Journey of a Serial Entrepreneur

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How to get from where you are to where you want to be

Crossing the Rubicon

The Rubicon, is a river in northern Italy which Julius Caeser crossed in 49BC from which point it was not possible to go back. Crossing the Rubicon hence refers to passing through that point from where return is no longer possible. This may be due to a host of factors, such as, it being physically impossible to turn back, too expensive to go back or that the path is too dangerous. Working with startup companies I find it a most exciting part of the journey when that point of no return is crossed . However, please make sure that before crossing your Rubicon you are doing so for the right reasons.

When I setup this blog on the 1st of January 08 I crossed a point of no return. I let all my readers know that I was going to spend the next year updating this blog on a daily basis with advice and insights on entrepreneurship and life. I did so because I felt that I had a little experience which could help others who are in the process of setting up a company or working at a startup for the first time. From that day onward I had a responsibility to everyone who was reading this blog to make sure that at the end of every week I gave some advice which could be potentially helpful. It doesn’t make a difference if I have one reader or a million, my responsibility remains the same. Eleven weeks later writing my blog has become one of the most fulfilling part of my week.

If you are on the verge of starting your own business, deciding on a certain career path or even getting married, the one thing which you keep in mind before making these big decisions is “do it for the right reasons”. You shouldn’t let anyone force you into such decisions Look at them from all perspectives, align them with your value and belief systems and when you make up your mind ,cross your Rubicon without a whisper of a doubt.

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Motivational Environments

“Our environment, the world in which we live and work, is a mirror of our attitudes and expectations.”     Earl Nightangale

Going to work everyday should be far from a chore, it should be the reason for you to jump out of bed in the morning. (Flash back) Seven years ago I finished high school and like quite a few of my classmates at that time, investment banking was on everyones mind. So when everyone was applying to B school programs I decided that I would take some time off before university and get a glimpse into what investment banking would be like. I interned at one of the larger investment banking firms and it didn’t take me very long to figure out that we were not a very good fit. Thats when I changed my majors and decided I needed to find something else. I am in no way downplaying careers in finance, its just that each one of us are unique and are motivated by different factors and environments, finding one that suits your personality is essential.

As startups grow larger we have to make sure we maintain similar environments that sparked the creativity in the first place. Two companies come to mind which have done a great job of keeping the balance in check, they are, Google and IDEO. Both highly creative companies which focus on the environment for their most important asset…their people. Creating and focusing on an environment which fosters creativity and inspires, enables people to think out of the box without fear and builds loyalty. It becomes easier to work as a team when you can communicate and help each other reach his/her goals. There is nothing worse in my opinion than having a ton of ideas on how to improve a service or product and not being given a platform to express them.

I am an advocate of keeping communication among the teams I work with as candid as possible. Knowing each others goals and roles enables us to do whatever it takes to help our group mates to succeed in reaching their targets. Make the motivational environment of your organization a key metric to be constantly measured. What is the morale level of your team?

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Progress motivates

“Don’t wait untill everything is just right. It will never be perfect. There will always be challenges, obstacles and less than perfect conditions. So what. Get started now. With each step you take, you will grow stronger and stronger, more and more skilled, more and more self confident and more and more successful.” Mark Victor Hansen 

Momentum is the force which everyone and every company is aiming to achieve. In my short span in the entrepreneurial space ,I have come to realise how strong a force it can be. It has the ability to inspire, excite and motivate. You discover your capabilities on a completely different level and at times surprise yourself as to what you can achieve. Without it you are like a ship set to sail with no wind to help it along the way. 

When starting any new venture, if there is one thing which should be aimed for, it is to get some momentum going. This can be any activity where visible and tangible results are being created. Initially it could be as simple as getting your business plan together. Later it could be closing that first deal or getting some marketing publicity. As you begin to see and be part of the progress it will give you, the motivation to push yourself further and harder emerges. You will have this surround energy which will attract others to help you along the way.

