Episode 2
Katharine Wolf, founder and CEO of OdettaEntrepreneurial inspiration can be found at the intersection between business and values

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Having a mission or purpose can drive people to succeed during the most challenging times. Katharine Wolf, founder and CEO of Odetta, discusses how her company’s mission makes it more than a business.

Many businesses start with a great idea for a new product. But for entrepreneur and business owner Katharine Wolf, a personal mission founded on core values drove her more than any product could.

Katharine’s brainchild Odetta, is a global network of gifted, and untapped freelancers in the growing gig economy. Unlike Fiverr and Upwork, Odetta is centered around a mission that enables highly educated women in countries where women face constraints in the job market due to location, time, and work culture, specifically in the Middle East.

Katherine sat down with the Entrepreneur’s Studio’s host Chris Allen to share how she developed Odetta based on her personal mission to build products and services for women.

Below is an edited transcript of the conversation. In the episode, you’ll learn how to become purpose-driven and how to integrate it into your customer and office culture:

  1. Find a business concept that aligns with your values
  2. Commit to a purpose, not just a business
  3. Double down on your mission when times get hard
  4. Remember a mission is a movement, not a solo act
  5. Create structure for your mission to evolve and build a legacy

Becoming aware of gender differences at a young age

Chris Allen: So glad that you decided to join us in the studio. Super awesome to meet you and to have you here. I hear you’re a quadruplet.

Katharine Wolf: So nice to meet you. Thanks for having me. I am a quadruplet.

Chris: Yeah?

Katharine: Yeah

Chris: How did that happen?

Katharine: Fertility drugs.

Chris: OK, there you go.

Katharine: My parents had one son. We have an older brother. They were trying to have a second, and the doctor called them and said, “You’re having twins,” and then said that you’re having triplets and then said, “You’re having quadruplets.”

Chris: Oops.

Katharine: Oops. All of a sudden, they had five kids under the age of two, which sounds terrifying.

Chris: Totally.

Katharine: So we were known as the wolf pack growing up. It was actually really fun.

Chris: That’s great.

Katharine: We have this amazing footage of us just kind of ... My parents would put us in this fenced-in area and pour Cheerios on the ground. It’s just like all of these kind of like little kids running around animalisticly eating.

Chris: That is amazing. What did it feel like growing up? Was it just like you had a close comradery with your brothers and sisters?

Katharine: Yeah. Well, I was actually the only girl. So I have an older brother.

Chris: Oh wow.

Katharine: Then there are three of us in the set. Yeah. I mean, we’re still really close. It’s pretty special to go through life, doing the exact same thing at the exact same time. I’m sometimes jealous of single births that they got to have that experience with their parents, but we had this whole crew. We’d always play football together or whatever. I was a total tomboy.

Chris: Totally. OK.

Katharine: Yeah.

Chris: Well, that’s good. How do you feel like that experience affected you professionally?

Katharine: I think it did affect me professionally quite a bit, obviously, when you’re in a set of quadruplets. I was forced to learn how to be self-reliant very early on, and I had to fight for my rights and quite literally my space from the womb.

Chris: Are you competitive?

Katharine: I am pretty competitive. I’m both, but I think I had to be to survive. In our family, you probably have this with your kids, but it was really important for us to all be different. It was this really intense desire to be unique. So I spent a lot of time trying to figure out, OK, I’m the only girl, but what else am I? What are my strengths and weaknesses? Kind of like trying to figure out very early on, “What is my purpose? Why am I here?” I think it then led to this quest of mine to connect to that and maybe be more open to less traditional career paths.

Also, being the only girl was pretty wild. I remember being very aware of gender from a very early age, 5, 6, 7, where my brothers would do something, and then I would do the same exact thing, and then we’d have different outcomes. Sometimes it was to my benefit, and sometimes it wasn’t, but I remember thinking, “Wow, why is that?” There was just a different set of messaging. That awareness I can directly relate to my career path because just kind of that question around gender has been in a lot of the things that I’ve done and certainly connects me to the mission behind the company I’ve built.

Odetta, a gig economy digital platform with a mission

Chris: I love that. Tell us about Odetta. What has the gig economy done, and how have you connected to it and done something meaningful with it over the past few years?

Katharine: Yeah. The economy is amazing. As most people know, they’ve interacted with it in their day-to-day, but it’s essentially just a digital platform that connects freelancers, contractors with their customers. I took an Uber today and had a driver, and I’ve stayed in Airbnb, and I have a host. What Odetta does, and I can share a little bit more about why we do it, but essentially, it connects a network of these data analysts and account managers with tech companies. So using the internet to facilitate those connections.

