“Art is to console those who are broken by life.” — Van Gogh
An investor I deeply respect recently told me, I am “really good” at long-form writing. Admittedly, even writing the sentence just before leaves me just as squirmy as when he first said it. I am of course genuinely grateful for the compliment. But my childhood prevents from fully appreciating and accepting a kind compliment.
Rather than having a practiced eye for structure and prose — which I’m sure the real linguists and writers will have much to critique on my lack thereof… for me, I can’t imagine a world where I can boil down distinct and nuanced thoughts from multiple sources in one tweet. Which could mean three things:
I was never great at writing college apps.
I am terrible at Twitter.
I have trouble saying No to people and options.
Don’t get me wrong. There are many things out there are best expressed simply — that need no further elaboration. My blogposts on 99 pieces of unsolicited advice are examples of such. One for investors. One for founders.
Nevertheless, longer form writing helps me think. My mind is often a mess, and sometimes I wonder how I make it by with a mind that looks like the inside of an average college boy’s dorm room. It is most evidenced when I speak, but least explicit when I write. I have time to mull over thoughts. I have time to realize that not every thought, idea, Eureka! moment is a productive one.
I apologize if I seem smarter than I am. I’m not. I’m just another person looking to learn my way through life. Curious enough to know I am lacking, but confident enough knowing I can get there. When confidence in my self-worth wanes, I find solace and therapy in the letters that I ink on a page.
I’ve shared this analogy a few times with friends. That there are artists. And there are designers. The latter fulfills a need their audience has. The latter creates where the audience is someone other than themselves (while that doesn’t have to be mutually exclusive to building for oneself). For the former, the audience is themselves. It is a form of expression unforgiving to the remarks and views of others. While others may appreciate it, you create for yourself. In a way, the best entrepreneurs start as an artist but end up as a designer. For me, this humble piece of virtual real estate is my art gallery. And a small part of me fears becoming a designer through this blog. I save the design work for other parts of my life.
I’ve been fortunate to have sponsors reach out to support this virtual acreage in the wider, increasingly saturated market of content. As you might have noticed, I’ve turned down everyone so far. Partly because of alignment, but mostly, I’m not yet sure if I want to turn writing into a job. To me, writing is comforting. It’s a sanctuary where I can isolate, even briefly, from the equivalent of noisy San Franciscan streets filled with sirens and honks every minute. And upon receiving payment, I would find myself in debt to someone or some entity. That’s fine if it was an essay or a piece of content I wanted to write anyway. But so far, it hasn’t been. And if it’s not, I find myself enjoying this therapeutic process just a little less.
I’m reminded by something Gurwinderwrote a few months ago about the perils of audience capture. In it, he shares the story of Nikocado Avocado, who lost himself to his audience, in a section of that essay he calls: The Man Who Ate Himself. He also shares one line that I find quite profound:
“We often talk of ‘captive audiences,’ regarding the performer as hypnotizing their viewers. But just as often, it’s the viewers hypnotizing the performer. This disease, of which Perry is but one victim of many, is known as audience capture, and it’s essential to understanding influencers in particular and the online ecosystem in general.”
I know many of you came to this blog via the content I write about startups and venture. At least that’s what WordPress tells me. If you came here expecting only that kind of content, I will have to disappoint. And I’m happy to send you recommendations of what I read in that arena. If you came here for that and a little more, I’m excited to share more of my takeaways as I traverse this blue planet. Who knows? Maybe one day beyond.
Nevertheless, I appreciate every one of you for giving me time in your day. Stay tuned!
#unfiltered is a series where I share my raw thoughts and unfiltered commentary about anything and everything. It’s not designed to go down smoothly like the best cup of cappuccino you’ve ever had (although here‘s where I found mine), more like the lonely coffee bean still struggling to find its identity (which also may one day find its way into a more thesis-driven blogpost). Who knows? The possibilities are endless.
Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!
Any views expressed on this blog are mine and mine alone. They are not a representation of values held by On Deck, DECODE, or any other entity I am or have been associated with. They are for informational and entertainment purposes only. None of this is legal, investment, business, or tax advice. Please do your own diligence before investing in startups and consult your own adviser before making any investments.
