Episode 03: Itziar & Maite Diez-Canedo
Itziar & Maite Diez-Canedo are the Co-Founders of Via, a fantastic solution for hiring and onboarding global teams. In this episode, they talk about what it’s like as sisters leading a business, raising money as women, and how to extend your runway as a founder amidst early-stage product iterations. They talk about pivoting, about decompressing, and about the importance of trust in the co-founder relationship.
Episode 3: Show Notes (TRANSCRIPT BELOW)
Since the start of the COVID-19 pandemic, the world of remote work has had to advance spectacularly in a short space of time. One company that was uniquely positioned to help businesses during this dramatic transition was Via, an online platform that allows companies to seamlessly build remote teams across countries in 48 hours. Via was co-founded by Maite Diez-Canedo and Itziar Diez-Canedo during their time at Stanford and underwent a significant pivot prior to the onset of the COVID-19 pandemic. While countless successful businesses have been founded by siblings, it’s rare for those siblings to be sisters rather than brothers. We unpack some of the societal prejudices that female founders encounter while fundraising - as demonstrated by some discouraging statistics - and how skepticism increases when investors are faced with female co-founders, especially sisters. We hear more about how Maite and Itziar address these biases when they encounter them, and how they have been able to overcome initial ignorance or prejudice through direct and honest communication. Later, we examine some of the practices, habits, and mindset adjustments that have helped Maite and Itziar in entrepreneurship and creativity. We also take a hopeful look at the importance of challenging assumptions and how bringing playfulness to a problem can open up new possibilities. Make sure you tune in to this informative and inspiring episode to hear it all!
Key Points From This Episode:
● Get to know today’s guests Maite Diez-Canedo and Itziar Diez-Canedo, and the services of their company, Via.
● How they pivoted Via into the company from its original incarnation on Launchpad to what it is today.
● How their pivot to helping companies hire remotely subsequently aligned with some of the global changes brought about by the COVID-19 pandemic.
● Why they hired an external consultant to help them structure their pivot.
● How they used sales experiments to bolster their conviction that their pivot allowed them scalability.
● How they managed their pre-seed money and their mentality around spending.
● The challenge of managing your team and keeping them excited and engaged while you are pivoting.
● The benefits of co-founding a business with your sister.
● The challenges and prejudices that are inherent to fundraising as a woman and how being sisters can exacerbate those prejudices.
● Why explicit prejudice or ignorance is easier to address when fundraising than implicit bias.
● How persevering through adversity and prejudice can strengthen your sense of conviction that the business you’re pursuing is exceptional.
● Some of the practices, habits, and mindset adjustments that have helped Maite and Itziar in entrepreneurship and creativity.
● The importance of identifying and challenging assumptions.
● How COVID-19 has accelerated their business and some of the things they are excited about, like democratizing access to talent.
● How they find a balance between different modes of thinking, acting, and collaborating in their day-to-day work.
● How COVID-19 has disproportionately affected women due to societal attitudes and familial responsibilities.
● Why the framework of ‘leaning in’ as a woman in order to blend into a male-dominated work culture is limited and problematic.
● Why we need alternative frameworks for women to thrive in male-dominated spheres.
● How to identify whether you have an ‘idea problem’.
Tweetables:
“I think what you look for in a founder is alignment on – I’ll speak for myself – on values, alignment on vision and trust, right? Who better than that than your sister?” — Maite Diez-Canedo [0:12:13]
“I think with a sibling, we’ve been practicing for 30 plus years how to disagree. It’s very easy to disagree, but there’s also a lot of resilience. Even when you’re little, you fight and then one second later, you’re best friends.” — Itziar Diez-Canedo [0:14:21]
“As we have seen explicitly and implicitly, it’s harder to make a bet on a female sister founder team. It makes you take less for granted where you are, and what you’ve done and have even more conviction on what you’re doing, which in many ways I think is positive.” — Maite Diez-Canedo [0:25:25]
“The expectation that you’re pouring literally every living second into the company, that’s not – I think it’s a harmful stereotype for many reasons, life stage is one of them. But also, it’s about working smarter and with more leverage, not harder.” — Itziar Diez-Canedo [0:38:58]
“I think this idea of 'leaning in' to kind of camouflage yourself in the male prevalent workforce was something that didn’t resonate with me and that I struggled with.” — Maite Diez-Canedo [0:39:55]
“Oftentimes, I try to break out of thinking like, things are hard or work is – problems are difficult. If you try to change the lens and say, ‘How do I bring more lightness?’ What if we have a brainstorming session about this? I think that naturally unlocks more solutions.” — Itziar Diez-Canedo [0:44:45]
Links Mentioned in Today’s Episode:
Itziar Diez-Canedo on Linkedin
EPISODE 03 TRANSCRIPT
[00:00:00] J: I think it’d be interesting to hear maybe just one minute background on your current business for folks who might listen in the future, who may not be familiar with Via.
[00:00:10] MCD: Of course. We are a digital employer of record platform. We help companies build teams in new countries, which means, we take care of all of the administrative and boring side of hiring a team from employment contracts to benefits, to running payroll, which makes it so that our clients can onboard a team in a new country in under 48 hours with our platform. Itziar and I are co-founders of Via.
