Entrepreneur Investor Author Philanthropist Advisor

Empowering Leaders to Build the Future of Business and Community

As Founder of Prevail Group, Reggie advises and invests in visionary businesses redefining their industries and communities. In partnership with Singularity, he helps global brands and family offices navigate the future with strategy, innovation, and purpose.

GROWTH • INNOVATION • INVESTMENT • COMMUNITY • GROWTH • INNOVATION • INVESTMENT • COMMUNITY • GROWTH • INNOVATION • INVESTMENT • COMMUNITY • GROWTH • INNOVATION • INVESTMENT • COMMUNITY •

Entrepreneur Investor Author Philanthropist Advisor

Empowering Leaders to Build the Future of Business and Community

As Founder of Prevail Group, Reggie advises and invests in visionary businesses redefining their industries and communities. In partnership with Singularity, he helps global brands and family offices navigate the future with strategy, innovation, and purpose.

BUSINESS DEVELOPMENT • PROJECT MANAGEMENT • PREVAIL FOUNDATION • BUSINESS DEVELOPMENT • PROJECT MANAGEMENT • PREVAIL FOUNDATION • BUSINESS DEVELOPMENT • PROJECT MANAGEMENT • PREVAIL FOUNDATION • BUSINESS DEVELOPMENT • PROJECT MANAGEMENT • PREVAIL FOUNDATION •

About Reggie Prevail

Building Businesses. Creating Impact. Inspiring Growth.

What’s up — I’m Reggie Prevail, a Virginia native born in Norfolk, VA.


I’m the Founder of Prevail Group, where I lead business transformation, culture building, and growth strategy through sales and smart technology implementation. I invest in companies through Prevail Ventures, focusing on businesses across the 757 while also backing select opportunities internationally. And I invest in people through the Prevail Foundation, supporting youth, community programs, and pathways that elevate the next generation.

Every project I take on — whether in business or philanthropy — is driven by one simple belief: we all have the power to prevail.

Book Sneak Peek

How to lose: shifting the mindset, redefining the meaning of loss

“How to Lose” by Reggie Prevail is not your typical success book. Instead of teaching you how to win, it reshapes the entire conversation by showing why losing, letting go, failing forward, and releasing what doesn’t serve you is the most powerful path to growth. It’s bold, counterintuitive, and refreshingly honest.


This book challenges the traditional “win at all costs” mindset and introduces a new way of thinking, you win because you learn how to lose. With sharp insights and a clean, no fluff style, Reggie gives readers a mindset shift that feels both freeing and motivating. If you’re ready for a perspective that disrupts the norm, this book is your starting point

How I Help Leaders and Businesses Prevail

Strategic Guidance. Meaningful Investment. Lasting Impact.

Advisory & Investment

Partnering with founders and executives to develop growth strategies, attract investors, and scale their businesses with purpose.

Speaking Engagements

Inspiring audiences with insights on leadership, innovation, entrepreneurship, and community impact.

Growth COnsulting

Guiding entrepreneurs from concept to execution through strategic planning, project management, and mentorship.

Philanthropic Initiatives

Collaborating with organizations and community leaders to create programs that drive sustainable change.

TESTIMONIALS

What people are saying

“Reggie has a rare ability to see both vision and execution. His guidance helped our startup secure funding and build a solid foundation for growth.”

— Marcus T., Founder, Elevate Tech Solutions

“Working with Reggie changed the way I approach leadership. His insight and mentorship brought clarity to both my business and personal goals.”

