How Do I Know When I’m Ready to Launch?

You aren’t alone. There are millions of Americans stuck working their 9-5 jobs with dreams of one day running their own small business. Eventually, some of them will take the leap, while the more risk-averse individuals may stand on that ledge for years or even decades. This is the million dollar question- how does one know when they are ready to take that leap, part ways with their current employer, and commit full-time to their passion with no turning back?

I could tell you how it happened for me, but I thought it would be more useful to interview several other small business owners in various industries to see if I could find a common denominator and really try to understand what separates those who take the leap and those who stand on the edge for eternity. For this blog, I interviewed a few friends of mine who started companies in various industries- a cannabis company, an aerospace technology company, a hotel, a cleaning company, and a brewery.

I’ve found that in order to deem yourself ready to launch, you need to consider three variables- your skills, your plan, and your mentality. The skills and plan are the easiest of the three to check off- so in conducting my interviews I really tried to focus on the mentality and understanding where motivation comes from. But I’ll share a bit about the skills and plan from my own personal experience.


In my experience, art and graphic design has always been a passion. With no formal education, my desire to learn and master my craft was self-motivated. It really wasn’t until I landed my first apprenticeship at another design company that I was able to benchmark my work against the rest of the industry and realize that my work was on par, and even better than many of the other designers in this field. I was always teaching myself new styles and techniques in Illustrator through Youtube tutorials, Udemy and Skillshare, but also was able to learn about how to streamline my design process by working with some of the best in the industry.

If your skills are not on par with or better than other established businesses in your industry, then you are not ready to launch. Commit a few hours a week to sharpening your skills, and really trying to understand how you can improve. Websites like Skillshare are only about $100 a year. As your skillset grows and you reach a point where you are confident that your product or service will yield happy customers, you should consider your plan.


I’m not much of a planner. When I launched GoodBoy, I didn’t have any sort of concrete plan- it was really just a loose idea in my head. That didn’t mean I didn’t consider what I was getting myself into financially. When it comes to planning, the most important thing to consider is how you will handle your finances. Marketing/advertising/accounting and many of the other aspects of your business you will learn as you go through trial and error.

Consider your current cost of living. At the time, I was living in an apartment with my fiancee that costed $950/month. I was responsible for half of that, or $475. I lived in a rural area where the demand for housing was much lower, and I was able to keep my costs low that way. All utilities were split two ways as well- my internet was $50/month, I didn’t have cable, my electricity was about $80/month, my car payment was about $70/month, food is about $600/month and my car insurance was about $45/month. In total, I could live comfortably for about $1300/month. For many of you, these costs are probably higher, especially if you have debt. But there is always room to adjust your budget and bring some of these costs down. Find out how much money is required for you to live comfortably.

If you divide that number by 4, you will get your weekly cost of living. I require about $340 a week to cover my cost of living. I needed to pull in about $400 per week (before taxes) to sustain my lifestyle at the time.

Now, consider how much money in savings you have. I knew that in launching my business, realistically I probably wouldn’t hit my $400 requirement per week right off the bat. Maybe I would, maybe I wouldn’t. Expenses are high in your first few weeks of business so you should plan for a loss. I wasn’t in the best financial situation when I started GoodBoy, but I at least had enough savings to cover my cost of living for about 3-6 months. Most of my savings were tied up in retirement accounts but I had some liquidity to get me through a few challenging months. How long could you go without making any income? What are your startup costs? 

After analyzing this data, I came to the conclusion that I would have about 4 months of trial and error and burning my savings to get myself to a point of sustainability and make enough income to cover my cost of living. And to me, that goal was very realistic. When you don’t have a 9-5 job, you have an infinite amount of time to commit to figuring out how you are going to make enough money to survive.

When it comes to planning, there are plenty of people or companies who can help you with advertising and accounting, etc. What is most important, from a planning standpoint, is to figure out how much time you have to get to a point where you are making enough money to sustain yourself. 

Once you have your skills and your plan, you just need the mentality. I could tell you how it happened for me, but I thought it would be more useful to interview several other small business owners in various industries to see if I could find a common denominator and really try to understand what separates those who take the leap and those who stand on the edge for eternity. For this blog, I interviewed a few friends of mine who started companies in various industries- a cannabis company, an aerospace technology company, a hotel, a cleaning company, and a brewery.


