April 6, 2025

My best system for free:

Scot Chisholm

written By
Scot Chisholm

Scot Chisholm

written By
Scot Chisholm

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My best system for free:

Last time we talked about the issues with popular goal systems – especially OKRs.

This week I’m sharing a solution to all those problems…

The system is called WhyGos (“why-goes”), as in:

  • Why – why this goal is a priority

  • Goal  – what we are trying to achieve

  • Outcome – how we measure success

It’s the goal system we developed at Classy and is now used by hundreds of founders around the world (via Highland).

This is the exact same system that forced ruthless prioritization across our company and helped us grow to many hundreds of millions in value.

And today, I’m sharing the entire thing with you for free.

If you’re tired of overly complex goal systems, you need to check this out. Any company of any size can implement it…

Till next week,

Never say die 🏴‍☠️

Scot

HIGHLAND

What people get wrong about PMF

Most founders treat product-market fit like it’s a magic switch. One day you’re off. The next you’re on.

But that’s a myth.

A few weeks ago, Hiten Shah sat down with our Highland members to reframe the whole PMF conversation. According to Hiten, product-market fit isn’t a switch—it’s a dial.

You calibrate your way toward it over time based on how your users actually behave. Here’s a couple take aways if you’re still chasing PMF:

  •  🔥 Don’t pivot too fast, or too drastically. Most founders give up before they’ve iterated deep enough.

  • 🔥 Look at user behavior, not just feedback. Squeaky wheel customers can create false signal.

  •  🔥 Retention > acquisition. If your product’s sticky, that’s your strongest proof of PMF.

The full session and templates are live inside Highland. If you’re serious about scaling and looking for an operating system for your startup, apply here: www.joinhighland.com