Why Your Project Management System Is Failing You—and How to Fix It with Natalie Gregorian
Description
Ernesto sits down with ClickUp strategist and Tiptop Ops founder Natalie Gregorian to unpack the hidden costs of disorganized operations—and how to fix them with scalable systems. With over 10,000 hours of ClickUp mastery, Natalie reveals how she helps overwhelmed CEOs and business owners transition from reactive chaos to structured growth using smart hierarchy design, automation, and actionable dashboards. Whether you're drowning in overdue tasks or stuck micromanaging your team, this episode lays out the exact path to reclaim your time, streamline your workflows, and scale your business—without needing to be a tech expert.
Chapters:
- 00:00:00 - Systems Start at the Top
- 00:01:32 - Welcome to Momentum Multipliers
- 00:01:38 - Meet Natalie: Your Systems Whisperer
- 00:03:22 - From Home Chaos to Business Flow
- 00:04:35 - The ClickUp Confession Booth
- 00:06:10 - ClickUp Hierarchy Made Easy
- 00:08:40 - Auditing the Chaos, Designing the Fix
- 00:11:14 - Building a System That Runs Without You
- 00:18:32 - Real Clients, Real Results
- 00:21:11 - The Human Side of Natalie
- 00:22:41 - Ready to Systemize? Here’s How
- 00:23:49 - Final Thoughts & Your Next Step
Links and Resources:
- Tip Top Ops Website
- Natalie Gregorian on LinkedIn
- Design your Growth Strategy
- Ernesto Mandowsky on LinkedIn
- MDM Website
Thanks so much for joining us this week. Want to subscribe to the Momentum Multipliers Podcast? Have some feedback you’d like to share? Connect with us on Spotify, Apple Podcasts and YouTube to leave us a review!













