Keith GilletteStrategy + Systems • People + Process

Outcome-driven, process-oriented leader passionate about efficiency, effectiveness, education, environment, & economy.

•Experienced team leader with proven management, interpersonal, technical, & analytic skills.
•Past President, Illinois Chief Technology Officers.
•Master's degrees in Business Administration and IT Systems Management.
•Broad experience in systems analysis & design, project management, & process improvement.
•Excellent oral & written communication skills.

Keith has more than 15 years of experience designing and delivering information technology solutions in K-20 educational contexts. Keith has launched and administered two 1:1 student notebook computer learning initiatives. In addition to multi-platform network and systems design and administration experience, Keith has expertise in IT infrastructure design and construction management in both new building and facilities remodeling. Keith holds a Master of Science in Information & Telecommunications Systems Management, a Master of Business Administration from the University of Chicago Booth School of Business, as well as numerous IT industry certifications. Keith is a senior member of the American Society for Quality and brings Six Sigma certification and a quality systems/process management orientation to his work in strategic planning, systems design, project coordination, and operations management.

Recent Answers

Personally, I like David Allen's *Getting Things Done* system for short-term planning and task management. Taylor Pearson has written a useful essay on his "anti-fragile" planning process:

I think that's a hard question to answer in the abstract without knowing the extent of your IP, the relative market potential for the product, your desire or need for institutional investment, and the relative contributions of your future potential partners. Have you considered a dynamic equity split arrangements for the partners you wish to attract? I recommend taking a look at as one well thought-out dynamic equity split alternative.

What's the business model for the freelancing platform?

Have you looked at They are a startup concierge matchmaking subscription service for founders looking to share equity or cash/equity splits with contributors.

Are you familiar with I think a dynamic equity split system like Mike Moyer's "Grunt Fund" is a perfect match for a platform approach to startup collaboration.

Are you pursuing a for-profit or non-profit model for your school? Do you have an education background? Are you certified to run Montessori school?

Initial recommendations:
•Investigate the California Department of Education requirements for operating an educational institution.
•Investigate the requirements for the two accrediting bodies for Montessori: AMS <> and AMI <>. While not required, private schools are reputation-based and accreditation plays into your brand equity.
•Investigate the requirements for the regional independent school accrediting body. While not required, many Montessori schools struggle to keep enrollment through elementary and middle school as parents expectations shift to college preparation, which Montessori does not have strong brand recognition for, and adopt a academic rigor / progressive education model of education accredited by a regional independent schools association for credibility.

While starting with kindergarten frees you from the state early childhood childcare regulations, which can be onerous, it also cuts off your funnel. As a school brand, Montessori is precisely strongest at the very early ages, so you may have a challenge attracting families who already started their child with a Montessori school that has a preschool. Many Montessori school start with 18-month infant & parent programs.

Best regards,
Keith Gillette

If you are planning to bootstrap and attract co-founders before raising capital, you may want to consider a dynamic equity split such as the "Grunt Fund" outlined by Mike Moyers at

I have no affiliation with the system. I just consider it a fair, transparent, and low-friction way to get started.

Having helped start a similar school (a boarding high school focused on ethics, environment, & innovation), I can tell you that the steps involved are similar to starting any business, though a school will give you a few unique questions to answer first:

•Will you operate as a charter or independent/private school?
•Will you organize as a for-profit or not-for-profit entity?
•Will you deliver instruction in person or on-line or blended?
•What grade/age levels will you teach?

The answers to those questions will then drive both the logistics of where to start as well as much of your high-level business strategy planning. For example, if you're planning in-person instruction, then your start-up strategy must be driven by demographics, as outside of elite boarding schools, bricks-and-mortar schools are largely location-based plays.

Beyond that, I think you can adapt a startup methodology like Lean Startup or Disciplined Entrepreneurship to provide a framework for testing your assumptions and moving your idea forward. I'd recommend starting by creating a Business Model Canvas that answers the basic business questions, including target market, unique value proposition, revenue (tuition) model, cost structure (teacher salaries!), etc.

I'd be happy to help you think through a startup plan, so feel free to reach out. Good luck!

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