It's definitely difficult, I started a remote work site before covid but it didn't take off. Couldn't solve the 'chicken-or-egg' marketplace problem, I couldn't get enough companies to post jobs and people found an empty site apalling.
Posting in case people haven’t come across this advice: the trick to a two sided market startup is usually to find a way to provide value to one side without the other side being present.
So, for example, you build a free platform that helps remote contractors manage their hours, billing, invoices, leads etc.
Then, once you’ve built up an audience of contractors you say to the companies “hey, I have a million people working on here, I think they’d be interested in job opportunities, so I’ve made an opt in jobs board / newsletter” and go from there.
Of course, it might not succeed, but AFAICT this is the general strategy for solving this problem.
This is great advice, but you also have to be really strategic about this as the solution you create to try to acquire one side of the market can easily become a full-time burden that distracts from what you really want to offer.
Using your example, the market for time tracking, invoicing, etc. is very mature and highly competitive, so if you launched a solution in this space, you'd have a steep uphill battle to gain traction.
Making something free doesn't automatically guarantee it will be competitive or appealing, especially in mature markets where the entrenched competitions' offerings are hard for upstarts to come close to parity with. Sometimes "free" makes a product less appealing.
In the example market, there are already established players with free tiers.
Yeah this, people come for the utility, and community then arises naturally. Unfortunately it's very hard to lure users from the big platforms with community only.