If you or your team is lacking motivation take a look at their spirit and morale. If it is not at its optimal see how you can generate some momentum into your current business model. If the approach you are taking isn’t working, brain storm other ways to approach it. You have to focus on building momentum as quickly as you can and most importantly making sure you maintain it once things have been set into motion. 

Few things in the entrepreneurial world compare to when you have momentum on your side and things are working out better than expected. How can you add momentum into your venture today?

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Challenging goals

“If you’re bored with life — you don’t get up every morning with a burning desire to do things — you don’t have enough goals.” Lou Holtz

Checking your goals list is a very valid reference point when you or your team is not performing at its optimal. You may have set goals and steps for it, yet, not getting anywhere. This situation often arises when your goals or your teams are not ambitious enough. Knowing you have the capability of doing a $100k in sales in a quarter and setting yourself a target of $50k is not doing justice to your abilities. You have to balance your goal setting carefully using the SMART system which is an extremely effective one. 

 A lot of entrepreneurs become complacent very quickly when their startups pick up. In the dynamic and highly connected world we live in, no one can afford to become complacent. This applies across the board whether you are an entrepreneur, in a career or stay-home mother/father. Everyone needs to feel the urge to do more to remain connected to the world. It is when we break the connection that the trouble starts. 

In summary, evaluate goals on a regular basis and be thorough in this exercise. Bring balance to them using the smart goal setting system. If you do not have enough challenges at work talk to your team mates or your boss about the situation and work on ways to improve your product or service. Whatever you do, just don’t stand still because thats just about the worse thing you could do for yourself. Take up the challenge to do more today!

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Everything starts with you

“People are always blaming their circumstances for what they are. I don’t believe in circumstances. The people who get on in this world are the people who get up and look for circumstances they want, and, if they can’t find them, make them.” George Bernard Shaw 

We all have days where nothing seems to be working out right. How we react to them is what makes all the difference. Do you tend to take your frustration out on other people, keep to yourself and avoid any sort of contact with others or do you take whatever comes in your stride and figure out how to get things back on track. You need to keep your motivational level in check all the time and it becomes even more important when you are leading a group.

At a startup company things do not always go as planned. You will have days where your level of commitment will be tested. When I am having one of these days I take some time out and bring focus to what it is that I am wanting to achieve. I have a goals list which I refer to which outlines all my goals and steps to get to them. I then compare it with the direction we are taking as a company and whether we are in sync with what we all set out to do. If they have been any changes I evaluate where they were made and how it has affected our progress. I then consult with the team and ask for feedback from them  as well.

This whole process ends up providing me with the focus that is required to move forward with our plans confidently. Being able to share my thoughts and opinions re-affirms certain thought processes and fuses that energy which goes missing when things are not moving in the right direction. So next time you are feeling a little low and things are not moving along as smoothly as you would have hoped for, take a step back and take a look at the bigger picture. Remember as a member or leader of a team it is your responsibility to bring your A game to work everyday.

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Are you or your team lacking motivation?

“Most people give up just when they’re about to achieve success. They quit on the one yard line. They give up at the last minute of the game, one foot away from a winning touchdown.” – Ross Perot 

Motivation is an essential characteristic for an entrepreneur. Some people call it the “fire within” while others think of it as “jolts of adrenaline”. It is that feeling that gets you up ridiculously early in the morning with the feeling that today is going to be a great day. Sometimes it is the only thing that you have going your way when things are not coming together as planned. It is however natural that you will have some days when your energy levels are not where they usually are or a lack of progress has demoralized a teams drive. You need to take action to reverse this process as early as possible. I have witnessed first hand how lack of motivation begins to eat away at a person or team and completely changes them. You do not want to go down that lane. 

Everyone approaches the topic of motivation from a different angle. This is because each one of us is motivated by different factors. That is what makes this topic such an interesting one. I am going to take this week to talk about what I do to motivate myself and my team. I would really appreciate it if along the way everyone could pitch in with how they are motivating themselves or their teams. This will help us to get a diverse group of factors.

In the end all that matters is that you know what motivates you. What makes you tick? Identify these factors and keep close track of them. They will be the key to get you through those hard times and will propel you even higher during the good times.


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