035: Pirouetting Her Way to Tech Founder with Mentorly’s Ashley Werhun

C: Podcast

Ashley Werhun is the co-founder of Mentorly. Her first career was as a professional dancer. Today, we discuss how she learned how important mentorship was through her performing career and how she used those lessons to build Mentorly. We also discuss some of the most important traits a mentor should have and more! 

Key Points + Topics

  • [2:21] Ashley Werhun grew up in Edmonton, Alberta. She spent the last couple of years of high school in a professional ballet school and graduated around age 16. That career starts at a very young age. Right after graduating, she moved to San Francisco and started working for a large touring dance company. While working, she had access to a free undergrad online program. She virtually attended Boise State and majored in psychology, making time on long flights and travel days to study and take her courses. Before graduating high school, she spent a couple of summers living by herself in New York City, attending Julliard’s summer dance programs. 
  • Her performing career exposed her to so many different countries, people, cultures, and markets, and that helped bring out the entrepreneurial spirit in her. Even when she was working on a touring show, they would always go beyond the traditional touring company activities. They went to cultural training before attending new places. In each city they performed, they would also do a cultural exchange with local groups and organizations. 
  • [7:52] According to Ashley, a mentor is someone who is guiding someone on a peer-to-peer basis that’s a bit beyond them in experience and using their lived experience to guide them. It goes beyond traditional “lessons” and passes down what they’ve learned to help the mentee avoid mistakes and also let the mentee know they’re seen in their experiences. Just because someone is an expert, they’re not necessarily a good mentor. They must first and foremost be committed to mentoring and willing to set aside time for this relationship. Good mentors tend to have high levels of empathy and understanding without passing judgment. When you’re mentoring, you must be fundamentally optimistic. This optimism in mentors can help people over the mastery “peak” when they’re just beginning to be bored with their job and often looking for new opportunities. 
  • [14:45] Ashley had a good career as an artist. She worked very hard for her success but knew there were other people objectively more talented than her who were less successful. She was very determined, though, and would often take people whom she looked up to out for coffee to learn from them. Other 17-year-olds were simply not doing it. One of her most influential mentors was and continues to be, Alonzo King, a dance instructor in San Francisco. He helped her see the focus of her dance career should be on the process, not the end goal. He had big ideas about the world in general and would weave them into his dance lessons. He would ask, “What work do you have to do before you get into the studio to be confident enough to show up to work untethered?” He’s also questioned if you’re not able to be authentically yourself, what sort of ripple effect might that have? These are lessons she’s brought throughout her career. Mentorly has about 11 angel investors; they’re all at the top of their career fields. Some help discover what’s the top focus for business. Some will walk you through a deal for two weeks. Some are there for those “emergency” calls at 11 o’clock at night. All while they’re running their own businesses with no time to spare. 
  • [26:55] Ashley knows she was lucky to have the mentors she’s had who have listened to her and answered her questions. As she was finishing her dance career, she began pondering what her next chapter would look like and if it might be something that wouldn’t require her literal blood and sweat. She wondered what the world might look like if everyone had mentors like her. 
  • [30:32] Startups shouldn’t exist; they’re impossible. They start with nothing and turn it into a business that serves people. Early funding was very difficult for Ashley and Mentorly. There is certainly a learning curve to finding what matters and where you should spend your money. Now, they’re much more careful about spending. 
  • [39:52] Mentorly is woman-owned and founded. Their mentor team has a variety of races, genders, and backgrounds. They generally have a very diverse team because they’re Canadian. They focus on different groups and customers. They work with the Black Business and Professionals Association (BBPA), which focuses on mentorship opportunities for black business owners. It’s important to know if a similar race and demographic is important to you as a mentee when looking for a mentor. A similar experience can be helpful, but mixing it up also works really well sometimes.

