Our Mission

Proven Business System

To provide ACTIONABLE resources that empower business owners to achieve their idea of success!

Our job is to support overwhelmed small business owners. Those business owners have all the resources they need to have a successful business right now! They don't need some overpriced and overhyped shiny marketing strategy. All they need is a change of mindset. As a business owner, you have to have a passion just to show up, so let's stoke those flames, build some momentum, and throw extra fuel on the fire of success. Experiences like online training, interactive workshops, mastermind groups, and success principles consulting guide the OSG community to a proper mindset and business foundation to gain confidence and clarity.

Throughout their 40+ combined years in the industry, the OSG team knew that many people hoarded all of the information. We saw nice people fail because they didn’t have a foundation. Our impactful ideas and actionable are your keys to success if you are ready for success. Aaron and Kylene are Success Principles certified trainers and bring a wealth of mindset tools on top of their deep passion for building good business fundamentals. They no longer want people to struggle and flounder when they start a business, but instead, thrive, hit the ground running, and be good citizens in the markets they intend to enter.

Success is our Success

The values our community is guided by are Significance, Community, Knowledge, Motivation, and Solutions. We guide small businesses away from spending all their money buying shiny objects and all their time trying to figure out what to do. A foundation saves both time and money, even when it seems counterintuitive.

Your Success is our Success!

Meet the Team

Aaron Montgomery

Aaron Montgomery

"I support overwhelmed small business owners that have limited time by providing critical actionable resources like online training, interactive workshops, advisory, and action-oriented mastermind groups, and success principles consulting. After those businesses become part of the OSG community, they have confidence in their business, clarity about how to succeed and make more profit."

Aaron is the main instructor, Success Principles Certified and holds a certificate as a virtual facilitator. He is the president and CEO of OSG and is focused on supporting the business that call OSG home. Aaron has been in the garment decorating and personalization industry since 2000. Aaron speaks at industry trade shows and also writes articles for 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

Kylene Montgomery

Kylene is the teacher that small businesses need to achieve their idea of success.  She is a guide for those small business superheroes who are overwhelmed and don’t have enough time in their day. Check out the workshop - Unlock Your Potential

Kylene works to empower small business owners with knowledge and support of their production capabilities and proper mindset and health to be successful. Kylene pulls from her counseling background to offer various services to achieve this goal. From personalized sublimation gifts and apparel, DTG  wholesale services at Montco.Biz. Solopreneurs and busy Moms also improve their mental and physical health with Rise and Shine Yoga and Success Principles workshops. You can count on Kylene to support others with more smiles and joy through gratitude.

Todd Downing

Todd Downing

Todd is OSG's brand ambassador and worked with Aaron to develop and design what OSG is today. He uses the 5 Keys of Growing and Launching as a foundation in his business and worked on the original iteration of the training before it went to a module program. His main business is as a wholesale print provider - FatDadWholesale.com and you can also find him hosting the weekly How-To program called "Tuesday with Todd" at LiveOSG.com.

Todd 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, DTF, 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.