Founder Lessons: Nicole Kelley on Vision, Focus, and Building With Heart
Last week I sat down with Nick Silva, CEO and Founder of Startup Skool. Read on for tips on growing and scaling startups in the early days, with the goal of making them (and you) actually last.
First, On Vision and Clarity
Nick: One of the biggest lessons I’ve learned is how critical it is to start with a clear vision. I’ve run a couple of businesses now, and in hindsight, I see that even if you have the right team, strong work ethic, and momentum, it won’t matter if you’re moving in the wrong direction. You’ll still end up somewhere you didn’t intend. So when I think about startups, vision isn’t a luxury, it’s essential. You can’t lead people well if you aren’t clear on where you’re going.
Nicole: 100%. I call it your North Star. It's your personal why. We spend so much of our lives working, and if we don't understand the deeper reason for why we're doing what we do, we risk burnout and misalignment. The vision doesn’t have to be fully defined or permanent. It can evolve. But it gives you something to hold onto when things get tough. It reminds you why you care in the first place. I have a document that’s kind of a living North Star. It’s where I keep my values, my intentions, my reasons. And it helps me come back to myself when I start spiraling. It doesn’t need to be static. It just needs to feel true.
Nick: I love that. I actually keep a personal doc of heuristics, and one at the top is "It’s a guide, not a prison." Early on, I set these rigid goals and timelines and ended up feeling trapped. I thought I was being disciplined, but I was actually building a cage for myself. The vision should give direction, but with enough flexibility to enjoy the journey.
On Reasons and Motivation
Nick: Let’s talk about motivation—why we do what we do. A lot of people get stuck in autopilot: going through the motions without being intentional about why they do what they do. How do you see the role of motivation in shaping culture and performance?
Nicole: Motivation needs to be honest. Not what society tells us we should want, but what we actually care about. If someone builds their goals around an inauthentic purpose or motivation, the minute things get tough, it all falls apart. But if the motivation is real—even something small and personal—it keeps you moving. You don’t need some grand mission to stay motivated. You just need a purpose that matters to you.
Nick: Exactly. So many of us start off chasing arbitrary goals. For example, I used to say I wanted a $100M company. But why? It was just a validation game. When you unpack it, the real desire is often about feeling worthy or being seen. That’s why clarity matters so much.
Nicole: Right. We often confuse performance with leadership. Performing is exhausting. Leading can still be hard, but it’s resourced. It’s intentional. And it’s built on presence, not on proving. And when you start to act on small, authentic goals—like getting better sleep, eating well, or building a slower, more intentional rhythm—you create momentum. That snowball effect builds trust with yourself. You don’t need the perfect 10-year plan. You just need to start.
On Goal Setting and Progress
Nick: A lot of people obsess over planning. I used to build detailed roadmaps that looked great on paper but didn’t actually help me move. There’s a fine line between planning and procrastination. How do you think about helping people make progress without over-planning?
Nicole: Progress over perfection, always. Tools like OKRs can be great, but only if they serve your team and your context. Some founders use planning as a form of control because setting a goal can feel scary. It means committing. But if you get stuck in the plan and never start moving, you miss the point. Momentum is what actually creates clarity.
Nick: Totally. I used to spend hours in project management tools doing what I thought I "should" be doing. Once I let go of those expectations and started focusing on action, things moved much faster. Now I focus on What’s one thing I can do this week that moves us forward?
On Accountability and Coaching
Nick: For me, coaching has been the most powerful accountability tool. If you're only accountable to yourself, especially from a negative mindset, you can actually slow your growth. It's the difference between growing from scarcity vs. growing from abundance. Thoughts?
Nicole: Well as a coach, I am biased, but I agree. Coaching helps create a culture of real, compassionate accountability. It’s not about pressure. It’s about creating space for people to stretch and fail safely, then learn and grow. Culture isn’t a plan; it’s how you show up every day. Leaders set the tone through their actions, not just their intentions.
On Building Teams and Hiring
Nick: Let’s talk about hiring. I’ve made some bad hires by focusing on credentials rather than mindset. What do you look for?
Nicole: The number one thing I look for is: do they care? Are they passionate, scrappy, resourceful? I can teach someone how to use tools or polish their communication, but I can't teach them to care. That’s not always measurable on paper, but you can feel it. Passion, curiosity, humility—those are the things that make someone a great teammate. Skills can be taught. Caring can’t.
Nick: Couldn’t agree more. I call it mission resonance. If someone resonates with your mission, they’ll overdeliver. They’ll find creative ways to add value. And they’ll stay.
