The Importance of Cliches
Today I am thinking about the most cliched things VCs say and perhaps either should say less, say differently or say more specifically. This could become a list, but today let’s start with three that popped into my Sunday brain.
First Cliche: How Can I Be Helpful?
This is the cliche line every VC worth our salt utters daily if we are doing our jobs at all. Like all cliches, this question is overused and has lost meaning to most as it often feels performative.
But, it is also the question VCs should be thinking about in…
Every first call with a new founder
Every board meeting even its the 100th one
Every time you hop on the phone with a firm colleague
Weird moments that emerge out of context (the key to realizing you are meant to be in VC!)
A VCs job is to pick well. Some stop there.
Some think stopping there is the key to being a great VC (a good topic for another time).
Most VCs ask “helpful question” to try to add value (another huge cliche). The tricky part is that VC as an industry structurally spreads its funders thin across many opportunities that take 5 years — or sometimes 15 years — to develop, especially at the early stages. So to add value for real, I believe that if a VC is not even asking the “helpful question” in their head (or you are explicitly trying to avoid it), it’s never going to happen. If you are faking the desire to help, are just really curious and want to make money, you are probably not meant to be a VC.
I feel immediately embarrassed now every time I hear myself say “let me know how I can be helpful” or “I’d love to be helpful.” I think I convert to being helpful more than most, but also say it more than I can deliver. That may be a casualty of optimism. Or the industry. But I embarrass myself these days regularly when I hear the words come out of my mouth.
I think about when and how I utter an offer of help a lot more these days. Last night in a rare in person, very COVID safe meal, I said those wt someone who was not asking for help.
Here’s why (my journal entry from earlier today):
Seeing Amy was wonderful. I found myself wanting to proactively help her and her husband, not that they need it. They will be just fine without any help from me. But when I see talent in someone who gives me energy, who is important to someone in my life even if I only know them a little, I find I want to help. Even if its not in my best interest from a time on return standpoint. Amy gives me energy. I would love to help her out her moment (which some might call a rut)
For the last month, I am trying to say helpful less and put more punch behind it with fewer people. On calls, on emails, in Twitter DMs. The cliche will continue but hopefully it will evolve as well@
Second Cliche: He’s a Good Guy
AileenLee has taught me to avoid saying “he’s a good guy.”
At first I thought, I get it, we are trying to come up with a non gendered word that relates to all of us. But then I realized it was so much more. This is the easy way to describe anyone you think is ok, but its also a shiftless way to speak.
As Mo Koyfman once asked me, “Kara, how would you rate x for this job, no 7s allowed!.” He or she is a good guy is an easy way to convey “don’t know that person well, but they have a good reputation” or “have met them at x party or zoom, seems cool” or “friends with the founders of airtable, clubhouse, figma” and they say good things. It enables you deem everyone a 7, whether you know them a little, a little more than a little or not really.
It’s problem is not so much that there is anything wrong with the words, but rather that it allows us to embrace lazy thinking, to not pick a side, to play forward the narrative out in the world.
Instead, I now force myself to think of a more specific way to describe that person, otherwise I opt out.
If I don’t know him or or her other than high level reputation or hearsay, I simply say “I do not know enough.”
OR
If I know her or him enough from primary interactions, but not well enough to be a well informed advocate, I err on the side of positive, but specific.
For example
She’s clever, a hustler. She ran one of the All Raise operator events and heard great things about her follow-through and creativity in building an invite list. While I have not worked with her directly, based on what I have heard, I’d give her a shot to win that deal. Because she is likely to work harder than the next guy at that fancy logoed firm.”
Third Cliche: Every Blog Post or Slide Must Have Three Points
I usually write a manum opus type blog post. I am perfectionist and since having kids, have gotten far too deliberate as to when I write because I do not want my posts to be mediocre. I usually write ones that takes dozens of hours of thinking and research. Sometimes real publications publish them. Sometimes I get a lot of positive reaction. Sometimes I take 100 hours and get 3 likes on Twitter and forget to post on LinkedIn.
In the last six years, most of what I have written is months if not years in the making, carefully edited, worded, developed for posterity. Most are introducing investments that came after hundreds of meetings or posts on the future of cloud, cyber, commerce, manufacturing, you name it. I am ready to A/B test my way out of perfectionism and move past the three bullet point, well crafted rule. So today my third Cliche is I have started blogging again to avoid becoming one. And when I started writing I didn’t have a third point.
I’ll let you know in a year how it ends.
P.S. The most impactful blog posts I have ever written have been fast and unplanned in a moment of creative flow. But I don’t create the time to do it often. I hope I can change.
Predatory Venture Investing: How LPs Can Make it Stop → Pretty sure the reason that AileenLee invited me to that first fateful VC meeting that led to my early role in helping launch All Raise (some of my best friendships for life + later the founding of Angel City)
In the Wake of Fake News, the News Media Needs to Find a New Revenue Model and They Should Look to Music → Made me want to invest in Stem and everything I am learning anew re: NFTs and creator Fintech platforms today. But I started the day just really irritated about fake news.
Should Marissa Mayer Take a Maternity Leave → wrote it in an hour I had free during a regular crazy day at IAC. Still the most read post I have ever written. And for sure the highest ROI on time spent writing.