— Tanya R., CEO, Urban Legacy Group

INSIGHTS

Ideas to Help You Prevail

July 30, 2024
Starting and managing a business is challenging. You have to handle various responsibilities such as dealing with pe ople, managing clients, solving problems, and much more. One of the toughest parts is persevering when things go wrong. This is where resilience comes in. Learning to be resilient is key to becoming a successful entrepreneur. Here are some ways to build resilience: Here are the key features of a person with a growth mindset: 1. Practice Self-Care This might sound odd, but it's true. You need a clear mind to be resilient—one that isn't overwhelmed by emotions and thoughts. Achieving this requires taking care of both your mind and body. Mindfulness and Meditation: Practice mindfulness and meditation to clear your mind and stay focused. Exercise: Find a few minutes each day to exercise. Physical activity can greatly improve your mental well-being. Healthy Eating: Make sure to eat well to maintain your physical health, which in turn supports your mental resilience. 2. Have a Positive Outlook Focus on Solutions: Instead of dwelling on problems, concentrate on finding solutions. This proactive approach can help you see challenges as opportunities for growth. Celebrate Small Wins: Acknowledge and celebrate your achievements, no matter how small. This can boost your morale and remind you of the progress you're making. Surround Yourself with Positivity: Spend time with positive and supportive people who uplift you. Their optimism can be contagious and help you maintain a positive attitude. Practice Gratitude: Regularly take time to reflect on what you're grateful for. This can shift your focus from what's going wrong to what's going right, enhancing your overall outlook. 3. Seek Advise Reach out to people close to you or those you know to be positive and resilient. If you don't know anyone in your immediate circle, learn about how successful people have overcome challenges. Their stories can provide valuable insights and inspiration. For instance, consider the story of Steve Jobs. In 1985, Jobs was fired from Apple, the company he co-founded. This could have been a devastating blow to his career, but Jobs didn't let it define him. Instead, he founded NeXT, a computer platform development company, and acquired the animation studio Pixar. Both ventures were successful, and in a twist of fate, Apple acquired NeXT in 1997, bringing Jobs back to the company. His return marked the beginning of a series of revolutionary products like the iMac, iPod, iPhone, and iPad, solidifying Apple's place as one of the most valuable companies in the world. Building resilience takes time and effort, but it's a crucial skill for any entrepreneur. By practicing self-care, maintaining a positive outlook, and seeking support, you can develop the resilience needed to navigate the ups and downs of entrepreneurship. 
July 4, 2024
Leading a remote team based in the Philippines, I’ve witnessed firsthand how essential a growth mindset is for ensuring team success and cohesion. Here, I’ll share strategies that have worked for my team and can help yours thrive as well. Promote Open Communication Create an environment where constructive criticism is welcomed and valued. I make it clear to my team that feedback is a two-way street—I give them feedback, and I expect them to provide feedback to me as well. I find that video meetings are the best medium for these types of conversations, as chatting can often lead to miscommunication. Create a Collaborative Environment Encourage Input and Suggestions. When assigning tasks, I always ask my team if they have any suggestions or ideas to make the task easier. This not only fosters collaboration but also shows that I value their insights and contributions. Lead by Example As a leader, it’s important to demonstrate a growth mindset through your actions. Show your willingness to learn, adapt, and take on new challenges. One effective way to do this is by tackling tasks on video with your team, allowing them to see how you navigate through challenges and find solutions. Celebrate Effort and Progress I always remind my team that without everyone’s effort, our business wouldn’t thrive. They are an essential part of the puzzle. I let them know that I see and recognize all all the work they put in. Developing a growth mindset in a remote team requires intentional effort and a supportive environment. It can be challenging due to the nature of online communication and potential cultural differences, especially with an international team. However, the rewards of a motivated, resilient, and growth-oriented team are well worth the effort. 
July 4, 2024
Networking is a crucial component of career growth. Building and maintaining professional relationships can open doors to new opportunities, provide valuable insights, and enhance your professional reputation. I have been lucky to have met and interacted with people from all over the world from different backgrounds and industries. Here are some tips for building your professional netowrk: 1. Attend Industry Events Attend industry conferences, seminars, and workshops to meet professionals in your field. This can be online or offline but I personally feel like I can make better connections in the real world. don't be shy. Introduce yourself, exchange business cards, learn more about their professional background and business. And most importantly have fun and be genuinely interseted. They will feel if your just after their business card. 2. Utilize Social Media As I stated above, you can network online too. One of the best social platforms for professionals in LinkedIn. You can comment when someone posts a question that is realted to the industry you're in. you can also join linkedin groups and engage with its members. you can also post quality content where you can interact with people that engage with the post. There are other platforms aside from Linkedin, use them and network! 3. Join Professional Organizations Look for local, national, and even internationl associations that are related o your field. You can even volunteer for committees or leadership roles within these organizations to increase your visibility and build deeper connections. 4. Just Ask Request a short conversation with professionals you admire to learn more about their career paths and gain insights. Just please don't waste their time by not preparing. Prepare thoughtful questions to make the most of these conversations and again, show genuine interest. Not all will agree to meet with you. Networking is an essential element of career growth, offering opportunities, support, and knowledge that can propel you forward. By actively building you can create a robust support system that not only aids in your career advancement but also enriches your personal and professional life.

Win or Win.

A mindset. A movement. A way to prevail.

WORK WITH REGGIE

Ready to Prevail in Every Area of Your Life and Business?

Let’s work together to turn your vision into action.

How I Help Leaders and Businesses Prevail

Strategic Guidance. Meaningful Investment. Lasting Impact.

Advisory & Investment

Partnering with founders and executives to develop growth strategies, attract investors, and scale their businesses with purpose.

Speaking Engagements

Inspiring audiences with insights on leadership, innovation, entrepreneurship, and community impact.

Small Business Development

Guiding entrepreneurs from concept to execution through strategic planning, project management, and mentorship.

Philanthropic Initiatives

Collaborating with organizations and community leaders to create programs that drive sustainable change.