[00:00:38] J: I got to say. That’s a pretty big pivot from when you’re at Stanford in Launchpad. I thought it would be a fun place to start to say, how did you undertake that pivot? Because you left the program, it’s a very successful team with a very successful direction. But then you’ve actually, you’ve morphed into something even better. I thought it would be really fun just to hear how did that happen, how did you build the conviction to move in a different direction?
[00:01:05] ICD: Yeah. Well, I think the original piece is still – has the core DNA of what we’re doing now. Initially, Via was a marketplace that connected companies around the world with talent that wanted to be based or live in different places. We saw sort of globalization speeding up, companies hiring internationally more and then the workforce wanting to live and work in different places. The solution initially was a talent marketplace for short-term work. Our first pivot was realizing that companies is more of a vitamin than a painkiller, right? Companies really wanted to find permanent teams to help them take their company forward. We pivoted in a way to help companies with full-time hiring, and so became the international hiring partner for hundreds of companies.
In doing that, helped them hire their first team in a new country on many occasions or hire team members abroad. That’s when we realized what a huge pain point it actually is to hire someone in a new geography where you don’t necessarily understand employment long or you might be getting into unwanted risks and where basically companies global mindset expansion and the reality of making that happen was a very big.
Then COVID happened, which obviously brought to the forefront these trends and really change the mindset of many companies to all of a sudden be much more open to hiring remote or distributed, whatever that means for a particular company. That’s when we decided that this was such a paradigm shift in the future work and we were so well positioned, and have been seeing these insights for such a long time that we decided to focus 100% on solving that problem.
[00:02:51] J: I want to dig in for one second about how you operationalize that decision, because I remember, it was probably one month before COVID that we sat outside [inaudible 00:02:59] school, eating the free lunch on a Wednesday and you were talking about, we have this business but we see this other opportunity and we kind of explored what that might look like to try to maybe conduct them both in parallel, maybe split up. How did you actually operationalize the transition between US founders or as the organization as a whole?
[00:03:24] ICD: Yeah. It’s very hard to do things two things at once, right? Focus, focus, focus is a huge part of just really deepening your learning and they were too fundamentally different businesses. We quickly realized that doing both wasn’t sustainable. Tactically, what we did was sort of structure how we were going to make this decision and what proof points we needed to be sure that we are going to go this route. It started with different sales experiments that we already had some services, solutions that were in line with the new business and so we doubled down on that and measured sort of traction. We got more confidence in that we could sell the new set of solutions. Then over a couple of months, we actually brought an external consultant to have an external perspective and help us really structure the pivot and make the decision in a more structured way, if you will.
It helped having an external sort of coach consulting come in working with both of us because there’s a lot of legacy over a few years of looking into a problem in a certain way. Stripping that away and sort of seeing the problem and the opportunity with fresh eyes really helped us sort of make the decision. Then there was a day when we made the decision and a few days when we called clients and said, “We don’t do recruiting in this case anymore.” When our pipeline was all of a sudden dry, that’s what really made us hustle to sell the newer solution.
[00:04:54] MCD: And you have to get comfortable, like have enough conviction where you’re comfortable with basically clients being bummed out that you no longer do recruiting. Some of them were very happy because they saw the potential and the new service as well and some of our clients now. But you also have to be okay knowing that we were doing a pretty good job of being recruiters and telling them that we can no longer help them find their product manager in wherever. We have to have a lot of conviction with your clients and with your team as well to say, “Hey! We had hired you initially to be part of the marketplace and now, we’re doing something different.
[00:05:28] ICD: The team had to change as well, so we had brought on people in the HR space. We had to restructure our team. We had to be very honest and say, if your dream was to continue solely in this more traditional side of HR, this is no longer the place for you. That was also part of the shift.
[00:05:46] J: You’ve just given us breadcrumbs for – Mar, how much time do we have? Do we have seven or eight hours here? Because there’s so many [inaudible 00:05:54] directions we could go and I have one question and then I want to pass it to Mar and see where she’s curious too. One of the words you use was conviction and that’s a really important word for founders. As you all know intimately well, in Launchpad, we talked a lot about experiments being the means by which we gain conviction. You had used a word, [inaudible 00:06:13] that you had commissioned a bunch of sales experiments to start to grow in conviction.
I wanted to hear, how granular do you get? When you think about sales experiments and you said you’re seeking to hit certain goals before you had the conviction. How granular do you get about crafting those and scoping exactly what you’re measuring, how you measure it, what the timelines are before you execute the experiment?
[00:06:39] ICD: We probably could be more structured because sometimes the metrics that come out of the experiment are different than the ones we are looking for. But we do have sort of time to limited sprints, if you will. In this case, it was selling the mobility solutions to a set of clients in different segments and understanding what the sales process could be, what the onboarding could be. Then in hindsight looking at that, what was clear to us versus the old business with scalability. We could do in doing it, in selling it and in onboarding several employees. It was very clear that we could do that a thousand or 10,000 times using the same process.
