A Mentor-Led, Community Membership for People who want Confidence, Connection, Consistency, and Control in Managing their Money

YES! This is what I've been waiting for! Sign me up! >>>

Tell me if this sounds familiar:

You’ve worked all your life, and no matter what job changes you’ve taken on, you have never felt like you had “enough” money.

It seems to just… disappear.

There’s a lot of stress, maybe a lot of tears.

You argue about money problems, or just avoid the subject altogether.

The examples you’ve had from others around money just don’t work for you.

There is so much information out there about how to solve your problems, you get overwhelmed and end up doing nothing.

You question your decisions, or your partner’s decisions, and can’t seem to get on the same page with them.

Maybe you feel all alone in the financial battles you face.

It seems like you might always be in this situation–just enough, but no more.

You can’t see a lot of freedom down the road.

It’s a bit depressing, and you’re not sure where you can go for help.

Things are kind of bleak and uninspiring ... 

But what if it could be different?

What if it was like this?


You had a happier, more peaceful household, and you definitely get better sleep.

You’ve been able to create more leisure opportunities for yourself and more time for family and friends.

You feel the relief of less materialism in your life.

At the same time, you feel great about the things you do own!

You’re able to be more generous, and you feel in control.

You have the social support you need for making financial decisions, from great mentors and peers.

You feel more patient and at ease.

You know the next steps you need to take for an even better financial future for yourself and for your family.

And that all feels really, really good.

How did you get to that new, amazing space?  


You moved from Financial Isolation to Financial Connection.


You stopped trying to deal with your situation by yourself, and you went looking for a real solution.


You succeeded!!

You turned in your one-oared, leaky, rickety rowboat for a seat on a clean, solid, shipshape ferry.

There are other people here, headed towards the same destination as you, and the captain definitely knows how to get you there!

That’s what it is to move from financial isolation to financial connection.

It’s recognizing the power of two or three gathered together.

It's admitting that you may not have all the answers, but that the answers are out there!

And knowing where to turn for the help you need.

YES! I NEED this connection with people that can support me!

Hi, I'm Josiah Aston

shown here with my beautiful wife, Amber! I like to include Amber in my pictures, because 1) she works with me 2) she always brings out my happiest smile ๐Ÿ˜‰


I’m a piano-teacher-turned-financial coach ๐ŸŽนโžก๐Ÿ’ฐ๐ŸŽ– who loves to meet my clients where they’re at and help them make the next step forward, without judgment.

I personally know what can happen when we dive into adulthood without the financial skills we need to thrive.

We were hundreds of thousands of dollars in debt by the time I finally realized “This is not getting any better; in fact, it’s getting worse incredibly fast. And I don’t know what to do.”

I have two master's degrees, an administrative administration credential and two teaching credentials. This has been great for keeping me employed, but taught me nothing about how to take ownership of my financial life and become financially free.

That day I realized I didn’t know what to do, I also realized I couldn’t fix things alone. I needed help.

I used to look down on asking for help. It wasn’t that I didn’t like or appreciate other people; I just prided myself on my independence and lack of "need" for other people.

But all my independence had sure landed me in a tough spot, hadn’t it?

So, I made that move. I found a community of people who wanted what I wanted. I started listening to the right voices and making the necessary changes. My wife and I got on the same page, and we took our family out of financial isolation and into financial connection.

We made some hard decisions, established a budget, and set up some big dreams. We slowly but surely worked our way through the debt and made our way to living comfortably and happily within our means.

We didn’t do it alone, and we are so incredibly grateful for everyone who has helped us along the way.

That’s why we got certified as financial coaches, and why we're starting Checkpoint.

Here's what you can expect when you join Checkpoint:


โœ” Confidence

I only bring mentors and leaders into Checkpoint live monthly trainings who genuinely know how to handle money-related issues in real life and can be expert examples for you to follow.


โœ” Responsibility

This community encourages one another to follow through on the financial choices they know are right for them. If those choices seem unusual to the outside world of consumerism and comparison–they’re no problem here!


โœ” Relief

In Checkpoint, we don’t leave divine intervention at the door. I won’t hit you over the head with it, but anyone who wants to recognize and celebrate the real relief that comes when we lean into God’s grace is always welcome to do so :)


โœ” Practical Skills

Everyone’s circumstances are a little different. I will work with you personally to ensure that you’ll always be able to take action and benefit from each month’s theme.


โœ” Balance

Bad money problems can take over your life. In Checkpoint, you’ll find opportunities to put things back in balance–the time with your family and friends that you need, the generosity with which you want to live, and the habits that will sustain a well-lived life.


