A Field Guide to Self Employment

After more than ten years in the web industry, Guerilla Labs began as my full-time employment on October 1, 2013. As I sit here at one and a half years, I want to look back and and share what that journey has been like.

I get asked questions all the time about starting a business, and I am no expert, but I’ve come to realize that my experiences — the specific decisions, considerations and results — are valuable to a lot of people looking to start their own things. So, this is an attempt to lay those items out in as clear a manner as I know how.

Please remember that I’m just one guy, and what worked for me might not necessarily be the best plan for you. Also, I’m no lawyer, so, you know, this shouldn’t be construed as legal advice.

The Fear

I had been thinking about starting my own business since I was in high school. Well, thinking may be a little strong since I never actually took the time to think about what kind of company I would start — daydreaming would be more accurate. But, here I was nearing my mid-thirties, and I had never stepped out on my own. Why?

The fear.

The fear of not having a “great idea”, of not being good enough, of not finding work, of not bringing in enough money, of being exposed as a pretender, of failing. That’s a lot of junk to get through. Sitting on this side of things, it’s easy to look back and realize how long I let those fears paralyze me — and, yet, also realizing those things aren’t real. The security that comes from working for someone else is an illusion.

And, yeah, I still fight the fear every week. This afternoon, I sit here writing about my experience, and while I’m recognizing all the things that have gone right a little voice in the back of my mind tells me that my most recent job was my last. But it’s a lie. If I can get past the paralysis, get up and do the work, then it still may not work out. Sure, that’s part of it. But there’s a really good chance that it will.

Why are you doing this?

Just like security is an illusion when working for someone else, there are plenty of illusions to be careful of when starting your own business. Freedom, money and time are the big ones. So, let’s settle this right now. Yes, I have more freedom, but I still have clients I must answer to (and bills to pay). Yes, I have more time with my family, but I have to be really careful with the jobs I take to not give that away (as I did during a few periods of the last year). But no, I don’t have more money, yet — and I may never make up the money I gave up to make this life a reality.

So, why are you doing this? Be sure to be honest with yourself, because you have to know what you’re willing to sacrifice.

If you’re doing this to spend more time with your family, are you (and they) ok in giving up on a certain level of income you may have become accustomed to over the years? If you want to make more money, are you willing to work longer hours or take on employees (and perhaps not get to do the work you’re most drawn to) in order to get there?

Take a long look in the mirror. Now let’s get started.

Getting Started

The first thing you’ll want to do is have a clear idea about the type of company you want to start. I did this by spending months chatting with a friend about this very topic. There were a few things I really wanted: no employees (nothing short of partners), being able to work on a wide-range of projects (I, and those I choose to work with, have a broad spectrum of skills, abilities, and interests — working on a logo one day and writing code the next was the dream), having a set of values that drives my work and getting to work with some really talented people along the way.

With the basic concept nailed down (and I’m happy to go into way more detail on my philosophies) we began working on a name. Eventually, “Guerilla Labs” rose to the top — it sounded cool, had some fantastic visual elements that we could play with and the meaning made a lot of sense. After a search through the US Trademark Database and looking up the business name availability in Tennessee (where I live), the name stuck. When naming your own company, be careful with names that have multiple acceptable spellings (I went with a single “r” because it looked better in a logo), names that sound like another word (Gorilla, in my case) and names that you may need to spell for someone. Sigh. I’m still happy, but come on.

So far, this is familiar territory for any designer. To take the next step, I would have to get into some things that I had no clue about. My advice to you: get a good accountant. You’re going to need one anyway, and they’ll be able to advise you on all the things that need to be done to set up your business properly.

After speaking with my accountant, I decided to setup Guerilla Labs as an LLC. You can run a single-member company under your social security number, but being an LLC gives me some financial protections if anything ever goes unexpectedly sideways. In Tennessee, an LLC costs a bit over $300 per year, and that seemed reasonable to me.

I obtained a federal employer ID number (this is what’s used instead of your social security number for tax purposes) and filled out the appropriate forms to establish the LLC in Tennessee (my accountant showed me everything I needed). At this point, I’d recommend also checking to see what municipal business licenses you may need — I also needed a business license through my county of residence (since I work out of my house). My local County Clerk’s Office was able to point me in the right direction.


