11 Ways To Avoid Entrepreneurial Divorce Court

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entrepreneur dating questions

It was three weeks ago when the e-mail hit my in-box.

I’ve been sitting on a business plan for a few years now. It’s a killer concept, driven by irreversible demographics, not trends, and there’s no rush, because the market is so big and so poorly served, there’s room for a lot of players and demand will only explode for decades to come.

But, I never moved forward, because as you guys already know, my dancecard’s been insanely full for quite some time. And, as much as I want to be attached and play a strong role in developing the mission and message, I don’t want to run it.

I needed a high-level operations guy, nobody fit the bill.

So, when, completely out of blue, a few weeks ago, I got an e-mail from someone who seemed to be my dream operations exec for that venture and he came looking or me, it just seemed too good to be true.

I’d have loved to jump right into action, brought him into the project and breathed life back into into. But, having been through the start-up and growth cycle a number of times, I knew better. Because in the world of entrpereneurship, all to often…

Those who get married without dating end up in a Christie Brinkley style divorce.

One of the biggest mistakes entrepreneurs make is jumping in the company bed with people that seem to be corporate soul mates too early, only to find themselves in small-biz divorce court a short time later.

No matter how well you get to know someone before committing to a project with them, you can’t completely eliminate the risk of things going bad. But, by taking your time and dating for a while, you can substantially minimize the chance of a really ugly breakup.

Here’s a short list of critical steps and conversations that should be explored for weeks, months or even years, before you make the call. How quickly you move through each conversation and stage will depend on the nature of the venture being contemplated:

Partner/Joint venture dating questions & steps:

  • Talk about relative strengths, experiences, skills and weaknesses. Take the time to get a really solid feel for who’s bring what, in terms of operating capability, to the table. Move beyond words and explore actions.
  • Define broader lifestyle visions and core values – You may be on the same page when it comes to the business, but to the extent possible, you also want to either be on the same page or be able to foster genuine respect for each person’s outlook on the role of the venture in their bigger lives and the value they expect to run both the business and their lives by.
  • Share venture specific vision, long-term goals/desired exits – Have each person write a detailed concrete description of the long and intermediate term visions for the company and, if appropriate, the desired exit strategies. Do this on paper and DO NOT DISCUSS them until they’ve been committed to paper. Then print them out and swap papers. Doing it this way will keep each person’s vision their own, rather than pressuring one or both people to relent to the perception of the other person’s public, maybe more strongly argued position. From these positions, now the real discussion can begin.
  • Check out resumes, references, online reputation and interests – As much you value your gut instinct, be smart and do your due diligence. You cannot imagine the surprises you’ll find.
  • Explore desired roles, titles and responsibilities – Share not only the bigger vision, but the specific roles that you see each person taking on in the venture. Then see if they work well with the skills and abilities that person brings to the dance.
  • Look at individual execution styles, systems vs cowboy orientation – One of the greatest sources of conflict between partners is not so much in what they want, but the “way” they go about getting it.  We all have our own operating styles and approaches. Some work well together, others are like water and oil. So, talk about operating styles and see if they mesh.
  • Reveal approaches to attracting and managing people – Just as operating styles can differ, so too can approaches to managing people. Share management philosophies, styles and how each of you have handled challenging situations. Make sure you both share at least a strong outlook on the role of people in the business.
  • Understand risk tolerance levels and profiles – Some people are cowboys and others are anchors in a storm. Talk about risk tolerance levels and how comfortable each of you are taking and living chronically with certain types and sizes of risk.
  • Explore nature of contribution: money, work, connections – Talk about exactly what each person is able to bring to the table. Then try to agree on the relative value of each type of contribution. This makes allocating ownership an easier process.
  • Discuss readiness, timing and hard-line restrictions – Just because two people connect around a shared vision doesn’t mean both are ready to take action at the same time. Talk about readiness and timing and confirm that both people are at a point where they are capable of moving forward.
  • Share what’s make or break and what’s open to discussion – Whether we admit it or not, we all have lines we draw in the sand. Sometimes they’re real, other times, they’re just posturing. When you’re dealing with someone you hope to share a venture with, try to keep posturing to a minimum, be forthright about what is non-negotiable and what is open to discussion. Excessive posturing can start off a relationship in a really bad place, so deal openly and honestly with those you hope to build a lasting partnership with.

One final major piece of advice, if possible, test the relationship first.

Even if everything above seems to gel, see if there is some kind of smaller project with a similar bent you could work jointly on, before committing to a fuller venture.

Talking about how you each work and what you value is one thing, but walking the walk is another. A lot of people like to think they are far more open, flexible, kind, tolerant, respectful, vision-oriented and skilled with people and tasks than they really are.  So, if there is a way to let “actual,” rather than “professed” experience be your guide…

Take the opportunity to gather information from not only words, but experience.

Now, all the above questions are factors that I’ve found, over years of entrepreneurship, have been very helpful to me. But, as always, you guys are my worldwide sounding board.

