Fundraising is Unpredictable

I’m often asked to share advice about raising the first few rounds of capital for a young startup.  I’m actually on my way to an accelerator right now where I was asked to lead a few sessions on this topic.

There is a ton out there on the internet about the tactics of raising money.  Paul Graham wrote a really comprehensive essay a few weeks ago that mirrors most of the advice I tend to give.  Read it here.

But my over-arching observation is that fundraising is extremely unpredictable.

This is pretty puzzling to most people.  One would think that fundraising could be a pretty rational process.  Pick the 5-8 firms that seem to be the best fit, get a good introduction, focus on the 2-4 that really dig in, and go from there.

I’ve even seen series A firms give this general advice to their portfolio companies.  “Run a small process” and see what happens.  The thought is you can always talk to more folks later.

From my perspective, this is typically pretty bad advice.  The conversion funnel above is accurate, but only mid-way through your funnel.  The top of the funnel needs to be much larger to have an effective fundraise.

This is because there are so many reasons why VC’s can pass on an investment, and it’s pretty impossible to really account for all the variables prospectively.  Here are some examples:

  • No experience in the space
  • Bad experience in the space
  • Partner had a bad experience in the space
  • No comparable companies have been acquired recently
  • No comparable companies have gone public recently
  • Comparable company had an IPO that tanked
  • Consumer is out of favor
  • Enterprise is out of favor
  • Too capital efficient
  • Too capital intensive
  • Great early traction, but I don’t see how it gets big
  • Big idea, but you should start with something smaller to prove traction
  • Great traction, but engagement is bad
  • Engagement is great, but it doesn’t matter without traction
  • The team is unknown
  • The team is too well known
  • Partner just did a deal
  • Partner is dealing with tons of issues with their portfolio
  • Partner has personal issues
  • Partner is about to join another firm
  • Annual meeting prep is taking too much time
  • Fundraising is taking too much time
  • There is some wierd conflict that is impossible to uncover ahead of time
  • Wife thinks the idea is bad
  • etc etc etc

This is just a subset.  But there are many more.  Maybe when a company is further along, the realistic set of investors is smaller, and a relationship has been built over time that allows for a narrow scope.  But early on, in the seed, Series A, and even the Series B round, I think it behooves founders to assume a 50% factor of unpredictability, and double the number of groups they plan to talk to.  Then as Paul Graham says, run a breadth-first search and parallel process.  Ideally, you’d like to get to a point where you have 6-8 potential leads really digging in mid-way through your funnel.  So get there, you need to have 2X the number of really quality conversations in the beginning, which probably means that you need another 1.5X the number of potential investors before a bunch of firms get disqualified for one reason or another.

There may the concern that your round seems “shopped” and can get stale if everyone knows you’ve been raising money for a while.  This is the reason to do things simultaneously rather than sequentially.  It’s very natural to think “I’ll focus time on my 4 best prospects, then if those don’t look good I’ll move on to my next 4, then so on.  Don’t do this.  You have to parallel process.

I now that sounds like a lot. It is – and you will feel like a maniac during this process.  But if you are honest with yourself about how investors are receiving your story and triage the funnel appropriately, you can accurately and quickly hone it down to the smaller subset of serious prospects pretty quickly.  But it is almost always beneficial to put in the shoe leather to do this because I guarantee that one of those serious prospects will be a group you didn’t expect to be in the mix when you started fundraising.

Rob Go

Thanks for reading! Here’s a quick background on who I am: 1. My name is Rob, I live in Lexington, MA 2. I’m married and have two young daughters. My wife and I met in college at Duke University - Go Blue Devils! 3. We really love our church in Arlington, MA. It’s called Highrock and it’s a wonderful and vibrant community.  Email me if you want to visit! 4. I grew up in the Philippines (ages 0-9) and Hong Kong (ages 9-17). 5. I am a cofounder of NextView Ventures, a seed stage investment firm focused on internet enabled innovation. I try to spend as much time as possible working with entrepreneurs and investing in businesses that are trying to solve important problems for everyday people.   6. The best way to reach me is by email: rob at nextviewventures dot com

    • This is the money line IMO: ” It’s very natural to think “I’ll focus time on my 4 best prospects, then if those don’t look good I’ll move on to my next 4, then so on. Don’t do this. You have to parallel process.” So true.

      • robchogo

        Thanks! It’s amazing how often this happens

        • Yes, I didn’t realize it until you pointed it out. And then all the memories flooded back. What I found hard in helping the founder is that they were determined to do it the other way. I had a hard time convincing them otherwise. Now I will share this post with them.

          • robchogo

            Please do 🙂

    • Anh H.

      This is really great. We were advised to make three tiers of potential investors. Then approach top few prospect from each tiers. Get feedback and recalibrate fit and level of interest. Would you say that this is a good approach?

      • robchogo

        I tend to dislike “staged” processes. It does make sense to have a few different tiers of people to pitch, and then be constantly re-assessing. I think that the main decision is whether to fundraise or not. If the answer is no, shut it down. if the answer is yes, you can tweak your story along the way.

    • iPaulLee

      I think the reality is that fundraising is has become much more unpredictable than in the past, given the significant increase in seed stage companies (and the optionality that presents for potential investors). Very few people today can agree on what early traction is (and even fewer can identify it even when they can agree on it).

      We tell our portfolio companies to meet with 50+ potential investors from the seed stage to run a “full” process around fundraising. Others may argue this is exorbitant but these are the times we live in and several of our companies found a premium term sheet in that 45th potential investor. As my realtor once told me, “all it takes is a market of one”. Keep going.

      • robchogo

        absolutely agree!

      • Anh H.

        I’m in Biotech and our startup have started conversations (and have interest from) with big pharmas. We’re hoping for a “sneak peek” funding arrangement, but have been warned that taking strategic money may make it harder for us to find money in the next round. would you both agree with that?