The Nine Invaluable Lessons I Learned During My First Year as an Entrepreneur

A little more than a year ago while we were still in school, my cofounder Ramli and I began working on our startup, FamilyTales.

It was his fourth time around the circuit and my first. While I had always been interested in working with entrepreneurs and small businesses because of the excitement of seeing awesome things being built out of nothing, I didn’t think I’d start my own venture then. In this post, I’d like to share some of my most important lessons with you.



FamilyTales has been a fully self-funded operation. When we set out to start working on it full-time we were fresh graduates, with a significant amount of student debt. But there’s nothing that can teach you a lesson or two like the cold and unambiguous way money can.

If you’re going to be quitting your day job, make sure that you will be generating revenue out the door. This could either be in the form of actual cash from customers, credit card numbers from subscribers, crowdfunded campaigns from the likes of Kickstarter, or at the very least letters of intent. If I were to go back, I think I would have taken on a day job. This usually makes startup founders cringe. It almost sounds like selling out. But the sense of peace you can get from having a regular stream of income can be liberating for your creativity and efforts to get your startup off the ground in the evenings.

And once you’ve brought your startup to a self-sustaining level, you can then feel free to take the plunge and go in with everything you’ve got. This will spare your or your loved ones’ sanity.



Everyone loves painkillers because they take away pain. But while vitamins, like gym memberships, are great things to have in theory, they are difficult to get people to repeatedly use.

If you’re looking for a relatively safer way to get business success, then make sure you are taking someone’s pain away. Chances are that if you find someone with a bleeding neck wound and you offered them a tourniquet for it, they will grab it from you, no questions asked.



At one point, we listed out a half dozen of FamilyTales’ most engaged customers—they became our stars. We focused more of our attention on their needs and feedback.

But as we started getting newer customers, we lost sight of keeping our previous stars happy. Pretty soon we started getting pulled left and right, and asked a lot of “what if” questions. The end result? We built something that nobody found fully delightful.

Pick your handful of star customers and make every effort to make them happy. Chances are you will then be able to transfer this winning formula to others.



It’s likely by now you’ve heard about Csikszentmihalyi’s notion of “flow”: a state of immersed concentration that leads to great bouts of productivity. When you’re in a small startup team, however, it becomes incredibly important (and challenging) to be in a state of “team flow.”

I think of Team Flow as not just each individual member of the team being in a flow in isolation, but rather the members being constantly in tune with each other and feeding off each other’s energy. If everyone is in the zone, the sense of urgency, momentum and hunger to succeed is unmistakable and incredibly contagious. This in turn can lead to great productivity, a sense of accomplishment, and a sense of togetherness that is needed to get past the hardships of a startup’s infancy.



When you sense someone is drifting away from this tight loop of a Team Flow, do everything in your power to reel them back in. And this usually involves you being someone whom you’re not that comfortable to be. For example, if a particularly gregarious member of your team suddenly becomes distant and quiet, you will likely have to step in and probe a little, possibly injecting some cheer and energy back into the empty space the person has left. If you are not used to this, it can be difficult. But it is crucial.

When you’re not in a Team Flow, you are unproductive. And when you’re unproductive you open the doors to Bad Things. Like loss of momentum, self-doubt, alienation, and fear. This is a toxic brew for a startup.



You never know when someone will come to your aid or delight in the future. Don’t be selfish and manipulative about your relationships. And definitely never enter a relationship expecting that you are entitled to the other party’s time or efforts. Your industry contacts, fellow entrepreneur friends, mentors, advisors, and trade show acquaintances are all capable of pleasantly surprising you down the road. Conduct your affairs openly and respectfully, and try to provide them value in return.

As Porter Gales says, your net worth is dictated by the strength of your network.


7. Don’t be afraid to reach out for help

It doesn’t make you weaker to do so. The startup ecosystem can be wonderfully sympathetic and helpful as long as you are graceful and respectful of people’s time and energy.

Sometimes asking for help in one area can lead to incredible payoffs in other things that you weren’t expecting.



I will be honest here and admit that for a very long time I figured myself to be the entrepreneur’s biggest fan, but never the entrepreneur. I told myself I was too risk-averse, mellow and introverted to be a hustler. And that since I never had an entrepreneurial project growing up, that I didn’t have the chops for it.

But I know now that being risk-averse, mellow, introverted, or a thinker as opposed to an executor all have their place in entrepreneurship. For every product launch there must be an analysis and for every win/loss there must be introspection.

The debate over whether entrepreneurs are born or made may rage on, but in the end, it’s not what others have said of you that will dictate your future. It will be the collective of your own decisions, actions, and capabilities.



There is a great tendency among young entrepreneurs to emulate other successful entrepreneurs in the hopes of repeating the latter’s successes. This is OK, to an extent, as I do think that there is a lot one can learn from others with more experience, of course.

But much of what makes a product or service delightful belongs to you and your unique perspective, not others’. Entrepreneurship, when done with gusto, can be as much a form of self-expression as any other work of art. Don’t rob yourself of that opportunity to shine. There should come a time when you kill your heroes and start marching to the beat of your own proverbial drum.

And bang it till a parade forms behind you.

I hope these lessons from my year help you—even a little—with your own ventures.