Investing in Public

In the spirit of “building in public”, I’ll share occasional updates on my angel portfolio here.

Overview

As of December 2024, I’ve angel invested in 37 companies, and my investments have a blended IRR of 24%.

11 companies have had definite outcomes: 1 substantial exit at 40x, 1 okay exit at 6x, 3 exits that each returned ~1x, and 6 failures.

26 companies are “live”. Of these, there are 5 companies that I’m confident will each return at least 10x; there are 6 others that I am pessimistic about; and the jury is out on the remaining 15.

Cohorts

My angel investing career has had several distinct phases. Combining them into a single portfolio isn’t as informative as breaking them into cohorts:

Cohort I: 2014-2017, 9 companies, India-focused
Cohort II: 2019-2021, 14 companies, generalist
Cohort III: 2022-2024, 14 companies, thesis-driven

These cohorts analogize nicely to “traditional” venture fund cycles; they also reflect my evolving investment strategy. Details below.

Cohort I: 2014 to 2017 (India)

I made my first arms-length angel investment in 2014, while running my own startup Quandl. Over the next 3 years I invested in 8 more companies. These were all small cheques into India-based startups, about half direct and half via syndicate. I didn’t follow any systematic strategy for selection or portfolio construction; this was a very ad hoc portfolio.

• Companies: 9
• Cheques: 14
• MOIC: 5.2
• DPI: 4.1
• IRR: 31%

Key learnings: power law outcomes; pay attention to deal mechanics; DPI is more important than MOIC or IRR; avoid uncompensated risk (eg FX).

Cohort II: 2019 to 2021 (global)

Between 2019 and 2021 I wrote 24 cheques into 14 companies, while running Quandl post its acquisition by Nasdaq. These were slightly larger cheques, but with a different geographical focus than cohort I: Canada, the US and Europe. These investments were somewhat ad hoc initially, but got more intentional towards the end.

• Companies: 14
• Cheques: 24
• MOIC: 2.0
• DPI: 0.1
• IRR: 24%

Key learnings: entry price matters; avoid both fomo and value investing; consensus decisions lead to mediocre outcomes.

Cohort III: 2022 to 2024 (global)

Starting in 2022, I became more intentional about angel investing; this coincided with my moving on from Quandl and Nasdaq. I now have a tighter thesis, portfolio model, and dealflow channels.

• Companies: 14
• Cheques: 16
• MOIC: 1.1
• DPI: 0.0
• IRR: 4%

Key learnings: differentiation matters; tech beats hype; reason from first principles; trust your judgement; don’t sweat the J-curve.

Revenue Growth

I like to invest in companies with capital-efficient growth and sound unit economics. Such companies don’t need a lot of follow-on investment; ironically, this means fewer markups and lower “paper” valuations.

In the absence of markups, I sometimes use revenue as a proxy for value creation. Here are some revenue stats for cohorts II and III:

Annual revenue (USD), entry versus today:

• Average: $120k → $1.1M
• Median: $0k → $500k
• Max: $600k → $7M (not the same company)

Companies with more than $1M in ARR: 7 out of 28.
(I’m hopeful / confident that 4 more will join the club in 2025.)

Breakdowns

Here are some other ways to break down my portfolio:

• Geography: 14 Canada, 14 global
• Work style: 18 in-person, 10 remote
• Stage: 15 pre-seed, 13 seed
• Sector: 9 MAD stack, 3 infrastructure, 5 fintech, 4 SaaS, 7 other
• Profile: 36 of 51 founders are “outsiders” (18 of 28 CEOs)

End notes

I invest my own money, and I also lead a small syndicate that coinvests with me. The above figures are all for my personal angel portfolio.

Company marks are based on the latest priced round. I proactively mark down companies where I don’t think prices reflect true valuations; often, all the way to zero.

This is the update for 2024. You can also read older updates: for 2023 and 2022.

None of this is investment advice, nor is it an offer or solicitation to buy or sell securities or anything else.

My Angel Portfolio

Portfolio Notes

🌱 All my investments are at pre-seed or seed stage: very early product with minimal or zero revenue.

💴 I invest my own money. This gives me a very different objective function from many startup investors.

