Description:
There’s a certain kind of builder who doesn’t follow a clear path… they discover it by walking it.
In this episode, we sit down with Silyana Bojilova, a serial entrepreneur and consultant whose journey spans survival, reinvention, and ultimately finding purpose through helping others build.
From growing up in Bulgaria and navigating major life disruptions early on… to moving abroad, struggling through years of uncertainty, and eventually returning home to rebuild from scratch, Silyana’s story is one of resilience in its purest form. Nothing was linear. Nothing was guaranteed. But each step… even the messy ones… stacked into something meaningful.
What makes this conversation stand out is how her path evolved. Through failed experiments, side projects, burnout, and unexpected wins, she didn’t chase a perfect plan… she followed curiosity. That mindset eventually led her into consulting, startups, and mentorship, where she now helps others move faster by sharing what she’s learned along the way.
At its core, this episode is about trusting yourself when the path isn’t clear… and building anyway.
Key Takeaways:
- Resilience isn’t built in success… it’s forged through uncertainty and pressure
- You don’t need a blueprint to build something meaningful
- Trying and rejecting paths is part of finding the right one
- Early “failures” often reveal what actually matters to you
- Growth accelerates when you stop doing everything alone
- The real breakthrough comes when you align work with what brings you joy
Silyana Bojilova
Throughout my whole life, I have been a very competitive and goal-focused person who strives to always be in the 1% and deliver outstanding results.
My high level of energy and enthusiastic nature allowed me to excel in different roles and build solid business relationships and expertise.
THE MEAT OF IT!
- Early Life and Forming Resilience
- Growing up in contrasting environments in Bulgaria
- Loss, displacement, and adapting to new identities
- Learning to navigate uncertainty early
- Building Resilience Through Adversity
- Moving to France alone and surviving with limited resources
- Financial pressure, independence, and self-discovery
- “Burn the boats” mentality and personal growth
- Returning Home and Finding Momentum
- The emotional turning point that led her back to Bulgaria
- Trusting intuition over external expectations
- Entering IT during the early outsourcing wave
- Discovering Strengths Through Experience
- Moving from support roles to analytical decision-making
- Learning what kind of work actually fits
- The value of trying and rejecting paths
- First Steps into Entrepreneurship
- Craft-based business experiments and early failures
- Lessons in product quality and customer experience
- Realizing the importance of support systems
- The Builder Mindset and Curiosity
- Following ideas without overplanning
- Letting opportunities shape direction
- Balancing work, life, and creative exploration
- Taking the Leap into Consulting
- Leaving stability during uncertain times (COVID)
- Rapid growth and early burnout
- Learning limits of doing everything alone
- Breakthrough Through the Hackathon
- Joining without a team or clear idea
- Building a team organically
- Winning by solving a real problem for real people
- Transition into Startups and Leadership Roles
- Moving into startup consulting and fractional leadership
- Building teams and operations across companies
- Expanding impact through mentorship and advisory
- Finding Purpose and Zone of Genius
- Asking: What brings me joy?
- Shifting toward mentorship and helping others grow
- Building a business aligned with purpose and impact
Check out these related Episodes:
- Episode 271: Jill Heinze – Why AI Governance Matters Before You Ship Anything to Real Users
- Episode 270: Michael Haynes – From Corporate Strategy to Practical B2B Go-To-Market Growth
- Episode 269: Tetiana Kobzar – Creating Products People Love to Use with Behavioral Design & Gamification
