2025 in Review: Patterns From 50 Investments

Year two of angel investing: 456 new conversations, 25 new investments, early patterns emerging

In 2025, I maintained similar deal flow to last year, investing in about 5% of companies I met. The portfolio is showing early signs of power law dynamics: top 5 companies drive 79% of revenue, with 7 companies hitting $1m+ ARR. Key lessons: vertical solutions outperform horizontal tools, and the best founders are technical people solving problems they’ve lived. Looking ahead, I’m increasingly excited about robotics and space as potential areas to work in once my kids are older. Let’s break this down in more detail.

Meetings & Investments

This year, I talked with 456 startups and invested in 25, or about 5%. That’s roughly the same conversion rate as last year. I didn’t do any token investments in 2025.

Portfolio Performance

Two years into investing, my portfolio shows clear power law dynamics. The companies have generated almost $26m in total revenue, but it’s heavily concentrated: the top 5 represent 79% of revenue, and the top 10 represent 91%. Seven companies crossed $1m in annual revenue. Two more will hit that milestone in the next few months.

Growth by Company Age

The portfolio shows a predictable pattern by company age: The youngest companies (under 12 months) grow fastest at 12% monthly, but from small bases: $226K average revenue. Companies over 24 months old grow slower monthly, but from $1.35M+ bases. The middle cohort (12-24 months) generates 53% of total portfolio revenue. This is when companies find product-market fit and revenue accelerates.

The $10M Milestone

Looking at the $10m revenue milestone: several companies are on track to hit it. Here’s the breakdown by probability:

Fundraising Environment

Follow-on fundraising has been relatively quiet: only one portfolio company raised a follow-on (Toma from a16z), and some opted for quick raise from existing investors. Most companies have 2+ years of runway. A few are planning to raise in early 2026.

What’s Working

What’s working for the top performers:

• Fast-moving markets. Two companies are riding the data center buildout and voice AI wave.

• Large contracts. One healthcare company scaled quickly after landing enterprise deals.

• Content at scale. A B2C company built a content operation that drives consistent revenue.

Pivots and Patterns

Seven companies have pivoted. Three pivots are working (so far). Pivoting deserves its own analysis: when to stop, how founders maintain conviction, where they find new ideas. I’ll write about that separately.

Other patterns:

• The best founders are technical and have lived the problem they’re solving. Pedigree matters less than I expected.

• Failed investments show similar warning signs: founder goes dark for 3+ months, growth stays under $10K monthly after a year, or the company hits 24 months with under $200K ARR

• Only one horizontal tool cracked my top 10 by revenue. Winners are vertical: specific problems in large industries.

Helping Founders

Few founders ask for help proactively. Some include asks in monthly updates, which works well sometimes. But I wonder if I’m missing opportunities to be more useful: founders might not know what I could help with.

Looking Ahead

Two sectors excite me enough that I’d consider operating in them: robotics and space. I’ve made small investments in both (2 robotics, 1 space), but these require larger checks than I typically write. The timelines are long: a decade for robotics to mature, longer for space. But the potential is enormous. Not now, I have a second child coming. But in a few years, if the right opportunity emerges, I’d jump in. I’ll keep angel investing either way.

2025 reinforced that angel investing is a patience game: power laws take time to materialize, but the early signals are encouraging. The best companies are solving real problems in fast-moving markets with technical founders who’ve lived the pain. While I’ll keep investing through 2026-2027, I’m increasingly drawn to robotics and space as areas where I might eventually build rather than just invest. If you’re working on something ambitious, reach out, I am happy to chat.