Investors don't just diligence your data room; they diligence your body language. If you and your co-founder hate each other, they know. And it kills the deal.

In this episode of Managed Chaos, host Katrina Purcell wraps up the four-part series on co-founder relationships with Annie Garofalo, founder of Confidante. Drawing on her experience, Annie shifts the lens to show how VCs evaluate the co-founder relationship as an investable asset—not just a nice-to-have.

In this episode, we cover:

• "Relationship-Forward Investors": What does this mean? Why are VCs paying more attention to founder mental health?
• The Pitch: What investors spot in pitch meetings that screams "red flag"—and the 30/30/30 rule.
• The Conscious Uncoupling: If a founder needs to exit, how investors can help guide the separation without destroying equity value.
• Success Stories: What the best co-founding teams do differently.

Memorable Quote: "The co-founder relationship is one of the biggest strengths and one of the biggest risks of a startup company." — Annie Garofalo

🎙️ ABOUT THE GUEST Annie Garofalo (Stanford MBA +MA, Harvard BA) is a leading expert in founder relationships and co-founder conflict, supporting 100+ seed through Series A teams over the past five years. She built research and advisory practice Confidante by fusing entrepreneurship, organizational behavior, and relationship therapy, and works with select VC funds and accelerators (including YC, Flourish, Antler) to support founding teams across their portfolios.

Connect with Annie: https://www.linkedin.com/in/annie-garofalo/

Confidante: https://www.confidante.info/

Partnership agreement program: https://drive.google.com/file/d/1T7XCS9_gmifomvF0QugMaQj2shgZ1fqs/view

Cofounder Mode Cards: https://cofoundermode.io/

Blog / Newsletter on Founding Team Health: https://confidante.substack.com/

Podcast: How I Met My Cofounder: https://podcasts.apple.com/us/podcast/how-i-met-my-co-founder/id1723885564

🚀 ABOUT MANAGED CHAOSManaged Chaos is the podcast for startup founders, COOs, and leaders who are tired of the fluff. We give you the startup business rundown in less time than it takes to get to work. Hosted by Katrina Purcell.

🔗 CONNECT WITH US

Website: www.themanagedchaospodcast.com

LinkedIn: https://www.linkedin.com/in/katrina-purcell/

Instagram: https://www.instagram.com/managedchaospodcast

✨ Special Offer from Pobl.io

Outsourcing your US tech talent should not be hard. With pobl.io you will get high-quality teams on demand and enjoy huge cost savings for your business. Try it now at pobl.io. Mention the amazing Managed Chaos when you email us and get a free market data report.

Loved this episode? Hit the "Follow" button so you don't miss our next episode.

The skills that got you to Seed aren't the skills that get you to Series B. What happens when one founder can scale and the other can't—or doesn't want to?

In this episode of Managed Chaos, host Katrina Purcell continues the four-part series on co-founder relationships with Annie Garofalo, founder of Confidante. This is the most painful conversation—the one about growth gaps, shifting roles, and what happens when the company outgrows one of its founders.In this episode, we cover:

• Why "Co-CEOs" Usually Fail: The only two circumstances Annie has seen it work—and why most teams use it to avoid the hard conversation about who's actually in charge.
• The Performance Plan for Founders: Why founding teams have performance reviews for employees but not for themselves—and how to create a peer-led feedback mechanism.
• Letting Go of Legos: How to transition from "doing everything" to "owning a vertical"—and why it gets worse before it gets better.
• Ego vs. Life: The question every founder needs to answer—do you want your work to fuel your ego or fuel your life?

Memorable Quote: "It's not your co-founder's job to manage you, and it's not your job to manage your co-founder. You are doing this to be peers. So create a system that feels peer led." — Annie Garofalo

🎙️ ABOUT THE GUEST Annie Garofalo (Stanford MBA +MA, Harvard BA) is a leading expert in founder relationships and co-founder conflict, supporting 100+ seed through Series A teams over the past five years. She built research and advisory practice Confidante by fusing entrepreneurship, organizational behavior, and relationship therapy, and works with select VC funds and accelerators (including YC, Flourish, Antler) to support founding teams across their portfolios.

