The Best Days in a Founder/CEO’s Professional Life

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There are a ton of great days that come along with both founding a business and leading a business.  While the lows might be really low, there is no greater professional joy that creating and building something substantial.  Here are some of the best days:

• The “Firsts:” The “firsts” are awesome. The day you make your first hire is a day of affirmation.  Someone thought your idea was good enough to put their career in your hands. The day you ship your first product, you feel an immense sense of pride for seeing your team deliver on v1.0 of your vision. Your first “user” or “customer” shows you that at least one person believed that you built something of value. The day an investor closes on your first round of external funding validates that people will not only put their career in your hands, but their money, too.  Everything about celebrations at a startup seems to be about “firsts.” So much about what we try to do at startups is create the future; and what better way to celebrate the imminent arrival of the future than to celebrate the “firsts” that help get you there.

As you go through your journey, you start to realize that “firsts” are really important but they are a bit like puppy love. They seem like the most important events in your life, and yet – the consequential milestones are the ones that are yet to come.

• The day someone you bet on grows up: So much about innovation is about betting on people. At BloomReach we’ve made plenty of bets. We bet on a whole new blended analytical product and account management role and when the first member of that team became a manager, it was a terrific day. I’ve made bets on key execs, folks who have not had the scale of roles they today have at BloomReach.  And the day when they stand up in front of your board and your board member passes you a note saying “you’ve built a great team” is a terrific feeling.

• The day that someone else sells your product: As a founder, you’ve likely moved heaven and earth to help accomplish your first sales. You’ve been half product manager, half salesperson. You do that in the beginning to drive momentum but you have this gnawing fear that no one else will be able to sell your product. And then someone steps up to do it. It makes you feel like a million bucks because it means you can begin the arduous process of thinking about scaling.

• The day you can actually predict your business effectively: Startups are about small numbers for a long time. Small numbers of users or customers or employees or early revenues. Big companies are about sizable revenues and margins and predictability. As you go through your financial planning it can feel pretty ad hoc for a long time. In fact, it can feel like a waste of time because you are nowhere near any kind of scale. And then the day comes where you put together a financial plan to forecast the business over 6 months or a year and actually hit it or exceed it. That’s a terrific day. It means you have real metrics to help you drive your business and that means that you have levers to pull to help you achieve your next milestones.

• The days when you give yourself the guilty pleasure of retrospection: It usually comes on anniversaries (5th anniversary) or material financial events ($1 million per month of revenue). On those occasions it hits you – we started with two people in a small office. We have created a real business here, with really valuable employees, great products, great customers and a great future. The “look at where we came from” days are important. They give you perspective as you confront the many challenges you face.

• The day someone tells you they are building “The [INSERT YOUR COMPANY NAME] of [INSERT INDUSTRY]. That is a pretty crazy day. When I started hearing other entrepreneurs talk about themselves building the “BloomReach of Social Networks,” or the “BloomReach of B2B Marketing” – I knew we had done something pretty special. Of course you have to have good marketing along with a good business to deserve it. There is a certain “I have arrived” feeling about the day you hear that.

You start companies mostly for the good days. The highs are so high that they can keep you going for a long time. They feel like that perfect golf shot – the one that makes you think somewhere deep within, that you might be working with more than a good wind at your back and a little bit of luck.

Image from Happy Flyer by Paul Hocksenar licensed under CC by 2.0

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