Through talking to these small business owners, I realized that in order to be mentally prepared to take the leap, both “push” and “pull” drivers are probably necessary. If you have always wanted to start a small business, I would consider that a “pull”. You are drawn to an idea. This passion of yours is beckoning to you, constantly whispering in your ear and telling you that you were meant to do this.

Andrew of Kind Acres Farm said his passion for growing cannabis started out as a hobby to supply a few friends. “When my friends were asking for more than I could grow I knew it was time to take the next step into a larger setup”. Andrew’s passion pulled him into the cannabis industry at the perfect time and now runs a hugely successful operation. 

In each and every interview I conducted, I found that not only was there this “pull” factor, but there was also a “push”. When I say “push”, I am referring to an invisible force that is pushing an individual out of their current position. For example, some individuals felt unappreciated at their work place, some felt like their managers weren’t taking full advantage of what they had to offer or realizing their full potential, and others just simply felt like they were capable of much greater things, myself included. It is equally as important to have a drive to leave your current position in life (a “push”) as it is to have that passion for your craft (a “pull”).

Do you have the “push” and the “pull” factor? What now?

Tyler, owner of Pristine Cleaning Co. said “For me it really came down to just having the confidence to know that I could succeed in making a living on my own”.

Kyle, former SpaceX engineer and owner of Prime Lightworks Inc. said “There was a day when I was not sure if I was ready to start and a great friend of mine told me you just have to go for it. He was right.”

I can attest to both of these. For me, personally, I had quit my job because I felt unappreciated and was just about to start a new job at a different company. The morning I was supposed to start, I realized that this new job really wasn’t changing anything for me. It was the same position, but for a few more dollars an hour. I didn’t show up to that first day of work. Instead, I realized that this is it. This is the day that I start my business. I needed to just do it and not look back. I had that “pull” factor for many years, but this realization that my position in life was not going to change unless I took a serious risk was the ultimate “push” factor that allowed me to take the leap. It wasn’t that I was in a great position financially to do this, but mentally I just couldn’t continue down this path I was on.

Justin, owner of Hostel of Maine in Carrabassett Valley, said “For us launching meant diving in when we felt like we’d regret not doing it more than we’d regret starting and failing”. If you have a business idea that you are obsessing over in your mind, there is no reason to believe those thoughts will just go away on their own. Especially if it’s a feasible idea and something you are passionate about. It is likely that those thoughts will always linger, and even amplify anytime you run into issues in your workplace. I knew that I would eventually launch GoodBoy at some point in my life, but I just kept putting it off to avoid the risk, thinking I would wait until later when I’m in a better position. The truth is, if anything, my position only got worse and I launched anyway. 

In addition to having these “push” and “pull” factors, a landmark event or catalyst has to occur. If every day in your life is pretty much the same right now, it is likely that it will remain the same until something new happens. Try something new. 

Tyler did some traveling, and just having the opportunity to see new things really allowed him to open his mind and see that the world is much bigger than the confines of his cubicle. Kyle was working on prototypes for a renewable aerospace technology and had a breakthrough realization that inspired him to pursue a specific type of technology. Justin happened to stumble into a real estate listing for the perfect property, and having a more concrete visualization of his dream inspired him to proceed with the Hostel of Maine. For Andrew, the growing public acceptance and legality of marijuana was a huge catalyst to his success. In my case, I started a new job (and left immediately). Sometimes an external catalyst will trigger you to take the leap, but sometimes you just need to find your own catalyst. Seek out new opportunities (or travel!). Talk to other small business owners. Become inspired.


I’ll end this some wise words from Brady, owner of Yes Brewing in Westbrook “It takes patience to bootstrap small companies from your imagination…. But I cannot express how gratifying it is to create things that encapsulate your personality and your desired contribution to the industry you enter and your community at large”.

Everyone I interviewed was scared to take on the added risk and responsibility. We all spent too much time on the fence. But in the end, none of us wanted to live a life of regret. There may never be that ideal moment to start your business, so why wait? If you are there mentally and have somewhat of a workable plan, then it is very likely the only thing holding you back is yourself. It is a survival skill and part of our own human nature to avoid taking on risks that could endanger our lives. But just remember- there are a lot of great people in this world who will support you when you do take the leap. 