Connect with Annie: https://www.linkedin.com/in/annie-garofalo/

Confidante: https://www.confidante.info/

Partnership agreement program: https://drive.google.com/file/d/1T7XCS9_gmifomvF0QugMaQj2shgZ1fqs/view

Cofounder Mode Cards: https://cofoundermode.io/

Blog / Newsletter on Founding Team Health: https://confidante.substack.com/

Podcast: How I Met My Cofounder: https://podcasts.apple.com/us/podcast/how-i-met-my-co-founder/id1723885564

🚀 ABOUT MANAGED CHAOS

Managed Chaos is the podcast for startup founders, COOs, and leaders who are tired of the fluff. We give you the startup business rundown in less time than it takes to get to work. Hosted by Katrina Purcell.

🔗 CONNECT WITH USWebsite: www.themanagedchaospodcast.com

LinkedIn: https://www.linkedin.com/in/katrina-purcell/

Instagram: https://www.instagram.com/managedchaospodcast

✨ Special Offer from Pobl.io

Outsourcing your US tech talent should not be hard. With pobl.io you will get high-quality teams on demand and enjoy huge cost savings for your business. Try it now at pobl.io. Mention the amazing Managed Chaos when you email us and get a free market data report.

Loved this episode? Hit the "Follow" button so you don't miss our next episode.

If you aren't fighting with your co-founder, you probably aren't being honest. The goal isn't to stop fighting; it's to stop the fight from torching the company.This week, Katrina Purcell and Annie Garofalo continue their four-part series on co-founder relationships. This week, we get tactical. Using Annie's conflict resolution toolkit, we get into the details of how to have difficult conversations with your co-founder without destroying your relationship.In this episode, we cover:

• Healthy vs. Toxic Conflict: How to define what "toxic" means in your dynamic—because what feels like healthy debate to one person might feel like aggression to another.
• The "Safe Word" Protocol: How to operationalize the timeout—establishing a code word to pause heated conversations before they spiral.
• The Danger of Triangulation: Why venting to employees about your co-founder destroys culture—and where founders should vent instead.
• The Speaker-Listener Exercise: A structured weekly check-in format with four questions that create space for appreciation, pinches, existential concerns, and asks for support.
• Neurobiology of Conflict: What happens to a founder's brain under stress—and the one simple hack to repair damage when you inevitably snap.

Memorable Quote: "I can't tell you how many chiefs of staff and early hires come to me and say, 'My co-founders really need you.' That's almost a failure mode—whatever conflict they're having has permeated the team. It's become obvious." — Annie Garofalo🎙️ ABOUT THE GUEST Annie Garofalo (Stanford MBA +MA, Harvard BA) is a leading expert in founder relationships and co-founder conflict, supporting 100+ seed through Series A teams over the past five years. She built research and advisory practice Confidante by fusing entrepreneurship, organizational behavior, and relationship therapy, and works with select VC funds and accelerators (including YC, Flourish, Antler) to support founding teams across their portfolios.Connect with Annie: https://www.linkedin.com/in/annie-garofalo/Confidante: https://www.confidante.info/Partnership agreement program: https://drive.google.com/file/d/1T7XCS9_gmifomvF0QugMaQj2shgZ1fqs/view Cofounder Mode Cards: https://cofoundermode.io/Blog / Newsletter on Founding Team Health: https://confidante.substack.com/Podcast: How I Met My Cofounder: https://podcasts.apple.com/us/podcast/how-i-met-my-co-founder/id1723885564 🚀 ABOUT MANAGED CHAOSManaged Chaos is the podcast for startup founders, COOs, and leaders who are tired of the fluff. We give you the startup business rundown in less time than it takes to get to work. Hosted by Katrina Purcell.🔗 CONNECT WITH USWebsite: www.themanagedchaospodcast.com LinkedIn: https://www.linkedin.com/in/katrina-purcell/ Instagram: https://www.instagram.com/managedchaospodcast✨ Special Offer from Pobl.ioOutsourcing your US tech talent should not be hard. With pobl.io you will get high-quality teams on demand and enjoy huge cost savings for your business. Try it now at pobl.io. Mention the amazing Managed Chaos when you email us and get a free market data report.Loved this episode? Hit the "Follow" button so you don't miss our next episode.

