I recently went one-on-one with Jessica Arredondo Murphy, co-founder and CEO of True Fit.
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?
Jessica: I learned early that progress rarely comes from getting everything right the first time. In a previous role, I took on a project that was bigger than my experience, and I tried to solve every problem alone. The work moved, but the team lost clarity, and I felt the cost of being “the bottleneck.” That setback forced a shift in how I operate. I started treating leadership as a practice of building systems and shared ownership, not personal heroics. The most instrumental growth for me has come from learning to ask better questions, make decisions with imperfect information, and create feedback loops that help a team adapt quickly.
Over time, I have become more comfortable with the idea that mistakes are data. When something does not work, I focus on what it reveals. It is why I dig in to understand problems so deeply. That is where the a-ha treasures are buried: where assumptions were wrong, where communication broke down, and where the process can be improved. That mindset has been a consistent source of resilience and better outcomes.
Adam: How did you come up with your business idea? What advice do you have for others on how to come up with great ideas?
Jessica: Before True Fit, I spent years in retail, close enough to see how much “shopping” is really a human experience, not just a transaction. People want to feel confident, understood, and like themselves in what they buy. But I also saw how often the process breaks down, especially when fit and personal preference are hard to translate online.
The moment that crystallized it for me was personal. My eventual co-founder told me about going shopping with his wife and watching her try on pair after pair of jeans, only to walk out with nothing. She felt deflated, but the truth was simpler: the jeans were just not the right fit for her. I remember thinking, this isn’t just about sizing charts, it’s about confidence. It’s the small heartbreak of spending time, money, and optimism, then ending up disappointed. Hearing it in her words made the gap impossible to ignore.
From there, the idea took shape as a simple question: how do you help people make better decisions with less friction and fewer regrets, especially in a digital world where they cannot try things on? And it has continued to evolve as shopping behavior evolves, from early e-commerce to mobile-first browsing, from social discovery to faster fulfillment expectations, and now into the early chapters of agentic commerce, where shoppers increasingly expect guidance that feels interactive, contextual, and trusted. The details change, but the underlying need stays the same: helping people shop with confidence.
For anyone trying to come up with a strong idea, I recommend starting with friction and emotion. Look for moments where people feel stuck, anxious, or disappointed, and ask what is missing. Then test whether you can describe the problem in one sentence, explain who it impacts most, and show a clear way you can reduce that pain without overcomplicating the solution.
Adam: How did you know your business idea was worth pursuing? What advice do you have on how to best test a business idea?
Jessica: I did not treat it as “Can we build this?” The real question was “Does this solve something people genuinely struggle with?” In retail, you can feel that difference quickly. When a problem is real, it shows up consistently across different people and situations, and it carries an emotional cost, not just an operational one. Fit uncertainty does exactly that. It creates hesitation, frustration, and, too often, regret. That is what made it worth pursuing.
From there, we focused on proving usefulness, not novelty. We asked: can we reduce uncertainty in a way a shopper can actually feel and act on, and can we learn from outcomes so the guidance gets better over time? We paid attention to signals that the problem was urgent, like how often it caused people to abandon a purchase, “bracket” multiple sizes, or stop trusting the experience altogether.
If you’re just starting a business, my advice is to begin with conversations, not assumptions. Talk to as many people as you can who experience the problem, and listen for what’s consistent: the pain point, the language they use to describe it, and the moments when it becomes urgent.
As you learn, map the landscape: what other solutions already exist (including workarounds), where they fall short, and what gaps are still leaving people frustrated. Then ask the most clarifying question: if this stays unsolved, what happens? What does it cost in time, money, confidence, or missed opportunity? When you can answer that clearly, you’re much closer to knowing whether the problem is worth building for.
Adam: What are the key steps you have taken to grow your business? What advice do you have for others on how to take their businesses to the next level?
