Ask HN: Solo founders, what do you struggle with the most?

Seriously, I knew marketing would be important, and sales would be important when I started this thing... but I really didn't realize that when I quit, what I actually was doing was making a job change from "really pretty good engineer to full time sales guy".

I'm trying to do b2b software, which has a much different buying process. It's been quite a learning process, I've had to learn how to prospect, how to cold call (cold calling is frightening if you're an introverted engineer!!) how to actually drill into peoples pain points, how to avoid objection handling, how to find the decision makers. It's not easy.

As a senior engineer, i'd never had partner up with a junior sales guy, but for some reason I thought learning it myself was a good idea.

Of course, that's only good advice for specific situations. In my case, I'm small, not interested in rapid growth, and am focused on being low risk. I won't be rich anytime soon, but this approach keeps the hours down, and still maintains enough revenue to live like I want to.

I've worked with friends and strangers as co-founders. Even if you set the bar for a successful collaboration suuuuuuper low, you're going to be surprised by how many people will just flat out trip over it.

If I need help with something, as a solo founder, I pay a professional to come in and take care of it. They either do a good job or they don't. If they do, I call them again for the next job. If they don't, I make sure that I pay their invoice as soon as I receive it and move on to the next person.

Co-founders are way more complicated.

Most people who haven't started/grown a project before only have a vague sense about what starting a company means. Most can't seem to get beyond the fantasy of "not having a boss" while others may prioritize their own short-term gains over the potential long-term payoffs for the group/company if the opportunity presents itself.

As a solo founder I'm committed and I have a vested interest in the success of my company. If I have co-founders they may or may not be as invested as me or our incentives may not be perfectly aligned. Massive issues.

If you have the perfect friends to start a company with that's great! Do that! If you don't, don't stress out too much about being solo or try to turn someone into a co-founder that you shouldn't.

Just get your thing working.

Accountability: You're the boss and the employee, it can be really difficult to force your 'boss' self to do things your 'employee' self doesn't want to do (eg support, sales, refactoring, etc)

Sales: This has already been mentioned, but the hardest part for me is that you need to be pretty passionate about it to be successful.

Problem Solving: Sometimes you just cant "get" something, and talking through the problem aloud to someone can give you new ideas/solutions you hadn't even considered. You don't know what you don't know.

(I also have the opposite problem when the customers actually pay, because they often batch many invoices together into one payment, which makes reconciliation surprisingly difficult. I wrote a little script in Python to make that easier - sort of along the lines of "Given this total, which of these invoices could potentially satisfy it?" - but it's still frustrating.)

If the business continues to grow, I anticipate hiring someone to take care of this aspect for me in its entirety, because it's demonstrably a poor usage of my time, and I derive zero pleasure from it.

Typical run of the mill "hackathon" style startups that can be built in a week or two will have different issues.

Time wasters - people who want endless meetings and never commit. Having Tech partners is helping with this a lot though

my project is here:

https://madsportslab.com

There are two opportunities I am pursuing. One is to be a CTO in a nascent startup foundry; I would be co-founding, in a way, but there is one main person leading the initiative and therefore it wouldn't be a "solo founder" type of thing. It might happen. I am not going to talk about this one now.

The second opportunity/idea, however, is something I would do by myself for now, as a solo founder. It is about solving the problems that current cities have, by eventually being able to build a new city in a better way. Yes: taking a piece of land, and building a new city there, from scratch. Hopefully not too far away from existing hospitals, airports, schools, but far away enough that there is a lot of room to build new stuff. I would like this place to be sustainable, affordable, and a great place to live.

Every time I say this, I realize how nearly impossible this sounds. I have read a ton, wrote a ton, studied a ton, and spoke to several people, some of which could be good co-founding candidates, but none of which has shown interest in joining me as a founder.

I feel that the problem is evident, and I see a few serious "struggles" for me right now:

1) I am alone. Nobody to share the burden with. Being a solo founder, being alone feels harder, because you regularly have "down" moments and nobody is there to cheer you up.

2) The task feels unsurmountable. I fully realize how difficult it is to "eventually" build a new city; there are so many barriers, so many delays, so many friction points.

It still feels unsormountable, despite there seem to be a huge market for a radical new way to "interpret" city living, both for existing cities, and for new ones. There's going to be 60 million more "citizens" in the US in the coming decades, which means "demand" for new places to live (either in existing cities, or new ones) is strong. Worldwide that number is 1.5B more people living in cities by 2030 (or 2035?).

3) I am working on an idea that has is massively capital intensive - and I am not a billionaire. Convincing people to invest in this is going to be insanely hard.

4) Last, but not least, personal life is not too easy at the moment; I have no really hard issue to handle, but I am not the happiest guy on Earth either.

I could go on forever, but... I feel this is enough color to give you an idea.

We are looking for something like this: Then we sign agreement with customer, we create template/profile with prices and services on billing system. Then we provide services, we just add/register quantity to that template/profile. At the end of month system writes invoice with recurring service and added additional not recurring services to invoice. It means one invoice for recurring and not recurring services.

I've brought on some part-time help for the sales end, but ultimately the difficult factors to balance are:

  - My desire to grow as quickly as possible.
  - I'd like to retain all of my clients.
  - I want to have a very high client satisfaction. 

Sure, you can automate the hell out of things. But when that email from a client comes (which it will), you have to decide what to do.

Honestly, being solo is great only if you intend to build a business that is almost 100% automated but I am realizing there is no such thing.

Of course, I would not give this up for anything else because I love being in charge of my own stuff but that also means I have to always be switched on.

Knowing your goals and then spending time every day on the highest value, highest impact tasks is the job of a founder. This sentiment is captured in Brian Tracy's audiobook "Eat that Frog" which I highly recommend.

If you work in technology and are lucky enough to find yourself in a position where you can actually start a company you are on permanent vacation compared to most of the world.