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Joined 11 months ago
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Cake day: November 9th, 2023

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  • Oh boy - do you have funding? And some way to attract at least one side of the market - is there something valuable they can get from your platform without needing the other side of the market?

    If you don’t have both of these things, honestly, I think you’re going to struggle.

    I don’t mean to be a downer, but building a two-sided marketplace is incredibly difficult even with funding, and you’re going to need a LOT of money to get to a stage where you have a critical mass of users on both sides.

    And I’ve never seen a bootstrapped two sided marketplace ever be successful apart from PlentyOfFish - but dating is a weird niche and the normal rules of business don’t apply there.


  • A word of advice - don’t bother going through recruiters when applying for jobs. Recruiters are looking for someone who has done the exact same job for a very similar company before. What they’re NOT looking for is a square peg in a round hole - if you took time out of your career to start a company, you’re going to look odd to them, and they’ll move you to the “too hard/don’t bother contacting pile” immediately.

    Instead, reach out to the CEO of the company you’re applying to directly. Tell them you spent the last 4 years building your own startup and made some progress, but ultimately the company didn’t take off. Ah well, you miss 100% of the shots you don’t take, right? (Use that line)

    And now you’re done with startups and have decided you can have more impact by joining an already successful business and making it grow faster rather than trying to start your own from scratch.

    The big fear that a potential employer is going to have is that you’ll be difficult to manage and eventually leave again to do your own thing. Which is, honestly, totally fair.

    So you want to address that fear head on, and tell them that you’ll commit to a reasonable timeframe (2 years, for example).

    Honesty is the best policy IMO, but you can still spin the story in a way that allayws their fears, overcomes their objections, and makes you look like a massive potential asset to their team rather than a high risk misfit.