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4 Questions That Entrepreneurs Must Ask Themselves

By Fast Company
Financial Services

Every entrepreneur knows that as soon as you’ve cleared a hurdle and are celebrating a success, a new challenge arises. My good friend and Okta CFO Bill Losch sounds like a broken record every January when he tells me: “Freddy, now this is going to be our most important year yet.”

He’s right, and he reinforces a message I’ve shared with entrepreneurs over the years: No matter the stage of your company, it’s always about what comes next. The roller-coaster of entrepreneurship begins with what we call the “a-ha moment”–when the light bulb comes on, there’s a clear market need for the product you’ve just dreamt up, and you envision multiple paths that lead to success. But no matter how the journey unfolds, the moments before, during, and after the ideation stage are never quite what you expect.

This week on Zero to IPO, Epic magazine’s Joshua Davis and I spoke with four entrepreneurs about what comes after the epiphany. Namely, the process (or lack thereof) around turning an idea into a reality, roadblocks that feel like Mt. Everest, and key learnings. We asked a few common questions entrepreneurs face during this phase and shared stories on the highs and lows of bringing an idea to life.

1. “How can I make my idea even better?”

As an undergraduate engineering student at Stanford, entrepreneur and Jawbone founder Alex Asseily had a grand vision for wearable technology. Inspired by the mobile revolution, he envisioned an entire ecosystem of wearable communication tools. But over the next few months, he watched his idea whittle down from a full suite of products to just a headset, to eventually just the technology within the headset. Sure, the end product looked completely different from his initial vision, but staying open to change enabled him to establish legitimacy and close his first $1 million round of funding.

If you think you’ve dreamt up the “perfect” product on your first go, think again. Embarking on the entrepreneurial journey means accepting your brilliant idea will go through iterations. Ideas take on many forms before crystallizing into one that captures investors’ interest and customers’ demand, and it has to be durable if you want it to succeed in the long term.

2. “How long does this take?”

Entrepreneurs tend to be optimists: We have grand ideas and want to make them happen as soon as possible. Most of us imagine things running smoothly and efficiently, with everything falling into place. And due to our passionate nature, we also often (and sometimes, drastically) underestimate when it comes to how long it takes to bring initial ideas to life.

According to Canva CEO Melanie Perkins, bringing a product to market often takes far longer than you expect. At the beginning of her journey, Perkins predicted that she’d design and build the entire publishing feature for Canva in the first 12 months. In reality, the process took much longer. Most companies, and especially enterprise tech companies, don’t find success overnight–so it’s helpful for entrepreneurs to recognize that they’re embarking on a marathon rather than a sprint, and prepare for unexpected circumstances to come up along the way.

3. “Is now the right time?”

The success of an idea doesn’t just correlate to how brilliant it is–it also depends on experience, timing, and what’s going on in the market you want to enter. Fred Luddy started ServiceNow, a now multibillion-dollar enterprise software company, when he was 50. Because of his experience as a CTO, developer, and entrepreneur, he had in-depth knowledge of the ins and outs of the enterprise marketplace as well as the customer needs, existing solutions, and competitive offerings.

As you’ll hear from Luddy’s story, while younger entrepreneurs often benefit from being close to the technology when starting consumer companies, those who want to launch enterprise businesses have the advantage of experience. In this market, more experience generally equates to a deeper understanding of the opportunities, risks, and the path to success.

4. “Ideas aside . . . do I trust this team?”

Sometimes, it’s not even about the idea at all: It’s about the people behind it. When Marc Benioff presented the concept of Salesforce.com to cofounder Parker Harris, Harris didn’t worry too much about the idea itself. His instinct told him that if it didn’t work out, Benioff and his team would find new opportunities on the road ahead.

Harris’s story shows us a great idea can hinge on the team or the person selling it to you. Rather than buying into a specific product or company, considering the team that will support it–and pivot with it as needed–is often just as important. You can’t build a business based on a great idea alone. You need to have others who are supportive of your vision, and are excited about executing it with you.


Frederic Kerrest is the COO and cofounder of Okta. You can listen to the full episode, “You’re a Genius,” wherever you get your podcasts. Tune into Zero to IPO every Tuesday and check back here each week to read more about the insights on each episode.

Photo: Getty iStock

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