Chris: Is it through like an app? Website?

Katharine: It’s not an app. It’s just like a kind of website.

Chris: OK. All right. Very interesting. Well, what’s a typical freelance project for an Odetta freelancer?

Katharine: Yeah. We are usually sourcing and cleaning data. A common request from our clients would be, “Hey, I need a customer list.” So maybe they’re building a business, and they want to know, “I’d love to have a thousand companies look like this, that I can do sales and marketing on.” Or they maybe want a list of social media influencers or anyone that can help them grow. So we’ll build that database of those companies with all of their contact information. We also do quite a bit of what’s called data annotation. I didn’t know what this was before starting the company. But a lot of these tech companies are doing what’s called machine learning, which is a type of artificial intelligence. To build these models, they need what’s called ground truth data. That often requires a lot of humans to be tagging and labeling, and classifying data. So we do quite a bit of that for our companies.

Chris: So you do the legwork to get them started?

Katharine: Yes.

Chris: OK. That’s really cool. How do your customers find you and what kind of customers are they?

Katharine: I would say now it’s a lot of word of mouth or existing customers that maybe they change companies and then hire us. We also do B2B sales on a typical type of customer. They’re mostly tech companies kind of early, 10 to 50 people, and they’re looking for help. They may have been running these processes already in-house and they’re at a point where they’re looking to find a team that can run them more cost-effectively.

Chris: OK. I like the call out to machine learning because the most interesting thing is you start to acquire the data machine learning-wise ... What you said, the ground truth, to aggregate all of that, I think is really important. And just how invasive or how much human energy is being put into getting that machine learning started.

Katharine: Just so much.

Chris: It’s really interesting.

Katharine: It’s the future is really about there’s all of these kinds of bots and artificial intelligence, but actually a lot of people say all these jobs are going to be lost, but more jobs are actually getting created through all of the machine learning.

Chris: It’s incredible. The jobs are changing, really.

Katharine: They really are.

Chris: They’re just different jobs.

Katharine: Yeah. Yeah.

Chris: OK. Candidly, I’ve been a user of Fiverr, and I’ve been a user of Upwork. It used to be oDesk and a couple of others.

Katharine: Sure. I’ve heard of them.

Chris: Yeah. I’m sure. So how are you different? How’s your group different than those other apps?

Katharine: OK. At the highest level, we’re team-based and project-managed, and then we have a specialization in data, and then we have a mission that I’ll talk about. But if you’ve used any of those, it’s pretty similar. You go to Upwork or Fiverr, you post a project, and within seconds, it’s pretty incredible. You have hundreds of people who are bidding for that project. What you do is then you go through, and you might interview people or find the best person, best designer, whatnot. Then you’d be managing them and checking their work. The quality can be really good, you can get lucky, or it can be very inconsistent.

With Odetta, you just post a project, and then what we do is, we kind of figure out the rest. We’ll build a team, we connect you with an account manager, and then that account manager will kind of build the scope of work, build the team, run the team, manage the team, and kind of run that workflow for the client.

Chris: Oh, that’s interesting. So instead of the system and the ... Because that’s what I’m used to, it’s basically infrastructure and no oversight, with the Fiverr and ... It’s just this open marketplace.

Katharine: Hopefully, it works. It’s amazing. There are a lot of types of jobs where that’s exactly where you want to go because you have a very specific thing, and you want the best in the world, and you want them to all be competing for that job. Other things, though, there’s just a certain way that it needs to get done. Why not, also, as part of that infrastructure, have a team that is checking the quality and training the team, because it should save you time? Most of our clients, they want cost-effectiveness, but they also don’t want to be managing the team.

Chris: So work quality and oversight are a big part of what you guys are doing. But then, at the same time, the inspection and the outcome are largely better because of your capabilities.

Katharine: I think so, especially when it becomes specialized. If we’ve done something hundreds of times, over and over again, then we start to have software and tooling around it and templates. So you can kind of just go there and know that it’s going to be a certain level of quality, and you don’t have to worry about it.

Find a business concept that aligns with your values

Discovering an untapped labor market of women who want to work, but lack opportunity

Chris: OK. That’s really interesting. You mentioned the mission thing. How did you realize this opportunity, and how was the mission sort of born?

Katharine: Yeah. So I should say that I was on the hunt for a startup idea for many years. I was really on the hunt. I had been looking at a tech company and was working on a number of different ideas on the side. I wanted to build something in the female economy space. What that means is I wanted to build products and services for women that didn’t exist yet, because there was some sort of market bias or failure. I was looking for something that could be a large technology company. I happened to meet someone on the board of Upwork, and he shared with me, or really kind of pointed me in the direction of the gig economy.

