Ask HN: Tips for Solopreneur?

I'm now in year 10 of being a solopreneur. My main business is https://www.pubexchange.com, an platform that helps publishers exchange traffic with other sites, as well as buy/sell traffic. My answers below are related to that, but I've also launched https://forourschool.org, a free fundraising platform for schools, as well as a few other small sites.

1. It is just me - is that a red flag?

It has never been an issue for me, but I also had that concern in the beginning. I try to be VERY responsive to emails and quickly address any issues that come up, so that usually helps address their concerns if they have any. I sometimes refer to the business as "we" (e.g. "we are rolling out new functionality"), so it may not be obvious at first that it is a one-person company, but I never deny it, and most publishers I work with and have spoken with know that it is just me.

I've worked with major publishers like Huffington Post, Aol, CNN, Time/Meredith, Yahoo, etc. Some have required approval by their information security team, which can take a very long time. There are always small issues that crop up, but being a one-person team has never stopped me from getting approved.

2. How do I set appropriate milestones for me to reach? Do I think about reaching 100 customers before reaching 5 recurring customers for example?

I never really had defined milestones. I was happy to leave that behind when I left my corporate jobs. In the early years, I had so much excitement for the business and its potential that any time another publisher said that they were interested in using the platform, it gave me more motivation to spend time on it and grow it. I guess if no one said they were interested in using it, I would have questioned continuing, but it never came up.

For reference, it took about 3 months for the first publisher to dip their toe in the platform and 6 months for a full integration (god bless them for trying it!). If you are interested, the first sites to sign up were Upworthy, Refinery29, POPSUGAR, Fashionista, and Remodelista (3 of them still use it!).

3. I'm in a small town in PNW. Does that matter if this will be an online thing anyway? Why or when do people move to big cities like Seattle/SF/NYC/Austin etc.

I'm in NYC, but I avoid in-person meetings as much as I can. They take too much time and don't provide much incremental value. I also have not had an in-person meeting since the pandemic started. So no, I don't think it matters.

4. What are some ways to do marketing? Should I even think about that before I have a few customers who are using my product consistently?

I have never spent any money on marketing. I send cold emails pretty often (which is mostly ineffective), but other than that, my business grows through word-of-mouth (it works like a social network, so there is a benefit to publishers to tell their friends, so that they can easily work with them). I also partner with some networks that work with many sites (such as ad yield management companies) who then sends their clients to me.

5. I've been inspired by the Startup School videos. Honestly though I'm not sure about fundraising and all these things, it seems very intimidating to me. What's the difference between those things and starting a company and slowly building it up?

I've never fundraised so can't help here. Unless you absolutely can not survive without outside fundraising, it would be stupid to even consider it as a 1-person company. Way too much of a distraction. That being said, if your plan to quickly build out your team, then sure, go for it.

Something that seems to be not well known by the general public:

Landing a big contract with a big company early on can be very problematic. They have a history of screwing small companies.

Small companies often seem to imagine this will solve all their problems. It seems to be the business equivalent of the fantasy of winning the lottery and then having it made in the shade. In reality, winning the lottery frequently doesn't end well and landing a big contract early on often doesn't either.

I used to imagine I would keep a file of such stories but never did. It's been challenging to find examples when I want them. But it also seems to be common knowledge in some circles.

Feel free to bite off more than you can chew and view it as a growth opportunity, but be aware that getting too much of your revenue from one client makes you their bitch. It's like all the downside of being an employee plus all the downside of running a business.

Best of luck.

Since other people are mentioning the red flags working with business critical 1-person businesses, I thought I would share a small story. When I was first starting out, I connected with Huffington Post who were very excited about using PubExchange since they were manually managing most of their traffic partnerships. For many sites, traffic partnerships can be a large source of referrals, but HuffPo took it to another level. They partnered with everybody and would link out from their homepage, so they could send a very significant amount of traffic. After a few meetings (I don't think infosec got involved), they decided to integrate PubExchange throughout all their verticals. We met in person, so they were fully aware that it was just me, but they were/are a very nimble company so they were ok moving forward. Unfortunately, because they were implementing it so quickly and using it in different ways than had been used before, the first night they implemented it, it broke, and unfortunately, it also broke all links (internal and external) across HuffPo. They took down the code, and called me that night. I fixed the issues right then (I think it took me 10 minutes) and the next day they added everything back. Never had any issues again and worked with them for many years after that.

Appearing bigger is super important. I remember a startup where we rented offices on 3 floors. Top floor was one tiny room with the MD in it, bottom had the business development guys and the middle had 12 engineers. Regularly they would bring prospects in and say “this is one of the offices, there’s another one above and below. Then they’d usher the prospects to the big shared meeting room.

They got loads of deals done and the company grew big enough to need its own building.

About 5, to break ice with that intimidation, you can approach that world with less expectations and just approach to ask VCs and analysts "opinion". Ask them for advice and see what comes. No expectations, just casual genuine curiosity on how they would perceive your investing opportunity.

At the same time, don't feel like you have to be too agreeable either. If you have a path to profit that doesn't include investors, then that's the best thing: you incorporated potentially good advice for free, kept equity and potentially opened a door for friendship with investors that in the future might become more valuable for you.

Solopreneur are my heros, I've tried a couple of things, is hard as f*ck.