Everyone signs the legal operating agreement. But nobody signs the emotional operating agreement. And that's where the business actually breaks.In this episode of Managed Chaos, host Katrina Purcell kicks off a four-part series on co-founder relationships with Annie Garofalo, founder of Confidante. Annie learned about co-founder conflict the hard way: by starting a company with her best friend of 20 years. They had trust and commitment—but no operating manual for working together. That gap nearly cost them both the business and the friendship.In this episode, we cover:The Honeymoon Phase Trap: Why being best friends is a risk factor—the trust that bonds you can prevent hard conversations.The "Prenup" Questions: What Annie asks teams: "How do we handle it when one of us isn't pulling weight?" "What's our exit number?"The Silent Killer: When one founder wants a lifestyle business and the other wants a unicorn—and neither says it out loud.Your Co-Founder as a Mirror: How to use your co-founder for self-awareness and support in the isolating startup journey.Memorable Quote: "Anytime something feels like me versus you, there's a reframe there for it's actually us versus the problem." — Annie Garofalo🎙️ ABOUT THE GUEST Annie Garofalo (Stanford MBA +MA, Harvard BA) is a leading expert in founder relationships and co-founder conflict, supporting 100+ seed through Series A teams over the past five years. She built research and advisory practice Confidante by fusing entrepreneurship, organizational behavior, and relationship therapy, and works with select VC funds and accelerators (including YC, Flourish, Antler) to support founding teams across their portfolios.Connect with Annie: https://www.linkedin.com/in/annie-garofalo/Confidante: https://www.confidante.info/Partnership agreement program: https://drive.google.com/file/d/1T7XCS9_gmifomvF0QugMaQj2shgZ1fqs/view Cofounder Mode Cards: https://cofoundermode.io/Blog / Newsletter on Founding Team Health: https://confidante.substack.com/Podcast: How I Met My Cofounder: https://podcasts.apple.com/us/podcast/how-i-met-my-co-founder/id1723885564 🚀 ABOUT MANAGED CHAOSManaged Chaos is the podcast for startup founders, COOs, and leaders who are tired of the fluff. We give you the startup business rundown in less time than it takes to get to work. Hosted by Katrina Purcell.🔗 CONNECT WITH USWebsite: www.themanagedchaospodcast.com LinkedIn: https://www.linkedin.com/in/katrina-purcell/ Instagram: https://www.instagram.com/managedchaospodcast✨ Special Offer from Pobl.ioOutsourcing your US tech talent should not be hard. With pobl.io you will get high-quality teams on demand and enjoy huge cost savings for your business. Try it now at pobl.io. Mention the amazing Managed Chaos when you email us and get a free market data report.Loved this episode? Hit the "Follow" button so you don't miss our next episode.