I did some research, and I realized that 75% of the women getting educated in the Middle East and South Asia were not working. They were not working in the labor pool, but they weren’t also on these freelancing platforms. Right away, when I learned that stat, I was like, “Wow, there must be something wrong with work.” And that meant that hundreds of millions of women who were fluent in English, super-qualified, had just disappeared. I started thinking about that and really wondering why.

Then somewhat fortuitously, two weeks later, I was at a class reunion, catching up with a classmate of mine who grew up in Pakistan. She helped me answer that question of why. Essentially what we did was we posted on our Facebook page ... It was just a very simple message: “If you’re highly ambitious and looking for remote work, sign up here.” Within 48 hours, we had something like 300 women sign up to our little Facebook kind of sign up.

Chris: That’s amazing.

Katharine: These women were from some of the best MBA programs in Pakistan, the PhD programs. But we also had women from Turkey and Oman and Jordan. I was floored. I was like, “Gosh, there is something here.” Then my next step was I want to go meet these women in person.

Chris: OK. Yeah. It’s like a lot of your travels, right? What was the most impactful trip for you to make this discovery in Asia?

Katharine: Well, I must say that I had spent time in Asia and some time in the Middle East, but I had never been to most of the countries that I was all of a sudden looking at, which were places where women were highly educated and not working. So Pakistan was an obvious kind of next one, but in terms of going there, I still had a job, so I wanted to take a vacation and organize a visit. That’s what I did. I started getting a tourist visa and planning a trip.

Chris: OK. What happened on the first trip?

Katharine: Well, first, I had to kind of answer the question, “Was it safe for me to go?” I got really mixed reports on that. I reached out to a number of people who were either from there or who had friends who lived there or worked there. I would say this is where I was less data motivated. Most people said it was not safe or mixed. So I just ended up listening to the people who said it was safe. I found a few people who said it was completely safe to go. So I got a tourist visa. It took me three or four months to get a visa to be able to go.

Katharine: I’ll never forget I landed... It was a flight from Doha to Islamabad, and on the flight, there were a ton of foreigners. I was kind of feeling relieved because, prior to going, I had to turn my phone off because I had so many people concerned about my safety trying to intervene. Essentially, the air hostess started calling up names, and pretty quickly, all of the foreigners, non-Pakistanis, were called up, and they were escorted to these armored vehicles and sirens. Then they were off. I was left on the plane. I was by myself visiting with the tourist visa. I was like, “Wow. Oh no.” I went to the airport, and there was a line for a tourist visa, which was empty, so it was just me. My ride was an hour and a half late, arrived really late at night. So I was standing in the airport, being like, “What am I doing?”

Ultimately, I’m so glad that I listened to those people who told me that it was safe, because it was safe. Certainly, if you’re kind of traveling in the way that I was traveling. So I ended up just staying in this hotel and meeting all of the women who had applied to this Facebook post. I met hundreds of women. They were amazing. I mean, it was just like these super smart, very humble, wanting to work hard. I think the thing that struck me about every single conversation that I had with these women was they just wanted to prove to the world that they mattered and there was this intensity about it. I was like, “Oh my God. I need to help connect them to the broader market because they are suffering.”

I should say that Pakistan is the third-worst place in the world to be female. I heard their stories and was listening to just the harassment they were experiencing in the office, on the bus. They were getting fired because they were pregnant. They were not getting hired because one day they may be pregnant. They would get their doctorate degrees because education is very valued, and the in-laws would say they could not work. There was still this very significant stigma around being a working mother. It was very much get educated and then have your children and then serve the family, move in with the in-laws. I was listening to them, and obviously, we come from such different places but ...

Chris: Different cultures, for sure.

Katharine: For sure. Yeah. There was just something there. I felt like, “Wow. I want to build something to help them.”

Chris: Wow. That’s a pretty wild story. I just want to confirm you were on the plane going to Pakistan.

Katharine: Yes.

Chris: Was it when you landed that everybody was escorted off?

Katharine: Yes. All of the other non-Pakistanis... No, it was when I landed.

Chris: Why were you left?

Katharine: Well, because I was rogue. I wasn’t affiliated with like the World Bank or any of these other places that had gone in a very organized manner with their security ... Because most people go with their security protocols, but I was there just to test the waters.

Chris: Yeah. It seems serendipitous for you to be the only person to be able to get through like that.

