Angel Investing - A Toolkit 🧰

Part 1 - Education (updated June 2021 with new content)

This toolkit is designed for sophisticated investors with previous investment experience in public companies and/or a couple of existing angel investments looking to learn more. Hobby investors (like me) will likely get the most value out of it, but I’m hoping some professional Angels will also use it. Please add any suggestions or questions in the comments or add me on twitter. If you’re interested in hearing more from me on Angel Investing or operating startups add yourself to my email list.

New June 2021 Content at the bottom

Credit: Brendan Rawlings

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Background

I am a Founder first and foremost of a Series C stage company: Velocity Black.

I have been investing as a hobby for the past 7 years on weekends and had my first successful exit in 2019 when one of my first investments, Syft, was acquired by Indeed, returning >25x in a four year period (and changing my life in the process). I started investing as I am truly fascinated by business and wanted to learn more about other early stage technology companies, to help me grow my own business.

Over those 7 years I have built up a list of educational tools, deal flow networks and models for analysing businesses. The startup and investor eco-system has been very generous to me. A small way for me to return that generosity is to share this list of resources back with the investor community.

Education 🎓

Risk comes from not knowing what you’re doing. — Warren Buffett

There is some luck involved in early-stage investing, particularly when you’re just getting started. However there is a lot to learn to help avoid the pitfalls that other investors, including me, have only learned through experience. As Benjamin Franklin said: an investment in education always pays the highest returns.

The best way to invest your time if you are new to Angel Investing is to bury yourself in the widely available and mostly free online educational resources on Angel Investing and the startup eco-system. I have summarised some of these below and have also highlighted the top in each category if you’re short on time.

People 🧑‍🤝‍🧑

Follow these people on Twitter, Medium and Clubhouse. I have personally learned more from following and interacting with these people on social media, than I have from any course or book, which is why I put this section first. There are 24 people below, I do suggest reading about each as some may be more useful to you than others depending on your interests. However in order to save you time, I also created a list so you can follow them all in a couple of taps here.

Top 3:

Jason Calacanis — Jcal is on the road to becoming the GOAT Angel Investor. Early investor in Uber, Robinhood, Calm and many other companies which became unicorns. What I love about jason is his commitment to not only investing in and helping early stage companies, but also to sharing his ideas, deal flow and investment advice with aspiring angels around the world (while also getting his own beak wet). Jason is a content machine and without a doubt one of the hardest working angel investors in the world (as evidenced by links to his content below).

Harry Stebbings — Harry Stebbings runs one of the most widely listened to podcasts in the startup funding community, 20 Minute VC, which he started when he was a teenager. Off the back of its success he is also now a partner in two venture funds he helped start… and still only 23 years old. Harry is probably the best connected person in the VC community and therefore his tweets and podcast are a good insight into trends and what professional investors are talking about.

Mac Conwell — McKeever Conwell’s ideas, optimism and mission are a breath of fresh air in a world of investors who tend to act like sheep. Mac stands apart from the herd, offering contrarian views and also interesting insights into Gen Z led startups and companies led by under-represented founders.

Others I learn from (in no particular order):

Shakil Khan- Shakil Khan (Shak) is the most notable and one of the most prolific London-based Angel investors with a portfolio includingSpotify and CoinDesk. He’s recently Co-Founded a new venture fund with Daniel Ek— Prima Materia.

Li Jin- one of the trailblazer investors in the creator economy (or passion economy), alumni of Andreessen Horowitz and managing partner of a new fundAtelier. Also the only early stage venture fund I see featured in TikToks. A rising star.

Nick Telson- Another Brit, former founder (DesignMyNight) and now angel investor and podcast host. Nick Telson is one of the most active angels in London at the moment, his podcast (see below) is also very useful listening for understanding how angel investors analyse businesses.

Lolita Taub- Lolita is a general partner at The Community Fund, focussing on ‘underestimated’ founders. She is very founder focussed in her content, but I have found valuable nuggets of gold for angel investment.