Guest + Episode Links

Full Episode Transcript


Hello everyone, I’m Danny Gavin, founder of Optidge, marketing Professor and the host of the Digital Marketing Mentor. I’m really excited for our guest today Ashley Weron, ceo and co-founder of Mentorly. Ashley was a professional dancer for over 10 years and she saw the need for formal mentoring solutions in the arts industry and beyond, and she launched Mentorly in 2017. Mentorly is a cloud-based mentorship solution for businesses and organizations looking to invest in their people and help them soar. Today, we’re going to talk about mentoring within a structured environment and with a strategy. Ashley, how are you?



Doing really well. How are you?



Great, I’m so glad that you’re here. I know that you’re calling in from Montreal, a place which is close to my heart, having a lot of family there. I was there a couple of weeks ago. I’m super excited to be talking to you today.



Me too. I saw the title of the pod, I was like this seems like a fit for what we do.


Danny Host 01:55

Just a little bit right. Yeah, I think the way I stumbled upon you, I think it was just on Twitter, I don’t know how you popped up, but you did and it was meant to be.


Ashley 02:02

Perfect Twitter or X keeps making it happen somewhere or the other.


Danny Host 02:07

I saw a good tweet that we as the community just need to keep saying tweet and Twitter and hopefully, if we just stick with that, it will maybe come back. We’ll have to see.


Ashley  02:17

Yeah, it’s a platform of the people, for sure.


Danny Host 02:20

Let’s dive right in and we’ll talk about your educational and work background. Obviously, where did you go to school and what did you study? I’m sure we’ll touch upon the life of a ballerina.


Ashley 02:30

I grew up in Edmonton, alberta. I moved to San Francisco right after high school. I spent the last couple of years of my high school life in private ballet school, so moved out of the house really young, was in an apartment, going to private ballet school, which is pretty common for that track. I actually didn’t go to university. I went straight into a ballet career, which is also quite common.



I remember being asked at an international ballet competition in London I was 16, finishing up high school, and people said do you have a job yet? My mom looked at me like no, no, she’s finishing high school and they kind of look like why you should just start working and do homeschooling. That career starts really young. I started my first job at 18 after living in San Francisco at a company called Ballet British Columbia. Then, luckily, while I was working we developed relationships with one of the universities that we are around. I got kind of a free undergrad. I would take university classes on the road and after workdays. It was a pretty special program that they had for some of the artists I was able to study that way. That was at Boise State University. I majored in psychology.


Danny Host 03:38

Amazing. It’s cool that you had that push to do the degree while you were busy. I know a lot of people you’re so busy it’s difficult to do that additional studying.


Ashley 03:47

Yeah, most of the long days you’re also expected to go to acupuncture and chiropractor. That is your job is to keep really healthy, to be kind of world-class. I’d always liked doing something on the side. I needed a distraction. Then you’re on tour about seven months of the year. You have these long plain rides and when you get somewhere you have a mandatory day off to adjust. It felt like a good thing to focus on. When I was growing up my mom always said when I said should I go to university or start a career, she said I really remember her saying universities don’t close, do the thing first. That maybe relies on kind of age brackets or opportunity brackets and then the other stuff can be layered on. I was really happy to do that. It gave me a lot of grounding while I was on tour and off in the summer.


Danny Host 04:37

I know you also spent some time at Juilliard.


Ashley 04:39

I went there in the summers when I was younger. Juilliard’s generally post-secondary, so you go from 18 to 21,. But I got a job right out of school so I actually didn’t go to the university program. They have kind of early acceptance for dancers and musicians in the summertime when you’re really young and kind of at that you’re edging on that world-class experience. To go for the summer. I remember going when I was 15 or 16 to live in New York for the summer by myself. It was an awakening but it felt like, okay, this is a path I really want to pursue professionally.


Danny Host 05:13

Obviously, you had a lot of experiences inside and outside the classroom, whatever that proverbial classroom was Sure. What experience do you think were most impactful in directing your path?


