The Reason


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

Our job is to help you fall even deeper in love with your business by building a foundation based on the FUNdamentals. We were tired of watching so many small businesses around us struggle. We knew they were seeking answers in the shiny objects and 10X gurus because we used to be there. Then we realized that none of that worked until you build a solid foundation. The roots of your money tree so to speak. We set out to fulfill our mission of creating business owners who are in love with their business.

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 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!

Ideal Partners - Who We Work Best With

At Our Success Group, we don’t have clients; we have partners. Our mission is to work hand-in-hand with you to maximize your fulfillment and achieve YOUR goals. When you're ready to take the next step, you can even become a facilitator or coach within our community. We’re seeking partners who embody these four essential criteria.

Solution-Oriented Learners: You actively seek solutions, embrace continuous learning, and implement new strategies.
Your Challenge: You’re overwhelmed with information and need clear, actionable insights to focus on what truly works for your business.

Growth-Minded Investors: Entrepreneurs who are willing to invest in themselves and their businesses. You see expenses as investments in your future.
Your Challenge: You’re bombarded with investment options and need guidance on where to allocate resources for the best ROI.

Accountable Action-Takers: You take ownership of your actions, seek accountability, and commit to following through on your plans.
Your Challenge: You sometimes struggle with motivation or direction and need a supportive framework to stay on track.

Community Builders: You value building relationships within your professional network and creating a supportive community.
Your Challenge: You can feel isolated and need a network of like-minded individuals to share experiences and advice.

Why This Matters - Understanding these criteria helps us ensure that our partnership will be mutually beneficial. By aligning with these qualities, you’ll not only find the support you need but also contribute to a thriving community of like-minded business owners. How many of these are you? If these descriptions resonate with you, we’d love to explore how we can work together.

Schedule Your Free Partnership Review

Meet the Team

Aaron Montgomery

Aaron Montgomery - Co-Founder & CEO

Director of Impact

"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 550 episodes) and most listened-to Podcast – 2 Regular Guys.  He also hosted a weekly show called Small Business Saturdays. Now you can find him weekly on OSG Live with Kylene and the rest of the Fab 4.

Todd Downing

Kylene Montgomery - CHO (Chief Heart Officer)

Director of Wellness

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 lack time in their day. She is in charge of the wellness pillar of OSG and is integral in the mindset pillar as well. After people interact with Kylene, they experience more joy, smiles, and fulfillment in their lives.

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. With over 15 years of counseling experience and as a Success Principles Certified Teacher, Essentials RIM (Regenerating Images in Memory) Certified Counselor, CYT 200hr Yoga Teacher and Crunchi Advocate, she has access to a variety of tools to best support people on their journey to unlock their true potential to live a life of vibrancy. If you are feeling stuck, unfulfilled, or ready for more, Kylene will unlock your potential. Contact her directly at ContactKylene.com. As a mother, wife, daughter, sister, friend, and business owner, she has found the Success Principles and Yoga to be life-changing. For more information on Yoga go to Rise and Shine Yoga. Find Kylene and the rest of the Fab 4 weekly on OSG Live. You can count on Kylene for more smiles and joy through gratitude.

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 - FatDadWholesale.com 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.