Dear SaaStr: How Many Events a Year Should A Startup Founder Attend?

Here are my learnings.

You do need to meet other founders, other execs, your partners, your customers, etc. It really does help over time.

So I’d do the following:

  • First, there are usually 1 or 2 top events in your industry. I’d go every year if you can, either you or your co-founder. E.g., Dreamforce, SHRM, Money2020, ShopTalk, even SaaStr for founders and execs. Someone senior should go every year, mainly because the #1 event in the industry is where the top customers, prospects, partners, and other execs are.
  • If you can, do 1 “getaway” event with other founders each year. One event where a few hundred top founders and execs gather. This is worth it to build relationships and connections. But again, it’s really only worth it if the attendees are truly of high quality. Second tier events are almost never worth it.
  • Go to 2 local evening events a month if you are in a top tech center, e.g. SF, NYC, London, Paris, even Atlanta, Austin, Miami, etc. Go to the best 2 events a month (one every other week) where you can meet other folks. Bail after an hour if you don’t. Otherwise, it’s too much time in front of the computer and with your own team.
  • Do your own annual customer event once you have someone to own it for you. You can start small, even with just a dinner or an afternoon. And do as many customer dinners in various cities as you can.  A bit more on that here.
  • Finally, a niche point, but the top tech industry events attract a lot of VCs. A lot of them. Over 800 SaaS VCs go to SaaStr Annual. I’m sure it’s well over 1,000 to Web Summit and more. Events aren’t per se a perfect way to meet VCs, but the top ones in tech attract a huge swatch of VCs. We have an entire dedicated VC Lounge at SaaStr Annual, and it’s packed all day long.

Got 100 Customers? Believe It Or Not, It’s Time for Your First User Conference

What’s a waste IMHO / IMHE:

  • Skip going to second-tier industry events. While they many be smaller and more intimate, the best people, prospects, partners and customers just don’t go, generally. Which is the main point. One exception may be if you’re a speaker. Speaking isn’t amazing, but I’ve generally found speaking at any event which requires minimal travel is often at least barely worth it.
  • Going to events that aren’t relevant in your industry and/or are too generic. Broad “tech” events usually aren’t worth it, other than for folks that are thinking about becoming founders.
  • Any event with only mediocre and recycled speakers. It’s not that the speakers themselves are so important, they’re in fact really just chrome to attract attendees in many cases. But the best speakers go to the best events, which attract the best attendees, and so on. When in doubt, skip any event with only mediocre speakers. It’s a sign.
  • 99% of “Digital” events. Because you don’t meet anyone. Sometimes the content is good, but just watch it at your leisure.

One last insight: while it’s easier on extroverts to go to events, I think it’s more important for introverts, even if they have a bit harder time meeting people.

Why? Extroverts tend to meet people anyway. For introverts, the top industry events are a great forcing function that get you to meet at least some important people in your industry. Personally, they’re how I’ve met maybe 50% of my top industry contacts over the years.

The Top 10 Events in SaaS. According to ChatGPT.

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