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Shayn Diamond on the TechTO stage

Shayn Diamond

Partner, Whitecap Venture Partners

Venture capitalTorontoOn TechTO stages since 2020

Shayn Diamond has been a partner at Whitecap Venture Partners since 2015, writing seed and Series A cheques into Canadian B2B software and medtech from Toronto after a corporate law career at Wildeboer Dellelce. He invests early and slowly: he tracked Silofit for roughly six months before signing, watching personal trainers move their whole businesses onto the platform.

On the TechTO stage ×1

First seen on the TechTO stage in 2020. Every talk is searchable — ask the archive about Shayn

In their words

He proposed this concept that you could marry a physical real estate footprint with an economic incentive to every party involved, so that they each came out on the winning side.

TechTO Founders & Funding, Apr 2020 · watch at 9:07

We're leveraging B-class office buildings, five hundred to a thousand square feet, limited windows, where it's not really palatable for a five to ten person office — but it's a perfect location for a small gym, so landlords are more than happy to give it up.

TechTO Founders & Funding, Apr 2020 · watch at 9:34

The service providers started booking more and more hours per week and migrating their entire businesses over to Silofit, and at that point that flywheel started to kick in.

TechTO Founders & Funding, Apr 2020 · watch at 14:04
A few quotes can’t cover everything Shayn said on the TechTO stage. 1,600+ talks are searchable.Ask about Shayn

More from TechTO ×1

Around the web ×1

Quick answers

Who is Shayn Diamond?

A partner at Whitecap Venture Partners in Toronto, where he has invested since 2015. He came to venture from corporate law at Wildeboer Dellelce and holds a JD and MBA from Queen's University. Whitecap backs seed and Series A B2B software and medtech companies across Canada.

What does he look for before investing?

Evidence that the economics work for everyone in the chain, then proof of repeat usage. On the TechTO stage in April 2020 he described spending about six months with Silofit before investing, and said the moment that decided it was watching individual trainers go from one booked hour a week to ten or fifteen.

What did Whitecap invest in at Silofit?

Whitecap took part in Silofit's roughly $1-million seed round alongside New York sports and entertainment fund Courtside Ventures, as Diamond described on the TechTO stage on 2020-04-09. He noted Whitecap is primarily a fund with a small allocation reserved for seed deals.

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Maintained by TechTO · facts sourced and dated · last reviewed Aug 12, 2026