Brett Calhoun

Feb 3, 2026

3 min read time

When to Raise VC

Brett Calhoun

Feb 3, 2026

3 min read time

When to Raise VC

Brett Calhoun

Feb 3, 2026

3 min read time

When to Raise VC

Brett Calhoun

Feb 3, 2026

3 min read time

When to Raise VC

There is a quiet assumption baked into startup culture: if you are not building a VC-backed unicorn, you are falling short.

Venture capital is not a badge of honor. It is a financing model. When those ideas get tangled, decisions start to optimize for pitch decks instead of customers.

Most VC companies fail. A handful of wins must carry an entire portfolio. That constraint shapes everything downstream.

Many companies were never suited for venture outcomes. Some markets simply do not support hypergrowth. Forcing a venture-shaped story onto a business that wants to be smaller is how you destroy something that was already working.

The key difference rarely discussed is return expectations. Angel investors can be happy with a 5–10x outcome. That is life-changing money for a founder and a strong return for someone writing smaller checks. Venture funds cannot operate that way. We need 50x outcomes to make the model work. That requirement alone rules out entire categories of otherwise excellent businesses.

A small or focused market can absolutely support a great company. It can generate profit, exits, and real wealth. What it often cannot support is a venture fund’s return profile. 

Don’t get these two things confused. It will lead you to waste years of hopping between accelerators, reworking decks, and finding “creative” ways to stretch market size instead of serving your customers.

I am not anti-ambition. I am anti-mismatch. Many people overestimate how necessary or attractive the venture path really is because venture outcomes are the most visible. 

Venture capital works when there is a genuine opportunity to unlock a massive market and when capital meaningfully changes the outcome. Angels and bootstrapping work when a business can compound steadily and produce real cash or a reasonable exit without pretending to be something it is not.

The real question is not whether a company could be massive. It is whether the financing path matches the market opportunity it serves or can unlock.

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Build with us in any climate.

Start your building journey with a team that appreciates the struggle

Build with us in any climate.

Start your building journey with a team that appreciates the struggle