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Top 10 founder challenges

PRICING

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BASIC

Retainer 
USD $1,200/month
Minimum 6 months
Cancel anytime for any reason

Access
Email support

Response Time
Within 48 hours on business days

Coaching Sessions
1 x 90-minute Zoom call per month

Typical Focus Areas

  • Prioritization of key startup challenges, i. e. fundraising, sales, go-to-market etc.

  • Tactical advice on product-market fit, hiring, or scaling strategies

  • Accountability check-ins on progress

  • Foundational mental health and emotional resilience tips for founders

Extras

Private Member section with meeting notes in chronological Startup Journal, curated resources, templates, and HAPPY FOUNDER book

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PREMIUM

Retainer 
USD $3,000/month
Minimum 6 months
Cancel anytime for any reason

Access

Email and phone support

Response Time

Within 24 hours on business days

Coaching Sessions

4 x 60-minute Zoom calls per month

Typical Focus Areas

  • In-depth strategy for scaling and growth

  • Team culture development and leadership coaching

  • Fundraising strategy, pitch deck reviews, and investor relations advice

  • Personal growth, mental resilience, and founder well-being

Extras

Private Member section with meeting notes in chronological Startup Journal, curated resources, templates, and HAPPY FOUNDER books for team.

Access to priority resources, private Slack or WhatsApp group for ongoing support.

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VIP

Retainer 
USD $6,000/month
Minimum 6 months
Cancel anytime for any reason

Access

Email, direct phone, text, and video support (including emergencies)

Response Time

Within 12 hours, including weekends for urgent matters

Coaching Sessions

4 x 30-minute plus 4 x 60-minute Zoom calls per month (or as needed)

Typical Focus Areas

  • Acting as a sounding board for critical CEO decisions

  • Leadership development and team management strategies

  • Detailed fundraising support, including investor meetings and term sheet negotiations

  • Ongoing mental health support, stress management, and work-life balance coaching

  • High-touch strategic planning, with a focus on long-term goals, personal growth, and key business decisions

Extras

Private Member section with meeting notes in chronological Startup Journal, curated resources, templates, and HAPPY FOUNDER books for team.

Access to priority resources, private Slack or WhatsApp group for ongoing support.

Quarterly performance reviews with actionable recommendations, VIP access to all events and workshops, and personalized business audits as required.

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CUSTOM

Pricing TBD based on scope

This option is for founders with highly specific needs that don't fit into the predefined tiers.

 

The Custom Retainer provides a fully personalized coaching plan, where every aspect of support is adapted to your goals, challenges, and schedule.

 

This level might include

  • Bespoke Coaching Sessions: Tailored session lengths, frequencies, and formats (e.g., Zoom, in-person, or on-site).

  • Fully Customized Focus Areas: Whether it’s deep-dive strategy for scaling, hands-on help with product management, crisis resolution, or building investor relationships, each coaching session is designed around your immediate priorities.

  • Specialized Access: As-needed support, emergency access, or project-based check-ins depending on the intensity of your business needs.

  • Exclusive Resources: Personalized performance audits, team workshops, and direct access to your coach for ongoing input and collaboration.

  • On-Demand Support: Flexible response times, potentially including weekend availability and instant messaging for urgent matters.

Suitable For

  • Founders with complex, evolving challenges that require an agile, hands-on approach.

  • Businesses in high-growth phases needing specific guidance not covered in traditional coaching packages.

  • Leaders who want to balance strategic coaching with tactical execution assistance.

  • This option is best for founders looking for a more hands-on partnership with a coach, and pricing can be adjusted based on the scope of support and frequency of touchpoints.

Lack of Funding | Achieving Product-Market Fit | Running Out of Money
Recommendation: VIP/Co-CEO Retainer

High-frequency support is necessary to refine product-market fit strategies while managing the fundraising process and avoiding the risk of running out of cash. The VIP retainer provides the immediate feedback and strategic planning required.

Long Hours with Slow Progress | Building a Scalable Business | Competition Overtaking You
Recommendation: Premium Retainer

Regular coaching helps you break through plateaus, find efficient scaling solutions, and outpace the competition. The Premium retainer offers enough support to stay focused on growth while preventing burnout.

Difficulty Hiring the Right Talent | Creating a High-Performing Team | Losing Key Team Members

Recommendation: VIP/Co-CEO Retainer

Managing team dynamics and recruitment while avoiding turnover is critical. The VIP retainer provides ongoing, personalized coaching to ensure talent acquisition aligns with company goals and team cohesion remains strong.

Managing Investor Expectations | Gaining Investor Trust and Support | Failing to Meet Investor Expectations

Recommendation: VIP/Co-CEO Retainer

Given the high stakes of managing investor relations, frequent, hands-on guidance is needed to maintain trust, meet expectations, and secure further investment rounds. The VIP package is ideal for this kind of detailed, real-time support.

Uncertainty in Decision-Making | Clarity in Direction and Strategy | Making the Wrong Strategic Decisions
Recommendation: Premium Retainer

Regular sessions provide the clarity and strategic insight needed to make confident decisions. The Premium retainer offers enough frequent touchpoints for you to course-correct and refine their strategies.

Poor Work-Life Balance | Finding Balance While Growing the Company | Burnout or Mental Health Struggles

Recommendation: Premium Retainer

Coaching focused on balance, well-being, and mental health requires regular support. The Premium package is designed to guide you through maintaining balance while your business grows, helping prevent burnout.

Customer Acquisition Challenges | Rapid User Growth | Losing Customers to Competitors

Recommendation: Premium Retainer

The Premium retainer is ideal for navigating marketing strategies, user acquisition, and retention to ensure sustainable customer growth while keeping up with competitors.

Lack of Clear Market Differentiation | Standing Out in a Crowded Market | Becoming Irrelevant or Outdated

Recommendation: Premium Retainer

Differentiation and branding strategies require consistent refinement, and the Premium retainer offers enough regular sessions to fine-tune positioning and keep the business relevant.

Constant Firefighting | Stability and Smooth Operations | Business Collapse Due to Unforeseen Crises

Recommendation: VIP/Co-CEO Retainer

For businesses facing constant operational crises, the VIP/Co-CEO retainer provides on-demand support to address emergencies and implement strategies for stability and long-term operational smoothness.

Tech Challenges Slowing Development | Seamless, Fast Development Processes | Product Failure or Bugs Damaging Reputation

Recommendation: Premium Retainer

With the need to address ongoing development hurdles and ensure product quality, the Premium retainer gives enough consistent coaching to optimize processes and avoid tech issues damaging the brand.

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