Ask HN: How do you deal with being a solo founder?

I quit my job in early 2013 to do my solo start up. I'm still developing the product today. I'm not sure if the following story/advice is good, but it represents my experience and ultimately shows how I managed over my hurdles.

After quitting my job I set all kinds of expectations on myself. None were reasonable. Every time I had coffee with friends or past colleagues I would get asked how well I was doing and when I might be complete. From day one I felt pressure to achieve some milestones and when these questions came up I inevitably declared unrealistic targets. Worse, after I declared these targets I would feel like crap as began to realize I was nowhere close to meeting them. It got to the point where I would just stop working.

At one point, I stopped for 2 full weeks before deciding to face up to the truth: I obviously wasn't prepared for what I had decided to do. I was failing...

I then realized that even before I quit my job I had been in the habit of biting off way more than I could chew. See, these big corporations I had previously worked for had instilled some really bad habits. They would intentionally give employees more work than they could actually handle, with the idea that they were challenging their employees. No big surprise that every year the performance reviews would tend go the same way. Managers would identify with all the achievements and show understanding on initial goals that were not reasonable to begin with. It makes the employee grateful to manager for the big bonus and also makes the manager out to be a keen observer with great understanding. Certainly fosters a good relationship. The downside in all this is that they establish a really bad pattern/behaviour to have unreasonable goals with reasonable outcomes. I'm not going to get into the good and bad of the practice suffice to say it didn't help me when switching to a start-up. In fact it made me feel like shit along the way.

So I decided to stop and made a huge list of all the obligations in my life, and I mean everything. From family time to shovelling the snow, mowing the grass, and paying the bills, but more importantly I then prioritized them with a cost ranking. I discovered something interesting. It turned out the things I perceived as small or insignificant we're consuming large portions of my thinking time. While they would only take a very small amount of time to deal with, they had a big 'nag-effect' until they were done. For example: doing taxes. I spent months with background thoughts focused on my changed situation and wondering how optimize any re-situated tax implications. This item was always way down on my list in importance and should have been much higher had I understood myself well enough to identify it was costing me more than I realized.

I continued on by spending the next two months really simplifying my life. I took my list of 100+ ongoing obligations and reduced it to 10. ONLY 10: ongoing.

Afterwards, I got back to work and became really productive. These days I make sure I set small goals with really lofty timelines. I'm pretty sure some people will find faults in this new practice, as I can see obvious faults myself, but that's ok. I'm now the happiest I've been in 10 years and I don't fall into anymore motivational ruts. Week by week I'm consistently happy with my accomplishments and for the last 5 months or so I've maintained enthusiasm with almost everything I do.

So I'm not sure if this is helpful, but here's the advice:

Allow some time for understanding who you are and how you best operate. It's really important to get your head in the right place, before you start and along the way as you observe problems. Be aware of your thinking patterns and don't be afraid to make really big changes if that's what is required to get you there. Only set timelines that are reasonable to accomplish. Review all timelines/expectations and spend some time trying to call bullshit on them.

I have been going for over a year because I simply love what I am building. DoerHub is designed to help people do more together - to enable serendipity and power meaningful projects http://www.doerhub.com ↗ and http://www.doerhub.com/for/doerhub ↗ .

I've had more ups and downs than I can count - several potential cofounders who didn't work out, moving solo to the Bay area, trying to survive school in parallel because it is tremendously helpful to the business, etc.

At the end of the day, I see this as a my masterpiece - every peace of it is built with love and I am testing the impact of each new component as I go to make sure I'm heading in the right direction. I start a new piece of functionality every day and don't go to bed until it's done. When I hit a wall with coding, I do biz dev or something else. Resting from one to do the other. I catch myself thinking about DoerHub even when I am supposed to rest - and solving problems in my head during the most mundane everyday tasks. I have a long roadmap and the peaces are falling like dominos when I focus (first release, boosting conversion on homepage, boosting internal engagement, adding a viral feature, seeing numbers go up or applying scenario B when they don't, boosting performance, adding another needed component, etc). It feels like a long game I am conquering one level at a time.

I have met many smart people who had the skills to help, but at the end of the day, it comes down to persistence and commitment - your ability to bite down on something and not let go. So many talented people are stuck doing things just to get by, to get a bigger pay check, to get rich. Unless you love what you are doing, the people who are using your work will not feel the love in it either so it becomes a doomed endeavour. That is why I push forward relentlessly, even as a solo founder, I love what I am doing and the users can see that.

