but nonetheless, we have a roadmap. We know where we want to go and we know at least with some really good and well-conceived hypothesis what we want to create can be nimble as we go.

We have that structure so that we can hit the target and say for FlynnCON, we know that that’s coming at the end of July, here’s everything we need to get done between now and then. It’s modularized so that we can be adaptable to feedback but nonetheless, we’re going to hit the target.

Pat Flynn: Right. It just shows you like when it comes to . . . First of all, there’s a number of things that happen consistently every sprint, right? There’s a certain number of podcast episodes that need to go out which means there’re certain people involved with editing at certain times. Behind that, there’s a time when we plan what those episodes are and all those things. Those are ongoing things that insert themselves into every sprints, certain emails that go out, etcetera.

Then for the particular projects, that’s where breaking things down ahead of time—you want to build an online course, okay, let’s see all that needs to be done. Let’s chunk them and let’s determine when those chunks are going to be taken care of and who’s responsible for those pieces. That way, you can actually start to begin to make progress. What I found really nice about this sprint, about the two week sprint process, is like, we know if we accomplish what we need to do within those two weeks that we are making progress.

By the time it reaches the end of that project, we know we’ll have met that timeframe. Of course, no, not everybody gets everything done within the every sprint, but by having those sprints stacked like that, we can say, “Okay, we were a little behind on our work on the first sprint, so let’s play catch-up on the second one so we can be on track for the third one.” It’s just really nice to have it all spatially laid out like that, versus the way that I used to approach these things was like, “Okay, I have this big giant project that I know needs to be done.”

I thought I was smart by just going, “Okay, I’m just going to work on the next step and hopefully it gets done by the certain day. As long as I focus on the next step, it’ll get done as soon as it can,” which is a better approach than just like, “Okay, I’m just going to let this sit here and do nothing,” but not as great as planning it out to this level.

Matt Gartland: Yeah, precisely. It’s about getting ahead and hopefully staying ahead and doing so within a set of constraints and a set of notes that promotes, obviously, a healthy culture. It doesn’t burn anyone out. It is open and honest in promoting feedback. There might be couple of questions that might be popping into people’s minds such as, “Do we use points to structure our sprints?” which comes from the true implementation of an Agile-oriented model. We do not use points, at least not yet. Points—

Pat Flynn: I never heard that. What does that mean?

Matt Gartland: Normally what we would do, especially if you had a devoted team . . . Again, Agile comes from the software development world, so your software team, say it’s in-house or just a fully contracted, though fully full-time, devoted team: That team, the team together has a fixed capacity. You can think of it in hours. That’s a decent starting point to understand, what is this team capable of doing within your fixed unit of time?

Okay, we have a team. We have eight people on the team. How much work can they do within a two week period? You can quantify that. You can work to quantify that, right? Hours is a good starting point and then a more mature point from there forward is the point, which is a more arbitrary unit of measurement that still has relative sizing so that, “Hey, this thing that we want to do,” the team would say, “We’re going to size that at a five. This other thing, in relation to the five that feels bigger, we think that’s an eight”. Really the end of the spectrum, the more extreme end of the Agile planning spectrum in terms of sprint planning is to get to a point where you essentially have a budget per sprint of 200 points. Then we’re going to spend those 200 points on these items in the backlog that have been sized, right? We’re not fully there yet.

We’ll see if we ever get there. We’re obviously being successful operating more sort of on teeshirt sizes, small, medium, large stuff, as well as, Pat, what you said. There’s a certain continuity to the things that we already create so that the podcast episodes are sprint over sprint, the blogs are posted sprint over sprint. We certainly know what the size of those things are, we know how much effort it takes.

Then when we do the bigger projects, there’s an internal conversation that happens around like, “Okay, how much can we throw to fit into, again, a sprint just based on sheer capacity?” That’s a much, much more mature concept if anyone loves just learning about that stuff. There’s a lot of resources out on the web about it. I love Eric’s stuff, Eric Ries’s stuff, so start with his stuff. That’s for down the road, but it is exciting, especially if you’ve learned out over numbers and capacity planning sort of in the same vein of like, just financial forecasting.

You can plug a lot of the stuff into a spreadsheet, do some cool math on it and start to see whether or not you’re making smart decisions as a business owner and as a leader to lead your team in a direction that again, you’re maximizing really on their talents but yes, within the constraints of their capability and their capacity.

