There’s a tenuous balance between telling someone what to do and giving advice. It’s especially difficult as a mentor, especially if you’ve previously been a CEO and are used to being “the decider.”
As a mentor, you aren’t the decider. The CEO you are mentoring is the decider.
This dynamic is also true for many board / CEO relationships, where the board wants the CEO to make the ultimate decision. As I’ve often said, my goal as a VC is only to make one decision about a company – whether or not I support the CEO. If I do, I work for the CEO. If I don’t, it’s my job to do something about the CEO.
While this is nice in theory, it’s difficult in practice. One of my strengths is that I tell a lot of stories. One of my weaknesses is that, according to my wife Amy, my stories go on 20% too long (she is correct.) Here’s an example.
I’m at a board meeting. The CEO, which I love working with, is trying to figure out what to do about a particularly thorny issue. I tell a story. He reacts with a little more data. I tell another story. Another board member asks a question. I tell another story. This one goes on a bit too long.
The CEO looks directly at me and says, very firmly, “Will you just tell me the fucking answer for once?”
I tell him the answer.
He was looking for specific, actionable advice. I was telling him stories. If he spent enough time processing the stories, he might be able to come up with the right answer. Or, since they are stories, he might draw the wrong inference and decide to do something different from where the stories were leading him. This CEO was aware of that and, in real time was having trouble processing the point of the stories in his context.
Fortunately, this CEO was self-aware enough to ask for specific, actionable advice in a moment where he needed it.
Two mentors in one of the Techstars programs were both people who I knew well. They hated each other as a result of being co-founders of companies that had been bitter rivals.
Each company was successful, but their paths ended up being very different. These two co-founders hadn’t interacted with each other, but the CEOs of each of their companies had some rough interactions. As a result, each of these co-founders thought the other was an evil person.
Each of the co-founders was technical, extremely smart, and capable. Not surprisingly, they gravitated toward mentoring the same companies.
After a few very awkward moments, I encouraged the two co-founders to let their pasts be history and to move on. I knew them each pretty well and expected they’d like each other and get along if they had an opportunity to reset things. Being mentors to the same company gave them this opportunity.
It turned out that they loved working together. At some point, the co-founders talked about their past. They had never actually met, and each realized that their emotions were a function of the hostile relationship between the CEOs. Since they were channeling these emotions, they realized this was a self-limiting perspective.
They became friends. In a few cases, they’ve been mentors for the same company. It’s been a great example of moving beyond whatever your past is and accepting each other as a mentor in a new shared context.
Last month I took two weeks completely off the grid. As part of it, I spent some time working on my next book, Give First. As part of that, I finished up the sections on Deconstructing the Techstars Mentor Manifesto. While I wrote a draft of this post over a month ago, It felt appropriate to publish this, and the next few Mentor Manifesto posts, after a wave of Techstars Demo Days that just happened.
#15 is “Be Optimistic.” It sounds simple, but it can be incredibly difficult.
As a mentor, your job is not to solve a founder’s problem. It’s to help. It’s to listen. It’s to provide feedback and data from your experience.
You can do this from many different perspectives. However, given the stress on a founder, it’s best to do this from an optimistic frame of reference.
Here’s an example of the challenge. You are a mentor to Maria, who is struggling with her co-founder Stephan, who has become unpredictable, inconsistent, and subdued. Maria feels alone, both on a day to day basis as well as in dealing with Stephan (there are only two founders in this case.)
As a mentor, you had a difficult co-founder experience in your last company. While the dynamics were different, it ended poorly with your co-founder leaving the company. While you haven’t spoken since you split up, your business was successful and acquired for a life-changing sum of money for each of you.
Your co-founder struggle is one that didn’t work out between you and your co-founder but was ultimately financially rewarding for each of you. You carry around this conflict in your head. On the one hand, you are pessimistic about where things between Maria and Stephan will end up. On the other, you know that even if their relationship fails, the company can still be a success.
You also learned a lot from your experience with your co-founder. Each of you made mistakes in approaching things during your conflict period. This hurt both of you and negatively impacted the company for a while. Your struggle with each other was public, and it ruined several other relationships with people who felt like they needed to choose sides.
Being optimistic in this context is difficult. But it can be done. Start from a positive frame of reference. Talk openly with Maria about the things that you and your co-founder did wrong as you tried to address your conflict. Be clear about how things could have turned out differently. Be introspective in your discussion and speak from experience, instead of giving advice. Remember to reinforce that even though your relationship with your co-founder ended up failing, your business was successful.
Let Maria have her experience as she tries to resolve things with Stephan. Try to be a positive influence in the mix to encourage her to do the work involved, even if they end up parting ways.
