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Expert  Coaching

I have a playbook that works after starting ten companies, two exits, raising $20 million in private market capital, and helping over 100 founders solve their biggest business challenges.

Leaders are not searching for more gurus, inspiring quotes, pep talks, or full-time cheerleaders.

They seek 
practical help, competent support, relevant training, the right tools, accurate analyses, and effective action steps that get results.

This is what I do. Hands-on. Pulling from a deep playbook of processes, formulas, and tool sets, I work individually with founders and business leaders at every level, from solopreneurs to enterprise CEOs, helping address every imaginable challenge to deliver visible, lasting results.

I decompile complexities into simplicities, map a path to realistic solutions, and guide leaders on that path as their success catalyst. 

Equipped to tackle what may be perceived as impossible problems, I have yet to meet a founder, dive into a start-up, or immerse in a business, product, or delivery, resource, or launch situations that cannot be resolved.  

Let me help do the same with you. 

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What I offer.

I've been helping leaders and entrepreneurs transform at every level for over 15 years. I do this through a hands-on engagement to assess, strategize, program, and implement with clear guidance that gets results.

This is done by providing framed, focused, and practical strategies, observational accuracy, deft insights, bias-free analyses, relevant information, targeted problem-solving, balanced thought, practical reasoning, user-centric thinking, empathetic rationales, experience, competence, knowledge, prediction and actionable program steps in a clear, concise and understandable form that I work with you on to achieve the results you need. These include:

  • business or product strategy

  • tech stack analysis, blueprint & full stack development*

  • go-to-market strategy

  • product-market fit resolution

  • delivery scaling (up and downstream)

  • financial modeling, financial management*

  • legal planning, legal resolutions, IP protection*

  • tech, exec, co-founder resources

  • private market capital* (startup, early- and later-stage)

  • exit mapping (IPO or private sale)

  • mindset, time & performance optimization

  • first-time-founder training & coaching

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*I am not a licensed attorney nor a FINRA-licensed Financial Advisor. But I will provide you with the necessary business advice you critically need while facilitating any such needed expertise through my vast network and deep bench of proficient attorneys, CPAs, broker-dealers, and other specialists to help tackle your most pressing legal or finance needs. I receive no compensation from any of my network referrals and simply include this as part of any resolution development. 

My promises to you.

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Every entrepreneurial challenge requires a unique solution that caters to the specific needs of the founder(s), their teams, that startup, its business model, product, service, circumstance, or situation. There is no one solution that fits all. 

My approach is repeatable and predictable, guaranteeing reliable outcomes, regardless of circumstance.

1. I listen. A lot. It's how we start, and how we'll always end. 
2. I do not tell you what to think, do, or decide. I only guide.
3. I'm brutally honest. Truth can be hard, but it's a cure for weakness.
4. I will work harder (and more) than you'll expect me to.
5. I am never vague. I provide exact direction & action steps.
6. I will keep you accountable, every step of the way.  
7. Once we begin, my commitment
will not be broken.

As a founder, you have high standards for the qualities you look for in a partner: loyalty, honesty, competence, and proven results. It only makes sense to expect the same level of excellence from a personal coach or collaborator. After all, you deserve nothing less than the very best.

What makes me qualified to coach you?

Ultimately, the decision is yours to make. However, I can offer valuable insights to assist you in making a well-informed choice.
My extensive experience includes triumphs, setbacks, advice from some of the most successful entrepreneurs and investors in the industry, negotiations with high net worth individuals, collaborations with top-tier corporate decision-makers, and hands-on involvement with hundreds of entrepreneurs and founders like yourself while building my own vision and those of my incredible partners.
I am here to leverage all of my knowledge and skills to effectively ensure and support your success.


