There might be only one Rome, but there are many ways to get there.
In a similar manner, entrepreneurship is less of a marathon and more akin to filling your bucket with candy on Halloween. If you’re in the right neighborhood, there’s enough candy for everyone, and the path each leader takes is unique, built on personality, past experiences and flashes of inspiration.
This is why business writing that encourages leaders to follow prescribed “best practices” can feel as rigid, given how they are simply examples of one thing that worked.
Whether it’s doing things that don’t scale or building what you’re passionate about, the truism-heavy approach to entrepreneurship can miss the nuanced reality that successful founders actually face.
In the end, success in entrepreneurship doesn’t come from following a blueprint, although having a plan and the capacity to execute on it is essential.
Entrepreneurship, when properly understood, is much more about letting curiosity, resilience, and the market lead the way. Some founders find their way to Rome by addressing their personal challenges, while others step in to serve others. What is common to all successful CEOs is the ability to listen to themselves as well as the market, navigating by instinct refined throughout their lives, and, yes, taking some big leaps of faith along the way.Let’s dive into a few unique paths to success that prove that there’s never just one way to making it in business.
Sometimes Success Is Personal: Jack Savage’s Journey with Everyday Dose
Jack Savage started Everyday Dose with a simple, deeply personal insight: the need for a coffee that actually worked with his ADHD, rather than against it.
His journey to build the company was an intuitive exploration of finding what works from day one, with each step driven by his own experience rather than market research or business plans.
“Everyday Dose began as a solution I made for myself,” Jack reflected on the beginning of the D2C alternative coffee brand.
“I wanted to stay focused without the crash coffee always gave me, and giving up that taste just wasn’t an option,” Jack continued.
Fueled by curiosity, he created a formula combining low-acidity coffee with adaptogens, mushrooms, and nootropics.
He took a bold step by running a Facebook ad to gauge interest, well before he had created the company his clients know today.
The market response was immediate, validating his intuition and laying the groundwork for what would become a career instead of an act of self-medication.
By focusing on something that resonated with him on a personal level, Jack tapped into a niche that others overlooked.
He approached the market with a solution that was personal instead of trying to change the coffee industry wholesale, and he’s found success by staying true to his vision, developing products that support his own well-being.
“The ingredients in Everyday Dose have allowed me to regain control of my life, and I’m on a mission to help others feel more in control of their energy,” he recalls, noting how this authenticity resonated with customers, many of whom were searching for a similar solution themselves.
Making All Fun and Games Make Business Sense: Kyle and the Onewheel AdventureKyle Doerksen’s path to success with Onewheel is a testament to the power of play and taking fun seriously as guiding principles for business modeling and product design.
The fact that Kyle launched Onewheel as an experiment, inspired by his own fascination with motion and design, was pivotal to getting the company to where it is today,
“If you asked people if they’d want a one-wheeled skateboard, they’d have no idea,” he shares, before noting that “this isn’t a product anyone in their right mind would have created based on what the market thought would have mass appeal.”
After a successful career spent designing toys and products centered on fun, Kyle decided to follow his gut and build something he himself would want to experience.
“We started with a few people asking us to build it, and that was enough for me to build a business around this,” Kyle added.
The initial concept was both playful and ambitious, and what he set his sights on was making a high-quality vehicle that could have the potential to become a sport.
Unlike founders who spend years perfecting a business plan, Kyle was content to test, iterate, and see where the product would take him.
While some might have considered the project too niche, Kyle’s intuition about the product’s appeal seems to have been accurate, with even the X Games getting a taste of the product earlier this year.
His decision to price it as a premium product ensured that it was seen not as a gadget, but as a quality item for a specific kind of consumer who shares his view on exploring the world with curiosity.
“I didn’t want to make a toy,” he says. “I wanted something that makes adults feel like kids, challenging them to master it.”
This sense of joy and challenge has helped Onewheel carve out a unique space in the crowded personal mobility market, showing that staying close to one’s original inspiration can lead to powerful results.
Making Quality Work For You: George Pfeffer and DPR ConstructionFor George Pfeffer, CEO of DPR Construction, the journey into leadership was less about crafting a novel product than it was committing to quality and safety.
The company was recently named as one of the best companies to work for among private companies; a feat that is explained by George’s views on the importance of trust and reputation.
“We live on reputation, relationships with clients, quality, safety, and how efficiently we can do the work,” he explains, before noting that in the construction industry’s history, quality has been too often traded off for speed or budget.
As opposed to Everyday Dose or Onewheel, there is nothing personal about the story here, in fact, the focus is decidedly on those George and his team serves.
George explains that this commitment to clients and what they get from each engagement has been core to DPR’s approach from the beginning, showing how success can follow from something as simple as doing the best work one can.
The key to success with a business model such as this is learning what clients want, and how to deliver it exactly like they want it.
George himself began his career with hands-on experience and a willingness to listen; a quality that serves him well as he leads a workforce that balances technical construction expertise with elements of the service industry when it comes to satisfying clients.
“You can’t be a contractor without having hope,” he notes, reflecting on how intrinsic optimism and faith in people has kept DPR on the right path. This grounded, collaborative approach has allowed DPR to navigate the unique challenges of construction and maintain strong, lasting relationships in an industry that often lacks stability.
From Pivoting to Thriving: The CEO’s Pivotal Choices at SureOne response to the multithreaded nature of entrepreneurship is to retain the ability to reconsider one’s path at a moment’s notice.
The journey of Sure, a digital insurance platform, demonstrates that finding the right path often involves course corrections, even if it involves pivoting the entire team to an entirely new approach.
As Sure’s CEO, Wayne Slavin notes, the company initially started as a direct-to-consumer mobile app to sell insurance, such as buying life insurance before boarding a plane.
“I never gave up on the idea, but in the end I couldn’t shake off the feeling that we were going uphill while we could have been running free towards the finish line,” Wayne reflected in our recent discussion on how the company made the jump to becoming a software platform that allows consumer brands and insurance carriers to sell insurance digitally on their own using Sure’s technology.
“Our pivot was based on a skunkworks-type approach, we built a product internally that we realized could outsell what we were initially doing and we ran with it,” Wayne explained.
This pivot wasn’t just strategic; it reflected Wayne’s responsiveness to market shifts and a willingness to listen to what his team, and their customers, were telling him even if the message wasn’t always delivered explicitly in words.
In hindsight, Wayne notes that the pivot to embedded insurance was a critical turning point, one that required the humility to rethink the company’s direction entirely.
“Being able to change course wasn’t just an option—it was essential,” he recalls. By embedding insurance directly within platforms, Sure expanded its reach and cemented its value to partners who might not have otherwise considered them.
This flexibility is a reminder that even the best plans sometimes require adjustments, and leaders who can recalibrate without losing momentum often come out on top. When there are as many roads to Rome as leaders, it’s important to keep your commitment to the goal strong, while keeping the processes and paths changeable.