Enjoyed the podcast. I thought it was funny that I was taking advice on angel investing from someone who's only had failures so far :) No offense meant--just irony. But it's clear that you really knew a lot about it. And I appreciated that you were very up front about your track record. And you could have some big success with the ones that are still chugging along but haven't paid out yet.
Thanks for sharing your experience and lessons learned.
You're welcome! Nobody talks about this subject, but it's an important part of building wealth (and preserving it).
I'll plagiarize Will Rogers: "Invest only in startups that go up. If they don't go up, then don't invest." However the advice from failures is much more detailed.
I keep a file on the companies that I would have invested in if I hadn't already made my two investments for that year. (I invested in one of them a year later.) I also keep a file on the companies that looked tempting but still had a significant weakness. I review those files every year but find that I wouldn't have changed my mind. Maybe it's confirmation bias, or perhaps it's just the way I filter my decisions. I'm getting better at it.
Everyone knows a startup that was acquired within 18 months, but the median exit is about eight years. Some sectors (like SaaS) are faster and some (med tech, FDA drug trials) are slower. Some tech that would have been a startup five years ago (3D rendering, smartphone apps) is now cheap enough to do with funds from founders, family, & friends. Several years ago I had a chance to invest in a movie for $3M but I passed. Last year the producer figured out a way to do it on Kickstarter for under $500K.
Another approach is "index investing" in an accelerator. Blue Startups (BlueStartups.com) raises funds from angel investors and gets matching funds from the state. They invest $70K in each of their startups (for equity) plus $200K of in-kind services and 3-6 months of mentoring. However the fund is expected to last for at least 10 years, has a small management fee, and might only liquidate when the last startup of that cohort has had an exit (or shut down). There are thousands of accelerators across the country, ideally each focusing on their local area and industry sectors. As far as I know, Blue Startups is the only accelerator where the investors go surfing with the founders.
In the podcast I mentioned Innovasc as my second investment (late 2008). They put out a press release last month:
http://www.intactvascular.com/intact-vascular-secures-38-9-million-in-series-b-financing-to-accelerate-development-of-endovascular-dissection-repair-technologyThat puts the company firmly in the category of "everything has to go wrong to fail", but in 2010 the founder was scrounging loose change out of the sofa cushions and barely staying alive for over two years of cardiac research on $600K. Today, as soon as they add the FDA's 510K certification to their European CE, they're an acquisition target. When the company started, they expected to build a better cardiac stent. But in the last seven years, "peripheral artery disease" (diabetes, obesity) has grown faster than cardiac disease and is a much bigger market for their tiny little "Tack" stent. Personally I'm hoping that a European multi-national medtech will start a bidding war later this year...
Every time that I think I'm jealous of Clif's unqualified success in his company, I look back at my due-diligence notes on that founder's business plan (especially the political risk in two foreign countries) and run away screaming. But the founder writes investor letters that read like Buffett, and he's churning out money faster than a U.S. Treasury printing press.
Another Hawaii Angels investment (before our time) involved a chemist creating a better coating for french fries. Nine years later, much to everyone's surprise, it has turned out to be a magic chemical for extracting oil from shale fields. Everyone knew the chemist was bright enough (and diligent enough) to succeed, but there's not much overlap between those two research areas.
Next time you're in Hawaii we'll bring you to a Hawaii Angels lunch (2nd Friday of most months). I'd be happy to give a surfing lesson, too.