Founders Interviews: Gregory Stoos of Planless

“Building a startup is a rollercoaster.”

Indico Capital Partners
3 min readFeb 4, 2022

At Indico Capital Partners, we have partnered with Google for Startups for a pre-seed program for startups. Planless is an intelligent work management platform that automatically plans work, allocates resources and optimizes teams workload. It was founded by Gregory Stoos, who shares today how it went from a project for personal use, to a growing startup.

Planless is one of six startups that will be a part of the Indico+Google for Startups Demo Day on February 16th. Check them out and register here.

*This interview has been slightly edited and adapted for reading ease.

First, tell us about your professional background and the path that lead you to found Planless.

G: I’ve been working in the last 18 years in the marketing and software spaces and I’ve been managing many different teams and projects. I always felt frustrated about planning work. It’s a big guessing game and a very manual process. I wanted to find a solution to manage this better.

What is Planless’ ‘origin story’ — how it came to be, from idea until today?

G: The first version of Planless was for myself. I then validated the idea with the market, working with a set of Beta users. Then, the first public version was launched. The product evolved so much since the beginning. From the first version to today — only the core stayed, everything around it was changed and has evolved.

And how is your product different from others in the market? What makes it unique?

G: There are a lot of great tools out there to manage work and collaborate efficiently as a team. But when it comes to planning, resource allocation and workload management, it’s all done manually and we can only be guessing our plans. Planless is the first tool that plans work, assigns tasks and optimizes your teams’ workload for you. Just tell Planless what you want to achieve and who you have on your team and it will calculate all planning possibilities and tell you what’s the best path to success.

If you could go back in time, is there anything you’d do differently in terms of business strategy?

G: A lot…but at the same time I would be doing other mistakes by taking other roads. It’s all about failing and learning.

Can you share your best marketing and/or management tips?

G: Related to the previous answers, don’t be afraid to fail. Embrace failure. But don’t forget to learn. You should run constantly small experiments. But the rule is clear, you need to be able to measure.

Lastly, what has been the most challenging part of growing a startup? And also, the most fun part?

G: Building a startup is a rollercoaster. You go from total excitement to deep depression multiple times per week, every week. I’ve heard about it before, but it’s only when you really go through it that you truly understand the meaning of it. The fun part is that not one day is boring. You learn every day. You grow your skills and you grow as a human being. It’s really not for the faint-hearted, but if you like to be challenged, you’re in for a crazy ride.

Interview by Matilde Castro.