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 into the city and was trying to find work. By the time I got there, all the jobs were either being taken up, but all of the people that were more qualified or maybe fit their culture more got the jobs over me. And so I was looking for work for so long and nobody would hire me at all.

I don't know what it was. I'd like to say maybe it's just 'cause of who I am, [00:04:00] but a queer woman in tech and nobody would hire me. So I actually created a job for myself. I was the virtual assistant. I wasn't actually planning to scale it, I was just doing it to create a job for myself and. I had 19 clients, so I started with $300 in my pocket and I bootstrapped it to 1.8 million in revenue.

And then I realized I needed to hire, and then I needed to raise money and there's a lot of work to do. And so I closed my first funding round in 2020. The light bulb went on, why don't I start this platform to create work for people like me? And then all of a sudden, the platform just went wild.

Ben Muscolino: So the serendipitous timing.

Where everyone that maybe got to the jobs before you did and then you raising money in 2020 and scaling when you did. What an incredible twist of timing for business being in 2020 when everything went virtual. Right?

Bobbie Racette: Everything went virtual, and then I closed three funding rounds during [00:05:00] COVID, which nobody was investing at the time because they were so scared to use their dry powder.

But I was like, let's go and, and it worked well. We scaled 300% year overgrowth through every year and through COVID through three years.

Gretchen Steenstra: So you were describing how difficult that was. Were there assumptions you made and had to adjust throughout these cycles? Like you said in the very beginning, you didn't know how to raise funds and people were turning you down.

But as you matured and evolved, what are the assumptions you're facing now that you assume when you're going out for funding or building your company, that you have to adjust and.

Bobbie Racette: Yeah, I guess the landscape has changed so much from COVID. Before COVID, it was scary. People weren't really interested in the freelancing platforms and it wasn't as well known.

And then COVID hit and then everybody went remote and everybody was laid off their jobs. So people started going to platforms like ours. All the administrative people were getting laid off and then they came to me and so I was picking them up and recycling them back out and cold calling [00:06:00] the companies that were laying people off during COVID.

And I'm basically saying. Your company still needs to open and function, so we got E four back office support. The thing for us was just assuming that we were gonna be bigger then, and we were just gonna scale and we leveraged COVID for that and I was quite surprised with where it went. During that time.

We built out a people over profit program. So all the startups that were struggling to pay the bills, we gave them free virtual assistants. Oh wow. Yeah, yeah. Right after I closed my first finding round. So I'm like, thanks, invest. Or by the way, I'm gonna give free service those away

Jake Toohey: There's one of the things that I took away from your session this morning was the culture thing.

Yeah. The kind of culture that you built at the organization. And I think, you know, one of the things that I, I remember is you saying that you used to hear the resumes hit the bottom of the trash can. You never wanted to make anybody else feel like that. Can you talk about that involving culture and what's driving that?

Bobbie Racette: Yeah. This was back when you used to go to the offices and hand in your resume 20 16, [00:07:00] 20 17. And like I said, nobody would hire me and I would literally go to leave the office and I could hear a piece of paper hitting the trash can and I knew that was my resume and it just made me so angry and sad. And essentially that's almost what powered my thesis on if we provide more work to marginalized communities, then.

We can't let people shine if we're gonna keep doing that. 'cause surely if I'm feeling that, then how many others were feeling it. But it did was inspire me and fuel me to keep going and to create this. I guess some will say I created it out of anger, but I really just created it out of spite. I thought “you all told me no so many times that I'm going to take my own control now.”

Gretchen Steenstra: Yeah. But I, I don't even know if it was spite you were just so passionate about. I found this, and a lot of the things you do, which I think is really interesting is you formed it into repeatable like almost products. So I'm looking at your culture cleanup toolkit. And so in addition to running a company, raising [00:08:00] money, growing the company, taking care of your employees, you also seem to have packaged some of these thesis statements and ideas into tools.

I've never seen that with a founder who's doing all of these things. And creating, you know, actual artifacts to help with people.

Bobbie Racette: It's all tell you much when you go to an office or a startup or tech company or a business, any business, and people talk that their culture is good. But then you go in, you're like, whoa, this thing's about to explode.

