While entrepreneurship is challenging at any point of time in life, the experience can be very different when you gear up for the role at a later age in your life, after you have had worked in multiple companies and at various positions. There is a whole new set of challenges and a very different kind of gratification that a late blooming entrepreneur experiences.
Let me list down a few here:
Finding co-founders can possibly be your biggest challenge
Finding a good co-founder is quite challenging for any entrepreneur, no less than finding himself or herself an understanding better half. One cannot ignore the importance of a good co-founder because good people can fix bad ideas and bad people can kill a great idea! This challenge will become all the more difficult and possibly your biggest challenge if you are over 50, because your peers are well settled in industry in mid to senior levels, having reconciled with the perks and politics that corporate life offers.
While they may carry the risk of getting laid-off anytime, until the time they have a job in hand, they are in their comfort zone and may not really be willing to take a calculated risk and start something new. Getting younger co-founders could be tough too, as typically they will not be in your circle of acquaintance and influence. Moreover, given the huge generation gap, the working styles may clash too, which could lead to issues later.
Rolling up your sleeves and going back to the first “salesman” job
Be ready to swallow your ego, roll-up your sleeves and possibly do things which you have been used to delegating for last 20-25 years. As they say, the founder of the start-up is its best sales person in the beginning years. This means that you will have to get down to the “travelling sales person” level, atleast in the beginning, to secure your first few customers. This can be tough and will demand you to seek help from others, which you may not be very happy doing.
Getting plugged into new “business dynamics”
The way of doing business changes every 20 years or so, and these cycles are becoming even shorter in today’s connected world. As the world becomes hypercompetitive in every vertical, what could be done by a “handshake” in the 90s, can’t be done even with the best legal contracts now. So you may find yourself at odds when dealing with customers, employees, contractors and other folks. While you may value a commitment made for doing a call at a particular time, people around may simply choose to forget and be totally unapologetic about it! If this makes you angry and you end up burning bridges, be assured that your start-up journey will meet a premature death. You will, therefore, need to be very adaptable and just sail along.