If you have any questions related to starting a business, or if you need help coming up with a logo or website for your startup, please feel free to reach GoodBoy Design and we are happy to help bring your ideas to life. 

How to Come Up With a Logo Idea

One of the hardest parts of creating branding for your company is coming up with your initial idea. Sometimes you have too many ideas, sometimes you don’t have any. I’m going to tell you about a trick I use that can help you narrow your focus for what your logo should represent. This is something I learned from an online course many years ago and it has stuck with me all along. I don’t always end up using the ideas I extract from this exercise, but it’s a great starting point and at the very least can get your thoughts flowing. I’m not sure what the technical term for this process is, but I call it a “brainweb”.

To begin, pull out a blank sheet of paper and a pen, and write down the name of your business. If there are multiple words, write them in various locations on the page and space them out. Think about core values, or other words that are unique to your business and write them to the page, again, making sure you leave plenty of space between them. Once you have some core words that represent your business, you are now going to do a freewriting exercise where you branch these concepts out into other related words. For each word, write down everything that that word makes you think of, surrounding each word with related ideas. Draw lines to connect them back to their core word. The most important step here is to avoid filtering your thoughts. Nobody is going to judge you. Write down absolutely everything that comes to mind and build out a web. Repeat this process for each core word. Once you have a second layer of ideas on the page surrounding each core word, continue branching out the web and looking for more connections.

You aren’t done until you run out of room on the page. Eventually you should reach a point where you have some newly found bridges that connect your core ideas together. In the example pictured, I was able to connect GoodBoy to Graphic Design with “Fetch” and “Deliverables”.

Graphic Design>Files>Deliverables>Fetch

Fetch is the perfect way to connect the two ideas, because a “goodboy” is a loyal companion that seeks to deliver happiness (and sticks!) in the same way that a good graphic designer is looking to fetch you the best logo ideas possible. Combining this idea of fetch with other concepts in the web, I decided to make my emblem a skull with a bone in it’s mouth. The skull is a masculine concept, but I illustrated it in a very playful way where it is retrieving a bone the same way your loyal companion fetches a stick.

Maybe your “brainweb” didn’t get you anywhere. Try starting with other core words. What products/services do you offer? What makes you unique? What is important to you?

GoodBoy Design can help you with your “brainweb” process, or if you’ve already had success in this exercise we can help bring your idea to life! Contact GoodBoy Design today, your loyal companion.

Squarespace, Wix, or WordPress?

Squarespace, Wix or WordPress? 

There are many factors to consider as you begin to think about which platform you would like to use to build a website for your business venture. Wix, Squarespace and WordPress are some of the most popular site-building platforms, and to this day I still use all 3 of them for different purposes. Some people pick favorites, but I think there’s a time and place for each of them. If there wasn’t, then one of these would eventually go out of business. This same philosophy applies to your business and its relationship to the industry you are in. You will be competing with other companies who are really strong in some areas, but if you can find your place in the market and offer something that excels in other areas, you can coexist with no fear.

No matter which option you choose, I recommend paying annually rather than monthly. The cost savings are pretty significant, and I think one year is a fair amount of time fully evaluate the platform. In this post, I will address the cost of each platform, and other strengths and weaknesses.  If you are serious about starting a business, I don’t think cost should play any role in your decision. You should only be concerned with cost if you are unsure about starting the business to begin, or if it is just a hobby. I’m going to ignore the cost of domains for simplicity, which usually is about $20-25/year no matter which platform you choose. For hosting, I recommend you do not use a third-party to host your website. It’s a lot easier to host on these platforms and keep everything in a single pane of glass.


The cost of running your website on Squarespace is $216/year for the business package. As your free trial period comes to an end, they may even offer you a deal  where you can get the first year for about $175. 

The greatest strength of Squarespace, by far, is the ease of use. If you don’t have time to commit to learning how to build a website, this is your best option. They give you prebuilt templates that are constructed so that your website can translate easily to a mobile device too (we call this “responsiveness” in the design field). Another huge plus, is that they include G Suite with your subscription so you can have an email address @ your domain. The other options have added costs for this feature.

