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Dan Holowack on the TechTO stage

Dan Holowack

Co-founder & CEO, CrowdRiff

Travel marketing technologyTorontoOn TechTO stages since 2017

Dan Holowack is the co-founder and CEO of CrowdRiff, the Toronto company whose visual content platform is used by 900+ travel destinations. A Waterloo engineering grad who started out at Research In Motion, he bootstrapped CrowdRiff to $1M ARR before raising a seed round in 2016 and an $11.6M Series A in 2018.

On the TechTO stage ×3

First seen on the TechTO stage in 2017. Every talk is searchable — ask the archive about Dan

In their words

Just tell a great story. So I ended up changing my positioning — the first slide of my seed deck ended up becoming 'searching for photos sucks.' It was a big decision to say I'm gonna put the word 'sucks' on the first page of a slide deck that's going to be seen by all of these highly educated, powerful people. But it got the message across.

TechTO Founder Journey, Mar 2023 · watch at 13:26

Abby and I, looking back, felt like the core things that started was: hire people that don't have an ego, and hire people that are kind. Bringing people together that don't have much ego and are really kind gets you a really long way.

TechTO Founder Journey, Mar 2023 · watch at 28:58

When we initially flew over to Europe and we were doing conferences and meetings, the question was: who else in Europe do you work with? We were like, oh, we work with hundreds of customers in North America — all these great names did not matter. In this kind of space it's really finding those early innovators.

TechTO, May 2017 · watch at 10:41

people make the decisions to go traveling and it's really precious it's gonna cost money maybe it's your only two weeks of vacation you have every year and what doesn't work anymore is that like one perfect beach photo or that fully staged photo shoot that somebody did three years ago with a bunch of actors.

TechTO, Mar 2023 · watch at 01:39

founders are also trained to tell these really catchy stories about how boom we were successful look at that like and it's perpetuated by the media but it was like three years of learning everything the hard way making no money and iterating piece by piece from the product to the market back to the product back to the market.

TechTO, Mar 2023 · watch at 05:06

we bootstrapped to our first million in ARR that was like our first 12 to 1

TechTO, Mar 2023 · watch at 11:51
A few quotes can’t cover everything Dan said on the TechTO stage. 1,600+ talks are searchable.Ask about Dan

More from TechTO ×3

Around the web ×4

Quick answers

What is Dan Holowack known for?

Co-founding CrowdRiff in Toronto and running it as CEO. Its visual content platform is used by 900+ travel destinations to source and publish user-generated photos and creator video.

What did Dan Holowack do before CrowdRiff?

He came up through engineering at the University of Waterloo and got his start at Research In Motion, where he worked on the people and operations team building internal tools. He then spent a couple of years in the social media data and analytics space before landing on CrowdRiff's market.

How did Dan Holowack raise CrowdRiff's seed round?

He bootstrapped to $1M ARR with 12-15 people first, then spent nine months raising. He dropped the cookie-cutter deck and rebuilt the pitch around one line — 'searching for photos sucks.' The $1M target was doubled to $2M on investor interest, as he told the TechTO stage in March 2023.

How many times has Dan Holowack spoken at TechTO?

Twice — a 2017 talk on the tourism marketing tech stack, and a March 2023 Founder Journey episode on building CrowdRiff.

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Maintained by TechTO · facts sourced and dated · last reviewed Aug 28, 2026