Pat Flynn: Guys, you can tell that Matt’s at another level here. I just want to be honest with you, guys. This stuff that Matt’s talking about, like the points, just like the level of detail that Matt can get with the whole planning process of projects and all the stuff, and finances, his love for spreadsheets and stuff . . . like, I do not ever personally want to do those things. It just bores me. It’s scary to me. I feel like if I just change one number, everything like will break.

I know a lot of you feel the same way, but here’s the other trick about this. There are people like Matt that exist out there who love that, who that’s just the kind of world they live in. They want to serve business owners like us because they just geek out over the stuff. When you can align your mission and your goals and your big ideas with their detailed ability to create and to support, it’s a match made in heaven.

That’s why Matt and I have worked so well together. Man, I hope you don’t take offense to me saying that like, that stuff bores me to death, and I would never want to read about those things. I hope . . . I don’t know. I’m just curious, your thoughts on that, but I think for me—and you know me, I’m an idea guy. I’m an entrepreneur and not that entrepreneur that likes to get into the weeds of things. I just want to build and serve and create. All these other stuffs scares me which is probably why it’s taken so long for me to hire people and get to this point. What are your thoughts on that?

Matt Gartland: I am not offended at all. I take it as a compliment because like, I could—maybe I will write a book on this stuff one day, because a lot of the people listening to this don’t fit into one mold, right? Please, take a personality test. If you haven’t, go to It’s built off of the Myers-Briggs personality concept. It’s free. It’s fun. They have little avatar characters for all the different personality types. Get to know yourself.

When we think about leadership, it starts with self-awareness, right? Do you understand your strengths? Do you understand certain blind spots? When we think about entrepreneurship, Pat, we’re both entrepreneurs. We’re both leaders but just in different ways, right? You have talents that I don’t have, I have talents I think that you don’t have, and that’s where the magic comes from.

Can you build partnerships? Can you build alliances? Can you build teams that play to different people’s strengths? Can you create a symphony? Right? Can you orchestrate something that’s beautiful and that adds value, and that can grow and expand as you add like, almost new instruments into the mix? You can only do that if you think first about really understanding yourself, what you want to do, how you think about business, how you are motivated intrinsically and extrinsically.

To be told that I’m the nerd guy with spreadsheets like, that’s a compliment because that’s who I am. That’s how I’m hard-wired. At FlynnCON, you’re going to be onstage for two hours, like that would absolutely drive me into the ground. I love being more behind the stage, right? Behind the scenes, still being a leader, still having a really big influence on the thing, but I don’t need to be the guy onstage. That’s not me, as much.

Yeah, so for folks out there, and I definitely champion a lot of entrepreneurs if this speaks to you, that if you love being the operations guy, if you love being the finance guy, there is a big future there. More and more entrepreneurs, other entrepreneurs need that help. It’s not always about being the social media influencer or the person onstage. Those are amazing things if you naturally align yourself to that. If you don’t, like, please join my party. It’s cool just to be the nerd with the numbers.

Pat Flynn: Right, right. There’s a number of different names for people like that that I just want to make sure people know, because they’re looking for people like you who can help manage, and project manage, and develop the systems, and things like that. Sometimes they’re known as project managers, sometimes they’re known as OBSs . . . or what does that stand for? I can’t remember. Like operations in business-something.

Matt Gartland: I’m drawing a blank on that one. It’s in the op space for sure.

Pat Flynn: Yeah, operations . . . business operations. That’s the kind of terminology, because some of us, and I know a lot of you are in my camp, which is you just want to help people and you want to create, but all this other stuff is a hustle and it’s holding you back.

Sometimes the answer is to find that person. It took me years but, and I continued to grind in the beginning, until I found people who could help and compliment, who I saw there was value in what I was paying them, and I was getting much ROIs, result.

The big announcement today is really the fact that I’ve been working just as a solopreneur on paper for the last ten years. Ten years of business. I am, or had been, the only employee for Flynndustries for ten years.

The team that you know and that you’ve heard about had always been through Matt’s agency, Winning Edits. Starting this year, January 1st, so by the time you’re all listening to this, Winning Edits is no longer, because I’ve essentially hired Matt’s entire team, and Matt, to come on as legit employees, with like, all the things that come along with that. There’s a lot, trust me, because we’ve been doing the transition for the last few months now.