Ashley 05:23

I would say pushing me towards entrepreneurship. I think the experience of being in multiple markets now I know they’re multiple markets and I was 21 years old I just thought I was in Vietnam on tour and seeing how people lived and why they lived, I think was really impactful. Being in China for months on end on tour. You meet Dancers that are have very similar lives to you professionally, but outside of that, everything is different from hey, you’re texting me on we chat. What is we chat? It’s a global app, and then you dive into those ways of living, and so being able to tour and and and be in most countries by the time you’re like twenty five years old was a really Big awakening to me of what matters to people in different settings. And then why was I kind of like when the lottery, being born in canada and being able to work in the us there’s very little limitation I think that was a really big one. Even when we were touring, though, we went sort of beyond the traditional touring sense, like with one of my companies, train McIntyre project.



Southeast Asia is part of this initiative called soft power that Hillary Clinton introduced, and she was trying to introduce countries to each other, but on the basis of not war and wishes good.



And so before yeah, before we went to Vietnam and Philippines and korean china, we would do training in dc and get cultural training and different things to expect, to know what to expect right, because in different areas of china, you probably know, there’s a whole city just dedicated to media and all universities, all high schools lead into that media track.



So when you’re going to that city you know that when you get off a bus it will be a red carpet and you expect to have a gift in hand and all of these little things we get trained on and In your young twenties I think that’s a big kind of eye opening experience. And then in every city we would not only do a show but we do a cultural exchange With a group that they’re either a group of at risk kids or, like a tribe in in Vietnam, came down from the rural areas to teach us like their dance that’s so historical to them as a culture. Or you know a professional ballet school in China where I was teaching the twelve year olds and they were way better than me. So I think layering on those cultural experiences as I was dancing was it was a large part of education.


Danny Host 07:32

I mean, yeah, sounds like the experience is that you had. Your average teenager or young adult does not have, and it really doesn’t surprise me that you’re a founder of this amazing company organization having such a diverse background and Sort of foundation to build your life on just so cool yeah, I feel very lucky let’s jump into mentorship. As someone who runs a company driven to help facilitate and improve mentoring, how would you define a mentor?


Ashley 07:57

A mentor is really someone that is guiding someone, either in a peer basis or that is a little bit before them, and using their lived experience to do so. So it really goes beyond sort of an education model where you’re trying to teach someone skills or Verbiage or lessons that you know or textbook knows. You’re trying to take all of your experience, that you’ve lived in real life in the context of that industry, in the context of your own experience, and pass that down and it’s really to help the mentee To effectively not make the same mistakes you’ve made and also to be seen when a mentee is going through someone and a mentor can simply say I see that I’ve experienced that too, and maybe it was much, much worse, so don’t worry as much. It’s a very powerful relationship, but that relationship to find and to maintain is actually quite abstract for people, and so we really wanted to dig into that topic in Mentorly.


Danny Host 08:53

So what would you say are the most important traits in a mentor? So, besides the fact of like having a lot of experience in that area, but what would you say makes a good mentor?


Ashley 09:01

Just because someone is excellent in what they do, it doesn’t make them a mentor. That’s one thing. When we work with companies, they ask us for a lot of guidance around. That topic is even if we’re Asking executives to mentor, are they ready? Are they the right people? So I think a mentor needs to, first and foremost it’s very tactical, but be committed to set aside time in their life to do that. They need to know that they want to dedicate, let’s say, an hour a month or a half an hour a month or at will, whenever they need. I’m going to answer a call to help in this relationship.



I wouldn’t label yourself a mentor if you’re not actively doing that and making this space for it, because it’s like any relationship, you need to invest time to, so someone that has some time capacity to give back.



Good mentors generally lean to have high levels of empathy and understanding or willingness to understand, and so they will listen and absorb information without passing judgment, because you can never be in.



That meant T shoes and they’ve gone through and describable things in their life depending on their background, and you have to know that their experience is worth listening to and absorbing before you give any feedback.