Elizabeth Yin- Elizabeth focusses on ‘hilariously early founders’ through Hustle Fund. Interesting as one of the few funds and therefore VCs focussed on the very earliest stage of startups — Pre-Seed, typically a stage where Angels are also investing.

Paul Graham- Founder of Y-Combinator, the most successful startup accelerator and community in the world.

Andrew Wilkinson- Former founder and now runs Tiny — a holding company which acquires early stage businesses, considered the Berkshire Hathaway of the startup world. Andrew Wilkinson is thoughtful and is also generous in the level of information he shares about how he analyses and invests in businesses.

Eileen Burbidge- Eileen is the founder of Passion Capital and an early-stage investor based in London. She was one of the first investors in Monzo and Duedil.

Shaan Puri- Former founder (exited to Twitch) and now investor. Shaan Puri is interesting to follow as he freely gives away lots of new business ideas.

Sahil Bloom- Investor and prolific content creator. Sahil has that rare ability of breaking down complex ideas in business and finance to make them simple, relatable and actionable.

Lenny Rachitsky- Lenny is an angel investor and writes one of the more popular startup newsletters. Interesting content on creator economy and growing early stage businesses.

Frank Rotman- fintech focussed investor who shares a lot of ideas on twitter around Fintech. Frank Rotman also shares insights from LPs in venture funds and content around exit valuations.

Romeen Sheth- Romeen is a founder, angel investor and host of one of the most interesting startup investment podcasts (see below). He shares a tonne of interesting insights, and particularly on bootstrapping on his twitter.

Garry Tan- Garry Tan is the founder of Initialized Capital who focus on pre-product market fit companies. Garry is also a prolific content creator and sharer.

Landon Ainge- Landon shares a similar passion to me for democratising access to equity investing. Runs an interesting Syndicate (which will go deeper into in Part 2 — Deal Flow).

Mike Maples Jr.- Mike hosts a great podcast (below) with unique insights into the earleist stages of some of the most successful companies in the world. He’s also a partner at Floodgate.

Anne Lee Skates- Partner at Andreessen Horowitz, Anne has great insights on social startups and some emerging technologies.

Sahil Lavingia- Former founder (and still running) Gumroad— a company which has become particularly interesting with the emerging creator economy. Sahil was one of the first to utilise AngelList’s rolling, managed fund model to raise $10m from his twitter followers per year for a fund in a matter of days (or so it seemed). Sahil’sposton his journey as a founder is an uncompromising and rare opening of the door into a startup journey. A useful reminder that the startup ride is a roller-coaster with as many downs as ups, and not just the glitzy Techcrunch funding headlines you read.

Zach Coelius- four-time former founder, and similar to Sahil, has now launched a rolling-fund. Zach’s no-nonsense approach to investing and interacting with founders is refreshing, best exemplified in his ‘user manual’. In a world where so many investors waste your time or give feedback in jargon, any Founder can appreciate Zach’s approach. (reminds me to write my own user manual).

Sam Altman- entrepreneur, investor and blogger. 

Sam is former President of Y Combinator and currently CEO of OpenAI. His historic blog posts are well worth a read.

Naval Ravikant- Last, but by no means least, for those questioning if I were about to leave out the Godfather, you shall not be disappointed. Naval founded AngelList which we will come onto in more detail in Part 2. His insights are unique and his twitter feed will deliver the tech world equivalent of Dalai Lama-level philosophy directly into your brain.

Courses 🏫

While I have listed many below, I have only completed one course- Angel University. I primarily did this to build a network with other angels, rather than for the content itself. It was useful for this purpose and has helped sourcing interesting new deal flow. I have researched reviews and curriculums of the others however, which are all useful to varying degrees.

Top recommendation:

Angel University- This is a short, 3 hour course designed and hosted by Jason Calacanis. It costs $300 at the moment. You will get a chance to pose questions to Jason and the other host and will also come away from it with some basic portfolio management tools. The real value is the network of other angels on the course and the subsequent deal flow that they can generate.

