What We Can Learn from Simon Squibb

Simon Squibb is someone whose name stands out if you’re serious about entrepreneurship. He’s spent over 30 years in the game, building 19 companies and investing in 78 startups. If there’s anyone who understands the ups, downs, and everything in between, it’s him. His video, “30 Years of Business Knowledge in 2hrs 26mins,” is like sitting down with a seasoned mentor who’s distilling a lifetime of lessons into something you can actually use today.

Now, Simon isn’t about throwing out generic advice. What he shares is practical, grounded in the reality of what it means to build a business from scratch, face setbacks, and still find a way to come out on top. His insights are a treasure trove for anyone—whether you’re just starting out or you’ve been in the trenches for years. In this article, I’ll walk you through some of the key takeaways from his video, the ones that really hit home and can help you navigate your own business journey.

The Power of Passion and Obsession

Let’s start with passion. Simon doesn’t just mention it in passing—he makes it clear that passion isn’t just a nice-to-have, it’s the engine that keeps everything else moving. We’ve all heard it before: “Do what you love.” But Simon takes it further. He says that without a genuine love for what you’re doing, you’re setting yourself up for burnout. Passion is what keeps you going when things get tough—and believe me, they will.

But finding your passion isn’t always straightforward. It takes some digging. Simon suggests doing some serious self-reflection, exploring different areas until you find that one thing that lights a fire in you. Once you’ve got it, don’t let go. Dive in headfirst. Make it a part of your daily life, whether that’s through reading, practicing, or connecting with others in the field. It’s about more than just working hard—it’s about working with purpose.

However, Simon doesn’t stop at passion. He talks about deep obsession—the kind where you’re not just interested in what you’re doing, but completely committed to mastering it. This is where the magic happens. When you’re obsessed, you don’t just put in hours—you put in the right kind of hours, the ones that lead to real growth. And it’s this obsession that naturally leads to inspirational leadership. Your enthusiasm becomes infectious, drawing people in and motivating them to be part of your vision.

The Myth of Originality and the Power of Collaboration

One of the most refreshing things Simon brings to the table is his take on originality. There’s this myth out there that to succeed in business, you need to come up with a completely original idea. But Simon says, “Hold on—don’t get stuck on that.” Instead, he suggests looking at what’s already out there and finding ways to improve it.

This isn’t about copying—far from it. It’s about innovating through collaboration. Simon encourages partnering with others who share your vision. When you bring together different perspectives and skill sets, you often find solutions that you wouldn’t have come up with on your own. Take Airbnb, for example. They didn’t invent short-term rentals; they simply made it better by creating a user-friendly platform and fostering a community around it.

This advice is a game-changer for anyone feeling the pressure to be the next Steve Jobs. Simon’s message is simple: don’t worry about being completely original—focus on making something better. And don’t be afraid to collaborate. It’s not about who gets the credit; it’s about creating something that works.

Starting Small, Scaling Big, and Building a Sustainable Culture

Simon also shares some invaluable advice on starting small and scaling. If you’re like most entrepreneurs, you probably have big dreams—but those dreams can feel overwhelming, especially when you’re just starting out. Simon’s advice? Start small. Build something that meets a market need and can generate revenue from day one. This way, you’re reducing your risk and getting real-time feedback that can guide your next steps.

By starting small, you give yourself the space to make mistakes, learn, and grow. Simon highlights companies like Dropbox and Slack, which began with simple, minimal viable products (MVPs) to test the waters before scaling up. This approach allowed them to refine their offerings and build a strong foundation before going big.

But scaling isn’t just about growth—it’s also about sustainability. Simon emphasizes the importance of building a strong business culture from the get-go. It’s about more than just making money; it’s about creating something that lasts. A shared vision, strong values, and a long-term focus are the pillars of a sustainable business. Look at Patagonia or Zappos—these companies didn’t just focus on profits; they built cultures that align with their broader goals, and that’s a big part of why they’re still thriving today.

Mastering Sales and Leveraging PR

When it comes to sales, Simon gets straight to the point: it’s all about understanding your customers. He stresses the importance of deep research—knowing not just who your customers are, but what they need, what they value, and what problems they’re trying to solve. This isn’t about pushing a product; it’s about offering real solutions that make a difference in your customers’ lives.

Authenticity plays a big role here too. Simon makes it clear that the best salespeople aren’t the ones who close the most deals—they’re the ones who build the strongest relationships. Honest communication and a focus on providing genuine value are what lead to long-term success. Manipulative tactics might get you a sale today, but they won’t build the kind of trust that leads to lasting customer loyalty.

Simon also shares some smart strategies for leveraging PR and marketing. He talks about the power of storytelling—crafting a narrative that resonates with people on a deeper level. It’s about sharing your journey, your values, and your impact in a way that captures attention and builds credibility. And when it comes to outreach, Simon suggests being personal and targeted. Know who you’re talking to and tailor your message to fit their interests. This isn’t about blasting your story to everyone; it’s about making sure the right people hear it.

Embracing Risk and Building Resilience

Risk is part and parcel of entrepreneurship, and Simon doesn’t shy away from that. In fact, he embraces it. He talks about the importance of taking calculated risks—ones that are aligned with your business goals and that you’ve thought through carefully. But he also acknowledges that sometimes, even the best-laid plans don’t work out. That’s where resilience comes in.

Building resilience means developing the mental toughness to bounce back from setbacks. It’s about keeping a positive mindset, staying focused on your long-term goals, and being adaptable when things don’t go as planned. Simon shares examples from companies like Netflix and Amazon, which didn’t just survive challenges—they thrived by pivoting and innovating when the time called for it.

Building Teams and Preparing for Exit

One of the final pieces of the puzzle Simon talks about is building and managing teams. He emphasizes the importance of hiring not just for skills but for cultural fit. The people you bring on board should share your values and vision, as this will enhance teamwork and productivity.

Leadership is key, too. Simon believes in leading by example—being the kind of leader who inspires and empowers your team. Open communication and continuous development are crucial. By investing in your team’s growth, you’re not just building a stronger business; you’re creating a culture where people are motivated and engaged.

Finally, Simon touches on the importance of preparing for your business’s exit, whether that’s through a merger, acquisition, or public offering. He advises entrepreneurs to plan their exit strategy early, ensuring that when the time comes, the transition is smooth and the value is maximized.

Bringing It All Together

Simon Squibb’s wisdom, captured in his video “30 Years of Business Knowledge in 2hrs 26mins,” is like having a roadmap to entrepreneurial success. He covers everything from finding your passion to mastering sales, from embracing risk to building a strong team. The best part? His advice isn’t just theoretical—it’s grounded in real-world experience, making it both practical and inspiring.

If you’re serious about your business journey, Simon’s insights are not to be missed. Take these lessons to heart, apply them to your own path, and watch as they guide you through the complexities of entrepreneurship with clarity and confidence.