Katharine: Yeah.

Investigating the needs of the talent pool and clients

Chris: You met hundreds of women that happened to find this Facebook group post that was basically a poll. “Hey, so if you’re interested, fill this out.” You went to go meet all of these women.

Katharine: Yes.

Chris: What was that meeting like? Are you in a big building, and there’s just hundreds of women there? Or did you have like individual interviews? Did you like host an event?

Katharine: No, I didn’t. It was kind of more casual. It was a bunch of one-on-ones. They were organized every half an hour or got something.

Chris: Got it. Got it. Did you have someone help you set it up?

Katharine: Yeah. So the same classmate who had helped me place this on her Facebook page, she happened to be in Pakistan at the time. We were sitting in the hotel lobby, and then every hour or so, a new woman would get dropped off by her family, and they would kind of run in and then tell us the story. We had a particular format where we were kind of just asking them about their lives. Then at the end, we actually had these note cards that we were keeping that was a list of the things that they were talking about that was important to them because we were kind of on a design trip.

I was trying to figure out, “What do they care about? Why does the thing that they need not exist? And what is that thing?” I had no idea. I’d never done anything like this before. Those meetings were really informative. I mean, obviously, on an emotional level, I was like, “OK, I’m going to help them.”

Chris: Invested. Yeah.

Katharine: But also, these women knew what they wanted. It was kind of pretty clear what we needed to build.

Chris: That is so, so awesome to hear how that got off the ground and started and how many conversations you were able to have. So you’re working. Where were you working at the time, and you’re taking a vacation to do this, right? What happened after?

Katharine: I was working. I was at a fintech company. I was running sales for them. I kind of just went back to my job. I was living in New York at the time. But during the trip, something changed. I realized that I would build this company. I didn’t know when or how, or what that looked like. I ended up deciding to stay around for about nine months so I could earn more money so I could have more of a runway, and I wanted to wait for my bonus. I did that, but it was a really hard time for me because I was already onto the next thing …

Chris: Yeah. You’re torn.

Katharine: and running this team. So that was a really tough time where I was like trying to do both, but I didn’t want to tell anyone that I was leaving just yet. But I decided to really just go on this adventure. I quit my job. This is nine months later. Got rid of my things, and I moved to the country of Jordan.

Chris: Oh my goodness. What made you pick Jordan?

Katharine: Which sounds kind of random. I had never really known much about the country of Jordan. It’s a beautiful country, so is Pakistan. Truth is, I had met someone who was from Jordan. I’d been connected to her while I was thinking about this idea ... It’s funny how, once you have an idea, just all of these people start to appear in your path. Maybe you’re more open to it. I had all these different kind of teachers are helpers who started appearing for me. One of them told me you should go to Jordan and I can introduce you to a lot of people there. I said, “OK. Why not?” Jordan’s interesting because 90% of the women who get educated, and more women than men get educated, they drop out right after that education. It’s a pretty safe country. I know I could kind of just walk around and ask questions. So that’s what I did. I rented an Airbnb.

Chris: Except the borders.

Katharine: Yeah. You’re kind of in the midst of ... There’s a lot going on. Yeah. Just such generous people. And I rented this Airbnb, and I was going around to the local universities and just kind of meeting people and trying to figure out ... I knew that there were really smart women, and I had an idea for maybe what we would build, but I didn’t know yet what skill set to focus on. Should we do design? Should we do computer science? And so I just was asking those questions. It was an awesome time. I learned a lot. Meanwhile, I was also trying to figure out the demand side, essentially, the clients who would pay for this. I had been working in tech, so I knew ... I had a number of friends who worked at tech startups.

I love people who work at tech startups. I think that it’s a lot of people who are ... I wanted to sell to tech startups because I thought they would be very open-minded about something like this. They need work to get done. I mean, they are moving fast. So I ended up having a number of conversations with people who worked at these startups and asked them what kind of thing or service would they be interested in outsourcing. Really, at the time, it was very clear all roads led to data. People were talking a lot about machine learning, artificial intelligence, data science. I thought, “OK, well, we’re going to build something that’s going to be in service of that industry.”

Chris: That’s so interesting because I would say ... I think that’s another thing that would be really good to talk about is agency versus marketplace. Right. Would you consider Odetta more of an agency or more of a marketplace?

Katharine: More of an agency. We’re what’s considered a managed marketplace.

Chris: OK. Because the marketplace effect is so hard to start because you have to draw talent and demand at the same time. That point of convergence is really hard to manage, and crossing the chasm into scale is a really, really hard one.

Katharine: Long slog. Yeah.

