Being CEO and founder of a venture-backed start-up is hard. A CEO, especially at the start, is head of: product, sales, recruiting, strategy, and everything else the company has to do to succeed. However, there is one job that’s not an explicit function that is always and forever the number one job of any startup CEO – not running out of money. 

There are lots of ways to ensure this doesn’t happen – have a great sales engine, build a high-margin product, find scalable low-cac acquisition channels. But at the end of the day, for any venture backed high growth company you have to fundraise. 

The best venture-backed founders are almost always exceptional at fundraising. For some, this skill is innate – and for a while in 2020-2021, everyone appeared as though they were exceptional. But the reality is that like any other skill, the founders I know who are exceptional at it obsess over it and become true students of the game.  

I knew almost nothing about being a great fundraiser when I started my company, but was lucky to have a co-founder in @john Kobs who was obsessed (in a good way) with being a world-class fundraiser and luckily I got to tag along for the ride. 

Here is what I learned great fundraising CEOs have in common:

  1. They obsess over their story. They are constantly refining the story to themselves and constantly pitching it externally to other friendly investors, other founders, and slightly uncomfortable strangers.
  2. They relentlessly build their network. Especially in today’s fundraising environment, you might need 30, 40, 50, or even 100 meetings to find your lead. The best fundraisers know this is a numbers game and ensure that they have as many shots on goal as possible.
  3. They run a process that is tighter and better organized than anyone else. This has two components: 1) your meeting cadence with investors, and 2) how well your materials are organized. Fundraising is about momentum and timing. The best founders have everyone scheduled in tight succession and then show up with a deck and data room that knocks their socks off.

Doing this well takes work. Lots of work. So, where should you start?

  1. Talk to other founders constantly about their raise. Especially founders that are at a later stage than you. They’ve got the best tips and tricks to do this well.
  2. Take and proactively make meetings that might not seem timely. Yes, there is lots of conflicting advice on “only meet with VCs when raising, because VCs will waste your time.” This absolutely can be true, but you can control this. Don’t let yourself get sucked into a process if you aren’t ready.
  3. Always have a WIP version of your next round deck. Revisit it constantly.
  4. Carve out an hour a week or more specifically on your schedule to invest in fundraising. Send investor outreach, update your crm, pitch a fellow founder. Do it every week.

And once you decide to raise, set realistic expectations of what it will take to raise a great round.

  1. Pre-work (story, deck, data room, schedule of meetings) – this will vary depending on what round you are raising (bigger rounds usually take more prep work because there is more to prep). But between all of the above, expect to spend 100 hours over 8 to 10 weeks getting ready. Great decks take 40+ hours, same with great models and data rooms. You can’t fake this.
  2. During-work – expect to meet with 50+ firms over three to four months.  This will be exhausting, but doing the pre-work well makes the meetings higher yield and the time outside the meetings lower.
  3. Post-work – yes, you will still need to invest time post TS in finding additional investors, addressing doc issues and getting everything across the line.

Yes, there are companies that get preempted and fundraises that take two or three meetings, but as a founder I would not want to bet my company that I will be one of those rare cases. I would rather do the hard work upfront and obsess over being a world-class fundraiser, rather than leave it to chance.