Hi! We're Jason and Caroline, a husband and wife creative team taking you behind-the-scenes of building our new business from scratch. Poke around and watch us figure it out as we go!

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The Challenges of Building Something Won't Get Us Down

The Challenges of Building Something Won't Get Us Down


In a perfect world, building a business is simply a certain amount of tasks executed over a set amount of time. But let’s be honest: None of us live in a perfect world.

(Also, who keeps giving us all these extra tasks!?!)

We aren’t sharing this post because we want your sympathy for the challenges we've encountered while building Wandering Aimfully. Instead, we’re sharing because it’s an integral part of the underlying ethos of Wandering Aimfully: to share the real-ness of this whole life and business thing. To show you, the amazing human reading these words right now, that even we (experienced online biz owners) run into challenges and stumbling blocks along the way. 

Challenge #1:

Our budget is blown and what we’re doing about it 


I wouldn’t call it a mistake, per se, but one thing we didn’t do when planning Wandering Aimfully (that we’d absolutely advocate most people should do): Create a budget. 

Budgets are great. Budgets are things we use in our life very frequently. In a future Wandering Aimfully post we’re going to breakdown how we run our weekly budget meetings (yes, weekly!), but for now, we want to share why we didn’t create a business budget and what we’re doing now that we’ve blown that budget out of the water. 

With Wandering Aimfully we have the mentality of: “whatever it takes.”

Whether that “it” is time or money, having a budget was kind of an afterthought (again, we do NOT recommend this). 

In the back of my mind, I was hoping we would build Wandering Aimfully for around $5,000-$6,000. That didn’t include the cost of all the fancy video/audio equipment I purchased, it was just the website and our backend dashboard for paying members. Essentially $5-6k would be spent on development and services that went along with development (Restrict Content Pro, et al). 

As of typing this post, we’re looking at $9,000 - $12,000 in developer costs. We’ve doubled the amount I had in the back of my mind, and to be honest, it sucks. But alas… whatever it takes.

This isn't just one product that we're thinking of launching and crossing our fingers will work out. This new business is the foundation of both our businesses (and our livelihood) going forward. It is based on an idea we've proved out the past three years through BuyOurFuture. We have two existing audiences that are eager to learn from us. So, this investment is far from frivolous.

Plus, Caroline and I both agreed from the beginning that if the membership business model is going to work, we have to be different. We can't just offer up links to all our previous products (like we've done in the past.) We need to create an experience that makes someone's life better. This custom dashboard is our answer to that, so it is worth every penny in our eyes.  


Two things are happening to cover the additional expense:

  • #1: Our developers are friendly enough to defer their fees out 1-2 months so that our cashflow situation isn’t left looking like a sad, sad pile of pennies. 
  • #2: We’re pulling money from our savings (read: profits from previous projects, namely BuyOurFuture). 

If we’re being frank with you: This sucks. It’s not ideal. But, we’re not letting our blown budget situation affect our decision-making or the quality of the product we’re building. We’re sticking with our product plan. We’re adjusting deadlines. We’re doing whatever it takes to deliver the best product we can to our existing and future customers. 


One thing that helps whenever any tough money situations show up is NOT to hide from them. By sharing this situation with you, it’s a bit of weight lifted from our shoulders. We talk about our busted budget daily, but it helps when you don’t harbor any shame or guilt and can share it freely about. That allows you to learn from any mis-steps and bring lessons forward into future products.

The other way we’re overcoming our blown budget is by making peace with WHY we’re spending the money in the first place. We want to build an amazing platform that attracts the right people. If those people sign up for the Wandering Aimfully Membership, we have a backend dashboard that helps (retain) them going forward. The investment we’re making up front of $9-12k will hopefully help us bring in $10,000 per month just a few months from now. It can be weird to think about building a business like you’d think about investing money in stocks or funds, but it’s not a bad way to think:

  1. Invest $12,000 to build Wandering Aimfully.
  2. Have an asset that we’re proud of and that our customers love.
  3. Get to our 300 paying member goal within a year-ish. 

Spend $12,000 to make $360,000 (annually). That’s a pretty stellar 2900% return on our investment*. 😂

*Sure, there are a ton of steps, time, and other costs involved to get to our 300 paying member goal, but the “investment” concept is one we’re buying into big time!

Going over budget is pretty damn common. I don’t think we could have avoided  it completely, but had we actually sat down, gotten price quotes from developers, and had a much more thorough scope of work, we could have done a better job being prepared to spend more than we wanted to. (So, if you’re building a project of your own, please do that!)

How can we see this obstacle as an opportunity?

Ever since I read The Obstacle is The Way by Ryan Holiday, I've changed my entire outlook on challenges. Every bit of an adversity is a crucial piece in getting you to where you're going, so how can you look at every obstacle as an opportunity instead? This is how we try to approach every challenge we face. 

In this case, we're looking at going over budget as an opportunity to really learn why having a build budget is so crucial. This dashboard is a completely custom build, and we now have crucial knowledge about how to prepare for and price a project like this in the future. We also see this as an opportunity to deepen our belief that this dashboard is a crucial piece to attracting and retaining customers. In the few moments we had to ask ourselves whether we were willing to curtail certain features in order to save money, we both refused to sacrifice our vision for the customer experience, which just showed us how central this idea is to our business strategy.

Challenge #2: 

Life sometimes takes a crap on your face

I couldn't think of a better way to put it, okay? What I mean by the above statement is that life can sometimes throw unexpected challenges and hurdles your way, ones that make everyday life and business much more difficult. 

