INVESTOR NOTES / 001ANGEL INVESTOR / ,
KNOW THE INVESTOR. SHARPEN THE PITCH.

Angel investor ·

Kevin Oleary.

Recorded investments.
A clearer sense of fit.

Find where your company fits, how rounds are assembled, and what happened after the first investment.

THE ENTRY PATTERN2012–2026
100%

of dated first investments
were at Angel, Pre-Seed or Seed

First investment stage across 23 companies1 Seed, 22 Angel and 0 other-stage entries. Each dot represents one company.
Seed 1Angel 22Other 0

One dot = one company at first recorded investment.

23 companies · 23 recorded equity rounds
Dataset’s latest round 22 May 2026/Latest recorded investment 26 Aug 2025
THE FOUNDER’S BRIEF

Read the pattern before the pitch.

Written insights from the recorded portfolio, with the evidence linked below.

01

Start with the first entry

Kevin Oleary has dated investments in 23 companies. 23 first entries were at Angel, Pre-Seed or Seed (100.0%). An early-stage founder can use the sector and stage filters to find comparable companies before approaching the investor.

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02

Separate activity from reputation

4 first company relationships appear in the latest 24 months, compared with 9 in the preceding window. The latest recorded investment is 2025-08-26. This describes observed activity through 2026-05-22; it does not establish current availability.

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03

Plan the next financing step

2 of 19 companies with a full 24-month observation window raised another equity round. This investor backed 0 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.

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04

Use a specific point of relevance

B2C E-Commerce 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 0 other named backers. Shared rounds are evidence of co-investment, not evidence of an introduction route.

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01 / THE READOUT

Four signals before you pitch.

Start with observed behavior.
Every rate has a defined denominator.

01 — ROUND CONTEXT
$131K–$400K

The middle half of entry rounds

25th–75th percentile across 22 disclosed first rounds. Total round size; the investor’s own cheque is undisclosed.

Size your round ↗
02 — NEW RELATIONSHIPS
4companies

First investments in the last 24 months

22 May 2024–22 May 2026, versus 9 in the preceding 24 months.

See the rhythm ↗
03 — NEXT FINANCING
11%

Another equity round within 24 months

2 of 19 companies with a full observation window. The next round can include any investor.

Follow the path ↗
04 — REPEAT BACKING
0%

This investor invested again within 24 months

0 of the same 19 companies. Build a financing plan around the wider investor market.

Explore co-investors ↗
02 / FIND YOUR FIT

Where does your company sit?

Choose your sector and stage to find
companies he first backed in that space.

YOUR COMPANY

A match means a recorded investment in this category. It does not establish current interest or availability.

23matching companies
$200Kmedian first round (22 disclosed)
4first backed in last 24 months

All sectors · All entry stages. Round amounts are total financing, in USD.

Angel

Chalkless ↗

Manufacturer of grip enhancer designed for various sports and athletic activities

$400K total first round
Angel

VSEAT ↗

Manufacturer of noseless bicycle seats designed for comfort and health

$200K total first round
Seed

Nameberry ↗

Provider of resources for baby names, including trends and meanings

$350K total first round
Explore matching portfolio companies ↓

The sector × stage map

First investments · companies can appear in more than one sector
Number of first investments by sector and entry stage. Select a cell to explore companies.
SectorAngelSeedAll stages
B2C E-Commerce6
HealthTech3
Sports Equipment2
B2C Grocery Delivery2
Online Grocery2
Uber for Grocery Delivery2
Food Tech2
03 / ROUND DESIGN

The round around the investor.

Use stage-specific financing ranges
to frame the size of your syndicate.

First-round size, by entry stage

USD · middle 50% and median
Angel21 disclosed
$200K$125K–$400K
Seed1 disclosed
$350K$350K–$350K
$10K$100K$1M$10M

Logarithmic scale. A dot marks the median; the band spans the 25th–75th percentiles. These are entire rounds, not individual cheques.

04 / WHAT HAPPENS NEXT

One investment. Two different paths.

A subsequent round and repeat backing
answer different fundraising questions.

19
companies with 24 months
of observable history

Raised another equity round

Any investor · within 24 months
10.5%
2 of 19 companies

Backed again by this investor

A subset of the companies above
0%
0 of 19 companies
i

Includes first investments on or before 22 May 2024. 4 newer companies and 0 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.

See the stage-by-stage denominators +
First stageEligible companiesNext round ≤24 moSame investor again ≤24 mo
Angel192 / 190 / 19
Seed00 / 00 / 0
05 / INVESTMENT RHYTHM

New names. Returning relationships.

Separate first investments from later
rounds in companies already backed.

New companiesRepeat rounds

*2026 is partial, through 22 May. Bar height counts first investments + repeat rounds; earlier years are complete calendar periods in this dataset.

06 / THE CO-INVESTOR MAP

Who else belongs on your research list?

Frequent shared rounds suggest a place
to investigate sector and stage alignment.

01
ANGEL

Lori Greiner ↗

4 shared rounds · 4 companies

Latest shared round Feb 2024
02
ANGEL

Mark Cuban ↗

3 shared rounds · 3 companies

Latest shared round May 2023
03
ANGEL

Daymond John

2 shared rounds · 2 companies

Latest shared round Feb 2024
05
ANGEL

Bethenny Frankel

1 shared rounds · 1 companies

Latest shared round Jan 2017
06
ANGEL

Rashaun L Williams

1 shared rounds · 1 companies

Latest shared round Aug 2025

Shared rounds establish recorded co-investment. They do not establish a personal connection, introduction route, or current willingness to invest.

07 / THE EVIDENCE

Explore the portfolio.

First investment comes first.
Amounts refer to that entry round.

23 dated companies
Complete dated portfolio, ordered by first investment, newest first.
CompanyFirst backedEntry stageTotal entry roundSame investor again?
Chalkless ↗Wilmington
Aug 2025Angel$400KNo later round recorded
VSEAT ↗Marina Del Rey
Aug 2025Angel$200KNo later round recorded
Nameberry ↗Montclair
Feb 2025Seed$350KNo later round recorded
Jan 2025Angel$500KNo later round recorded
Chefee ↗Beverly Hills
Mar 2024Angel$500KNo later round recorded
PSYONIC ↗Champaign
Feb 2024Angel$1.0MNo later round recorded
Jan 2024Angel$150KNo later round recorded
Tollwood ↗Harrogate
Jan 2024Angel$75KNo later round recorded
Jan 2024Angel$150KNo later round recorded
Dec 2023Angel$200KNo later round recorded
EyeWris ↗Santa Barbara
May 2023Angel$125KNo later round recorded
Apr 2023Angel$400KNo later round recorded
Cabinet ↗Washington, Dc
Jan 2023Angel$500KNo later round recorded
Jan 2018Angel$80KNo later round recorded
Jan 2017Angel$150KNo later round recorded
Oct 2016AngelUndisclosedNo later round recorded
Mar 2016Angel$100KNo later round recorded
Feb 2016Angel$80KNo later round recorded
Jan 2016Angel$50KNo later round recorded
Plated ↗New York City
May 2014Angel$500KNo later round recorded
GrooveBook ↗Lexington Hills
Jan 2014Angel$150KNo later round recorded
VerbalizeIt ↗New York City
Jun 2013Angel$250KNo later round recorded
Talbott Teas
Apr 2012Angel$250KNo later round recorded
0 more companies have undated investments

Kept in the 23-company portfolio; excluded from entry-timing calculations.

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