It Matters Who You Do It With

They say you never forget your first time. I won't forget mine. I was a junior in high school. And even then, I knew that it deeply mattered who you did it with.

I'm not sure when most people do it for the first time. I'm sure there are tons of studies. But for me, I knew the time was right, and so did my partner. In fact, the idea had been there for some time, so it was almost like we couldn't not do it.

I’ve heard that some people never do it. Maybe they can't find the right person. Of course, this further cements my theory that it matters who you do it with.

And before we go any further, I should clarify. I'm not talking about sex. I'm talking about starting something.

Junior year, Jacob and I had an idea. We had a group of friends who all either went to church or school together. We wanted an authentic expression of our young faith – something that went beyond regularly scheduled church activities. We wanted something that created a venue for us – and people like us (kids our ages) – to ask deep questions, comment on our personal spiritual journeys, and enjoy the outdoors.

So, we came up with an idea to get a group of folks together to meet at a picnic shelter in the park on Saturday nights during the school year. We'd grill out on a Coleman camping grill, some people would bring burgers, some were in charge of condiments or drinks, and others simply brought some friends and themselves. We'd have a theme for discussion, sing some songs and dismiss quietly and obediently into the night.

To get it off the ground, I remember Jacob and I being so excited to start something – something that was real and needed. Something that other people wanted to be a part of. Something that had the potential to continue indefinitely.

And so, to get it launched, we talked it up. Jacob and I spread the word. I wrote letters to adults I knew and we actually raised $300 to get some of the necessary supplies to get it started. And while it was exciting, fun and important to us, through the experience, I first learned that it matters who you do it with.

For us, our Saturday night gatherings were easygoing. They were never really stressful. Above all, they were fun. Sure, there would be deadlines and a bit of pressure in coming up with the week's theme, or having to run to the grocery store at the last minute to get something we forgot, or that time I had to go back to the park close to midnight because I forgot Jacob's handmade stool at Pavilion #12. But in all that minimal amount of stress, Jacob and I were able to work together, support and encourage each other, and make sure that we kept doing what we were doing. Indeed, still to this day, I credit Jacob with being the one who has helped make me the speaker I am today. We had the kind of relationship that saw us through the organizational requirements of starting something; and we had the kind of friendship that made us better people, because what we started wouldn't be all we ever did as people.

Had I tried a similar initiative with someone else, we might have had the same results (attendance, income raised, success stories), but there could have been more stress. It might not have been as meaningful for me personally. I could have been turned off from starting anything ever again.

Fast forward nearly ten years later. After searching for nearly three years for a church to call our own in Nashville, my wife and I decided to create the community we sought. It was hard at first. After we announced that we were starting a faith community and invited people, we sometimes sat alone in our house. Sometimes only a few people came. And now, over two full years into it, we've got a group of about 12 people, who meet each week to encourage one another, speak honestly about faith and dream together about the good that can be done in the world, starting with a dozen people who dare to meet with one another for that very purpose each week.

Again, if Lynnette weren't the person to take this journey with me, I might have closed the thing down a while ago. If the person I love more than anyone else weren't the one with whom I traveled on this journey of leadership and outreach, well then, it might not even be worth it. And if our friend Mark didn't join in with us, who knows where we'd be?

And, what seems to be the epoch of my entrepreneurial life thus far, CoolPeopleCare would not be what it is today without Stephen Moseley. We wouldn't continue to operate and grow without Malinda Moseley or Michelle Andrade. For us, the team helps shape the direction of the organization. It's that important.

When things get tough, when money gets thin, when questions get asked, when horizons get bleak, when sleep gets missed, when travel gets long, when rejections get sent – what keeps us going is often each other.

In reading and learning more and more about venture capital and the world of investing, you'll quickly see that many individuals and institutions often invest in good teams. And this often means people with great track records, years of experience, and many lines and highlights in their resumes. And while that's all well and good, I don't think I'd trade CoolPeopleCare's lack of experience for a mountain of experience that could be found in some people who aren't able or willing to get in the trenches with you and sit and sulk when that time comes.

What works for Stephen and I – and what works for Lynnette, Mark and I, and what worked for Jacob and I – was a commitment to the same ideological vision. Unfortunately, this is something that isn't often discussed in many entrepreneurial circles or in startups. Because when times get tough – and they will get tough – you have to remain committed to the bigger idea, the bigger vision and values that got you to take the risk in the first place.

A few weeks ago, a close friend of mine was telling me about a business she is thinking of starting. A registered dietician with a few years of experience, she sees a great opportunity for her and her passion, especially if she couples it with another person's expertise. She and this person have thought about going into business together. However, she has one hangup: she doesn't really like the guy that much. And nether do some other people. So, she's torn: on the one hand she could be successful and make a lot of money. But, she could also not enjoy the very work that's bringing her the success.

So I told her, "It matters who you do it with. Because at the end of the day, if finances are tight, if there are disagreements, or if things aren't going as well as you hoped, you want someone on board with you who you enjoy being with. You want someone you can stand to be around when the picture isn't so rosy. You want someone who can stay true to the vision and encourage you to be the best you."

Besides, if it's as good an idea as she thinks, she'll be able to find someone who fits that bill, and she won't have to settle for someone who's not worth it.