Evaluating a founding team with no prior startup experience is like trying to predict the potential of a seed that has yet to break through the soil. It requires a unique lens—one that can see beyond what’s visible and connect the dots between potential, drive, and adaptability.
Imagine a seed, buried deep beneath the surface. To the casual observer, there’s no clear sign that it will ever push through the soil. But for the right gardener, this seed holds immense promise. It’s not about what’s visible above ground; it’s about understanding the hidden potential below—the intricate network of roots, the richness of the soil, and the subtle signs that growth is already underway.
Evaluating a founding team with no prior startup experience is much like this. There are no guarantees—no proven track record, no case studies of previous success. But a skilled evaluator sees beyond the credentials and flashy pitch decks, to the deeper qualities that can transform inexperience into an advantage.
It’s a process of looking closer, asking the right questions, and exploring the mindscapes of these founders. What drives them? How do they approach uncertainty? Are they willing to adapt when the weather changes, or will they stay rooted in their ways?
Much like understanding a seed’s growth requires a mix of intuition and science, evaluating a nascent startup team combines experience, insight, and a deep appreciation for the stories that shape the human side of business.
Ultimately, every great startup—like every great story—starts with a seed of potential, waiting for the right conditions to grow. Finding those conditions, knowing when to water and when to wait, is what turns that seed into a forest.
“Everybody has a story to tell, and everybody deserves a chance to tell it.”
This insight forms the foundation of our work at IWB, where personal storytelling acts as a bridge between vision and action. Entrepreneurs who share their stories—whether they’re about triumphs or lessons learned—don’t just humanize their journey; they align their experiences with their business goals in a way that resonates with investors, employees, and the broader customer community.
Mapping Their Knowledge of the Terrain
Experience is a classic indicator, but deep domain knowledge is the real compass. It’s not about whether they’ve scaled a startup before—it’s about whether they understand the terrain they’re entering. I look for founders who don’t just know the lay of the land, but can articulate not just the what but the why behind trends, customer pain points, and opportunities.
Picture this: Navigating the Unknown
You’re trekking through a dense, uncharted forest. You might have a compass in hand—experience, they call it—but there’s no pre-drawn map to guide your way. And in truth, experience is only half the battle; it’s understanding the terrain that makes all the difference. This is where true navigators shine—not just those who have walked the trail before, but those who possess a deep understanding of the landscape itself.
When I evaluate founders with no prior startup experience, I’m looking for that kind of navigator. They may not have the track record of scaling a venture, but do they know the market? Can they see beyond the trees and understand why the path winds the way it does, where the underbrush grows thick, and where the ground might shift beneath their feet?
Take market trends, for example. Any entrepreneur can tell you what’s popular right now, but I’m interested in founders who can explain why a trend is emerging—who see not just the symptoms but the root causes. They understand what keeps future customers up at night, what gaps exist in the current landscape, and what opportunities are ripening just out of sight. (At IWB, we refer to this as “seeing and leading in the dark,” where innovation begins.)
Imagine two explorers facing a mountain pass. One relies solely on past experience and trudges forward on the same worn path. The other, with a keen sense of the terrain, spots an untried route—a hidden valley leading to a faster, more efficient way through. It’s this curiosity, this ability to see the possibilities that others might miss, that transforms knowledge into momentum. It’s what enables a founder to turn an ordinary understanding of their industry into a startup that doesn’t just follow trends, but shapes them.
When I sit down with a founding team, I’m listening for their sense of the landscape. Are they the ones who ask the unasked questions? Who challenge conventional wisdom? In a world where startups are defined by their ability to pivot and adapt, those who understand the terrain can find their way forward—even when the path isn’t clear. And that’s where real startup momentum begins.
Testing Their Storytelling Through Problems and Pivots
Every startup journey is a series of inflection points—moments where decisions and pivots can mean the difference between thriving and merely surviving. I lean in closely when founders share stories of past challenges—it’s in those moments that their true character emerges. Do they frame problems as opportunities? Do they highlight moments when they had to navigate ambiguity, make tough calls, or change direction? In these stories, you find the heart of their problem-solving mindscapes (mindsets).
Picture this: The Turning Point
Imagine you’re standing at a crossroads, a place where paths diverge into a maze of uncertainty. The air feels heavy with uncertainty as they decide which path to take, knowing that one wrong step could mean the end. That’s what an inflection point feels like in the world of startups—a decision that shapes the entire trajectory of a venture.
I want to know how founders interpret the landscape when the path isn’t clear. Do they see obstacles as dead ends, or as opportunities to find a better route? Founders who thrive in these moments are those who have learned to pivot gracefully. They’ve faced situations where the plan fell apart, and instead of clinging to a failed strategy, they made tough calls and changed direction.
And then there’s failure, that uncomfortable but necessary teacher. I’m always curious about how a founder talks about the times they’ve failed. Do they downplay it, sweeping it under the rug? Or do they lean into it, explaining what they learned and how it reshaped their approach? These conversations reveal resilience in its rawest form—an ability to absorb the blow, reflect, and use that experience to adapt when the next challenge arrives.