Developing a mission-driven business strategy

Chris: So you’re trying to get kind of initial demand, and you’ve got a hunch and, likely, the talent pool that you’ve assessed. So data and data management. So talk to me about that point of convergence, how you thought about this business model, and how it was born.

Katharine: Yeah. I mean, it is interesting. I read a lot about marketplaces and was a bit intimidated by just the intensity of capital that seemed to be required. I thought, “Well, let’s just try to be useful for a few groups of people.” And I thought a bit less. I was like, “OK, I’m going to not focus as much on the grand vision of what we’re going to do to change the world.” It was a little bit more, “What is a model that we can use to earn revenue and get started, and what’s the simplest way to get started?”

So for that, it was actually pretty simple. We just needed a client, and then we needed a team, and then we would manage the oversight of that. I will also say that the team, most of the women that I had met, did not want to work directly for clients. They didn’t want to be in contact with foreign people or men or anything. I knew that there was going to be a massive workforce that was going to be behind the scenes and that it had to be kind of this managed model.

Chris: OK. Talk to me about how you land your first deal and start to ... What are some of the discoveries you make on that first deal?

Katharine: Yeah. You always remember your first deal. I was still in Oman. I was still spending my days recruiting talent, talking to talent. But I had posted on my Facebook page, just kind of, “Hey. This is what I’m thinking about doing.” A classmate of mine from college reached out and said, “Hey. I work at this mental health company, and we need leads. Can you do lead generation for us?” And I was like, “A hundred percent.” My background had been in sales. So he got on the phone and explained what he needed to do. I said, “Fantastic.” I ended up calling one of the women that I had met when I was in Pakistan, and her name is Arooj. I had kept her warm this whole time, but it had been about a year since I met her. I said, “Hey. It’s go time. Are you ready?” She said, “Yeah, I’m ready.”

Chris: That is amazing.

Katharine: It was just legal contracts for both sides. And then we were off to the races. It was just like that.

Chris: That’s incredible. You’re using social media and using Facebook to get connections. How did you start to create maybe more of a flow of demand?

Katharine: Right. Yeah. I mean, that’s tough, right?

Chris: Yeah.

Katharine: It’s tough.

Chris: You’re talking to somebody who ... My passion is demand gen.

Katharine: Yeah. Demand gen.

Chris: Revenue marketing is where I cut my teeth in marketing, for sure.

Katharine: Yeah. It is hard. And I think it is the most important. The first six months, I was surprised with how much traction we got, mostly through Facebook and LinkedIn, just posting the concept. People would send us cold contracts. That was awesome. It was mostly through personal connections or social media. We got Google as one of our clients. I was going after some big names for the first six months just because I wanted to be like ...

Chris: So you’re going enterprise sales. You’re definitely trying to close deals.

Katharine: I mean, not that I thought that was the best thing for Odetta, but once you can say, “Hey, we work with Google,” then people are like, “Oh, you work with Google.”

Chris: Yeah. It’s a credibility thing.

Katharine: It is. So our second client was Google, and that was just one of the best days of my life when I got that contract.

Chris: That’s incredible.

Katharine: It was week three of the business. So from there, it was just, “OK, we work with Google,” and then it was reaching out to other people who worked at different companies. Quickly, I realized that the entire business was predicated on our ability to do this, and so I moved to San Francisco to kind of double down.

Chris: Yeah. And be in the community. Well, that’s interesting to hear, just proximity for you, right? Where you went to the other side of the world to build the talent pool. You got initial demand, and then you moved to the other side of the US to go build demand.

Katharine: Yeah. Yeah. Exactly.

Katharine: I mean, imagine me building this during the pandemic. I mean, you could have just done it without going anywhere. For me, it was very important to be authentic in the beginning and actually live where we were trying to serve. Then ultimately, I was like, “Oh yeah. OK, I actually know how to find all of these women through Facebook,” and felt like I had to be there in person and just be taking people out to coffees.

Chris: Are you still in San Francisco?

Katharine: I’m not, no. That was about a year of my life.

Chris: That was about a year? OK. Well, what happened there? Did you land more deals? Did you get a different level of traction?

Commit to a purpose, not just a business

Katharine: We did. I will say, it was the first time that I was paying rent. So I got my first apartment. I was paying rent in Oman, but I just happened to be for the first, however long, nine months. It was just kind of very inexpensive for me. Revenue looked good. Month six through nine, I was pretty impressed with what we were doing. Then I moved into my apartment in the marina, in San Francisco. Week two of moving in, we lost our biggest customer, the contract got terminated. It was 75% of our team working for this one customer.