Using drag and drop, you can easily move stuff around and load the template up with photos and text. If Apple made a website builder, this would be it. Now of course, there are some downfalls. Your ability to customize and move things a fraction of an inch are pretty limited. Squarespace is meant for people who don’t want to deal with coding, padding/margins, etc., so if their templates don’t work for you, there’s not much you can do.

To sum it up, Squarespace is the lowest cost of all the three options, easiest to use, and takes the least amount of time to set-up. You can get a nice, clean looking website built fast even if you have 0 experience. But your customization options are limited. Overall, I think this is a great starting point if this is your first website. After one year, you may decide to try something else.


The cost of running your website on Wix is between $216 and $324/year, depending on the package. They have a lot of different options to choose from, depending on which features you may need (online shop, logo design, etc.). Many of their options include Ad Vouchers for Google ads, which is pretty nice! However, Google ads are quite expensive so $100 doesn’t get you very far. 

Similar to Squarespace, this company wants your business and will often send you promotional offers toward the end of you free trial that can give you significant savings on your first year with them. In my experience, they offer better first-year promo deals than Squarespace does!

The greatest strength of Wix is the ability to customize with little knowledge of coding. The amount of widgets, stock photos, editing options and other web elements out of the box is virtually unbeatable. Wix does have much more of a learning curve than Squarespace, but once you figure it out, you can get quick with it. It is very slick, but because of an overwhelming amount of features you may feel lost for a while. If you are very tech-savvy and are willing to invest a bit of time into building your website, Wix can bring your vision to life. Unlike Squarespace, Wix makes it easy to move things around (even a fraction of an inch) so you can make everything perfect. One of the downfalls here is the way they handle responsiveness (as we talked about earlier). You can build a perfect website for desktop, but you will need to invest many hours into tuning up the mobile version of each page you built.

To sum it up, Wix is in the middle cost-wise, and allows unlimited customization but requires an investment of time to get things looking nice. If you have time to invest and are willing to watch YouTube tutorials and read guides to learn the ropes, this may be my top recommendation for building a website yourself. Once you get the hang of it, your options is pretty much limitless.


The cost of running your website on WordPress is $300/year for the business package. And you’re going to want the business package because the lesser options don’t give you access to their plugins. We’ll talk about plug-ins later. WordPress isn’t as good about giving you first-year deals as the other two options, but that’s because they know they are the best. The thing with WordPress is, you have to pay additional costs for just about everything. If you were to build a website using what they give you for $300/year out of the box, you probably won’t be all that impressed. 

It’s a very clunky platform. If you want to take advantage of the benefits of WordPress, then you should consider purchasing themes/templates on third-party websites (ie. Themeforest), which are about $60. Adding in Gmail costs an additional $120. The costs can add up. 

The greatest strength of WordPress is the library of plug-ins, and the ability to customize. Think “App Store”. The hundreds of thousands of plugins are all created by third-party developers for various purposes, and you can find a plug-in for just about any feature you could possibly need. You can use these to duplicate pages easily, to translate language easily, add web security, create unique widgets, create forms, or optimize SEO. The list is endless. Every aspect of every web page you build can be moved down to the millimeter, and your customization is unlimited. This may sound very appealing, but it can also be overwhelming. Learning how to navigate in WordPress’s clunky and uninspiring user interface is not very enjoyable. Sometimes you will run into issues with how your website is displayed and you will have to add some code to fix issues. Sometimes plug-ins will stop working because they aren’t up-to-date. Similar to Wix, you will have to adjust every single page to display properly on mobile. 

Quite frankly, the options are limitless but it is a lot of work and is the most expensive option. My relationship with WordPress is very bipolar- I have created some of my best work on this platform, but it also causes the most frustration and headaches of all of these options. That said, their customer service is absolutely impeccable. They are the only platform where I actually had to use their customer service because it’s so easy to mess something up, but their staff is amazing and patient and extremely helpful. I have some comfort in knowing that if I break my website, I have someone who can help me out (another benefit to letting them host your site).


In conclusion, if you are building your website yourself, Squarespace is the best for entry-level and allows you to build a nice website without a ton of headaches and the G Suite is a huge added benefit. Wix is superior to Squarespace if you are willing to invest double or triple the time because it gives you unlimited customization. And WordPress I would suggest leaving to the experts, like GoodBoy Design, because while it can create the most beautiful websites, it’s a huge pain in the @$$.