Ok, so I just described all the legal stuff, but there was actually some planning I did before setting up the LLC and getting a business license. Lots and lots of planning.

I’m naturally a very cautious person. I don’t take risks. I play it safe. So, going out on my own was even more daunting than it might be for someone else.

To plan effectively for your business, you’ll first want to get a solid personal budget in place. You really need to know a couple of numbers — what you “have to” make and what you would “like to” make. For me, my “like to” was about the same as I was making at my corporate job, but my “have to” was about half that amount (if we tightened our belts, didn’t set aside for big vacations and cut out extraneous spending). If you’re married, please, please make sure you and your spouse agree to these numbers — they will share in the sacrifice portion of this as much as you will.

With my numbers in place, I started to work backward.

A big thing for me in this endeavor was working “regular” hours. But, wait, not all of my hours are billable — I have to write emails, create proposals, take care of taxes, make sure my books are balanced, pay subcontractors and on and on. And, I want time to work on “non-client” creative projects — things that may lead to more work in the future. After (ideally) setting aside Fridays for non-client work, and taking out a couple of hours a day for administrative work, I was left with 24 hours of potential billable time each week. In practice, I sometimes have more time than that, and I don’t get to spend my Fridays as I would prefer many weeks, but it gave me a baseline to run some numbers against. Also, I fully planned on taking time off with my family — hoping for about 4 or 5 weeks total each year.

Alright, so 48 working weeks each year times 24 hours, gives me 1,152 hours a year (or 96 hours a month).

But, I don’t get to keep all the money I make! Taxes are tricky. Being self-employed, I’m now responsible for a larger portion of my taxes than I was before, but I also have more deductions I can claim. Being the cautious type, and not knowing exactly how much I would be hit with taxes, I decided to set aside 40% of all my income for taxes. After that, I decided to take 10% of what remained to set aside for charity (I want Guerilla Labs to be a giving company) and 2.5% for “operations” (paying for Creative Cloud, Github and a few other things). That leaves a little over 50% of my income for me.

After looking at my “have to” and “like to” numbers, I decided my hourly rate should be $100. That gets me right at my “like to” number if I have a full docket of clients paying my full rate (but my time isn’t always full and my estimates aren’t always as accurate as I would like and not every situation warrants my ideal rate).

I then took that number to a handful of trusted people — a couple of whom I had worked for in the past. And, guess what, not one of them balked at the amount. With my experience no one found it to be unreasonable. My prior place of employment also worked with a lot of contract developers — all of which were paid from $150 to $250 an hour.

So, I knew my numbers were feasible, the company was viable and I was ready to take the next step.


Those of you doing the math as we go will know that $9,600 is what I would bring in each month if all my “billable” hours were accounted for, but I knew I wouldn’t get that out of the gate. Former freelancers also warned me about the “feast or famine” nature of this work. This told me that I needed to set some goals for myself.

The first goal was really a check on the continuing viability of the company. I was going to give myself three months to be making the minimum of what I needed, and if I wasn’t there then it would be time to start looking for another job. For me — and this is where I become really transparent — that amount was about $4,400 in revenue (to pay myself $2,200).

The second goal was to have a year’s salary in the bank. The thought behind this is that if I could build up that much money then I could smooth out the “feast or famine” periods. Ultimately, my plan is to live off of the revenue I generated in the previous year. So, let’s say I make (after taxes, operations and charity) $60,000 in 2015. That means I can pay myself $5000 each month in 2016 — regardless of what that month’s work looks like. I knew being able to know my family budget, and make things consistent, would take loads of stress off my shoulders. Ideally, I wanted to get to this point within 24 months of launching Guerilla Labs. It should also be noted that I planned to not pay myself anything for the first couple of months to allow myself to start getting ahead with what was in the bank verses what I needed to take home.

Third, knowing how hard I can be on myself, I created a revenue goals chart. This chart started my revenue goal at $3,000 for my first month in business, stepping that up to $4,400 by month three and proceeding upward to $9,600 by around month nineteen. This was useful when I had a slower month — like I did last summer — to look at the chart and be able to say, “I’m doing fine, I’m right on schedule”.

I’ll go into detail with how my financials turned out a little later, but I think it’s important to state right now how some of these goals worked out.

I easily met my first goal with the initial clients (see the next chapter) I lined up, which I think should be obvious since I’m writing this post after a year and a half.

