Angel Investing Learnings

In this post I’ll share some advice and learnings from a decade of angel investing to help others get started or improve their own process.

I’ve been investing in startups for about 10 years through Musha Ventures, after learning the ropes at Index Ventures. I’ve made ~70 investments (around 40 in Africa), and realized around twice my total invested capital (Distribution to Paid in Capital – DPI). Most of the companies in my portfolio (~55) continue to operate without a realized liquidity event.

I love meeting and learning from founders, and being exposed to different business models. When I support a company, I am able to learn from observing it grow or fail and build friendships with the founders beyond my small investment. I think that early stage investing has made me a better product person and operator, and I hope to continue to support entrepreneurs throughout my life.

Investing Frameworks

Ben Holmes, Index Ventures

I worked with Ben Holmes at Index Ventures, who led their investments in King, iZettle, and Just Eat. He showed me a simple framework, which is still the foundation of my investment evaluation process, detailed below. At least one dimension of Team, Technology or Traction should be an A+, and a big enough Market (now or in the future) should be a precursor to making the investment.

  • Market: Is the market big enough ($1Bn+) and can you see this company being a leading player (with 10%+ market share) in the next 3-5 years? If you think that the market now or in the future is too small, then don’t make the investment.
  • Technology : Is the product or technology differentiated and sticky within their market? How difficult is it to replicate?
  • Team: Is the founding team both individually exceptional and complement each other? How deep and long is their professional relationship?
  • Traction: Is the business growing and do they have positive unit economics? Do they have paying users? What does customer retention look like?

Brian Singerman, Founders Fund

I don’t know Brian Singerman personally but I really enjoyed this episode of “Invest Like the Best” with him. He’s invested in companies like Oscar, Affirm, Wish, and AirBnB. Here are a few of my takeaways from the conversation:

  • As a startup market, moats and execution are the only things that matter.
  • As a VC, seeing, picking and closing are the only things that matter.
  • You learn to invest in venture by actually investing, not by observing.

Investing Advice

This is a collection of advice when you are starting to invest, in no particular order:

  • Learn with small investments: Optimize for learning per dollar invested if you are just getting started, have limited capital and hope to build a portfolio. If you invest $1k with the same diligence process as if you were investing $100k, then you will learn by making less expensive mistakes early on.
  • Take it slow: Start early in your career but start slow, and invest more frequently as you improve your judgement – I made too many investments in my first year. It takes a long time to calibrate your gut because it can take 10-15 years to figure out if you are a good investor (but you’ll get some validating and invalidating data points along the way).
  • Asymmetric Advantage: Invest in areas where you have some asymmetric advantage. If you know a founder super well, or know a space really well and can invest in a related company (without conflict) these are sources of asymmetric advantage.
  • Time vs. Money: Invest money in companies that you would be willing to spend your time on personally, but may not be the right personal trade off for you. When you are earlier in your career you can think of time and money as interchangeable. If you don’t have the capital to invest, then try and join these companies and get some equity for your time.
  • Deep Relationships: Invest in great teams who’ve known each other a long time and even better worked together for a while – it reduces the risk of founder issues (65% of company breakups are for this reason).
  • Founders you like and respect: I invested in a few companies that I did not have the best rapport with personally, or had an unexplainable ‘gut’ reaction to avoid even it if looked good on paper. Most of these companies did not work out, but I have a small sample and so this still needs more data.
  • Company first, then terms: Terms are less important than believing in the company and the founders. Don’t make an investment because of a low valuation or tax incentives – these are all bonuses, and never a reason to make an investment. I made a number of mistakes here early on and regretted them.
  • Valuation: If you are going to negotiate on anything, negotiate on price although this is mostly supply/demand driven and you may not have leverage if you are a small investor. There is a common belief that valuation does not matter in venture capital, but if you are investing your own money then overpaying consistently will hurt your returns.
  • Cap table: Look for ‘clean’ cap tables (equity split) in early rounds. If the founding team has an unexpected equity split, or there are early inactive employees/ investors significant equity it can affect the company’s ability to raise money in later rounds and if founders are too diluted, then they may lose motivation.
  • Discipline: Founders who are structured and regular with investor communication are often also good operators. If they show discipline with investors, they are likely applying the same discipline to running their companies. I often ask for the last investor report to get a sense of their communication quality.
  • Metrics: Founders should be super on top of their key metrics, growth rates, revenue distribution, burn rate etc. This shows that they both track them carefully, and review them frequently.
  • Sleep on it: Even when I really like a company, I always sleep on the decision and never commit after a meeting. If I still feel good about it the next day, then I’ll message the founder to invest. Try not to get pressured, or react to FOMO and make a decision too quickly or without conviction.

