What drives you to succeed?
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Starting a business can be a tricky business.
Achieving success requires a mixture of grit, guts, talent, and luck in unpredictable proportions. For some, that inherent unpredictability means that the entire endeavor is more art than science, and the risk of failure can be mitigated but not avoided.
If this is how you view entrepreneurship, you’re not wrong: the vast majority of startups never return a dime to their founders.
However, this view is not necessarily correct.
Not all founders fail in the same way. Many find a path to success with a consistency that defies our understanding of the risks inherent in starting a company. What seemingly unfailing founders and CEOs have in common is that they view company building as a process that must be completed. To them, entrepreneurship is simply the business of building a company, and adopting this mindset is one of the most transformative insights for any leader.
Below we explore three particularly powerful variations of this approach to entrepreneurship, all of which have proven their worth.
Founders turn purpose and failure into success
Some people think that entrepreneurship is something you fall into after nothing goes according to plan.
For others, becoming a founder is the culmination of decades of preparation and reflection, and they have no choice but to carve their own path. You’ll hear leaders in this category innately talk about purpose, passion, and perseverance in the face of the most difficult situations. And these are leaders who may stumble on their path to success, but are unlikely to fall.
“At the start, I had no website, no producers, no clients, nothing that you need to run this kind of business,” Oubre Winters Cassiano, founder of workout platform Sweat Sessions, told us during our recent discussion about turning recklessness into success.
“All I had was my ‘why’, and that ‘why’ fueled the grit and perseverance it took to grow Sweat Sessions into the international online community and studio it is today,” Oubre said, reflecting on the drive that kept him going during the most challenging times in his leadership journey.
Knowing your “why” seems like a CEO superpower, and Simon Sinek explains it in great detail in his book, Start With Why:
Starting a business isn’t grueling work that can’t be endured without a clear sense of purpose. In fact, most successful entrepreneurs fell in love with being an entrepreneur long before they became successful. But a clear sense of purpose is what allows founders to get back up after setbacks. It’s this resilience that increases the likelihood of success no matter where you start.
Few people know more about the transformative power of purpose and resilience than Alyssa MacKay, who transitioned from a life spent in foster care to co-founding streetwear brand Beyond Lost and a career as a lifestyle creator with millions of followers.
“It all felt pretty surreal,” Alyssa said, reflecting on the journey that got her to where she is today. “I never had a backup plan for starting a business. I know that the money that covered last month’s rent might not make another cent next week, so my way of playing it safe is to push myself by always taking risks and investing in myself and my business,” Alyssa explained.
If you’re having trouble defining your purpose, you can also turn to frustration.
“I was extremely frustrated with the current state of healthcare,” Dr. Mitesh Rao, CEO of healthcare data ecosystem OMNY Health, recalled in our conversation about what inspired him to start this work.
“I looked high and low for existing solutions to solve the fragmentation of healthcare data. At some point, I realised I needed to strike out on my own and the best way to do that was to leave the healthcare industry altogether and become an entrepreneur,” Mitesh recalls.
While the results may be surprising, there’s nothing magical about purpose, passion, or frustration. Rather, when founders rely on these three drivers, the odds are heavily tilted in their favor.
Just as luck favors the prepared, success comes to those who know not to give up, and the same is true for those who cannot shake the feeling that there is a problem with their name on it waiting to be solved.
Founders can’t let go of a good problem
When it comes to problems, there are two types of people: those who know how to avoid them, and those who can’t stop trying to solve them.
Mathematicians are known to love a good problem, even if it takes them collectively centuries to reach a solution.
There’s an uncanny similarity between founders whose success seems all but certain and mathematicians who won’t let go of a problem until it’s solved: they both start by asking questions that others ignore.
“Why is it that I can buy fresh food for my dog but all my baby food is canned?” Little Spoon co-founder Ben Lewis finds himself asking himself out loud more often than he’d like.
“I was never a baby food expert, but I couldn’t escape the question. Eventually, my co-founder and I succumbed to the need to find an answer and realized there was no reason why parents couldn’t buy fresh baby food. It wasn’t being done yet, so we decided to do it,” Ben recalled of the company’s beginnings.
For founders who are driven by an insatiable desire to find answers, starting a company is the only logical conclusion. There they find something beyond purpose and passion: certainty of direction.
Leaders with confidence in their direction become true forces of nature, and success becomes inevitable, even if they have to rework plans until the equation is right.
Elise Barnes, founder of veterinary staffing company Evette, is a great example of how belief can lead to success.
“I have to admit that I wasn’t even an animal lover before working at Evette,” Elise confessed during our discussion, explaining that her path to leadership began with recognizing a problem, rather than a deep passion for the industry.
“I was drawn into this life because I couldn’t give up on solving obvious problems that others were ignoring. How could it be that the veterinary industry doesn’t have a human-centric hiring process, but the human side does,” Elise explained as we delved into what inspired her to start working with Evette.
Building a business around a problem is an especially powerful approach because it focuses the founding team’s efforts while encouraging them to try new approaches until their initial desire to start a business is fulfilled.
“We had already launched three or four times with different versions of the core idea, and nothing really happened,” Brendan Kamm, CEO of corporate gratitude and gifting platform Thnks, recalled in a conversation about what ultimately led to the launch.
“We wouldn’t be here if we hadn’t been willing to pivot until we found a solution to the problem others were having – not having a way to truly personally express gratitude from afar. We never expected our product-market fit to come together in the way that it did, but we knew we needed to keep trying as long as the problem persisted,” Brendan added.
Founders and investors who set up a company as a business
We tend to overestimate the importance of the individual and underestimate the importance of the team behind them.
Even Steve Jobs, Elon Musk, and Jeff Bezos needed teams to succeed, and there is a fascinating group of founders and venture capitalists out there who know how to use this fact to their advantage.
“Even if the timing is right and the business model is perfect, starting a company can be incredibly hard,” Kevin Reneway, CTO of Pioneer Square Labs, which has raised tens of millions of dollars in venture funding for many of the startups in its portfolio, said during our discussion of how the company has formalized the business of building successful companies.
“The reason most startups don’t reach their potential is because they don’t have the right team on their side. That’s why we run a Startup Studio, which combines great ideas with capital, people and technology to de-risk startups and steer companies in the right direction,” Kevin elaborated.
PSL’s approach also involves equipping kids with the right tools, even if they have to build the tools themselves, as they recently did with JACoB AI, an open-source AI agent that streamlines the software-building process.
Adam Sharkawy, co-founder and managing partner at Material Impact, is also a believer in the power of optimizing the company-building process.
“We build our company in a very structured way,” Adam explained.
“We have an ecosystem of core teams that we can deploy to any company in our portfolio, with clear objectives and an exit point when their skills are no longer needed. Each engagement benefits not only the expert team, who learn how to build companies more efficiently, but also the founders,” said Adam, discussing the positive feedback loop that emerges from the Material Impact approach.
What PSL, Material Impact and their peers have discovered is that there are huge benefits to be gained by treating company formation as a business in itself.
Founders and VCs who internalize this approach leave less to chance after each iteration, ultimately making each venture more about trial and error than gambling.
For those still exploring their path to entrepreneurship, it will be comforting to know that practice and dedication can complement a passion for purpose and problem-solving.
