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Don't Be Beta, Get Some Wins with Chief Knucklehead Stephen Colon (Ep. 20) Thumbnail

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Aug 30, 2025 (UTC)

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In pursuing goals, getting caught up in the idea that achieving something big and grandiose is needed to succeed can be easy. However, the truth is that small wins can be just as powerful in helping accomplish larger goals. These small wins can give motivation, confidence, and momentum to keep pushing forward, progress, and overcome challenges. In this episode, Stephen Colon joins Brett Henderson for another conversation on leading innovative ways and overcoming obstacles to achieve financial stability. A marine veteran who successfully transitioned into the civilian world, Stephen talks about his professional and business endeavors, why he gave up on some of his businesses, and how he generates the momentum he needs to get a win and become the best version of himself. Stephen Colon is the Founder and Director of Business Development at Knucklehead Media Group. He is a strategic and innovative business and sales professional with expertise in business development, relationship building, and training and development to drive growth, streamline productivity, and maximize profit. As a successful business owner, Stephen has fine-tuned the ability to leverage risk analysis for a company and deliver lasting results that propel a business to the next level. Additionally, he possesses a military background that has given him sharp leadership tools to build and train exceptional teams who contribute to achieving key business objectives and goals. Enjoy! In This Episode 01:43 - Backstory of Stephen Colon 05:14 - What led Stephen to leave the military 07:03 - How Stephen spent his teenage years 14:05 - Stephen's professional and business endeavors 18:58 - Why Stephen's previous businesses failed 22:15 - How Stephen found private equity partners to work with 29:05 - Why Stephen gave up on his personal training business 30:39 - How Stephen generates the momentum he needs to get a win 36:48 - The drive Stephen has to be the best version of himself 40:33 - LinkedIn connections Stephen recommends Favorite Quotes 08:19 - "I wanted to lead teams, build teams, and build a business. I wanted to have an impact. That's what drew me to run my own business." - Stephen Colon 11:57 - "There's no better catalyst for most entrepreneurs than realizing that you don't fit that mold of being just told of what to do and sitting in a box." - Brett Henderson 15:59 - "Some people can learn from experiences in a job. In today's social media-oriented world, you can start a business, be a consultant, or do something you stand up for on your own to go and be effective. You can be effective wherever you are, whatever company you're at." - Stephen Colon 31:30 - "How do you generate the momentum necessary to get yourself a win? You have to start getting small wins, then those small wins accumulate over time, and you develop the inertia and the momentum to string together a few good weeks. And those few good weeks progress towards a much larger goal." - Stephen Colon 38:07 - "You can be a victim or a victor. You can point the finger at other people, or you can point the finger back at yourself and realize that you can do something about it." - Stephen Colon 38:24 - "If you decide to take the easy road out, you are essentially training your brain to find the way out instead of the way through or the way around something." - Stephen Colon Connect with Stephen Colon Stephen Colon on LinkedIn Knucklehead Media Group Connect with Brett Henderson: 310-491-7975 Swe90.com LinkedIn: Brett Henderson Strategic Wealth Endeavor Listen to The Veteran Entrepreneur Masterclass Podcast Apple Podcast Spotify Google Podcast