And the other part is, I think you know when you’re mentoring, you’re fundamentally optimistic, right, you see potential in people, you see that challenges can become overcome. You want to wait until the end to give feedback, and then you also know that it’s going to go through the filter, that it may be taken and it may not be, and and that’s OK, and you have to kind of let it go right. You’re not their boss, you’re not necessarily their manager, and we’ll get into why that maybe matters not to be directly mentored by your manager, but you’re there to support their journey, and so I think most mentors have kind of a quality of selflessness also in theirs that they just want to be helpful and and it’s really not about them in that moment- I love that point about like the optimistic perspective, because I’m like thinking on the, you know, on the opposites, and someone who kind of looks at the glass half empty.


Danny Host 10:53

I don’t think they’re going to be a good mentor.


Ashley 10:55

Sometimes it trains you to be right, like being a founder, I think you. It trains you to be optimistic because you’re looking for opportunity in the world. But I think sometimes we have an easier time giving other people advice and taking our own. So even if you’re sort of down in your own experience and nothing’s going well and the economy is crashing, but you meet with like a really hungry person that is new to the industry and they’re not as jaded and they don’t have as much information and so you have to be optimistic because their life also is just beginning in some respects. So I do see also levels of optimism increase as you mentor. There’s a study that we cite a lot around the science of giving back and the more you do the action actually, the happier you become. So it is also something that you can do to become more optimistic, which is good yeah.


Danny Host 11:42

And I think that’s such an important point about giving back and that actually makes you happier. Some people think, like, by giving my time, I’m actually taking away for myself, but I’m a big believer and I’m sure you have this study to prove it. But yeah, when you actually give, you actually gain a lot more. So that’s why, if you think about it, that relationship is really. It’s a two way street. Both people gain a lot.


Ashley 12:02

Yeah, a lot of the times I’ll walk away from conversations and I’m like, oh gosh, I’m so happy they took the time and I was like, oh wait, they just thanked me for taking the time.



But I learned a lot because I’m reminding myself of things that I really want to do, that maybe I’m not implementing right. There’s that aspect too when you’re teaching something, you better be following it yourself, and it’s really a really good reminder. And the other thing we find is it’s linked to purpose. So a lot of the times when you’re kind of reaching that level of mastery in your career, it can get kind of boring right Like on the traditional S-curve of learning. When you’re sliding in the middle it’s the most interesting to someone. And then when you reach that mastery peak, that’s often when you’ll see a change of industry or job, because people get itchy for change. So when someone is a master or reaching a mastery of their role or their skill set, giving back and teaching some of that can reinstate their purpose and remind them kind of how good they are at what they do.


Danny Host 12:57

So do you feel like companies should actually look at senior people in the organization and, by kind of putting them into mentorship positions, might actually keep them there longer?


Ashley 13:05

Yeah, retention is a big problem that companies come to us with right, because when you look at the stats, they’re pretty alarming. Like for the top tech companies right now Uber, I mean, facebook, snap and these are people that are throwing money and kind of workplace flexibility and all that kind of stuff. Their average 10 years, two years, and so imagine throwing a few hundred thousand dollars at someone, all of the training, all that kind of things, just to lose them. That cycle is pretty deafening when you’re investing, and so it’s really worth it to invest to retain someone.



But there are a lot of things that go into someone wanting to leave their role, but a big one is that they’re losing a sense of purpose, that they feel more purpose, maybe from starting again or from spending more time with their family, and so by having people mentor, it definitely connects them and it also allows them to become, like this, ambassador of company value. So you do want to be careful of who you choose to mentor. If you have someone that’s maybe on a negative sense or doesn’t understand the company as well, it can play negatively. But if someone is asking you hey, what do I need to know from day one? Tell me about the real culture. Tell me about what this company is all about. Like you’re effectively getting them to state your values and how you work and sort of the most ambitious part of the company which in day to day work can kind of fade away. Sometimes you just don’t come back to why you’re there. So I think having that experience is really helpful for senior leaders.


Danny Host 14:33

I love these nuggets. You think you have this podcast about mentorship and kind of cover everything, but we are really uncovering some amazing thoughts and ideas. So, ashley, thank you I know we’ve just started, yeah who have been some of your most influential mentors? Let’s talk about them.