Over the past 12 months, I’ve done over 100 interviews and fireside chats. While there are the more popular lessons out there, like asking follow-up questions and breaking the ice with your guest with a pre-interview chat or having rapid-fire questions at the end, for the purpose of this blogpost, I’ll be sharing some non-obvious lessons I picked up in the past year.
Never start with a question on career.
Ask your guest three questions before the interview.
Do enough research to be literate in the subject you’re interviewing for.
Prep the audience for questions.
Ask Yes / No questions.
Never start with a question on career.
The first question always sets the stage for the rest of the conversation, especially how vulnerable and candid the guest would be.
The best question in my experience to start with is always a surprise to the guest, as my goal for every interview is to get to know the guest better than they know themselves at that moment in time.
For how you measure success… if that respond with, “How did you know that?”
In practice, it looks a little something like… “I want to start this chat a little off-center. In the process of doing homework for this conversation, I came across the name: Bootstrapping Bill*. Could you share what that name means to you?”
*Footnote: This can be a high school or college nickname or an activity that they were heavily involved in that’s not related to their current career. Or a role model they had when they were younger. Other starter questions can be about quirks they used to have or still have that are:
Not embarrassing
Something that only they have.
For example, for some of my interviewees, I found out:
That someone used to write code on a notepad
A longtime fandom around Gary Keller
A nickname the guest used back in his street dancing days
A class they really enjoyed taking in college and an art professor who inspired her to pursue entrepreneurship
Someone who used to walk by foot 15 hours one-way just to go to a library in Cairo to download PDFs of Stanford research papers to take home and study
Of course eventually it all has to tie back to the topic at hand, which is usually through a trait they developed early on that created the person they are today. Grit. Creativity. Rebelliousness. Kindness. And so on.
Ask your guest three questions before the interview
To piggyback on the above lesson, don’t touch things that are highly personal and risqué, like their social security number or their divorce. The latter without their explicit permission. You never want to be in the situation where you make the guest feel bad. As such, in my email to them a week in advance with the questions I plan to ask, I ask an additional three questions to help give me parameters for the conversation:
What would make this interview the most memorable one you’ve been a guest for even two years from now?
Are there any topics you don’t want to talk about? Or are sick of talking about?
Are there any questions you have yet to be asked, but wish someone were to ask you?
Of course, also share the questions that you plan to ask before the interview. Leave it up to them whether they want to prepare for them or not. And if you do so, they’re likely to bring more robust and less generic answers for your audience. Unfortunately, not always true depending on the individual you invite and how busy they are.
Do enough research to be literate in the subject you’re interviewing for.
Unfortunately, not every A-lister will bring their A-game. Some have been busy. Others are distracted. And a handful of others frankly just don’t care. For them, this is just another talk they’ve done a million times. Not THE talk of the year. Even if it might be for you.
Luckily, it doesn’t happen too often. But it does happen. And as such, you can’t just ask a question. Instead, I like to give the speaker enough time to think of an answer. I call it the QCQ sandwich.
Start with a QUESTION.
Follow up with CONTEXT.
And close with the initial QUESTION.
I’ll give an example.
“Since you just mentioned LP-manager fit / I want to switch gears for a second… I’d be remiss not to ask you about how you think about it. In your experience, how have you seen the best fund managers think about LP construction when they begin fundraising versus when they’re about to close the fund? To shed some extra color, I’ve recently chatted with a number of emerging GPs. And there seems to be a concentration of thought leadership around… [additional context] So, I’m curious, are you seeing the same? Or have my observations departed from the median?”
Most people either only ask the question or lead with context before asking the question (I’m guilty of the latter myself from time to time).
To be fair, you may not need to use this structure all the time. But for people whose answers are typically less structured and may need some time to formulate a robust answer, this is the play. A proxy for this is if their answers only get better the more they talk or if they haven’t had a chance to look through the questions you sent them beforehand, but they typically like to.
Then there’s the exact opposite. Even if the guest speaker is well-intentioned, in efforts to cram as much info into an answer as possible, their talk becomes overly informational. I forget which world-class podcast host once told me this, but he said that that every episode he does is 20% informational and 80% entertainment. The footnote is that the 20% has to be so insightful that it can carry the episode just by itself. The sign of a good episode is if the listener walks away with at least one thing they didn’t know before.