There’s so much paperwork, especially when you hire people from different states. We’re doing some other cool things, stuff that I’ve always wanted to do but was very scared to do. I think I’m at a time in business now, ten years later, where it’s time to step up, it’s time to put my big boy pants on. Things have been working really well. I’ve made over $6 million online doing it this way, but I want to go bigger.

Not just bigger for revenue purposes. That’s not even the primary reason, or not even near the top. It’s to help more people, to start to establish myself as a bigger online brand for the purposes of my ultimate goal, which is to help with kids in entrepreneurship and education. This is the team that I know can help take us there. It’s to help more people build more businesses so they can change the world in their own special way too.

I think it’s the perfect time: Ten years, FlynnCON coming. We have some bigger projects on the horizon as well, and more people to serve. I think it’s going to be a lot of fun. I’m also very thankful that I’m able to, at this point in life, support the team with things like healthcare and dental and vision, and a 401K plan, and paid time off. Team members and yourself, Matt, you’re like having kids and stuff. It’s like, very special that I feel like I can take care of you guys with the business that was once just almost an accidental entrepreneurial effort back when I first started, back in 2008 after getting laid off.

I just wanted to publicly announce that and let you all know that you’re going to hear from more of the team now that officially they’re team members now. Although we’re always known as Team Flynn and yes, you guys are also known as Team Flynn, we’re all in this together, but it always felt weird. Like I wanted to always throw a company party or hold a retreat, but it was never my team. It was your team, Matt.

I wanted to offer bonuses but like, that’s not my right to do, but it is now because now you’re all employees. Now there’s like, added pressure. Now there’s families that I have to take care of. I think it’s going to help push me to where I need to go, to do what I want to do and serve our mission together. Just thank you, Matt, and hopefully this inspires everybody who’s listening to this to realize that like I am just learning as I go with you.

I’m trying to grow and get bigger. I feel like this is the right time to pull the trigger on this. It doesn’t happen overnight. This is ten years in the making and you’re all listening to it now. Matt, I’m thankful that you’re one of the first to come on from the team, the official team, to share a little bit about what you do in your superpowers, and you coming on as the CFO and COO, chief financial officer and chief operating officer.

Big special shout out to Michael Hyatt, who’s a big inspiration for me, to go in this direction as well. I’ve just seen what his team and what he’s been able to do, and I want to follow his footsteps. Matt, I just want to say thank you. Any words or thoughts related to all that? I know that was a lot.

Matt Gartland: Yeah, it’s tremendously exciting, gratifying, and probably mostly just a humble moment for me, and certainly for the team. Because as we’ve talked about today, we didn’t necessarily know, I didn’t necessarily know it was going to lead to this tremendous moment, right, but it naturally I think led there. You have always been first and foremost a friend, but also our best client. We’ve done the most innovative, challenging, rewarding work for you, and ultimately for the SPI community, and are just so inspired by all the folks out there that we’ve been able to play some small role in, and will continue to now play a larger role in.

Going through an acquisition transition like we are is a big deal. The team is so excited. To be able to grow a company and have these components, where it’s the boring stuff maybe to many, but as you mentioned, healthcare and other forms of benefits—just being able to provide that future, right, is to me as, more than anything hopefully, a servant leader for the team because the team is so great . . . It’s a great moment for all of us. It’s the dawn of I think a tremendous or just even brighter future for SPI. I’m honored to be a part of it.

Pat Flynn: Thank you, Matt. Guys, I have a real company now, like it really feels like it. Not that I didn’t have one before, but for those of you listening, especially those of you who have been listening and following since the beginning, this is a huge moment. I didn’t think there was any better way to share this moment than with all of you here on the podcast and with Matt on board with us too during this chat.

I’m looking forward to highlighting Matt more and having him show up and teach. He has a lot of knowledge as you can tell that would be really useful for many of you. That’s a lot of knowledge that I don’t know how to teach, which is obviously why Matt’s there.

Many other member of the team are going to come up and be on the show and be featured. You’ll see them at FlynnCON. It’s just going to be a great environment. I’m just excited to welcome everybody on board officially as members of Team Flynn and Flynndustries LLC. For those of you listening, big momentous moment and you are here to hear it, and it’s the first time we’ve publicly announced this.

Matt Gartland: Yup, that’s right.

