If you ask a successful tech entrepreneur if they’ve made any angel investments, more often than not the answer is yes. Only, if you follow up that question with “have you made money”, the answer is almost always the same: no. Yet, many are still interested in angel investing as they see value in their existing investments, want to help entrepreneurs, and, of course, want to make out-sized returns.
I’ve found that after successful tech entrepreneurs scratch the itch of making a few angel investments, they don’t make any more investments even though they are casually interested in doing so. After probing why they haven’t made more investments, it always comes down to one main reason: they haven’t made any cash on the existing investments because they haven’t had any exits and the existing investments are illiquid.
Angel investments often take 7+ years to see a return, if any comes at all. So, after making a few investments, and not having any liquidity for a few years, angel investors get cold feet and don’t write more checks. Add in challenges like having to invest more money to maintain ownership positions for future financings (assuming pro-rata rights are respected by subsequent investors) combined with continued uncertainty about the outcome, and it’s clear that angel investing is much less glamorous than it appears.
Angel investors have a dilemma in that there’s no cash flow and an extended horizon to see any return, as well as no liquidity. Yet, there’s such great potential, both to help an entrepreneur and make a difference. Angel investing is difficult, very difficult.
What else? What are your thoughts on the angel investor dilemma of an illiquid financial model with a long-term horizon combined with the opportunity to help entrepreneurs change the world?
David Cummings on Startups 
The problem i always experienced is that every start-up company always runs out of money from the initial series A fundraise. Always. So what happens every time a start-up company is seeking additional capital and is a few months..if not weeks..from going out of business? And the next group of investors see that the company is operating on fumes? Need i say more? You’ve quoted me on this before and i’ll say it again: the only beneficial time to raise more capital is when you don’t need more capital.
The angeĺ investors are seeking a very high return on their investments and also They want to be part of an adventure. Angeĺ investors are business men which means They love to be part of a new idea, of a new business model. They love to do business.
let me clarity: raising more money for expansion seems to work, i.e., IPO’s. but raising more money in order to stay alive as a company, never seems to help the preceding investors, in my experience. hence, stay away from early rounds of financing unless you feel very confident that the start-up is going to make it, out of the gate, from internal cash flows. otherwise, it’s going to become a very expensive hobby.