The Founder’s Paradox: How to Start a Company When the Time Never Seems Right

founder's paradox: start a business

“What is holding you back?” That is the question I asked a job candidate who shared that they wanted to eventually start their own company. Their response was that “the timing is not right.” This is an understandable answer — one I have heard a lot from aspiring founders. I understand. But I often disagree.

Consider the following fact: There is never a right time to start a company — there is only a must time.

Let me explain. This “must time” comes when starting and running your own business is the only thing you can imagine doing. It is not unlike other major milestones in life — getting married, going back to school, or thoughtfully deciding whether or not to become a parent. There is no right time, just the must time.

And just like those other major life events, you need to be ready to make your must time the right time for building a business. It takes self-awareness and a willingness to be vulnerable. You need to make the necessary changes to your mindset and actions from the start to set yourself up for success.

This is something my Aha! co-founder Dr. Chris Waters and I knew before we started the company. We had been working in Silicon Valley for nearly 20 years and we knew we wanted to build something different. We were realistic about the sacrifices that would need to be made.

And here is the thing — deciding to launch Aha! was obvious. Because truly, we needed to do it. We needed to build something different because we knew there was a better way than how technology companies were predominantly being built in Silicon Valley. Our strong belief was (and still is) that it is possible to create a product and company people love.

It also had everything to do with the deep understanding that life does not grant you too many performances. Time is not something you can beg for or buy more of. I feel fortunate and cursed to have come to that conclusion. Fortunate because it motivates me every day and cursed because the realization was accelerated by my sister-in-law’s illness that ultimately took her life.

I came to the stinging conclusion that not launching Aha! would be more frightening than the risks we would face. Despite being a VP at a well-known public company, I knew I needed to get busy building something new.

Procrastination comes in many forms. When it comes to founding a company, there is often a mental game of fill-in-the-blank that aspiring entrepreneurs play. It goes like this: “I will start a company when ____.” You can probably add your own answer. “When my kids are older.” “When I pay off my mortgage.” Or the classic, “When life settles down.”

So, how can you overcome the “when _____ happens” challenge and start one of life’s great adventures with calm confidence? Start with your first business purchase — a notebook. Divide it into five sections, titled as follows: Thoughts, Feedback, Purpose, Money, and Sacrifice. Then, to hold yourself accountable, choose a month when you will devote yourself to deep introspection.

Track thoughts
Pick one week. Then write down the times and days when you think about your idea. As you log each entry in your notebook, ask yourself why. Where are there patterns in times or days? What is motivating you? What are you reacting to? Passion is not good if it is only a distraction from something else that is bad.

Get feedback
Too many people think ideas need isolation. Stealth is stupid. Describe your idea to people you trust and use the experience to learn. Can you articulate the problem you are solving easily and is your language clear? Do people get excited or nervous when they hear your thoughts? Capture the answers — a strong reaction (positive or negative) is a sign you are onto something big. (And you might just find people who are as passionate as you are to work with.)

Map purpose
Lasting and meaningful companies are built on purpose. So, look at your thought-tracking and feedback lists and ask yourself if your underlying motivations are tied to your core path in life. Map the motivations to your purpose and assess where things do not line up. Are people enthusiastic that you are on the right track? You need to know exactly why you want to start a company. And the closer the purpose is to who you are and what you want to become, the better chance you have for success.

Acknowledge money
You must build something that real people with real needs will find value in and pay for — otherwise you do not have a lasting business. So, force yourself to document why customers will pay you. Then, estimate how much. Start there and create a simple one-page business model to explore the real mechanics of the business and how you expect it to be successful.   

Pre-experience sacrifice
You will need to sacrifice from the start if you decide to pursue your idea. Feel the pain before you accept the suffering. Pick another week to write down all the ways you will need to sacrifice while building your company. Go for detail and list out what you will give up for at least two years.

Not many people are ready or willing to do this kind of deep thinking and introspection.

Too many people start businesses for the wrong reasons and fail themselves and those around them. Big action takes big courage. After all, founding a business will define you. So, are you ready for the adventure?

There is never a perfect time to launch a company but there definitely is a “must time.”

Are you ready?

Read more of The Founder’s Paradox.

About Brian and Aha!

Brian seeks business and wilderness adventure. He is the co-founder and CEO of Aha! — the world’s #1 product roadmap software — and the author of Lovability. His two previous startups were acquired by well-known public companies. Brian writes and speaks about product and company growth and the adventure of living a meaningful life.

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