Where obviously, what we were doing before was not as scalable in the way that we were doing it. That was the outcome metric if you will and we had to sort of actually do it to realize how scalable it was.
[00:07:34] M: Yeah. Maybe I can double tap on that because I think one of the things you guys did, I think you raised an initial pre-seed round. That was maybe like around a million dollars if I’m correctly roughly. I think a typical company that raised money, the first thing they do is go out and spend it, maybe get a fridge full of coconut water, I say. You guys were very – you didn’t spend a lot of that money. Every time I would see you, it seemed that you still had one million dollars in the bank, so this allowed you to do a lot of experiments.
I’d love to hear, what was the thinking behind that because you didn’t go off and hire six people all the way. I mean, all of a sudden.
[00:08:15] MCD: Yeah. I mean, we knew initially we raised the pre-seed round – first of all, we’ve always been very cautious about – in life, super scrappy, that’s for sure. Come from an entrepreneurial family where our father started his business, boot strapped, and so the mentality is very different than venture, where you have to kind of go out, not really knowing whether you’re going to be profitable and spending a lot. But I will say that we were very clear in the initial business model that are existential or I guess, the question we were answering was, is there a market for this and what is the pain point, which is a different question now around like more execution. We’re in a position where once we saw product market fit and once we saw this concept of recurring sales and scalability. Now, we’re in a position to fully invest in our team, and grow our team.
Before then, it was, “Hey! Let’s make sure we find something that is actually, first of all, a painkiller track line. Second of all, a scalable recurring business model and then we’ll go all in.” Thankfully, we did that because if we would have hired a team of 25 people and finished our pre-seed round, we wouldn’t –
[00:09:21] ICD: We wouldn’t be here.
[00:09:21] MCD: We wouldn’t be here.
[00:09:22] M: We have to commend you on that, because the two of you are so impressive, that you can raise money without having product market fit, but realizing that you don’t have it, it requires a certain level of maturity and intelligence, I guess that you guys did have. Yeah, that was very impressive for working with you guys.
The other question I had is, obviously, it took a while and this is what you don’t know. It may take six months to find – make it six weeks, six months or two years. I was just coming from another meeting with a similar founder. It took me three years to figure out what it was. And you change, and how do you manage your team because your team may not be aware that that’s where you are and you have to keep them really excited, and you’re pivoting and changing. You still need the strength of your team behind you.
[00:10:10] ICD: Yeah, I think several sort of moments, humbling moments at least for me as a manager is realizing that as a founder, you’re sort of sometimes over your head with so many things you have to figure out and you’re driving the ship. In doing that, you’re securing the job of the team, right? There’s an inherent sort of responsibility and focusing on getting the company to move forward. But that’s not an excuse for, right? Not dedicating the right time, one-on-one’s touch points and understanding psychologically, motivationally how every single team member is doing.
We do have sort of the check-ins, the one-on-one feedback sessions. But it’s easy to get carried away with trying to make things work and not realize that there’s no excuse, you’re a manager first oftentimes, right? Because without a team, there’s nothing. It’s putting in that discipline and understanding that others are looking to you sometimes. Especially in this remote world and with COVID, that’s even more of a bonus, right? That’s something that we just put on the calendar, fixed and we come back to, because it’s just a crucial part of making the company successful.
[00:11:23] M: Yeah. I want to ask you a couple of questions just because you’re a special team, I would say, that I don’t see often. You’re sisters, you’re both female founders. I don’t know if you have any stories, I think this will go somewhere. We don’t know exactly where it will go, but somewhere. I think I do get – I think sometimes family starts companies together. Is that good or bad? Your insights for anybody that wants to do that. Also, being two women. How do you think that helped you or not? But I think it’s a plus.
[00:12:01] MCD: Yeah. A lot of things to talk about there. On being sisters, it’s always kind of funny because it is what it is. You don’t have the countereffects, like we are not not sisters. It’s kind of like, “Yep, we’re sisters.” I think what you look for in a founder is alignment on – I’ll speak for myself – on values, alignment on vision and trust, right? Who better than that than your sister? As opposed to saying, either of us had been at Stanford and we were in a class with some person who was cool and we ended up being co-founders. It’s like a very intense relationship that you’re starting.
We know each other very well, we know our strengths really well, we know our weaknesses really well. I think we’ve done a really good job at separating the personal side and the professional side and working on that relationship too is critical. Especially if there’s more weight to that relationship, the more you have to work on it to make sure that it’s effective both for your professional life and your team, as well as for your own sister relationship when you’re out of work, even though these days were not really out of work.
[00:13:08] M: If you go have dinner at Christmas at your family, is it okay to talk about Via or not
[00:13:13] MCD: Absolutely.
[00:13:15] M: Yes.
[00:13:17] MCD: Yeah, absolutely.
[00:13:17] ICD: Sometimes we don’t want to talk about is, so yeah.
[00:13:20] J: Is there a boundaries question there? Just to follow up on what Mar was asking. Are you saying sometimes you don’t want to talk about it? How do you keep it from swallowing your whole life when your sister is your co-founder and when you’re together, how do you set boundaries?
