WHAT YOU FEEL: it’s awesome to get wins, but they always seems to unearth other issues about my company

PERSPECTIVE: Every day in the life of the entrepreneur is like a round of a boxing match. When a boxer wins a fight, he got the better of the action, but it still means that he got hit in the face for three hours. While it is not only based on punches, if we oversimplified the scoring, this means if you win a round, you hit the opponent one hundred times and got hit ninety times. Win or lose, you get hit in face at least ninety times.

Almost every activity comes with both pleasure and pain. When you don’t have the resources or the capital you need, there are often more losses than wins. When you do get wins, they are energizing, but they always seem to raise other issues. I remember when we won our first big customer:

We were high fiving in the parking lot. We had been awarded the health incentive business of a large national health plan and just signed the contract at their offices. It was a two year process and winning a national health plan would likely ripple throughout the health community. The ride from Connecticut down Route 95 back to New York City is packed with traffic. Who cared at this point. The team was on cloud nine. Then it hit me. Did we have the resources to support them? What if this one health plan went poorly? Were the account people we had sophisticated enough to manage a complex health plan? Would we end up customizing our technology and throwing our technology roadmap off course?

Celebrate your wins. There are many times during the meeting, the hour, the day, the week, and the month that you will get kicked between the legs. At early stages, wins tends to be small and incremental. Nonetheless, celebrate them. At the same time, be prepared that when the wins come, they naturally raise issues and concerns. It’s like when you have reached the stage when your teenage daughter matures and is no longer a bratty little girl, she is also going to date.

Every day you work to make progress and get wins. When your organization still doesn’t have its foundation, these wins expose the shortcomings of your organization in terms of capital, resources, technology, operations and people. For example:

• You close your first big investment. Employees want more  salary. Vendors want more commitments. You need to manage your board and investors. Is your CFO experienced in talking to investors and creating the financial reporting they need?

• You hire your first big management team member. Current employees feel slighted. You pay more attention to someone who has been with the business two weeks than you do to the people that have toiled with the business since the start.

• You finally have employees that are helping advance the business. You now have a payroll, greater risk and a financial nut you must cover each month.

• You win your first big customer. Who is going to handle the day to day relationship? How are we going to manage a company of 50,000 employees when we have ten?

• You release your first version of your software. Your competitors now see it. Your customers are banging on it.

• You sign your first office lease. Gone are the days of working in your “workspace.” Whew! Who’s paying for all this?

• You get your first big order. Your customer wants twenty of your jewelry design? How are you going to buy all the materials for the jewelry?

Pleasure and pain. We work every day to make progress. When we make progress, we expose weaknesses. The questions that come with the evolution of a business are natural. The immaturity of your business get exposed. While the business challenges that arise can be difficult, the greater challenge is what this dynamic does to your psyche and the psyche of your organization if we don’t handle it properly.

If your organization is fortunate enough to be making progress, your business gets more complex and more challenges arise. We win that customer. We launch a product. We close an investment. We bring on a team member. We get good PR. The daily grind with all the pressures and risk that come with being an entrepreneur all seem worth it when you get those wins.

Be thankful for that. It means you are succeeding. However, this exposes deficiencies and often ones that are personal. For the business, it exposes the risk of capacity, team members, the reliability of technology and the risks goes on. For us, it often exposes our deficiencies. We may have been perfectly well-equipped to manage a few people in startup mode, but do we have the skills to manage and lead a larger company?

This is particularly true when it comes to investors. Securing an investment should be a day of celebration. It is a validation. Whether it is $10,00 from a family friend or $10 million from a private equity firm, it represents progress. At the same time, investors present challenges. If you secure an investment, do you have the experience and resources to manage a Board and investors?

With wins and successes come concerns and doubts. Imagine someone who won a $50 million lottery saying “sure but I must pay twenty million in taxes.” As an old law school professor used to say “taxable income is better than no income.” Some say “be careful what you wish for.” Don’t every forget how lucky we are to be making progress.

Our perspective on this is critical. Even though there is pleasure and pain at almost every turn, we must move the organization onward and upward. We must celebrate wins. We must appreciate that you are being challenged because you are fortunate enough to be growing. Investors, customers and employees are attentive to our venture because we are bringing something that is valuable to them. Don’t forget that. Make sure you and your team always understand that the alternative is sitting in your bedroom and writing business plans that no one cares about.

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