Cut From the NBA, Built a Million-Dollar Coaching Empire

What does it take to turn 60 rejections into a nine-year pro basketball career and then build an entirely new business from scratch?

In this episode of From Underdog to Entrepreneur, Pat Miller sits down with Dre Baldwin, founder of Work On Your Game, a TEDx speaker, 43-time author, and former professional basketball player who spent nine years playing overseas. Dre shares how he went from a walk-on at a Division III college to building a company that helps entrepreneurs and experts install the mindset, systems, and strategy needed to scale from six to seven figures.

Dre opens up about cold-calling 60 basketball agents and mailing VHS tapes of his footage just to land his first pro contract and how he started posting training videos on YouTube back in 2005, years before "influencer" was even a word. That early audience-building experience taught him lessons about ownership, platforms, and personal branding that still guide his business today.

• Why being an underdog can actually be an execution advantage

• How relationships and "tap-rooting" knowing someone who knows the right person open doors in business

• The real difference between motivation and discipline, and why only one of them is repeatable

• Why building on rented platforms (social media) means you don't actually own your audience

• How relatability and authenticity build stronger connections than raw talent or fame

• Why slowly transitioning clients to other team members protects a business built around one person

• The importance of structure, self-discipline, and controlling distractions as your own boss

Dre Baldwin is the founder of Work On Your Game, a company that helps experts and entrepreneurs install the mindset, systems, and strategy needed to scale their businesses from six to seven figures. He's a TEDx speaker and a 43-time author. Before entrepreneurship, Dre spent nine years as a professional basketball player overseas, mostly in Europe, after walking on at the Division III college level. While still playing, he began posting training videos on YouTube back in 2005, building an audience that eventually extended beyond basketball players to professionals and entrepreneurs interested in his lessons on discipline, confidence, and mental toughness. In 2015, he stopped playing basketball to focus full-time on that mindset-driven business, moving through professional speaking before shifting into the consulting and coaching work he does today, centered on execution reliability and building presence and power in business.

LinkedIn: https://www.linkedin.com/in/dreallday/

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Subscribe to From Underdog to Entrepreneur: Building Dreams with Pat Miller for weekly conversations with entrepreneurs who share the real stories, lessons, failures, and successes behind building thriving businesses. If you're passionate about entrepreneurship, leadership, business growth, entertainment, and personal development, this podcast is designed to help you build your dream.

New episodes are released regularly.

Why Diversity Training Fails and What Actually Works

What happens when you've spent 30 years telling CEOs the truth nobody else will?

In this episode of From Underdog to Entrepreneur, Pat Miller sits down with Mauricio Velasquez, president of Diversity Training Group (DTG) and author of the newly released book Tackling Toxicity: A Skills-Based Guide to Addressing Toxicity. Mauricio has trained, consulted, and coached over a million people across every U.S. state but one in a career spanning three decades.

Mauricio opens up about starting his business on a houseboat in Baltimore's Inner Harbor, a $520-a-month setup with no insulation but a "billion-dollar view," and how growing up watching racism directed at his immigrant parents shaped his life's work. From there, he built a career doing the jobs nobody else wants to touch: sexual harassment training, executive coaching, and calling out toxic behavior that most companies would rather ignore.

• Why most people are conflict-averse and avoid addressing toxic behavior and why that silence only makes it worse

• The difference between responding and reacting when someone is being toxic or bullying

• Why "soft skills" are actually the hardest skills to master, and why the label undersells them

• How writing a book and speaking at conferences became a lead-generation engine for his consulting business

• Why diversity and inclusion work is tied directly to business growth, market expansion, and staying competitive

• Real, unfiltered stories from Mauricio's career from a car dealership salesman ignoring his wife, to a model home saleswoman questioning whether he could afford a house, to his own mother's initial rejection of his wife

• Why he believes DEI work is set for a resurgence, even amid current industry headwinds

Mauricio Velasquez is the President of Diversity Training Group (DTG), a company he founded that is celebrating 30 years in business this year. Over the course of his career, he has trained, consulted, and coached more than a million people in every U.S. state except North Dakota. His work covers diversity and inclusion training, sexual harassment training, mentoring, and executive coaching, helping organizations and leaders address issues they'd often rather avoid. Mauricio is also the author of the newly released book Tackling Toxicity: A Skills-Based Guide to Addressing Toxicity, which draws on real stories from his three-decade career to teach practical, skills-based approaches for calling out toxic behavior in the workplace and beyond. He got his start in business working out of a houseboat in Baltimore's Inner Harbor, and his motivation for the work traces back to witnessing discrimination directed at his immigrant parents as a child.