And so I, I see a lot of that and I'm a firm believer of if you're gonna talk the talk, then you gotta walk the walk and you gotta show it, right? So the culture toolkit was more on, based on. We had some toxicity go through our company. And during COVID, when toxicity comes into your company, it's like a snake that just doesn't stop and you have to do a lot of work to fix it to right side it.

And so I really built the toolkit based on how do I make sure that I'm creating an [00:09:00] open and honest, happy space for all of the employees? How am I making them safe? How am I allowing people to understand the culture and what is allowed and what's not allowed, and what kind of a culture that we wanna have in the office.

And so it really helped with that.

Gretchen Steenstra: What made you say, whoa, so a minute ago you just, you said you walk into an office and you feel this, like, what are a couple things that people don't notice that you noticed?

Bobbie Racette: Like male leaders, for example. And when you go into, also say it like, tech bros, let's be real. I love tech.

I'm in tech, but tech bros. Can be a little bit hard to handle. And if there's women working and those, they're mansplained in weight. I'm not saying it's everybody. 'cause believe me, I have a lot of tech friends that are males because I'm in the tech community and they all treat me like I'm their little sister.

They treat me really well, but you can see it and it can really shut down your business. I've seen it shut down some successful startups.

Gretchen Steenstra: We joke a lot at AWTC. We're advancing, empowering women, but men are welcome. You know, like it's not [00:10:00] excluding men, it's. Making sure that we're all being respectful of each other.

And Jake and Ben are two of the biggest champions we have at AWTC. And I think that's been interesting with us as people ask, can we join you? They're like, of course you can join us. Just don't be a jerk. You know? I mean, it's not hard, right? Yeah. So there's a lot of men in part of our organization that are great.

Bobbie Racette: Our new person taking over my role, I won't say too much just 'cause it's going out, but is male and I'm happy for it. We're a woman led indigenous business. 90% of my VPs are women. I have an all female board and I'm proud of it. I'm proud that we have a male taking over as my successor. Very good.

Ben Muscolino: Alright, so we're gonna keep going here, but we're gonna take a quick break and just hear from one of our sponsors. Quick note from Destination Canada. From the rugged Rocky Mountains to Sparkling Ocean Shores, Canada offers world-class venues and visionary leaders like Bobby Rossett. It gives you a sense of [00:11:00] belonging, the ability to unlock new ways of thinking, and a place where great business minds come to open their minds for business events that inspire, naturally build partnerships, drive transformation, and leave a meaningful legacy visit.

Business events canada.ca. So we had the pleasure of having Magic Johnson join us yesterday and he mentioned DEI being a thing, not being a thing, whatever's going to do with that. However you normalize that for, for yourself and, and any of the listeners businesses. But basically what he said is, let's just start being good again, right?

And however you label it or don't label it, let's get back to just doing right by each other. And I think that resonated with the room because. It's on a lot of people's minds and how that's gonna impact funding and culture and all these things. And it's a topic in our industry related to, you know, how are people financially gonna put things together, what's their reliance on, you know, what can I have associated with my business and can't [00:12:00] I, in order to get certain funding or when certain business?

And I think it gets best to the core of doing the right thing and working with the right people and building that culture. And so I guess what I'm trying to get at is talking about culture. Like where does all that resonate for you?

Bobbie Racette: Well, my mom always told me, treat people the way you wanna be treated, right?

Like it is common sense. And I think every company should have that. And I think big things can happen if you treat people the way you wanna be treated. Just 'cause I'm a CEO, it doesn't mean I treat the customer service rep in my company or the sales person any differently than the COO or the CTO, I treat them all the same.

Jake Toohey: Can you talk a little bit about adversity and the adversity you've faced? Talk about. How you got to the point of actually getting the funding that you needed to, to grow and scale?

Bobbie Racette: Yeah, so I bootstrapped virtual gurus to about 1.8 million in revenue, and it was then I realized that I probably needed to start raising money, but I had no idea what to do.

I was like, oh man, this is gonna be crazy. I literally [00:13:00] started the company with $300 in my pocket to go to having to raise out of valuation to raise millions. And so I set out to start pitching and I pitched all over North America. I went through 170 investors saying no, and I knew all it took was just that one.

