In a comment I made on Hacker News, I expressed my desire to write an article about the differences and misconceptions between being a single-founder and having co-founders. This is not that article, but it is related. The application for YC W12 is open, and in response to my comment I received a few emails asking about applying to YC as a single-founder. What follows is one of the emails (used with permission) and my response.

Hi Chad,

I applied to YC W2011 as a single founder, but didn't get in. Fortunately, in hindsight... This year is different, I feel my startup is infinitely better than it was last year.

Which brings me to my question: did you address the fact that you were a single founder in your application? I know PG (and the rest of the team at YC) is reluctant to fund single founders, so I feel there's something that I have to 'prove' in my application.

Also, if you knew what you know now, would you still have moved to Silicon Valley, or would you have bootstrapped the company from home (NC)?

Keep on jazzin!
-Dirk

Hi Dirk!

These are all good questions.

I didn't know much about YC when I applied (a friend of mine had suggested I apply since I was working on my own SaaS site). I was completely naive about how startups work, what the VC world is like, what Silicon Valley is like, any of that. But of course, I had the idea that I could strike gold in California by starting my own company and heading West, so I applied.

At the time, I had no idea there was any big deal about being a single-founder. I was oblivious to all of that. I just applied answering the questions the best I could. Somehow I got invited to the interview. Then somehow I got accepted.

The first day of YC everyone asked, "Where is your co-founder?"

I said, "I don't have one, why..." They all looked at me like I was crazy. This was my first real encounter with the single-founder/co-founder issue. The YC partners were pretty insistent that I find a co-founder, and they set me up on a bunch of co-founder blind dates. Yes, it was as awkward as it sounds.

Ultimately, I didn't find one before demo-day, so I just had to power through alone then continue the search afterward.

At one point I gathered the courage to ask PG, "Why did you accept me as a single founder since you are admittedly bearish on them?"

He said, "Well, you seemed like you knew what you were talking about and were confident about it." I'm still not sure if that was the deciding factor or if there were other reasons, but the end result was that I got in. It's funny, but looking at the calibre of the groups they have accepted in the last few batches, I'm not sure if I would get in now.

So, I guess to answer your question specifically, I would say fill out the application confidently and concisely, but don't make it feel like you have an inferiority complex because you realize you are at a disadvantage as a single founder.... if that makes sense.

The second question is quite a poser. I have thought about it occasionally, but not very seriously until you straight-up asked it.

I went into the whole process completely naive and green. If I had a crystal ball that would have let me see two years into the future and seen all the struggles, heartache, and pain I would have had to deal with trying to make a startup successful, I would probably have been scared to death and abandoned all hope (by the way, for more on this topic from my experiences, you might want to read my entire article about it - Startups Are Hard - long, but I lay it all out).

However, perhaps ignorance was bliss. I didn't know how hard it would be, so I was willing to try it and see what happened. I have learned so many things in the last 20 months that I would have never learned if I had stayed in NC. In fact, I probably would have burned through all of my savings in a few short months and have been back to job-hunting in NC during a time that finding a tech job was near impossible. It would have been a very tough situation.

My future at this point is still uncertain. I haven't achieved the Startup American Dream (yet), but the knowledge and network of people I have gained has been fantastic. I think moving to Silicon Valley was a major part of that. If I had to do it all over again, I would certainly do some things differently, but moving out here would be something I would definitely do again.

Especially for single-founders, the ultimate question boils down to: Do you want to do something that is a lifestyle business (i.e. pays the bills, maybe earns some extra cash to spend, and allows you to work at home and spend your time on your terms)? Or, do you want to do something big which requires lots of time and other resources?

If you want a lifestyle business, you definitely do not want to take on any outside investment and should bootstrap from home, especially if home is somewhere with a lower cost of living than SV. There is nothing wrong with this. Sometimes I think lifestyle businesses get more bashing than they deserve in SV-centric circles, but that's just because all the wheels out here are greased with VC cash. I know several people who are happy doing this.

But, if you want to do something big in the tech sector, you absolutely must be in SV for the connections, money, talent, etc. Eventually you will need to build a team if your big idea is big. Realistically this means getting a co-founder or two at some point along the way. Big companies can be started by single-founders, but it is clearly the exception.

Hope that answers the questions to some extent. Everyone's experience is unique, especially for single-founders. Best of luck to you.

Futher discussion on Hacker News

— Fin.

Like this post? Please share the love!