I need a co-founder and when someone comes along who wants to join me and has the skills I simply ask that they build one of the next pieces on the roadmap independently. You can't be a co-founder unless you are capable of carrying a piece of the business forward on your own. If they take too long or give up midway, we've saved each other a lot of time and can remain friends. In the mean time, I just keep on trucking. Crafting DoerHub with love and watching users benefit from my work daily. I will be doing this for years to come, and somewhere along the way I will find someone who wants to do it with me and is just as stubborn. Probably one of DoerHub's users (which is why I only promote the site within groups of amazing doers).

Stress comes with startups, so I wouldn't say I'm more or less stressed out now doing a solo than I was when I did it with cofounders. There's something to knowing I'm on the hook for all of it - it keeps you honest to your intentions, if that makes any sense. You can only blame yourself if it fails, so stop fucking around! <--- this is what I tell myself most days! :)

I'm fortunate to have a rather wide range of skills that include marketing and software development. I'm probably innately better at the marketing stuff, but I've become a much better coder since I switched to solo mode. I suck at graphics design, but I have a few close friends that do that for a living so I can get around it by contracting it out to them. I'm also awesome at PM work, and basically do it live as I'm coding. Keeping projects simple is a requirement. You don't have a lot of time to go down a technical rabbit hole, so don't over scope.

If you find yourself thinking you need to do sales and BD at this point in the game, you should probably do a level set. Get people using your product first, then worry about how you'll sell lots of it later. Given it's a good idea, it's likely it will sell itself via the marketing work you do. Get a sales guy later when you know you can increase sales conversions. I can't really say how to solve the marketing problem other than just being yourself and being honest with your users. Someone who listens well usually makes a good marketer. Listen to your users.

You can cheat at marketing by observing what similar offerings do for marketing. A Twitter account, simple blog and a few visits a month to a meetup scene or demo day during lunch at some cool company will do wonders for your moral.

There are certainly days when I get frustrated. I spent the better part of Monday trying to get mod_wsgi serving up a Flask application for a piece of my current project. I thought I was going to lose it, so I stopped and went for an hour long bike ride. I figured out the issue when I got back and was able to start writing code shortly after.

Best of luck to you! I'm convinced that solo is the way to go. If there are others in the Bay interested in hanging out and talking about it over coffee or drinks, I'd be down with it!

I've never found running businesses alone particularly stressful. Normal employment was worse to me.

Everything that can be automated is automated: backups, database cleanup, lifecycle e-mails, dunning for clients with past-due bills, accounting, bill payment, etc.

I do all my "checking on" things in the morning (e-mails/tickets, tweaking ad campaigns, server status and checking for security updates, etc). Afterwards, I put a few hours into something on my TODO lists which I manage in Trello; some days I choose to work on a new feature, sometimes on bugs, sometimes on new marketing or seeking out new partnerships, sometimes I just pick a side project to work on. Whatever gets done gets done, and some days it gets done in the afternoon and some days at night.

I don't keep a schedule. I don't stress about how much progress was or wasn't made on a daily basis. There's no boss making me stress over things, and I've always managed to move forward anyway without any external motivation. I only look back on it over the span of months; "that was a productive summer".

Financial security helps a lot I suppose. I use the profit from one project to bootstrap the next. The only time I haven't had enough in savings to pay at least 6 months of expenses was the very beginning -- when I was 18 with $0 and started college on federal loans. I didn't need loans for very long, as I started my first businesses back then (ad sales and a subscription web stats service). I plan on new ventures being profitable from the first customer as much as possible.

To cope with doubts and fear I ended up finding a group of entrepreneurs who held a regular meeting. At each meeting we went around the room and talked rather openly about the stuff that was on our mind, good and bad. It was very helpful to me. If you can't find such a group, try to find others like you at networking events and go to lunch to talk things out. I once met a dude who was also a solo founder, in a vertical niche like me, used the same technologies, and even hosted at the same provider! We had some good conversations.

The "everything to do" is a blessing and a curse. Blessing: you're never in a meeting. Curse: everything else. I think the key thing here, if you're going to do everything yourself, is to make a product that isn't too complicated. If your product requires a tremendous amount of engineering work you should get help or you'll never get around to marketing. I speak from experience, sadly.

Wanting to give up: there are two things that get me through the days of poor morale. 1) knowing that if I give up I will have to get a job working for somebody, and all this glorious freedom of being my own boss will go in the toilet. 2) The fact that I am working on something with a workable business model gives me the confidence that it's just a matter of time. My product helps solve a problem, and people who have that problem are usually prepared to pay money for a solution. I think morale would be much harder to maintain if I were trying to build the next consumer-social-sharing app or whatever where the rewards may or may not come, even if I work well.