Ashley 14:49

The idea of Mentorily and why I wanted to build it kind of came from the fact I had a pretty great career as an artist and I didn’t not deserve it, but I had to work really hard for it and I saw other people not have that career and they were fundamentally more talented. You know, I think in that industry you literally have a better physique for the job, right, Like they were in basketball it would be. They are 6’2 and I’m 5’9. There’s no, really all arrows were not pointing to me having this career, but I sort of just never gave up and was like, if I’m investing 10 years of my life at 11 years old to do this, I’m going to have a career. So I would pull people and take them to coffees and, you know, auditioning, fly to Sweden and just stay with a dancer and tell me all about this and how do I get there, and so through that I really was able to build my own career and I had people vouch for me and it’s just not what other people were doing. You’re 17 years old, you don’t know that’s required. So by doing that, naturally, I was able to get so much farther, which is why I think I wanted to build mentally to open that up to everyone.



But early on in my career I had a mentor I don’t know if it’s interesting to your audience, but he’s a pretty famous artistic director His name is Alonzo King in San Francisco, and when I moved there I had a very different view of the art form and what my career would be like and how limiting I would be in it, Because a lot of the things in the artistic world are sort of like downward pressure, they’re not upward and he gave me some really important lessons around self-worth, around happiness, around work and looking at the process as really the goal of why you’re doing something.



And those lessons I still have a notebook from when I was 17. And they have continued to be pillars and whenever I get lost I go read some of the things I talked to him about and I still see him like me and my fiance went to one of their shows when they were on tour in Montreal and he lifted out his arms. He’s this really tall guy and he’s like Ashley, you know, and so those kind of relationships. Even though it was only concentrated in the period of like two years, those lessons are still with me in my business career, in my relationships and who I want to be. So I find that he had like big ideas about the world and it wasn’t necessarily connected to what we were working on, maybe in the studio, but when you’re talking about self-worth and confidence, that kind of spans throughout your whole life, and that’s why it’s kind of funny saying, hey, are people going to be interested in Alonzo?


Danny Host 17:11

Yes, of course they are, because, like, look at these pillars that he formed for you and I think it shows you how important mentors are earlier in your life right, it’s not only when you get that first job, but even teenagers, and especially teenagers. But having those right mentors in their life can make a huge difference.


Ashley Host 17:29

Yeah, and I think it’s way beyond skill and precision of like. What is the next thing you want to accomplish? And what’s interesting is, when we were working with him, it’s very related to the physical. So if he was seeing us all look down, he would think about like are you doubting Like? Why do you not know the work enough to be inherently confident and have to like, refer to what we would call in business like your notes? But it’s the ground. What work do you have to do before you get in the studio to be confident enough so that you can show up untethered?



I could talk to my sales team about that, about like, reviewing your notes so you can show up to the sales call and be authentically yourself. And if you’re not authentically yourself, what ripple effects does that have? He talked a lot about? If I’m doubting myself, the people in the audience are worried. Is she okay? Is she confident? What’s happening? Is she acting?



No, you have to be inherently confident and aware of who you are and the information you have. And if you don’t have it, it’s okay, because that’s the journey you’re going on. So that kind of lesson for like a ballerina sure, yeah, it’s important because you have to be good at that and provide a world-class experience. But it’s more about like looking inwards and then you know how do you maintain that in every city, in every country, on every time zone so that kind of spans to when market conditions change, how do you remain confident? And when you know outside forces take over, like people quit, how do you maintain your composure? So I think mentors lessons, especially when they’re zoomed out on life. They just weave their way back into every experience you have.


Danny Host 19:01

Yeah, I’m just very inspired. Right now.


Ashley 19:02

I should text Alonso. I’m like Alonso, where are you? I should write him an email.


Danny Host 19:08

Totally. I know we’ve also spoken about your current investors. Let’s talk about how they’re mentors to you.


Ashley 19:14

Yeah, I would say that those folks, some of the relationships, change. So we have about 13 angel investors and I feel really lucky. They’re sort of like top of all of their careers. So people from you know, jad was head of security at Snapchat and Google and was the head of security there and that started his own startup. Or you know, kyle Boulay started buscom and raised you know I think 20 or $40 million and then went on to his next project. Or Brittany was the head of talent at Shopify and joined when they were like sub 20 people and took it to IPO.



