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Sylvester (“Syl”) Di Diego
Advisor, Interim Executive, Consultant
Sylvester (“Syl”) Di_Diego accelerates ventures as Advisor, Interim, Executive, and Consultant for Startups, Small Businesses, Large Enterprises, Investors, and Nonprofits. Syl leverages his A to Z experience in startups, small businesses, venture backed technology firms, and large enterprises. He serves on both sides of the investor table and across all stages of the venture and business lifecycle.
Results and Impact Overview:
• $300 Million Capital Raised
• $100,000 to $20 Million per raise | Grants – Equity – Loans
• 300+ Clients Served
• 50 Business Launches | 50 Onshore Plants in USA | 7 Turnarounds
• 4 Incubators/Accelerator (11 service years)
• 1 Incubator Fund Managed (Global Fortune 100)
• $1 Billion direct equity portfolio Co-Managed – 500 companies ( Global Fortune 100)
Digital Business Building & Financing Achieved:
• 10+ Ecommerce Platforms (including $10M & $20M raised)
• 10 Websites (up to $5M budget each)
• 4 SaaS Platforms (ventures)
• 2 Apps (ventures)
CLIENT TESTIMONIAL
STRATEGIC PLANNING & PRODUCT DEVELOPMENT
EHealth patented fitness kinetic tracking wearable with online social gaming community/rewards platform for exercise motivation and obesity reduction.
“Whether you know your business or think you know your business, strategic planning sessions with Sylvester will help validate your business assumptions, uncover opportunities perhaps overlooked, and force the assessment and possible correction of your strategy.”
Seth Tropper
President & Founder (& serial entrepreneur)
Swich2Health Corporation
North Brunswick, New Jersey USA
Results: Successfully expanded product offerings, built online communities, gained sponsors, and expanded markets globally.
Successful strategic exit though Fitbit acquisition/license of technology/company.
Services: Business Plan Critique | Venture Leadership Program | 1-1 & Team Venture Consulting | ECommerce Consultation.
Read more of Syl’s Client Testimonials.
SERVICES
Syl provides mission critical, innovative and timely services and solutions to help clients succeed in both opportunistic and challenging situations across the venture lifecycle – from concept and launch to operations scaling and exit. As successful outcomes are achieved, the relationship often expands as clients call upon Syl to assist with their evolving needs and priorities.
Why Syl? By leveraging his extensive track record and tool kit, Syl saves clients time and money by minimizing ramp-up time and hand-offs, maximizing implementation speed, and successfully crossing-over chasms into a new stage of business. This has high value for clients – as compared to a client’s hiring multiple, separate consultants who need to join teams and catch-up to executive priorities, client culture and commercialization momentum.
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Advisor, Coach, & Consultant Services

Syl Di Diego serves as advisor, coach, and consultant to investors, entrepreneurs, startups, small business owners, executives, incubators, accelerators, venture studios, and non-profit leaders. Experience: over 20 years.
Services
Services include leadership coaching and mentoring, technology commercialization roadmaps, strategic planning and playbooks, stakeholder alignment, investor-ready business plans and pitch decks, market research and analysis, market forecasts and strategies, financial models and forecasts, capital raising, go-to-market, strategic alliances, innovation facilitation and training, and project management.
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CEO & Board Advisory Services

Syl Di Diego serves CEOs and board members in the areas of alignment, strategy, decision making, problem solving, crisis management, profitability, ROI, new investment, turnaround, and digital transformation! Experience: Over 20 years.
Advisory Experience
- C-Suite Executives of Venture Backed Companies
- Executives of Global Fortune 50 Conglomerate (London Stock Exchange Listed)
- Board Members, C-Suite, and Executives of Global Fortune 100 Conglomerates (Tokyo Stock Exchange Listed)
- C-Suite Executives of Subsidiaries of global Fortune 100 Conglomerate (Tokyo Stock Exchange Listed)
Board and Committee Roles Served
- Chair & Co-Founder, Consul Program New Jersey for Life Sciences, Health, Wellness, Raritan, New Jersey USA
- Advisory Board Member, Center for International Business & Education at Raritan Valley Community College Raritan, New Jersey USA
- Sub-Committee Leader, Foreign Direct Investment (FDI) to Japan, American Chamber of Commerce in Japan. Tokyo, JAPAN
- Investment Committee Staff, Global Fortune 100 Conglomerate (Portfolio of 500 Direct-Equity Subsidiary Companies)
- Founding Member, Mitsubishi Foundation (USA) – Corporate Board Appointed, New York, NY USA
- Member, Pension Committee, Mitsubishi International Corporation (USA) – Corporate Board Appointed New York, NY USA
- Member, 401K Management Committee, Mitsubishi International Corporation (USA) – Corporate Board Appointed New York, NY USA
- Member, Non-Profit Board, Madison, NJ, USA
- Member, Non-Profit Board, Liberty Corner, NJ USA
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Accelerators, Incubators, and Venture Studios Services

