Founder-Future Fit

Authenticity matters

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Founder-Future Fit

Key takeaways:

• Greatness rests not just on general traits like ambition, curiosity, adaptability, and a relentless focus on users. It hinges equally on how authentically a team aligns with the future they aim to create.

• At times, a team lacking in experience is better suited for the future. They see new possibilities with a beginner’s mind, unclouded by past experiences. In other cases, seasoned expertise and a proven track record is important to build customer trust.

• Justin Kan personifies this lesson. His success with Justin.tv/Twitch showcases the power of a founder's fit with the future. Yet, the same person can falter if that alignment is absent, which was the case with his subsequent startup, Atrium. We are fortunate that he shares his contrasting stories with such candor.

I talked to Justin Kan of Justin.tv/Cruise fame a couple of weeks ago on my Pattern Breakers podcast. His story reminded me of one of the critical characteristics I’ve seen in the breakthrough startups: The importance of “Founder-Future Fit.”

The Importance of Founder-Future Fit

What are the traits of a great founder? It’s tempting to respond in broad strokes: Vision and insight. Tenacity and endurance. Ambition. Adaptability. Curiosity. A maniacal focus on users.

These attributes ring true, but it’s important to remember that different opportunities call for different types of founders and teams. 

Founder-Future Fit means a founder or startup team aligns more authentically with a radically different future than anyone else. This alignment brings great advantages. Authentic and practical passion for future technologies enables founders to discover insights ahead of the curve and grasp vital details overlooked by others. This greatly contributes to uncovering ideas with groundbreaking potential. This authenticity also draws in early customers, investors, and believers. Which gives the startup the edge over its competitors in achieving product-market fit first.

So then, why is Founder-Future Fit so important and what should you look for to see if you have it?

The Advantages of Authenticity

Founders don’t create the future by themselves. They co-create it with early believers who agree with their vision. Early believers make choices about who they want to trust. 

These are the traits they seek:

• Who knows this future the best?

• Who is the most intrinsically motivated about this future?

• Who knows the best people to make this future happen?

Returning to the story of Justin Kan…

When Justin Kan co-founded Justintv, the idea of livestreaming one's life 24/7 seemed absurd. Yet, Kan epitomized the future he pursued. He embraced being an influencer before the term existed, driven by intrinsic motivation. His understanding of how people his age wanted to express themselves was more valuable than the knowledge held by seasoned media executives.

Contrast Justin.tv with Justin’s next startup, Atrium. The original idea behind Atrium was to revolutionize the legal services industry by using technology to streamline and automate legal workflows, especially for startups. In contrast to Justintv, which seemed kind of crazy, Atrium made sense to lots of people when they first heard about it. And yet, Justin Kan attributed much of Atrium’s downfall to his own lack of zeal for legal tech. Reflecting on it in our interview, Justin confessed to being driven by extrinsic motives. He wanted to match the success of Brian Chesky or Drew Houston. His passion did not lay in the future he sought, but in becoming a higher-status founder.

Founder-Future fit varies greatly among startup opportunities. 

Take the founders of Applied Intuition. They create very complex software for autonomous and electric vehicles. When you deliver this type of software, you’re talking to the CEOs of the major car companies. When they look at you across the table, they need to believe that you are the most qualified person in the world to solve their problem. Success demands industry expertise and a track record of success. It shouldn’t come as a surprise that Applied’s founders, Qasar Younis and Peter Ludwig, were raised in Michigan and worked at Google on its maps initiative along with Waymo. Qasar had also worked at General Motors earlier in his career. They had a background from central casting to start a company like Applied Intuition.

Another example is Todd McKinnon of Okta. As Salesforce's VP of Engineering, Todd had seen customers struggle with deploying more and more cloud applications. He knew they were struggling with identity management and he was confident he could build a solution for them. Selling to them required credibility; these customers needed assurance that a startup could deliver. Todd's strong founder-future fit for this opportunity was obvious. 

Time and again, I’ve seen the power of Founder-Future Fit as an early signal. 

Eric Yuan embodied strong Founder-Future fit when he started Zoom. He had spent over a decade at WebEx and Cisco, gaining valuable experience in video conferencing. Seeing the limitations of existing platforms, he envisioned a simpler, more user-friendly solution, anticipating the need for mobile conferencing. Originally called Saasbee, Zoom aimed to be a consumer-focused video chat app, focused on providing what he called “poor man’s telepresence.” Ten months after their seed funding, they shifted focus to business, renamed themselves Zoom, and adjusted their strategy. Yuan's Founder-Future fit was a more powerful signal about the future prospects of his startup than his initial product concept.

As a seed investor, it's a humbling lesson I’ve seen repeatedly: founder-future fit often outweighs the current product's correctness in predicting the potential for a breakthrough. Founders can navigate the product to something else. But it’s tough for them to overcome a lack of authenticity if it never existed in the first place.

So what does this mean for you?

There's only one you in this world. 

Being a great founder means choosing opportunities that let you be your best self. 

Yes, the general traits of greatness matter. 

But so does your ability to focus on where your skills and intrinsic motivations lie, to know where you and your team have the edge, and where you don't. Founder-future fit is about asking which future aligns most authentically with who you are, what motivates you, what you know, and who you know. It's about understanding how your insights and experiences impact you and your team’s ability to reach product-market fit first.

In the end, being a great founder is largely about authenticity. You must believe you are the one to see the right product to build before anyone else. You need to be the best at inspiring early believers to follow you, and not other alternatives. You need to love the domain you are building in. Todd McKinnon of Okta has said, "Sometimes you have to believe even when you don’t believe." 

If you’re not chasing something you’re truly obsessed with, you'll give up while a more passionate founder will press on. Often, that is what separates failure from greatness.

We should all be grateful for Justin Kan’s willingness to tell the truth with no tricks about his startup journey. His openness and courage in telling us about his successes and failures are very helpful in understanding what leads to breakthroughs. He personifies the importance of founder-future fit…in both his successes as well as his setbacks. And in so doing, shows us the power of aligning our efforts with where we are best fit to truly shape the future.