I recently went one-on-one with Joanna McFarland, co-founder and CEO of HopSkipDrive.
Adam: Thanks again for taking the time to share your advice. First things first, though, I am sure readers would love to learn more about you. How did you get here? What experiences, failures, setbacks, or challenges have been most instrumental to your growth?
Joanna: My journey to HopSkipDrive has been shaped by both my professional background and deeply personal experiences that drove me to solve real problems. Before building HopSkipDrive, I started my career in investment banking and then moved into private equity before transitioning into product management after business school. This experience across finance and product gave me a solid foundation for understanding both the business and technical sides of building companies.
But more than anything, what really shaped my growth was being a first-generation American. My mom was just four years old when she came to this country, and the values of education, hard work, and grit were instilled in me from a very young age. Those foundational values became essential when I later faced the challenges that come part and parcel with entrepreneurship. The combination of financial discipline from my banking days and the product mindset I developed at companies like Green Dot and AT&T Interactive prepared me for the complexity of building HopSkipDrive from the ground up.
Adam: How did you come up with the idea for HopSkipDrive and know it was worth pursuing?
Joanna: The idea for HopSkipDrive came from a place of genuine frustration and guilt that I think resonates with so many parents today. As a working mom, I was constantly struggling with the impossible logistics of getting my kids where they needed to be while maintaining my career. The guilt and shame I felt as a parent when I couldn’t be in two places at once was overwhelming.
The lightbulb moment happened at a birthday party where I was talking with other moms, and I realized that every single one of us had some version of the same problem. We were all making impossible choices between our children’s opportunities and our professional responsibilities. That’s when it clicked that this wasn’t just my problem – it was a massive, underserved market need affecting millions of families. When you’re solving a problem that keeps you up at night and you discover it’s a shared pain point across your entire community, you know you’re onto something worth pursuing.
Adam: What advice do you have for others on how to come up with and test business ideas?
Joanna: My biggest piece of advice is to talk to users constantly and really understand their pain points. Don’t just ask people what they want – dig deeper into what problems they’re experiencing that they may not even realize are problems. We spent countless hours talking to both parents and school transportation staff, understanding not just their transportation challenges, but the emotional and logistical complexity of their daily lives.
The key is to get curious about the details. What are people currently doing to solve this problem, even if it’s imperfect? What workarounds have they created? What are they spending money on that doesn’t quite work? Often, the best business ideas come from improving on solutions people are already trying to implement in inefficient ways. And once you think you have an idea, test it quickly and efficiently before building anything elaborate. We validated our concept by literally driving kids ourselves in the early days to understand every aspect of the experience from end to end.
Adam: What are the key steps you have taken to grow your HopSkipDrive? What advice do you have for others on how to take their businesses to the next level?
Joanna: Our growth strategy has always been rooted in experimentation and customer feedback. We started as a B2C business serving families directly, but we quickly learned that schools and districts had the same transportation challenges at scale. The key was being willing to experiment, test, and learn, then scale what worked. This led us to pivot to B2B as we evolved based on what our customers were telling us they needed.
One of the most important pieces of advice I can offer is to listen to your customers, but also lead them. They’ll guide innovation and tell you what they need, but they’re not always aware that their current habits might be part of the problem that can be solved to make their experience dramatically better. You have to balance being customer-driven with being bold about solutions they haven’t imagined yet. The other critical element is building the right foundation for scale – investing in the processes, tools, and systems that enable rapid growth without sacrificing quality or safety.
Adam: What are your best sales and marketing tips?
Joanna: As a founder, you will always be your best salesperson, especially in the early days. There’s an authenticity and passion that comes from the person who built the solution that no one else can replicate. However, you have to recognize that at some point, you can’t scale yourself, so you need to build the processes, tools, and systems that enable your sales team to be as effective as you are.
The most important sales and marketing principle I’ve learned is to listen, get curious, and always stay close to the customer. Your customers will tell you not just what they need, but how to talk about your solution in a way that resonates with others like them. The language they use to describe their problems should become the language you use to describe your solutions. Sales is really about understanding and solving problems, not about convincing people they need something they don’t actually need.