[00:13:37] ICD: Yeah. It’s funny that we also both look for a respite from work and our friends, first and foremost. If someone wants to talk about something, we bring up the conversation. But there’s always the option of saying, “Let’s tackle that in another moment.” It’s also the only person that really understands your experience and so it’s the best person to sort of vent, or analyze or reflect. So that can also be restorative in a way. It’s just having the right, clear communication to say, “Hey! I don’t really feel like talking about this now” or finding the right time to have those deep conversations, but it’s pretty fluid. I think with a sibling, we’ve been practicing for 30 plus years how to disagree. It’s very easy to disagree, but there’s also a lot of resilience.
Even when you’re little, you fight and then one second later, you’re best friends. That resilience really brings a lot to being able to say things as we feel them very directly and then being able to just very quickly bounce back and focus on the task at hand with no sort of emotional hangover, if you will, after any sort of disagreement or discussion. That resilience I think helps the sustainability of any relationship.
[00:14:58] M: Maybe we can talk about being a female founder. If you have any anecdotes or anything you want to say. I know very little of our venture money goes to women. I haven’t been on your side of the table for a while, so I don’t know if you have any, like I said, anecdotes or anything that you would say to other female founders or your past selves.
[00:15:20] MCD: Yeah. I mean, I think one is like the sad reality I think that – I mean, Mar, you were saying, I think it’s a good thing. But if you look at the numbers, it’s clearly not a good thing, because 2% of venture goes to women. Less percent of that goes to like two women founders.
[00:15:35] M: Yes, that’s very rare.
[00:15:36] MCD: Less goes to sisters and the sister comment, we got that a lot when were fundraising actually the first time. Like this concept and maybe the stereotype that like when I say brothers versus when I say sisters. The sisters concept in some people’s minds is like, “Oh! That’s cute.” Right? Like it’s a sweet sisters – all these stereotypes that we have, right? Some investors in our pre-seed round –
[00:16:00] M: I hadn’t thought about that, but brothers versus sisters, yes.
[00:16:04] MCD: Right. Like there are multiple companies that have been started by brothers that no one –
[00:16:14] ICD: Most of the companies in the world are family businesses by the way. It's usually [inaudible 00:16:17]. Siblings running a company is actually a super common thing. But sisters for some reason is seen as something rare or different.
[00:16:28] M: Totally.
[00:16:28] MCD: You have to come at those conversations with again, like it is what it is. Like embracing your difference and knowing that the numbers are stacked up against, but finding a way to either not – for me, a mechanism is like not even thinking about it, because then you kind of get into this rabbit hole of trying to see with this lens of how people are perceiving you as a woman. My mechanism is like, not dealing with that in a way, if that makes sense, like not assuming the role of gender when I’m in a pitch. But inevitably, that comes up.
The first time we were fundraising, it was in the middle of Me Too Movement in late 2017, early 2018. A lot of the – there was tension in venture obviously because there were a lot of names coming up from investors and things like that. So there was a tension around our fund raising process that probably made male investors more uncomfortable, because we were females obviously and we understandably – yeah, how do you deal with that? It is what it is, right? Trying to not let it affect you that much.
[00:17:38] ICD: I think there’s two sort of the visible moments, the tangible moments that you can react to and that you can show up for and respond to. Those in a way are easier, because – in the wine bar with an investor. [Inaudible 00:17:54], I’m sure you remember who questioned that. My job is pattern recognition and I really haven’t seen much sister teams, so seeing it as sort of a negative on our prospects of success. It was an email that I wrote up late at night with proof points of how actually sibling companies and why we’re separating out the sisters. That was a chance to react and I got a very humble respond to saying thank you. I just learned something, and you’re totally right and you caught a blind spot.
Another example of that was, another investor conversation saying – this was an angel with a smaller amount of companies saying, “You are the first female-founded company that I invest in out of, I think I’ve funded 30. I really want to invest in female founders, but the diligence that I did with you is longer than I’ve done for any of the male founders.” He was being very transparent. “Because I haven’t invested in female founders and I’m so excited to invest in female founders that I feel like I have to do more diligence.” I didn’t quite understand the connection, but that was pretty explicit. Our response there –
[00:19:02] M: At least honest.
[00:19:05] ICD: The response there was, “Okay.” You recognize there’s more hurdles and the response was a frank conversation and it ended up turning into a great relationship. The trouble is when they’re invisible. That’s when you don’t want your mind to go assuming. I don’t believe in being the victim, because that doesn’t really serve you, but it does serve to understand what might be happening. For example with our own team, giving feedback on expecting more warmth in communication. Then it’s openness for it. You had to dig to get to that answer, but it’s saying, “Hey! My communication is clear and direct and there’s nothing wrong with that. My objective is not to be perceived as nice.” It’s working through that, not changing your style but knowing that it’s going to land differently on different people.”
Then just knowing that there’s these undercurrents. But if you can’t control them or you can’t unearth them, then not letting them get in the way of your success, because I think one thing too is, on top of sort of making our company very successful and that drive there I feel an added sort of motivation to be and create more role models in our demographic and prove people wrong. There’s an added drive and that’s certainly a positive.
