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The Founders Corner®

The Investors Who Actually Write Cheques In 2026

Inside the layer of capital that does not call itself venture

Chris Tottman's avatar
Chris Tottman
Feb 23, 2026
∙ Paid

Most founders still run a fundraising process built for institutional venture.
Introductions. Deck. Partner meeting. Internal discussion. Silence.

It feels like bad timing.
It is usually structural misalignment.

A large share of real pre seed capital in 2026 sits outside traditional venture funds with family offices, operators, angels, and small thematic vehicles. These groups do not behave like VCs. Their incentives are different, their decision processes are lighter, and their definition of risk is shaped by wealth preservation rather than portfolio optics.

To make this shift usable rather than theoretical, I built the Family Office Fit Engine.

It helps you identify which family offices actually match your stage, sector, geography, and raise size.

Below is the walkthrough.


I. Step 1 Your Stage

Idea → Prototype → Early revenue → Scaling

Family offices differ widely in stage appetite.
Some love true zero to one opportunities because they care more about themes than traction.
Others want early commercial signals, especially if the wealth behind the office comes from an operating business where execution matters more than storytelling.

This step removes the offices that would never invest in your maturity, even if everything else fits.
It reduces drift before it starts.


II. Step 2 Your Sector

AI, SaaS, consumer, fintech, climate, healthcare, crypto, or generalist.

Family offices do not think in rigid categories. They think in themes that matter to their family history or worldview.

A family office built on manufacturing wealth may care deeply about robotics.
A family office built on healthcare may prioritise longevity.
A family office built on real estate may look for tech that improves asset yield.

This section maps your sector to the themes they actually deploy against.
It replaces broad investor targeting with thematic alignment, which is where private wealth converts fastest.


III. Step 3 Your Raise Size

Fifty thousand to five million.

Family offices do not operate with the minimum cheque logic that VCs do.
They can write smaller cheques if conviction is forming, or larger cheques if the principal sees strategic relevance or personal interest.

Still, every office has a realistic band that sits within its comfort zone.

This step filters out conversations that would have died quietly because your raise size never matched how they typically deploy.
It helps you avoid the slow no.


IV. Step 4 Geography

Primary location and target markets.

Family offices are relationship driven. They care about access.
It is easier for them to invest where they understand the regulatory environment, have local advisors, or already have portfolio exposure.

Geography also influences trust.
A family office in London will often feel more comfortable backing a founder who has customers or early traction in Europe rather than in distant markets they do not know.

This step increases match accuracy by combining where you operate with where they have historically shown conviction.


V. Your Matching Family Offices

Once you enter your inputs, the engine returns:

  • Strong Fit offices

  • Good Fit offices

  • Partial Fit offices that still merit exploration

Each profile shows:

  • Cheque range

  • Sectors of interest

  • Stage appetite

  • Geography alignment

  • A fit score based on weighted criteria

The logic is simple.
Instead of searching for family offices manually and guessing based on website language, you receive a curated set of targets where your profile makes intuitive and structural sense.
This is what turns an opportunistic raise into a deliberate raise.


VI. Outreach Templates Included

Inside the tool you receive templates designed specifically for private capital:

  • A first outreach message that respects time and context

  • A warm intro request formatted to be forwarded easily

  • A post meeting follow up written for principal level decision making

Family office communication is different from VC communication.
They want clarity, precision, and a sense that you understand the risk and responsibility of taking their capital.
These templates help you signal that without overplaying confidence or underplaying detail.


Fundraiser OS

Every week I release new tools for founders raising in 2026.

Term sheet walkthroughs.
Due diligence checklists.
Investor fit engines.

Tools that help you operate like a professional capital allocator, even if this is your first raise.

If you want the full database, the matching engine, and the complete workflows, everything sits below the paywall waiting for you.


The Family Office Fit Engine

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