I go back to Kurt Vonnegut‘s #1 rule on writing. Use the time of a total stranger in such a way that he or she will not feel the time was wasted.
As the MC, your goal is to be the steward for insights. The spotlight is never on you, but the question is how do you support your guest in a way that they’re able to put the best foot forward.
Prep the audience for questions
There are two angles I usually tackle from when prepping the audience for questions.
I tell them exactly what they can ask at the beginning and stay away from those topics so that the audience can ask during Q&A if they have no other questions in mind.
Give the audience time to ramp up questions by alternating between live questions and my prepared questions even in open Q&A.
“We’re going to cover a lot of ground today from [topic 1] to [topic 2] to [topic 3]. But if I don’t get to all of them, and you’re still curious about them, please keep us accountable during the open Q&A after.”
And I usually don’t get to all of the above topics, which leaves room for the audience to ask them. Before I ask my “last” question for the interview, I also tell the audience to the effect of: “This is going to be my last question, before I turn it over to everyone present today. So for anyone who would like to ask X something, in about 3 minutes, it’ll be your time to shine.”
The big takeaway is that it always takes a bit of time for the audience to ramp up to ask their questions. And this helps seed some possible topics not covered in the interview so far, so the guest also feels like they’re not repeating themselves.
Since almost every interview and fireside chat I’ve done has been virtual in the past year, this second tactic is designed when you a Zoom chat but I find is still useful when you have a shy live in-person audience. I always tell the audience to leave questions in the Zoom chat at the beginning of the interview. That I’ll call on them when we get to open Q&A. More often than not, the Zoom chat is less alive than I would like. And when it is (and I admit this has only been a more recent discovery of mine), I say:
“We’re going to try something new. During the open Q&A, I’m going to alternate between questions I’ve gotten before this chat to live questions from the audience. So feel free to pop your questions into chat, as I start with the first pre-submitted question.”
I know some MCs seed audience members to ask questions at the beginning of live Q&A for it to not seem awkward. I’ve seen it work, but sometimes I’ve also seen those 1-2 people take control of the Q&A, where the rest of the audience doesn’t feel like they have the opportunity to ask their own question, so they turn passive. With open Q&A, I try to give my audience agency to determine the flow of conversation. Sometimes, they just need an inspirational nudge.
Ask Yes / No questions
For a long time, I had this fear of asking yes/no questions during fireside chats. The main reason was that I believed it would lead to a lackluster interview. The guest would give a one-word response and that we would have radio silence after.
But, contrary to my initial belief, I realized over the past year that yes/no questions are insanely powerful, specifically in the context of public interviews and fireside chats. I do want to note that they don’t hold the same weight in mediums that are known or sought for their brevity. For instance, emails and instant messaging. Where speed is the name of the game.
It’s specifically under the circumstance where there’s an allotted time and an expectation to fill the void with content that this tactic shines. The guest would more often than not feel an urge to fill the empty void with additional thoughts and context. In that moment, sometimes they share something that is more off-the-record than they initially planned. Of course, in realizing that it is, and since most of my fireside chats are recorded, I follow up with the guest after to make sure they’re okay with the recording.
As an interviewer, at the same time, I’ve learned to hold myself back. There’s an equal if not more powerful urge in me to fill the void with questions. After all, oftentimes, this is the audience in which I had invited, and feel my reputation is on the line. If you could see below the camera, I have a sheet of paper in front of me where I write “Shut up” to myself at least twice before I jump in.
In closing
While I share all the above, just like being a founder, you could do everything right and the interview may still fall short of being ideal. And when some interviews do fall on either deaf ears or I feel I was just unable to bring out the best in people, like many others, I wonder… do I just suck at being at asking questions? Or being an MC?
It’s an iterative process. And the fun part of it all is that it makes me a better investor. I ask founders better questions. The answers I get when diligencing are more valuable.
The above isn’t the end-all-be-all. I’ve written on this topic before, and I will continue to work to be a better interviewer. But hopefully the above serves to bolster your arsenal of tactics.
Edit: Added in a fifth lesson that’s too short for a full blogpost, but longer than a tweet.
Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!
Any views expressed on this blog are mine and mine alone. They are not a representation of values held by On Deck, DECODE, or any other entity I am or have been associated with. They are for informational and entertainment purposes only. None of this is legal, investment, business, or tax advice. Please do your own diligence before investing in startups and consult your own adviser before making any investments.
The past 2 weeks brought me a whirlwind of conversations with emerging managers and LPs, catalyzed by the emerging LP playbook. And of the former, I’ve come across two main themes:
Everyone — I kid you not… everyone — has top-tier VCs as their follow-on and/or their co-investors. What was once upon unique is no longer so.
Eric was right. There’s an overabundance of the word “signal” in venture wonderland these days — to the point the word itself has lost its meaning. By definition, it should mean that is unique and stands above a sea of noise. For many investors, that means either investing in brand-name startups (i.e. SpaceX, Figma, etc.) or investing alongside brand-name investors. The latter, unfortunately, is also a product of the ecosystem as many LPs seek social proof about your investment thesis from others’ who have a proven track record. The former gets a bit sticky. A lot of these logos are either off-fund-thesis or came as a Series B syndicate investment (but the fund itself is investing in pre-seed or seed).
After publishing the emerging LP playbook last week, I've been lucky to chat with quite a few emerging managers raising their Fund I's
And there are 2 common themes I see in their decks:
1. Tier 1 VCs as follow on investors are table stakes 2. There's a lot of logo shopping
To piggyback on the above, the notion of signal is worth elaborating on, likely a vestigial appendage of the past two years.
Let me preface by saying that it takes a lot to get to conviction.
In 2020 and 2021, many investors’ calculus of startup signal boiled down to three things: great investors, great traction, and great team. And in that order. That is first and foremost what I see a lot of professionalizing investors do. I can’t entirely blame them since the ecosystem itself propagates the belief that if a Tier 1 VC jumps in, you’re more likely to get to a great exit. Or at the minimum, get a great mark-up to make your IRRs and TVPIs look better. On paper, of course.
But what I believe a lot of investors are missing is that… venture is a game that’s not about your batting average, but about the magnitude of the home runs you hit. You’ve heard it before, and you’ll continue to hear more of it. Unlike other financial services, VC is driven by the power law. 80% of your returns will be driven by 20% of your bets. That’s the 10,000 foot view. Let’s be honest. Most of us, myself included, don’t take that panoramic view every day or even every week. In fact, I see many emerging managers only take that view when they’re forced to. In other words, when they’re in fundraising mode.
For many professionalizing angels and syndicate leads, that becomes trying to string a narrative from seemingly disparate data points. Or at least, it seems that way.
As Asher Siddiqui told me, “[after] you look at their whole life and career history, and look at their thesis, if the thesis doesn’t make complete and perfect sense, then I don’t think this is a ‘great‘ fund manager. If it fits like a glove, then yes, they could be.”
The best GPs are disciplined even before they start fundraising. They focus on the thesis they want to raise on when they do. That’s not to say they don’t invest off-thesis every so often. But they don’t pitch their off-thesis angel or syndicate investments as part of their thesis-driven track record. But I digress.
In chasing signal for the sake of signal, when you hear of a hot deal every other day, many investors forget to be that belief capital for founders. I’m not saying that an investor should do so for every founder out there. But to pick a few, or even just one. One that they’re willing to take the swing before others do.
The signal is their own conviction in the founder.
The first half
Because of this progression, there’s been a new two-part question I really enjoy asking emerging GPs. The first half:
Which company in your portfolio you think is still underestimated?
Which company in your portfolio didn’t get the investor attention you expected but are still extremely bullish on their growth? And why do you still believe in them? What are other investors missing out on?
It’s not about track record or social proof here. It’s about the ability to recognize exceptional talent and articulate it clearly. Hopefully, a rose growing in concrete.
Well, in terms of the odds, you’re likely to be wrong. But that’s okay. You need to be willing to be wrong to achieve outlier success.
