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

Stop thinking you don't have the skills to do something. You can learn anything if you decide to, but assuming up front that you can't (forever) is dangerous. my2cents

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.

I like to take a rule from the Steve jobs playbook and use simple circles... one larger than the other but no more than 2. your most immediate target (realistic reachable) and one of the "enemy" competitor company. or overall untapped market cap. **for this to be effective you must provide as accurate projections as possible** no bar graphs and as little or no text as possible... remember that a deck is a companion to the speaker... avoid bullet points and use the deck to entertain rather than educate... is not a class is a pitch. :)

When it comes to raising money you must remember that risk is a perception. Your job is to drain the risk! Below is a link to a resource I provide my investors. The 50 questions are specific to product design/development but the 15 categories are questions that apply to any industry. If you can answer these questions about your deal you will have gone a long way to "drain the risk" for your investors and get funded. http://www.jaredjoyce.com/freetreats/50questions.pdf Once you have answered the questions for your deal schedule a call with me and I can help you integrate the answers into your investor pitch.

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.