The Team Behind HomeBase: Why This Founding Team and Advisory Board Are Uniquely Positioned to Transform Alternative Education

The 10,000-Hour Problem: Why EdTech Startups Fail

Malcolm Gladwell's 10,000-hour rule suggests mastery requires deliberate practice over years. But here's what EdTech investors learned the hard way: over 60% of the 2025 North America EdTech 200 companies were founded in the past six years, yet most will fail within three.

Why? Because educational technology sits at the intersection of three brutal complexity layers:

1. Regulatory Compliance: Each state has different standards, documentation requirements, and review processes
2. Pedagogical Science: What engages students isn't what passes compliance reviews
3. Mental Health Awareness: Alternative education families often have children with unique social-emotional needs

Most founding teams have deep expertise in one, maybe two of these areas. HomeBase's founding team has all three—and the receipts to prove it.

The Founding Triangle: When Expertise Becomes Unfair Advantage

Chris Short: The Product Architect (10+ Years Software Delivery)

Chris Short brings a decade of software product delivery across enterprises, nonprofits, schools, and startups. Here's why that matters: EdTech software development companies emphasize that employers highly value 10+ years of practical experience, especially in senior engineering positions managing large teams and budgets.

Chris isn't a generalist software engineer who pivoted to education. As Head of Delivery at The Holistic Consulting Group, he's spent 10+ years in software product delivery across diverse sectors—real enterprises, nonprofits, schools, and startups. He leads the development of AI-powered solutions that integrate custom software, intelligent automation, and advanced prompt engineering. He knows where platforms break—not theoretically, but from managing real implementations with real organizations.

Taylor Short: The Market Translator (10+ Years Startup Scaling)

Taylor Short brings 10+ years of startup scaling and consulting, specializing in marketing strategy, branding, and research. But here's the critical detail: not just any marketing—marketing for belief-driven products where the customer isn't buying features, they're buying identity transformation.

Alternative education parents aren't comparison-shopping curriculum platforms. They're making identity statements about who they are as parents and what they believe about learning. Taylor's expertise in belief-driven leadership and market positioning means she understands that HomeBase isn't competing on price or features—it's competing on tribal affiliation.

She knows how to drive outreach, fundraising, and growth for products where emotional resonance matters more than rational feature comparison. In a market where 49% of Florida K-12 students now attend schools of choice, understanding identity-driven decision-making is the difference between viral growth and stagnant conversion rates.

Sylvie Silva: The Learning Architect (Triple-Certified Educator & Therapist)

Sylvie Silva is where HomeBase's competitive moat gets serious. She's not just an educator—she's a triple-certified educator, wilderness therapist, and clinical mental health counselor. As Founder and Program Director of The Cicada Institute, she has been working with teens for most of her life, creating curriculum specifically for their most potent and supported growth.

Here's why this combination is rare: To become a Clinical Adventure Therapist, you must be a licensed mental health practitioner with a master's degree or higher, AND have wilderness therapy credentials AND educational curriculum development experience. That's three separate 10,000-hour journeys converging in one person.

Sylvie's Cicada Institute uses rites-of-passage techniques present for centuries to guide emotionally gifted and spiritually talented teens into fully-actualized, potent development. The program incorporates ancient wisdom such as mindfulness training, yoga, plant medicine, bushcraft, music, and permaculture. Sylvie brings advanced credentials in wilderness therapy and Gestalt Therapy, leading innovative social-emotional learning program design specifically for BIPOC and LGBTQIA+ communities.

She doesn't just understand pedagogy—she understands the mental health landscape of alternative education families, many of whom left traditional schools precisely because their children have unique social-emotional needs.

The Advisory Amplifiers: Strategic Depth That De-Risks Scale

Most startup advisory boards are cosmetic—names on a website that sound impressive but provide little tactical value. HomeBase's advisors aren't ornamental. Each one fills a specific execution gap in the path from pilot to national scale.

David Tuthill: The Policy Navigator (Step Up For Students)

David Tuthill is a Legislative Analyst at Step Up For Students, the nonprofit administering approximately 99 percent of school choice scholarships in Florida. This isn't theoretical policy work—this is the operational front lines of the largest school choice implementation in America.

In 2023, Florida passed universal school choice legislation, making all K-12 students eligible for private school scholarships. Governor Ron DeSantis signed HB 1, the most expansive education choice bill in the nation, removing financial eligibility requirements and enrollment caps. David was inside that implementation.

