Expertise
Project Financing, PE Origination and Management Consulting
Seasoned Executive with CEO, CMO and CRO Background
20+ Years Experience in Investment, Finance and VC
25+ Years Founder of Multiple Companies with Numerous Exits
Numerous Awards for Multiple Companies including Inc 500 and Inc 5000
Extensive Sales and Marketing Background
Leadership Style
- Values: Integrity, Disciplined Execution, Agility
- Kolbe: 7-3-8-3
- Leadership Style: Leadership is about creating clarity, driving disciplined execution, and unlocking the full potential of people and businesses.
Herb Sih
Managing Director
Herb Sih is an experienced founder, operator, and investor with a proven track record of building, scaling, and exiting companies across multiple industries. He is recognized for his ability to identify undervalued opportunities, implement systems that drive growth, and increase enterprise value through disciplined operational and financial execution.
Herb’s expertise spans sales and marketing strategy, operational efficiency, technology integration, and exit planning. As Managing Partner of R8 Holdings, Herb plays a supporting role to the CEO while contributing on the financial side of the business. He focuses on sourcing capital, managing lender relationships, and assisting with finance-related activities that underpin R8’s acquisition strategy.
After acquisitions, Herb supports portfolio companies through financial oversight, performance tracking, and operational efficiency initiatives. He also contributes a commercial perspective, advising on sales, marketing, and the use of technology — including AI — to increase revenue and reduce costs. This balance of financial stewardship and operational insight complements the CEO’s leadership, helping ensure R8 companies are positioned to grow profitably under professional management.
Select Work Experience
- Cisco (Consultant and B2B Demand Gen Advisor)
- Merrill Lynch (Financial Consultant, Certified Financial Manager CFM)
- Wachovia Securities (Senior VP)
- Think Big Partners (Founder and CEO)
- Think Big Ventures (General Partner, Founder)
- Pioneer Partners (Co-Founder and Senior Partner)
- Clickspeed Marketing (Co-Founder)
- $100M+ Midwest Telecom Co (Consultant and fCMO)
- Honeywell (Digital Transformation Consultant and Advisor for Numerous Cities and Mayors)
- United States Army (Military Pilot, Officer)
- Mach Two (Co-Founder, Senior Consultant)
- Numerous Early Stage Companies (Series A–Series D)
Awards
Numerous awards for multiple companies, including Inc 500 and Inc 5000 recognitions.
