When Your Side Project Blows Up with Dawson Whitfield of Logojoy

Episode #038

What would you do if your side project made $30,000 in its first month? This is the exact situation that Dawson Whitfield found himself in after a long history of launching projects that didn't make it very far. The conventional wisdom is that it takes years to build a successful business, but in this episode we discuss why that wasn't the case with Dawson's business Logojoy.

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    On first glance at the headline, I really expected this article to be about a hardware side project which went badly wrong (with explosive consequences)...

    The real episode was almost as interesting though ;)

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      I believe you'd be looking for www.indiecrackers.com to read such stories.

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        You know... I actually clicked on that link. Thanks for raising my hopes and dashing it to pieces.

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          Sorry! :/

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            HEHE. S'all good.

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    My Main Takeaways:

    • Jesse started WorkFlowy just as a project to help him learn to code.

    • Jesse eventually quit his job because he didn't believe in the company anymore, and took the opportunity to work full time on WorkFlowy

    • Jesse got a technical co-founder, because he learned the importance of finding one from other entrepreneurs (Paul Graham, Naval Ravikant).

    • Jesse says that he is not a marketer and doesn't do marketing, although he would like to (He says this is a character defect of his). He says that if he didn't go through Y Combinator he would have had 3 users by now. But since he went through Y Combinator, he naturally got a lot of press coverage, and had 10,000 on day 1.

    • Jesse didn't want to get funding because he didn't want to give up control of his business, and have to obey shareholders.

    • In the early days, Jesse was low on cash since he didn't choose to get funding. So he spent all his money on rent, and eventually his girlfriend at the time started paying rent. Until people started paying for Workflowy.

    • When you're working with someone in a partnership, have a weekly structured conversation to bring up any issues, so that they can be resolved. Address the small issues before they become big issues.

    • At the time of this interview, Jesse said that Workflowy was getting about 20,000 new signups per month, but only about 1,000 of those users stayed long-term.

    • Watch people using your product.

    • Jesse says that his entrepreneurial story is: doing lots of things that he thinks are bad ideas, and it working out.

    • Jesse and his team focus on the things that provide the core value to their users.