The second goal has been a little more fluid. While I’m going to be really close to being a year ahead by about 27 months, my take home will probably about $3,500 each month instead of $5,000 (my “like to” amount) each month. I also attempted to spend a lot longer at my minimum amount ($2,200) than I probably should have (in an attempt to meet this goal sooner), and life happened instead — washing machines broke, kitchen cabinets needed to be fixed and I got a little discouraged. So, I’m slowing things down just a little bit on this front to give my family a little more breathing room. I feel great about where we are now, but I state this just because I think it’s important to be reasonable with your goals and how you approach them. It’s very possible to put stress and pressure on yourself that just isn’t warranted.

And the revenue goals chart has, while encouraging me in many ways, been completely irrelevant. I made well over $9600 in just my third month of operations and I’ve had months since where I have brought in no money at all. The pay cycle and cash flow issues inherent in this type of work make things really interesting. Really, instead of looking at a month you have to step back and look at the trends. A really big month for me almost always means the next month is low (just because payments were all stacked up at the same time). So, it’s helpful to keep an eye on the overall trend, but to not get too caught up in a single month’s results — either good or bad. The number that I’ve found to be most useful to me is the “money in the bank” metric. As long as that amount is going up, I know I’m in good shape, but even it can be misleading because I know there is a big check going to the IRS each quarter.

It’s Dangerous to Go Alone

There are a few things I feel like I absolutely needed before taking the leap.


I knew I’d need some savings to get started — and I’ve confirmed that in practice. The thing about working for clients versus a normal job is that money flow is way different. While most people are very prompt to pay, I still may be getting money for work I did two months ago. I’d strongly recommend having at least three months salary saved up so you can get started without mounds of extra stress.

My original plan, when I earnestly began working towards starting Guerilla Labs, was to work on some side projects until I built up about six months of savings. Eventually, I found this to be really difficult — for two reasons.

First, it’s just difficult to get the type of work you’d really like to be doing when you aren’t available during business hours to talk to clients. Second, working every evening and weekend to get to this amount was going to completely burn me out. Burning myself out didn’t seem like the best way to start a new business that would need a lot of my attention.

So, I realized I just wasn’t going to get to this goal (not in one piece, anyway). There came a point where I realized that I had about three months of savings (at my minimum pay amount) and I wasn’t going to get any closer. And it finally hit me that it was plenty to get started. If you can save more, great, but there also comes a point where you just have to start.

Initial Clients

I highly recommend you try to line up a client or two before quitting your day job. It’s important because you’ll want to get the cash flow rolling as soon as possible, and because it’s easy to get discouraged when you’re talking to people and just waiting on a job to come through. Also, a lot of this industry is built on “word of mouth” advertising, so you’re going to need clients to get more clients.

Before I left my old job, I was fortunate to get on a project with the awesome team at Crush & Lovely. I actually applied to a job posting for a front-end developer and after a couple of discussions it became clear that working for them on a contract basis was the best thing for them and me.

I also lined up three months of contract work with my previous place of employment. Now this was tricky, since I couldn’t really pitch the idea without telling people I was leaving, so it was an “all in” kind of move. I was a manager of eight designers and front-end developers with a lot of domain knowledge, and my leaving was really going to sting. Understand that I’m a very loyal person who hates to let anyone down, so this was very much an attempt to do the right thing while finding a mutually beneficial solution. A contract period made a lot of sense for both of us — it gave me some runway while giving them a generous period to transfer knowledge and get the team set. It was important that this not take up all my time, as I needed availability to work on and line up other things, so I ended up working for them two weeks a month during that three month period.

Trusted Partners

If at all possible, you’re going to want some trusted people you can work with. I was fortunate and already had several people in place who I could call on if I needed help, but if you don’t, then I’d highly recommend going to some meet-ups, shaking hands and trying to get to know some talented folks.

From the beginning, I was worried about losing out on work because I was already booked. This scared me because I knew doing a good job on a project would lead to other projects, so I didn’t want to pass on good opportunities. My “team” turned out to be invaluable in this area. When a project came in that I couldn’t handle on my own, I would ask if any of them could help. Their availability during off hours was fine since I was the point person on each project.

