The Playbook by Kurt Faustin
A Monthly Series for Entrepreneurs and Nonprofit Leaders
A 4-Session Experiential Learning Series: Money · Decisions · Emotional Discipline
The Playbook is a 4-session experiential learning program designed for early-stage entrepreneurs and nonprofit leaders who are actively building, growing, or preparing to scale their ventures.
Each session pairs a specific business domain (funding, marketing, finance, or systems) with the emotional intelligence and mental performance research that determines whether people actually apply what they learn.
Sessions are led by Kurt Faustin and feature expert panelists with lived and professional expertise in the session topic
The Playbook Series
Nonprofit Funding, Grants, & Financial Sustainability
Marketing, Visibility, & Strategic Collaboration
Money, Taxes, & Financial Clarity
Systems, Structures, & Consistent Execution
Nonprofit Funding, Grants, & Financial Sustainability
The nonprofit funding ecosystem is worth over $500 billion annually in the United States, yet 80% of nonprofits report chronic financial instability (Nonprofit Finance Fund, 2023). The barrier is rarely worthiness. It is access, language, and relationships. This session demystifies the funding landscape and gives participants a concrete roadmap to pursue it.
What you will learn:
● The full funding landscape: grants, donors, sponsors, earned revenue
● Grant writing fundamentals: what funders actually read
● Positioning your mission in funders’ language, not yours
● Building and sustaining relationships with funding partners
● How to create a 12-month funding calendar
Emotional Intelligence Focus:
● Scarcity mindset and its effect on funding behavior
● Fear of rejection, and why most leaders never apply
● Chronic undervaluing of mission and impact
● Shifting from asking for money to presenting an investment opportunity
Marketing, Branding, & Strategic Collaboration
The most overlooked growth lever for early-stage entrepreneurs isn’t product quality. It’s strategic visibility. Research from HubSpot’s 2023 State of Marketing report found that businesses with documented marketing strategies are 313% more likely to achieve their goals. Most small business owners spend time creating content and almost no time distributing it. This session flips that equation.
What you will learn:
● Brand positioning: what makes you the obvious choice
● Content vs. distribution, and why most businesses get this backwards
● Strategic partnerships as a distribution channel
● Outreach frameworks that generate warm leads
● A 30-day visibility sprint: simple, measurable, repeatable
Emotional Intelligence Focus:
● Fear of visibility: the psychology behind staying small
● Perfectionism as a procrastination strategy
● Comparison culture and its effect on execution
● Building a value-first identity as a business owner
Money, Taxes, & Financial Clarity
Financial avoidance is one of the most documented behavioral patterns among small business owners. Research from the Association of Certified Fraud Examiners (2022) found that businesses without basic financial tracking are 3x more likely to close within 5 years. This session gives participants the knowledge, and the emotional permission, to open their books.
What you will learn:
● LLC vs S-Corp: when structure matters
● Cash flow vs profit, and why confusing them is fatal
● Write-offs, deductions, and what your CPA needs from you
● A simple financial tracking system you’ll actually use
● When and how to hire a CPA vs. DIY your books
Emotional Intelligence Focus:
● Money avoidance as an anxiety response (not a character flaw)
● Scarcity mindset vs. ownership mindset: the neuroscience
● Reactive spending vs. intentional financial decisions
● The emotional cost of financial avoidance over time
Systems, Structures, & Consistent Execution
Inconsistency is the most common self-reported challenge among early-stage entrepreneurs, and the most misdiagnosed. Research from the American Psychological Association (2022) identifies cognitive overload as the primary driver of behavioral inconsistency, not motivation or character. When entrepreneurs lack simple operational systems, every decision becomes a new one, and decision fatigue compounds into paralysis. This session builds the infrastructure that makes consistency inevitable.
What you will learn:
● Time blocking and workflow design for founders
● Lead tracking without expensive CRM software
● Content and task management systems that scale
● The Weekly Execution Stack: a repeatable weekly rhythm
● Idea management: capturing without drowning
Emotional Intelligence Focus:
● Overwhelm as a neurological state, not a personal failure
● Why motivation fails and discipline structures succeed
● Emotional regulation during high-pressure execution periods
● Avoiding the identity trap: being a founder vs. doing founder work
About Kurt Faustin
Founder & CEO, The Dropout · Certified Brain-Based Coach · Speaker & Success Strategist
Kurt Faustin has spent over a decade at the intersection of emotional intelligence, performance coaching, and community development. As founder of The Dropout, a Boston-based nonprofit recognized by both the Commonwealth of Massachusetts and the City of Boston, Kurt has reached more than 50,000 individuals through keynotes, workshops, and programs designed to bridge the gap between mental health and high performance.
Kurt is a certified Brain-Based Coach and has been appointed to a City of Boston commission. His work spans schools, universities, nonprofits, and corporate partners, all united by one core belief: that execution is an emotional capacity problem before it is a strategy problem. He brings the same framework that has helped youth, educators, and executives to this series, adapted specifically for the pressures and emotional terrain of early-stage entrepreneurship.
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