When HomeBase scales from North Carolina to Texas, Florida, and Georgia, David knows exactly which legislative barriers will appear, which state education departments will slow-walk approvals, and how to structure compliance documentation for different regulatory environments. He's already done it at scale—1.7 million students at scale.

Rob Vanderwerf: The Transformation Strategist (KPMG Global Leader)

Rob Vanderwerf serves as KPMG's Global Transformation Strategy Leader, specializing in growth strategy and operations improvement. As a Principal in KPMG's Orange County office, he brings more than 25 years of experience serving Fortune 500, mid-market, and start-up organizations across industries including Technology, Financial, Healthcare, Consumer, Industrial, and Media & Entertainment.

KPMG has over 1,600 global professionals dedicated to developing and executing digital and data strategy, and Rob leads that transformation practice. He advises CEOs and management teams on delivering sustainable, long-term value by navigating the complexity of business transformation caused by globalization, constant shifts in technology, and evolving regulatory environments.

Here's what matters: A 2024 KPMG survey found that 88% of US companies reported improvements in performance and profits from technology-driven transformation initiatives, nearly double the 45% from the previous year. Rob is a published thought leader who presents at university and industry conferences regarding innovation, technology, and business performance improvement—he's not just implementing these transformations, he's defining the frameworks others follow.

When HomeBase goes from 500 families to 50,000 families, the technology doesn't break—the organization breaks. Rob has guided Fortune 500 companies through major change management and business transformation across multiple industries. He knows how to scale operations, build connected enterprises, and implement digital solutions without losing the cultural DNA that made the pilot successful.

Charles Brockman: The Technical Operator (Technology Consulting)

Charles Brockman brings diverse experience in technology consulting, engineering, and media. Former director of technical support call center operations and consultant for major firms, Charles specializes in technical operations, applied technology, and engineering at scale.

When parents call at 11 PM because they can't access their child's lesson plan for tomorrow morning, that's not a product problem—it's an operations problem. Charles has run technical support at scale. He knows how to build customer success infrastructure, triage engineering priorities, and maintain uptime when families depend on the platform daily.

DJ Skalsky: The Mission-Driven Strategist (Healthcare & Nonprofit)

DJ Skalsky is a Managing Director noted for work with healthcare, nonprofit, and public sector organizations. He specializes in strategy, digital transformation, and operational improvement for mission-driven clients.

HomeBase isn't a SaaS product optimizing for maximum revenue extraction. It's a mission-driven platform serving families who feel abandoned by traditional education. DJ understands how to balance financial sustainability with mission integrity—how to scale without losing the values that attracted early adopters.

He's led IT advisory and implementation projects for healthcare and nonprofit organizations where the stakes are higher than revenue—where failure means real harm to vulnerable populations. That discipline translates directly to HomeBase, where families are trusting the platform with their children's education.

Deborah DeLisle: The Grassroots Innovator (30 Years Outdoor Education)

Deborah DeLisle is a multifaceted educator whose credentials span an unusually broad range: degrees in Art, Engineering, Organizational Management, Early Childhood, K-6 Education, Education Administration, and Experiential Learning. But credentials don't capture what makes Deborah uniquely valuable to HomeBase—it's what she's built from scratch in the rural Appalachian mountains.

As Founder and Executive Director of Madison County Community Learning Centers, Deborah started with one community learning center in Hot Springs, NC in 2008 and evolved it into a thriving dual-campus operation: a preschool for ages 3-5 and Woodson Branch Nature School, serving K-8 students on a 30-acre farm and forest in Marshall, NC.

Here's why this matters for HomeBase: Deborah didn't just read about nature-based experiential learning—she's spent 30 years implementing it with children outdoors. Her schools integrate farm and forest fully into curriculum, teaching traditional academics alongside Agriculture, Art, and Outdoor Education. Fifth-graders attend school at a local prairie wetland, where science, math, and writing are taught through onsite research. The model works: Woodson Branch recently received a food resilience grant from Mission Health, validating the sustainability focus embedded in the curriculum.

Deborah is renowned as a grassroots innovator supporting small-town communities through business and festival design alongside education projects. She leads tours sharing her experience with designing, opening, and maintaining a successful alternative school in rural Appalachia—exactly the scaling challenge HomeBase will face when expanding from Charlotte suburbs to smaller communities across North Carolina and beyond.

