What is your biggest challenge as a startup CEO raising money ?

Raised $2.7 M in one year for a Patient Solutions, Informatics and Analytics company. The  biggest challenges I encountered are finding the investors that understand an emerging industry, who will trust a person they don't know and building self confidence to articulate our company's purpose, mission. Most importantly being able to demonstrating our ability to generate returns on their investment beyond what's on paper. This was my first time to raise external capital of this size and the breakthrough during our capital raise process was our ability to find the alignment and intersection between our company's vision and the investor's desire to participate in the industry we're helping build. I understand that Pitch decks need to be perfected but until you find that emotional and rationale connection between you and the investor, Pitch decks are simply door openers. Then the real work begins ... we relentlessly establish credibility and trust to deliver results. 

This is for a $100k raise. The biggest challenge has been getting each investor to finally sign the documents and send the check. It basically becomes a matter of poking and prodding. I try to make it as easy as possible by sending things pre-printed and providing a pre-addressed, pre-stamped envelope. Even then things can move slowly.

Biggest challenge for me is finding an investor who's willing to invest in a single founder startup, even though business is passed MVP stage and generating revenues. Next challenge in order of magnitude is finding an investor/angel who doesn't say: Looks great but it's still too early for us.

Thanks Varun - very good point!

Kodjo - Thanks. I just added a comment to my question. Because I noticed through your question that it is an often raised concern but also a fact of life that single founders don't get funding - always exceptions but very rare.

For almost any investor there are two requirements that a startup has to come up with:
1) Having a bold idea that has a significant impact on a large market
2) Having a stellar founders team of two or more founders
These days single founders have almost no chance to get funding - take it as a fact of live. There is a multitude of reasons - some of them:
* It's almost impossible for one person to be a developer/producer/creator/servicing person and a sales and marketing promoter at the same time. And running a company with high potential it's literally impossible.
* People with big ideas attract big player to join the game. If not, the idea is bad or the person is not able to communicate and lives in isolation (relatively speaking) both not the fabric of a great founder
* People who attract a stellar team right out of the gate will most likely also attract customers, business partners ... and .... investors
I myself would not invest in a single founder company unless I've seen at least two of those who actually succeeded.

Find a cool person helping you - it's so much more fun to work through the rough times with somebody else anyway. ;)

The current system seems to be all about whether you are one of the old boys in the club of people who have launched a VC funded enterprise before, and not at all about the uniqueness, quality and marketability of the IP that you have.  This is so absurd that I am not surprised that most VC / angel investors  don't make any money.  If you have good IP, the place to look for money is with companies in the market sector you want to serve.  That worked for me.  The current VC paradigm doesn't work, but the people in the industry don't have the initiative to abandon it, even though it doesn't actually bring home the bacon.  When I look at the websites of this herd of sheep, I see that they all congratulate themselves on their originality, yet they all use the exact same paradigm. 

One VC firm funded a fast food chain that will sell breakfast all day, and nothing else.  Obviously, if that worked, all of the fast food chains that now sell breakfast would just also sell breakfast all day.  If nothing else, they would all do it when they saw market share being taken up by the all breakfast 24/7 chain.

The paperwork for joining this group is a perfect illustration of the problem.  They give a list of trendy areas of the economy, based on the fads that VCs tell each other are hot, and ask which you are in.  Well, I'm in none of them, and I don't want to be in any of them.  Joining the thundering herd off to the latest fad is never going to be a path to success.  The psychology of those who never outgrew junior high school emotionally is always going to lead to everyone trying to do the same thing at the same time.  It's even worse when the thundering herd falls in love with a bad idea - such as compostable bioplastics. 

Compostable bioplastics are bad, expensive plastics.  They're yard to make, they rip easily, some only biodegrade in an artificial environment, etc. etc. etc.  They are always going to be inferior, more expensive plastics - but VCs looooooove them. Billions of dollars are poured down that drain every year.  And yet, the more often the paradigm is proved wrong, the more ardently the VCs subscribe to it.  Trying to talk to the cult members about this is an exercise in futility.  They all want to climb on board the Hale-Bopp comet that will take them to heaven.

My next project is to use the same IP for making an additive that makes ordinary plastics biodegradable for improving bioremediation of toxic waste contamination in the environment, and at the source of the toxic waste.  I will be talking to businesses who are in the field, not to VCs or Angels.

Biggest issues are unrealistic expectations around early user traction and domain expertise (for non-consumer plays).

I have 3:

1) Build the network to be introduced to the right investors in my industry.

2) Conceive a B plan "bootstrapping strategy" to move ahead if, for any reason I don't find funds or to late..competitors don't wait..

3) Conduct plan A & plan B in parallel (in mind) to rebound.

Biggest challenge is being an individual non-techie-boomer-female-founder trying to find a co-founder to help me develop SILICONLAUNCH.COM

Also, please do the math on single founders vs 2 founders.  If you can make it to seed as a single founder, that leaves you equity to land 4 or 5 person founding team and stake them to work, instead of that 1 other guy who started when the product was something else.

To add to the difficulty in finding the right investors... it's an incredibly distracting process.

Fundraising is typically an entirely unrelated business operation to your day-to-day, and therefore can get in the way of that day-to-day. The path to a successful early-stage fundraise is generally longer than you expect, so it's important to be able to manage the growth of your business while attracting and organizing investors. There are many inefficiencies along the way, which is a huge reason why I'm working to make the process easier on founders and investors alike.