Reflections on Angel Investing

This month marks my 10th year of angel investing so I synthesized a few learnings as a complement to the more tactical “Angel Investing Learnings” post from last year.

This post is broken up into three parts; dissecting the why behind angel investing, understanding your asymmetric advantage and how to apply this advantage in the investing process.

Why Angel Invest?

I don’t think that you should angel invest if you care most about compounding capital — there are probably better ways to achieve this goal with lower time commitment. Angel investing has been one of the most fulfilling things I’ve done in my career, and has the following benefits many of which are not tangible or easy to measure:

  • Relationships: You will meet amazing people along the way; entrepreneurs, co-investors, and limited partners. Each of these connections has a chance of becoming a meaningful professional and personal relationship — collaborating with more people gives you the chance to both expand and deepen your network and relationships.
  • Learning: You will get an insider’s view into the positioning and evolution of a wider range of businesses that are successes and failures. You get to talk to founders making hard decisions and learn during the investing process and throughout years of partnership — this can help you become a better operator and / or investor through pattern recognition.
  • Paying it forward: You get the opportunity to support former colleagues, friends and folks earlier in their career or with less access to capital. It’s a wonderful way to leverage your own learnings, relationships and capital to help pay it forward.
  • Compounding capital: Your money will typically be tied up for a long period of time (illiquid) unless the company does well and has some sort of outcome (sale, IPO, secondary transaction). By definition this makes you a long only, value investor as you are forced to compound your capital without “messing with it” like you can with liquid investments especially as an angel.

If you’re going to make just a few investments then accept that you will likely lose it all, but if you are going to make 15+ investments then take a portfolio approach and expect at least one company to “return the fund”. Your choice here will depend on your personal situation and risk tolerance.


Asymmetric advantage

Angel investing is all about leveraging your asymmetric advantage — you need to know something that the market does not know better than the market in order to make good investments. I think of asymmetric advantage in three buckets:

  • People: You know the people involved in the business better than the market – for example you personally know the founders (ideally you’ve worked with them) and/or know some of the other co-investors well. If you’ve known and collaborated deeply with these folks then you have data that is hard for other investors to easily replicate. Abe Othman (AngelList) refers to these as “credible deals”.
  • Industry: You know the business model or the industry really well. If you’ve been an operator in the space you’ll have a good understanding of what it takes to build a successful business. I’ve made the mistake of knowing the pitfalls of an industry “too well” and not being able to see past these risks for some good investments that I’ve missed, but mostly more industry knowledge has served me well.
  • Market: You know the market/geography (e.g. I invest in Kenya because I grew up there) better than the other investors. If you understand cultural, economic and political nuance about investing in the market you will make better decisions. This is why many venture capital firms are “local”.

I’ll occasionally make small investments in companies where I have no asymmetric advantage but I try and make these as small as possible and with founders that I have a strong connection with and feel like I will learn from them throughout their journey.


Where can you leverage your advantage?

As an angel investor you should try to leverage any asymmetria advantage across the investing process, which I think of in the following buckets:

  • Seeing: If you have great deal flow and see a lot of quality companies through your personal brand, network, writings/media or your affiliations (e.g. where you work) it helps you pick from a larger sample set. Being in the “flow” of quality deals is very important to be a successful angel as you have more to pick from.
  • Picking: Picking is very hard and often separates the great angels from the good angels. This ultimately comes down to judgment, repetitions and a long time horizon built from successes/failures and great mentors. I still write memos (and post mortems) for every investment that I make, even if no one will ever read them but me as it helps me get better at picking.
  • Closing: Once you’ve picked a company to invest in, you need to “sell yourself” to get into the round which is now getting harder and harder for quality companies as more capital and angel investors flood the market. This is often a function of your connection with the founders, your personal brand or affiliations or very specific knowledge you can bring to the company.
  • Building: Once you’ve invested, how can you help the company? Are you an expert in a particular area, have specific biz dev or fundraising connections, or could you ultimately even join the company to help them scale? I’ve been most effective at helping build with very specific point in time asks such as specific intros or meeting a senior potential hire.

Angel investing is multifaceted craft that will likely take many lifetimes to master and involves a healthy dose of luck. I find it intellectually stimulating and personally fulfilling and I expect it will continue to be an important part of my life 🙂

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