Some notes expanding on my tweets about Boldstart's new fund and fund announcements.
- Build relationships first
- Read between the lines on fund size & thesis
- Look for real stories from other founders
Build Relationships First
You can build relationships with funds before you start a company! Getting to know people makes the process easier later. I was lucky to meet a lot of people early on (mostly on Twitter) and it changed my trajectory. In particular: Hunter Walk, Josh Elman, Ken Norton, John Lilly, and the entire team over at Flybridge Capital.
Knowing people will make it easier to understand what they're looking for and who might be the right fit for you. For me, the two important things are support as a person, asking hard questions, and honestly reflect the good and the bad back.
Twitter isn't the only option to do this. Lots of funds have events, mentorship programs, scout programs, and other ways to get involved. It's easiest to build these relationships if you are in a portfolio company.
Read Between the Lines on Fund Announcements
Cash is interchangeable, but what a fund brings isn't, so you want to focus your effort on funds that can truly help you. Looking at their fund announcements is a good way to do this.
The size of the fund tells you a lot more than you think:
- It tells you approximately how many people will be at the fund (you can't support a staff of 20 on the fees from a small fund!)
- Seeing increasingly larger funds (or steady at a consistent amount) indicates the fund is doing well from the LP perspective. Most investors prove themselves on a smaller fund and then work up to the target size (Boldstart I was only $1M!)
- It's important to figure out the check size. $100M doesn't mean 100 $1M checks. This is usually easy to do from past fundraising announcements, or is common to ask about.
- Roughly, the larger the the fund, the larger the check size. As round sizes have increased, growth stage investors have come down to A, and A firms have specialized more into seed.
- The first check often isn't the only money an investor expects you to get from the fund. Continuing to invest in future rounds (pro rata) helps funds to avoid dilution in the companies that are doing well. When you're further in the process, you can ask the fund how far through deployment they are and what they're planning to reserve.
- The thesis is both for entrepreneurs and for LPs. It gives you an idea of the fund expertise - it can include stage, type of company, or anything else. Make sure the vibe you get from the team matches the thesis.
- Having a fund who specializes in your stage can be very helpful for getting to the next. When getting to know them, dig into how they think about helping companies through the next round. A fund that mostly does Series B likely won't know how to help you at the seed stage.
- Having a fund who works in your area of expertise can also help you build relationships to customers, or get more effective input. It's often an easy way to say "what expertise can this fund bring directly, or through their network?"
Find Real Stories
Build relationships, analyze the fund, but also find real stories from founders who have worked with the fund (especally through bad times).
To the points above, Boldstart is hyper focused on: first check (seed), enterprise, often developer-led. Many investors don't get devtools and aren't patient.
But, the fact that I wrote this about the Boldstart fund announcement shows my pretty obvious bias. Sitting at a fund is the highest compliment I can pay.
A ton of people helped with Dark, but a few things stood out to me from team Boldstart. Here's a couple of the moments that really counted for me:
- Ed and Eliot both used a very early version of Dark (the same experience that engineers described as "being on a horrible interview.") Do I select my investors for programming skill? Absolutely not. Do I want people who are curious and willing to be uncomfortable to try to see it in a deeper way? Yes.
- At one point we were really low on cash in the bank. The first time Shomik and I ever met in person, he came to my office and went through expenses line item by line item. He was honest and said "I can't help, you already cut everything out, but I can tell you that you're keeping your head and that's good."