As a founder, you're juggling everything—sales, strategy, team management, and yes, your social media content. You might even enjoy it. But what if the thing you like doing might be the thing holding your business back?In this episode of Managed Chaos, host Katrina Purcell sits down with Emma Tessler (Founder and CEO, Ninety Five Media) to answer a question all founders struggle with: "When do I stop doing this myself?" This episode is about delegation, bottlenecks, and the mindset shift that separates founders who stay stuck from founders who scale.In this episode, we cover:The $25 vs. $500 Task Framework: How to identify which tasks only you can do—and which ones are quietly draining your time.The "Good Enough" Principle: Why perfectionism in marketing creates bottlenecks, and how to train your team without micromanaging every post.The Founder Voice Myth: How to delegate your social media without losing your brand's authenticity (spoiler: it's easier than you think).The Tornado of Growth: What happens when founders stop doing marketing and start doing what only they can do—the business development that actually drives revenue.Memorable Quote: “You are bottlenecking the impact that your brand could make. If your time is on a social media post, you can't be going out there and helping more people and making a bigger change in the world.” — Emma Tessler🎙️ ABOUT THE GUEST Emma Tessler is the Founder and CEO of Ninety Five Media, a social media marketing agency dedicated to creating high converting content for small businesses. With a decade of experience in the marketing world, Emma specializes in turning social media into a powerful tool for growth - helping brands connect with their ideal clients, build engaged communities, and seamlessly convert followers into loyal customers.Connect with Emma: https://ninetyfivemedia.coInstagram: https://www.instagram.com/ninety.five.mediaLinkedIn: https://www.linkedin.com/in/emmatessler/The Stop Scrolling, Start Scaling Podcast: https://podcasts.apple.com/us/podcast/stop-scrolling-start-scaling-podcast/id1635151196🚀 ABOUT MANAGED CHAOSManaged Chaos is the podcast for startup founders, COOs, and leaders who are tired of the fluff. We give you the startup business rundown in less time than it takes to get to work. Hosted by Katrina Purcell.🔗 CONNECT WITH USWebsite: www.themanagedchaospodcast.com LinkedIn: https://www.linkedin.com/in/katrina-purcell/ Instagram: https://www.instagram.com/managedchaospodcast✨ Special Offer from Pobl.ioOutsourcing your US tech talent should not be hard. With pobl.io you will get high-quality teams on demand and enjoy huge cost savings for your business. Try it now at pobl.io. Mention the amazing Managed Chaos when you email us and get a free market data report.Loved this episode? Hit the "Follow" button so you don't miss our next episode.

As a founder, success brings a new problem: Noise. Suddenly, everyone, from your biggest investor to your loudest customer to your own sales team, has an opinion on what you should build next.

In this episode of Managed Chaos, host Katrina Purcell wraps up our four-part masterclass on Customer Intelligence with Guest in Residence, Glenn Perera (Perera Insights).

We’ve covered how to collect feedback (VOC), how to organize it (CABs), and how to plan with it (JBP). Now, we tackle the hardest leadership challenge of all: How to say "No."

This episode is about Radical Prioritization—how to filter the flood of requests so you don't turn your strategic roadmap into a chaotic wish list.

In this episode, we cover:

• The Mission Filter: How to use your company’s core values as a scoring system to objectively disqualify bad feedback.
  

• The Sandbox Rule: A framework that gives your team 10% of their capacity to work on "wild ideas" so they don't derail the main roadmap.

• Internal Noise: How to stop your sales team from selling features that don't exist (and how to get them to champion the actual roadmap).
  

• When to Do What Doesn't Scale: Why building a custom one-off feature is sometimes the right strategic move, even if it breaks the rules.

Memorable Quote: "You have to have the discipline to say: 'I’ll call your baby ugly, but I’ll tell you why and how we can make it look less ugly.'" — Glenn Perera

🎙️ ABOUT THE GUEST Glenn Perera is the founder of Perera Insights and a veteran in customer intelligence. He specializes in turning messy, raw customer data into clear, actionable business strategies. He helps founders move beyond gut feelings to build products that customers actually need.

Connect with Glenn: https://www.linkedin.com/in/glennperera/ Perera Insights: https://pererainsights.com/

• 🚀 ABOUT MANAGED CHAOS

• Managed Chaos is the podcast for startup founders, COOs, and leaders who are tired of the fluff. We give you the startup business rundown in less time than it takes to get to work. Hosted by Katrina Purcell.

