Ola Gipsh
.jpg)
Build Confidence. Take action. Lead without fear.
Strategic coaching for first-time entrepreneurs and emerging leaders who refuse to choose between success and sanity.
I combine real-world business experience (3 companies, $5M scaled) with CBT-certified mindset coaching to help you navigate fear, overcome imposter syndrome, and build sustainable success - one clear action at a time.
.jpg)
A Business Coach Who's Actually Built the Businesses
I'm not the kind of coach who teaches from a textbook. By 25, I launched my first company. By 30, I had built three companies across two industries, scaling one to $5M+ and 30 employees. I've navigated mergers, acquisitions, international expansion, burnout, and imposter syndrome and come out the other side stronger.
Here's what makes me different:
I combine real-world entrepreneurship with CBT-certified mindset coaching. I've lived in multiple countries, led multicultural teams, and pioneered remote-first businesses before it was mainstream. I have a background in sociology and a love for data (yes, I genuinely enjoy Excel).
But more importantly, I've failed. I've burned out. I've felt like a fraud even while leading a multi-million dollar company. And I've learned how to build resilience, overcome fear, and create sustainable success.
My mission is simple: I help ambitious professionals build businesses and careers that fuel their lives, not consume them.
I ask uncomfortable questions. I serve as your second brain. I focus on long-term sustainability over quick fixes. And I hold you accountable to turn insights into action because confidence comes from doing, not just thinking.
My approach combines:
-
Strategic business guidance (3 companies, $5M scaled, international experience)
-
Mindset mastery (CBT-certified, specialized in overcoming fear and imposter syndrome)
-
Resilience building (I teach you how to learn from failure, not just avoid it)
-
Sustainable growth (long-term success, not burnout culture)
-
Accountability framework (you WILL achieve your milestones)
Ready to build something that lasts?
My expertise
With a decade of leadership roles, I combine analytical precision with strong people skills. Here’s what I bring to the table:
-
Leadership & Team Management – Proven success in leading and growing international teams, from small startups to 30+ employees.
-
Remote & Global Business Strategy – A pioneer in remote management, having built and scaled fully remote companies from day one.
-
Entrepreneurial Growth & Scaling – Experience in scaling businesses across industries, including mergers and acquisitions.
-
Sales & Business Development – From cold outreach to conference-stage pitching, I have a hands-on approach across the entire sales funnel.
-
Marketing & Branding – A marketing and branding expert with a strong track record in positioning businesses for success.
-
Data-Driven Decision Making – A numbers enthusiast (yes, I love Excel!), skilled in analysis and financial strategy.
-
Keynote Speaker & Thought Leader – Regularly speaking at events on remote work, leadership, and entrepreneurship.
Most coaches give you tactics. Some give you mindset work. I give you both
Leadership Foundations Coaching
For professionals stepping into their first leadership role whether you've just been promoted or are building your first team
What You Get:
Confidence & Identity
-
Define your authentic leadership style (not just copying your old boss)
-
Overcome imposter syndrome and own your new role with clarity
-
Build the confidence to make decisions and stand by them
Communication & Influence
-
Master difficult conversations without second-guessing yourself
-
Learn to communicate vision and direction that actually inspires your team
-
Develop executive presence that commands respect naturally
Team Building & Management
-
Navigate your first hiring decisions with confidence
-
Build delegation skills so you're leading, not just doing
-
Create team structures that scale beyond you
Emotional Resilience
-
Manage stress and decision fatigue without burning out
-
Develop emotional intelligence to read your team and adapt
-
Build resilience for the long game of leadership
Overcome your fears
-
Recognize and celebrate your wins instead of dismissing them as "luck"
-
Use CBT-backed techniques to challenge "I'm not ready" and "I don't belong here" thoughts
-
Develop the inner authority to trust your judgment and make decisions without constant validation
-
Reframe failure as feedback, not proof you're not cut out for leadership
What's Included:
-
Weekly 1:1 coaching sessions (60 min)
-
Personalized leadership development plan
-
Between-session support via messaging
-
Tools and frameworks you can use immediately
-
Accountability to turn insights into action
Duration: 3 months
Entrepreneurial Launch Coaching
For first-time entrepreneurs ready to turn their idea into reality whether you're still employed and planning your exit, or you've already taken the leap and started building.
What You Get:
Idea Validation & Market Fit
-
Validate your business idea before investing months (or money) in the wrong direction
-
Understand what your market actually needs vs. what you think they want
-
Build a business model that works in the real world, not just on paper
Business Foundations & Strategy
-
Create a clear, actionable business plan and go-to-market strategy
-
Design your business canvas and revenue model
-
Build operational foundations that won't fall apart when you grow
Overcoming Fear & Building Confidence
-
Navigate the fear of leaving stability and stepping into the unknown
-
Overcome imposter syndrome and believe in yourself and your offering
-
Build resilience to handle rejection, setbacks, and the inevitable pivots
Sustainable Growth Planning
-
Design a customer acquisition strategy that actually works
-
Map your sales funnel from awareness to conversion
-
Create SMART goals and OKRs so you know exactly what to focus on each week
Mindset & Mental Health
-
Shift from employee mindset to founder mindset
-
Learn to manage the freedom (and responsibility) of being your own boss
-
Prevent burnout before it happens by building sustainable habits
What's Included:
-
Weekly 1:1 coaching sessions (60 min)
-
Business validation framework and templates
-
OKR/KPI tracking system for accountability
-
Access to my network and resources
-
Between-session support for quick questions
-
Your "second brain" for bouncing ideas without judgment
Duration: 3 months
Coaching Programs
This is for YOU if:
✓ You're ready to turn your vision into reality, not just keep dreaming about it
✓ You want freedom - financial, time, and location - and you're willing to work for it
✓ You're ready to be your own boss and learn what that actually takes
✓ You want to turn ideas into opportunities instead of staying stuck in analysis paralysis
✓ You're tired of figuring this out alone and want a trusted second brain
✓ You're willing to be uncomfortable because you know that's where growth happens
✓ You want to build something sustainable, not burn out chasing quick wins
✓ You're ready to face your fears instead of letting them quietly run your life
✓ You want accountability and tough love, not just cheerleading
✓ You're playing the long game: building something that lasts, not just what looks good online
My mission
Why I Do This
I believe that healthy, confident entrepreneurs and leaders don't just build better businesses - they change the world. But most founders burn out within two years. Most new leaders spend their first year drowning in self-doubt.
That's the problem I'm here to solve.
My mission is simple: empower ambitious professionals to build success that lasts without sacrificing their mental health, relationships, or sanity in the process.
I help you build confidence, take action, and lead with clarity.
Not in some distant future. Right now.
Testimonials
"Ola played a key role in my career growth, offering invaluable guidance and support that helped me develop both professionally and personally. Any team would be incredibly lucky to have her at the helm! Her leadership and organizational skills are truly outstanding—she navigates challenges with ease, keeps the team aligned, and fosters a collaborative, productive environment. Beyond that, her soft skills make all the difference. She is approachable, empathetic, and someone I could always trust with both professional and personal matters"
Maria B., Founder, Marketing Agency
See how professionals and entrepreneurs have transformed their careers and businesses with my coaching
Let’s Connect.
Follow me on LinkedIn or reach out directly for any inquiries