So these people’s backgrounds kind of span, you know, like different levels of business. Some of them I meet with like every couple of weeks and we just have a sort of what’s on the top of your mind what is most important thing right now in the business and for you. And then others, like one of our investors, vic he’s been these like clutch mentors, like almost like emergency. I can text you at 11 pm if something is really going wrong.



The most amazing thing about being an investor is that your investment into that relationship and then entrepreneurs obviously going to pay out in a monetary way, so it incentivizes them to pick up the call, but they just go above and beyond anything you’d think. Right, like being walking you through a deal for two weeks and they’re running their own company, and sometimes I just text them saying I can’t imagine you have time for this, like I don’t just text me after dinner, before the kids go to bed and we’ll walk through it. Like they just kind of take your call and they’ve saved us probably millions of dollars and mistakes by doing that, and so when we were looking for investors, we were almost trying to. I was trying to find a mentor in every department I need, like a security person, a marketing person, an HR person, someone that represents our customer base, someone maybe that works with data and AI, so that when those questions come up, you have someone to call or they know someone to introduce you to. So my investors have been really supportive.


Danny Host 21:07

Yeah, I know it might be cliche, but it like reminds me of Shark Tank, right, like you can get money from anyone, but I do want to get money from the people who can actually provide value in addition to the money.


Ashley  21:17

So it’s great that you were.


Danny Host 21:19

You had the foresight to choose investors that could help beyond just that. Writing that check.


Ashley 21:23

Yeah, I would say entrepreneurship feels the farthest thing away from Shark Tank. But yes, I think the trope makes sense is like you want smart money, you want people that are going to help you and have experience.


Danny Host 21:35

So let’s talk about who you mentor in your current position. I know you’re mentoring a few programs like Revolution, her, princess Trust. Let’s talk about that a bit.


Ashley 21:42

So about a year ago I started to think how am I giving back and how close am I to these clients? And we started scaling a lot and we support two types of clients an HR use case, so within a company, and then what we call a network client. And so those network clients it’s kind of open to the public or to their community, so that can be a client like Revolution Her it’s a women’s organization to lift people up in business or startup Canada and different organizations where you can apply to be a mentor. And some of my clients, while we were talking about the product, we’re like oh, we’re actually looking for startup mentors. Would you want to join?



And in two ways it’s really helpful. One is obviously using your product every day. We use it internally, but when it’s not like real life stakes, you don’t feel that empathy as much. And then two, it’s to have recurring structured mentorship conversations. So I can feel, okay, I’m missing this in my mentor experience. What can we build to? I bet you other users will do that and so we’ll ask them those questions. And so I have a few relationships.



So one is in Revolution Her with a new nonprofit founder. She’s starting from idea, idea. She’s coming from like a very academic background, so much more data and context that I ever had to start my company with, which is cool, but it provides its own challenges. And then also with Princes Trust it’s an organization here in Canada, but there is one in, I think, 30 countries around the world and by the name. It’s sponsored by the Royal Family and so I was like, is it called the King’s Trust? Now? They focus on supporting ex-military veterans that are opening businesses, which is a really cool journey, going from that world to civilian world and building businesses. So I’m mentoring a team of two women founders in that program and I’m finding them to be really just like wells of joy within my life. I look forward to all of those calls.


Danny Host23:35

And it serves that dual purpose of like actually being a mentor but then also kind of like intel for your product.


Ashley 23:39

Yeah, we call it dog-footing. You want to eat your own dog food, exactly.


Ashley 24:40

Well, when we built Mentorley, we wanted to think about what barriers to each side endure in their relationship. And then how do we solve that? Through a product lens, and then we have a third pillar, which is the program manager. The person that’s running the program has a lot of challenges, and so this tool needs to essentially cut down on time, increase accuracy, increase data awareness and feedback.



