OSG Squad
  • Access to Live Video Q&A

  • Email and Text Access to the Trainers

  • Private Members Only Facebook Group

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Monthly Membership

*Automatically Recurring Monthly Billing

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Annual Membership

*Automatically Recurring Yearly Plan 

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(Refunds will be prorated to monthly rate if less than 12 mo)

  • FREE Access to 5 Keys of Growing & Launching Training Program

  • Access to Past Trainings for the Life of your Membership 

  • Exclusive Private Member's Group and Dashboard full of Resources and Extras

  • Email Access to the Trainers

Business Training

Here is what some of the OSG Squad have to say about the OSG Community...

Todd's post are the first thing I look at when I get up at 5am and try to base my day off his motivation. This training has already made me feel more confident about what I am doing!

Worth every penny. Thanks guys! My spreadsheet is set up. Now I know how many items I NEED to sell per day. (It’s higher than my goal. Yikes). But at least now I know. Re-set and let’s go kick some 🍎’s.

It was wayyyyy more right from my vantage point for the launch than thought! I really appreciate what Aaron and Todd are doing, your availability & willingness to work with us to build so many great businesses.


No Judgement Zone

Todd and Aaron provide a safe and fun environment where you can learn, grow and feel success. No matter the size of your business or your current level of success we are here to help as best we can. You bring the hustle we will provide the knowledge.

100% Satisfaction Guarantee

We don't believe you will find a business support team that are willing to do more than Todd and Aaron. We are here for you and want to hear about your wins and failures. We know that as long as you are willing to do the work we are willing to do whatever we can to help you to your definition of success.


  • We are Listening!

    We listen to our members as their success is our success. We will be continuously polling and talking to the members to find out what they need for their business. If we don't have the information we will find someone that does. Look for special guest trainers from time to time and just be an active participant in the community. Check out our Business Basics group on Facebook to get involved.

  • Future Topics

    You can see what currently on scheduled for future live training at the Business Basics Events Page.

Meet the instructors!

Aaron Montgomery

Aaron has been in garment decorating and personalization industry since 2000. Aaron speaks at industry trade shows and also writes articles for the industry magazines. He is dedicated to helping small businesses grow and succeed. You can also find him co-hosting the industry’s oldest and most listened to Podcast – 2 Regular Guys. 

Todd Downing

Todd Downing is a self-made inspirational leader in the industry.  Starting with a simple vinyl decal business in 2007, his business has grown to include eco solvent printing, spangled transfers, and team sales.  He is also an online community mentor that strives to help others see how to move their businesses forward in a realistic fashion.

Want more? Join our exclusive Mastermind Group!

  • Structured Mastermind Program with a proven formula of success!

  • All of the Monthly Training Sessions

  • Access to Live Video Q&A

  • Email and Text Access to the Trainers

  • Bi-Weekly Group Video Calls

  • Direct Group Problem Solving

  • Group Challenges and Motivation

  • Peer Accountability

  • Private MOS Only Facebook Group

  • All Calls and Training Session Access