• 🔗 CONNECT WITH US

• Website: www.themanagedchaospodcast.com LinkedIn: https://www.linkedin.com/in/katrina-purcell/ Instagram: https://www.instagram.com/managedchaospodcast

• ✨ Special Offer from Pobl.io

• Outsourcing your US tech talent should not be hard. With pobl.io you will get high-quality teams on demand and enjoy huge cost savings for your business. Try it now at pobl.io. Mention the amazing Managed Chaos when you email us and get a free market data report.

Loved this episode? Hit the "Follow" button so you don't miss our next episode.

Stop Doing QBRs: Why Joint Business Planning Wins Deals

Does the calendar invite for a "Quarterly Business Review" make you dread the next hour? You aren’t alone. Most QBRs are nothing more than "Death by PowerPoint"—looking backward at data you can’t change and defending why you missed a number.

In Part 3 of our Customer Intelligence arc, host Katrina Purcell and Guest in Residence Glenn Perera (Perera Insights) explain why you need to stop interrogating your clients and start co-creating with them.

We break down the shift from the backward-looking QBR to the forward-looking Joint Business Planning (JBP) session—a strategy that turns you from a vendor into a strategic partner.

In this episode, we cover:

• The "Interrogation" Trap: Why traditional QBRs feel like a trial, and how to change the dynamic by "sitting on the same side of the table."

• The "Pre-Read" Rule: One simple email tactic that saves you 45 minutes of meeting time and eliminates the bore of reciting metrics.

• The "3 Crazy Ideas" Pitch: How to end every meeting with energy by pitching wild, creative ideas instead of just reporting status.

• The Human KPI: Why helping your contact get a promotion is the ultimate retention strategy.

Memorable Quote: "A QBR is looking in the rearview mirror to justify the past. Joint Business Planning is sitting next to each other to pick the destination." — Glenn Perera

🎙️ ABOUT THE GUEST Glenn Perera is the founder of Perera Insights and a veteran in customer intelligence. He specializes in turning messy, raw customer data into clear, actionable business strategies. He helps founders move beyond gut feelings to build products that customers actually need.

Connect with Glenn: https://www.linkedin.com/in/glennperera/ Perera Insights: https://pererainsights.com/

🚀 ABOUT MANAGED CHAOS

• Outsourcing your US tech talent should not be hard. With pobl.io you will get high-quality teams on demand and enjoy huge cost savings for your business. Try it now at pobl.io. Mention the amazing Managed Chaos when you email us and get a free market data report.

Loved this episode? Hit the "Follow" button so you don't miss our next episode, where we discuss how to filter all this new feedback without destroying your product roadmap.

Most companies treat their Customer Advisory Board like a high-end dinner party or a one-way press tour. If you spend your entire CAB talking at your customers, you are missing the single greatest opportunity to stress test your GTM strategy.

In this episode, Katrina Purcell and Guest in Residence Glenn Perera from Perera Insights break down how to move past the razzle dazzle and turn your CAB into a strategic growth engine.

CHAPTERS

00:00 The Razzle Dazzle Trap: Why CABs fail

04:15 Selection Strategy: Finding your visionaries and skeptics

09:30 Virtual vs In-Person: The magic number for engagement

10:00 The Rabbit Hole Rule: Practical tactics for meeting control

14:00 The N-Customer Rule: Radical prioritization of feedback

15:00 Action and Accountability: Closing the loop with clients

🎙️ ABOUT THE GUEST Glenn Perera is the founder of Perera Insights and a veteran in customer intelligence. He specializes in turning messy, raw customer data into clear, actionable business strategies. He helps founders move beyond gut feelings to build products that customers actually need.

Connect with Glenn: https://www.linkedin.com/in/glennperera/ Perera Insights: https://pererainsights.com/

🚀 ABOUT MANAGED CHAOS

Managed Chaos is the podcast for startup founders, COOs, and leaders who are tired of the fluff. We give you the startup business rundown in less time than it takes to get to work. Hosted by Katrina Purcell.