  • 10x founder/co-

  • 2 exits ($130mm TOT - AutoLoop™ acquired by Affinitiv™; private transaction of an app by ADP™)

  • $20 million raised in private market capital 

  • 6x CEO/President/COO

  • 100+ founders/entrepreneurs coached, advised, mentored

  • Product Lab LLC from launch to Cash-Flow-Positive in 10 months

  • Blockrails™ co-built startup recently declared an NAR® national program

  • Founding Principal, Board, EVP of Commonwealth Capital LLC

  • Board Chair at Neos Equity Group

  • MIT 2x Certified (MIT Startup Boot Camp & MIT Blockchain Technology for Business)

  • CBE (Certified Blockchain Expert)

  • Insead Business School, Blue Ocean Strategy Certified

  • AIU BBA, summa cum laude, International Business

  • Northwestern California School of Law (JD candidate, incomplete)

  • Public Speaker, Published Author, Philanthropist

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Social proof:

"...watching him build a twelve-man [start-up] operation into a crackerjack operation of over 250+ was an invaluable opportunity for me to observe first hand what it means to truly understand organizational efficiency, personnel management and public relations. Jason is a tirelessly energetic, highly productive and extremely capable professional that any organization can count themselves very lucky to have on their team."

Ken Daniells, FL

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Qualities of Guidance.

Understanding the qualities of professional or expert guidance can sometimes be difficult. Defining them, however, should be clear and simple.

These Qualities of Guidance woven into the very fabric of my coaching with everyone I work with to success.

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OPENNESS. I facilitate open-ended communication and interaction. I empower you to draw your own conclusions without any predetermined directions. My patient listening enables you to reach your own conclusions without any judgment or imposition of how things "should be."

ENTHUSIASM. I possess an abundance of energy and enthusiasm that enables me to celebrate even the smallest of victories, accurately identify your strengths & weaknesses, and develop powerful frameworks that will effectively motivate and excite you.

EMPATHY. My sessions are designed to provide you with a secure and compassionate space. My goal is to assist you in reaching your long-term objectives while recognizing and valuing your triggers and motivations, empowering you to push beyond your limits.

SELF-AWARENESS. My sole focus is on you, not myself. Your journey and challenges take precedence; I will never stray from that. There's no need for me to delve into my own life, conditions, or stories when all that matters is assisting you with the utmost confidence and dedication.

COMMITMENT. Rest assured that I am fully committed to supporting you throughout your journey, even during the most challenging times. I recognize that you reached out for help because you require assistance, and I will always honor and value that decision.

TRUST. When engaging a coach, trust is paramount, even if it involves facing uncomfortable vulnerabilities. As an experienced coach who has worked with individuals from all walks of life coming from criminal reform to mending broken marriages, I approach every client without judgment. Confidentiality is my highest priority, and I am bound only by the law, never by public opinion.

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More Questions?

Send me an email with any questions you may have and I will get back to you with a reply as soon as I can.

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Legal Disclaimer


The information contained within websites are not a substitute for professional advice such as a Medical Doctor or a medically Licensed Counselor. The information provided by does not constitute legal or professional advice nor is it intended to be. Diagnosing psychological or medical conditions is for trained medical professionals (Physicians and Therapists), not for a Business Coach. Business Coaching is not a substitute for engaging the services of a CPA or Attorney. or Jason Bennick, LLC, is not a lawyer or certified public accountant, and anything contained in this site or said, written or provided as part of the coaching services should not be considered legal or financial advice, and you should always seek appropriate counsel for such professional services when needed. 

Any decisions you make, and the consequences thereof are your own. Under no circumstances may you hold, Jason Bennick, LLC, or its employees, officers, partners or affiliates liable for any actions that you take. You agree not to hold, Jason Bennick, LLC, or any of its employees, officers, partners or affiliates liable for any loss or cost incurred by you, or any person related or associated with you, as a result of materials or techniques, or coaching services, offered by

Results are not guaranteed. holds no responsibility for the actions, choices, or decisions taken or made by the client.

The owner of and contributors to accept no responsibility or liability whatsoever for any harm, real or imagined, from the use or dissemination of information contained here, or as a result of materials or techniques, or coaching services, offered by

If these terms are not agreeable, please do not engage the coaching services of By engaging any of the services at any point of interaction between and yourself, you have agreed to all Terms and Conditions. 

©2023 Jason Bennick, Jason Bennick LLC. All Rights Reserved. 

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