The Reason

Proven Business System

To inspire proactive small business owners to cultivate an uncommon mindset through essential FUNdamentals to maximize fulfillment by achieving their goals.

Our job is to empower overwhelmed small business owners. We know 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 and actionable ideas are your keys to 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 - Co-Founder & CEO

"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 primary instructor, Success Principles Certified, and holds a certificate as a virtual facilitator from the Success Principles by New Your Times Bestselling author Jack Canfield. He is the co-founder and CEO of OSG and is focused on supporting the businesses that make OSG their community. Aaron has been in the garment decorating and personalization industry since 2000 and has been supporting small businesses for nearly 30 years. He provides small businesses with the support they need to create a business they love, not just another job that steals all of their time. Aaron is a speaker and also writes articles for magazines and is also the author of the business foundation book The FUNdamentals of Business Success. You can also find him co-hosting the industry’s oldest (over 500 episodes) and most listened-to Podcast – 2 Regular Guys.  He also hosts a weekly show called Small Business Saturdays.

Todd Downing

Kylene Montgomery - CHO (Chief Heart Officer)

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. She is in charge of the wellness pillar of OSG and is integral in the mindset pillar as well. 

Kylene empowers success-minded people to generate mind & body healing with yoga & mindset training to be successful. Kylene pulls from her counseling background to offer various services to achieve this goal. If you are feeling stuck, unfulfilled, or ready for more, let Kylene will unlock your potential. Contact her directly at Over the many years of her career as a counselor, she found so much joy in supporting others in their pursuit of finding joy and happiness, thus achieving their dreams. To elevate her tool belt she became a Success Principles Certified Teacher, a certified Yoga Instructor, and also certified in R.I.M. As a mother, wife, daughter, sister, friend, and business owner, she has found the Success Principles and the practice of Yoga to be truly life-changing. For more information on Yoga go to Rise and Shine Yoga. You can count on Kylene for more smiles and joy through gratitude so tune into her weekly program called ThankFul Thursdays.

Todd Downing

Todd Downing - Brand Ambassador

Todd 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 - and you can also find him hosting the weekly How-To program called "Tuesday with Todd".

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.