One of the first pieces of advice most people will give you when you set out to become an entrepreneur is to “get yourself a few good mentors”. While I wholeheartedly agree with this advice and it can create a ton of good, very few people talk about the bad that can come from it if the proper lines are not drawn. While it has been several months since my experience which I will share some lessons from, I admit that I still harbor some negative emotions as I write about it. I will try my best to remain objective and unbiased, as one of the greatest lessons this particular mentor taught me is that “there are two sides to every story”.
I’ll skip to the end of the story since the journey itself (while probably somewhat entertaining) is less important than the lessons that can be taken from it. After founding, growing, and successfully running my last company for almost 10 years, I found myself a couple months ago with zero control or power (despite being the founder and majority shareholder). I joined the ranks of some prestigious (and some not so prestigious) entrepreneurs that had been kicked out of their own companies. I can trace the situation back to a series of (admittedly masterful) moves and manipulations carried out by my most trusted mentor/advisor/partner of the last 10+ years. It was unclear to me where the lines between the roles of mentor and partner started and stopped, and I definitely didn’t do the things I should have to protect myself as we crossed them.
But before anyone feels too bad for me, please don’t :) I accept 100% of the responsibility for what happened and I look at this as a massive learning opportunity. This same mentor taught me that “from bad comes good”, and I couldn’t be happier with where life is headed with my new endeavor at AI Foundation.
So what would I have done differently? Here are my top five things:
1. Avoid It All: Separate Business And Mentorship
This is a simple one: Don’t do significant business with your mentors! This is also a really hard one for me. I tend to surround myself in business with people I know, I like, and I trust. A good mentor is usually all 3 of these things and is often the first thought for an entrepreneur when building a team for their new venture. Whether it’s making them an advisor, business partner, executive, consultant, etc., it almost seems obvious to put your mentors in your key roles.
The problem is this: the attributes and behaviors that make a great mentor are usually VERY different than the attributes that make a great advisor, business partner, executive, etc. If it’s your company, you need to have an authoritative role over your advisors, executives, consultants, etc. and they need to be willing to follow your lead and vision at the end of the day. If you have a business partner, you need to have an equal role and equal respect. The problem with a mentor is that you have already established a subordinate role to them, as they have been the one giving you direction and advice — not the other way around. This is very hard to flip. (*Although I will say, one of my mentors, Lloyd Taylor — who is an incredible person — was able to successfully be a mentor, an advisor to the company, and a member of my executive team at different points in time, and did it brilliantly. But this is rare.)
In my case, I brought my top mentor from the past into my company, first as an advisor, and eventually as a business partner. While this was good for the company at the time and he added a lot of value, he also never really got past treating me as the mentee. He never truly had confidence in me to run the company, never truly believed in my vision, and spent a lot of time telling others what I was doing wrong. Business partners should have mutual respect and belief in each other, and that was never possible after the mentor/mentee dynamic had been established.
But the reality is you are probably going to do business with one of your mentors at some point, so…
2. Keep Values Aligned
…as you are transitioning from mentorship to partnership, you first need to make sure you fully understand each other’s core values. When you begin to have conflicts (see #4), this will be critical for resolving them efficiently and with less pain. One important thing that nobody ever told me (and I had to learn the hard way) is that core values change over time. Aligning your values is not a one time exercise — it must be done often! Major life events related to health, family, business, finances, etc. can completely change what an individual values most and how they make key decisions.
You should go through a variety of difficult hypothetical scenarios before you cross the line into business (and this goes for any type of business or personal relationship). It’s always easiest to discuss a difficult situation and agree on a desired outcome when you are not actually in the difficult situation. Talk about what happens when your values change, when your financial situation changes (for better or worse!), when there are family issues, health issues, or even death. Agree on how these hypothetical situations should be handled and put it on paper in a legal agreement (see #3)!
In my case, while my mentor/future business partner and I were very well aligned on most of our core values from the beginning (such as honesty, transparency, ethics, etc.), we knew we diverged in one area: where he valued making profit, I valued reinvesting in culture and growth. We agreed this was ok and we would focus on the long game and the culture. However, we failed to re-align our values along the way and at some point profit became more urgent to him and we found ourselves completely out of alignment in our visions.
3. Paper Everything (And Read Everything!)
A wise man once said, “If it isn’t written down, it didn’t happen.” This is a hard one for me. I generally default to trust and a handshake, and believe that most people will do what’s right and honor the spirit of an agreement. And honestly, this has worked very well for me 99% of the time. Unfortunately it’s the 1% that gets you, and that’s what happened here.
