[marcamillion]

I am very grateful for this post. One of the most common pieces of valuable feedback I got before starting my company (as a sole founder) is that I need to keep going no matter what - especially in times of self-doubt.

I always considered myself to be confident, and self-assured (not obnoxious, just confident)...but starting a company is a completely different cup of tea. I have both a Computer Science degree + an MBA. I learned Rails on my own and I thought that would be the hard part. Just to learn that transitioning from hardcore product development to sales & marketing is even trickier than I thought.

When you think about all the promises you have made to people, and things you have sold in various ways, it's perfectly natural to get self-doubt....especially given that things will NOT happen exactly the way you planned. This. Happens. A. LOT.

Self-doubt is one of the most unspoken about aspects of starting a company and I am glad that Ben has so courageously spoken about it so publicly.

If you have never done a startup before, nothing can prepare you for the experience fully. I read every PG essay, most of Founders at Work, almost every other bio/story of most if not all of the tech founders from Fairchild Semiconductors to Facebook, watched dozens - if not a hundred+ - of Mizergy interviews, understand finance & economics (I can explain the differences between a Collaterized Debt Obligation & a Credit Default Swap), also know most of the fine points of the standard term sheet (including to focus less on valuation on more on things like liquidation preferences, etc.), know enough legalese to understand most contracts, I built teams from scratch, recruited people to work with me on a project bigger than myself but under-resourced, hell even worked at another startup before...but having done all of that...I still wake up every morning and there are MANY things that I am tackling for the first time - and it makes me doubt myself.

Most people won't talk about it, but I think we need to start being real with ourselves - for the health of the startup community. Especially for those of us that don't have investors or many mentors, or don't live in the Valley, or are not YC-alums.

So Thank You Ben. For being so honest. For being so real.

[lionheart]

Completely agreed. I'm a sole founder as well and my friends keep telling me "wow, you really know your stuff" but in reality I have no idea what I'm doing.

I spend all my time in a state of confusion.

But after a while you get used to it, actually. And you just keep going and learn as you go.

[jaxn]

I am a first time CEO too. I have startup experience and even experience as a business owner. However, being CEO of a startup with outside investors is a whole new experience.

I am lucky to have great investors, a strong and friendly board, a few great employees, but like you said, I often am doing things I have no idea how to do.

My one tip to other first-time CEOs: over communicate. I send out a weekly(ish) internal email to my team, board, investors, and advisors. Everyone gets the same email, so there is no bullshitting. The investors love it.

[speleding]

Thank you for that post. I wish I could go back in time 5 years and read it then. I'm an MBA + CS degree bearing startup founder with autodidact Rails skills too. Now, I don't really need the advice anymore having it figured out myself already but it's nice to see I'm not alone.

If you are lucky, the self-doubt makes way for self-confidence eventually. Even for completely new things you start thinking, "well, I managed the last few times, it will probably work out OK this time too". I wonder if all the confident people I see starting out just have naive bravado or are very good at hiding their self-doubt.

[ditojim]

everyday is a series of lessons that prepares you for tomorrow and beyond. build on it. i think it is generally understood among any startup ceo's that this is what its like. honestly, i don't think it is something that should be openly discussed. i've shared moments of doubt with individuals very close to me, just needing to be human in rough times of building my business, and it did not help. you find inner strength to deal with the challenges and learn to leverage every possible resource to solve each and every problem that comes your way. it is just what you do...or you fail. i love it now that i know what it is, but it does take some time to grow into. and i am not claiming to know what tomorrow will bring, but i know i can handle it, and more importantly, my employees are confident that i have a firm grasp on their future.

[newman314]

As I've often said in the past: "Fear (of failure) is a great motivator"