017 – [Deep Dive] Evaluating Software

This is a deep dive episode of the Tech of Business podcast! Today we’re showcasing a couple of key tech decisions I’ve made with my clients recently. The goal of today’s episode is to understand a bit more the role of software decisions in business.

Last week, Sam and I were in Las Vegas on vacation since our girls were away at summer camp. While we were there, I went live on Facebook once from the pool deck… and this livestream was titled “Tech itself isn’t sexy… but what you can do with a great tech stack is…”

And we’re continuing that conversation right now…

In general, I’m tool agnostic… I’ll work with just about any software service that has come across my desk even if I believe that there is a better option out there.

Everything that tech can do for businesses (and hobbyists and non-profits) is incredible…

In isolation the tech itself is just not fun to explore and implement. It’s a chore and something that most folks would rather outsource and say “Just tell me the best option for xyz…”

That’s really what I mean by tech being so “un-sexy.”

When I come to you with the exact right piece of technology for the next phase of your business, the idea of new technology is sure to evoke some aspirations and optimism. And a second later, for most businesses, there is also a distinct dread or lack of emotion which comes from knowing that there will be a learning curve, immediate outflow of cash and likely integration issues when it comes to fully bringing this new tool into the fold.

And, whether you’re a solo entrepreneur, have a small team, run an agency or are getting ready to franchise your operations… similar issues creep in.

This is a time where I don’t believe the 80-20 rule applies. There is a distinct advantage to fully implementing the new tech rather than getting minimum viable functionality out of it. Because the sexy part comes in the last 20%.

Let’s dig into a couple of recent clients of mine and how we made tech decisions that are right for their business now and to carry the required amount of weight into the next chapter of your business.

Both the client stories are revolving around taking payments – because we all like to make it easy for our clients and customers to buy from us.

My client Jen has a thriving Thinkific site. She has dozens of courses on the platform, is offering completion and continuing education certificates on some of the courses and has recently brought on additional instructors. She also has some of the courses available for affiliate promotions.

Initially, the built-in payment system on Thinkific was all she needed. But as she built out the school, she felt that her needs may have outgrown the system and we began to look at additional payment portals and mechanisms for managing the greatest needs.

Let’s break it down.

  • Jen’s students need to be able to purchase her courses
  • Jen needs to pay her instructors when each of their courses is purchased. This will be at one of two rates, depending on if the student purchased through the instructor link or not.
  • Jen needs to identify affiliate-initiated transactions since compensation agreements are in place with influential parties in her industry.
  • Jen needs to have split pay and recurring payment options available and where the student can manage their credit card on file
  • Jen needs this to be easy since she doesn’t have a full-time accounting department

Both Jen and I are familiar with ThriveCart which looked like a great option for providing the functionality that Jen was seeking…

And I go crazy for setting up integrations and finding the best right solution, selfishly I wanted ThriveCart to be the right solution for Jen because it would mean a ton of the work that I love to do.

But we cannot jump into tech blindly, so we weighed the benefits and drawbacks of the built in Thinkific payment system against ThriveCart with the specific lens on ease of use for Jen and her team.

Feature ThriveCart Thinkific
User account creation After payment, using Zapier Prior to checkout
Course enrollment After payment, using Zapier Immediately after checkout
Instructor payment tracking and payouts Tracking via Google Sheets, manual payment Built in tracking, manual payment
Affiliate tracking and payouts Built in functionality Manual payment, built in tracking
Split Pay & Recurring pay Built in functionality Built in functionality for Stripe transactions
Self Serve Credit Card management Built in functionality Built in functionality
Affiliate links Can link anywhere Must link to a course or bundle
Affiliate assets Built in functionality Links only


I really wanted ThriveCart to be the right solution for her, because I imagined so many other things we could do – including upsells, downsells and add-ons. But when we put our heads to the problem that we were solving, the answer became apparent that using the built in Thinkific solution was a better option for selling the vast majority of her Thinkific courses.

ThriveCart sounds sexy… it’s a great interface and creates an enjoyable payment experience but in truth it’s simply a mechanism for taking payments and managing affiliates. And when we looked at it, what we really needed was something that did that job without a lot of overhead for Jen and her team.

Had we implemented ThriveCart fully, more work would be required for every new course, every new affiliate and every new instructor.

So, we put ThriveCart on the shelf. And it’s a huge weight lifted off both of our shoulders. The upsides of ThriveCart do not outweigh the costs of implementing and maintaining it for Jen’s core business.

In Jen’s case, the rationale for looking at ThriveCart was a bit of shiny object and possibly FOMO but as you’ll see with the next client story, the simple and straightforward payment processing inside Thinkific is no necessarily enough to fulfill the requirements.

This next client is Stephanie. She and her company are in Canada and need to charge tax on top of course prices. We wanted to find a sexy solution that included a magic button to charge the exact right amount of tax and track it seamlessly. But there isn’t a magic button and the solution was totally not sexy – we cobbled together a solution that would help their team sell their courses and report tax right, every single time.

The solution we came up with is to use Thinkific for course delivery with Zapier for student enrollment. Student purchases are done directly on their WordPress website using a custom plugin that I wrote. This plugin uses Stripe for payment processing and overlays Taxamo for tax calculation. And the Taxamo transaction became the Zapier trigger to enroll the student.

Here is a diagram of the components and how they work together:

It’s a lot of moving parts and while each component has a specific job, and this is what I mean when I say that tech isn’t sexy. Nobody likes to run or support a many step process unless there is no alternative.

Just as with Jen, Stephanie and I didn’t come to this solution lightly. We evaluated Taxamo against other tax-charging tools and determined that for her needs, Taxamo was best.

At the outset both Stephanie and I knew that we would be able to create a solution that would meet the goals and provide the desired purchase and enrollment experience.

I had hoped it would take fewer hops across the web and far fewer hours to setup, but when we flipped the virtual switch and started processing live customer transactions, there was nothing better!

There are a large number of software solutions that can work to help you with compliance, streamlining and automation. The key point that I hope you take away from today’s conversation is to clearly identify why you are looking to add a new piece of software to your tech stack and also understand how to determine if it is the next right choice for you and your business goals.


Are you looking at bringing in a new software or tool to your business?

I invite you to book a tech strategy session with me. It’s at https://techofbusiness.com/strategy-session/ Together we’ll be able to determine how, when and if to add to your tech stack.

Comment below and let me know if you’d like more episodes like this one, what tech decisions you’re making and how I can help your business grow through software and technology.

Leave a Comment

Your email address will not be published. Required fields are marked *

Pin It on Pinterest

Share This