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I just raised $30 million. Here are 4 questions I wish I’d asked before I started my business

Entrepreneurship isn’t all glamour and wealth creation, even when things are going well, a founder writes.

I just raised $30 million. Here are 4 questions I wish I’d asked before I started my business
[Source images: ChrisGorgio/iStock; sam74100/iStock]
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It’s time to change the thinking that starting a business is everyone’s business. As Y Combinator president Michael Seibel recently told me: “I used to think my job was to convince people to start companies. Now, everyone wants to start a company, so I think my job is to talk them out of it.”

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Seibel’s not overstating the surge in entrepreneurship: Over the past decade, the number of businesses less than a year old has grown by nearly 50%. More than 300 schools now offer entrepreneurship studies. Compared to baby boomers, millennials and Gen-Zers are 188% more likely to start their own business. For many, nothing sounds better than being your own boss—the reason 29% of surveyed small-business owners started their business. One in six cited “following their passion” as their primary motivator.

Being your own boss, following your passion: These sound like compelling reasons for starting a company . . . until five years into the journey you find yourself facing a pandemic, an economic downturn, and a supply chain disruption, and raising a Series C round of venture capital. This was the stark reality of my past year as CEO and cofounder of Tovala, a smart-oven-paired subscription meal service. (Joe Mansueto, the owner of Fast Company, is an investor.) Reflecting on the last 12 months and Tovala’s history to date, I came up with four questions I wished I’d asked myself—and all aspiring entrepreneurs should—before starting a business.

Are you prepared to have your business fail?

This is not a hypothetical, worst-case scenario question. It’s a real and frightening possibility. Around 90% of startups fail. Even the 10% that survive still endure multiple near-death experiences. Living on the precipice is startup life. Whether it’s coming mere hours from shipping your first product only to realize it has potentially catastrophic flaws or a lead investor pulling a term sheet one day before the expected close date, at Tovala we’ve had to stare potential failure in the eyes more times than we’d like to admit. Are you willing to put time, work, and resources into a business that could combust at any point, whether that’s in the early days or many years into its existence? And, just as important, are you ready to live with that possibility weighing on your mind day in and day out? Part of being a successful entrepreneur is living with the specter of failure—and using it as fuel instead of fear.

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Can you make sacrifices in your personal life?

When you’re starting a business, the lines between personal and professional life blur. You are the company’s chief strategist, marketer, salesperson, and, for me, the first person to prepare and deliver Tovala Meals. And, throughout our story, my (now) wife and many of the partners of our small team have been regularly involved in getting us off the ground and keeping us afloat, from helping pitch Tovala at events to packing meals when we were short-staffed. If you want to start a business because you think it will give you freedom, consider whether you’re actually willing to have less free time.

Are you willing to be responsible for hundreds of other people?

Depending on your goals, you will not only be your own boss but also eventually the leader of a team. This team could be 10 people; it could be hundreds or even thousands. Many of your employees will also represent a connection to a family or household. Add in the numerous other suppliers, partners, investors, and agencies that you might ultimately end up working with, and your business quickly starts to touch far more people than you might have anticipated. This responsibility weighed heavily as we were raising our Series B at the height of COVID-19-driven economic uncertainty. At one point, we were presented with an offer that we felt deeply undervalued our company, but turning it down would mean putting the livelihoods of hundreds of families at risk. After a great deal of deliberation, we walked away because it wasn’t the right path. We were later fortunate enough to receive a better offer, but reaching that point required difficult conversations and decisions. Ask yourself: Do you want to be the one making the kinds of decisions that affect the lives of so many?

Are you ready for the next decade?

We’re into our sixth year at Tovala. Most exits take an average of 10 years, with some taking much longer. Since launching, I’ve gotten married and had my first child. Initially, I kept thinking that things would “get easier” at some future point in time: “when we launch,” “once we close our Series A,” “once we . . .” That has not happened, and that never will be true. My job keeps evolving, but it never gets easier. It will keep changing in the time that we could have another child, move homes, and certainly experience other major life events. Are you ready for the uncertainty and commitment of the long term?

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I encourage anyone interested in starting their own business to think critically about these questions. Take time. Reflect on them. Be deeply honest with yourself. You can be your own boss and follow your passion, but be prepared to take on the responsibility, do the work, and commit to the uncertainty of the future. Then, get ready for the journey ahead—because if you’re willing to accept the risks, there is nothing more rewarding.


David Rabie is cofounder and CEO of Tovala, a smart-oven-paired subscription meal service.