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August 28, 2025 27 mins

Season 2 kicks off live from the ASAE Annual Meeting & Exposition in Los Angeles! Guest hosts Ben Muscolino, Gretchen Steenstra, and Jake Toohey of The Association Podcast sit down with Bobbie Racette, founder and president of Virtual Gurus. Bobbie shares her inspiring journey as an Indigenous queer woman in tech, from launching Virtual Gurus in 2016 to scaling it into a thriving, values-driven company. She opens up about overcoming challenges, securing funding, leading through COVID-19, and the critical role of company culture. The conversation explores how Virtual Gurus is integrating AI responsibly, Bobbie’s vision for global expansion, and audience questions on building inclusive workplaces and communities.

This episode is sponsored by Destination Canada and Visit Denver.

Associations NOW Presents is produced by Association Briefings.

 

Transcript

Ben Muscolino: [00:00:00] Hello everyone and welcome to the Associations NOW Presents podcast live from the show floor here at ASAE 25. I am Ben Muscolino with Brezio, AMS Geek, and Data Sangria. I'm here with my co-hosts of The Association Podcast. Jake and Gretchen. We are so excited to be bringing our format and our passion for the industry over the Associations NOW Presents podcast.

We have an incredible guest today and I'm gonna kick it over to one of my co-hosts and we're gonna get that going. So glad you're here with us today. 

Gretchen Steenstra: So I am Gretchen Steenstra, the permanent/temporary guest co-host. I think I came for five episodes and I don't know how many, maybe 50 now. My day job, I work at DelCor, a technology consulting company, and one of my passion projects is I'm a founder of AWTC, which supports women in tech and part of tech council and [00:01:00] all the association families.

So I'm really happy to be here and nice to meet you today. 

Jake Toohey: Hey, I'm Jake Toohet. I am the director of the association practice at Adage Technologies. We're a digital strategy, web development and design firm, and, work with all associations. And we are thrilled to have Bobby Racette, Virtual Guru's, former CEO, now president, founder.

So thrilled to have you. Can you start by just talking a little bit about what you do and your background and just kick it off from there. 

Bobbie Racette: Yeah. Hi. Thanks everyone. This is amazing. So founder and CEO of Virtual Gurus. So I started Virtual Gurus in 2016 because nobody would give me a job. I was looking for work for, I don't know, close to a year, and nobody would give me a job at all.

So I actually started it just to create a job for myself. And at the time, I had no idea I was gonna scale into this big thing. It was gonna go where it went. I had no idea that it was gonna be AI eventually, and that there'd be thousands of people working in the [00:02:00] platform. But here I am and happy to be here.

Ben Muscolino: Hey, Bobbie. We're storytellers in the association space. Your story is so incredible. We wanna talk with you about several things today, but to get things kicked off, talk to us about what you've been up to this morning and the session that you led. How was that for you? 

Bobbie Racette: I've been traveling a lot talking about my story.

I actually just flew in from Japan and I was speaking out at the World Expo, which has been amazing. Such an amazing experience. Just to be saying that I'm speaking and I'm out at the expo. I was there on a trades mission and just really telling the story, but this morning it was really just about telling my journey and about culture and my journey of being an indigenous queer woman in technology and how hard it's been to get to where I am today, and meant to raising millions and millions of dollars to run the company and to build the AI.

Now we're scaling globally, and I was actually in Japan meeting with senior leaders like the CEO of Mitsubishi to try to get our AI out [00:03:00] there a little bit more. So it's been a pretty crazy ride these last few weeks. 

Ben Muscolino: Bobbie we have so many things that we wanna learn about you, but I'm very interested in what was the turning point where you realized that you wanted to start virtual gurus?

What was that catalyst? Because you kind of talked a little bit about the need to want to create work for yourself. Was that really the catalyst moment? Talk to us about that. 

Bobbie Racette: Yeah. I was working in oil and gas in Calgary, Alberta, Canada, where a lot of people are working oil and gas. But layoffs came like when the gas prices dropped, and I think 37,000 people were laid off within one day, and I was one of those people.

But when everybody went

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