The Entrepreneur Health check

Notes from vYve sessions in Amsterdam and New York with nearly two dozen founders, and four lessons from inside the exam room.

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James Orsini

Oct 20, 2026 · 2 min read

By James Orsini

I’ve just come off two fabulous multi-day meetings with nearly 2 dozen different entrepreneurs and founders from around the world. Our vYve offering took us to Amersterdam and New York City for a few in person meet ups.

While we spent time exploring the land, meeting the locals and taking in the sights, the real work was done in smaller group classroom sessions. Together we developed anchor statements to tell our respective stories and reviewed our core business, what makes them unique, and we set some aspirational goals.

Our health check included:

Ø Our sign in History — business overview

Ø Anything hurt? — Issues upon us now

Ø Eating right- client status and financial forecast

Ø Enough exercise- new business pipe

Ø Blood pressure- nervous about economy or competition

Ø Heartbeat- business vision and contingency plans

My observations from inside the exam room:

1) Stick to what you are good at: Entrepreneurs feel compelled to do everything themselves. I heard multiple times “I’m not good at finance, I’m not good at marketing, I’m not good at operations”. Guess what, I’m not good at gardening and it’s why I hired a landscaper! Don’t be afraid to ask for help.

2) Just birth it: Many entrepreneurs are striving for perfection in the product or service before putting it into the market. It’s a small idea not an elephant, just birth it. Don’t squeeze the baby so tight that you choke it to death. Perfection is the death of innovation. You can make enhancements after launch.

3) Accept what you don’t know: It’s good to keep different company. Yes, become friends with someone who’s already launched a similar product or service; But also widen your circle to include people outside your space. These different perspectives can make your product or service better or richer. Iron sharpens Iron when it rubs up against one another.

4) Kindness, Gratitude, Empathy always wins: There will be no shortage of opinions from the peanut gallery I assure you. Some will genuinely have your best interest in mind and others not so much. Don’t get defensive. Smile and move on. Be a sponge and not a rock. Absorb what should be absorbed.

I’ve been advising entrepreneurs for the past decade. The vYve program helps them reach their greatest personal and business potential.

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James Orsini

stacklist.com/jamesorsini

A multi-hat operator with 40+ years across finance, advertising, and operations. Trained at KPMG and Goldman Sachs, then spent 11 years scaling VaynerX from $42M to nearly $350M in revenue alongside Gary Vaynerchuk.

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Summary

James Orsini shares insights from entrepreneur health check sessions conducted through the vYve program in Amsterdam and New York City, offering four key observations: focus on core strengths, launch imperfect products quickly, embrace diverse perspectives, and lead with kindness and empathy. The health check framework evaluates business fundamentals including sign-in history, current issues, financial status, new business pipeline, competitive concerns, and vision planning.

Tags

entrepreneurship · business-health · startup-advice · mentorship · leadership · personal-development · vyve

Key entities

James Orsini (person, 0.95) · vYve (organization, 0.9) · Amsterdam (location, 0.95) · New York City (location, 0.95) · entrepreneur health check (concept, 0.85) · business perfection (concept, 0.8)

Classification

analysis · language en · status final

Provenance

claude-haiku-4-5 via @stacklist/be@0.1.0, confidence 0.85, 20 Oct 2026