Today's Edition

• Pando: Honest Founder Dialogues

• Transform 2025 Discount Code

🗣️Pando: Honest Founder Dialogues

This past Tuesday, 10/8, I attended (along with my colleague, Chelsea) & sponsored an event hosted by Pando, in collaboration with Sequoia One PEO for SF Tech Week.

Led by Ines Gramegna & Charlie Olson, Pando hosted an intimate evening curated specifically for founders who have raised <$5m in Seed, Series A, and Series B in the last 3 years for an night of authentic and vulnerable discussions. The event, held in a beautiful loft located in the Marina District of San Francisco, was a testament to the power of community and shared experiences among those who lead at the highest levels.

The Purpose:

The conversations were designed to foster deep, meaningful conversations among founders. Founders were split into two separate “peer discussion groups,” each with a dedicated facilitator with founder experience to lead the discussions. I’d like to mention that while I attended the event, I didn’t participate in the peer groups, in an effort to preserve the feeling of safety among founders.

Focusing on their journeys, motivations, and the unique challenges they face, attendees shared personal stories about their own paths, revealing the diverse motivations and experiences that shape their leadership styles. At the end of the day, real connections were formed. There were no investors, board members, team members, or customers in the room - founders could really just be themselves.

Key Topics of Discussion

1. Hustle Culture: The long-hours & sacrifice of major startup icons has been well-documented and romanticized within culture. Is this a positive or negative for founders? Realizing that preventing burnout isn’t just good for the individual, but for the general wellbeing of the team is important. Understanding that sacrifice doesn’t have to be at the detriment of one’s own health/wellbeing is key to finding a balance. So how do you do that?

2. Defining Success: Is success reaching a financial milestone like another round of fundraising or an exit? Or is it providing growth opportunities for their people & talent? There is no right answer, and each founder was encouraged to share what how they define “success” themselves.

3. Managing Executive Compensation and Pay: Founders discussed the complexities of executive compensation, how to pay themselves, even how to approach the board to request a wage increase. This is a major moral conundrum for many: how do I pay myself enough to live comfortably & maintain a level of wellbeing that allows me to lead at this level without inversely affecting the company or employee perception?

4. Humbling Moments: Leading a company inherently comes with major decisions & living with their results. Founders opened up about the pressures they face, from maintaining work-life balance to making high-stakes hiring & firing choices. These candid discussions fostered a sense of solidarity and shared understanding among attendees.

About Pando:

Pando offers a one-stop-shop for founders to get the peer community and support they need to be successful. Pando matches you with a cohort of 8-10 impressive founders interested in building enduring relationships with brilliant and ambitious peers.

They have a network of 300+ extraordinary founders, who have raised from 750+ unique investors. Their founders have raised $3.6B, and run companies valued at ~$8B.

Special thanks:

I want to shout out the amazing team at Pando, specifically Ines, Charlie, Chase, and Colin. Every detail of the event was carefully planned and thoughtfully executed, and it’s clear that the founders who participate in the community gain tremendous value & support by doing so. I encourage any founder reading this to reach out & learn more about their growing network.

⭐️Transform 2025 Discount Code

Transform 2025 is the premier gathering of business leaders, investors, and entrepreneurs focused on transforming the now and next of work for the better.

Come join me to learn, get inspired, and connect with your peers. We’re taking bets on who this year’s performer is going to be after shows from FloRida, Ludacris, and Nelly… 👀 

I’m lucky enough to have a discounted partner link that offers $200 off the normal ticket price!

Register now with my partner link to secure the lowest pricing:

Thank you for reading and joining on this journey with me!

Please reach out with any feedback about future topics you’d like to read about.

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👋 Quick about me:

I’m Cris Cafiero, and for nearly a decade, I’ve collaborated with founders, CFOs, and people leaders of early-stage, venture-backed startups. As an ex-Zenefits, ex-ADP, and now Business Consultant for Sequoia, I help startups build scalable people management infrastructure and maximize their people investment through compensation & benefits strategies.

Based in LA, I share my life with my wife and our two dogs. I’m into NBA drama, Marvel, reading, video games, computer-building, real estate investing, and lifelong learning.

I care about helping startups build a thoughtful, people-first culture and hope you find the topic as interesting as I do.

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