Achieving success in business requires a mix of ambiguity, grit, skill, and luck in proportions that are hard to predict. For some, the inherent unpredictability suggests that the whole enterprise is more art than science, where the risk of failure can be mitigated but not entirely avoided.
If this is your view on business, you are certainly not wrong; the vast majority of startups fail to return a penny to their founders.
However, this perspective is not entirely accurate either.
Not every founder is equally likely to fail, and many find their way forward with a consistency that challenges our understanding of the inherent risks of business. The common factor among founders and CEOs who seemingly cannot fail is that they approach building companies as a process to be perfected. For them, entrepreneurship is simply the business of building businesses, and adopting this mindset is one of the most transformative insights for any founder.
Join us below as we explore three particularly powerful variations of this approach to business, all with proven results.
Founders Who Transform Purpose and Frustration Into Success
For some, business is something to fall into after nothing else has worked out.
For others, becoming a founder is the culmination of decades of preparation and reflection that leave no other choice than forging one's own path. You will hear founders belonging to this category speak in terms of purpose, passion, and perseverance against even the most daunting odds. Here, we find leaders who might stumble but are unlikely to fall as they progress toward success.
"In the beginning, I didn’t have a website, suppliers, customers, or anything else you need to run this kind of business," Aubre Winters-Casiano, founder of the workout platform Sweat Sessions, noted in our recent conversation about turning raw ideas into success. Reflecting on what drove her forward during the toughest times of her leadership journey, Aubre shared how she integrated Sweat Sessions into the global online community and studio it is today.
Knowing your 'why' seems to be a CEO’s superpower, something Simon Sinek elaborates on brilliantly in his book "Start With Why."
It’s not that entrepreneurship is hard work one cannot endure without a clear sense of purpose. On the contrary, most who succeed in business fall in love with being an entrepreneur long before they succeed in it. However, a clear sense of purpose gets founders back on their feet every time they are knocked down. It is precisely this kind of resilience that improves the odds of success regardless of where one starts from.
Few understand the profound power of purpose and resilience as intimately as Alyssa McKay, who lifted herself from a life spent in foster homes to a career as the co-founder of streetwear brand Beyond Lost and a lifestyle creator with millions of followers.
"It's all been somewhat surreal," Alyssa noted as we traced the path she has taken to where she is today. "I've never had a Plan B for entrepreneurship. I know that what paid my rent last month might not pay another dime next week, and the way I play it safe is by constantly taking risks and investing in myself and my business," Alyssa explained.
If you’re struggling to define your purpose, you can lean on frustration just as well.
Mitesh Rao, CEO of healthcare data ecosystem OMNY Health, recounted during our talk about what got him started. "I searched everywhere for a pre-existing solution to the fragmented state of healthcare data. Eventually, I realized that I would need to take action myself, and the best way to do that would be by leaving medicine altogether to become an entrepreneur," Mitesh reflected.
Although the results can be extraordinary, there’s nothing magical about purpose, passion, or frustration. Instead, when founders rely on this trio of drivers, they effectively steer the outcomes of fortune in their favor.
Just as luck favors the prepared, success reaches those who don’t know how to give up. The same goes for those who can’t shake off the feeling that there’s a problem with their name on it waiting to be solved.
Founders Who Can’t Let Go of a Good Problem
There are two types of people when it comes to problems: those who know to avoid them and those who can’t stop themselves from trying to solve them.
Mathematicians are known for their love of a good problem, even if it means spending centuries to reach a solution.
There’s an uncanny resemblance between founders who seem almost destined to make it and mathematicians who can’t let go of a problem until it’s solved. For starters, both begin by asking questions others overlook.
"How is it that we can buy fresh food for our dogs, but everything for babies comes in a can," Ben Lewis, co-founder of Little Spoon, found himself asking more often than he liked.
"I was by no means a baby food expert, but the question just wouldn’t let me go. Eventually, my co-founder and I succumbed to the need to find an answer, and we realized there was no reason why parents shouldn’t be able to buy fresh baby food. It just hadn’t been done, which is why we decided to do it," Ben reflected on the company’s origins.
For founders driven by an insatiable need to find an answer, business is the only logical conclusion. Here we find something that goes beyond purpose or passion; a conviction of direction.
Founders who find themselves equipped with a conviction of direction can be true forces of nature, with success being a certainty even if reaching it means going back to the drawing board until the scenarios align.
Elise Burns, founder of veterinarian staffing company Evette, is a great example of how conviction can lead to success.
"I have to admit that I wasn’t even an animal lover until I got started with Evette," Elise confessed during our conversation on how her path to leadership began by identifying a problem rather than a deeply held passion for the industry. "What pulled me into this life was my inability to let go of solving an obvious problem others were ignoring. How could it be that the veterinary industry didn’t have a human-centered recruiting process while the human side did," Elise explained as we delved deeper into what got her started with Evette.
The reason why building a business around a problem is an especially powerful approach is that it focuses the founding team’s efforts while also inviting them to try new approaches until the initial itch to get started has been scratched.
"We had already launched three to four times with different versions of our core idea, but nothing really took off," Brendan Kamm, CEO of enterprise appreciation and gifting platform Thnks, recalled as our conversation turned to his views on why they eventually succeeded in getting off the ground.
"We wouldn’t be here without our drive to pivot until we found a solution to what we knew to be a problem others were having; the lack of truly personal forms of expressing gratitude over a distance. I could have never guessed that our product-market fit would come together the way it did, but I knew that as long as the problem persisted, we’d need to keep trying," Brendan added.
Founders and Investors Who Build Businesses As A Business
We tend to oversell the importance of individuals and underplay that of the team behind them.
Even Steve Jobs, Elon Musk, and Jeff Bezos needed their teams to make it, and there’s a fascinating group of founders and investors who know how to leverage this fact to their advantage.
"It can be incredibly difficult to get a company off the ground even if the timing is right and the business model is flawless," Kevin Leneway, CTO of Pioneer Square Labs, which has raised millions in venture funding for numerous startups within their portfolio, stated in our conversation on how their organization has formalized the business of building successful companies.
"The reason why most startups fail to reach their potential is that they never get the right team behind them. This is why we run a startup studio that lowers the risk of entrepreneurship by combining great ideas with funding, operators, and technical talent to get the company on the right track," Kevin elaborated.
PSL’s approach also includes equipping their startups with the right tools, even when it means building them themselves as they recently did with JACoB AI - an open-source AI agent that streamlines the process of building software.
Material Impact’s co-founder and managing partner Adam Sharkawy is another believer in the power of systematizing the process of building companies.
"We build companies in a highly systematized way," Adam explained. "We have an entire ecosystem of core teams that are ready to be deployed to any company within our portfolio with clear goals and exit points for when their skills are no longer needed. Each engagement benefits the founders as much as it does the expert teams in learning how to build companies more efficiently," Adam noted as we discussed the positive feedback loops that arise from Material Impact’s approach.
What PSL, Material Impact, and their peers have realized is that there are outsized returns to be had by treating company formation as a business in itself.
Founders and VCs who have incorporated this approach take on less risk after each iteration, ultimately making each venture less of a gamble and more of a trial run.