EP 293 – Steven Rothberg: If a Customer Wants to Pay More, Let Them

Steven Rothberg - Paper Napkin Wisdom - If a customer wants to give you more money, find a way of making that happen. $$$

When you sit down with someone like Steven Rothberg, Founder and Chief Visionary Officer of College Recruiter, you expect to hear insights about hiring, technology, and the future of work. What you might not expect is a napkin that sums up decades of wisdom in a sentence so straightforward it almost sounds too simple: 

“If a customer wants to give you more money, find a way of making that happen. $$$” 

At first glance, it feels like sales advice. But during our conversation, it became clear that Steven’s napkin is less about sales tactics and more about mindset. It’s about curiosity, listening, and the courage to grow your business in partnership with your customers instead of in isolation from them. 

The Origins of the Napkin 

Steven explained that this napkin wisdom didn’t come from a single “aha” moment but from years of conversations with clients. Over time, he noticed a pattern: customers would ask for things that weren’t on the official menu. Sometimes they wanted a slightly different feature. Sometimes they asked for more robust reporting or a more targeted audience. And sometimes, they were just willing to spend more if Steven’s team could meet a need better than anyone else. 

Many leaders instinctively shy away from these requests. They think: “That’s not what we do,” or “We can’t risk diluting our focus.” But Steven saw these questions differently. Each one was a clue. Each one was a chance to say, “What if we could?” 

This perspective became part of the DNA at College Recruiter, and it’s one of the reasons the platform grew from a small niche job board into one of the most respected platforms connecting students and employers worldwide. 

Why Leaders Miss These Signals 

One of the most striking parts of our discussion was Steven’s take on why so many entrepreneurs and leaders overlook these opportunities. Too often, businesses are so locked into their product roadmap that they forget the roadmap is supposed to serve the customer—not the other way around. 

Steven told me that some of his biggest breakthroughs came not from what his team had planned, but from what clients asked for. He shared examples where a client’s request sounded small at first but eventually evolved into a scalable new revenue stream. Instead of brushing off the request, he leaned into it, curious about how to make it work. 

It’s not about chasing every shiny object. It’s about noticing when the customer is signaling that they want to go deeper with you. 

The Win-Win Philosophy 

The other nuance of Steven’s napkin is that it’s not about upselling for the sake of upselling. He made it clear: customers will only happily pay more if they feel like they’re getting more. The transaction has to be a win-win. 

At College Recruiter, this meant building systems to measure and deliver additional value whenever they expanded offerings. If a client wanted to pay more to reach a specific audience segment, the team didn’t just take the check—they figured out how to build the tools and reporting that would ensure the client saw results. 

That’s the kind of approach that transforms a customer from a one-time buyer into a long-term partner. 

Curiosity as a Growth Strategy 

One of my favorite parts of this conversation was when Steven talked about curiosity. For him, curiosity wasn’t just a trait—it was a growth strategy. When a customer asked for something new, he didn’t immediately think of reasons why it couldn’t work. Instead, he asked questions. He explored possibilities. 

This curiosity often led to innovation, and it reinforced a culture at College Recruiter where the team felt empowered to ask: “What if we could?” 

In the long run, that curiosity helped Steven and his team build a company that stayed relevant even as the hiring landscape shifted dramatically. 

The Lesson for Entrepreneurs and Leaders 

Steven’s napkin wisdom is deceptively simple, but it’s also incredibly powerful. Too many leaders think growth comes from pushing harder on the products they already sell. In reality, some of the best growth comes from noticing when customers are asking for more and then having the courage and creativity to make it happen. 

It’s not about saying yes to everything. It’s about knowing which yeses align with your mission and create real value. That’s how you build revenue, loyalty, and a reputation for being the kind of company that listens. 

5 Key Takeaways (with Take Action steps) 

1. Customers Signal Opportunities—Listen Closely 

When a client hints at spending more, it’s rarely random. It’s a signal of untapped value. Steven’s success came from leaning into those signals. 

Take Action: Log every client request that goes beyond your current offerings. Review them monthly to spot patterns worth pursuing. 

2. Expand Without Dilution 

Saying yes doesn’t mean losing focus. Steven’s team always tied new services back to their mission of connecting students and employers. 

Take Action: Run all new opportunities through a mission filter. If it doesn’t clearly align, let it go. 

3. Small Changes Can Unlock Big Revenue 

Sometimes the difference isn’t a brand-new product—it’s a tweak in packaging or pricing. 

Take Action: Review your pricing and packages quarterly. Ask: “Where are we making it hard for customers to buy more from us?” 

4. Win-Win Is the Only Way 

Upselling only works if the customer walks away feeling like they got more. Otherwise, you’re burning trust. 

Take Action: Add a “value check” to your process. Ask customers: “Does this feel like it gives you the value you need?” 

5. Curiosity Beats Complacency 

Steven’s curiosity fueled innovation and growth. It helped his company evolve alongside the market. 

Take Action: Make “What if we could?” a team mantra. Use it to spark brainstorming sessions whenever a client makes a request. 

About Steven Rothberg 

Steven Rothberg is the Founder and Chief Visionary Officer of College Recruiter, the leading job search site for students and recent graduates. For more than 25 years, Steven has been a voice for equity and access in early-career hiring, helping employers and candidates connect in more meaningful ways. You can connect with him on LinkedIn. 

Final Thought 

Steven’s napkin reminds us: growth isn’t always about what we want to sell. It’s often about what the customer is ready to buy. When customers invite us to grow with them, our job is simple—don’t get in the way. Find a way of making it happen. 

Now it’s your turn. Grab a napkin, jot down your takeaway from Steven’s wisdom, and share it with #PaperNapkinWisdom. Because the next big idea might just start with the simplest customer request.