Fund I is often the proof-of-concept fund for the emerging managers I’ve talked to. They start by writing small checks, don’t lead rounds, and don’t fight for ownership targets. They claim to be extremely helpful and hands on. Then again, expectation often differs from reality, especially if they’ve never been so before (where LPs discover through reference checks). And because they’re writing smaller checks now, I’ve seen many implicitly hold off on developing a framework to get to conviction until Fund III. Whereas the best GPs start thinking about it early on.
You can think about it this way. As long as you’re benchmarking on signal via other investors, why should an LP back your thesis when they can back your “signal”?
For individuals and smaller family offices, they’ll still back you. What they’re buying is access, since they can’t afford nor have the relationship to be an LP in the “signals.” Larger LPs have the optionality to do so. And if you’re an emerging GP hoping to grow as a professional manager by having larger and larger funds, you eventually need to raise from large LPs. At least, until the SEC changes their 99 limit. And to do so, from larger LPs, means you need to bet where their existing portfolio has not bet before. Plus do it well.
The second half
If you haven’t already, a great way to build a referenceable track record is to sweat the details. Yes. The details matter. Nate Silver, one of the best poker players of our generation, said earlier this year, “you can’t just get the big things right in poker. You have to get the small things right too. It’s too competitive of a field right now.”
Though he said venture is different, I believe he’s half right. Most investors don’t sweat the small things. But investors should. Today, that’s how you stand out.
It might not have been true a decade ago, but now it is. Just last year, in 2021, there were 730 funds created. To put that number into perspective, on average, that literally means two firms closed every single day last year, including the holidays and weekends!
Capital has become a commodity. In 2021, speed was a differentiator. Clearly, in 2022, it is not. Today, it’s tough being a founder. If you’ve raised in the last two years, you’re considering extending your runway. That means having tough conversations to reduce your workforce, your benefits, or your salaries. If you haven’t raised, it’s a hard market to be raising in now. And so the differentiator today, is in two parts:
Helping founders navigate these tough situations. In other words, being (proactively) helpful.
And helping founders raise their next round. Mac Conwell recently shared a great thread on how powerful a founders’ network is to get funding. The same applies to an investors’ ability to help their portfolio raise capital. How liquid is your network? It’s not about who you know, but how well you know your friends downstream, and how can you get them over the activation energy to invest. Don’t get me wrong. There still needs to be a certain level of hustle from the founders themselves. But a great investor often steps in to reduce as much friction as we can in that process.
Both of which have long been the job description of being a VC. It’s in the small things. Jump on a 2AM call. Help your founders figure out the wording for a reduction-in-force. Fix the sales copy to better close leads.
There are 10-15 character-building moments in a founder’s journey where the moat they build around the business (as opposed to just the product) is not IP or early product traction, but rather from the lessons obtained from scar tissue.
It’s hard to predict looking through the windshield when these moments are, but quite obvious via the rearview mirror. And the best an investor can do is be there as much as he/she can. Albeit hard to do for every company in your portfolio, and that’s the truth. The wealth of information creates a poverty of attention. The larger your portfolio, the harder it is to be truly helpful to every single one. So focus on founders who need you, rather than those who will do great without you. Reputation is built in wartime and realized in peacetime.
So, the second part to the above question is:
What did you do for this company that no other investor or advisor did?
… where I’m looking for answers on how this investor went above the call of duty to help a company they believed in grow.
In closing
In summary,
Which company in your portfolio you think is still underestimated?
What did you do for this company that no other investor or advisor did?
This is by no means original, but heavily inspired by the recent conversations I’ve had, as well as helps me build my own framework for analysis. In parts, this question is a derivation to the check size to helpfulness ratio (CS:H). How helpful are you as an investor? When you say you’re founder-friendly, do you mean it?
Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!
Any views expressed on this blog are mine and mine alone. They are not a representation of values held by On Deck, DECODE, or any other entity I am or have been associated with. They are for informational and entertainment purposes only. None of this is legal, investment, business, or tax advice. Please do your own diligence before investing in startups and consult your own adviser before making any investments.
I’m sure every founder has heard that line at least 50 times every time they’re in fundraising mode. Hell, even outside of it. Pshhh, I’m guilty of saying it myself, while I do try to catch myself when I do. You’d think being helpful is table stakes as an early-stage investor. Surprisingly, being helpful as an investor is actually a huge differentiator.
