VentureRise Mastermind Recap - Nov 5, 2025

Come join us next Wednesday at 10am PT on Zoom for the type of peer advice that you can only get from other VC-backed CEOs who are in the midst of executing large transactions.

Here's what we discussed today.

‍Topic 1: Series B Fundraising Strategy

• Challenges: Preparing for Series B fundraising (~$30M), deciding between self-managing or using investment bankers
• Advice: Use investment bankers for Series B rounds as they deliver better terms (15-25% higher valuations), reduce management distraction, and provide professional process management. The 3-4% cost pays for itself through better outcomes
• Key Takeaway: Investment bankers provide insurance that rounds get completed and help align shareholders

Topic 2: Acquiring a Large Company in an All-Stock Acquisition

• Challenges: Acquiring a $40M revenue company with all-stock deal while managing complex due diligence and process integration
• Advice: Give employees equity/incentives for alignment, maintain local presence, focus on revenue-related KPIs, ensure regular communication, and maintain thorough documentation
• Key Takeaway: Cultural integration requires clear standards, frequent communication, and aligned incentives

Topic 3: Business Exit Strategy

• Challenges: Managing a company exit through merger while positioning against US competitors
• Advice: Professional bankers are more beneficial for exits than for fundraising rounds due to process complexity
• Key Takeaway: Exit processes benefit significantly from professional banker involvement

Topic 4: Sales Forecast Accuracy During Exit Process

• Challenges: Maintaining accurate pipeline forecasting while managing company exit, ensuring realistic closure dates for Q4 deals
• Advice: Make revenue forecasts conservative with 3-5% cushion to exceed expectations rather than fall short. Better to deliver 105% when promising 100% than delivering 105% when promising 120%
• Key Takeaway: Conservative forecasting during M&A processes protects deal terms and valuation expectations

Topic 5: CRO Compensation Structure

• Challenges: Ensuring proper incentive alignment for Chief Revenue Officer managing sales forecasts during exit
• Advice: Discussion on 50-50 variable/fixed compensation structure tied to new ARR achievement targets
• Key Takeaway: CRO incentives should align with realistic pipeline management rather than inflated projections

Topic 6: Finance Department Structure Before Exit

• Challenges: Operating with minimal finance team (CFO and bookkeepers only) for $30M raised company during exit process
• Advice: Typical companies at this stage need four finance roles: CFO, controller, head of FP&A, and bookkeeper. Current structure may be challenging for exit process
• Key Takeaway: Adequate finance infrastructure is crucial for managing complex exit processes and maintaining investor confidence

Topic 7: Work-Life Balance as a VC-Backed CEO

• Challenges: Managing venture-backed company demands while maintaining personal time
• Advice: Implement intentional scheduling (example: 25 hours/week, Monday-Thursday, 11am-4pm for meetings) after building strong business foundation
• Key Takeaway: Intentional life design enables sustainable success across multiple areas