How do I clean up a shitty cofounder relationship? w/ Ryan Vaughn

How do I? with Matt Putra

Episode Overview

This episode tackles one of the most critical challenges in startup leadership: repairing damaged co-founder relationships. Ryan Vaughn, executive coach and founder of Inside Out Leadership, brings his experience as a 3x serial entrepreneur and coach to over 100 founders worth $10+ billion in equity value. Having navigated co-founder tensions in each of his three companies, Ryan shares his proven "Clearing Conversation Framework" - a simple but challenging 3-step process that eliminates relational debt and restores open communication between business partners.

Ryan Explains

• What relational "cruft" is and why it inevitably builds up between co-founders over time
• How withholding small grievances creates communication debt that destroys business performance
• The "speaking inarguably" technique to present facts without triggering defensiveness
• Why taking 100% responsibility is the key to unlocking change and preventing blame cycles
• How to identify your role in creating dysfunction using the "adjunct professor" exercise
• The complete 3-step Clearing Conversation Framework for rebuilding co-founder trust

Timestamps

00:53 - Introduction and audio setup discussion

01:46 - Hampton community background and revenue criteria

03:09 - Co-founder relationship challenges overview

05:51 - Matt's podcast evolution and format

07:14 - Ryan's multi-faceted co-founder experience

08:22 - Defining relational "cruft" and communication debt

10:02 - Marriage comparison and inevitable relationship buildup

12:00 - Three-step clearing conversation framework introduction

13:18 - Step 1: Observing what's true

15:36 - Speaking inarguably technique explained

16:10 - Emotional literacy for leaders discussion

17:33 - Step 2A: Taking 100% responsibility

20:19 - The adjunct professor thought experiment

21:08 - Ego resistance to taking responsibility

23:38 - Step 2B: Acknowledging impact on others

25:23 - Step 3: Making commitments for change

25:53 - Why no apology is required

28:33 - Framework frequency and maintenance

30:07 - Implementation success rates and outcomes

31:34 - Inside Out Leadership introduction and contact

Follow Ryan Vaughn:

Website: leadinsideout.io

LinkedIn: linkedin.com/in/ryanhvaughn

About Ryan's Company

Inside Out Leadership is a boutique executive coaching firm staffed entirely by post-exit founders who have transitioned into coaching. Founded by Ryan Vaughn after scaling and exiting VNN (a media company), the firm specializes in helping founders transform their companies into their masterpieces while stepping fully into their lives. Ryan's unique background includes founding and serving as CEO of three companies over 15 years, with experience raising venture capital, scaling operations, and navigating complex co-founder dynamics. The firm focuses on the personal growth process of startup leadership, working with founders at all scales on both individual development and organizational transformation.

About How Do I?

The How Do I? Podcast gives you 60 minutes with industry experts who teach their expertise to eCommerce founders and business operators. Each episode centers on a single "How do I...?" question, providing actionable tactics you can implement immediately.

Host: Matt Putra, Founder & CEO of Eightx

Our Sponsors

Eightx helps eCommerce, CPG, and SaaS companies scale profitably with expert CFO services and financial architecture. Founded by Matt Putra, Eightx specializes in cash flow optimization, financial planning, and strategic growth guidance for businesses between $5-80MM in annual revenue or venture-backed companies. Their team of experienced CFOs provides the knowledge and proven strategies that make scaling, growing, and lasting effortless.

Services include:

• Fractional CFO and financial leadership
• Cash flow management and optimization
• Strategic financial planning and forecasting
• Marketing ROI analysis and optimization
• Operational efficiency improvements

Website - eightx.co