So we looked at a lot of different problems that occur in mentorship. One is just psychological intimidation of reaching out to that mentor. Luckily, when I was young, I just didn’t have that barrier, and that could be from personality type or, I guess, confidence. I don’t know if I earned it, though, but I was just able to reach out. So having a barrier to entry in just a psychological intimidation means the mentee doesn’t know if that person would be open to mentoring them. Is it a good fit? What is their background?



I think as you get older in business, you become aware that you can gather all this information online and be prepped, but when you’re younger you don’t really know that. So that kind of inspired our feature base of profiles and mandatory agendas and having smart matching so the program manager can know that they’re a specific match. But then within that profile, can we have pictures of the mentors? They have to write an intro to their mentees like hey mentee, really excited to meet you. This is why mentoring matters to me. The fact that their calendar is linked and open, like all of those product features, are to make that mentoring journey a little bit easier. So the better time they get to the conversation they can focus.



And then, when they get into the conversation, we provide a lot of helpful things like agenda setting. How would you set a 60-minute agenda? What does that look like? Because probably, as you’ve discussed on this podcast, if you get there and the mentee just talks the whole time, is that a good exchange? If you’re doing background information and just telling them all about why you’re here today, is that a good exchange? So we help providing hey in the first 10 minutes you might want to do a bit of background and then dive into biggest challenges, what you have done to try to solve those today, what has the outcomes done, maybe discuss what you could do differently. So we try to guide those calls in an industry-agnostic way.


Danny Host 26:51

So we touched upon it a bit earlier. But what was it about your previous business mentorship relationships that inspired you to create Mentorly?


Ashley  26:59

I think the feeling that I was so lucky to have someone to listen to me and answer questions what would the world look like if everyone did? And I think that’s a very broad and ambitious feeling. But when you’re starting a startup you have to have that kind of broad world changing. What if this existed for everyone, despite of location or social circle? And then, the more integrated into the business and startup world it felt very warm intro gated, which, if you’re spending time getting into your warm intro circles like hey, danny, can you introduce me to Jeff and Jeff can get me to Rebecca Great by the time you get there, amazing, maybe that person doesn’t have that skill set. What if they could just meet Rebecca? Like, maybe she wants to mentor someone and he would be a great fit. And so if we can kind of break the barriers of warm intros, because it’s naturally going to lift people up, it’ll lift people that are kind of already in. It’s not going to really take someone that is not in that social network to their ideal mentor. So I think the goal of having that happen and how people would feel supported and less lonely and just have way more success in their life if they could do. It was kind of the idea behind Mentorley and how we could do that at scale.



And I think a very personal thing happened too At the end of my ballet career when you’re doing 100 shows a year, it’s like you on stage, if you are sick or injured, there’s no product. Like there just is not. And I was getting to the ripe old age of 30 and getting so tired and injured and I kind of thought, ok gosh, I hope I do things in my next stage that can kind of live without me, can kind of operate without my physical sweat maybe and blood, and that it can continue to scale. And so the idea of software and the ability for one program manager to open up this entire experience for thousands of other people was kind of freeing for me, like OK, I can invest a lot of time and focus into this, but hopefully it can kind of ripple out. So that was the idea behind it.


Danny Host 29:02

Do you think that’s also part of the reason why you started your own company and maybe didn’t go and join some of the other platforms that are out there? I know there’s not a lot, but there are a couple.


Ashley 29:09

Yeah Well, we started, like you said in the intro, we started for creatives and artists because that was what I was briefed with and the people around me, and then, really quickly, we moved into an enterprise product so that the program manager could affect other people. So it was a pivot to our existing product. Why did I start it? It’s a deep question. It’s always easier to be an employee, isn’t it?


Danny Host 29:34

I don’t know.


Ashley 29:35

Are you an employee?


Danny Host 29:36

No, I’m not. You’ve been both, I’ve been both.


