1. Flirt More and Don’t F@CK till it Feels Good

Ideas are exciting. Beginning new ideas maybe even more so. The energy is high, dollar dreams are falling from the sky; honeymoon heels are a-clanking and people are ready to couple up and jump into bed together. STOP. Take a breath, zip it back up, and try to be a bit smarter. Believe me, I haven’t been. Excitement, life-circumstances, speed-to-market, whatever the reason or reasons may be, potential business partners, like relationships, tend to flirt too little and instead get right to it because they want to jump on something they think is hot. And like relationships, if you’re not properly protected, you can end up with something or someone your stuck with for a long time that has lasting repercussions on your life, or at the very least a few bad nights with a nut job.

Start with projects first. At least two, ideally. See how well you work together and interact together over a significant amount of time in different scenarios. Spend some quality time outside the project as well, try and get a deeper sense of who this person or persons is, where they are at in their life, and if their core values and behaviors aligns with yours. You don’t have to love them, but you should love, or really like, to work with them after all that time. When you feel that’s true, you are ready to begin a lasting and hopefully fruitful partnership. If there is a lot of pain, bumps, anxieties and uncertainties during these projects, it could be a good indication that it’s only a preview of the pain to come and you should just sip wine at home alone.

2. Don’t Work With Family Members

I don’t mean your own family (though that has its issues), but rather, partnering with other people who are related. In my nonprofit, my co-founder was much older and had a son a few years younger than me on a hiatus from college. Since he hadn’t spent as much quality time with his son lately, he thought it would be a great idea to bring him on. I loved the “kid” and so I agreed. Soon after, I regretted my decision horribly. They were fighting constantly: in our organization meetings, client meetings . . . basically all meetings. There were clearly some deep underlying family tensions I was unaware of, and I spent a huge amount of time being the mediator in their passive aggressive and openly aggressive arguments, and unresolved issues that had nothing to do with us or the organization. Productivity suffered, morale suffered, and meetings were awful. Luckily, the son went back to college and we resumed, but the memory stayed with me.

In my last startup, I partnered with two cousins. One was my full-time partner, and the other was more of a silent investor who did work when he felt like it. When my full-time partner and I started having various issues and arguments, the third would stay out of it and do everything he could not to speak a word in order not to rock the boat. While he would constantly call me up, complaining about his cousin for this or that, agreeing with me most of the time, when meetings were had, he would stay quite or be overly diplomatic and not speak his mind. During the process of me trying to leave the company and coming up with an amicable and fair departure, he couldn’t support one side or the other. Even worse, although he supported me behind-the-scenes, when push came to shove, he didn’t have my back at all in those final hours because, understandably, I was leaving but his cousin was forever. I got screwed badly for this decision.

3. Trust Your Intuition and Pay Attention to Red Flags

In both startups, there were individuals whom I didn’t like or had suspicions of based on their behavior patterns and just the general vibe. In one situation, I voiced my concern before we partnered but was overruled by the group because of what this partner could offer us. Only 3 months later my suspicions were confirmed and it, and he, ended up costing us our initial investment, idea, and ultimately the company.

In the second scenario, I wadded through a miserable 6 months building something with an older and more-experienced partner whose personality made me feel patronized and miserable, clinging to the hope that it would get better as we made more money and that because our idea was good and already making money, was worth taking a few psychological punches here and there. That was wrong. My views of what I deemed as major ethical and behavioral differences from the start turned out to have undermined me in the end, forcing me to get nothing for the sweat equity I put in for 6 months. Nobody is perfect, but more than one or two red flags and you should be seriously analyzing how healthy this relationship will be down the road.

4. Don’t Play the “I’m Good at This So You Do That” Game with Partners

I’m a creative type. A community builder; a “brand guy,” border-line artist. My ex-partners have always been the more “financial” and “business” type and thus, for lack of desire and an abundance of ignorance on my part, I had always trusted these people to make sound financial and business decisions for us all. BIG MISTAKE.

With my nonprofit, my partner (whom I am still friends with), while an amazing person in so many ways, made incredibly poor expenditure decisions and put us on a financially unsustainable path that ultimately led to us having to end the organization. I had no idea until 2 months before we ran out of cash and he finally confessed. In one startup, my partner wasn’t paying back our investor on the agreed upon time table and I was almost clueless as to what we were pulling in and bleeding out. There were strange expenses and even stranger excuses and a lot of money shifting going around. Because I lacked some essential knowledge and the desire to learn it, I couldn’t tell or smell bullshit and just trusted. When I was ready to leave, I was so in-the-dark about how our finances had been working that I couldn’t make an intelligent argument about where we were at and what I was truly owed.

I don’t care how much you dislike the field of finances or accounting (I almost hate them), know your business and where your money is at or it will come back to haunt you.

5. Get Your Sh@t in Order from Day One

My last startup operated as an LLC. We never drafted and signed a Founders or Operating Agreement in our entire 6 months together . . . so dumb. In the beginning it was all big dreams and bear hugs, the thought of us not being able to work it out seemed a remote and unlikely possibility. Fast-forward 3 months, and people aren’t sure what their roles are and who is doing what, or who was supposed to do this or that, and just causing chaos and resentment. Fast forward 6 months and people want to jump ship, but because we had never created even the simplest of blue prints, decisions were made and arguments abounded in the passionate fury with no structures or rules to fall back on. People took advantage of the situation and one another.

Operating agreements don’t need to be massive documents, they should be simple, but they should exist, and right away. They can be updated periodically as your business grows, roles change, and new challenges and opportunities present themselves, so nothing has to be fixed in stone. Talk about the difficult things like dissolution and if partners leave or are forced out while everyone is happy and motivated so it’s not too big of a buzz kill because it is significantly better to have these rules in place while everyone is happy and in-love than making them up on-the-spot when people want to kill each other.

At the end of the day

Partnerships are tough. A friend once used a baseball analogy to equate partnerships and startups: “most of the people can’t even get off the bench to play the game because they can’t agree on who is starting, who gets paid what, who’s the captain and who is wearing what number on their jersey.” Learn from your mistakes, that’s the mantra, and hopefully mine will give you a head start off the plate.