Practical Tips

This is a collection of more practical/tactical things to do when you are investing:

  • Track your portfolio: If you only make a handful of investments, then think of it as money spent and a nice bonus if one of them is successful. If you have a portfolio, then keep a strict record of your investments and track their progress and returns (I use a simple Google Sheet). I track key dates like fundraising events and summarize the status of each investment about once a year.
  • Write Memos: Your memory is less reliable than paper record, and so I recommend writing short 1 page memos with the ‘why’ behind your investment. I’d start with the structure I outlined from Ben Holmes up above and expand it over time.
  • Customer References: For software as a service businesses in particular, do some customer reference calls. I always ask the following three questions: What was in like before the product? What is it like after the product? What would happen if took the product away? If they get very upset at the last question happening, that is a very good signal.
  • Post Mortems: If companies fail, write a few bullet points down about why the company failed (I just add them to my original memo), and see if you identified the risk when you made investment. Learn from this, and don’t repeat mistakes.
  • Intro Email: I’ve just started writing an ‘intro’ email to founders which founders seem to appreciate. It allows you to clearly express how you can help, how you operate as an investor, and share some of your expectations as well.

I’ll continue to add to this list as I learn more, and please send me any thoughts or feedback!

Investor updates for startups

I’ve invested in about 30 companies over the last 6 years and received a lot of different investor updates. Some companies send few, sporadic (often too detailed), updates whereas others send updates with a fixed structure and on a predictable schedule.

I think the sweet spot for many micro vcs with a portfolio is quarterly updates which arrive on a predictable schedule – e.g. 2 Mondays after the end of Quarter. Founders who update investors on a predictable schedule generally build better companies, in my experience, as there is a correlation with discipline and organization.

Here is my suggested template for sending updates, although this is not meant to be prescriptive and more to summarize the bases covered:

Many startups often miss the ‘Metrics’ section and I think this is the area where most could benefit for improving their reporting.

Template (Quarterly)

Summary

  • Key milestones hit/missed
  • Important takeaways

Highlights

  • Limit to <5 bullet points
  • New customers, product wins, critical hires, geographical expansion

Lowlights

  • Limit to <5 bullet points
  • Lost customers, product failures, lost employees

Metrics

  • Consumer: DAU/MAU, Revenue, Retention/Churn Metric, Employees, Cash, and Burn Rate
  • Enterprise: # of customers, Revenue, New customers, Sales pipeline, Employees, Cash and Burn Rate
  • I recommend showing the same metrics in a table Quarterly and then highlighting YoY and QoQ growth

Product

  • New features or products shipped and a short summary of their impact / future impact

Team

  • New hires / team changes

Other

  • Anything that is not covered by the sections above e.g. Press coverage

Fundraising

  • If fundraising add this section to show progress / any key milestones
  • Also useful for converting existing investors for additional funding

Help

  • Specific intros to investors or potential customers generally yield the best results

I know some founders feel like these updates don’t do noticed but I read every single once of the updates I get from founders, even when I don’t reply.

Kenya – entrepreneurship, funding, and technology

Note: I wrote this about 9 months ago after spending most of 2015 living and working in Nairobi. I have had enough people express interest in reading my notes that I thought I would share broadly.

