3 Irritating Things That Angels and VCs Do in The First Meeting and Conversation

Images via Bossfight

In the last month I’ve been making the rounds with angels and venture capital institutions and so far it’s been pretty amazing. People are, for the most part, instructive, resourceful, and full of pointed feedback.

In addition, as I’ve shared already, conversations can move really fast and angels and VC’s know that response times can be a powerful signal of respect for the entrepreneur’s time and the opportunity that could pass them by. Like most things, this goes both ways and so I try to respond as quickly as I can to respect their extremely limited time as well.

And the vast majority know how to date really well as they know that they are beginning to build what could eventually become a very powerful and exciting and long-lasting relationship. The first-time meetings and introductions are generally cordial, friendly, and hopeful.

But not all of them have been great and here are a few things that I’ve observed that could serve to help other angels and VCs as they interface with entrepreneurs. Think of this as some constructive criticism that I hope can be consumed without offense.


We’ve all got a lot to improve, me most of all.

Everyone’s got quirks that make them unique and special, so what I’ve done is tried to identify patterns of behavior over 40 or 50 conversations that I’ve had in the last few months that are, essentially, disrespectful or just in bad taste and that aren’t related to any individual idiosyncrasies.

Heck, I have a few of my own strange behaviors that, without context or without knowing me well, could quickly offend, so I’m sensitive to these types of things! But here are a few things that I’ve jotted down in my tattered notebook that I think could be useful reminders:


1. Stuck in High School

This angel or VC spends a lot (most) of their time referencing their past successful exploits as a justification for every single piece of advice or perspective that they dispense. In other words, this person cannot seem to move beyond their previous life and banks on it 100% of the time.

This is easily identifiable when the individual continually and repetitively prefaces everything that they are about to say with something about their previous success(es) and how that success justifies whatever is about to spill out of their mouth. For instance:

So, yeah, when I sold my last company for $1.2B we did the same thing…

or…

Remember, we were one of the first investors in __________ (insert Unicorn company here), so, this is why that won’t actually work…

or…

I’m not sure if you know, but, I was employee #2 at __________ (insert Blue Chip, public company here), and I designed that program, and killed _________ (insert other competing company here) and so, yeah…

This irks me a bit for a few reasons and mostly because it’s so obviously prideful (and sometimes it can come off as a bit arrogant). Yes, I, as a fellow entrepreneur, know of your amazing exploits (Hell, I did my homework…) and I respect you greatly for it, I really do (that’s why I wanted to chat with you in the first place…)!

But no one likes to be patronized and no one wants to hear about your amazing multi-figure exit every single time you have something to say, especially if it was 10 or *gasp* even 20 years ago. The times are different now, the businesses that we build are fundamentally different thanks to the technology and the affordability of a startup, and your past experience may not actually apply to the context of what is being built today.

It just seems that some of these angels and VCs are living too much in the past and relishing too much their old achievements. It’s like the High School Varsity football player reliving their State Title win, over, and over, and over again. I get it, you were awesome, congrats… cool story bro.


2. Zero Fucks Given

No one in our industry likes to waste time, especially here in Silicon Valley. Most people fundamentally understand that time is our greatest and most valuable and limited asset — wasting it isn’t something that is taken lightly.

But on occasion I’ve met with a few who clearly have no interest in investing and who are filling holes in their schedule, for whatever reason. Trying to be respectful, I end up entertaining the person for 30 minutes instead of building a relationship. I leave these meetings feeling really discouraged.

A few clear signs that they could give less of a shit about our conversation and, more importantly, a potential relationship:

  1. They haven’t read the deck, or the short blurb, or anything. They have done zero research or done any cursory background diligence. In fact, they may even have trouble remembering who first made the introduction. I’ve had a few literally start the conversation with this: “So, wait… who are you?
  2. They are more concerned with who I’ve talked to and who else is interested in the deal or opportunity than me, my co-founders and the product that I’m building. When they start asking questions like this (and can’t seem to stop asking about this) I know that we’re headed for a dead-end: “So, what did so-and-so think about the deal?
  3. They exhibit a lot of the “High School State Champion” mentality and spend more time talking about war stories than building a dialogue between two people. Storytelling mode spins up and then dominates the conversation. Exit a dialogue, enter a monologue.
  4. They are easily distracted by their phone or their watch or by someone that they know who just entered the cafe and will eagerly enter into a conversation and burn 5–10 minutes “quickly” catching up with a total drive-by instead of our very limited time together.

