Guest: Katherine von Jan, Founder & CEO of Tough Day

Date: June 05, 2025

Key Takeaways

• Tough Day helps employees and managers work through workplace challenges via a private, AI-powered chat assistant called Tuffy.
• Tuffy assists with performance conversations, feedback collection, roleplay, journaling, and decision-making—all within a confidential interface.
• Built on curated HR, legal, and leadership frameworks not available in public LLMs, including HBR content and partner-authored materials.
• Customizes tone and recommendations to match regional and organizational culture.
• New subscriptions available directly via Tough.Day, including individual and small team plans.

Frameworks & Concepts

• Confidential Coaching: Private, personal-device access; no data returned to employer.
• Manager Support: Use Tuffy for performance reviews, managing up, and preparing tough conversations.
• Customization Layer: Employers define HR policy stances; tone adapted for cultural fit.

Resources

• Tough.Day (Official Site)
• Katherine von Jan on LinkedIn
• Fisher Phillips Employment Law
• Harvard Business Review
• Charter Works
• Perplexity.ai
• Vibes.AI
• OpenAI

Chris Pitchford, Founder of Brev

Summary:

Chris Pitchford joins Ryan Estes to explore how AI agents are reshaping business execution. Brev embeds AI directly into enterprise workflows to automate status tracking, identify risks, and align teams across OKRs—all without logging into new tools. Chris breaks down his startup journey, enterprise go-to-market playbook, and vision for a future where agents and humans work side-by-side.

Key Takeaways:

• AI agents automate execution—not just status reports
• Weekly check-ins drive 2.5x more goal achievement
• Design partner process was cold, rigorous, and legally binding
• Predictable pricing is key for enterprise adoption
• Brev’s real moat is data and embedded workflows, not just the model

Frameworks:

• Brev Agent Model: Listen → Track → Flag → Update
• Design Partner Funnel: Outreach → Interview → Contract → Feedback
• Pricing Validation: Ask “cheap” vs “prohibitively expensive” to find the middle ground

Resources:

• Brev.ai
• The Mom Test
• First Round Capital Playbooks
• Granola AI
• Product Hunt - Brev Launch

Connect with Chris Pitchford:

LinkedIn

Nicole Donnelly, Founder of AISmartMarketing.com

Overview:

Nicole is a former pro snowboarder turned AI strategist, now helping businesses of all sizes adopt practical, impactful AI tools. In this conversation, she explains how AI can help small businesses scale, survive economic shifts, and automate without losing their human touch.

Key Takeaways:

• 75% of small businesses haven’t adopted AI yet—major opportunity.
• Google search volume is down for the first time ever—AI search is rising.
• AI is the bridge through the $1M and $10M growth “valleys of death.”
• Use case: AI agent built to forecast sales based on seasonal weather patterns.
• Gemini excels in math; ChatGPT delivers better insights.
• AI + automation = more creativity and happier teams.

Frameworks & Methodologies:

4D Framework:

1. Diagnose – Audit existing processes
2. Design – Create an AI strategy
3. Develop – Train and test tools
4. Deploy – Scale intelligently

Training Ladder:

• $197 self-serve course
• $997 live course (4 weeks)
• $5,000+ certification programs
• $10K+/day in-person training

Resources:

• AI Smart Marketing Website
• Courses and Resources
• YouTube Channel
• Go High Level CRM
• Farmers Almanac