How Checkpoint Works


Every month will have a theme that is specifically designed to give you the breakthrough you need for a better financial present and future. 


We call these themes Checkpoints! 


When you encounter a Checkpoint, you have the opportunity to explore a new frontier–to go to the next level in your finances, your relationships, and your career.

Everything in the membership is organized to help you get through that Checkpoint and on to that next level. 


  • A Live Talk is held early in the month to introduce the theme and give you new and practical ideas for integrating it into your life, so you can face your finance-related challenges and opportunities with confidence and clarity. 


  • Then throughout the month, in a private Facebook community, we will have an open discussion so you can apply the theme from the class to your specific circumstances. 


  • I will respond to your questions and you will be able to share your perspective and stories with one another, so that everyone can make changes with the encouragement and support they need.


Here is our calendar for the next 12 months! Also a quick overview of the Facebook group. 

(The calendar is subject to change, but only if I get an even more amazing opportunity for you that just can’t wait ๐Ÿ“…)

Here's how you can join us today and take full ownership of your money and your life!

Monthly Option


  • 60 minutes LIVE: Quality, transformative teaching on that month's theme
  • 30 minutes LIVE Q&A: Ask anything you want
  • Anytime access to ALL recorded sessions!
  • Exceptional community of like-minded people
  • Direct responses to your questions
  • First dibs on bonuses throughout the year!
This is for me--Take me to checkout!

Best Value Annual Option

$159--Save 22%!

One Full Year For Only $13.25/mo

  • 60 minutes LIVE: Quality, transformative teaching on that month's theme
  • 30 minutes LIVE Q&A: Ask anything you want
  • Anytime access to ALL recorded sessions!
  • Exceptional community of like-minded people
  • Direct responses to your questions
  • First dibs on bonuses throughout the year!
  • BONUS 1: Additional "Community Choice" Small Group Session
  • BONUS 2: Money Habitudes game + individualized "Money personality" report
A full year sounds perfect. Take me to checkout!

P.S. Your investment to work with me 1-1 would be a minimum of $250/month, so this is an absolute STEAL of a deal!


A full Money Habitudes game and 100% individualized “money personality” report.

Fast and fun to finish online, this report will give you eye-opening insights into your financial habits and attitudes.

My clients love this report!!


Are you more inclined towards Giving, Planning, Status, Security, Carefree or Spontaneous styles?

Catch this bonus and find your style!

Here's what some of my clients have to say about financial coaching:

"I think the biggest thing for me [is] knowing where I want to go.


Before, I knew I wanted to get my money right, but why did I want to do that? 

Now I have plans in place. I know what I want to do in my life, who I want to help and I have a plan set up on how I'm going to get there."




"I'm in control of my money now.


It feels like I want to protect it.

I finally paid off all my credit cards; I don't want to use credit cards. 

I'm making informed decisions."




"Now we're in our own space, our own apartment, which is huge for us. 


We're still not perfect, we still have a lot of room for improvement.

But we were able to do it."

-Matt and Cynthia

Frequently Asked Questions:


"When are the LIVEs?"

Currently I have most classes planned for the first week of the month, on Thursday at 5PM PST. However, I do like to work with the community and if there is a better time for more people, we might make changes. 

Concerned about making it to the class? Not to worry! I’ll have all replays available to you in an online library :)

"Can I cancel anytime?"

I am completely confident that what Checkpoint has to offer will put you on the route you need to step into a better, happier version of yourself, your life, and your financial future.

However, if you decide that it's not what you need at any point, you can reach out to me at [email protected] and we’ll cancel your subscription, no questions asked! (And of course, you'll have full access to the library of replays and FB community until your subscription period ends.)


"Is there another option besides Facebook? not a FB fan..."

It makes sense if Facebook isn’t your thing! I will send you a special video that will show you how to use the group effectively to get the coaching and community support you need, even if you never use Facebook for anything else and/or want to avoid “the feed.”  It’s based on the advice of a top productivity coach who still uses Facebook to facilitate his personal productivity bootcamp, so it’s good stuff! ๐Ÿ‘

What if I have another question that isn't listed here?

Please reach out to me at [email protected], and I'd be happy to personally answer any questions you might have :)

I’ve created this group because many of you want better examples of financial success, access to a financial coach, and a community of other people who have good financial goals.

However, my normal coaching programs aren’t quite a fit for you, at least not right now.

This is my best offer for those circumstances

I promise I won't let you down

Our next meeting is Thursday, December 1st. I'd love to see you there!
Thanks, Josiah. I'm ready! What are the options again? >>>