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Sylvester (Syl) Di Diego
Strategist – Analyst – Facilitator
Are you driven to innovate, launch a product or technology, raise capital, or to grow your markets, profits, or ROI? Do you need to scale, pivot, or turnaround? Do you have an urgent priority? Would you benefit from Syl’s imagination and tool kit to achieve your goals? Then let’s talk!
Sylvester (Syl) Di Diego enables entrepreneurs, executives, investors, and owners to gain momentum and overcome obstacles for more success. His roles include Strategist, Analyst, Advisor, Fixer, and Agile Facilitator. Syl leverages his A to Z experience especially guiding and leading champions to overcome key growth points in the venture, business, and digital lifecycles. He serves on both sides of the investor table and is active from the huddle, factory, and port to the Board Room.
Industries Served:
• Food & Beverage
• Biotech – Medical Devices – Wellness
• Advanced Manufacturing & Engineering
• Digital – Technology – Transformation
• Accelerators – Incubators – Venture Studios
• Venture Capital – Private Equity
• Procurement – Logistics – Supply Chain
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, Transformation & Financing Achieved:
• 10+ Ecommerce Platforms (including $10M & $20M raised)
• 10 Websites (conceive-design-finance-oversee) Up to $5M budget each.
• 5 Transformations (corporates and ventures)
• 4 SaaS Platforms (ventures)
• 2 Apps (ventures)
Sylvester Di Diego is based in Greater Houston, Texas (Cinco Ranch, Katy) USA and works remotely with clients across the USA and Globe.
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 finance and partnering, and for operations scaling and exit. As successful outcomes are achieved, the relationship often expands as clients call upon Syl as a trusted resource to further assist with their evolving needs and priorities.
Why Syl? The Value Proposition. By leveraging his extensive track record, relationships, 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. As relevant, Syl leads your teams or assembles and leads his curated teams of specialists to suit the specific mission.
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Advisor, Coach, & Consulting 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, crisis resolution, project resets, 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)
- Small Business Owners
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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.
Programs Created and Delivered for Accelerators – Incubators:
- Accelerator – State EDA Sponsored Commercialization Innovation Center Program. Concept through Delivery. (4 years, 80 ventures served)
- Incubator State University Sponsored Services. Entrepreneur-In-Residence (4 years, 60 ventures served)
- Venture Catalyst Program for Global Fortune 100 concept through Delivery (18 months, all industry groups served)
- Incubator Fund Manager for Global Fortune 100 (2 years, 7 countries)
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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 hands-on roles of web conceive, design, development, test, launch, operate, fulfillment, and customer service. 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.
Projects:
- eCommerce Stores
Wine, Food, Beverages, Medical Devices, ePropTech - SaaS Platforms
eGrocery/Mobile Shopping, eFitness/Wearable, Text-to-Speech, ePublishing, eProcurement (hotel supplies), Pulp to Deskside Copy Paper - eOutsourcing Just-In-Time Platform
Global Semiconductor Memory-Fab-ASIC (electronic materials, gases, chemicals, machine parts | order to cash to JIT Delivery - Countries
United States of America, Canada, United Kingdom, Japan, India, United Arab Emirates (UAE)
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 Client Testimonials. about Syl Di Diego.
Have Questions?
Seeking to schedule a Consult?
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.
Visit contact page for more ways to contact or network with Syl.
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.