Adam: What are the most important trends in technology that leaders should be aware of and understand? What should they understand about them?
Joanna: It’s clear the biggest trend in technology right now is AI. This is a great example of leaders needing to rapidly adapt and evolve, while lacking perfect information. AI is already generating significant benefits for HopSkipDrive, from product development to operations automation to employee productivity, but it’s also important to use it carefully and to be aware of the risks and limitations. For example, we treat any output as a first draft and continually iterate and refine. The challenge for leaders is to embrace AI’s potential while thoughtfully managing its risks and developing a clear vision for their workforce in this new era.
Adam: In your experience, what are the defining qualities of an effective leader? How can leaders and aspiring leaders take their leadership skills to the next level?
Joanna: Leading a fast-moving organization is incredibly challenging because there are high highs and low lows every single day. What I’ve learned is that as a leader, you should get none of the credit for the good things, but you should take responsibility and accountability for the bad things. This mindset is essential because it really keeps you focused on creating the conditions for your team to succeed.
The most effective leaders I know are those who can navigate uncertainty with grace while maintaining clear vision and communication. You have to be comfortable making decisions with incomplete information, but also humble enough to change course when you get new data. The key to taking your leadership skills to the next level is developing emotional resilience and learning to separate your ego from the outcomes. Great leadership is about creating an environment where others can do their best work, not about being the hero of every story.
Adam: What is your best advice on building, leading, and managing teams?
Joanna: People management is genuinely one of the hardest things you’ll do as a leader, and I think it’s important to acknowledge that upfront. My advice centers on clarity and directness: set clear expectations from the beginning and be explicit about what success looks like. Too many problems, big and small, stem from assumptions and unclear communication.
Feedback is a gift, and you should give it directly and often rather than letting issues fester. Recognition is equally important – make sure you’re giving it publicly and frequently when people do great work. But perhaps the most important advice I can give is that avoiding the hard conversations only leads to much harder conversations later. Address issues early, be honest about challenges, and create a culture where difficult topics can be discussed openly and constructively.
Adam: What are your three best tips applicable to entrepreneurs, executives, and civic leaders?
Joanna: First, you will never have perfect information, so your job is to make the best decision possible with the information you have, but also be willing to be flexible and change direction when necessary. Paralysis from seeking perfect information will kill momentum and opportunities.
Second, culture needs to be defined explicitly and early. It will shape how your team makes decisions, whether you’re explicit about it or not, so you might as well be intentional. Your culture will determine whether people feel empowered to take risks, how they treat customers, and how they handle both success and failure.
Third, take care of yourself and get support through coaching, peer groups, or mentorship. The isolation and pressure of leadership can be overwhelming, and having people you can be honest with about challenges is essential for your effectiveness and your well-being.
Adam: What is the single best piece of advice you have ever received?
Joanna: The best advice I’ve ever received is to ask yourself whether you’re making a decision out of fear or out of excitement when you’re facing a really big, tough choice. That simple question will tell you everything you need to know about whether you should move forward. Fear-based decisions tend to be about avoiding potential negative outcomes, while excitement-based decisions are about pursuing potential positive outcomes.
This framework has guided me through every major decision in building HopSkipDrive, from the initial leap into entrepreneurship to major strategic pivots like shifting the company from B2C to B2B. When you’re making decisions from excitement – even if there are risks involved – you tend to bring more energy, creativity, and resilience to making those decisions successful.
Adam: Is there anything else you would like to share?
Joanna: Building HopSkipDrive has been one of the most challenging and rewarding experiences of my life. What I want other entrepreneurs to know is that the journey is never linear, and the problems you solve will often evolve in ways you never expected.
We started with a transportation problem for families and discovered we were really solving for safety, peace of mind, and the fundamental challenge of getting students safely to and from school in an increasingly complex world.
Trust in your vision, but stay flexible in your execution.