[00:20:28] MCD: The founder Bumble, I forgot her name, who IPOed.
[00:20:31] ICD: Whitney.
[00:20:32] MCD: Whitney, and then the same for Stitch Fix, Katrina. The famous picture of the IPO woman carrying her baby, which is – like whole ton of like things to say about that and that as a symbol, but it’s also like, you’re still carrying the symbol of being a mother when you are IPOing. Whereas, if you’re a father, you’re not with –
[00:20:55] M: Nobody brings their baby.
[00:20:55] MCD: Right. Like there’s a lot – you could say it both ways, but I think it’s constantly on our mind of like, what is the example that we want to show. And Mar, I think you’re an awesome example of that, of like, yes, being a mother and having a family, and yes, being a rock star professional. That’s not – it’s harder to find. Being role models for that is an added –
[00:21:17] M: I do think – I mean, there’s data behind that. It is harder for people like you guys to raise money. I think for you it’s double hard, because of the sister thing. Only rationally, I think there’s all these biases and even, people are conscious or subconscious of them, but they exist. Where I was saying that is an advantage is, the way you run the company, I think you’re conscious of your limitations more than a traditional male founder. I think that’s partly what has helped your success. At least, that’s from my side, that’s what I would deduce, which –
[00:21:52] J: Could you say more about that? What do you mean conscious of your – how have you observed that or how do you all interact with that observation?
[00:21:58] M: Is that a question for me, Jeremy?
[00:22:00] J: Either. Oh! Sorry, yeah. I mean, Mar, I’m curious, what you saw that made you feel that way and then Maite and Itziar, if there are particular ways you’ve processed or attempted at that. I’d be curious to hear.
[00:22:13] M: When I mean conscious and subconscious, there’s a lot of subconscious bias, right? I mean, I think we all work with amazing – even ourselves, we are biased right. To your point, who has heard of sister and co whatever plumbing. Not many people. It sounds weird whether you’re female or male. Even if you don’t want to, it’s in your psyche and it’s hard to get out of it. That’s what I meant by subconscious. Some people, like your angel are able to say, “I haven’t done it, but I want to but I can’t” and they’re kind of almost fighting with that. I would say in that case, he’s conscious that he knows it does exist.
But I think, I don’t know what you call it. Maite or Itziar, you guys called it the bias you cannot see. I think that’s the –
[00:23:03] ICD: Like a blind spot. You’re totally right that you have your own – part of it is doing work on yourself and understanding what are the rules that I grew up with, how is that different, what are the women in my life that have shaped the expectation of what I should and shouldn’t do. That’s a whole sort of work in and of itself. But it’s bringing it up, being aware, raising consciousness and talking about it. Something important is keeping hope and optimism versus carrying a burden of lament for victimization, because it doesn’t help anybody.
[00:23:43] M: I think it’s interesting because you guys are such great presenter, and speakers. And when you present your company, I think you take the listener with you. You’re really, really good at that. You have something that very few people, male or female have, right? I do think that the tone and the spirit in which people speak is actually perceived very, very differently if you’re female and male. A lot of that is subconscious. It happens to me all the time in board meetings. If I say, “This is wrong and you’re not doing it right.” People will say, “Oh my gosh! She’s such a b—. She’s terrible.” I’m like, “No. I’m just saying what’s wrong.” But if a guy said it, it’d be like, “Wow! He knows so much about business.”
[00:24:25] ICD: Totally.
[00:24:26] MCD: All the time.
[00:24:27] M: Which I think when you’re fundraising and you’re in a sales mode, it’s harder to actually have the right tone and not call somebody aggressive that people don’t want to work with. You may not have seen it, but it’s on the other side, I know.
[00:24:43] UNKNOWN: Yeah, for sure.
[00:24:43] MCD: No, [inaudible 00:24:43] balance all the time.
[00:24:44] ICD: It’s being strategic while still being authentic, right? That little things like women on our team that put too many exclamation points on emails or too many [inaudible 00:24:55].
[00:24:56] M: Yes, or emojis.
[00:24:56] ICD: And coaching and saying, “You don’t have to be overly nice. There’s no objective and that you’re going to be polite, and clear, and kind always.” But you see the difference and so there’s easy fixes of style that make you more effective. Then there’s testing it too, and hopefully getting feedback from trusted mentors and partners on how you land, how you come across.
[00:25:22] MCD: I think, knowing that your benchmark in many ways is higher, because as we have seen explicitly and implicitly, it’s harder to make a bet on a female sister founder team. It makes you take less for granted where you are, and what you’ve done and have even more conviction on what you’re doing, which in many ways I think is positive. We’ve known of companies in the same space raising 10 times more the amounts that we’ve raised with the same amount of traction and at the same amount of revenue. That just gives us more conviction that we’re on the right track. To get to where we are now, being a sister female founded team, immigrants, we’re not Americans. There are all these things that have been put on us, if you will. Also, a ton of privileges. We went to Stanford, and that’s not, again, not trying to be the victim in any way but saying, “Hey! If we’ve come this far, it must because we’re onto something big. Otherwise, it would have been easy to do this.”