How Much Should Your Logo Cost?

When you are starting up a new business, or even preparing to rebrand an existing one,  your design budget is something to consider.

The truth is, between Fiverr and the top branding studios in NYC, you can pay anywhere from $10 to $10,000 for a logo. $10,000 sounds pretty crazy for one simple design, doesn’t it?

Before setting your budget for logo/brand design, consider the margins on your product/service, and come up with a rough sales estimate. Let’s say you are a screenprinting company and your margin averages out to about $10/shirt. If you went with the $10 logo option, you could easily make that back on one t-shirt sale. For the $10,000 design, you would have to sell 1,000 extra shirts to make back that cost. 

There’s quite a difference there, but if you consider the fact that a high-quality logo could score you some bigger customers who are willing to pay for premium services, you could actually see a return on your investment very quickly. As long as the high-end logo gets you 2 additional customers each year for 5 years, each ordering an average of 100 t-shirts, you break even. And that’s a very easy target to hit. It would be even more likely that you would make back the $10,000 in just 2 years, with 5 customers each of those years at 100 shirts a piece. Easy peasy.

$10,000 is certainly a lot for a logo, but the message here is clear. If you go with the $10 logo from Fiverr, you will have a much tougher road ahead of you in trying to land sales. A lower quality design will result in a lower perception of your brand. There’s no reason to make sales harder for yourself. No matter what you spend, you will get your money back in no time, so there’s no reason to cheap out too much.

We recommend shopping somewhere in the ballpark of $500 for your logo- this is just enough money to hire a good designer who can spend time with you on a quality design, but still a pretty low cost in the grand scheme of things so you can make the investment back very quickly.

Contact GoodBoy Design if you are looking for logo design/branding and we are happy to help pick out the right package for you.

Discovering Your Brand

It can take some time to discover what you truly want your brand to represent. And your vision for the brand may evolve as time goes by. There’s nothing wrong with that! Even some of the most successful logos/brands in history seem to be refreshed or altered every 10 years, like clockwork. It doesn’t matter if you are a new startup company or a well-established business, what matters is that your branding reflects your offerings/philosophies and can convey the proper message to your customers. 

As you browse options for graphic designers to help create/redesign your brand and you need some direction, it can be very helpful to play with several options to better pinpoint which style/aesthetic and concepts fit your brand best. In the initial design phases, you should always keep an open mind. 

Colors can be distracting in the initial phases, and ultimately, a good, solid logo should be able to exist in black and white and be legible from a distance. Start out by evaluating different concepts, styles and layouts. 

Having multiple designs to choose from for your logo gives you more to talk about with your designer- what you like and dislike. The more thorough you are with your feedback, the happier you will be in the end when you get your final design. Once the feedback is applied and a final design is decided upon, you can then think about how colors influence brand perceptions and come up with an appropriate color palette. 

You can get a logo on Fiverr at a really low cost, but it is unlikely you will have any sort of emotional connection to it. And let’s face it, this is YOUR brand. Your brand is important to you. If you hire someone to design a high-quality logo that accurately represents your brand well, you will attract the customers who are willing to pay more for your products and services, and can get the return on your investment within your first couple of months very easily.

If you are starting a business or thinking about rebranding your business, contact GoodBoy Design and we would be happy to discuss our Brand Discovery Pack! This includes the full design process with multiple compositions to choose from (see photos above), unlimited revisions, and a full deliverables package with various logo formats for different uses. There’s a reason why we have a solid 5 star record on Google- we want to help you and your business succeed. 

Waking Up From Work Podcast

GoodBoy founder Simon James was featured on the popular Waking Up from Work podcast for quitting his day job and starting two businesses at the beginning of 2020 to go full-time on 2 passion projects. Listen to episode 41 to hear about his journey!

207 News Center Maine

GoodBoy founder Simon James was featured on local news programming 207 for merch/album art design collaborations with local artists Shane Reis and George Foisy as a benefit for suicide prevention/awareness. All proceeds were donated to local nonprofit the JD Foundation, run by Cheryl Morin.