LinkedIn: https://www.linkedin.com/in/mauricio-velasquez-mba/

Website: https://www.diversitydtg.com/

Facebook: https://web.facebook.com/mauricio.velasquez.9484/reels/

Follow Pat Miller for more conversations with entrepreneurs who share the real stories behind building successful businesses.

Website: https://patmiller.net/

YouTube: https://www.youtube.com/@thepatmiller11

LinkedIn: https://www.linkedin.com/in/thepatmiller11/

Instagram: https://www.instagram.com/thepatmiller11/

Facebook: https://www.facebook.com/ThePatMiller11/

Subscribe to From Underdog to Entrepreneur: Building Dreams with Pat Miller for weekly conversations with entrepreneurs who share the real stories, lessons, failures, and successes behind building thriving businesses. If you're passionate about entrepreneurship, leadership, business growth, entertainment, and personal development, this podcast is designed to help you build your dream.

New episodes are released regularly.

What happens when you walk away from a 22-year career on Wall Street to pursue something completely different?

In this episode of From Underdog to Entrepreneur: Building Dreams with Pat Miller, host Pat Miller sits down with Amanda Anderson, founder of Ring and Run Dog Walkers, to explore her remarkable transition from the fast-paced world of New York's Financial District to building one of Staten Island's premier dog walking businesses.

Amanda shares how she recognized the changing landscape of Wall Street, started building her business while still employed, and eventually turned a side hustle into a thriving company. She explains why entrepreneurship isn't always about chasing millions, but about creating a lifestyle you genuinely enjoy.

Throughout the conversation, Amanda offers honest advice on hiring, setting boundaries, automating operations, building customer trust, and creating systems that allow a business to grow without consuming your entire life. Her story is a powerful reminder that success can look different for everyone.

Whether you're considering leaving a corporate career, building a service business, or looking for inspiration to pursue a more meaningful path, this episode delivers practical lessons from someone who successfully made the leap.

• Why Amanda left a 22-year Wall Street career to become an entrepreneur

• How to build a business while still working a full-time job

• The importance of running your side hustle before making the leap

• Why relationships and customer trust matter more than marketing

• How hiring the right people can transform your business

• The systems every growing business should implement early

• Why entrepreneurs need clear boundaries with clients

• The difference between working in your business and on your business

• How to create a business that supports your lifestyle instead of consuming it

• Why success isn't always measured by revenue alone

Amanda Anderson is the founder and owner of Ring and Run Dog Walkers, Staten Island's premier dog walking service. After spending more than two decades working on the trading floor in New York City's Financial District, Amanda made the bold decision to pursue entrepreneurship full-time.

Today, she has built a trusted pet care business known for exceptional customer service, strong client relationships, and personalized care. Amanda combines her passion for animals with a people-first approach, proving that businesses built on trust, reputation, and genuine service can thrive through referrals and organic growth.

Follow Amanda and Ring and Run Dog Walkers on social media to learn more about her entrepreneurial journey, pet care insights, and growing a service-based business with purpose.

Website - https://ringandrundogwalkers.com/

LinkedIn: https://www.linkedin.com/in/amanda-anderson-707a4512/

Facebook: https://www.facebook.com/RingandRunDogWalkers/

Instagram: https://www.instagram.com/ringandrundogwalkers/?hl=en

Follow Pat Miller for more conversations with entrepreneurs who share the real stories behind building successful businesses.

Website: https://patmiller.net/

YouTube: https://www.youtube.com/@thepatmiller11

LinkedIn: https://www.linkedin.com/in/thepatmiller11/

Instagram: https://www.instagram.com/thepatmiller11/

Facebook: https://www.facebook.com/ThePatMiller11/

Subscribe to From Underdog to Entrepreneur: Building Dreams with Pat Miller for weekly interviews with entrepreneurs, founders, and business leaders sharing the lessons, challenges, pivots, and wins that shaped their success.