This arrangement worked well for myself and my clients. My clients were more than happy for me to bring in extra help, as long as I reviewed and vouched for the work (since it was my reputation that established the relationship initially). For me, it meant that I got to turn down a lot fewer projects than I would have on my own.

And for my team, it turned into a lot of lucrative side-work for them. I really want to be as fair as possible in this work. So, for each project, we simply divvy up the pay by how much time each team member worked (you have to really trust each other for this to work). So, I don’t make a higher percentage than they do (which is really helpful when an estimate isn’t super accurate and we end up making less an hour than we would like — because we’re all in the same boat). We’ve also all agreed to take 2.5% out of everyone’s checks to pay for business operations and to spread that load around as much as possible.


In this business, you’re also going to need some gear — computers, testing devices, software, services.

So, I said I had three months of pay saved up. That’s true, but I also had a bit more, and I knew I’d need it since I was turning in my MacBook and iPad when I left my job. Here are the things I ended up needing to buy:

  • MacBook Air
  • 27" Dell Monitor
  • Magic Trackpad
  • Logitech K760 Keyboard
  • iPad Mini
  • Adobe Creative Cloud (complete)
  • Github (organization bronze)
  • FreeAgent (for invoicing, time tracking and accounting)
  • Dropbox
  • Backblaze
  • Domains (guerillalabs.co, guerrillalabs.co, gorillalabs.co)

There are other things I’ve purchased since then. Things like: fonts, new software, a CodePen account, additional devices, more domains, hosting. The point is that you’ll have expenses — maybe a significant number — so make sure you have the money (and monthly budget) to cover those things.

Finding Clients

The number one question I get asked is, “How do you find work?”. The answer is actually pretty simple, but first let me tell you what hasn’t worked so far:


Sure, marketing has its place, and there may come a time where I find a need and use for it, but my small attempts at marketing thus far have come up empty — from a quality leads perspective. One specific thing I tried early on was a featured listing on Sortfolio for a couple of months. The investment wasn’t huge — $99 per month — but it just didn’t generate anything for me. Frankly, I’m just not sure the types of clients I work with even know about those types of sites, and if they do, they still don’t know who to trust — and that’s the big thing, right there.

So, what does work? Two things, actually — recommendations from personal contacts and Twitter (yeah, I didn’t expect that one either, but stay with me and I’ll explain). The personal recommendations piece is pretty easy to understand. When someone needs work that they don’t know anything about, they ask their friends (and will almost always hire who’s recommended to them if they can afford the service offered). I do the same thing when it comes to mechanics, getting gutters replaced or having cabinets installed, so this shouldn’t come as a surprise.

But, it’s key that you let people know you’re starting a business, and that they understand the type of work you do. For me, I just tell people that I work on websites, and they’ll recommend me to most anyone who says, “I need a new website”. Those jobs may not always turn out to be a great fit for me, but I’d always rather have the conversation (plus, giving people good solid — usually free — advice on the direction they should go is one of the things that I pride Guerilla Labs on). These connections have turned into some of my best work over the last year and a half, with a couple becoming relationships with a lot of ongoing business. It’s my belief that being friendly and doing good work will just lead to even more.

Before we get into the second piece, let me ask you as question.

Who do you want to work with?

Who’s your dream client? Who would you love to work beside if given the opportunity? I think a lot of us daydream about these things, but we never take actual steps toward making them a reality. For me, a lot of the people who I most want to work with are on Twitter, and I was already following them.

Now, I’m not what you’d call “active” on social networks. I don’t post much, and I try to not check things more than once or twice a day. But, I learned that watching Twitter was a key way for me to find out about projects that people might need an extra hand with. This, of course, probably isn’t true for every industry, but it is for the web.

So, every now and then I’d see a tweet saying something like, “Looking for a front-end developer to help with a couple of upcoming projects.” The typical reply I see on Twitter to this sort of thing is people saying, “Hey, I’m available. Hit me up if you’re interested.” The thought that normally goes through my mind when I see that is, “That sounds so arrogant. Why would someone look up information about you and get in contact when you can’t even be bothered to introduce yourself like a real person?” And I know Twitter is limited to 140 characters, so there isn’t a lot that can be said, but there is a better way than just “buzzing the tower” with a tweet like that.

I’ve been hesitant to talk about this, but here’s what I did.