As I’ve mentioned, these are easily the most discouraging meetings that I have because I spend my time trying to creatively humor the person while thinking about all the other things that I’m not doing that could be more worth my while.

They may even end the chat by asking me to send the deck to them so that they can “follow up” after they review it when I have, in fact, already sent it to them before our chat.

Ugh, total burn.


3. A (Slight…?) Genius Complex

The challenge (and wonderful opportunity!) of living and working in Silicon Valley is that you are surrounded by the very best and the very brightest people alive who have experience in the very industries that you’re trying to work and build products / solutions for. These people are, legitimately, at the very top of their class.

But in a world where everyone is world class, things like humility become not only instructive but, I believe, a competitive advantage. When I meet with people who are genuinely grateful for the opportunities and affordances that they’ve had and are willing to share those experiences with others who are looking for help, I immediately want to work with them.

(Oh, and it’s true, mean people fail.)

But there have been a few who, for whatever reason, think most highly about their own accomplishments and who apparently have an answer for everything — it’s as if their own experience becomes the rubric for how all products and companies should be built and they generously apply this logical fallacy throughout the entire conversation.

They, through their infinite wisdom, know exactly why X, Y, and Z will fail and how I and my team should be doing things different — no, better, and how if I were to only do it their way then it would obviously be a success and how only then they would invest or send capital support our way.

They have a negative response for everything that is shared and have long-winded answers or short, curt retorts that stop a conversation or even a nice repartee from ever occurring.

I get the sense that these folks are looking for personal disciples rather than investment opportunities and I gladly pass. You see, I’m not looking to build version 2.0 of your old company… I’m looking to build my own and I would have loved your help to do it.

Most are blind to their own approach but a few actually have enough self-awareness to return and apologize for how they handled things:

This convo was actually really good, btw. Super-helpful.

They have every reason to be right and their proven track record gives them credence and they are worthy of a ton of respect — but there’s no reason to be an ass about it.

And, you know, sometimes it’s the delivery that matters more than the content in a relationship, you know what I’m saying?


I’m taking notes, all the time.

Now, to be sure, these examples are few and far between and the vast majority of my conversations have been awesome. And, I don’t get that upset since I do not expect every conversation to lead to a long-term relationship or to go swimmingly well. We’re all perfectly-imperfect, as they say, and we bring all of our garbage to the table when we meet new people.

And I get it (and I’ve done this before) — the relationship between an entrepreneur and an investor is, for the most part, transactional, and if you manage to make great friends along the way then that’s a huge cherry on top. My hope is to build those long-term bridges but that’s not what I’m necessarily trying to do on the outset. I’m looking for capital and they are looking for a really good return on their investment.

Finally, as I re-read the draft of this post I am forced to be introspective as I want to be able to take my own medicine and not just dish it out. We all have a ton to learn and an infinite amount of opportunity to improve. I want to acknowledge to my own issues while I identify them in others.

You see, I want to be the type of entrepreneur who stays open to new experiences and doesn’t always bank on my previous accomplishments as rational for future success.

I want to make sure that I do my research and be fully prepared and knowledgeable of the investors that I’m sitting down with so that I can fully maximize their time and make sure they feel respected and appreciated.

And, I want to ensure that I stay humble (and hungry) because there is always more to learn and to glean from those who have been incredibly successful (and lucky).

Most importantly, I want to remain grateful for the opportunities that I’ve had and the favor that I’ve been given to meet with these folks and to not take their time for granted.

They, like me, have only a few slots open every day and every single time they say “Yes” to meeting me they say “No” to another entrepreneur (and potentially a better investment).

I don’t take that lightly — I’m so thankful.

One more, just to end the post nicely.

At TOMO we’re building a new way of doing work and looking to automate some extremely unsexy-yet-time-consuming processes. This is our journey from idea and concept to product and company. Follow us on Twitter or and subscribe to our email newsletter for important updates!