📈 I share my performance in public; see portfolio statistics.

Cohort I: 2014-2017

📺 AdSparx: video advertising tools [EXIT]
🔬 Doxper: digitizing health data
🌐 i2e1: distributed internet for everyone, everywhere [EXIT]
🚛 Locus: last-mile logistics software [EXIT]
👁️ Mad Street Den: computer vision for commerce
💊 Wellthy: digital therapeutics
🏘️ FastFox: platform for real estate brokers [RIP]
🧰 Qyk: marketplace for local services [RIP]
🍽 TableHero: restaurant management software [RIP]

Currently at 5.2x MOIC, 4.1 DPI, 31% IRR.

Cohort II: 2019-2021

🧠 Daloopa: next-gen financial modelling data
🏢 Mero: vertical SaaS for janitorial services
🌏 Terra.do: climate school and community
🖥️ Setyl: asset and license management platform
🏫 Canopy: data insights for property managers
🏡 BuyProperly: marketplace for fractional assets
🏗️ Citylitics: infrastructure data as a service
🤝 AcuSpire: employment matching platform
💡 Getware: surfacing implicit product insights [RIP]
🚚 Erly: distributed fulfillment network [RIP]
💳 Klanto: spend management platform
💵 Requity: rent-to-own for real estate
🙊 Syro: seamless secret management [RIP]
🎲 TriplePlay: remote culture through games [EXIT]

Currently at 2.0x MOIC, 24% IRR.

Cohort III: 2022-2024

🛒 Arima: privacy-first marketing with synthetic data
📧 Ubico: automation for outreach
🎥 Alchemic: B2B video generation via LLMs
🤖 Quandri: automation for insurance
🤐 Stealth: stealthy mcstealthstartup
🍅 FarmTheory: marketplace for ugly produce
🎼 Composer: AI-powered investing for retail
🏩 Kordie: upskilling the hospitality industry
📞 Productive: an API to the content of your call
🍽️ REMS: data insights for restaurants
🖇️ Paperstack: financial OS for retail brands
🏘️ ResVR: VR design/sales tools for homebuilders
💧 Cascade: modern saas for private credit markets
🎯 Cactivate: self-learning AI marketing agent
🗂️ Dagment: business data done right

Currently at 1.1x MOIC, 4% IRR.

LP Positions

I’m an LP in the following excellent venture funds:

🍷 Uncork: Bay Area, generalist
🌳 Merak: India, deep tech
🤖 GrowX: India, deep tech
🚜 e-squared: NOLA, ag tech

What I Invest In

Stages and Sectors

🌱 I invest at pre-seed and seed stage. I may follow on pro rata in Series A or B rounds, but I rarely write first cheques at those stages. (I sometimes advise later stage companies iff they intersect with my areas of expertise.)

📡 I like B2B companies, including vertical and horizontal software, B2B marketplaces, data and API businesses, platforms & infrastructure, systems of record, unglamorous plumbing, AI/ML tools, and anything involving network effects.

🛍 I generally steer clear of consumer businesses, D2C ecommerce, healthcare, gaming, real estate, seed hedge funds, silicon, security, cannabis and crypto. You’re welcome to pitch me if your startup falls in those categories, but I’m very unlikely to invest.

⚛️ I’m building competence in energy, space, bio, and other deeptech, especially where mediated by software and data. I welcome pitches in those areas, even though I may not be ready to invest.

🚀 I like to see genuine technological innovation. Solving hard problems is a valuable moat.

All these criteria are flexible for the right team in the right market with the right approach. If in doubt, pitch me!

Investment Philosophy

🔮 At the highest level, I invest in startups that are building a future I want to be part of, and I try to help them make that future a reality. Beyond that, there are no rules.

🔥 Team ability and macro tailwinds matter a lot to me. Big ideas, market pull and innovative tech are also important. Traction is a useful proxy; it validates these attributes.

🌎 I’m flexible on geography, industry, and business model. I prefer B2B to consumer. About half my portfolio is in Canada, and half outside it.