Most investors are only as helpful as their check size, despite pitching their value-adds a million and one times. Some investors are extremely helpful only within the funding window(s) they are participating in. For instance, a seed investor is largely helpful during the 12-18-month funding window between the seed and the Series A. Others are helpful when they are asked. And a small handful of investors are true champions by being proactively helpful.
One of my favorite stories when I was interviewing LPs for the emerging LP playbook was when Brent invested in a GP who had a track record for being proactively helpful. This GP “was one of [Brent’s] first investors. He would often come into our office, and without being prompted, proceed to write code against our APIs.” Unprompted. Unsolicited, but insanely helpful.
Earlier this week, I was also reading the October investor update from a founder I love, and in it, he was talking about how much he loved the team at Sequoia (who have yet to invest), and shared that he had learned more about product in the last “3 days than [he had] in the last 3 months.”
A big part of the reason I joined the On Deck Angels team last year was to be a part of a community bringing the world’s most helpful investors together. As such, I’ve been lucky enough to be a student to our community on how they’re helpful — whether they choose to invest or not. Some examples include:
Writing a 3-5 page bug report for every founder you take a meeting with. This teaches an investor two things: 1/ to be judicious of one’s time and only take meetings with founders that you are truly likely to invest in, since these take a while to research and write up, and 2/ to always think in a “give first” mentality.
Record a Loom breakdown of why you decided to pass and what would get you over the fence. I’ve shared this before, but one of my favorite VC quotes and has been since the day I learned of it is: “There is no greater compliment, as a VC, than when a founder you passed on — still sends you deal-flow and introductions.”
Being able to admit how you can’t be helpful. As an investor, you don’t have to be good at everything, just really, really good at one thing, or a small handful of things.
Sharing their memos publicly on why they’re excited about a startup. This helps build a startup’s reputation, and also your own brand as a thought leader.
Sharing your deal memos and founder asks with your LPs (if you run a fund or syndicate). For this, admittedly, it’s best to get the founders’ approval, given the confidential nature of certain details.
Make an intro for every pitch meeting you take. Intros are often extremely high leverage. It takes you 1-2 minutes to write something up and send a double-opt-in intro. And oftentimes, can save the founders from at least tens of thousands of dollars worth of decision-making mistakes or costs. Of course, that requires you to have either photographic memory (which I don’t have) or a really good CRM. For the latter I use Airtable, and I track small details like: ideal catch-up frequency, preferred medium of communication, chill factor (yes, some of my intro emails can get a bit wonky depending on the person), and what makes them the best dollar on a founder’s cap table.
Many of the above aren’t necessarily hard to do, but just requires a consistent commitment to do them well. And of all the many ways one can help, they all fall into three buckets:
Introductions
Strategy, decision-making, and tactical advice
Downstream and co-investment capital
The last is the most obvious. The second is easy to understand, but often the hardest to execute on, and often comes from being an active or former operator yourself. Hunter Walk of Homebrew has this line, “Never follow your investor’s advice and you might fail. Always follow your investor’s advice and you’ll definitely fail.” Advice is just as helpful as it is dangerous. Something I’ll likely dive into in a future blogpost.
But for the purpose of this one, I’ll focus on introductions.
Network liquidity
I was recently reading Shawn’s chronicled reflections from his time as a Partner at On Deck — someone I am deeply fortunate to have worked alongside. In it, one line immediately grabbed my attention:
“Network liquidity is table stakes. […] This refers to how successful we are at connecting founders to people that are relevant to their needs and asks. The most important dimensions to consider are accuracy (how relevant was an introduction) and speed (how fast did you deliver).”
In 2022, and I imagine even more so, in the next few decades, it’s not about who you know — ’cause frankly, everyone will know everyone else. Social media, the metaverse, web3, the Zoom-ification of everything, and the rush back to IRL will only make this easier. I don’t believe any investor — or in fact, anyone, period — will have a “proprietary network.” So instead of who you know, it’s about how well you know them, and your ability to leverage that relationship.
We see this especially in the venture markets. In my recent blogpost, Sapphire’s Beezer shared: “We have felt for a number of years now (including pre-COVID) that the concept of ‘proprietary deal flow’ is not really a thing. Proprietary access however is something we think is true, powerful and not simple to achieve (hence why powerful ).”