[00:26:15] J: One of the things I’d be curious about is, most of this conversation has focused on entrepreneurship and being a female founder. As a part of the impetus for the conversation is my own challenge, and blind spots of ignorance. I’ve got four daughters who I want to support in all the many directions they want to go.
[00:26:33] ICD: That’s awesome.
[00:26:35] MCD: So lucky.
[00:26:36] J: I’d be curious what you – Mar got into this a minute ago, but I want to put a fine point. What would you say to somebody in your position? How do you think about cultivating habits of mind? Set aside entrepreneurship for a moment. Think about creativity. Think about curiosity. What do you think – what are the habits or the practices that you engage, or that you found looking back, you engaged as you went on this journey to increase your likelihood of fresh discoveries, and new ideas and unexpected connections? Going kind of from entrepreneurship down almost to creativity and down to a very kind of personal practice, what would you recommend somebody like me or my daughters or young women? What habits of mind, and attitudes and interactions should we be cultivating that might lead to an entrepreneurial or just a satisfying and fulfilling professional life?
[00:27:32] ICD: That’s an interesting one.
[00:27:33] MCD: What comes to mind for me is like the belief that you can and I think this is a lot of our parents or at least the influence that they had on me is, you can do whatever you want to do and being super confident and building that confidence with whatever things make you feel confident in yourself. Whether that’s sport, whether that’s art, whether that’s doing really good in school. Whatever builds your sense of confidence, I think, if anything as a woman is even more important to make you embody that belief that you can do it because it takes thicker skin to put yourself in front of a board room full of man. Or in my case, I started my career in banking in Wall Street with all men and they didn’t even know where the women’s bathroom was when I started. I guess that comes from growing up having the confidence to know that it’s okay and you can do it. I would put that all on our parents, I think growing up.
[00:28:27] ICD: Totally. Building that confidence and also what came to mind is questioning. Having a mind cycle of questioning your own beliefs, beliefs that others have about you, beliefs that society might have or expectations. Because at the end, those beliefs are hanging onto a value that might not be true to yourself and your capability. If you have the practice of questioning things that are said to you or labels that are put on you. And the fundamental understanding that most blockers are in your own mind and you can sort of break those apart, I think that’s very powerful.
It’s easier to put the blame externally, but if you really do the internal work of saying, “What are the beliefs, conscious or subconscious that I have been sort of carrying that make me think that I can’t go for the soccer team or that I can’t be successful in this position?” Then when you really hold yourself to that answer, you realize a lot of that is just BS. That helps with creativity too, because creativity is what is possible, what can I create, what can I do, is this a crazy idea, am I out of my mind. There’s always insecurity that sort of blocks creativity, so questioning that and breaking that part.
[00:29:51] J: When you said, I love that – I wrote down, having a mind cycle. You used the word practice three different – I was telling, three different times right there. What is the practice? Because to me, that’s actually an unlock, man, woman, boy, girl, child, adult. How does one question one’s unknown assumptions? Do you have a practice for that? Because to me, it’s like even – like I love making – my girls and I love creating riddles. What I’ve discovered, this isn’t like scientific. My observation is, the key to unlocking a riddle is questioning your assumptions. When does Christmas come before Thanksgiving? In the dictionary.
My assumption is, we’re thinking in terms of time. The moment I realized there are other ways of ordering besides time, then – but the point is, what I find is really difficult is, if you ask me that joke and I don’t know the answer. Then you say to me, “What are your assumptions about the question?” I haven’t found a way to go, “One of my assumptions is I’m thinking in terms of time.” If you ask me to list the top 100, I don’t often find the operative assumptions that deeply embedded. So I am all ears if you have practices or ways of interacting with that, because I feel like that’s an enormous superpower that is hard to get at.
[00:31:14] ICD: I think it’s being a rebel almost internally, trusting your intuition and questioning what’s put in front of you. Always asking why and there’s the famous, if you ask why five or six times, you get to the root of it. This sometimes plays against me when I question too many things and we need to make a decision and move forward. It’s just something that I have, but it helps in saying, if there’s a feeling, if there’s a strong feeling, that’s sort of a first hint and then sort of, why am I feeling like I’m not up for it or that this isn’t for me. Why do I think I feel this way? And sort of reflecting and questioning until you break that apart?
For me, it’s more of a reflection process of asking questions and not taking things as fixed or taking things as given or why is this expected of me, or why is my team member asking me to be warmer in my communications. I mean, look through the last couple months. Let me understand this. I think in doing that when you can unpack things that might not be initially visible.
[00:32:19] M: I just think when you guys are working, it’s so exciting. COVID changed the world in so many ways or accelerated the world or brought the future. I don’t even – it’s hard to find the words, but I think one of the things that have changed the most is how people work, where do they work. When you’re building a company, how do you think of your workforce. I’d love to hear what you guys are thinking in terms of what the big companies look like in 10 years and Via has a place there? How you guys are going to dominate the world?