Deborah's passion for revolutionizing education through experiential learning and her commitment to fostering community through MCCLC's mission—"empower communities with experiential nature-based education to fortify global balance through preparedness"—aligns perfectly with HomeBase's vision. She's not advising from theory. She's advising from 17 years of boots-on-the-ground implementation in exactly the alternative education space HomeBase serves.

The Honest Assessment: What Could Go Wrong?

Every startup story sounds bulletproof on paper. So let's talk about the vulnerabilities—the places where even a strong founding team can stumble.

Vulnerability 1: Founder Dynamics Under Pressure

Three co-founders with deep expertise can become three co-founders with competing visions when revenue misses projections or an investor demands a pivot. The strongest founding teams fracture under the pressure of scaling.

The Mitigation: Chris, Taylor, and Sylvie have complementary rather than overlapping expertise. Chris owns technical delivery, Taylor owns growth and market positioning, Sylvie owns pedagogical integrity. Clear lanes reduce ego collision points.

Vulnerability 2: Advisory Board Disengagement Without Equity Skin in the Game

Most advisors are busy people who agreed to lend their name but have limited bandwidth for tactical support. HomeBase's current advisory structure—providing guidance without financial compensation or equity—could mean advisors disappear when critical challenges arise. When HomeBase hits a regulatory wall in Texas or needs to restructure operations for 10x growth, will advisors with no equity stake actually show up?

The Mitigation: The current structure is intentionally designed for the proof-of-concept phase. David Tuthill's work at Step Up For Students is directly adjacent to HomeBase's mission—school choice implementation success directly validates his policy expertise. Rob Vanderwerf's KPMG transformation work overlaps with HomeBase's scaling challenges—a successful EdTech transformation becomes a case study. Deborah DeLisle's rural alternative education model gains credibility when HomeBase scales to small-town communities. These aren't vanity advisors—they have professional interest in HomeBase's success because it validates their own domains and expands their networks. As HomeBase proves the model and enters formal funding rounds, there's mutual interest in formalizing these relationships with equity alignment.

Vulnerability 3: The "Expert Trap"—Building for Ourselves

Expert founding teams sometimes build for themselves rather than their actual market. Sylvie knows what elite therapeutic education looks like, but will middle-class homeschool parents in suburban Charlotte pay $49/month for features they don't understand?

The Mitigation: Taylor's marketing expertise keeps the team market-focused rather than feature-focused. Her 10+ years scaling startups means she's seen the expert trap before and knows how to validate market demand before building.

The Pattern That Matters: Complementary Mastery

Research on successful EdTech startups reveals a pattern: companies like Maven (co-founded by Gagan Biyani of Udemy, Wes Kao of altMBA, and Shreyans Bhansali of Socratic/Google) and Marathon Education (Duc, former TPG Capital education investor, and Tung, serial tech entrepreneur) succeed because founding teams combine complementary expertise rather than redundant skills.

HomeBase follows this pattern. Chris brings product execution. Taylor brings market positioning. Sylvie brings pedagogical and therapeutic science. The advisors fill the gaps: David handles policy navigation, Rob guides transformation strategy, Charles manages technical operations, DJ ensures mission alignment.

This isn't seven people doing overlapping work. This is seven people with non-overlapping expertise covering the entire value chain from regulatory compliance to customer success.

The Tipping Point: When Expertise Becomes Inevitability

In Outliers, Gladwell argues that success comes from being in the right place at the right time with the right preparation. HomeBase has all three:

• Right Place: North Carolina with 193,000+ homeschool families and growing microschool movement
• Right Time: 2025, when alternative education is mainstream (49% of Florida students) and AI makes personalized learning economically viable
• Right Preparation: Founding team with 30+ combined years of directly relevant expertise, plus strategic advisors who've already done this at scale

Will HomeBase succeed? The honest answer: most startups fail, regardless of team quality. Market timing matters. Execution matters. Luck matters.

But if you're an investor choosing between twenty EdTech pitches, here's what separates HomeBase: this team has already spent the 10,000 hours. Actually, closer to 30,000 hours across three co-founders, each mastering their domain before starting the company.

They're not learning regulatory compliance on the fly—David's already done it for 1.7 million students. They're not figuring out transformation strategy under pressure—Rob's done it for Fortune 500 companies. They're not guessing at therapeutic integration—Sylvie's triple-certified.

In a market where 4.6 million families are already choosing alternative education despite massive friction, HomeBase has the team that can remove that friction at scale. That's not a guarantee of success—but it's as close to an unfair advantage as startups get.