I wrote quite a relevant essay a few months ago about how to write email forwardables. In order to tap into someone else’s network liquidity, there are two things you must establish:
Your rapport with the person you’re asking it from
Their rapport with the person you want to get to know
Requester and matchmaker rapport
I can’t speak for everyone, but my willingness to make intros depends strongly on both of the above, especially the former. Selfishly speaking, even if I don’t know the person who will receive the intro nearly as well, to put it bluntly, if I know I can look good to that person when I make it, that’s a strong motivator to do so. For that to happen, I need to fall in love with something about you — the person who would like to be introed. It could be you (usually the greatest motivating factor) and your passion. Even better if your passion is contagious. It could be your product. Or your insight. Usually, it’s some permutation of the afore-mentioned.
I meet with 10-15 net new founders per week. 25-30, if it’s accelerator season. Given my job description, almost every single founder asks me for intros. Sometimes, even without context.
Matchmaker and intro recipient rapport
The other side of the equation is the rapport I have with the person you want to get to know. The truth is the world of intros is like any other asymmetric game. The most well-known, busiest, and often hardest-to-reach people are the ones bombarded with the most intro requests. But like any other human being on this planet, they only have 24 hours in a day.
As a matchmaker myself, I have to cognizant not to overwhelm incredibly busy individuals with a flood of intro requests. And it is my job to triage requests. Sometimes, it’s also helping, in the case of fundraising, founders recognize not what they say they want, but to help them figure out what they really need.
In making requests to famous friends
There are times when the busiest people I know are the only people are capable of fulfilling the ask. So, it also comes down to your accumulation of social capital with the intro recipient. I have two columns in my Airtable CRM, labelled:
Why I am useful to them
Is my usefulness a priority to them? (on a scale of 1-5)
With the former, have I given before I have taken? Have I helped them before? Additionally, is the intro request more of a give or a take? A great startup with a strong team and traction for an investor is more of a ‘give.’ It’s deal flow from them. On the flip side, a founder asking for free advice is more of a ‘take.’ In general, ‘takes’ require more social capital than ‘gives.’
With the latter, priorities change. You may be useful in one phase in their life, but no longer so, in another. For example, when an emerging manager is fundraising for their Fund I, I am someone who is extremely top of mind for them, but when they’re not, I slip in importance. But regardless of the phase in their life, if someone is kind and thoughtful AND you’ve helped with a major decision or inflection point in their life, they’ll always be around. That said, I never try to abuse that goodwill. Personally, I hate being in debt and having others be in my debt.
You can also be “useful” in many different ways. For instance, doing interesting things is one way. One of the most famous people I know with millions of followers across his socials is willing to entertain any ask I ask of him under the condition I invite him to every social experiment I host in LA.
In closing
The more relevant an ‘ask’ is to the recipient, the more likely they’ll respond positively. The more top of mind you are and the more social capital you have with someone, the faster they’re likely to respond. We live in a saturated market of attention. Everything in the world is asking for ours — social media, kids, friends, work, portfolio companies, chores, Netflix, and sleep. And by no means all encompassing.
As you scale yourself as an investor, it’s important to think critically about who is in your network and how well you know them. If you’re a syndicate lead with 500 LPs, how many of them are passive capital? How many of them want to actively help your portfolio?
If you’re an investor who’s a Xoogler and wants to leverage the Google network, who do you know will go out of their way to help you? How many of them have you on speed dial? Which vintage were you a part of?
The great Richard Feynman once said, “You must not fool yourself, and you are the easiest person to fool.” One of the greatest fallacies an investor or even a founder can make is to assume they have a larger leverageable network than they actually do. Only to realize that when you do need to draw on these connections, you’re unable to.
So, if you have the time this weekend or the next, sit down with a critical eye and ask yourself: How liquid is your network?
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Any views expressed on this blog are mine and mine alone. They are not a representation of values held by On Deck, DECODE, or any other entity I am or have been associated with. They are for informational and entertainment purposes only. None of this is legal, investment, business, or tax advice. Please do your own diligence before investing in startups and consult your own adviser before making any investments.
