2024 in Review: From 393 Conversations to 25 Investments

First year doing angel work

My investing journey started in 2022, mainly backing early NEAR ecosystem projects rather than chasing returns. This accidental start led to some wins - Hot Protocol, Meteor, and Carv all became notable successes.

In early 2024, I turned angel investing into my primary focus. I set an initial target to meet with 230 startups that year - starting with 10 conversations in January and ramping up to 20 per month. I exceeded this goal significantly, speaking with 393 startups and investing in 25 of them. While I'd planned to build a portfolio of 50 startups over three years, I'll hit this milestone in just two. Most of my investments were in traditional tech (you can see all of them here), with only two in web3 - Fraction and Rift, both performing well.

How I Found Startups

Most of my deal flow came from direct outreach (61%). My team and I searched LinkedIn weekly for promising startups and contacted founders directly. The rest came through referrals (24%), my existing network (8%), inbound inquiries (6%), and events (1%). Despite my web3 background since 2018, and getting many leads from that ecosystem, I ended up investing primarily outside of it. Good leads don't always make good investments.

How I Pick Investments

My investment criteria evolved this year. While I still value traction and strong founders, I've put more emphasis on market understanding (read more on this here).

Token deals offer faster liquidity and non-dilutive funding compared to equity. But despite these advantages, I've heavily favored equity investments. Why? The founder quality gap is significant - while 20% of my conversations were token deals, they made up only 8% of my investments.

What I Look For:

• Founders who see their startup as a life mission

• Teams that work well together

• Deep market understanding

• Early revenue traction

• Strong technical talent

Red Flags:

• Indifference toward angel relationships

• Years of activity with little progress

• Recent pivots without market knowledge

• Technical founders reluctant to sell

• Treating startups as resume builders

Competition for deals wasn't an issue - only once did I face an oversubscribed round, which I passed on when offered just 20% of my usual check size.

Portfolio Management

I track my startups' monthly metrics systematically. YC founders excel at regular investor updates - it's built into their DNA. Non-YC founders often lack this habit, which can be problematic. Radio silence usually breaks only when things get desperate.

My support typically focuses on three areas (which come down to network):

• Fundraising connections

• Recruiting help

• Customer introductions

I meet founders in person every few months and stay available through email and text. But it's up to them to leverage my help.

Key Portfolio Insights:

• The power law is real - a few companies grow explosively while most iterate slowly

• Pivots, big and small, can transform outcomes

• Starting a niche is smart, but some niches prove too small

• For AI startups, the real competition is often DIY solutions using off-the-shelf tools

• Co-founder conflicts remain a major startup killer - I learned this firsthand when my own startup failed in 2014

2025 Outlook

I'm cautiously optimistic about my portfolio. While I'll continue focusing on equity deals, I plan to add more token investments to improve portfolio liquidity. But I won't go heavy on tokens - I'm an investor, not a trader.

My Tech Stack:

• Airtable - Startup and contact database

• Otter - Meeting transcription (exploring Granola as an alternative)

• AI Models - Content creation and call analysis

  • Llama

  • Claude

  • OpenAI's O1 (via Poe)

• Google Docs - Weekly planning

• Next up: Building AI automation for deal flow management and founder communications.

Time Management and What's Next

I work intensely but more sustainably than in my early NEAR days or when I first came to the US. Between angel investing, family life with my toddler, and staying active (swimming, rock climbing, mountain biking), my schedule is about 70-80% full.

This leaves me with meaningful free time. I've filled it with reading, my lifelong habit, but I'm exploring new ways to use these hours in 2025.

One area that interests me is San Francisco's future. While the city faces challenges, I'm optimistic about its long-term recovery, even if it takes 5-10 years.

If you want to chat, submit your startup here. Happy Holidays!