Yes. But I was like, when am I gonna get the yes, yes. Yeah. The first yes, was the hundred and 71st pitch, and it was a cold email, reach out to an indigenous funding company, and five minutes later they called me and then they led that round. And then Telus Ventures led in second round and Telus Ventures coming on and they have MassMutual here in the US on my cap table now, and some pretty big names.

Now.

Jake Toohey: You talked also about giving people feedback. I mean, as you had to kind of evolve your pitch over 171 different pitches. But I really liked hearing about your methodology with making sure that you're getting people feedback, even if there's some rejected attached to it. Can you talk a little bit about that?

Bobbie Racette: Yeah. I like to tell people that it [00:14:00] was probably quite annoying to people, but when somebody says no to me, other than the initial kind of jab to the heart where you're hurt and you're like, what? You don't wanna invest in me? Like why? Once that goes away, it's the, okay, but tell me why. Okay. And here's the funny thing about investors is they all say the exact same thing when they're just saying no.

And it's an easy way out of you don't fall in line with our thesis, although I do, and the company did. 'cause I wouldn't be pitching if it didn't or you're not scalable, right? And so I started actually going back to them and saying, look, you can't say I'm not scalable and you can't say this. Tell me the real reason.

Tell me the real, and putting the ball back in their court, holding them accountable. It's the fact that. Maybe they just didn't have enough space in their hearts for me because of who I am, like a woman with tattoos and queer, it really scared a lot of people, especially in the VC world. And so I really had to learn what I needed to adjust.

What was it that really made me not get [00:15:00] those investments? And really at the end of the day, none of them had an actual reason. But I was able to tweak and build the company still while I was going through that.

Gretchen Steenstra: Yeah. And once you have a few, then you have some evidence

Bobbie Racette: that other people invested in.

You're right. And then once you get the one investor though your first round, then it's easy getting investment after, right? Yeah. 'cause then you're like,

Gretchen Steenstra: it's real. So when you were out, like you have just, so in your multifaceted CEO role is you are scaling financially, how are you balancing scaling your staff?

Back at the office who was doing the work that you were pitching? How? How did you do that?

Bobbie Racette: It is hard because you hire based on how much money you have. We're really lean team 'cause you gotta protect your burn and we're very lean. So at the time during COVID, I only had five employees. At the end of COVID I had 60, almost 60 employees, 59 employees, and then thousands are working in the platforms, but succeed in the actual office.

And then after COVID and the technology started going and working, we [00:16:00] did a series of layoffs, and that was probably the hardest thing for me was laying people off. But we're about 30 employees now.

Ben Muscolino: My reflection point is that, I guess instead of conforming, you really tried to force feedback out of them and keep your identity.

And I want to ask, how is your identity and owning your identity as indigenous LGBTQ plus leader informed the way you actually lead? And, and think,

Bobbie Racette: I was really scared to talk about this story of me, my indigeneity and my queerness especially. I was really scared about that. And I was also really afraid about my parents, like ruining my mom's story as an indigenous woman that her parents were residential school survivors, and it's a really touchy subject, so I was really afraid of living that and telling it.

But once I did, and once I talked about it more. Uh, virtual gurus scaled. I'm out here talking in Japan, talking in Singapore, all these places in Portugal, [00:17:00] everywhere, and virtual gurus is just scaling and a lot of that is 'cause of the brand, which is me being the brand of the company. So I think through all of it, I've learned that if you just tell your truth, the world will open up for you.

Yeah.

Gretchen Steenstra: And I know you, you have this announcement of changing from being the CEO and the founder. But this is common with a lot of leaders that they build a brand and then they wanna sustain it, so they hand it off to somebody. But you're the brand. What are some of the things you would advise people that you protect your brand, but you also let the next generation take the brand in a different direction?

You know what? Clearly you plan this because you wouldn't have done it, just, you know, spontaneously.

Bobbie Racette: Yeah, no, it's been in the plan, in the works. I think the number one thing is respecting and understanding that. It's your story when you're kicking it off. But for me it's really important to that all the other people in the platform, especially all the folks that are transitioning genders, the neurodiverse community in our platform [00:18:00] to the veterans, the single stay at home moms, the retired folks that working on our platform, it's now their story.