🔗 CONNECT WITH US

Website: www.themanagedchaospodcast.com

LinkedIn: https://www.linkedin.com/in/katrina-purcell/

Instagram: https://www.instagram.com/managedchaospodcast

✨ Special Offer from Pobl.io

Outsourcing your US tech talent should not be hard. With pobl.io you will get high-quality teams on demand and enjoy huge cost savings for your business. Try it now at pobl.io. Mention the amazing Managed Chaos when you email us and get a free market data report.

📧 Contact: [email protected]

Listen and Subscribe: If you enjoyed this episode, please subscribe and leave a 5-star review. It helps us reach more founders and leaders looking to manage the chaos of growth.

You don’t have a business if you don’t have a customer. Yet, so many founders fall into the trap of being "vision-led" rather than listening to the people actually paying the bills.

In the Season 3 premiere of Managed Chaos, hosts Katrina Purcell and Rachel Anderson kick off a special four-part arc on Customer Intelligence. We are joined by our Guest in Residence, Glenn Perera (Pereira Insights), an expert in turning raw, chaotic customer data into clear, actionable strategy.

If you are drowning in support tickets, conflicting feature requests, or vague survey data, this episode provides the framework you need to clear the noise.

In this episode, we cover:

• 
  

  The "Buyer vs. User" Trap: Why the person signing the contract often gives you the wrong feedback—and who you should be listening to instead.

  
  

• 
  

  The VOC Framework: How to use your company’s Mission, Vision, and Values to filter feedback and decide what actually gets built.

  
  

• 
  

  Radical Prioritization: A workshop technique to force your team (and customers) to cut their wish lists by 30% or more.

  
  

• 
  

  Why Churn is Too Late: Why looking at churn data is looking in the rearview mirror, and how to spot issues before they leave.

  
  

Memorable Quote:"There always comes a time where your customers know your product and the problem better than you." — Glenn Perera

Links & Resources:

• 🎙️ ABOUT THE GUEST: Glenn Perera is the founder of Perera Insights and a veteran in customer intelligence. He specializes in turning messy, raw customer data into clear, actionable business strategies. He helps founders move beyond "gut feelings" to build products that customers actually need.Connect with Glenn: https://www.linkedin.com/in/glennperera/Perera Insights: https://pererainsights.com/🚀 ABOUT MANAGED CHAOS: Managed Chaos is the podcast for startup founders, COOs, and leaders who are tired of the fluff. We give you the startup business rundown in less time than it takes to get to work. Hosted by Katrina Purcell and Rachel Brenke.🔗 CONNECT WITH US:Website: www.themanagedchaospodcast.comLinkedIn: https://www.linkedin.com/in/katrina-purcell/Instagram: https://www.instagram.com/managedchaospodcast

Loved this episode?Hit the "Follow" button so you don't miss Part 2 of our Customer Intelligence Arc, where we break down how to run a Customer Advisory Board without wasting everyone's time.

We’ve officially entered circle back season,  that magical time of year when calendars are full, inboxes are louder than ever, and everyone is mentally halfway into next year already.

In this special end-of-year episode, Katrina and Rachel reflect on wrapping up 2025, share a few laughs about December chaos, and pull back the curtain on what’s coming next for the Managed Chaos Podcast.

Season 3 officially launches January 21, 2026, sticking with the same Wednesday cadence and 15-minute, jam-packed episode, just with some fresh twists and new voices.

Whether you’re closing out the year strong or already manifesting your 2026 plans, this episode is equal parts reflection, humor, and momentum to help you move forward with intention.

As always, we give you the startup business rundown in less time than it takes for you to get to work.

🔗 Connect with Katrina Purcell:
https://www.linkedin.com/in/katrina-purcell/

🎧 Subscribe for Season 3 updates, guest announcements, and new formatscoming in 2026.