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

Guest: Benjamin Johnson, CEO of Particle41

Episode Summary: Benjamin Johnson shares how Particle41 helps companies move from AI experimentation to full agentic automation using a Bronze–Silver–Gold framework. He unpacks the societal, ethical, and practical implications of large language models, AI-generated relationships, and AI's role in modern recruiting and marketing operations.

• AI relationships may disrupt emotional development in future generations.
• AI tools enhance creativity in business but can strip away emotional authenticity.
• Bronze–Silver–Gold AI framework helps companies implement AI gradually and responsibly.
• Over-regulation benefits big tech incumbents and can stifle innovation.
• AI agents are already being used in recruiting, support, and proposal creation.

• Particle41 Website
• Gamma for AI Presentations
• Claude by Anthropic
• Read.ai Transcription Tool
• HubSpot CRM
• Colorado School of Mines Athletics

To connect directly with Benjamin or learn more about Particle41's AI consulting services, visit particle41.com.

Guest: Aaron Painter, CEO of GetNametag.com

Episode Overview

Aaron Painter joins the show to explore the urgent need for identity verification in the age of generative AI and deepfakes. As CEO of GetNametag.com, Aaron outlines how mobile-based authentication can protect businesses and individuals from cyber threats, account takeovers, and AI impersonation scams.

Key Takeaways

• Deepfake Threats: AI-generated impersonations are rapidly evolving, posing real risks to businesses and people.
• Outdated Security Methods: Security questions and SMS verification are insufficient in today’s threat landscape.
• NameTag’s Mobile Innovation: Combining ID scanning, facial mapping, and mobile phone data for secure identity verification.
• Enterprise Applications: Used by HubSpot, Autodesk, and others to verify employees and users during onboarding and support interactions.
• AI vs Trust: As AI lowers the cost of deception, Aaron argues that trust must become the new digital currency.

Frameworks

• Identity Verification: ID scan → 3D selfie → phone-based security
• Helpdesk Flow: One-tap verification links to minimize friction
• Reusability Loop: Users can re-verify with a single selfie after first use

Resources

• GetNametag.com – Aaron's company
• Aaron Painter on LinkedIn
• WhisperFlow – AI voice tool
• Claude 4 by Anthropic
• Google Veo
• Tetragrammaton with Rick Rubin

Guest: Mariana Padilla, Founder & CEO of Hackerverse.ai

Summary: Mariana shares how Hackerverse is turning cybersecurity sales into hands-on, testable experiences for buyers. From "World Hacker Games" to instant, AI-generated product demos, Mariana explains how she and her team are slashing POC timelines, building trust through transparency, and creating a community-led growth engine in an industry known for skepticism. She also talks about her unique journey, advice for startup founders, and the looming risks of agentic AI warfare.

Key Takeaways

• Storytelling is critical in technical sales: “Words are our code.”
• Buyers can test software in digital replicas of their own systems—no sales call needed.
• Red team “World Hacker Games” offer real-time validation of cybersecurity products.
• Using generative and agentic AI, Hackerverse can launch vendor POCs in hours.
• Community-building through Discord, immersive branding, and real relationships is core to Hackerverse’s success.

Frameworks & Models

• Digital POC Framework: Self-service product trials in simulated environments.
• Community-Led Growth: Build rabid fans through radical transparency and engaging experiences.
• Beginner’s Mindset: Embrace naivety as a strength when entering technical industries.

Resources

• Hackerverse.ai
• Mariana’s LinkedIn
• Techstars Chicago AI
• OWASP Foundation
• Lydia – Deepfake Detection
• Book: Zen Mind, Beginner’s Mind by Shunryu Suzuki

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Guest: Charles Maddock, Co-Founder of Strawberry Browser

Host: Ryan

Episode Overview

In this episode, we delve into the innovative world of Strawberry, an AI-powered browser designed to automate repetitive tasks and enhance productivity. Charles Maddock shares insights into how Strawberry's AI companions learn from user behavior to streamline workflows, from managing emails to conducting research.

Key Takeaways

• AI Companions: Strawberry introduces AI assistants that learn from your actions, automating tasks like data entry, email management, and research.
• User-Centric Design: Emphasis on intuitive interfaces, such as the "glowing button," to simplify user interaction with AI features.
• Privacy and Control: Users maintain control over their data, with options to approve AI actions and assurances about data handling.
• Customization: Users can teach companions specific tasks, tailoring the browser to individual workflows without coding.
• Productivity Boost: Strawberry aims to save users up to 18 hours per week by automating routine tasks.

• 
  

Frameworks and Concepts

• Agentic Browsing: The concept of AI agents operating within the browser to perform tasks autonomously.
• Human-AI Collaboration: Viewing AI companions as team members that assist with tasks, enhancing human productivity.
• Adaptive Learning: AI companions learn from user behavior to provide personalized assistance over time.

Resources and Links

• Strawberry Official Website
• Strawberry on Product Hunt
• Strawberry LinkedIn Page
• Strawberry AI Browser Review
• Strawberry Use Cases

• 
  

• 
  

• __

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  Subscribe to the newsletter ⁠here⁠, for AI news, tools, and exclusive promos for founders.