And I want their stories to be heard more than mine now. So it's changed, but the Bobby Rossett brand is ongoing. 'cause now I'm, I've actually started a coach cast similar to this. But it's called Take the Seat with Bobby because it's about taking the seats that we were never given as women entrepreneurs.

And so that starts right away actually.

Gretchen Steenstra: What are a few of those seats you're gonna start with? Like are there specific areas?

Bobbie Racette: Yeah, it's gonna be pretty predominantly well known woman in Canada to start with. 'cause I'm gonna do it in person like similar to this and then we're gonna travel and do it.

Ben Muscolino: We're gonna take a quick break and just hear from one of our sponsors very quickly. If you're talking about the top meeting destinations in the country, you have to include Denver with its incredible Rocky Mountain views and 300 days of sunshine. The brand new 16th Street includes dozens of restaurants, patios, art installations, and free [00:19:00] shuttles, all within walking distance of 52 downtown hotels.

It's a lot of hotels. Very convenient. And there's the newly expanded Colorado Convention Center. The 80,000 square foot Bluebird Ballroom is a game changer along with a 20,000 square foot outdoor terrace. Come check out the mile high city where you'll meet uplifted.

Jake Toohey: I wanted to ask about how you evolved the company.

Uh, can you talk about how the company changed one, the availability of artificial intelligence and it just becoming so wide scale?

Bobbie Racette: AI is everywhere, right? AI is not going anywhere. And about eight months ago, we were like, you know what? It's not gonna be long before AI agents, like virtual assistants are gonna overtake actual human agents.

And so the best way to deal with that was to jump 10 steps ahead and start building our own agent. So we built an ethical 24/7 AI virtual receptionist that's actually now being built into a full AI agent. So it can do [00:20:00] demos for startups, it can do outbound SDR sales, it can do calendar booking. And so what we're gonna do is use that AI to create more work for the actual human side.

So we're combining AI and human experience together. So we launched it in January and it's flying hard, like it's probably a stickier product than our human side. But it's a cross sell opportunity. So some of our biggest clients are MasterCard, alis, and it's a huge cross sell opportunity. Get them signed up to the AI agent and then provide them a human

Gretchen Steenstra: right.

But you said ethical. So how are you training your agent to be ethical? Because that's one of the things we've heard for underrepresented people is AI can actually hurt them because the large language models are. Flawed. And so you're just doubling down on bad data, which is why I have a love-hate relationship with ai.

So I just circled ethical.

Bobbie Racette: Ethical AI to me is obviously is that, but one of the main things for me is how are you creating more employment versus taking away employment? And I think every single [00:21:00] company is gonna have to have AI eventually. It's just the way it's going, sadly. And so it's really on how are you building and training your ai and what is your AI able to do?

For us, we focus on making sure we're training our employees to use AI the best way that they can so that they're not going offline. You know what? Use it for content. Use it for this if you want, but don't use it for things that are not in your ability. Don't use it for that learn Still, it's ethical AI for us, but our AI is, it speaks 44 different languages and we've gotta fine tuned right now.

But we're creating employment with it.

Gretchen Steenstra: Right? But I love that you're cross-selling, like I think that's the way they use it, the right way is you're educating people. This is where the AI is an effective tool and this is where the other staff is a good tool, right? So I think that's very important nuance that you're focusing on

Bobbie Racette: the it can imagine if you are going into a store or a salon and you're called and it's a twenty four seven AI receptionist answers your phone.

And you [00:22:00] really need to talk to a human, press one to talk to human, then it will go to our humans, right? So there's still the work creation side of it, but the difference is we want all the businesses to put this AI on their sites and let the AI learn and go from there.

Gretchen Steenstra: And I think people are okay with that.

You know, like we're all kind of trained to go through a couple prompts for efficiency, so I think that's fine.

Ben Muscolino: Well, and sometimes depending on the person's style and how they want to be supported. Or maybe the situation they're in, like, I'm distracted with something else. I need to talk to a person.

Right? Versus I have my speakerphone, I'm multitasking. Let me go through the prompts. I can, you know, multitask and do that. So you're catering to situationally where they are in their journey of their day or their business, or their need or their urgency.

Gretchen Steenstra: And I think another really important thing that you underscore is neurodiverse.

