Read Time: 7 minutes

Jason Sherman, Founder and CEO of Vengo AI and author of The AI Gold Guide, is a multifaceted entrepreneur with a knack for innovation. From creating successful tech startups to producing award-winning films, his career is marked by a dedication to solving problems in creative ways. In this interview, Jason shares how his early experiences sparked a passion for entrepreneurship and how Vengo AI is addressing the challenges businesses face in customer service automation. With a focus on innovation, customer engagement, and intelligent automation, his insights are invaluable for entrepreneurs navigating the complexities of today’s digital landscape. Dive into this conversation to learn how Jason combines technology and strategy to build impactful businesses.

It’s a pleasure to have this conversation with you, Jason. To kick things off, I’d love to hear more about your entrepreneurial journey and what inspired you to start your business.

My entrepreneurial journey started when I was six years old, programming a colorful hot air balloon on a Commodore 64 for my teacher’s birthday. Seeing her reaction sparked my love for innovation. At 12, I sold products I brought back from Europe and wrote my own superhero comic book, which I sold to classmates. These early experiences taught me the value of creativity and initiative.

During the dot-com boom, I started a technology consulting company and later sold a successful brick-and-mortar franchise. Over the years, I’ve built companies from the ground up, produced award-winning films, and helped startups tell their stories through video and media. My journey has always been about solving problems, creating value, and helping others succeed.

Vengo AI fills a huge gap in the market with its B2B AI agent platform, designed to automate customer service and sales processes for businesses. The idea came from seeing how companies struggle to provide efficient and scalable customer support. By combining cutting-edge AI with a user-friendly approach, we’re helping businesses save time, reduce costs, and improve customer satisfaction.

What were some of the biggest challenges you faced when launching your business, and how did you overcome them?

One of the biggest challenges was educating business owners on what an AI agent really is—a more sophisticated and smarter version of a chatbot combined with powerful automations. Many were unfamiliar with how it could help them generate more leads and close deals faster. To overcome this, we focused on clear, simple explanations and real-world examples to show its impact. We also provided demos and case studies to build trust and demonstrate how it could save them time and money while improving customer engagement.

How has your personal background and experiences influenced your approach to entrepreneurship?

Growing up, I was always curious about how things worked, whether it was taking apart electronics or experimenting with computers. Traveling the world taught me how to adapt to different cultures, think creatively, and find opportunities in unexpected places. My experience as a violinist taught me discipline and patience, while my time in journalism and filmmaking showed me how to tell compelling stories that connect with people. Whether I’m building a product or pitching an idea, I lean on these life lessons to stay creative, resilient, and focused on solving problems in ways that genuinely help others.

It’s amazing how your experiences have shaped the way you approach entrepreneurship. How do those lessons translate into the core values that drive your business, and how do you make sure they show up in your day-to-day operations?

Innovation, simplicity, and customer success. We believe in creating cutting-edge solutions that are easy to use and deliver real, measurable results for businesses. To ensure these values are reflected in our operations, we prioritize listening to customer feedback, continuously improving our platform, and providing personalized support. Every decision we make, from product updates to onboarding processes, is guided by our mission to help businesses save time, increase efficiency, and close deals faster through intelligent automation.

How do you stay innovative and adapt to changes in your industry?

I stay innovative by constantly learning and exploring new technologies. I make it a habit to follow industry trends, attend webinars, and connect with other entrepreneurs to exchange ideas. Feedback from customers also plays a big role in shaping our product updates and new features. Experimenting with different approaches and not being afraid to pivot when necessary helps us stay ahead. Staying adaptable means being open to change and always looking for ways to improve our offerings to meet evolving needs.

What qualities do you look for when building your team, and how do you foster a positive company culture?

I look for people who are passionate, adaptable, and solution-oriented. Skills are important, but I prioritize individuals who bring a positive attitude and a willingness to collaborate. To foster a positive company culture, I focus on open communication, mutual respect, and celebrating wins, no matter how small. We encourage creativity, provide opportunities for growth, and create an environment where everyone feels valued. By ensuring everyone understands and aligns with our mission, we build a team that’s motivated to succeed together.

Building a strong, motivated team is essential for success, and fostering a positive culture plays a big role in that. With teams increasingly working remotely or in hybrid setups, how do you ensure effective communication and keep everyone aligned?

We use platforms like Slack and Google Meets for regular check-ins, meetings, and updates. Transparency is key, so we set clear expectations and document everything in shared spaces like Google Drive. We also encourage open dialogue, where team members feel comfortable asking questions or sharing ideas. Regular one-on-ones and team-building activities help maintain connection and ensure everyone stays aligned, no matter where they’re working from.

Thank you, Jason, for sharing your journey and insights on innovation, entrepreneurship, and building a successful AI-driven business. Your experiences and strategies offer valuable lessons for anyone looking to grow and adapt in today’s fast-changing world. We appreciate your time and look forward to seeing how Vengo AI continues to evolve!

Stay tuned for Part 2, where we dive even deeper into Jason’s approach to leadership, scaling a business, and the future of AI in entrepreneurship—coming next week!

Marc J. Bernstein JD, ChFC®, CLU®, CAP®

Financial Planner and Consultant, Bestselling Author, and Creator of the Forward Focus Forums

Marc helps high performing entrepreneurs and business owners create a vision for the future, accomplish their business and personal goals, financial and otherwise, and assists them in following through on their intentions.  Marc recently co-founded March, a forward-looking company with a unique approach to wealth management.  He captured his philosophy in his #1 Amazon Bestseller, The Fiscal Therapy Solution 1.0.  Marc is also the founder of the Forward Focus Forum, a suite of resources tailored specifically to educate and connect high performing entrepreneurs, and to help them realize their vision of true financial independence. The forum includes;

• the Founders’ Forward Focus Forum: a series of articles focused on entrepreneurship
• the Founders’ Forum Radio Show and Podcast: featuring interviews with some of the area’s top founders and their experiences in business
• the Manufacturers’ Forward Focus Forum: a specialized resource group for owners/founders of manufacturing companies, including a private Facebook group; a private discussion group for high performing leaders of manufacturing companies to share resources, news, network with each other, and collaborate