Others:

Angel Course- founded by Mesh Lakhani, and now free. An endorsement from Naval Ravikant on the home page is probably all you need to know about the quality of this course.

Classrebel- founded by Brooke Harley and affordable at $50 — unique as you can always rejoin live classes again in the future and have access to on-demand content.

Rebel One Ventures- VC & Angel intensive. This is a high quality course from Sergio Marrero with direct access to top venture investors and angels included in the course. If you are looking to become a professional angel or full-time investor, this may be the course for you, but it comes at a price of $4,999. (They also have a taster course for $199 which is just one of the modules of the larger course — start there if you’re in doubt).

Kauffman Fellowship- if you’re looking to skip the whole angel investing part and start your own VC fund, or simply want to build a network with the most respected VCs in the world, this may be the course for you. It’s a two year course led by Jeff Harbachand costs $80,000.

Angel Capital Association- Angel University course from the ACA in the US. This course is more comprehensive than Jason’s, with many more modules which are longer in length. It is more expensive as a whole ($1k+) but you can take and pay for individual modules, so this is potentially a good resource for those looking to brush up on a particular area.

Angel Investing School (AIS)- UK focussed angel investing school — £495 founder by Andy Ayim. They also have a free dictionary for those trying to get to terms with angel investing and startup lingo.

UK Business Angel Association- UK focussed course for business angels — £499. The curriculum seems comprehensive with video content and testing.

Angel Investment Network- A short free collection of articles guiding first time angels through The Basics (What, Why, UK Tax Breaks), Picking Winners (Deal Flow, Evaluation, Due Diligence) and Closing Deals (Docs, Negotiation).

Podcasts 🎧

I find Founders and Investors open-up more in the heat of the moment in the podcast booth, than they otherwise would with the written word, and therefore the content can be more authentic.

Top 3:

This Week In Startups (TWIST)- another jason publication? Yes. Full of founder and investor interviews, well edited so as not to waste your time, this should be near the top of your list. What’s more due to Jason’s Terminator-esque work ethic, there’s a back catalog of 1176 episodes at the time of writing to sink your teeth into. Favourite recent episode is withZach Coelius— E1772.

Pitch Deck- from Nick Telson. What makes Pitch Deck unique is the great format. You hear pitches from entrepreneurs who are actually raising, you hear Q&A from experienced Angels and finally you get some analysis of the business once the entrepreneur has left the pitch studio. Favourite episode is #18 with Chris Smith (who is a Kauffman Fellow) from Playfair Capital. You can also hear yours truly in episode #14.

20 Minute VC- Do not let the name fool you, what may have started as 20 minute podcasts has now elongated to satiate the demand for more Harry. Harry has assembled a who’s who of the Founder, Angel and VC community. Great learning ground.

Others:

Starting Greatness- from Mike Maples, Jr. and a relatively new addition. A stellar line-up of guests including legendary founders and investors like Marc Andreessen,cReid Hoffman and Keith Rabois

has helped this podcast become a staple.

Square One: Conversations with the Best in the Business- hosted by Romeen Sheth — an eclectic mix of founders and investors. Romeen goes deep on the subject matter. Favourite episode: #79 with

Jonathan Hsu from Tribe Capital where he talks a little about theMagic 8 Ball methodfor analysing startups.

The Pitch- from Gimlet Media and hosted by Josh Muccio. A US based podcast with real entrepreneurs pitching for real money. My favourite episode is on Disrupting Venture Capital (from November 2020).

Playing With Unicorns- with an angel who might vie one day for the GOAT record with Jason — Fabrice Grinda.

ALL-IN- while this is not as ‘investing-centric’ as those above, this is without a doubt my favourite podcast at the moment. With jason, Chamath Palihapitiya, David Sacks and David Friedberg. 4 of the best investors/founders in the world, you feel like you’re sitting at the poker table with a bunch of friends chatting sh*t.

Books 📚

The shortest section of the toolkit, but all below are highly recommended and read by me.

Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist- written by two legends Brad Feld and Jason Mendelson. I would say this is likely more useful for entrepreneurs than angels, but a great starting place to understand how venture investment work.

Angel Investing- by David Rose is a great place to start reading on Angel Investing. Foreword by Reid Hoffman.

Angel-How To Invest in Technology Startups- by Jason Calacanis. Say no more. Read it, listen to it, pray with it.

The Investing King- useful for both angels and entrepreneurs, written by Ross Blankenship.

Startup Wealth- by Joshua Maher— great as Josh gets the perspective of many of the best investors in the business in his book.

Newsletters & Blogs 🗞️

Newsletters are a great way of staying on top of the latest trends, fads and keeping a constant stream of learning coming in to your inbox without having to go out and search for it.

Top 3 Recommendations::

The Odin Times- free- by Patrick Ryan, interesting thoughts and insights on European Tech in particular. Recent post on Pre-Seed is worth a read.

How to be an Angel Investor - by Paul Graham - an oldie, but a goodie. The original essay and resource on getting into Angel Investing. I find it interesting how the core of this post despite being 11 years old, is still relevant in today’s investing landscape. Naval then created a follow-on presentation to this called 'part 2’ which I have managed to find a transcript of here (not to be confused with the two parts by Naval below, which are more in depth and recent).

How To Angel Invest Part 1 & Part 2 by Naval - Expansive blog posts / talks on Angel investing from Naval Ravikant.

Others:

AVC — free- from Fred Wilson long-time VC — musings on a variety of topics including startups and investing.

Benedict Evans- free & premium options ($100 per year) — this was the first newsletter I signed up for in tech. Former partner at Andreessen and now at Mosaic Ventures, Ben is probably best known for his presentations.

The Generalist- free & premium options($120 per year) — by Mario Gabriele- former venture investor turned writer and community builder. I only just signed up to this one, but it looks very promising and comes highly recommended. In depth analysis.

The Odin Times- free- by Patrick Ryan, interesting thoughts and insights on European Tech in particular. Recent post on Pre-Seed is worth a read.

CB Insights — free — light hearted, mainly focussed on later stage private / early stage public companies, but useful to understand trends in overall funding.

Hunter Walk — free — from Hunter Walk partner at seed stage fund Homebrew.

Elizabeth Yin - free — from Elizabeth per above. More focussed on founder / startup advice, but some good posts which are informative on building VC funds and investing.

Both Sides of The Table — free — from Mark Suster at Upfront Ventures.

Tomasz Tunguz — free — from Tom Tunguz at Redpoint Ventures.

Strictly VC — free — from  Connie Loizos — high quality content on Venture Capital and Startups.

Clubhouse Clubs🎙️

I’m still getting used to Clubhouse and its potential having only joined in December. One of the challenges in finding your home in a new community is filtering through the less valuable clubs and rooms. I’ve highlighted a few of my favourites so far below, if you follow/join them you’re likely to find yourself a part of more interesting conversations.

Invest

VC & Angel Investor Club

The European Tech Club

Impact Investment Club

European Tech Entrepreneurship

Startup Club

Good Time

June 2021 New Content 💥

Thanks to those that reached out with suggestions for content to add, which I’ve listed below.

VC Academy - a course highlighted to me by Aarish Shah. I haven’t taken this course, but it seems a like a good route into either getting a job in VC, making your first Angel investment or starting a fund.

Lessons from Investing - with Charlie Songhurst is a solid podcast on investing with lessons from Charlie’s experience in investing in more than 400 companies. Full of unique insights I have not heard from Angel investors.

Spearhead - is an an interesting initiative by Naval to help turn founders into investors. Their blog and twitter feed have many interesting snippets of advice for angel investing.

Thank you for reading. Remember the education never ends, so I appreciate any additions in the comments to help me and future users of the toolkit. If you are interested in hearing more from me sign up to my email list.

Continue to: Angel Investing Toolkit Part 2 - Deal Flow