Syl Di Diego provides various customized venture leadership training programs and services to tenants and clients of state, university, and corporate incubators and accelerators. Experience: Over 20 years.
Services:
Services span Technology CEO Leadership Mentoring, technology commercialization, grants, capital fund raising, investor-ready business plans and pitch decks, market analysis, operations planning, go-to-market, competitive market positioning, sales strategies, financial forecasts, strategic alliances, partnership excellence, and prep for pitch and negotiations with venture capital investors, government grant agencies, and corporate investors.
Examples of Signature Multi-Year Programs:
- Accelerator – State EDA Sponsored Commercialization Innovation Center – Life Sciences, Biotech, and Medical Devices. Designed and delivered proprietary curriculum with 20 modules and served 80 ventures over 4 years, Won competitive bid contracts with the State.
- Incubator State University Sponsored for Technology Licensing, Commercialization, and Economic Development in a major US Urban Center. Technology and Health Ventures. Delivered seminars and evaluated viability for technology commercialization, and venture coaching. Over 4 years served portfolio of 60 ventures in technology and health spaces. Entrepreneur-in-Residence.
- Venture Catalyst Program for Global Fortune 100. Co-founder and Program Director. Reinvented Corporate Leadership Training for better deal generation, analysis, and financial results across all business groups – “from soups to satellites”. Led a cohort of 20 executives across the USA. Conceived and designed propriety curriculum of 20 day long modules and stimulated cross-enterprise collaboration. Co-Instructed with HBS Professor and leading industry consultants.
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Digital Services

Syl Di Diego provides Digital Transformation and eCommerce Services to entrepreneurs, small businesses, large enterprises, and nonprofits. Experience: Over 20 years.
Services:
Syl Di Diego works as Digital Consultant, Agile Facilitator and Project Manager, and/or Complete Digital Business Builder / Operator to design, program, configure, and operate apps, websites, eCommerce Stores, and SaaS Platforms, He is active in Small Business and Enterprise Digital Transformation. Depending on client needs, Syl sometimes serves in roles of web conceive, design, development, test, launch, and operate. Syl helps with digital business plans, venture financing, and corporate financing for all sizes of digital businesses – from apps, to eCommerce, SaaS, PaaS, and eMarketplaces.
Project and Sector Examples:
- DTC B2C eCommerce Store – Food & Beverages – Global Fortune 50 (USA)
- First DTC B2C eCommerce Store – Food & Beverages – Global Fortune 50 – Canada
- ePropTech eCommerce Store and Proprietary Data Valuation App Integration – Business Model and Design, Build, Test – Small Business Entrepreneur (USA)
- DTC B2C 3 eCommerce Stores – Consumer OTC Medical Device – Small Product Development Company – USA, UK, and India
- ECommerce Hub of multiple eCommerce Stores – Strategy and Business Model Design – Major Regional Business Group – United Arab Emirates
- eGrocery/In-Aisle SEO – Strategy, Business Plan, Financial Projections, Go-To-Market Strategy, Sales Collateral – Entrepreneur -USA
- DTC EHealth eMarketplace – Patented fitness kinetic tracking wearable with online social gaming community/rewards platform for exercise motivation and obesity reduction. (Exit to Fitbit)
- DTC B2B and B2B – B2C Procure Office Paper (Japan) with B2B eProcure/eSupply Pulp to Paper Mill (Indonesia to Japan) – Design, Fund – Global Fortune 100 ($10M Finance)
- B2B eProcure – ECommerce (Personal and HomeGoods for Top Brand Hotels) – Venture Backed Startup – Business and Technology Extend, New Strategic Alliance Partner, Wall Street Capital Raising Package ($20M Mezzanine Finance) – USA
- B2B eProcure, ePricing Engine, Content Management System (Digital Publishing) – USA
- DTC B2C Beverages (Wine) – $1Million Direct Equity Investment – Global Fortune 100 – USA
Have Questions?
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Desire to Scope or Accelerate a Project?
Feel free to reach out to discuss how Syl Di Diego would help accelerate your business growth success.
Email Sylvester now to Syl@SylDiDiego.com
Schedule a free 30-Minute Virtual Consult with Syl.
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Learn More
See Syl Di Diego’s Client list.
Review Syl Di Diego’s Client Testimonials.
Visit Syl DiDiego’s Speaker-Trainer page.
Read profile About Syl Di Diego.
See industries served on About Syl Di Diego page.
Schedule with Syl Di Diego.