Ashley 29:40

My parents are both entrepreneurs and I remember when I was leaving ballet they were like just be an employee, collect that paycheck. Like I remember them taking phone calls from home when I was a young toddler, running around the house and she was trying to be like mom’s on a work call. So I remember that not a lot of time and space to balance your life. But I was always interested in side projects. Even in my career I was involved in board direction development. So at 23, I was also the liaison between the board and the artists and I would sit in board meetings and things like this. I was always interested in where the money is coming from. Why are we paid what we’re paid? How could that get better over time? And I think that lends yourself to just start projects. So I’ve had a number of projects before this one that turned into a tech company, but it’s always been kind of. My natural thing is to do my own thing.


Danny Host 30:32

What are some of the startup challenges that you’re most proud to have overcome as you started back in 2017? So many.


Ashley 30:39

I think startups shouldn’t by default. They just shouldn’t exist. They’re inherently impossible. Right, like you have nothing and then you’re serving an audience that likes your thing and is paying you Like it is magical. Definitely, early funding was very difficult for us. I would say just the learning curve into what matters. I think there’s a lot of factors, that sort of push up against each other in entrepreneurship and most of them that you’re feeling don’t matter, which is not really an empathetic perspective. But once you’re in business long enough, you know that none of that mattered and some of that can feel deeply personal when you’re starting. So we pivoted, but it took a few years. I would have now looking, I was like I would have killed that after six months. Move on to the next thing. The market is not there, but early.



It was my first tech company. It’s like this big vision that I wanted to have. I thought people would get and they got it. We just didn’t get it to the scale to make a business, and that’s okay. Now myself I would go back and pivot much faster. I think, spending your money wisely and not overspending. I think when we first raised, we were like, okay, we need a UX, ui, we need a designer, we need to pump up the team, which is important, and it is the message you get after you fund raise. Now, in this new macro environment, you know that every dollar really matters. We’re on a different path to spending and we’re more focused on what is getting results. And then what can we maybe do in-house, versus spending a lot externally? Those are some of the primary challenges we faced.


Danny Host 32:12

You launched mentally and then, shortly after, whole world shifted its business model to be mostly remote. I imagine that this put a strain on already fragile mentorship relationships and structures within businesses. How did you overcome the remote hurdle as it relates to mentoring?


Ashley 32:28

The world changed. I remember us leaving our little co-working office and saying see you, hopefully in a few weeks, and then that was that. Yeah, in a lot of ways, I guess the first way was our internal team, which had always been partly in office, partly remote, so we actually adjusted really well. My most concern was for my team’s health and well-being, and their families too, that they had the support they needed. And then, obviously, with child care, we’re big in and that out. A lot of our clients the lucky ones had already been our clients. Some of we supported the city of Seattle and all of the artists in the state of Washington. They had this huge program. When the pandemic hit, all of their other programming was essentially canceled or on hold, but because they use Mentorly, that could just continue as needed. Obviously, those people are facing radically new changes no income layoffs, just life-changing things that they needed support. Luckily, we were able to support a lot of our customers through it. When the pandemic hit, we were almost pivoted, like we were almost live with our new enterprise products. We had a lot of beta clients and then that summer of 2020, we launched our enterprise product, and it actually because it was a remote first and video first. Even before video was widely adopted, people were looking to us for guidance.



There was a really interesting study. A leader at a company called the Scent shared it with me. Microsoft, because they have so much data. They looked at billions of data points and meetings and they have this global map. What it looks like is they measure bridge data Bridges between the teams and between continents and then bonding data within your physical location. Pre-pandemic, there was a lot of bridge connections. There was people flying to meetings and obviously having cross-team conversations, natural community and team building. Post-pandemic, the map looks like little chunks in each country is just that they got really close to the people around them and they stopped connecting with other people.



I don’t know if you felt that. I even felt that in my personal life like even my friend group is tighter and smaller, but there’s a lot of risks at that right. There’s a lot of isolation in that If someone doesn’t look like you or doesn’t have a similar experience. We use this example all the time like maybe you’re the first female hire and you’re alone on your team, but there is someone in the New York office or the Tokyo office that could be like a great friend and supporter, but