First, you should know that part of my previous job was making hires. And I grew to hate resumés — they all looked the same, were super boring, and usually didn’t tell me anything real about the applicant. So, I set out to do something different, which turned out to be a personalized letter, which would tell people about my work in a more conversational way — focusing a bit more on my personality and how that person could see me fitting in than on past employment and collegiate honor societies. I wanted something nice, well constructed, but not flashy. Surprisingly to me, it seemed to really appeal to the people I spoke with.

When I would see a tweet of someone looking for work, I would find an email address to get in touch instead of replying on Twitter. I’d try to keep my email short (figuring these are busy people with full inboxes), basically saying that I saw their tweet, that I’d love the opportunity to work with them, providing a super brief (2 sentences) insight into my work, and linking them to the personalized letter for more details. As an example, here’s the letter I sent to Jesse Bennett-Chamberlain last spring (several of the details are way out of date now).

Another thing to remember is that you’re talking with real people. I know these are people who you’d really like to work with — and perhaps really admire — but ultimately they are no different than you. They aren’t supernaturally more intelligent or talented than you. If you’re going to start a business, you have to realize that you have skills that give you as much right to a seat at the table as anyone else. Please, don’t be arrogant, but also don’t sell yourself short. Be humble, be nice, talk to others like real people with the same hopes, dreams and fears as you. Respect their time. Learn from those with more experience.

But take action.

I’ve been very fortunate to have a couple of these opportunities work out, and I’ve been completely bummed when a couple of them haven’t. But, the only thing to do is to keep throwing my hat in the ring. You miss 100% of the shots you don’t take.

Parking Spots

…which reminds me of story. During my collegiate years, my university was undergoing quite a bit of construction — totally wreaking havoc on all parking throughout the campus. Yet, I found a way to get great spots next to my building almost every day. I would then irritate my buddies by bragging about what a great spot I got, and I eventually began informing people that I had the spiritual gift of finding parking spots.

That’s good fun, but there is something real I discovered: I was getting good spots because most people assumed the spots closest to the building weren’t open, so they would start with lots halfway down the street in the attempt to save time. But, there were spots right up front, ready and waiting for anyone willing to risk it.

Yes, it’s a bit silly, and like any metaphor, it doesn’t hold true in all situations, but I believe this really is the case in business. Be willing to risk going after those jobs that you really want. You know, the ones you think someone better and more qualified has already scooped up — the ones you think you have no shot at.

What do you have to lose?

First Year Clients

My first year saw me working with Jesse Bennett-Chamberlain at 31Three, the fine folks at A Book Apart, Crush & Lovely, Brand Aid Design (and a slew of great small-businesses through Brand Aid Design), LifeWay, Church Health Reader, Made South, The Riverstone Group and a few others I either can’t talk about publicly or have inadvertently neglected. I have high hopes for what’s to come.


I’ve already talked about finding my “rate”, but that’s different from deciding on how to bill. There are an infinite number of things that can be read about the merits of hourly vs. flat vs. value pricing. Truth is, they all have their strengths and they all have weaknesses. They can all promote undesirable behavior if used incorrectly, but each can be useful in the appropriate situation.

Typically, I go flat rate, and that rate is based on an estimate of how long I think the project will take multiplied by my hourly rate. Sometimes I’ll give a discount to get to work with someone special or for a longer guaranteed engagement, but you get the general idea.

The biggest downside to flat rate pricing is what happens when your estimate isn’t correct. Estimating accurately is notoriously tough. I’ve gotten better at it, but I still miss my estimates.

The next downside is how to deal with changing requirements. All I can say is that continuous communication and honesty are the most important things. It doesn’t help anyone to gloss over potential problems.

I can tell you that I’ve used flat rate pricing because it makes the most sense to most of my clients. Typically, they really need to know how much a project is going to cost before they can move forward. It isn’t enough to tell them, “I think it’ll take four weeks” when they know they’ll be on the hook if you miss that timeline. But, it’s super important to clearly outline what is (and what isn’t) included in a flat rate estimate.

One example I keep thinking of is my mother having her kitchen remodeled. She had to know the total cost so she could tell if it would fit into her budget. There were also certain options that it was clearly communicated would cost more if she opted for them later — things like granite backsplashes or a nicer finish on the cabinets.