And so I think that just having all these different facets. Like you were saying, Ben, people communicate very different ways and so some types of people prefer to have a just much [00:23:00] more streamlined in ai does that. You ask it a question that answers you, they don't really need the interaction, the conversation.

They just need to get what they want. Yeah. And others need a different interaction.

Bobbie Racette: One of the other things that human virtual assistant platforms in North America are not doing is teaching their virtual assistants to be strategic by using the ai. And that's what we're doing. So therefore we're creating more productivity.

So some would argue then you're taking away more billing time for you and it's, yeah, but our number one goal isn't the billing time. Our number one is how do we save clients time and money? So our VAs are billing, let's say 30 hours a month. I'd say, let's say they're working on one client for 30 hours.

Do you know those hours were full productivity hours based on how much work they were able to do?

Jake Toohey: So I think we’ll take questions from the audience, if there's any, but, I did want to kind of end this. Section of the discussion with what's next for virtual gurus.

Bobbie Racette: I think we just closed a fun round a couple days ago, so I was working on that.

It's much easier this time around. [00:24:00] I think the next thing is Virtual Gurus wants to go global, so I was just in Japan pitching Virtual Gurus on the global stage out at Expo and meeting larger partnerships.

Ben Muscolino: I think we've got some questions coming in from the live audience here at A SAE annual in la.

Let's check 'em out.

Colleen Gallagher: Hey, I'm Colleen Gallagher with OnWrd & UpWrd. I, I'm sorry I'm losing my voice, but I love your story and it's really incredible, like this growth and, and how far you've come. And I know you said this is your first time here at a SAE. What do you think the association community could learn from this kind of growth and like, what could they take in, in terms of the community building?

And so many associations I talk with right now are really struggling with engaging the next generation and growing and instead of losing members, so what, what would your advice be to them?

Bobbie Racette: That's a great question. I don't know. There's so much to it that I could answer. I think it would be is don't be afraid to learn.

Right? Learning from anybody that is in your community or the communities you're building or the people, it's [00:25:00] all about being able to learn what their needs are and then being okay with being uncomfortable with it. Like we have a massive community and every day I'm learning from them. I'm, I get on the lines and learn how they're billing by the minute and how uncomfortable that is.

Yeah, I think it's just don't be afraid to learn and take all that knowledge and soak it in and be a knowledge keeper because that's what they need.

Ben Muscolino: So I have a final question, selfishly, right, and hopefully everyone can get something out of this, but I wanna ask this because I run multiple tech companies, I guess I one of those tech bros with the ambiguity around formality.

Uh, around DEI and I think everyone in this community believes in just being great to each other. Going beyond DEI statements to create workplaces where people can truly feel like they belong. What advice would you leave people with? And let's talk a little bit about that.

Bobbie Racette: I think, I know like the US is going through a lot of the DEI stuff right now, and I think you should just let that make you.

Shine even more. I think you could [00:26:00] still talk DEI with talk talking DEI, right? Like it is more about showing it instead of just talking about it. So we can all still say, I choose how to have my business show up every day. I choose how to have my employees show up every day. But you could still do it underhandedly without actually saying, we're JEDI, DEI, right?

So you just gotta lead by example. If you are doing it, then everybody else is gonna follow.

Ben Muscolino: Well, it's been a real treat to sit down with you and steal a little bit of time out of what is a very busy day already for you and a very busy time for you in business. And congrats again on your round. What round was that?

Bobbie Racette: We're gonna call it a Series A today because we're gonna work on our series B, which is about 40 million. Okay.

Ben Muscolino: Well, I want to thank everyone again for listening to this episode of Associations NOW Presents. Join us each month as we explore key topics relevant to association professionals, discuss the challenges and opportunities in the field today, and highlight the significant impact [00:27:00] associations have on the economy, the US and the world around us.

I'm Ben Muscolino from The Association Podcast. Joined by Jake Tooey, Gretchen Steenstra, and a huge thanks again to Bobby Racette. Again, before we leave you, we want to thank our episode sponsor Destination Canada, and Visit Denver. For more information about our sponsors, check out the links in our show notes. Be sure to subscribe to our podcast on Apple, Spotify, wherever you listen to your favorite podcasts.

For more information on this topic, visit Associations NOW online at associationsnow.com.