There’s a longer article on HBR by Adam about the general concept of generosity burnout. It’s a good read and it’s helpful to me as I start working on my next book, Give First.
Several people have picked up from the tone of some recent blog posts that I’m wandering up to the edge of this. I’m at my limit emotionally and made a conscious decision a few days ago to change modes through at least the end of Q2. I cancelled all my work travel in Q2, uncommitted to a number of things that weren’t already in process, and generally decided to focus my energy on what I’m currently working on, rather than add to anything new, especially in the “this could be fun but I don’t know why I’m doing it” category.
I already say no 50+ times a day. I’ve also tuned out a ton of noise around things I can’t directly impact. That’s not the issue. Instead, it’s remembering to ask myself “do I want to do this while I’m in my current mode” at least twice before I say yes to anything.
Periodically, at the end of a conversation, someone will ask me, “Is there something I can do for you?” I used to answer with “Do something that is helpful to something or someone in my world.” I usually get a pause and occasionally get a response similar to “I’m not really sure what to do to help you.” Over time, I modified my response to “Do whatever you think is useful to grow your startup community.”
I thought this was a good answer until someone paused, looked at me directly, and said “I’ve been listening to you talk about GiveFirst. I think I get it, but I feel like I don’t know how to help you.”
I realized that for many people, the vague answer I was giving wasn’t helpful. I was trying to create a lot of space for them to do whatever they wanted to be helpful. But the person, like many of us, was looking for something tangible to grab on to, in order to start with something specific that could cause them to feel like there was no question about them helping.
I now try to respond with something specific the person can do. I try to incorporate it into the person’s work. I’ll ask some questions to try to identify something that I know will be helpful to me, but also helpful to them. This is particularly easy for me, since doing something that helps with my global goals around entrepreneurship, rather than a specific, narrow task, helps me.
The magic trick is that if it’s helpful to them, they’ll realize that GiveFirst isn’t altruism. By helping me, they are helping themselves, and the flywheel of GiveFirst begins to turn.
It’s been a while since I wrote a post deconstructing the Techstars Mentor Manifesto. The last one I wrote was number 12 of 18: Know What You Don’t Know. Say I Don’t Know When You Don’t Know. Since I’m now working on the first draft of my next book #GiveFirst (or maybe it’ll be called Give First, or GiveFirst – I haven’t decided yet) it’s time to get my shit together and write the last six posts.
Throughout Techstars, we tell the founders that “it’s your company.” The implication of this is that they make the decisions about what to do. Everything they hear from mentors is just data.
A lot of mentors are successful CEOs. As CEOs, they are used to being in control. However, in the context of being a mentor, they don’t control anything. The best they can do is be a guide.
Interestingly, the best investors understand this. One of the lines my partners at Foundry Group use regular is that we only want to make one decision about a company – whether or not we support the CEO. If we support the CEO, we work for her. If we don’t support the CEO, we need to do something about this, which doesn’t necessarily mean fire the CEO.
In the context of being a mentor, you still get to make one decision, but it’s a different one. You get to decide whether or not you want to keep being a mentor. Assuming you do, your job is to support the founders, no matter what.
Ponder the following situation. The company has three founders. While one of them is CEO, it’s not clear that the right founder is the CEO. In addition, two of the founders (the CEO/founder and one other founder) are struggling with the third founder.
It would be easy to size up the situation and tell the founders what to do. But that’s not your job as a mentor. Instead, your job is to guide them to an understanding of the situation. The best mentors will invest time in each founder, keeping an open mind about what the fundamental problems are. You’ll surface the issues, guiding the founders to understand that there are real issues, what they are, help them talk about them, and help them work through them to a resolution or a better situation.
You won’t try to solve the problems. That’s not your job as a mentor. But you will be a guide. At some point, it will be appropriate, as a guide, to say what you would do if you found yourself in a similar situation. But, as a great guide, you won’t force this outcome, nor will you be judgmental if the founders go down a different path.
Remember – you get to make one decision – whether or not you want to keep being a mentor.
I’ve started working on my next book, currently titled #GiveFirst: A New Philosophy for Business in the Era of Entrepreneurship. As a result, my brain is especially tuned to good examples that show a particular aspect of what we refer to as #GiveFirst at Techstars.
I was working at my desk the other day when Krista Marks, the CEO of Woot Math came in and said hi. We are investors and Jason is on her board. Krista and I have been close friends for over a decade and I always have time for her no matter what is going on.