Jessica: The biggest growth inflection points came from getting disciplined about focus: knowing who we serve, what we do best, and what we are willing to say no to. That clarity improved everything from how we communicated to how we staffed work. Just as important, we built a habit of letting data keep us honest. We paid attention to what people actually did, not just what they said, so we could see what was working, where we were creating friction, and what we needed to learn next.
For others looking to level up, I would start with one habit that never stops: keep talking to your customers and clients. The needs they had when you started the business will not always be the needs they have now. Stay close enough to hear what’s changing, what new problems are emerging, and where you can create additional value for the same customer base.
From there, focus is not just discipline around a roadmap. It is discipline around who you serve, who you should not serve, and where there is an opportunity to expand who you serve. We learned this the hard way. We had to let go of some relationships that were not profitable, even when the client was big. Once we understood our unit economics at a deep, customer-by-customer level, we could focus intently on our ICP (ideal customer profile) and fuel not just growth, but profitable growth.
Adam: What are your best sales and marketing tips?
Jessica: Make trust the objective. Trust comes from clarity, consistency, and follow-through, not cleverness. Part of that is being rigorous about the truth of your product, whatever it is. Do not make claims you cannot stand behind, and do not hide behind jargon when the story is messy or still evolving. There is always nuance and gray area in real businesses, but people can tell when something does not add up, whether you are talking to a boardroom or to everyday customers. If you stay grounded in what you know, what you are learning, and what you can prove, you earn credibility over time.
Practically: lead with a crisp point of view, speak to outcomes rather than activities, and use simple stories that make the value intuitive. On the sales side, I believe in qualification as a form of respect. If you can name what success requires, what you will not do, and where you are still learning, you create confidence, even if it means turning down a deal.
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?
Jessica: Effective leaders combine decisiveness with humility. They set direction, communicate it clearly, and stay open to being wrong. They create psychological safety while still holding a high bar for performance. They also build teams that challenge them. One of the best ways to avoid stagnation is to surround yourself with people who are smarter than you in different ways and then actually empower their decision-making. If everything still has to run through you, the organization can only move at your speed, and your blind spots become everyone’s constraints.
To level up, I recommend practicing three habits: make expectations explicit, give feedback early, and build systems that let the team learn faster than the environment changes. Clear decision rights and real ownership are part of that system.
Adam: What is your best advice on building, leading, and managing teams?
Jessica: Design the team like you would design a product: for clarity, usability, and scale. Define roles, decision rights, and what “good” looks like. Then create routines that keep everyone aligned: simple planning, consistent check-ins, and clear documentation. When issues arise, address the system first. Most recurring problems are not personality problems; they are unclear priorities, unclear ownership, or unclear process.
Adam: What are your three best tips applicable to entrepreneurs, executives, and civic leaders?
Jessica: I would say that the best leaders prioritize clarity over complexity, because a simple, well-communicated plan will outperform a sophisticated plan that no one can execute. They also build feedback loops, because the real advantage is not being perfect, but learning faster than everyone else. And finally, they choose progress over perfection and protect their attention, because perfection is the killer of innovation. One practical way to do that is to look at your calendar and ask where you are spending your time and whether those activities truly move the needle for your customers, your organization, and your team, since unchecked, it is easy to lose time to work that does not move you forward or make you better.
Adam: What is the single best piece of advice you have ever received?
Jessica: “Never waste a good crisis.” Massive failures can feel crippling, but if you lean into the crisis and navigate through it, immense growth and sometimes even breakthroughs can come through the other side.
Adam: Is there anything else you would like to share?
Jessica: If there is one theme that ties everything together, it is this: sustainable success is built through small, repeatable practices. Big outcomes come from doing a few important things well, consistently, over time. And along the way, I would hold on to two operating principles. First, stay curious. Showing up assuming you already know the answer is a fast way to miss what is actually true about your customers, your team, and the problem you are trying to solve. Second, lean into challenges. Some of the skills I value most today came directly from challenges and failures I would never have chosen in the moment, which helped shape me into the leader I am today.