Chris: Oh my goodness.

Katharine: And so we had 50 people at the time. Essentially, the client called up and said, “We’ve automated your workflow. Thank you for your service.” I was just like, “Oh my gosh. I’ve kind of sold all these promises to all of these women that they’re going to have this steady income.” Of course, I had to figure out how I was going to pay rent. I think I had been a little cocky that it was going so well. So months nine through 18 were really tough, cold, hard sales. I had this moment where I was just kind of like, “OK. Are you committed to this business, Katharine? Are you committed? What are you going to do?"

I think it was then that I know that I realized, “Yes.” Even if I have to move in back with my parents, if they would have me, or get another job and just delay the whole thing by five years and just be doing nights and weekends. I was like, “I’m going to build this company.” There’s certain things that you need from a cash flow perspective.

Chris: You’re bootstrapping the whole time right now?

Katharine: Whole time.

Chris: Ok.

Katharine: I signed up for every kind of gig economy job I could. I was a dog walker, all of these other things. I started doing that, and then I was like, “Wait, hold on. My background was in sales. The best use of my time is just to do sales.”

Chris: To sell.

Katharine: "I’m so sorry, Katharine. You just have to do sales.” I had to drop the ego and get comfortable with reaching out to people, even if it seemed a little bit desperate. I just had a lot of reserve around using all of my social capital, all these people that I knew and going around and asking for their help. But a friend of mine, actually, was really helpful in helping me see this. She was like, “You’re giving them an opportunity to be part of something amazing. Don’t ever forget that.” I was like, “OK. I’m giving them an opportunity to be part of something amazing.” Here we go.

So I sent thousands of emails and was just in every lobby. I remember this one meeting, I was in this kind of fancy lobby of a Silicon Valley tech company, and I’d written two, five classmates who worked there. I think two had replied. Then the three who didn’t reply, I saw one of them. He ducked his head behind the printer when he saw me. I was like, “Oh my goodness, I’m this snake peddler selling this dream. What have I done?” In sales, there are these really embarrassing stories, but then there are the amazing ones. That’s what makes it great. You just start to get good at rejection.

What I learned from that whole nine-month experience was the power of recurring revenue. I started really focusing on recurring revenue. There were two other things that were amazing from that harder time, which I realized we were super resource-constrained. With that, I think you become almost smarter, and you come up with these ... Your model gets better, in some weird way.

Because we didn’t have cash, we focused on our customers. If they didn’t like it, they wouldn’t buy more. So we were just so in tune with what they wanted, and I think we ultimately built a team that just nailed exactly what they wanted because we had to.

Chris: Yeah!

Katharine: We didn’t want them to stop working with us. Then the second thing was, and this is still month nine. So I didn’t know what kind of business I was building yet. I knew that I had a mission, but there was a chance that I could have gone the whole Silicon Valley route, which is OK, go and pettle yourself to angel investors and go get a CTO and go get this fancy Silicon Valley team. We didn’t have cash, and something inside of me just didn’t want to do any of that. I just decided, let’s just build a team that is run by the people that we’re serving.

What that meant was we weren’t going to hire anyone in Silicon Valley, in the US at all. What if we could build a team where every single role, sales, marketing, ops, dev was an Odettan, one of the women we’re trying to find in these regions where they’re being overlooked. We did that because that seemed great from a mission perspective but more from a cash flow perspective. That was really the best thing that we ever did, actually.

Chris: That’s amazing. That’s a real commitment to your vision and your mission. So I just want to unpack, just for a second. The discovery of your mission, getting it off the ground, getting initial traction, and then you have an explosion, you lose a big client. You really had a crucible moment about whether or not you were going to recommit to your mission. I didn’t hear you say, “I don’t know if I want to do the mission anymore,” it’s the business of it. You were still committed to the mission. Talk me through what are the things that are going through your mind? How did you muster the recommitment, and what did that mean to pull yourself out of that and get to a second round of traction? What were the things that were going through your mind? What were some of the challenges? What were the hard days?

Katharine: Yeah. I mean, it’s tough, right? I think the good days are easy, and then the tough days are really hard because then you just have to try harder. I don’t know. I kept returning to the mission, our purpose, and why we were doing this. Ultimately, I realized it wasn’t really about me building something fancy that I had to look at and be like, “OK, I’m proud of this.” I was like, “How can I be useful to these women?” By the way, there’s 50 of them right here, so this team needs to figure something out. They were all looking to me to figure something out. So I went to the basics, like “OK, what do I know how to do?” I was like, “I know how to write emails.”

