What is the most challenging part of Raising Capital (with or without Federal Opportunity Zone Tax Credits)

I'm both an active angel investor and entrepreneur who has recently raised capital. I'll start with what is standard in Silicon Valley and then apply various multiples and discounts where relevant. For an angel or early seed round, the current going rate is $3m-$5m pre-money via a capped note or priced round. Priced Rounds typically most often use the "Series Seed" docs and Convertible Notes typically are 18-24 month terms with a 15% discount. I don't mean to be argumentative but Marco is incorrect that valuation can be avoided by a capped note. And in general, there is no way to avoid setting a valuation except via an uncapped note, which is almost unheard of. Setting your cap and discount will have a significant impact on your cap structure, the same (and in some cases) worse than a priced round. This $3m - $5m range is what I'd call current market value in the valley for "ideation-stage" capital. This is that there is a team in place, typically some form of MVP and in some cases some very basic market data supporting the general thesis of the raise. In the other market I'm familiar with (Canada), the range for the same stage of capital is $1m - $3 with most being in between $1m and $2m and most preferring priced rounds over notes. These rounds rarely have a real lead since the raise is typically $500k or less, so if you price it reasonably, most (good) angels will accept the terms as is. The low and high end of the ranges are discounted and pushed by the credibility presented most often by the team (done it before, worked for a notable company, had some relevant success) or strong evidence of the thesis being correct. It's also the Founder's option to price the round at the top end of reasonable or provide what you might consider a discount, depending on the kind of investors you are courting. So while this is what I'm seeing as "current market conditions" there is price elasticity in any market. The best way you know if you've priced it right, is if people are buying. Any angel investor should be able to give you a conditional answer after the first meeting (subject to playing with the product, reading terms, meeting the rest of the team). Any angel investor in ideation stage capital who can't give you a yes, no or subject-to yes in the first meeting is not worth pursuing IMO. Any investor who can't close within 3 meetings or conversations won't close (9 times out of 10). Happy to talk to you about the specifics of where you're at, what might help you improve your odds and generally get you closer to the point where you're ready to raise.

I'd need to understand a bit more about your business, but I suspect one answer is to work toward getting an accounts receivable-based credit line. Amazon is a good company that pays it's bills. Lenders will either loan against the Amazon receivables or buy them from you at a discount. This approach is expensive but if cash flow is your issue, worth exploring.

Angel Investors will understand that you have a need to draw a salary... but the idea of taking their cash and putting it to personal use would be a "no-go". If you were on your Series C of Venture Capital, raising $100M and you wanted to sell $3M of shares to buy yourself a nice house, for instance, that might be okay. But if you're raising $500k and you want to pocket $50k of that to clear your credit card debt (for instance), that would be a deal-killer. Two reasons: (1) it shows the investors you're not great at managing your own funds, and (2) it's hard enough for a company to survive and grow with the investment that Angels provide — they definitely expect every penny to go into the company's growth. That said, if your profits are strong and the reason for the equity sale doesn't set off 'red flags' (i.e. family medical expense?), maybe you can get away with it. But remember: investors get pitched by hundreds, even thousands of candidate companies. That's your competition. Some of those companies look just like yours, and *don't* have a founder who's looking to use some of their cash for an early exit. So, it would be a significant strike against.

It entirely depends on the kind of business you have. If you have a tech startup for example, there are pretty reliable assumptions about each round of funding. And a business plan and financial forecasts are almost totally irrelevant to sophisticated tech investors in the early stages of a company's life. Recent financial history is important if the company is already generating revenue and in that case, a twelve-month projection is also meaningful, but pre-revenue, financial forecasts in tech startups mean nothing. You shouldn't give up more than 10-15% for your first $100,000 and from that point forward, you should budget between 10-20% dilution per each round of subsequent dilution. In a tech startup, you should be more nervous about dilution than control. The reality of it is that until at least a meaningful amount of traction is reached, no one is likely to care about taking control of the venture. If the founding team screws-up, it's likely that there will be very little energy from anyone else in trying to take-over and fix those problems. Kevin is correct in that the board is elected by shareholders but, a board exerts a lot of influence on a company as time goes-on. So board seats shouldn't be given lightly. A single bad or ineffective board member can wreak havoc on a company, especially in the early stages of a company's life. In companies outside of tech, you're likely going to be dealing with valuations that are far lower, thus likely to be impacted with greater dilution and also potentially far more restrictive and onerous investment terms. If your company is a tech company, I'm happy to talk to you about the financing process. I am a startup entrepreneur who has recently raised angel and VC capital and was also formerly a VC as part of a $500,000,000 investment fund investing in every stage of tech and education companies.

The best time to raise capital for a startup is when you have a clear idea of what you want to do and a clear idea of how much money you need to get to a milestone that will set a higher value for your company. In general its better to bootstrap and do friends and family as long as you can, because the more mature and successful you are the better deal you will get from angels or VCs.