Summary

  • I lived Kenya over the last 6 months and left feeling inspired. I believe there is tremendous opportunity for awesome entrepreneurs to build products for the East African market. In particular, I would be well suited to focus on something that bridges the gap between the West and Africa 
  • There is a lot of raw talent, fundamental problems that need solving, and plenty of enthusiasm and excitement around building technology companies
  • There are few excellent company builders / focused executors and a lack of a proper seed/venture firm or decent incubator. ‘A’ level entrepreneurs (silicon valley, local or elsewhere) who have built a successful business are sparse
  • Access to seed and early stage capital is difficult and the fundraising process is suboptimal due to the lack of proper local vc funds which leads to entrepreneurs chasing short term revenue and lack of focus on the long term objective – funding/focus is a chicken/egg problem

Startups and Entrepreneurs

  • Entrepreneurs are hungry, have lots of enthusiasm and there is a plenty of excitement in young talent who want to build something awesome.
  • Startups are solving fundamental issues vs. incremental issues in the west –  access to good education, electricity, health care and phone/internet. There are opportunities to build on top of these solutions or provide additional products and services that are already mainstream in the west – I’m particularly excited about financial services.
  • Entrepreneurs often have their fingers in lots of pies, can be distracted by too many ventures, and seem to be doing too much with too little capital and too few people. This leads to lots of half-formed businesses versus a few well built ones
    • Chasing (short term) revenue is required to grow businesses here due to lack of access to capital for early stage businesses
    • This is partly due to the opportunistic nature of working in Kenya, and more commonplace with local entrepreneurs
  • Entrepreneurs lack role models in the community that they can get mentorship from who can help them with product strategy, marketing, assembling the right team, raising funding, and scaling the business. Some missing pieces:
    • Best in class experience – understanding of what ‘great’ looks like
    • Successful Kenyan technology entrepreneurs – groups of people who have built and exited an excellent businesses in Kenya (or East Africa)
  • Foreign entrepreneurs are met with mixed feelings especially when it’s believed that they are only in Kenya for a fixed period of time. I believe that foreign entrepreneurs can add a lot of value by mentoring local talent especially if they have best in class global experience and hire local teams

Investment – Venture Capital / Incubators

  • Local funds either have very little capital to deploy or strict mandates about where they can deploy their capital because of conditions stipulated by their LPs – leads to defocusing in startups
  • Entrepreneurs looking to raise small seed rounds have a few options:
    • Raise capital from local angels who are not often sophisticated investors and often don’t understand what they are signing up for
    • Raise money as grants or from funds (with LPs who have strict investment criteria) and these come with conditions that often result in unnecessary/unhelpful changes in strategy
    • Go on long (many month) investment trips across Europe and USA which are also usually an uphill battle and often result in small ticket angels vs. larger funds
  • This current fundraising process feels inefficient and distracts entrepreneurs from focusing on their product and company from both a time and strategy perspective
  • Local incubators have unfriendly terms for entrepreneurs and are not run by successful entrepreneurs or investors
    • Incubators typically have many companies vs. a few companies with lots of mentorship and focus
    • $25k investment for 15-25% of the company plus terms which are not founder friendly e.g. ratchets, clawbacks, pushing to early exit
    • Many incubators have shut down their program as they could not find enough quality companies – I think this is in part due to the fact that they were going for scale vs. focused set of companies
  • Grant funding can be disruptive and distracting – companies are incentivised to abandon their vision in the ‘short term’ (to get the grant) and end up building a frankenstein company with multiple focuses which is hurtful in the long term

Working in Kenya – personal learnings

  • Talent gap still pretty significant (orders of magnitude worse than Silicon Valley, which is not surprising) although there is thirst for learning and a no lack of young people who are not afraid to work very hard
  • Mid-Skill workers care more about job protection than innovating and often see change/removing things from their plate as scary – will they lose their job, or not be good at the new thing we need them to do
  • Micromanagement is necessary to make progress – you can’t just email people and expect stuff to get done. There is constant checking in and auditing of people’s work. The level of trust still does not exist at the same level as working with ‘A’ level talent in a place like San Francisco
  • My decision point is between spending my time training, teaching and mentoring in East Africa or or serve this market from abroad (with an already high performing team) and travel back and forth as needed
  • Local:
    • Pros: Close to market – context, people, can really help mentor, market changing fast, partnerships easier
    • Cons: spending time on micromanagement v.s solving hard problems, personal life issues, quality of life
  • Foreign:
    • Pros: Better team quality, valuations, exit options, potential to build global business
    • Cons: not close to customers, coordination overhead, travel burden, missing important things