My point is that there is a way to make it easy and clear for your client while protecting yourself from being on the hook for anything that wasn’t part of the original deal. Again, treat people with respect, try to make it easy for them, be nice, be honest, and things will work out favorably more times than not.

During the early stages of a project — when you’re asking questions, estimating and advising — it’s also important to remember that your client may not know everything there is to know about what they’re asking for. When they say, “I need a new website” do they know what that really means (similarly do I know what it means when I say, “I need new gutters”? I really have no clue about the material, staffing or equipment costs). Similarly, if someone were to come to you saying “I need a new car” what do you do? There is a big difference between a hatchback and an Italian supercar — in performance and cost. It’s your job to help them understand what is involved and find the best value to meet their business objectives. Trust me, their success is your success.

Through the last year, I’ve come up with a basic price list for some commonly requested items. That list may be valuable to share here (this list is for front-end development and CMS integration):


  • home page — $1500
  • additional pages — $300 each
  • “special” features — $300 each (base)

CMS Integration

  • setup — $500
  • templates — $300 each
  • “special” features — $300 each (base)


  • deployment — $100
  • training videos — $400

Note that this price list is a point of reference. Some projects require a completely different rate due to many variables, and I work hard to figure out those things during the estimating process. But, it’s a helpful baseline, and I’ll explain a few of those items. The front-end home page is so high because it’ll always include things like the branding, header, footer and navigation which are reused across all other pages. “Special” features include components that are more involved bits of interaction — things like fancy carousels, complex animations or a particularly unique layout. I realized these “special” items were what normally blew an estimate, so I called them out so the client understood what those items added to the overall costs (it also gave me a good way to communicate with designers I may be partnering up with). A lot of people wonder about the “training videos” item. I like to do simple screencasts as documentation for how the client will work with the CMS. Those videos have made a big impact and help reduce support calls after a project ends.

Looking Back: Year One Results

People have a hard time talking about money, and I’m no different. There’s just something private about how much we make and how much we spend. But, I think it may be very helpful to some of you to know what a first year might look like. What follows is as honest a look at my numbers as I can provide.

Also, before I jump in, know that I’m at a strange point to give results. My official financial year runs from January to December, but I have three months before 2014 that I would like to include (I’ll make notes to try to make it as clear as possible).

Gross Earnings

2013 (Oct–Dec): $40,113.25

2014 (Jan–Dec): $117,004.02

Subcontractor Expenses

2013 (Oct–Dec): $4,574.12

2014 (Jan–Dec): $37,368.01

Cost of Sales (Stripe and Wire Transfer Fees)

2013 (Oct–Dec): $121.01

2014 (Jan–Dec): $503.28

Set Aside for Taxes

2013 (Oct–Dec): $14,215.65

2014 (Jan–Dec): $31,854.40

Set Aside for Operation Expenses

2013 (Oct–Dec): $647.44

2014 (Jan–Dec): $2,128.74

Set Aside for Charity

2013 (Oct–Dec): $2,132.35

2014 (Jan–Dec): $4,778.16

Take-Home Salary

2013 (Oct–Dec): $0.00

2014 (Jan–Dec): $37,531.75

For those keeping score at home, the numbers don’t add up precisely — that’s because there are a few minor expenses, times where I was over on operations and a couple of project related investments that just aren’t worth going into. I feel confident that these numbers will give you a really deep insight into the financial workings of the company at this stage.

Don’t be fooled by my take home salary because that number is way different than the salary another employer may offer you. Remember that my taxes have already been taken out, so all of that is actually usable. To get a true feel for things, divide my number by twelve ($3,128) and compare that to the actual amount you deposit into your bank from your paycheck(s) each month. Also remember that I’m saving up to be a year ahead, and at this point I have money in the bank to pay my salary through the rest of 2015 (that’s $3,336 each month).

It’s also worth talking a little more about taxes. Let’s take a closer look at the 2014 tax year (as that is my only complete one so far). Since, at this juncture, Guerilla Labs is a sole-member LLC, the company taxes and my family taxes all go together somewhat. I obviously don’t understand all of it, which is why I have an accountant I trust, but the final amounts are certainly impacted by more than the numbers you see above. With all said and done, I set way more aside for taxes this year than I needed to — like more than double. But, I live in Tennessee, which doesn’t have an income tax, and I had a lot of deductions, so your mileage may vary. As it is, I’m going to continue to set aside the same percentage for 2015, and then maybe make adjustments if I continue to be as far off as I was this year.

