2025 - Week #27

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Startups for the Rest of Us - Episode 781

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In this episode, Rob Walling talks about mistakes has done during his founder’s career. I’ve found some interesting points in the episode. I would like to focus on one point in particular here.

Mistake #5: “Trying to do everything solo”

Rob had tried to do everything without hiring full-time employees; firstly completely alone, and later with some contractors, but he says:

There was no loyalty and there was no cohesion. The contractors didn’t even really know each other, so it was barely a team. And the approach wound up sucking because my entire job was managing contractors, managing projects, assigning things, checking on things, and it’s like it’s not fun […] I don’t want to just be a paper pusher in essence or a project manager. I want to actually get s**t done with ambitious people who really want to build something incredible

Using his words, he had hired “task level thinkers”, but he needed also “project level and owner level thinkers”. He developed this concept in the episode #551 of his podcast.

About task level thinkers, he says:

For years, I operated with task-level thinkers, and I was happy […] These are folks who were doing design work, folks who were doing administration, folks who were doing email support, developers […]

About project level thinkers, he says:

But what I realized is I was then doing all the owner-level thinking which was longer-term stuff, and the project-level thinking which was this project needs—this is project management—seven things to happen, so now I get to manage all those people […] I hired a couple of people who were more project-thinkers. I can hand an entire project and they would then either manage the resources for me or they could do the whole thing themselves […].

About owner level thinkers, he says:

[…] after we were acquired […] I started seeing folks working inside a company who were not the C-suite, they were not owners, they were not founders of the company, but they really owned an entire segment and they thought creatively around it. So someone who’s a marketing strategist who ran this whole team of people, wasn’t just thinking about projects. Actually, each of his people have their own projects, but he was thinking long-term, what do we need to do in 12–18 months? Coming up with new ideas, listening to the audio books, listening to the podcast, reading the books, and being what I call an owner-level thinker where it’s not about the equity that he owned but it was about ownership of the the results […] from the vision to the implementation, and working with the team to do it.

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