🐶 I like both overdogs with earned unfair advantages, and underdogs who are scrappy, resilient, resourceful. I invest in both ‘brave new world’ startups and ‘faster better cheaper’ startups.

❤️ Building a startup is hard. I seek founders of character: resourceful, resilient, optimistic, curious, ambitious, competitive, and committed. If this is you, please reach out!

How To Pitch Me

Guidelines

My goal with these guidelines is to save time for me and you:

• The best way to contact me is email: at@abrahamthomas.info

• I welcome cold emails! No need for a warm intro.

• Don’t send me text, LinkedIn, WhatsApp or Twitter messages; I may not respond. (And if I do, it will only be to ask that you move the conversation over to email.)

• Send me a brief message along with a deck or memo. No need to ask permission to send a deck.

• Your message should include the following baseline info: what the company does; founder background(s); company stage and traction; how much you’re raising; and at what valuation.

• If you have a secret or special insight into your market, unique expertise, or intriguing early signals of market pull / product validation, please mention them!

• I don’t sign NDAs, so please don’t ask.

• I treat founders with respect, and I ask that you reciprocate.

Process

I try to reach investment decisions using no more than 2 meetings and 2 weeks of calendar time, with the following steps:

• You email me your deck, including the baseline info specified above.

• I pass, or I send you 3-5 preliminary questions to gauge if this is a fit. The goal is to avoid wasting time for either of us.

• We do an intro meeting, in which you describe the vision, product, market, company, team, traction, tech, and macro trends (why now?).

• I pass, or I send you 10-12 deep-dive questions that examine the business more closely.

• We do a deep-dive meeting during which you answer these questions. (Or you can answer them by email if you prefer).

• I pass, or I commit to invest, and you accept using the YC handshake protocol.

Despite my best efforts, sometimes things slip; if I seem to drop the ball, please send me a nudge. Also, please send calendar invites with links or locations for all meetings.

Passing

My philosophy on passing:

• I don’t believe in “retaining optionality”. If I don’t plan to invest, I will let you know, explicitly.

• I invest in fewer than 1% of the companies I see, so please don’t take it personally if I don’t invest in yours.

• I try to provide thoughtful and actionable feedback on why I passed to all founders who I have at least a phone call with.

• Sometimes there may be a great company doing everything right that just isn’t a fit for me.

• I’m happy to stay in touch with companies I’ve passed on; feel free to add me to your update email list.

• Don’t ask me to introduce you to other investors if I’ve passed on your company; it’s not a good signal and won’t help you.

Founder Testimonials

• “Abraham is willing and able to provide advice that can be the tipping point for those difficult founder decisions. The nuance and detail that incorporates your unique business situation, the current market, and his own personal experiences is offered with swift confidence, which is the ultimate secret weapon for any founder.”

• “Abraham is a great investor to work with. He’s highly professional and always available for help. For anyone looking for capital, Abraham is an excellent addition to have on their cap table”

• “Abraham is a true asset. His wealth of knowledge on all aspects of growing a business, especially data businesses, combined with his tactical and on-point advice, has been instrumental in helping us scale and achieve success. Whether it’s raising capital, strengthening the business model, or executing on a growth strategy, Abraham always has valuable insights to share.”

• “Abraham has been our most responsive and helpful investor. He responds thoughtfully to every update, question and ask that we have, and takes the necessary action to make a positive impact on our business.”

• “When I have a hard problem, I call Abraham. He’s experienced the same challenges first hand and survived. He truly puts the time and effort to making sure the founders he works with are successful.”

• “Working with Abraham has been a journey of candid, thoughtful strategic advice. As a founder himself, Abraham empathizes with the ups and downs in running a company. We turn to him constantly at times of our most difficult decisions and lean on his experience. He is always genuine and spends an outsized amount of time and effort with us.”

• “A world class teacher for go to market, hiring, fundraising and messaging. He’s been great at both diving into the details as well as thinking about the long term strategic view. Any B2B founder would benefit greatly from working with him.”

• “We have been extremely lucky to have found Abraham as an early angel investor in our company. He’s been with us from right at the beginning and has consistently provided absolutely on-point advice at each stage, in the most hyper rational way which has been a massive assistance against the extreme highs and lows of running an early stage business. I’ve not only recommended, but actively encouraged other founders to work with Abraham as he brings so much more than just an investment.”

