Making career and investment decisions
I was recently asked what I look for in the founders I back?
A heuristic I find particularly valuable is asking myself: in another world, would I work for this founder?
In this post, I hope to help you to not only make better investment decisions, but also better startup employment ones too. Let’s discuss three specific questions I find valuable.
1. The Visionary Impact: How Inspired Am I By The Founder’s Vision?
A founder’s vision is a startup’s north star, and compels investors, employees and clients to believe in the impossible – and strive to make it a reality.
When I evaluate a founder with the lens of wanting to work for them, I look for that spark of inspiration – the boldness of their ideas, the clarity of their foresight, and the passion in their pitch. A compelling vision is not just about the end goal; it is about the narrative they weave, how they see the world changing, and their startup’s role in that transformation. The vision should be potent enough to resonate on a personal level, igniting a desire in me to be part of that change.
For investments I make, I look for deep inspiration by that vision. This is also a descent indicator that the Founder will be able to hire top talent to bring this vision to reality, raise capital and ultimately succeed.
2. The Art Of Execution: Do I Believe In The Founder’s Managerial Style And Execution Abilities?
My second question focuses on the Founders’ managerial style and execution capabilities. It is one thing to dream big; it is another to make it happen.
Answering this question requires a multi-dimensional reflection: Would I want to work for this team? Will the founder be able to manage adversity and help their team get through it? What is their decision-making process? Will everyone’s voices be heard? Are they willing to take feedback (and coaching)? Do they communicate effectively both upwards and downwards? How fast do they make decisions? How readily do they change their mind and how firm are their beliefs? (this cuts both ways)
Ultimately, the startup’s ability to launch a product and scale operations will rely on these dynamics. If my answer to this question is yes, it helps me predict the Founder’s ability to execute the business plan, and crucially keep the team happy and fulfilled while doing it.
3. The Time Investment: Would I Invest My Most Precious Resource?
Venture capitalists have a portfolio of startups. Employees only have a single bet (at a time). The final and question, and for me, the highest bar is whether I would invest my most precious resource: time, into helping this founder realize their vision.
For an employee joining a startup, they are making a big bet: a period of time in their career. It means believing in their vision and mission as if it were my own.
This question thus forces me to ask: would I be proud to have played a part in what they are building? Do I believe in the problem they are solving deeply enough to dedicate years of my life to it?
This introspection goes beyond professional due diligence; it reflects shared values and purpose. This lens of course also conflates many important questions at once – the potential upside in the business, the importance of the problem it solves, the team dynamics. Because employees have a portfolio of one, the bar is particularly raised here.
As an investor, these are of course not the only questions I ask. At Fluent Ventures, the firm I work at, our strategy is geographic arbitrage, where we invest in global proven business models around the world. But, as I reflect on these questions, many of the great founders I’ve had the privilege of working with over the last decade have scored highly on these dimensions.
What other questions would you ask?