Navigating Through Storms. Think of it like this: two sailors set out on a stormy sea. One blames the waves for knocking them off course, while the other takes note of the currents, adjusts the sails, and learns to ride the swells. The first is swept away; the second gains a deeper understanding of the ocean. When I listen to founders, I’m searching for that second sailor—the one who sees beyond the immediate problem to the lesson within, who knows that every storm is a chance to become a better navigator.
In these stories, you find the heart of a team’s problem-solving mindscape (mindsets). It’s not about a perfect plan, but a relentless adaptability that can turn the roughest waters into the beginning of a new direction.
Coachability: Are They “Learn-It-Alls” or “Know-It-Alls”?
If there’s one thing I’ve learned through my journey in enabling change, it’s that the difference between success and stagnation often comes down to a simple question: Are they willing to be wrong?
An inexperienced founding team that is hungry to learn, eager to seek out mentorship, and receptive to feedback can often outpace more seasoned competitors. I probe for how they react to new ideas or constructive criticism—do they lean in, or do they get defensive? A founder who’s a “learn-it-all” can become a force multiplier, turning their inexperience into an opportunity to build a culture of continuous learning.
Picture this: The Power of Humility
Two founders are presented with a bold new idea, one that challenges their assumptions about the market. The first, seasoned but set in their ways, pushes back immediately, defending their original plan. The second, though inexperienced, pauses, asks a few questions, and lets the new perspective simmer. They’re not afraid to consider that they might have missed something. They are, in a word, teachable.
This ability to remain open—what I call the “learn-it-all” mindscape (mindset)—can be a game-changer. It’s the difference between seeing feedback as a threat and viewing it as a gift. The learn-it-all founder doesn’t just accept new ideas; they seek them out, eager to close the gaps in their understanding.
I’ve seen teams with little experience, but a voracious appetite for growth, outpace more seasoned competitors simply because they weren’t afraid to be wrong. They knew that every misstep was a chance to correct course, every piece of feedback a hidden map to a better strategy.
People-Centricity: The Hidden Catalyst
At the end of the day, startups are built on relationships (not transactional)—inside and out. How well can this team connect with their first customers, attract the right talent, and inspire investors to believe in their vision? It’s not just about charisma; it’s about how they listen, how they build trust, and how they make others feel seen and valued.
Picture this: The Art of Connection
A late-night gathering in a modest co-working space—the hum of laptops in the background, dim lights, empty pizza boxes. A handful of founders huddle around a whiteboard filled with half-formed ideas. They’re discussing the next big challenge, but the energy isn’t about bold pitches or flashy projections. It’s about connection-building—the quieter, deliberate work of listening and understanding.
When a founding team connects authentically, they’re building more than just a business—they’re building trust. It’s that feeling of being heard, of knowing your story matters, that transforms a customer.
Screw the Playbook: Here’s to the Rule-Breakers Who Change the Game
Startups aren’t about stacking accolades or wielding the flashiest resumes—this isn’t a contest for who’s got the fanciest seeds, or a fairy tale like Jack and the Beanstalk. They’re about potential, that elusive spark sitting just beneath the surface, waiting for the right moment to ignite. Evaluating a founding team without a track record is like looking at an unwritten page, a story yet to unfold. It’s not about what they’ve done—it’s about where they’re headed, and whether they have the grit, curiosity, and vision to shape their own narrative.
The best founders don’t cling to the past—no learned helplessness, no playing it safe. They get that the old maps won’t cut it when the landscape shifts. They’re the ones who crumple those maps, toss them aside, and draw new paths as they go. When the road ends or the storm rolls in, they don’t back down. They lean in, recalibrate, and keep pushing. It’s Thelma and Louise saying, “Turn back? Hell no. Keep going.” Because in a world where change is the only constant, the riskiest move is playing it safe.
As I often reflect, “The best founders aren’t defined by what they know today, but by how fast they learn tomorrow.” It’s a mindscape that turns setbacks into fuel and sees ambiguity as an invitation for the ride of a lifetime. It’s what separates those who stick to the script from those who rewrite it when the old lines stop making sense.
Backing founders like this isn’t about a predictable business plan—it’s about backing a vision still taking shape, a story with chapters yet to be written. It’s knowing that a single idea can grow into something huge, like a seed that finds the light and becomes a forest. It’s believing that a pivot isn’t an end—it’s the start of a breakthrough. Just ask Michael Jordan, Kobe Bryant, or Shaq about the power of the pivot. And a tiny spark? In the right hands, it’s enough to set an entire industry on fire.
So, here’s to the founders who don’t settle for what’s been done before, who see beyond the horizon, who know that the greatest stories aren’t read—they’re lived, each turn more daring than the last. And when you find a team with that mindscape, you’re not just betting on them—you’re betting on their ability to rewrite the rules. That’s a bet that doesn’t just aim for the status quo—it’s a bet that’s looking to change the game. And that’s the kind of story that keeps us watching, talking, and wondering what’s coming next.
You need eagles wings to get over things that make no sense in this world. — Tom Petty