She wanted to tell me a story about #GiveFirst so I stopped what I was doing, sat back in my chair, and listened. After she told me the story, I smiled and asked her if she was game for me to put it up on my blog as an example. She said yes and after she left I put a draft title in WordPress to remind me to recreate / write the story when I had some writing time.
Later that day, Krista sent me the full story, which follows, in an email. While the example is a simple one, it captures the essence of #GiveFirst nicely. Krista’s words follow.
A couple of weeks ago, I had just arrived in San Antonio to setup and exhibit Woot Math at a conference.
But I also desperately needed to find a conference room to use in the morning for a video presentation and live demo of Woot Math for the board of directors of NewSchools Venture Fund. The convention center didn’t have a room or WiFi I could rent in the center, but they pointed me to the Marriott across the street. The Marriott did have a conference room available for rent. Awesome! Here’s where the story should end, right? But then came the asking price: $400 for the room, $200 for WiFi, and $250 for a phone! I rejected the offer out of principle.
At this point it was after 4:00pm the day before I was scheduled to present at NSVF, and I was starting to worry.
My colleage Tom suggested, “maybe there’s a startup space that rents rooms.” We searched and found Geekdom:
No phone was listed but there was an address; with time running out, we decide to hop in the car and drive there.
When we arrive, it’s close to 5:00pm. I hurried up to the 7th floor of a new, modern office building. The door was locked, but there was a large window, and I caught someone’s eye. I explained that I’m the CEO of Woot Math, a startup in Boulder, and I need to a room to rent for an hour for an important meeting tomorrow.
I’m immediately welcomed in, and taken to Luke Owen, the COO of Geekdom. Luke asked if I’m involved in anyway with Techstars, and I’m pleased to share that I’m a mentor for the Boulder Techstars program. It turns out that Luke is one of the program managers for Techstars Startup Next in San Antonio, which runs it out of Geekdom.
After chatting and sharing lots of common, small world connections, Luke took me a cool conference room with high-ceilings and a large window. I’m told that it is mine for the day; I’m leant his VoIP conference phone; and I’m encouraged to help myself to coffee and the kitchen.
At this point, I’m pretty overwhelmed by Luke’s warmth and generosity. I say something like, “Wow. I honestly don’t know how to thank you. Is there anything I can do for you?” It turns out he’s working with TeachTag, an ed-tech startup helping teachers be more organized. Luke asks if he can connect me with the founders Aaron Schuenemann. Here’s the lovely introduction that Luke sent –
It makes me so happy and proud to be part of the Techstars community and it such a powerful reminder of how entrepreneurs make the world better. Every day.
I woke up feeling subdued this morning. I didn’t know why but after talking to Amy I realized that the emotional impact on me of the horror in Nice is weighing on me. Amy described her connection to it to me – she’s been physically in the same spot that the tragedy happened – and even though we are far away, something very personal hit home about the whole thing.
We are long-time friends with Fred and Joanne Wilson. After my call with Amy, I did my daily news routine, which includes a few minutes in Feedly skimming all the blogs I subscribe to and reading the ones that catch my attention. Both Fred’s and Joanne’s did today.
I read Joanne’s post from yesterday titled Pledge 1% first. It perked me up a little and made me smile, as Pledge 1% is the evolution of the Entrepreneurs Foundation of Colorado which I co-founded in 2007. My partner Seth Levine took the lead a few years in and, with a few other people including Ryan Martens, the co-founder of Rally Software, have evolved our model into a national one. It makes me very happy to see it expanding to NYC in a significant way with Joanne supporting it. If you are in NYC and interested in learning more, attend the Pledge 1% Happy Hour on July 27th.
I then ended up on Fred’s blog. He wrote What Do You Do? What Do You Say? about Nice. In many of the recent attacks and violent situations I’ve felt emotional kinship to Fred. He’s written about things right away in words that are heartfelt and reflect my emotions. I’ve commented on the posts, supported the charities Fred has pointed out, such as the Fund for Nice, and occasionally written a post pointing at them. But I’ve definitely been more reserved about my emotions as it takes me at least a day or two to process them, and at that point the world has often moved on from the immediate aftermath of whatever happened.
Today I didn’t feel like waiting. Amy and I have a quiet weekend together and plan to have dinner with my parents and aunt Cindy/uncle Charlie on Saturday and then brunch with David and Jill Cohen on Sunday. These are all people we love deeply and we get to be with them in a very safe and comfortable context. I’m going for two long runs, will spend time finishing up the third edition of Venture Deals, and just being with my beloved.
Against the backdrop of this, the Nice events are extremely unsettling. Fred ended his post with a powerful introspection / call to action:
There is an epidemic in the world, a sickness that is spreading and afflicting more and more people. It is mental illness. We need to diagnose its cause and treat it. Until we do that, we will be facing more of these mornings. I think many of us are wondering what we can do to help with that. I certainly am.