Chris: Yes. And make phone calls.

Katharine: At a very basic level. I can make phone calls, and I can drive to a place where I see that there are people who are working. I can sit in a lobby, and then I can explain our idea. Not in any formal pitch manner, but asking people for advice and just ... I know how to do that over and over again. I know how to do that even if everyone is looking at me with this hint of embarrassment for me. I did that over and over again without getting too fancy. I wasn’t like, “All right. I’m going to go figure out all of these things that I don’t know how to do and experiment on all these new things.” I was like, “What are the basics?” Just build that list.

Double down on your mission when times get hard

Chris: I love that. I think anybody with any type of entrepreneur story, the number of punches that come along the way, that can throw you completely off balance, a lot of people will end up giving up. What do you think was the thing that was installed in you that kept you going?

Katharine: I think it’s true. I think back to even that trip to Pakistan when I had everyone telling me, logically, you shouldn’t go. I think in the beginning, you have to have already said that you’re listening to yourself. In those moments, when you’re building a business, if there’s an ounce of you, or even let’s say most of you, that’s building it for someone else, then you maybe would listen to the voices outside. But I had been so focused on, “Why am I here? What is my skill to give? What is my purpose?” And then had been set before me these things that, intuitively, I was like, “Yes. Yes. Yes.” So I had this path that made sense for me. It wasn’t just kind of a random thing that I was doing. Because of that, when an obstacle presents ... Maybe this is going back to younger years, but it was like, I kind of had an ethic of, “OK. Go around the obstacle. Keep on trying.”

Chris: Yeah. Your resourcefulness kicked in.

Katharine: Yeah. Resourcefulness kicks in, and I think... But that connection to “why.” That’s why when I hear people starting businesses, I’m really interested in their motivation. It’s not that ... it doesn’t have to be the thing that you thought you would do from birth; no one has that. I mean, some people do.

Chris: Yeah. Maybe.

Katharine: Right? It is that you’ve connected to your “why” and in a very fundamental way. Then nothing can stop you because you have a will. I also had removed some of the ego around why I was doing it. So I didn’t need things to happen in a certain way or at a certain timeline. I didn’t need a company to come in and validate me. A lot of things I didn’t need. I had a group of people that I wanted to serve. I felt like I had been given so many things, and I had so many sets of experiences that I was dying to have the opportunity to prove myself. I had wasted away so many years working at someone else’s company that this was a carnal need. Odetta was something that was deep inside. I had to build it.

Chris: Yeah. I think something that is really unclear for a lot of people. I feel like you’re pointing at how you got to an authentic understanding of your purpose. Because if you think about it, everybody knows “I need a mission.” Any company, it’s like, well, “What’s your vision, mission and your values?” Right? Three words. It’s like, well, what’s the difference between a mission and a vision? People struggle with that. But I think this real, authentic understanding of your “why” is really important because if you have a mission, there are two clear directions that you could go with a mission: a gimmick or a cause.

Katharine: Right.

Chris: I think that where people that will continue with their gimmick and it’s their hook, and it’s their shtick, and it’s not really a mission, but they say that that’s their mission. What I feel you were able to do is, you had an undeniable experience that ratified your cause, and you built a business around that. There’s not one moment you’ve been like, “I questioned my mission.”

Katharine: No.

Chris: You had really gotten the authenticity out and the ego and all the stuff that you’d been able to get out. I think that’s a really important thing for entrepreneurs, especially people who are just starting or people in that crucible moment to go, “Let me, in an authentic way, question my ‘why.’” Right? What do you think is the thing that pressure tested your “why” the most in your story?

Katharine: It’s constantly pressure tested because I think there’s so many different ways to build a business. If you listen to the outside world, they tell you that these are the steps. Then you have to just continually go back to your why. So we decided not to take funding because I was concerned about the impact of that on our mission. I wanted to build this very healthy organism of Odetta without any intervention. It was really important for me to build something that didn’t have people inside being like, “Go optimize this. We don’t care about your mission.” I know that there’s a whole kind of ecosystem of great investors who will support you in your mission. But I knew, instinctively, that I had to build a company that had no foreign intervention. There was a moment when I was looking at term sheets.

Chris: You said no to them.

Katharine: I just said no. There was a moment when we had that ...

Chris: That’s a pressure-tested moment.

Remember a mission is a movement, not a solo act

Katharine: That’s a moment. We had another moment where we had this incredible woman who went to this fancy school, and she wanted to work for our company, based in the US. Her mission was not aligned. I could just tell that she wanted to join us for other reasons other than our mission, and so we said no. I almost feel like it’s like, you have to really protect it with the people inside, and from the outside world, it’s just full of distractions. Funding was a big one.

