Relationship conduct: VCs, founders and beyond

As a long-time VC, I’ve had the chance to develop a pretty clear philosophy of how to manage relationships with founders in our portfolio, investing partners and entrepreneurs seeking funding. But when I zoom out, the fact is that there is a common principle that cuts across all domains, all levels of experience and all situations: RESPECT. And you’d be surprised how often respect isn’t given, with empathy left at the doorstep and self-interest the blinding priority. I can assure you that this is not a winning approach in either one’s business or personal lives, so hopefully you’ll find some resonance in what I’m about to say.

1. When approaching someone with whom you’d like to have a dialogue, learn as much as you can about them. Where they’re from, what they’ve accomplished, what’s seemingly important to them from business and personal perspectives, and then think about how you can weave your inquiry into the frame of shared interests. This shows that you took the time to research them, think about how to make a connection interesting and potentially valuable for both parties and that you’re not selfishly reaching out to “pick their brain” or any such one-sided affair. Rest assured that people who have accomplished a lot get these kinds of requests all the time, and the vast majority are of the character “Hi, I’m [so and so], I’m interested in [whatever] and I’d like to speak with you so I can [get your perspective / pick your brain / some other this-is-what-you-can-do-for-me ism]”. These people didn’t do the work to make a request of someone’s time personal to them. And this is a lost opportunity, looks terrible and is disrespectful of the person’s most valuable resource: their attention. Whether approaching a VC for funding, a senior business leader for a business contact or a friend’s parent for help with an internship or job search, invest the time to make an ask personal and contextual, professionally conveyed and with a hook that ties together your request with their background and interests. Otherwise, you don’t deserve any kind of a response, period.
2. If you are successful in connecting with the target of your inquiry, always follow up with a thank you note. It doesn’t matter whether the discussion went well, went poorly, didn’t result in a second VC partnership meeting, whatever — send the note. Life is a marathon, not a sprint, and the impression you leave, even in an unsuccessful interaction (vis a vis your stated goal), is an indicator of how you’ll handle disappointment and frustration in future endeavors. Also, it’s important to note that while you might not have gotten out of the meeting what you had hoped for, it doesn’t have to be an “unsuccessful interaction.” It can end up being a VERY successful interaction from a long-term relationship perspective. Many people have long memories, and a good impression that’s left even if the immediate goal isn’t achieved is incredibly valuable. It leaves the door open for future interactions, for starters. If I have a conversation with a founder and they were arrogant and defensive, I can assure you that if they send an email asking me for something or to re-connect, the likelihood of my helping out is approaching zero (absent them being struck by a thunderbolt of self-awareness that causes the tone of the outreach to be apologetic and healing, in which case I would re-think my “no future interaction” posture). The bottom line is that any and every collision with another human is a chance to make an impression and to handle both success and failure with grace and class. This extends to holding the door for someone, letting someone go through a tight space first or any number of chances we have in life to simply be considerate. Being thoughtful, appreciative and respectful is the best bargain we have in life — little upfront investment, with an unknown but potentially large future payoff.
3. Investors should leave companies better off for having met them regardless of whether nor not they fund them. The reality is that most of the time I am not interested in a particular business or idea for any number of reasons. The “why” does’t matter; I have my reasons. And as mentioned previously, my time is my most valuable asset, so I’m not going to use it on something about which I lack deep interest, passion and curiosity. I already have a portfolio of businesses and people for whom I feel deep responsibility, and they are my priority. If someone sends me a “real” opportunity (meaning not a standardized email, outreach that is tailored to me and appropriate given my very clear and publicly-shared interests, with an overview deck attached), I will review it and clearly say if I’m interested in an actual discussion. Again, most of the time the answer is no but if there is something about the outreach or the opportunity where I feel a little input might be helpful, I’ll share my pass along with some brief comments. Otherwise I will send a simple pass note but express thanks to the founder for having shared their business with me. Now, if I do engage with the founder and have a meeting or a zoom, I will always endeavor to be blunt and honest in my assessment, such that if we end up not working together than at least I’ve given them someone’s perspective who cares and has a lot of experience. I’ve always felt proud that many of the founders whom I’ve gotten to know but ultimately passed on their businesses still remember our discussions and the input I had given way back. I also take pride in founders who proved me wrong, but where our interactions helped them gain clarity that was ultimately a factor in their future success. What I find odd and, quite frankly, irritating, are founders with whom I’ve spent time, invested energy and effort in offering feedback during the diligence process but ultimately passed completely blowing me off after the fact. They were disappointed? Their feelings were hurt? Who knows. All I know is that I will forever remember these people who handled rejection, even done with empathy and care, poorly. It’s neither a good look nor a great indicator for future behavior.
4. Investors should give a quick “no” and be respectful of founders’ time and attention. Now this is one that makes me feel embarrassed as a VC. This generally falls into two buckets: (1) founder gets introduction to VC, and VC sets a call or meeting, reschedules the meeting multiple times, and stretches out even getting to the first interaction; or (2) where VCs decide to engage with founders around their business and fund raising plan. often having multiple meetings and/or calls, and don’t give the founders a firm “yes” or “no” until they are finally pushed to say something like “We just couldn’t get there this time; we really love what you’re doing. Please stay in touch.” Handling founders this way makes my blood boil. In (1), it’s clear that the VC was never super excited about taking the meeting in the first place, and should have just been honest and said “Hey, I know [referrer X] thought I’d be a fit here, but I’m simply not interested enough to dig into the business right now. Best of luck.” It is respectful to save founders the time, effort and hope of setting a meeting with [name your VC Associate / VP / Principal] if there isn’t bona fide interest. Just say no. It’s unpleasant to disappoint people, but it’s simply rude to purport to schedule a meeting when you have no intention of really opening your mind to the possibility of investment. With (2), there could be many reasons why this happens, none of them good from my perspective. Is the VC doing fishing in an area to learn more but never really intended to consider investment? Did the VC know they were going to pass but didn’t prioritize letting the founders know in a timely way because it would be uncomfortable and they had more important things to do? Regardless, founders should just have it in their head that, as a general matter, YESES COME QUICKLY AND NOS COME SLOWLY. It shouldn’t be this way but it kind of is. Sorry. By the way, this same dynamic applies to VCs seeking LP funding. In this case the shoe is on the other foot, with the VC acting as the founder and the LP acting as the VC. There is shitty LP behavior just as their is craptastic VC behavior. LPs out there, take note. I’m holding you to the same standard here.

Remember, these principles apply generally to all relationships. Sometimes being honest and kind is hard because disappointing people or telling them what they don’t want to hear isn’t fun. It may not be fun, but it’s called RESPECT. Nothing is more important in how you conduct yourselves in business or in life generally. Take heed, young professional. Get things off on the right foot and learn to live by this critical equation: HONESTY + EMPATHY = RESPECT.