• “[Abraham is] my go-to person for guidance on analytical and technical questions, as well as the best way to express my vision and mission. He’s a rare combination of pure intellectual horsepower, and the ability to succinctly yet eloquently communicate ideas and data.”

Why Work With Me

Guiding Principles

I aim to be an investor who founders trust and can rely on. This means:

• Support: I’m a resource for you beyond just my dollars.
• Expertise: I’m happy to share any knowledge I have.
• Low ego: I help if I can, and get out of the way if I can’t.
• High trust: I act with integrity and professionalism.
• Respect for your time: Quick responses and minimal friction.
• Alignment: No zero-sum games; I win when you win.
• Empathy: I’ve been there, done that – and I’m on your side.

Read my testimonials to see what my portfolio founders have to say about me.

Ways I Can Help

My secret sauce is that I spent a decade as the founder of a successful tech startup; but before that I spent another decade as a professional investor at a large hedge fund. I think this combination is pretty unique, and it lets me help you more effectively.

🎯 Tactics

My founder experience helps you tactically: on go-to-market, on positioning and story-telling; on data and API strategy; on culture and recruiting; and perhaps most important, with alignment and empathy. I’ve worn lots of different hats as a founder; as a result I can help on almost all operational aspects of early-stage startups. Here are some examples:

• Go-To-Market: A great product won’t change the world unless it’s matched with great distribution. And modern distribution is complex: inbound, outbound, bottom-up, top-down, pincer, product-driven, sales-driven, community-driven, channel-driven, hybrid – there are so many interacting options. I can help you navigate them.

• Data and API Strategy: I know the modern data ecosystem well, and can help on almost every aspect of data in your organization: business and commercial strategy, infrastructure and technical choices, benefits and limitations of data, building effective data teams, and more.

• Network Effects: Network effects businesses are hard to start, but extremely powerful at scale. As the founder of a saas-enabled marketplace with multiple overlapping network effects, I have a lot of insight into the nuances of building and scaling such businesses.

• Resources and community: I write regular memos for my portfolio founders, covering important market and macro trends, tactical and strategic tips, functional resources, and more; they tend to be more concrete and actionable than most “startup advice”. My founders also form a supportive and friendly community that I foster.

• Empathy: Being a founder is hard. As a founder who has been through the venture-backed journey myself, from inception to exit, I believe I can be more aligned, more insightful, and more empathetic about the challenges you face than most investors without that experience.

🌎 Strategy

My investing experience helps you strategically: on resource allocation and business planning; on financing and downstream investors; on competition, moats and ecosystem; on what it takes to win in the long term. Here are some examples:

• Resource Allocation: Balancing growth rates and burn rates, team size and team speed; retaining optionality while seizing opportunity; and ultimately, maximizing your risk-adjusted expected value: resource allocation is central to the CEO’s job, and I can help you think systematically and rigorously through it.

• Financing: I’ve raised lots of venture capital, and advised founders who’ve raised lots more. I can help with: deciding when and why and how much to raise; building a powerful pitch (and the company to support it); executing a disciplined and effective fund-raising process; negotiating terms; and closing the deal.

• Introductions: I can help with introductions and references for potential customers, partners, job candidates, expert operators, and down-stream investors. Specifically, I can provide warm intros to partners at many well-known VC firms, from seed to Series B, across the USA, Canada and India.

• Story-Telling: The ability to craft a compelling narrative – for customers, for partners, for investors, for employees, for the press – is an essential part of the founder’s toolkit, and it’s something I have a lot of experience with. Category creation is an especial strength.

• Recruiting and Culture: The team you build is the company you build. To attract and retain and empower and scale a truly world-class team is perhaps the biggest challenge for founders today. Creating a strong, sustainable, high-performance, happy culture is the key to solving this challenge, and it’s something I pride myself on.

• Macro: Businesses are not built in a vacuum. Successful founders need to understand the macro environment; economic cycles and the cost of capital; business model evolution; customer, partner and investor dynamics; and more – and this is truer than ever in 2023.