Scaling with Purpose: Lessons from Brian Halligan’s Journey from Startup to Scale-Up

Recently, my cofounder Stuart P. Turner shared a fascinating article with me from none other than Brian Halligan, the man who co-founded HubSpot and grew it from startup to a $25 billion giant. No big deal, right? Brian’s journey from scrappy startup founder to scale-up CEO is full of lessons that hit close to home—especially for those of us in the early stages of building something great.

While I’m scaling up my service business and at the early stage of building our enterprise SaaS business, I've held leadership positions in large enterprises, so a lot of what Brian shared really resonated with me. The road from startup to scale-up is full of twists and turns—some exciting, some terrifying—but hey, that’s what makes it fun, right?

The Shift: From Perspiration to Inspiration (and maybe a little Perspiration again)

Brian highlights how the role of a CEO shifts dramatically as you scale. When you’re in startup mode, it’s 90% hard work (perspiration) and 10% vision (inspiration). But as the business grows, that flips: 90% inspiration, 10% perspiration. Honestly, I think I’m still in that 80/20 zone—80% hustling, 20% dreaming about the future. But it’s a shift I’m preparing for as we scale both our service business and our SaaS platform.

Here’s the kicker: As you scale, your team looks to you for inspiration, not just a solution to every problem. That’s a big mindset shift, and it takes practice. But it’s also exciting—because that’s when you get to paint the big picture and guide everyone toward it. (Though I’ll admit, the occasional late-night grind still comes with the territory!)

Staying Close to the Customer: Lessons from Richard Branson

One thing Brian didn’t mention, but I couldn’t help but think of, is a lesson from Richard Branson’s playbook. Branson famously flies economy on his own airline just to see what’s happening on the front lines. I mean, sure, the guy has a private jet, but he values staying close to the customer experience. That’s something I’ve always admired.

It’s easy to get distanced from the day-to-day realities of customers as your company grows. But staying in touch with their needs, frustrations, and wins? That’s where the magic happens. Whether it’s through direct feedback, personal interactions, or, in Branson’s case, hopping into coach class, it’s critical to keep the customer at the center as you scale.

Trust and Bold Decisions: The Trust Battery

Brian talks about managing the “trust battery” as a CEO—a concept that resonates deeply with me. Every decision we make as leaders either charges or depletes the trust we’ve built with our teams. When trust is high, it empowers bold decisions and fosters a sense of shared purpose. But when trust erodes, even small decisions can feel risky.

I’ve learned that trust is rooted in values and culture, not just skills or experience. Recently, I had a personal experience that reinforced this: working with people who may have the right skills but don’t align with your vision can quickly drain trust. That’s why I focus on building teams with individuals who share our core values and culture—people who are not only talented but also aligned with what we’re trying to achieve. When trust is strong, making bold moves becomes easier because you know your team will have your back.

Culture: Your Second Product

Brian nails it when he says that culture is your company’s second product. It’s something I’ve been very mindful of as we build our team. In a startup, culture isn’t just a set of values on a PowerPoint slide—it’s how you do everything, from how you treat your team to how you treat your customers. And like any good product, culture needs continuous care and iteration.

As our company grows, I’m committed to making sure that culture stays front and center, just like our product. If we get that right, scaling becomes a lot easier, because the right people—missionaries, not just mercenaries—will want to join and stay.

Knowing When to Hold Back and When to Leap Forward

Unlike Brian, I didn’t need a life-and-death experience to learn when to hold back and when to take bold risks. Over the years, I’ve realized that growth is about knowing when the timing is right for bold moves—and when it’s better to step back and reassess.

Scaling a business requires audacity, but it also demands patience. There will be moments where a leap of faith is necessary, but there will also be times when holding back is the smartest strategy. Learning to navigate this balance has been one of the most valuable lessons in my journey so far. For me, it’s not about simply taking risks for the sake of growth; it’s about taking the right risks, guided by trust, timing, and alignment with the bigger picture.

My Takeaways for Fellow Founders

• Inspiration Over Perspiration: As your company grows, focus on inspiring your team and guiding them toward the vision. Let go of the need to do it all yourself.
• Stay Close to Your Customers: Keep a direct line to your customers, even as your business scales. Their feedback and experiences should always guide your next steps.
• Build Trust First: Surround yourself with people who share your values and culture. Trust is the foundation that allows you to make bold moves with confidence.
• Culture is Critical: Treat your company’s culture like a product—it needs constant attention, iteration, and care. A strong culture will scale with you.
• Be Bold, But Be Smart: Take bold risks when they’re needed, but always with calculated precision. Know when to push forward and when to pull back.

Scaling a business is both challenging and rewarding, and I’m grateful to be on this journey. Brian Halligan’s insights serve as valuable reminders of the lessons ahead, while my own experiences have shaped the path I’m currently on. If you’re navigating your own journey of growth, remember to stay grounded, trust your team, and lead with both purpose and inspiration.

So, what lessons have you picked up on your own journey? How are you building trust and scaling your business with purpose? Let’s keep the conversation going and inspire each other to reach new heights.

Yours truly, Eve Chen