My bluesky strategy to a $100M valuation, but what really happened...

15 Mar 2024 · 19 min
19:03

In this video Joshua Fraser walks through the "Blue Sky" strategic planning framework he created at Estated, which served as a living North Star for the company’s annual planning, quarterly OKRs, and departmental alignment. He explains how the framework starts with a concise vision statement that defines the product and target markets, followed by a set of core values centered on "happy, healthy humans" and continuous improvement (Kaizen). Fraser details the multi‑year financial targets (ARR, MRR, valuation goals) and how they were broken down into 12‑month, 90‑day, and quarterly objectives with measurable key results. He shares concrete metrics (e.g., $2.3 M ARR, $415 k MRR, 25‑person headcount) and the outcomes of those OKRs, including missed targets and the impact of a hostile data‑provider renegotiation that ultimately led to the sale of Estated for CAD $20 M. The video also covers cash‑reserve discipline advised by Foundry Group, people‑first initiatives (weekly surveys, perks, remote culture), and a detailed departmental blueprint (people, finance, marketing, sales, product, engineering, data, legal). Fraser provides a template for other entrepreneurs to adapt the Blue Sky document, emphasizing its flexibility and the importance of transparent communication with teams, advisors, and investors.

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