Do you see any problems with this list, or even with the notion of dating before entrepreneurial mating?

Have you had any experiences, good or bad, that bring this point to light?

What else might we add to the list to make it as robust as possible?

Let’s discuss…

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13 responses

13 responses to “11 Ways To Avoid Entrepreneurial Divorce Court”

  1. Yes, it is very true.

    I started working on my money making idea, had a friend who said he really wanted to be involved. Talked and talked about him being fully committed and now he is pretty much AWOL.

    He still calls from time to time saying he’s still very interested and will send me some samples soon, but I’ve stopped looking for them.

    Problem is, I’m having to go back and do the things he said he was going to do so I can’t move forward on the things I needed to be doing.

    Lesson learned.

  2. Justin says:

    You are exactly right, you have to be very careful about choosing a partner. Luckily, the one I have is very reliable and effective. I don’t think I’ll be having a divorce any time soon!

  3. @Stephen says:

    This is a treasure-trove! I have been considering some partnerships and joint ventures. Now I am armed with the proper way to initiate the contact. Thanks.

  4. Tony Maro says:

    We brought in a business consultant / venture capitalist a while back who we all thought was going to be the be-all-end-all for us. We were all excited over the prospects he brought to the table, coming from our target market and he had started two companies both which sold for over $100 mil.

    He presented very nicely. We responded with “looks great! Give us a week to have our attorney’s and accountants look it over.” He was very offended that we would have experts look over his proposal and said as much.

    We told him to take a hike. If he had truly had our best interests at heart, he would have encouraged us to have our accountants look it over first.

  5. […] 11 Ways To Avoid Entrepreneurial Divorce Court Talking about how you each work and what you value is one thing, but walking the walk is another. A lot of people like to think they are far more open, flexible, kind, tolerant, respectful, vision-oriented and skilled with people and … […]

  6. Adrian says:

    Good stuff. Always best to layout expectations at the beginning. Makes it easier to say yes or no upfront and later on.

    On the opposite side, I have a friend who shared a brilliant, revolutionary idea he has. I’ve been pumped ever since, but he’s been slow to do ANYTHING. We’ve “dated” and could fit, but this inaction is a big turn-off.

    Jonathan and community, how can I get the idea moving without a) leaving him out (thus violating all my moral principle) or b) getting the idea going with his consent, but without him onboard?

    Thanks for any advice. I enjoy the convo immensely.

  7. Testing the waters in a business is even more critical when the proposed partner is a relative. I have never been successful getting any of my relatives on board with my businesses mainly because they didn’t want to be scrutinized for suitability, much less “date” first.

    Even as employees with clearly defined tasks, my relatives fell short. I once fired a niece and deducted her portion of my phone bill from her pay when she failed to respect my rule about not calling her boyfriend while on duty, especially since he was in another zone.

    Your list is not too robust. It’s far better to get as much clear in the beginning than it is to regret the damage that can be done to your business.

    The most important things on your list are requiring them to write out their goals, submit resume and references and exploring the exact nature of their contribution to the business.

    Those who refuse to comply with these requirements eliminate themselves. Those who make it through are now ready for a “date.”

    Go Jonathan!

  8. Gail says:

    Well, I have learned the hard way, that what people say they will do, and what they do are two different things. It is like courtship, and basically if it’s worth it you can work things out for the great good of the business. In the end, there are still some things that no matter how careful, you just can’t predict until you are “in-bed” with that person. So my suggestion is to go with your gut, the initial instinct that tells you what you think. Unfortunately we often let our minds convince us that someone is what we want, that gets us into trouble!

  9. Laurie says:

    I am starting a new business with a friend that I have worked with for the past 5 years. We taught together working on the same team. We know each others strengths and weaknesses. We respect each other and know each other well. We are a great fit in that her strengths and the aspects of the business that she likes the most are different from my strengths and what I like in the business. We made a pledge to give “truth in love” not hangin on to things that bother us or hurt our feelings but to lay it on the table and discuss it before it gets big and out of control. We’ve already done this once and it ended up working out and all was good. I think you really have to be honest and trusting. You have not worry about a title or who looks like the top dog but look at what is best for the company. If you can’t do that, hang it up.

  10. Jim Carlson says:

    As a fiercely independent musician and internet marketing consultant, I have been approached several times to ‘join forces’ with others.

    People are drawn to entrepreneurs because it is an appealing alternative to the 9-5 lifestyle, however, they rarely see the hard work, dedication and discipline it takes to succeed.

    The biggest question I ask myself is: Do I have the time to commit to another project or person? In the end time is money, and time spent on a new venture takes time away from current projects. Is the time investment a wise choice?

    Your article is a great checklist and I will refer to it often.

  11. […] 11 Ways To Avoid Entrepreneurial Divorce CourtI’ve been dealing with the entrepreneurial bug for a few years, but I haven’t quite found the right people to make any ideas go. […]

  12. Jeff Flowers says:

    Two words — PRE-NUP

    (or is that one word, with two syllables?)

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