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Why Struggling at Annapolis Doesn't Define Your Future Success
Struggling academically at the Naval Academy? You're not alone, and this episode proves that your worth isn't defined by your class rank. Stefan Simkovic, Class of 2009, graduated in the "Comma Club" – the very bottom of his class – yet went on to build a thriving international business that's now working with billion-dollar companies.

As we approach the 12-week exam period when academic stress peaks, this conversation offers hope and perspective for any midshipman facing academic challenges. Stefan's story demonstrates that the grit and resilience you develop at Annapolis – even while struggling – becomes the foundation for future success.
What You'll Learn About Academic Struggles at the Academy
- How failing chemistry plebe year started a cascade of academic anxiety and self-doubt
- The reality of living with constant uncertainty about graduation
- Why some midshipmen need more "soak time" to absorb material than others
- How comparing yourself to high-achieving classmates can rob you of confidence
- The importance of utilizing Extra Instruction (EI) and building relationships with professors

Key Takeaways for Struggling Midshipmen and Parents
- Academic rank doesn't determine your future potential or leadership ability
The Naval Academy network becomes invaluable throughout your career
- Pressure and adversity at Annapolis build resilience for entrepreneurial success
- Learning to listen to subject matter experts is a crucial leadership skill
- Staying present and responding with logic rather than emotion during difficult times
- Essential Questions for Parents
- When your midshipman calls home struggling academically, consider asking: Have you attended Extra Instruction? Are you getting adequate sleep? - What other factors might be affecting you

The Vermeer Group is a residential real company matching military families with trusted real estate teams across the country. If you have any real estate questions at all, please text Grant at (650) 282-1964 or email [email protected]

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The mission of Academy Insider is to guide, serve, and support Midshipmen, future Midshipmen, and their families.
Grant Vermeer your host is the person who started it all. He is the founder of Academy Insider and the host of The Academy Insider podcast. He was a recruited athlete which brought him to Annapolis where he was a four year member of the varsity basketball team. He was a cyber operations major and commissioned into the Cryptologic Warfare Community. He was stationed at Fort Meade and supported the Subsurface Direct Support mission.

He separated from the Navy in 2023 and now owns The Vermeer Group, a residential real estate company that matches service academy families with trusted real estate teams all across the country. Text (650) 282-1964 with any real estate questions.

We are here to be your guide through the USNA experience.

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