How to get hired at a startup when you don't know anyone

Great story, and I love the author's initiative.

The author overlooked the first major factor in their success - finding the startup they wanted to work at! I actually think the more specific you get in your job search the more successful you will be. People often think that by being 'flexible' in what they want to do they are increasing the number of companies they can work for. That is true, but you aren't trying to work for a bunch of companies, you are trying to work for one. By being that general you will never find the place where you specifically are the best candidate.

To be concrete, I'd rather find the 5 companies that are really aligned with my skillset and target them very specifically than apply to 50 random companies looking for someone kinda sorta like me.

At my previous company, someone walked into our office and asked if we had any openings for engineers. Given that we were hiring anyway, we said sure so we talked with him. Unfortunately because of visa issues we couldn't hire him but if not for that, we definitely would have. It was a case of right-place-right-time, but it definitely was something we talked about for a while afterwards.

I've done something similar by creating a 3rd party companion website for an online marketplace (which has ~50 employees), but haven't contacted the company directly. Now I'm stuck. What Shane did requires not only hard work, but the guts to engage the company and knowing what it is that you really want. If you're considering this, make sure you're resolved to a particular course of action.

My site targets sellers from that marketplace and provides a search of information scraped from the official source as well as detailed sales statistics which are not available from the official source. For active users, these two things can easily save several hours per week.

The 1st party company has acknowledged the existence of my site and indicated to their users that they'll allow it but are unaffiliated, which is completely understandable since they have no idea who I am. My companion site was created out of necessity and receives about 20k pageviews a month (approx 2000 users).

Currently, I am not charging for the site but a half a dozen people have suggested charging for its use or contacting the 1st party site to license it to them. The people making these suggestions are the marketplace sellers from the 1st party site (the users who are common to both sites).

But now there are difficult decisions to be made. I've worked from home for over a decade and loathe commutes, even those measured in minutes. This company is 2.5 hours away and best-case public transportation would have me out for 12-14 hours per day. This company makes no mention of any kind of remote work possibility but my impression is that it's done some of the time by some of their employees. I wouldn't want special treatment even if they offered it. With all of that said, if I did have to travel to work... this place looks like the kind of place I'd enjoy working. It was relatively easy to find about 1/4 of their team on social media and get a feel for their culture, even found some video of their office on a regular workday.

If I did join them and the commuting situation were overcome, would that constrain my freedom to make the new features and enhancements that the community wants? Contacting them with a laundry-list of questions feels wrong.

If I didn't join, would enough of my currently free users convert to paid to make it worth continuing? What's the optimal price to balance the seesaw of retention vs dollars (number retained free users * price per month)? Is it unknowable? What percentage of the existing users might actually pay? It's all very uncertain. It'd be great to get some feedback from everyone, maybe with your own experience(s).

Shane's idea is great but it doesn't magically fall into place, relationships are complicated!

Not everyone wants to run a business.