The journey from startup to scaleup is exhilarating yet fraught with uncertainty. You’re brimming with innovative ideas, and passionate about building something new. But the path to success is rarely clear. Many startups get stuck in "survival mode," scrambling to meet short-term delivery goals while controlling cash burn goals, without a clear grasp on exactly where to be in the long run. This is where Endgame Thinking comes in. It's a future-driven framework that helps you pull the present into the future to establish your ultimate goals and work backwards to map out the right steps to get there.
Over the past 16 years as CEO and co-founder of Star, I have worked with hundreds of startups and witnessed our own growth from a Silicon Valley startup to a global entity. Through this journey, we've experienced both highs and lows, but most importantly, we've mastered strategic planning using Endgame Thinking.
Beyond survival mode
Startups often value action-oriented employees – a vital trait. However, as startups grow and the demands of investors and market dynamics intensify, a robust operational system and aligned strategic focus is essential (actually I’d argue this is important to all businesses, regardless of size). This system should not only unify everyone towards a common goal, but also balance foreseeing the future with the daily effort of “getting sh*t done” (a badge of honor for people who work at startups). Yet, this focus can falter if the team fails to attach their tasks to a long-term goal and execute with a clear purpose.
By clarifying an endgame early on and working backwards to establish key milestones and deliverables, startups can ensure their tactical decisions align with their broader goals. This reduces the feeling of being pulled in different directions or cross-functional tension and fosters a more focused approach.
Endgame Thinking isn't just about survival; it's about strategic advantage. It helps founders and their teams anticipate challenges and identify opportunities by proactively planning for different scenarios. This clarity simplifies communication and helps everyone work towards a common vision and establish shared values.
Create tomorrow, today with Endgame Thinking
Adapt or die
The beauty of this process is that it assumes pivots and changes. Endgame Thinking is not about having an immovable goal – it’s about having the ability to challenge yourself, going through this exercise on a regular basis with your team when things change, and things always change. You can’t create a clear view of all future possibilities, but you can still follow a North Star when there’s an earthquake.
Some of the most successful brands in the world today pivoted away from their initial startup ideas, Slack, YouTube, Instagram and Shopify for example. They all weathered different storms.
A great example, that I personally got to witness, is a company called CloudMade, founded by the team that created OpenStreetMap. Initially, they focused on mapping services and SDKs for apps and automakers. After a number of years, they examined the macro environment including consumer behaviors, technological advancement and evolving business needs from their clients, and matched these against their organizational capabilities for a competitive edge. This led them to pivot their focus to AI solutions around personalization with a laser focus on the automotive OEM space. Had CloudMade been dogmatic about its business strategy and endgame, they wouldn't have achieved the success they have today, including their recent acquisition by Stellantis, one of the world's largest car manufacturers, to integrate their technology in-house.
Lessons to first-time founders
Endgame Thinking is also a methodology that equips leaders with the tools to navigate an ever-changing business landscape. A core tenet of this methodology is enhanced adaptability, allowing leaders to effectively manage change and lead their teams through unforeseen challenges.
By envisioning a compelling endgame and working with your leadership team (or employees if you’re in the pre-seeding stage) on how to get there, people can move forward with a shared vision and better understand how their individual contributions drive the company's success. This fosters a sense of purpose and reduces anxieties and resistance associated with change – the number one reason business transformation or strategy implementation fails.
A good endgame thinker needs to be great at dealing with passions and anxieties. Tap into people’s passions and activate them, and have radical self-judgment and assessment. Challenge yourself as radically as you can and don’t drink your own Kool-Aid. Let your ego go, be comfortable that you don’t know it all. These are the required characteristics to succeed at scale.
