Is Founding a Startup Right for You?

At a time when AI is reshaping the startup landscape and making it seemingly easier than ever to build products, the age-old question remains: Are you ready to become a founder? Stella Garber's piece—the fourth in her series on business frameworks—dives into the four questions every aspiring founder needs to answer before taking the entrepreneurial plunge.Whether you're contemplating your first venture or (like Stella) your fifth, you'll find insights about timing, opportunity costs, and the lasting commitment required for success.—Kate Lee

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If you want to trigger a founder, ask, “How’s everything going?”

The answer is usually silence followed by a strained, “Good!”

Even when things are great, there’s always a chance that something—a banking crisis, a macro event, new competition—could derail everything. You need to know what you’re getting into, and all the chaos it could bring, before starting. The most important question to ask yourself, then, is: How do you know if founding a startup in the age of AI is the right path for you?

Take it from me as someone who has lived this question.

Throughout every career transition, I’ve chosen entrepreneurship in a methodical way. I’ve asked myself the same questions over and over, managing to ignore statistics like, “Don’t 90 percent of startups fail?” (Spoiler alert: Not true.) 

But in the age of AI, or at any great moment of technological change—like the dawn of social and mobile before it—it helps to have a framework to evaluate if being a founder is the best choice for you. AI makes it easier for people without technical expertise to build products, but it hasn’t yet changed the trajectory of the typical startup and the questions you need to ask yourself. In that spirit, let’s explore the four most important questions for aspiring founders, so you can determine if you’re ready to become one yourself.

Question 1: Am I willing to spend the next 10 years of my life doing this?

People often misunderstand the timelines of startups. When venture capitalists make a seed investment in a company, they want an exit in 7–10 years. But the journey can often be much longer than that. During these years, running a startup is an intense and unrelenting trek. It’s like signing up to get punched in the face—voluntarily—over and over again.

Everything takes longer than expected. Even when things are going well, founders must deal with constant challenges. For every up, there’s a down—or two, or three. For every great success, there are unexpected roadblocks. 

In my first year at Hoop, the joy of being able to raise money and build a team was counterbalanced by the horrific fear that we’d lost everything in the Silicon Valley Bank (SVB) collapse. Don’t worry—it all worked out for us. Rather than going with a “risky” neo-bank, we’d gone for the “safer,” well-known banking partner. Little did we know that behind the scenes, SVB was on the brink of collapse. And for a few days after it announced its epic shutdown, we thought we had lost all of our hard-earned money. Luckily, thanks to swift action by the U.S. government, our money was safe.

Bank failures are few and far between, luckily, but starting a company comes with unknown risks. Many founders admit that if they’d known how hard it would be, they might not have started. Despite that, many of them go back time and again to try their hand at yet another startup. I certainly have—and now I’m on my fifth.

For me, entrepreneurship never felt like a choice but a calling. I come from an immigrant family with business ambition in our blood: My grandfather ran a trucking company in the Soviet Union, starting as a driver when he was only a teenager. My father arrived in the United States in the 1980s with nothing but his education and his drive and started a successful medical practice. At home, childhood lessons often revolved around the American Dream: rejecting the status quo and taking advantage of opportunities I’d never have if we hadn’t emigrated.

In my career, I’ve always been either a founder or an early employee. I was a founding member of a fintech company called FeeFighters and sold it to Groupon in 2012. Then, I ran a community and events business focused on telling entrepreneurs’ stories, before starting a marketplace for technical talent called Matchist that I sold to a venture studio. After that, I joined Trello as its first marketer, leading a team from Series A to its acquisition by Atlassian and for years afterward.

Now, I’m the cofounder and CEO of Hoop, a venture-backed, seed-stage task management startup using AI to help people aggregate all of their tasks in one spot automatically. We’re helping people answer the age-old question: How do I make sure I’m doing everything I need to do?

Oh, I’m also 38 years old, a wife, and a mother to two young kids.

I know well that being a founder is one of the biggest commitments you can make. It’s an all-consuming adventure with an insane amount of stress. There’s plenty of upside—especially in the age of AI—but no guarantee of success.