Pat Flynn: It will be awesome. It’ll be awesome. Very scared, very nervous, but very thrilled and excited, and all the best things that have happened in my past have always been in and around nervousness and excitement and a little bit of fear. I think that’s a sign that this is—we’re heading the right direction. My biography, which will maybe be written someday, I feel like we’re just in the first few pages right now, because we got a lot more to do and a lot more people to help. I’m happy to have more people on board to be a part of that story with me too.

Matt Gartland: Exactly. If I may, Pat, forgive me, but to riff on something there at the end, I want to acknowledge you because it is a truly momentous, significant moment for you, and to have seen your growth as a leader and as a CEO. We talked about the CEO mindset a lot, right? It has, just seeing that and working with you through this process, it’s been just really rewarding and inspiring to me to have seen your growth. Not just from maybe the last few months, but our whole tenure working together. I just want to acknowledge you and thank you for everything that obviously now exists before us.

Pat Flynn: Yeah. To finish off . . . Thank you, Matt for that, I appreciate that.

For those of you listening, you might be like, “What’s going to happen now? What’s going to change with Pat?” I think there really isn’t anything you have to worry about. If anything, having the team on board now fully means that I will be able to devote more time to thinking about ways that I can serve and ways that I can extend this mission, ways that I can actually execute on it and opportunity to think even bigger.

If anything, it’s all positive. I’m again very excited about having the team to support all these but hey, thank you all so much for listening and Matt, thank you for being here today and sharing. Do you mind if we get you back on the show later on? Perhaps, we can actually even ask people, now that they know your superpowers and what you’re involved with in the business, maybe on the comment section or on Twitter or Instagram @PatFlynn, you can comment with maybe a question or things that perhaps you want to hear more from, related to what Matt does in the business.

We can bring him on the show again to talk more about those finer details of whatever it is you might have questions about in terms of finances, operation, those things. Let me know in the comment section of this podcast episode or on Twitter or on Instagram @PatFlynn. Matt, where can people reach you in case they have a question for you, if you don’t mind them reaching out to you in some way, shape, or form?

Matt Gartland: Not at all. @MattGartland on Twitter’s probably best for questions and things. My last name has a T in it. Sometimes that gets forgotten, but otherwise, tons of fun coming on the show, would love to come back.

Pat Flynn: Cool, man. Thanks, Matt. I appreciate you, and we’ll see you on the next sprint call.

Matt Gartland: That sounds great. Thanks, buddy.

Pat Flynn: All right, I hope you enjoyed that rather meaty conversation today with Matt Gartland, who now you know is the CFO, COO, Chief of Operations in the brand.

I love the analogy that he often uses, which he didn’t bring in today but I loved it. Hopefully, it helps paint a picture of the things that you should be creating and can aspire to. An analogy that he likes to use all the time is that of, if you’re watching the news for example, you see the guy or the gal reporting the news. That’s voice you’re hearing, that’s the personality and they are the ones who are front-facing. Matt is the guy who’s behind the scenes running the show. They are touching the knobs and hitting the computer buttons and all those things. I just only have to worry about delivering that value to you, the viewer, or in this case the listener. The team and the engine is all running underneath.

No, it didn’t happen overnight. Like I said, it’s been ten years in the making to get to this point, but I feel like I’m putting my big boy pants on. We got a lot of big boy pants things happening this year, from FlynnCON—again if those of you are interested and if there are tickets still available, now would be the time to get it. If you want to check out FlynnCON and meet Matt and several other of the team members, they are going to be there to support that event and to support you.

You can check it out,, and we are right in the middle of planning all that and making it special for every attendee there. A family friendly event, no alcohol sanctioned by the event, and it’s going to be amazing, unlike any conference you’ve ever been to. It’s largely due to Matt and the other team members, us putting our heads together to create an amazing experience everywhere we touch—a blog, a podcast, a YouTube channel and especially at FlynnCON when we see you in person in San Diego in July.

Again, and hey, I appreciate you so much for listening all the way through. Let me know what you think. What do you think of this move? I know it’s a serious move. Now I have actual employees that I need to take care of. I kind of was taking care of them before in a way, but now it’s like there’s a lot of weight on my shoulder. You know what? I love that. I think it’s about time. Let me know what you think.

Hit me up on Twitter or Instagram @PatFlynn or if you’d like to shoot me a message, just leave a comment on the blog. All the links and stuff are there as well at Cheers, appreciate you so much. Make sure you hit subscribe to the podcast if you haven’t already. Team Flynn for the win. Let’s do it.

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