Five Years, Five Shifts: My Entrepreneurial Journey

by Ashley Cheung, Principal & Founder of VPG

January 2, 2026, marks the beginning of my sixth year helming Virtual Patent Gateway (VPG). Reaching this moment feels like standing on a precipice looking toward the summit—grateful for the climb, grounded by the lessons, and energized for the ascent ahead. Each year reshaped my mindset, skillset, and identity in ways I never anticipated.

Year 1 was the year of transformation: shifting from generalist to specialist. I left something familiar for uncertainty—only to face the global disruption of COVID three months later. As a recovering people-pleaser with a fear-based mindset, I said “yes” to work and individuals that didn’t align with my values because I believed I had to prove myself. Those early choices became necessary teachers, showing me the power of focus: diluted focus creates diluted results; concentrated focus amplifies impact.

Year 2 demanded humility and encouraged me to explore my true calling. Growing up as an immigrant daughter, I tied my worth to external validation and job security—reflecting the sacrifices my parents made when they immigrated and built a life from scratch. Reading Anna Yusim’s Fulfilled: How the Science of Spirituality Can Help You Live a Happier, More Meaningful Life helped me realize I had never allowed myself to explore what truly fulfilled me.

By the end of Year 2, I began sharing my experiences to help others stuck in “safety mode.” Every win and misstep reminded me that courageously pursuing our calling is a founder’s greatest asset.

Year 3 pushed me far beyond my comfort zone. I intentionally spent 30% of each day in discomfort, taking on challenges that stretched my skills and mindset. I launched the Virtual Water Cooler Chat podcast—my first real foray into public speaking. I wanted to grow as a conversationalist, highlight other professionals’ journeys, and connect with people I once believed were out of my league. One thing that distinguishes our podcasts is that I approach each guest personally, and not through other team members. This is my commitment to the platform and our community. Finding the right production support led me to collaborate with Caitlin Nelson, who has served as the producer. The current season, Season 3, will conclude with Episode 94, and this journey taught me resilience, consistency, and the value of community partnerships, such as with ADAPT.legal and ADAPT Voices. This year also reshaped my relationship with failure; I began to see it as falling, not failing, a mindset that allowed experimentation without fear of judgment.

Year 4 taught me I am not alone. I built a multigenerational team, launched FEMTECH LIVE Lounge, and embraced new technologies—thanks to my Gen Z teammates teaching me Meta AI, Claude.ai, and Riverside. Leading became less about working harder and more about collaboration, mentoring, and listening. I volunteered as a leader in a community that I once feared I didn’t have. The expansion of skills, perspectives, and experiences in this team taught me that the power of collective growth outweighs any individual effort. Remember, there’s no “I” in team!

Year 5 transformed my view of leadership. I shifted from asking, “How do I scale VPG?” to “How do we grow together?” Completing The Leadership Catalyst: Igniting Inspired Change helped me embrace self-stewardship and healthy boundaries. I invested in my team’s development through mentorship, skill-building, and open dialogue, while also strengthening my personal brand and launching IP Talk: Brand Insights. Supporting professionals at various stages of their professions and watching them step into their confidence reminded me that leadership is not about doing more—it’s about empowering more.

Now, Year 6 is about expansion and redefinition. I will explore my Ikigai (the reason for being) and help others find theirs through Urban Raccoons Creative Hub, a collaboration with intergenerational creatives to deliver meaningful, sustainable impact. Inspired by scrappy raccoons (in cartoon form!) and my earliest entrepreneurial idea, we will focus on intentional growth with a limited number of clients.

We will also continue to customize our on-demand courses and training platforms to customized audiences, with Continuing Legal Education (CLE) credit and training on Ex Parte Reexamination filings services.

The evolution continues—multifaceted, collaborative, and abundant. From solopreneur to community builder, I am learning to shift from fear to growth. Every step counts.

What lessons have you learned, and what are your aspirations for 2026 and beyond?