[00:32:50] MCD: Yeah. I mean, when you think about that all day, I think it’s fascinating and it’s only just getting started. COVID accelerated a trend that was already under way, but brought us 10 years sooner. We see in our abstract vision is a lot more fluidity and less barriers to building a team globally. First of all, because it will be a necessity to compete at a global level with global talent and because of how things are so interconnected, which was another one of the big learnings of COVID on a global level. But to enable that through and we’re an enabler of that fluidity if you will, of having talent connect with opportunities wherever physically you are and that wherever you’re sitting physically shouldn’t be a barrier to where you’re working, who you’re working for. There’s a lot of like democratizing access to talent that we’re passionate about.
Via means a bridge, or one way to another, which is exactly how we – what we think we’re doing in helping people connect to the opportunities and companies connect with global talent and making that seamless in a world where barriers are real, and borders are real and there are legal constraints to hiring people in different markets. But to the extent that Via can be the solution to that from a product perspective, from a financial perspective, from an admin perspective and do it all on a beautiful platform, that’s where we want to be. There’s a lot more than just being the digital employer of records today. I think in the future, what we become is a platform that integrates all of the things that are relevant behind the employment of a person. You can think of things like benefits, carrying over and having the best benefits on the ground wherever you are and how those carryover, an employment powered by Via in multiple countries around the world.
[00:34:39] M: I like that, employment powered by Via.
[00:34:43] J: One of the things you talked about was focus, focus, focus, focus, focus, focus. One of the things that I’m always struck by is the paradox between the connection and disconnection. The importance of focus and being open to inputs. Do you carve out time for both? How do you create space for different modes of thinking, acting, collaborating in your day-to-day work?
[00:35:13] ICD: Yeah. I think there’s different rhythms when you’re in fully executional versus when you’re brainstorming and you have to find a good balance. I think the way we like to think of that is having strong convictions loosely held. We are going all in on a certain path, but if there is enough data, or insight or something comes up that is worth taking a pause and reflecting on, then we’re open to that. We create the space for that. We also think that in executing and in doing, the bias towards action that is so ingrained in the Launchpad philosophy. In doing, you find out a lot of data so there’s not usually a lot of use in stopping and over analyzing things. But pausing, seeing the situation and then running experiments to see if your conviction was true. Managing those two speeds and finding a healthy balance of pausing to reflect, and question and then focusing on execution.
[00:36:18] MCD: We need a refresh around Launchpad, Jeremy. That would be awesome.
[00:36:21] M: We need that Launchpad along.
[00:36:22] MCD: If we could have that structure again.
[00:36:49] J: Is there anything that I should have asked that we haven’t asked yet, in terms when you go back to the frame of female founders, entrepreneurship, creativity, innovation. Is there anything else that you have come to believe or hold deeply that you haven’t been able to express or that you want to add?
[00:37:05] ICD: I think one topic and it depends maybe age wise and who the founders are. But one of the big things that has come out of COVID and working at home is how much harder it’s been on women more from a family responsibility perspective. That’s something that even though [inaudible 00:37:22] and I don’t have children now, it’s something that you see in your immediate future and it has a very different implications for men and women obviously. That plays into your lives as founders too. I think just the family aspect of it is always something interesting to bring up, especially since it had more of an impact on women during COVID and taking more of housework or childcare, et cetera. Yeah, that’s one topic that I think is important.
[00:37:51] J: It kind of reminds me a little bit. I was just reading Ed Catmull’s book, Creativity, Inc. about Pixar. One thing that he was saying, they found that they have to be careful because younger employees have more ability to be absorbed in work. Whereas, older employees have families, other responsibilities and they have to be careful not to disproportionately punish family life. It’s easy to unintentionally reward people who pour themselves into work and there are some very valuable employees who can’t pour themselves in the way. It strikes me, there’s a little bit of an analog there, between age, and life stage and the male-female work-life balance and expectations. But it seems to be the fundamental question is actually the same one of how do we support folks as their life progresses at life stages.
[00:38:44] ICD: At different life stages. Interesting, totally. Having that, yeah, that stereotype of the entrepreneur that is, or the founder that doesn’t sleep, which is ridiculous because that’s also a key to creativity, is sleeping well. The expectation that you’re pouring literally every living second into the company, that’s not – I think it’s a harmful stereotype for many reasons, life stage is one of them. But also, it’s about working smarter and with more leverage, not harder. It’s not necessarily correlated, the long hours into the night and burnout with multi-year or decade career in entrepreneurship. It just doesn’t hold.
[00:39:26] J: Maite, I don’t know if you wanted to add anything to the last question. I had one more just short question to ask, but I didn’t want to rob you of the opportunity to answer if you got a big thought you wanted to leave with.
[00:39:38] MCD: Yeah. I think what was coming up for me as you were saying it, is like this concept of lean in that was very popular during my few years – for the past years as I was starting my career, regardless of whether you’re a founder, just starting a career as a woman. I think this idea like leaning in to kind of camouflage yourself in the male prevalent workforce was something that didn’t resonate with me that I struggled with. I guess what came to mind is like creating new titles, or frameworks or as you said before, practices that resonate a little bit more with at least – what it felt like for me, the lean in framework didn’t resonate with me. I found it hard to – but there aren’t other frameworks that you can call on or practices.