In our case, this has come in the form of a lot of family health issues in 2018. When people you care about are hurting, you're willing to drop everything to do whatever you can to help them and it takes a lot of mental energy on a daily basis to offer up the support you want to give. 


These issues are mostly affecting Caroline, who, as you probably know is a super sensitive person. Some days we have a to-do list a mile long, but one phone call can send the day in a different direction and that's okay. Family is super important to us, as is taking time to process and deal with these life challenges, so we're not beating ourselves up over these tiny moments of getting off track. We're reminding ourselves that being there for family is central to our values so that takes priority. 

How can we see this obstacle as an opportunity?

For Caroline, I know the first part of the year has been tough, but she has a real sense of gratitude for how much closer it's brought her to her family and for showing her what really matters to her. For me, it's been hard to support her through those different emotions, but I also see it as an opportunity to strengthen us as a couple and as business partners. I'm sure this won't be the last time that life throws us a curveball while we're building something, so we're now better equipped to face that in the future. 

challenge #3:

PayPal: arch nemesis and necessary evil

This challenge has been looming in the background for us, like a nocturnal predator. It's been waiting in the shadows, ready to pounce. 

Well, PayPal pounced, and it pounced hard last week. 


One decision we made when starting the build of Wandering Aimfully was to move away from Gumroad for payment processing (what we’ve been using for BuyOurFuture) to Restrict Content Pro

While our technical setup with Gumroad was working, it felt like a house of cards, ready to crumble to pieces at a moment’s notice. 

We chose Restrict Content Pro as our new payment processor because it was built to do exactly what we want:

  • Accept credit cards AND PayPal for payments
  • Create recurring payment subscriptions with no additional work from us
  • Have a system in place to keep up with failed payment subscriptions
  • Create user permissions that help us show/not show certain pages on our site
  • Use a company with renowned customer service*

*This, aside from PayPal, was probably one of the biggest reasons we wanted to switch from Gumroad. While the customer service wasn’t bad with Gumroad, it was very hit or miss. It also seems like Gumroad has come to a screeching halt with improving their platform, and that’s not a great sign when our revenue hinges on their product. 

the great paypal debacle of 2018: What the heck happened? 

What happened was we started the process of getting our PayPal account up, running, and added to Restrict Content Pro. While that process seemed straightforward enough, we ran into a few immediate problems: 

#1 PayPal makes stupid decisions

You used to be able to link a bank account to multiple PayPal accounts. I’ve done this for years. You can’t do this any longer. So my main business account that’s already linked to another active PayPal account, cannot be linked to our new Wandering Aimfully PayPal account. Two 1-hour long phone calls later (UGHH), and our PayPal account is now connected to a checking account we never use. Awesome.

#2 PayPal doesn’t support multiple IPNs

I won’t get too far in the weeds here, but the short explanation is that PayPal uses a thing called an “IPN” to fire data somewhere when a purchase happens. For us, we need the PayPal IPN to send data to Restrict Content Pro so a user can get added to our membership. But, we also wanted that same data to go from PayPal into our email provider (Drip). No dice. We had to choose one IPN bridge to rule them all, even after trying a workaround using Zapier that was supposed to have multiple IPNs work (that workaround left us confused and more angry). For now, we’re handling the PayPal to Drip process manually - as in clicking a button, applying a tag, and copying + pasting email info manually. It’s a bummer, but it’s only for a small amount of customers for now. 


First and foremost, we're running around the house singing the "PayPal sucks, it really really sucks!" song, which definitely helps. (Yes, really.) 

You might be asking yourself though, why aren't we singing the "Screw you PayPal!" song instead and just deciding to scrap PayPal altogether? Why go through all this effort? As we talked about in last week’s Build Diary video, we let the data make this decision for us. 

We can attribute over $200,000 in revenue, since 2015, directly to PayPal purchases. We have to offer PayPal. 🤣

For now, we’re overcoming this challenge with a lot of yelling and being willing to do some manual processes any time someone purchases a Wandering Aimfully membership. FWIW: 40% of our pre-order buyers thus far used PayPal. The numbers still don’t lie. 

By the way, did we mention pre-order purchases are open until May 9? Grab one of our first 30 membership spots!

How can we see this obstacle as an opportunity?

This obstacle was a great opportunity to sing the PayPal sucks song. Obviously. 

In all seriousness though, this was a great chance for us to learn patience and communication when we're up against a technical challenge that feels out of both of our depths. It tested us BIG TIME, but we both buckled down, sat next to each other, and tried to tag team the issue until we found a solution. That kind of united front is what we know we'll need when addressing these kind of issues in the future, so this obstacle was a great chance to give that a try.

While these challenges suck, we’re not letting them derail our progress (completely) 

Our progress has definitely been slowed by these challenges. Our deadlines have been pushed back. Our excitement for Wandering Aimfully has been tested. But… we knew this type of stuff would happen and we’re getting through it together (and with the support of you guys!).

Your emails, tweets, Instagram comments, etc, are really helpful in our times of PayPal-despair. Ha!

Also, having an awesome existing community at our side (BuyOurFuture peeps) is great for our morale. We see happy folks interacting with each other and building cool stuff. That inspires us to push through these challenges.

It hasn’t been all rainbows and sunshine for us as a couple during these challenges. We’ve felt the pressure. We’ve had disagreements. This comes with the territory when you’re working with a partner. We simply try to over-communicate how we’re feeling and what we need from one another. Sometimes we can’t provide exactly what the other person needs, but we do our best and continue to circle back to why we’re doing all this work in the first place. 

At the end of the day, we never doubt we're better together and we know we can overcome whatever challenges we face through this build together.

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