An Optimism Tempered by Fear

The hallmark of the entrepreneur is usually unqualified optimism. “We will disrupt this space” is a common refrain. You expect to hear that every idea is a “billion dollar opportunity.”

But lately, in several private conversations, I’ve been hearing from entrepreneurs who speak in a much humbler tone. They ask me, “Am I too old to start a business?” One guy said: “I can get over the fact that every venture-backed startup seems to be led by a CEO right out of school. I can even get over the fact that there’s probably some age discrimination at play when it comes to financing startups. I think I can afford to launch a company. But I’m not sure I can afford to fail. Am I too old for a startup?”

It’s easy to tell someone that you’re never too old to start over. Or you’re never too old to start up. Or you’re never too old to dream of doing something big. But is it true? At what point does the fear of failure become a self-fulfilling prophecy for those embarking on the path of entrepreneurship?

Older people arguably have more to worry about than younger people. Older people are more likely to have families or they may be gearing up to start them. Older people may be taking care of aging parents or considering how their own retirement is approaching. An older person’s desire for stability may trump their search for new experiences as they consider their finances, obligations, and time required to start anew if their venture were to fail. So an older person may have a great business idea and huge ambition, but if their savings aren’t very large, it’s understandable they would be afraid of the possibility that they might find themselves looking for work and depleted of savings with nothing to show for their failed startup.

If that outcome sounds bad, it’s not the worst prospect. It’s a fact that most businesses don’t succeed, but they often don’t fail right away either. Instead, they may churn along for 5 or 6 years before they finally fade away. Worse than being 45 with no salary or savings is being 50 with no salary or savings.

“Can I really afford to take that risk?” they ask me. To put it simply, there is no easy answer.

Is Entrepreneurship Less Risky than the Alternatives?

There exists the notion of launching a startup not as fulfilling a dream, but as pursuing an alternative. For example, most people considering starting businesses are unhappy with their current situations. In New York, I’ve met many people who have recently left high paying jobs in finance and are now considering becoming entrepreneurs. They evaluate the tiny salary they might earn with a startup against the much larger salary they were earning at a bank, struggling with the huge differential. But, the comparison is often a false choice.

When the banks downsized a few years ago, they laid off many people in their 30’s and 40’s. And the unfortunate truth for many of these people is that as the banks begin rehiring, they’re replacing their mid-level managers with upstarts in their 20’s. The same is true for other professions where older, more expensive workers are replaced with younger, cheaper workers. For any person who once believed that their career was a lifelong decision, they may now be a third to half-way through their life, faced with the reality that they must learn new skills necessary to transition their careers to an increasingly digital world.

A Startup as a Tool for Developing New Skills & a New Rolodex

Sometimes, the ability to recognize how bad the alternatives are makes starting a new business easier. When you realize that the old opportunities no longer exist or that you’re missing the skills to get the new jobs you want, or worse yet, you’re just miserable with the established way of doing things, the prospect of launching a startup is less about seeking new possibilities and more about fulfilling an imperative.

When you’re older, you’ll need to consider different issues than you would if you were younger while embarking on a startup. You should be aware of the resources you’re lacking as well as the skills and expertise that you’ll need to scale. For example: if you were to launch a social networking app, you would need to develop an understanding of product design and development, and you’d also need to learn what it means to construct a funnel for acquiring customers and how online paid acquisition works. It’s crucial that recognize your weak points and plan ahead.

Recently, I spoke with a 40-something entrepreneur who was evaluating the future of his enterprise software business that he’d been selling to some of the largest retailers in the world. He wanted to know what I thought about his prospects if he were to discontinue the business. I pointed out to him that his rolodex of senior executives at these retailers was second to none. He had perfected the sales process akin to something of an artform.

If his startup didn’t succeed, it wouldn’t be because he couldn’t sell, but because there were macro changes afoot concerning the software being used in his industry. He could feel safe pursuing his business, knowing that every day he was learning and building more for himself, regardless of whether or not his business succeeded. If he ever needed to find another job, the relationships and skills he’d been developing would prove invaluable for another software firm targeting these same clients.

I find that every entrepreneur is afraid of failure. But the sine qua non for the successful entrepreneur is to operate in a way where the fear of failure doesn’t cripple your ambition or cloud your strategic decision-making skills. The culture of entrepreneurship is predicated on the notion that failure is expected on the path to success, so much so that entrepreneurs who have failed are generally viewed as more financeable than aspiring entrepreneurs who have never tried to start businesses.

As an older first-time entrepreneur, you’ll need to convince yourself prior to starting that failure is likely. If it happens, it will be part of your journey, rather than the end of the road.

Mitigate Risks by Choosing the Right Business & Planning Ahead

More responsibilities means that older entrepreneurs need to be much more granular in planning than younger entrepreneurs. This is especially true when managing the personal cash flow. Whereas you once might have been comfortable with unknowns and living off of credit card debt, you’ll now need to understand the exact cash requirements of your new venture before you start.

I tell people who are starting businesses that they should plan to go 6 to 9 months with no salary. At the end of that period, if you’re able to raise capital from friends and family, your annual salary probably won’t be more than 10% of the total money raised– a number that is likely to be less than what you’d be earning at a day job. Your strategy for dealing with the salary issue is to develop a clear understanding of what you will realistically make and how much of your savings you’ll likely deplete before you can expect to earn a more competitive salary. Whereas younger entrepreneurs might not contemplate devising a personal “breakpoint,” you’ll need to figure out early on at what point you won’t be able to afford to continue your business.

If the “breakpoint” is a year out and you’ve selected a business where you’re acquiring skills that would also be useful on the hunt for a new job, then you should be able to come to terms with the prospect of failure. Recognize that a new venture will shape you and your trajectory regardless of its ultimate outcome.

The Takeaway:

  • It’s normal to have fears, but don’t let them cloud your judgment.
  • Analyze your situation objectively to figure out whether or not a startup would provide you with more long-term opportunities than your current career path.
  • If you decide to launch a startup, create a realistic personal cash flow and choose a “breakpoint” before you start.

– Andrew

Read part II here.

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