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Which customer segment to target?

I'm working on formulating a plan around a vague idea @danielbachhuber and I have - basically, a better Meetup. There are two customer segments:

  1. Free users who join groups (and could eventually create their own groups)
  2. Paid users who will organize groups

Adoption seems like a bit of a chicken-and-egg situation - the free users will only be incentivized to join if there are groups they can join, but the paid users will only want to pay for a group if there are people who will join the group.

So who do we target marketing toward? My intuition says that you can't target both to start. Marketing is hard enough as it is with a really targeted audience, so trying to market to multiple audiences just seems like a bad idea.

Any advice from people who have been in this situation - where all users aren't necessarily your paying customers? Any ideas on how to go about this?

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    We are in a similar boat - building a marketplace to connect authors with book reviewers. Authors are like your group organizers (they pay to get access to reviewers) and book reviewers are like your group members (they get books to review).

    We went after the reviewers first and seeded our site with ~500 reviewers. To minimize friction, we created their profiles ourselves and sent them an email asking them if we can list them. Most said yes - they have nothing to lose and the opportunity to get free books (or access to relevant groups in your case) with zero effort.

    After curating a catalog of reviewers, we had a more compelling product to present to authors. Now we are spending 70-30 effort on getting authors to pay us while slowly growing the catalog.

    So, my advice would be to get some users who are eager to join groups. Seed your site with them. You may need to focus on a specific type of group and geolocation so you can focus your marketing (think eBay and how they started off focusing on bring buyers and seller of just one product: pez dispensers).

    After you get some users there, switch gears to finding people who are eager to mobilize people and organize meetups. Maybe you will find the latter automatically in the first phase!

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      Thank you so much fo your reply @dhruvg, that makes a lot of sense!