Angel investor · San Francisco, United States
Recorded investments.
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of dated first investments
were at Angel, Pre-Seed or Seed
One dot = one company at first recorded investment.
Written insights from the recorded portfolio, with the evidence linked below.
Drew Houston has dated investments in 19 companies. 6 first entries were at Angel, Pre-Seed or Seed (31.6%). An early-stage founder can use the sector and stage filters to find comparable companies before approaching the investor.
Explore the evidence ↗2 first company relationships appear in the latest 24 months, compared with 6 in the preceding window. The latest recorded investment is 2025-07-28. This describes observed activity through 2026-05-22; it does not establish current availability.
Explore the evidence ↗9 of 17 companies with a full 24-month observation window raised another equity round. This investor backed 1 of those companies again within that window. The difference is a reason to research the wider syndicate, rather than assume the same investor will fund the next round.
Explore the evidence ↗Artificial Intelligence is the largest displayed sector by company count, appearing in 6 portfolio companies; sector tags overlap. 0 first entries carry a recorded lead flag and the median first-round syndicate includes 6 other named backers. Shared rounds are evidence of co-investment, not evidence of an introduction route.
Explore the evidence ↗Start with observed behavior.
Every rate has a defined denominator.
25th–75th percentile across 19 disclosed first rounds. Total round size; the investor’s own cheque is undisclosed.
Size your round ↗22 May 2024–22 May 2026, versus 6 in the preceding 24 months.
See the rhythm ↗9 of 17 companies with a full observation window. The next round can include any investor.
Follow the path ↗1 of the same 17 companies. Build a financing plan around the wider investor market.
Explore co-investors ↗Choose your sector and stage to find
companies he first backed in that space.
A match means a recorded investment in this category. It does not establish current interest or availability.
All sectors · All entry stages. Round amounts are total financing, in USD.
AI and cloud based solutions for product monitoring and management
$5.0M total first roundProvider of text-to-animation platform to animate characters for various projects
$5.6M total first roundAI-powered LLM platform for enterprise software development
$25M total first round| Sector | Seed | Series A | Series B | All stages |
|---|---|---|---|---|
| Artificial Intelligence | 6 | |||
| AI Infrastructure | 3 | |||
| HealthTech | 3 | |||
| Healthcare IT | 2 | |||
| HRTech | 2 | |||
| Product Management Tools | 1 | |||
| 3D Animation | 1 |
Use stage-specific financing ranges
to frame the size of your syndicate.
Logarithmic scale. A dot marks the median; the band spans the 25th–75th percentiles. These are entire rounds, not individual cheques.
A subsequent round and repeat backing
answer different fundraising questions.
Includes first investments on or before 22 May 2024. 2 newer companies and 1 undated histories are excluded. Follow-up stops at the dataset’s latest round on 22 May 2026. These observations do not measure returns or predict a company’s outcome.
| First stage | Eligible companies | Next round ≤24 mo | Same investor again ≤24 mo |
|---|---|---|---|
| Seed | 4 | 2 / 4 | 0 / 4 |
| Series A | 8 | 4 / 8 | 1 / 8 |
| Series B | 4 | 3 / 4 | 0 / 4 |
| Series C | 1 | 0 / 1 | 0 / 1 |
Separate first investments from later
rounds in companies already backed.
*2026 is partial, through 22 May. Bar height counts first investments + repeat rounds; earlier years are complete calendar periods in this dataset.
Frequent shared rounds suggest a place
to investigate sector and stage alignment.
3 shared rounds · 2 companies
Latest shared round Aug 20182 shared rounds · 2 companies
Latest shared round Jun 20242 shared rounds · 2 companies
Latest shared round Jun 2022Shared rounds establish recorded co-investment. They do not establish a personal connection, introduction route, or current willingness to invest.
First investment comes first.
Amounts refer to that entry round.
| Company | First backed | Entry stage | Total entry round | Same investor again? |
|---|---|---|---|---|
Player Zero ↗Atlanta | Jul 2025 | Seed | $5.0M | No later round recorded |
Cartwheel ↗New York City | Jun 2024 | Seed | $5.6M | No later round recorded |
Lamini ↗Palo Alto | May 2024 | Series A | $25M | No later round recorded |
Speak ↗San Francisco | Aug 2023 | Series B | $16M | No later round recorded |
| Aug 2023 | Series B | $16M | No later round recorded | |
Imbue ↗San Francisco | Oct 2022 | Series B | $20M | No later round recorded |
Regard ↗Los Angeles | Jun 2022 | Series A | $15M | No later round recorded |
| Jun 2022 | Series A | $15M | No later round recorded | |
Certa ↗Saratoga | Mar 2022 | Series A | $15M | No later round recorded |
Journey Colab ↗San Francisco | Sep 2021 | Series A | $12M | No later round recorded |
Superhuman ↗San Francisco | Aug 2021 | Series C | $75M | No later round recorded |
Twingate ↗Redwood City | Oct 2020 | Series A | $17M | No later round recorded |
Balsa ↗San Francisco | Oct 2020 | Seed | $4.5M | No later round recorded |
100 Thieves ↗Los Angeles | Jul 2019 | Series B | $35M | No later round recorded |
Simple Habit ↗San Francisco | May 2017 | Seed | $2.5M | No later round recorded |
Scale AI ↗San Francisco | May 2017 | Series A | $4.5M | Yes · Aug 2018 |
Convoy ↗Seattle | Oct 2015 | Seed | $2.5M | No later round recorded |
Triplebyte ↗San Francisco | Sep 2015 | Seed | $3.0M | No later round recorded |
Color ↗Burlingame | Apr 2015 | Series A | $15M | No later round recorded |
No companies match these filters. Try a broader sector or stage.
Kept in the 20-company portfolio; excluded from entry-timing calculations.
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