The more that we can have these conversations that generate more ideas and more frameworks, and more things to talk about, I think that’s the key. And having groups of women who get together and talk about these things, whether your sisters or not with men is key at all levels.
[00:40:41] J: That’s good. the last question I was curious about is, how do you know when you have an idea problem? Meaning, [inaudible 00:40:49] a second ago you said, when you’re brainstorming, it calls for a different mindset, da, da, da. What trips the wire that different mindset is needed? You know what I mean? Because the default is kind of convergent thinking and eliminating options. What makes you go, “You know what? We need more ideas.”? What does that for you?
[00:41:14] ICD: When an idea isn’t or what determines whether an idea isn’t good enough or once you’ve converged that you actually need more ideas or at what point?
[00:41:22] J: It could be at any point. I mean, to me, I will say for myself, not to give away the answer or anything like that the vast majority of problems or idea problems. Subject line to an email, that’s an idea problem. How to frame the conversation, that’s an idea problem. My problem is, oftentimes, I don’t realize the challenge I’m wrestling with is actually an idea problem. Because when I see my challenges and idea problem, the toolkit that I can draw upon expands dramatically. Because I know how to solve idea problems, my challenge is, I’m not seeing where we go to dinner tonight as an idea problem. I’m seeing it as a, just make a decision.
I’m always curious about – I ask this question of a CEO of a big, Fortune 100 company and what he said to me was, “Every meeting I go into and I have three or four bullet points of what I know I want to express in a meeting.” He said, “When I pull out my notebook and I don’t know what to write down, that is what triggers the alternate pathway.” For him, it’s meditation that he takes. But I was just curious, like what is the moment that you go, “Oh! I need a different set of tools here” or if you have a recent example maybe. That might be more helpful. But that’s kind of what I’m – that’s an area of personal –
[00:42:39] ICD: You just made me think of five problems that I haven’t been able to solve, but now I realize that we should do a brainstorming for. No, you’re right. Especially when you’re in execution mode, you see it as the same type of work, where you’re coming up with the answer or coming up with the decision. Yeah, I don’t have a good answer for that, but you just made me reflect that we should have more brainstorming to write down some of the things that we’re stuck on. Maybe it’s when you’re stuck on something or when there’s a disagreement about a particular decision or when a decision isn’t flowing and isn’t clear and it’s hard for you to think of the next step. When you’re procrastinating, that sometimes is a good sign of why aren’t you doing something, that mean there’s some resistance, something is not clicking on the next step. Maybe the solution that you had thought isn’t the right one.
[00:43:29] MCD: Or when things are being more repeatable, I guess we’re really good at being very action driven and executing a whole bunch of things. But when we have to go build this massive vision, I guess what’s coming up for me is like, if you’re doing things that seem to be pretty much the same as what you’ve been doing for the past two weeks, even if those are good things, just taking a step back and saying, maybe we should think of new ideas to do – what are we not doing a little bit [inaudible 00:43:57].
[00:43:57] J: Yeah, that’s great. For me, it’s similar to the question you’re talking about earlier about assumptions. How do you know you’re making an assumption? There’s a similar kind of a cognitive block I find, when we realize. I didn’t realize I was trying to - I was thinking about this problem in the wrong way. If there was like a simple kind of reframe or for whatever reason, even the prompt, even just me saying, it sounds like. You’re even saying, when do you know you have an idea problem. All of a sudden you go, “Oh! I have a bunch. I haven’t been thinking about this idea, problems. But why don’t we, I don’t know.
[00:44:38] ICD: Yeah. Something that comes up too is bringing in lightness and fun, trying to do that as a practice into your day-to-day work. Oftentimes, I try to break out of thinking like, things are hard or work is – problems are difficult. If you try to change the lens and say, “How do I bring more lightness?” What if we have a brainstorming session about this? I think that naturally unlocks more solutions. Trying to keep that playfulness almost of having fun. You’re in these hours upon hours every day and part of the job is bringing in that enjoyment. I think with that naturally and that play mindset naturally will come more open as to sort of turning something on its head or thinking of something crazy because it’s not really going to break anything.
[00:45:31] J: I like that. It’s not really going to break anything. We often say, to folks who are worried about running an experiment, you can’t do irreparable harm. It’s nice.
[00:45:43] ICD: Thankfully we’re not surgeons, or doctors. So yeah, for sure.
[00:45:49] MCD: We can’t really break anything.
[00:45:51] J: If folks want to find out more about you, where can they go? Twitter, LinkedIn, the inner webs, Instagram. Where do they go to learn more?
[00:46:02] ICD: We’re doing a rebranding of all of our platforms now. Our website, www.via.work. Then, yeah, we’ll have the other platforms up and running soon, but the website is the main thing or our email if there’s anyone interested in a specific topic, we’re more than happy to chat and we can send emails too over the chat.
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The fine folks over at Section recently interviewed me about some common mistakes I’m seeing folks make when they use AI. One of the biggest ones? The tendency to expect too little, and get just that.