It’s easy to start working with a mentor informally and to build a lot of trust over time without any contract. But if you are going to cross over the line between mentorship and partnership (that could be as simple as stock options, an advisor role, commission, etc.), it’s time to put together a formal legal agreement. Any mentor who disagrees with that might be too far down their potential curve (#4)!
The reality is that people change over time and what might seem clear and obvious between two trusted people when they agree on something may fade away over time. Or worse, the intentions or motivations of those parties may change over time, all the way to maliciousness. And worse yet, the parties themselves might change over time through investment, M&A, new hires, etc. This is why lawyers make the big bucks, and they will often feel like a waste of money until the day one of their agreements saves you. Make sure you understand what you are signing and don’t be afraid to seek a second opinion from additional counsel.
In my case, my mentor and I did everything right in the beginning by creating a clear partnership agreement that covered all the difficult cases as we moved into business together. But unfortunately over time (due to corporate restructuring), that agreement became invalidated. My fatal move was signing a new agreement (that my partner and advisors had prepared) without reading it because I blindly trusted them. I’ll spare you the details, but it was not a good outcome.
4. Know When To Part Ways
It’s well known that every great student outgrows their teacher, but it’s not well known what the ramifications of that can be on a business. The curve above shows (in my opinion) the potential of a healthy mentor/mentee relationship over time. The beginning of a mentorship creates massive learning opportunities in both directions, and I believe this is the healthiest period as both individuals are growing in potential as a result of the relationship. In the majority of mentorship relationships (although there are plenty of exceptions), mentors are closer to the end of their careers whereas the mentees are closer to the beginning. So it’s just a matter of time before a mentor starts to decline in potential, while the mentee continues to grow.
This crossing of potentials can occur months, years, or even decades into a mentorship. Depending on mindsets, this can begin to create conflict. Mentees become increasingly frustrated with the performance or lack of growth opportunities being provided by the mentor, and the mentor starts to feel unappreciated and unheard as the mentee makes decisions that diverge from their advice. This is a sign that it’s time to call the relationship a success and end it. Moving beyond that point will only cause animosity, resentment, and pain — except in the very rare case where the mentor and mentee can actually flip roles (which I’ve only seen happen successfully a couple times).
In my case, I reached this point a couple years ago. My mentor/partner was not performing as well in his role, we were having trouble communicating at the higher pace of business, and he was building up a lot of animosity and resentment toward me that I wasn’t aware of. While we did discuss the idea of retirement, there was always a reason why it was not the right time. I felt like I owed it to him to make it a mutual decision based on everything he had done for me. I was never able to make the hard decision to force a conflict and end the relationship. Our business and our employees paid a high price for my lack of action, and I paid the ultimate price in the end.
5. Diversify Your Mentors and Partners
The last lesson I will share is one that becomes important as you experience success. A funny thing starts to happen when you begin generating significant value: greed. Greed can drive people to behave in ways that you’ve never seen before and that are inconsistent with their proclaimed core values. Mentors, advisors, partners, executives, and even employees, who you’ve trusted for years, can one day completely change their motives. They will often form alliances with others they trust to further their chances of gaining more (see reality TV shows…). They will create echo chambers within their groups and begin reinforcing a warped view of reality in order to justify their means. There’s nothing more scary than someone you totally trust suddenly acting very differently, and there are very few things that can cause that (fear, stress, drugs, and greed!)
I’ve not yet found a way to predict how someone will act when there are millions of dollars at stake other than putting them in that situation. So in order to protect yourself, you must diversify the trusted group of individuals that you surround yourself with. Find people from different backgrounds, different locations, who have not worked together before, and who have no loyalties to each other. Not only will that bring you the most diverse perspective, it will also help protect you from that group forming alliances against you that could be fueled by greed. This sounds a little paranoid, but I’ve seen it happen way too many times.
In my case, all of my mentors, advisors, and business partners came from the same network and had a lot of history together (far before I came along). So when push came to shove and there were hard decisions to be made, their default was to listen only to each other and very few actually sought out the truth directly from me. I also had very few mentors outside this group that could give me unbiased direction (because I didn’t follow rule #1), and was left with little support through this toughest part of my professional life. I don’t wish this feeling on anyone.
And So Life Goes On…
I’ll conclude with one last piece of advice: get yourself a few good mentors! While there are things I would obviously do differently, I can’t begin to express how much I learned and how much I appreciate the mentors, advisors, and business partners I’ve had. I really am who I am because of them, and this includes the main character in my story above. The time I spent with him in the green part of the curve was invaluable, and I am the only one to blame for letting it get into the red (in the critical path of the business, with unaligned values, without proper legal protection, and with no other mentors to watch out for me!)
But all in all, if I had to choose between no mentorship at all or doing it all the same way again, I would land right back in this same spot :)
Now on to bigger and better things!