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    Home»Business»I’ve Backed 20 Startups. Here’s What Actually Separates the Ones That Win From the Ones That Stall.
    Business 7 Mins Read

    I’ve Backed 20 Startups. Here’s What Actually Separates the Ones That Win From the Ones That Stall.

    Business 7 Mins Read
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    Opinions expressed by Entrepreneur contributors are their own.

    Key Takeaways

    • A captivating idea is the entry ticket to early-stage investing, but the founders who succeed are the ones with a specific set of traits — humility, adaptability, decisiveness under uncertainty, and the self-awareness to build the right support system around them.
    • Most startup problems aren’t surprises — execution gaps, capital shortfalls, hesitation, and weak supporting teams show up predictably in nearly every early-stage company; what separates the ones that win from the ones that stall isn’t the absence of those problems, but the founder’s ability to make decisions and keep moving through them.

    When you first get into startups, you naturally gravitate toward the idea. You listen to the pitch, you evaluate the market and you try to decide whether the world actually needs this thing. It’s a good instinct. Fundamentally, I think that you need a captivating idea and pitch. However, that isn’t enough.

    After spending the last several years investing in close to 20 startups, sitting through hundreds of pitches and working directly with founders at the earliest stages, one thing becomes very clear. The idea matters, but it does not decide the outcome. In fact, one of the first questions I find myself asking founders now is simple: what happens if your idea doesn’t exist? Can the world go on without it?

    Most founders will say no. The world needs this. That’s the conviction you want to hear. But then the real evaluation starts.

    A needed idea is different from a good idea

    Not every startup fills a void. That’s one of the biggest misconceptions in early-stage investing. There are already plenty of burger places. That didn’t stop Shake Shack from building a great business. The difference is that it brought something sharper to the market. It executed better. It created a product and experience that people chose.

    I’ve seen plenty of ideas that sound interesting but don’t carry urgency. They don’t solve a meaningful problem, and they don’t create demand. On the other hand, I’ve seen companies enter crowded markets and win because they understood exactly how to differentiate and execute. An idea has to earn its place. It has to feel necessary, or at the very least, undeniably better.

    Most startup problems aren’t surprises

    Another realization that comes quickly is how predictable most startup challenges are. Execution gaps, lack of capital, weak supporting teams, hesitation to take risks or the inability to move from concept to real delivery. These show up again and again.

    What separates the companies that move forward from the ones that stall is how they deal with the inevitable issues. Some founders hesitate. They wait for more information. They worry about making the wrong move. In a startup, that hesitation can be fatal. One failed project, or one missed opportunity, can stop momentum entirely.

    The best founders make decisions. They move, adjust and understand that standing still is the only guaranteed way to lose.

    The founder is the deciding factor

    It has become very clear to me that the experience and judgment of a founder have an enormous impact on the short- and long-term success of the company. Early on, I thought of a founder as one of several important variables. Now, this sits at the top of the list. Founder, founder, founder. You start to look for very specific traits. Humility. The ability to listen. The willingness to collaborate. The awareness to know they don’t have all the answers. The ability to execute, hire, communicate and lead.

    Because no founder does this alone. They need people around them. They need advisors, investors and team members who can challenge them and make the idea better. I’ve seen great ideas fail because the founder couldn’t adapt. I’ve seen average ideas succeed because the founder could. That’s the difference.

    Chaos doesn’t mean you’re moving fast

    There’s a perception that startups succeed because they move at breakneck speed and embrace chaos. There is some truth to the speed part. There is far less structure, and decisions can be made quickly. That’s an advantage. But chaos by itself is not a strategy.

    I’ve seen startups that are disorganized and reactive, and I’ve seen others that are slow because they’re afraid to take risks. Both scenarios create problems. The reality is that startups require a balance. There is more freedom, but there still needs to be direction. The founder has to know where the business is going, even if the path changes along the way.

    The companies that work are the ones that combine speed with clarity and intent.

    Experience helps, but it doesn’t guarantee anything

    One of the more humbling aspects of investing in startups is realizing how different this world is from running large organizations. In a corporate environment, everything is structured. There are processes, timelines and accountability systems. In startups, the pace is unpredictable, and the way people work can be very different.

    At the same time, experienced founders tend to navigate this environment better. They understand the pitfalls. They know when to move fast and when to pause. They surround themselves with the right people. That experience shows up in subtle ways, but it matters.

    What actually works

    After years of investing, advising and working alongside founders, the patterns become difficult to ignore. The companies that succeed tend to have a few things in common. They start with an idea that can compete and deliver in the real world. They are led by founders who are adaptable, self-aware and willing to take action. They build the right support system around them. They move quickly, but with intention.

    Most importantly, they keep going. Because startups are fragile, one mistake can set you back, one missed opportunity can slow everything down, but the founders who continue to learn, adjust, and execute are the ones who give themselves a chance. Success needs a strong idea, but it is fueled by more than that. It’s driven by the ability to execute, adapt, and push through uncertainty. The idea gets you started. The founder determines how far you go.

    Key Takeaways

    • A captivating idea is the entry ticket to early-stage investing, but the founders who succeed are the ones with a specific set of traits — humility, adaptability, decisiveness under uncertainty, and the self-awareness to build the right support system around them.
    • Most startup problems aren’t surprises — execution gaps, capital shortfalls, hesitation, and weak supporting teams show up predictably in nearly every early-stage company; what separates the ones that win from the ones that stall isn’t the absence of those problems, but the founder’s ability to make decisions and keep moving through them.

    When you first get into startups, you naturally gravitate toward the idea. You listen to the pitch, you evaluate the market and you try to decide whether the world actually needs this thing. It’s a good instinct. Fundamentally, I think that you need a captivating idea and pitch. However, that isn’t enough.

    After spending the last several years investing in close to 20 startups, sitting through hundreds of pitches and working directly with founders at the earliest stages, one thing becomes very clear. The idea matters, but it does not decide the outcome. In fact, one of the first questions I find myself asking founders now is simple: what happens if your idea doesn’t exist? Can the world go on without it?

    Most founders will say no. The world needs this. That’s the conviction you want to hear. But then the real evaluation starts.



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