I hear entrepreneurs use the word disruption on a daily basis and continuously hear the cliche change the world. In entrepreneurial circles, it’s clear to me that violence, hatred, and discrimination or whatever you want to label it is another category where we need to pay attention to disruption before it changes the world in ways we don’t want it to. Or that we need to change the world away from the themes that are starting to appear on a very regular basis. I don’t have answers, but I know I’ll have reflections this weekend.
This is my last blog post of 2015. I’m taking a break from a bunch of things for a while.
#GiveFirst is the title of my next book, which will come out sometime in 2016. I’ve started working on it and realize that I have a finite amount of daily writing energy. Since I no longer wake up every morning at 5am (I don’t use an alarm clock anymore), I have a less predictable morning routine. As a result, my writing times are more random and chaotic, which I like, but means that it’s harder to have big chunks of time on a consistent basis.
For now, #GiveFirst wins over blogging.
But that’s not the only thing driving my blogging hiatus. After over a decade of almost daily public writing, I feel like I need a break. Some is boredom, some is a burdensome feeling around an obligation to an almost daily habit, and some is the lack of freshness I feel in my writing.
I’ve always enjoyed multiple forms of writing – micro (tweets), short (blog posts), medium (magazine articles), and long form (books). I also write a lot of other stuff all day long (mostly emails) and the majority of my communication is written, which I prefer much more than verbal. But I feel like I’ve hit a wall of some kind. And, whenever I hit a wall, my first instinct is to shake some things up.
As I approach turning 50, which happens on December 1st, I’m finding less enjoyment from short bursts of communication and more from just spending time with friends, with Amy, or by myself. So, through the end of the year, I’m going on a diet. No more blogging. No more twitter. No more commenting on blogs. No more social media of any sort. In addition to stopping generating content (and plenty of online exhaust fumes), I’m going to stop consuming it also.
I have no idea what will happen on January 1st, 2016 – that’s part of the fun of it for me. A ten week reset on this front will be interesting to me. For now, 100% of my public writing will be dedicated to working on #GiveFirst and I’ll explore a new rhythm by subtracting out a lot of other stuff.
See you in 2016.
Techstars Boulder Demo Day is this week. It always marks the true end of summer for me and it’s a reminder that I stalled out on my Techstars Mentor Manifesto series of blog posts.
The last one I wrote was #11: Clearly Commit To Mentor Or Do Not. Either Is Fine. It’s an important life rule – either commit or don’t commit – but choose! Mentor Manifesto #12 is also a good life rule: Know What You Don’t Know. Say I Don’t Know When You Don’t Know.
We all know Mr. Smartest Guy In The Room. I find him insufferable and have nicknamed him Mr. Smartypants. Unfortunately, there are a lot of Mr. Smartypants in my world as he inhabits the bodies of some entrepreneurs and the souls of a lot of investors. Regardless of who he manifests himself in, he’s still tiresome and when there are two of him in the room, watch out.
The best mentors are not Mr. Smartypants. While a great mentor knows a lot and has had plenty of experiences, she’s always learning. The best mentor/mentee relationships are peer relationships, where the mentor learns as much from the mentee as she teaches the mentee. There’s no room in this relationship for Mr. Smartypants.
I know a lot about some things. And I know very little, or nothing about a lot more things. My business and technology experience is deep in software, where even the hardware companies we are investors in (Fitbit, Sphero, Makerbot, Glowforge, littleBits, and some others) are what we like to refer to as “software wrapped in plastic.” At the essence of it all is software and that’s what I know best.
But I don’t know all software. And I especially don’t know vertical markets. We’ve consciously stayed horizontal in our investing, being much more interested in our themes which apply to many different vertical markets. But ask me about a vertical market, whether it be entertainment, real estate, insurance, auto, food, energy, or financial services and I’ll often approach it with a beginners mind.
In some cases I think something generic will apply to a vertical market. But when asked about something structural, even though I’ve had lots of different experiences, read a zillion magazine articles over the years, and might have some opinions, as a mentor I’m quick to say I Don’t Know, unless I’m confident that I do.
When I find myself in an “I Don’t Know” situation as a mentor, I immediately start trying to figure out who I can refer the entrepreneur to who might know something about the situation. And, just because I don’t know doesn’t mean I’m not curious about finding out more. I’ll often stay engaged and hear what the mentor has to say, just so I get the benefit of having more data in my head to play around with in the future.
I say “I don’t know” or some version of it at least daily. How often do you say it?