On Product and Problem Solving
Nick: What comes after team? Is it audience, or product?
Nicole: Product, definitely. Not because it has to be perfect, but because it has to be clear. What’s the problem you’re solving, and what’s your unique way of solving it? That’s your product. If your team believes in the solution and can communicate it clearly, you can figure out the rest. If we believe every company exists to solve a problem, then your product is your unique answer to that problem. It doesn’t have to be the perfect answer, just one you believe in and can communicate clearly. From there, we can figure out who to talk to about it.
Nick: Talk more about the actual process of building a great product. Everyone talks about product-led growth these days, but what does that mean? I think it's about getting feedback early and often—doing user interviews, having calls, listening to people. Good data comes from listening, and eventually, the product starts to shape itself. Then, if it's great, it creates buzz on its own and grows without much need for marketing or sales.
Nicole: You have to start open. Listening is such an underrated skill in product development. Don’t go in with a rigid idea. Start by understanding the problem and listening—deeply. Founders often think they already know the answer, and that makes it hard to really hear feedback. But if you let customers tell you what they need, and you're open enough to actually hear it, the product becomes obvious. Just start by building what they’re already asking for.
On Prioritization and Focus
Nick: Once you have some traction, you hit a new challenge: prioritization. That’s where I failed before. I had good ideas and vision, but I didn’t focus. I tried to do too many things at once. If I had just picked one thing and done it really well, it could have been a win. How do you think about prioritization?
Nicole: Lack of focus is the top reason startups fail. As founders, we think ahead—it’s what makes us start companies in the first place. But that future vision can clash with what’s driving value right now. I try to separate those two buckets: what serves today’s urgent customer need, and what invests in future growth. You might spend 80% of your time on today and reserve 20% for the future. Be explicit about that. I always say: let today fund tomorrow. Serve the current need. Invest 20% in future bets, but don’t let those derail the now. There’s magic in focus. Don’t let your long-term vision disrupt what pays the bills today.
Nick: That makes sense. Short-term wins can compound, and eventually, you’ll have the resources to go after bigger, future bets.
On Saying No
Nick: Saying no has been something I’ve had to learn. I used to say yes to everything. I realized I needed a creative side project, something with no outcome attached, just to stay inspired. But too many yeses? That leads to scattered energy. What’s your take?
Nicole: I work on this a lot with clients. One reframe that’s helped a lot of people: when you say "no" to something, you’re actually saying "yes" to something else. Try listing everything you want to say yes to, then prioritize those yeses. That way, your no is not rejection—it’s just honoring a more important yes.
Nick: I love that. It’s not about what’s unimportant; it’s about what’s most important. When I lose sight of that, I lose clarity across the board. But when I remember my "why," everything else fades into the background.
Nicole: Exactly. And a lot of the things we feel pressured to say yes to are driven by external shoulds. When you anchor to your own vision and priorities, it becomes easier to say no with confidence.
On People Development
Nick: We talked about product and priorities, but the other half of the equation is people. A huge mistake I made was over-hiring. Later, I realized that one really strong hire could outperform five average ones. The right person keeps growing and can do multiple roles at a high level. How do you think about developing people?
Nicole: In tech especially, we overvalue individual contribution and undervalue people management. Startups begin with solo founders, so leadership becomes an afterthought. But real people leadership is about direction and cohesion. It’s not just tallying up what each person does. It’s about getting everyone moving in the same direction and creating a culture where they bring their best ideas forward.
Nick: Right—it’s the collective performance, not just the sum of individuals.
Nicole: Exactly. Leadership is the rallying force. And with AI doing more of the task-level work, people skills and emotional intelligence are becoming the true differentiators. Tech can do the IQ part; we bring the EQ.
On Leadership and the Future with AI
Nick: What do you think good leadership looks like now?
Nicole: Well, it used to be about having the loudest voice in the room. But today, powerful leadership often looks quieter. It’s about lifting others up, empowering your team to lead. I love leaders who operate from the back of the room. The people they mentor grow, lead, and bring their own ideas to life. True leaders help build more leaders. That’s influence.
Nick: And where do you see all of this going—product, people, AI?
Nicole: I think we’re entering a phase where startups can operate at scale with small, high-impact teams. AI is helping us move faster and do more with less. So every human hire matters more. The teams that win will be the ones who combine speed and smarts with emotional intelligence, deep empathy, coaching, and clarity.
Nick: Thank you. This was great - super insightful!
Nicole: Of course, very happy to be here! Thanks for having me!
If you’d like to hear more from Nicole Kelley, you can find her at nicole-kelley.com. Or email her at hello@nicole-kelley.com.