Beyond the federal income tax (which includes the estimated quarterly tax payments — talk to your accountant), there are a couple of other taxes (at least in Tennessee) that I learned about. I paid a Tennessee franchise and excise tax ($100), a Robertson County business tax (~$50) and I filed an Annual Report with the state of Tennessee to renew my LLC (a bit over $300). There may be other things you’ll have to take care of depending on where you live, but figuring out these things was one of the things I stressed the most about (and am the most relieved about now that I’ve lived through it).

All in all, I consider it a very successful year. A lot of people could complain about my take home pay, but like I said at the beginning, this is all about what is really important to you. I have no doubts that my salary will grow over time — up to what I had grown accustomed to in my prior job and beyond — but it’s certainly something to think long and hard about before you take the leap.

Looking Ahead

With year one under my belt and year two puffing along (and work being admittedly a little slower than I would like), it’s a good time to consider things and make appropriate changes.

The biggest thing I wanted to change about this year was being a little more selective about the work I take on. A completely booked up schedule, while a good thing, can mean having to pass up on some really big opportunities. With four really excellent relationships developed in my first year and a half, my goal for 2015 was to cultivate at least a couple of more with people I really respect — people I would learn from and enjoy working with. So, I reached out to some people on my “I’d really love to work with” list earlier this year, and I have high hopes that some positive things will come to fruition.

The other side of being selective with work is to guard my time a bit more. There were a couple of periods in 2014 where I had more work than I could handle, was super stressed out and was generally not reaping the benefit that I’d hoped this move into self-employment would bring. And even in the middle of that, I was scared of turning down work. I’d like to break that pattern this year.

I also continue to think about the type of company that I want Guerilla Labs to be. A lot of people recommend specializing in an area, becoming known for something that you’re better at than anyone else. And, it’s hard to argue with that logic. Most of my work in 2014 was in front-end development — something I think I’m especially good at. But I don’t think I want to narrow Guerilla Labs’ focus that much. I think I’d rather Guerilla Labs be known for really high quality work and truly excellent service instead of being only known for a specific type of work. I’m not sure if that makes sense. Maybe I’m just easily distracted and like to do different types of things.

People keep asking if I plan to take on employees. I don’t. I do hope to bring on a partner or two over the next couple of years, though. I’m lucky to get to work with some really talented front-end developers, designers, artists and illustrators. They’re some of the best I know of. And when one of them is ready to join me, we’ll be full partners. I just don’t know how to make this type of working relationship work if we don’t have equal skin in the game and equal ownership and motivation to make it succeed. Eventually I can see having an illustration branch of Guerilla Labs and an area that focuses on branding and maybe some other things.

And there are lots of other ideas constantly swirling in my head — I think it would be great to bill more on a weekly or monthly basis instead of a project basis, I would like to have more contract type relationships with companies (10–20 hours a month), I really want to get back into training and teaching people how to build things on the web, I’d like to figure out a couple of physical products I could spend some time on.

I guess we’ll see where it all goes, but I’m excited.


I have a lot of people to thank for their role in this journey. Tops on that list is my wife, who has been very supportive along the way, willing to participate in every sacrifice with me, and eager to have me at home more frequently. If you’re married, you simply can’t be successful in an endeavor like this without being on the same page with your spouse.

There are a circle of friends who have supported me and bailed me out along the way. Nick, with whom I sat and dreamed up Guerilla Labs, Woody, Justin and Tom: you’ve all been true friends, and I wouldn’t be alive and in one piece without you. These are the guys who keep me sane by swapping gifs and jokes on Slack while I sit alone in my office. Thank you.

I keep finding that the web industry is full of some really insightful and genuinely kind individuals. As I got close to launch, I began seeking advice from some people I admired. Noah Stokes and Jonathan Christopher were both very generous with their time and encouraged me at a time when I badly needed it. Thank you, gents.

And finally, a big big thanks to those who took a chance on me, especially Jesse Bennett-Chamberlain, Jason Santa Maria, Katel LeDu, Matt Blanchard, Jeff Schram, and Jeremy Mansfield.

I love you all.

Originally published at guerillalabs.co on April 17, 2015.