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.

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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.

There’s no greater professional joy for me than building a product people love alongside a small team of smart and dedicated people. Owning your own destiny, inspiring others to join your mission, and hitting milestones you’ve set for yourself is addictive. 

Before diving in, ask yourself: Am I ready for a marathon, not a sprint?

Question 2: Is this the right season of life to support this endeavor?

Startup life requires a commitment unlike any other job. You’re always on, constantly making decisions when ambiguity is high and no set playbook can guide you. If you’re working in AI, the ground is shifting under you so constantly that changes in model performance, underlying costs, and competition can fundamentally alter your business at a moment’s notice. 

You have to keep a steady pace and be patient—important skills that are often gained through years of experience.

As such, I think of life as having seasons. Sometimes you take a lower-paying job to gain valuable experience. At other times, you choose a less exciting but more stable job to build a financial cushion. Founding a startup works best in a season of life when you can afford to take calculated risks.

This might be earlier in a career before you have a mortgage and kids, or it might be later when you have more savings and can afford to take a leap. Throughout my career, my partner and I have taken turns doing more and less risky moves in our professional choices to both support each other. He works in finance—another tough industry—so compromises, communication, and mutual support have let us succeed individually and as a family throughout various seasons of life.

For example, I joined Trello when he had a stable job. A few years in, when Trello was acquired by Atlassian, I knew I had found better job security. This allowed my partner to take a risky career leap. A few years later, when I was deciding what was next, he was in a more stable position that allowed me to choose the entrepreneurship route again. We discuss our career moves as partners to determine that they’re the right moves—at the right times— for our family. 

Ultimately, you can make a startup work in any season of life. It’s more of a mindset to understand what’s ahead, what you’re signing up for, and the associated opportunity costs.

Ask yourself: Does this season of life support the level of risk and commitment a startup demands?

Question 3: Is the opportunity cost acceptable to me?

When I was in business school, an entrepreneurship professor once put me on the spot during class. She asked how much money I could make in a corporate job. 

“Six figures,” I said. 

Then she asked how much I was making at the time, working on a startup. 

“Zero,” I admitted. I was building Matchist while attending business school full time—mostly to make my immigrant parents happy with an advanced degree.

Her point was clear: Being a founder often means sacrificing immediate comfort and financial stability. You might go from making no money to little money to decent money—and, in the best-case scenario, life-changing money down the road.

Opportunity costs are lower earlier in your career. Later, the trade-offs can be significant. You might pass on an executive role with a hefty salary and equity to pursue your vision. For me, it’s a calculated risk. In Russian, we say, “Those who don’t take risks don’t drink champagne.”

At the same time, those called to entrepreneurship who pass on the opportunity earlier in life may feel more prepared later: There’s a greater opportunity cost to not pursue a startup when you’re more experienced and have lots of support.

My Hoop cofounder, Brian, also came from an immigrant background, but he went to law school instead of business school. He always wanted to follow in his entrepreneurial father’s footsteps but never saw an opportunity until later in his own career. With a decade of corporate legal experience, he joined Trello at its Series A round and ran the operations, legal, and finance departments until its acquisition (and beyond). He knew the next step was to take on the cofounder role himself, which led him to join me in starting Hoop.

While the opportunity cost of a higher salary can be potentially greater later in a career, the ultimate bet is to bet on yourself.

Ask yourself: Can I accept the trade-offs and uncertainty in pursuit of something potentially greater than a steady paycheck?

Question 4: How passionate am I about the problem I’m solving?

Some people say the industry or problem you’re solving doesn’t matter—it’s the team or opportunity that counts. But over time, I’ve seen those people learn the hard way: You must care deeply about the problem you’re solving. Whether you’re doing so with new technology like AI or with an innovative business model, the underlying problem absolutely has to get you excited.

As a founder, you live and breathe your customers’ pain points. Building the right solution requires an intimate understanding of their challenges. Passion isn’t optional; it’s essential. Consider that you’ll be spending the next decade solving this problem and passing up on numerous opportunities in the process. You have to wake up every morning excited about what you’re doing and energized by the product you’re building. This has been true for me whether it was helping small business owners at FeeFighters, matching entrepreneurs and engineers at Matchist, or helping people be organized and do their best work at Trello and Hoop.

Founders often end up building in the same space over and over, or pivoting a different idea into a familiar space, because they have insider knowledge and experience with that problem space over time. You have to know what you’re passionate about, and that’s often where you develop your greatest expertise and have a greater chance of success. 

For example, the founders of the cloud security firm Wiz, the fastest-growing SaaS startup ever, had already sold a cloud security startup to Microsoft and wanted to try a new venture. But where did they end up after ideating? Back in cloud security with Wiz. It’s what they knew and felt passionate about.

Sometimes a technological breakthrough allows someone with deep experience in a problem space to innovate faster. This happened with me and Hoop: We pivoted our startup into a space we knew intimately—project management—after seeing the advancements in AI that allowed us to tackle the problem in a new way.

Ask yourself: Am I willing to dedicate years of my life to solving this problem? Will I still care about it when times get tough?

If it’s time, take the leap

The decision to start a company is daunting, full of fears both personal and professional. In the age of AI—when so much seems possible—the technology can exacerbate the opportunity, but also the stress and FOMO.

But if you can use this framework to evaluate whether you’re ready for the challenge, you’ll be well-equipped to make the best choice about whether founder life is right for you, and if so, when. If the answers to these questions align with your values and goals, then you might be ready to embrace the founder journey.

Stella Garber is the co-founder and CEO of Hoop, an AI-first task manager Previously, she led marketing at Trello, building the team as its initial marketing hire to Atlassian's acquisition and beyond. 

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