Even more recently, we have all sorts of questions around, let’s say we earn more income. Where does that money go? Who owns the company? It’s like thinking about that alignment for a business is something that I think about all of the time. I’m not really motivated to build a business where there’s just a few people who get wealthy. Ultimately, I want to build a company where the first 300 people on our team can become millionaires ... That’s my mission. In more ways than one, I want to build a business where all of our extra income goes out and supports the communities. It’s mission-oriented.

Chris: Excuse me. Who is somebody that comes to mind when you say the word “one of the first 300 to become a millionaire.” Who is somebody that comes to mind? What do you think it means for them? What does that do to you inside?

Katharine: Yeah. I mean, amazing. It’s like I could die happy. That is what I want. I see all of their faces right now, and I feel emotional. They trusted me. I went into this very foreign country where I knew no one. Who knows who I was. I could have been in the CIA. I could have been anyone. The truth of it is that we got hundreds of women from all over the world, to just make a promise to each other. Yeah. Many of them are just working so hard.

Katharine: We’re still bootstrapped. So there’s a lot that I can’t yet do for them. We want to pay more. We want to have all sorts of services for them to completely lead these extraordinary lives. Not just for them, I also want to build a forever company. We are thinking about, “OK, what do we need to get to the next level?” But when I see all of their faces, many of them have just been with us since the beginning. I will be so happy when one day they all become very wealthy, in many different ways.

Chris: Yeah. What would be something that you think would be ... I think one of the things I’m trying to get to with you is your measurement of success. How could you describe, “We are successful when ...” What is an event that would happen, or an impact that would’ve occurred, that you’re like, “I did phase one.” Not that success means the end, but what is like, “I did it"?

Katharine: It’s so interesting. When I first started the company, I had these weird metrics that I set for myself. Weird in the sense that they just seemed so arbitrary. I was like, I want to build a platform for 1 million women, so we can have 1 million work women working simultaneously. That was kind of absurd. I realized, “Why 1 million? What about a 100,000? What about 10,000?” Then, ultimately, I was like, “I will feel successful if I build a company for 1,000 women and if they’re all happy and we’re transforming their lives.” The greedier part of me would like that to be more like 10,000 and then have that ... I’ll feel really good about that number. Yeah. It’s an arbitrary number, but the 10,000 number is one that I know that we can get to by ourselves. In other words, this independent company it’s just me and the Odettans, and we’re going to build this business without any foreign intervention. I think we can get to that number.

Create structure for your mission to evolve and build a legacy

Chris: What three big things do you feel you need to make it a forever company? And not a company that just gets acquired. Because your mission goes away in a big way.

Katharine: Yeah. What is that? I haven’t figured that out yet. What’s the structure of a business that can live forever and continue its values. What does that look like? Who owns it? Who’s running it? So it’s like a corporate governance structure. Thinking about some of the family businesses that are really amazing that have been around, and how do you kind of build that forever? Probably number two is a real career trajectory. In our model now, we have built out a place that’s great for, let’s say, five years of work, but how do we build a business ... Our Odettans, that’s what we call them, Odettans. They’re asking us, “Katharine, can you please build this so I can work here forever and so that my daughter can work here one day.”

Chris: Wow.

Katharine: They’re asking that from us. So we need to figure that out. That’s number two. “OK, what does a business look like where it’s the opposite direction that the world is going, where you only go someplace for one year, but where you can have all of those phase levels of learning?” Then probably three is the learning machine. So it’s continuing the culture of learning such that in 50 years, we will not be doing what we do today. I mean, I think even in 10 years. We are in between human and the machine, so we’re the bridge. So we’re going to be continually iterating. How do you kind of instill that in the culture of the business?

Chris: When do you sort of make a discovery on a new capability? You’re doing the machine learning. You’re doing a lot of data-centric stuff. What is a new capability that you got to go drive demand for and then also have to have the talent pool for? What’s kind of the next big one for you guys.

Katharine: We typically just listen to our customers on that. So they meet our team, and they’re like, “This is great. OK. Build me this.” In that way, our customers are building the future of artificial intelligence. So they’re kind of like telling us where to go. I would say that we’re more of a listening machine. I think the world of data science and machine learning is very interesting. It still does require a lot of human intervention, but we would like to be that business that is able to handhold these companies, smaller businesses that don’t have the resources that these big tech firms do, to be able to do some of these smarter tooling around data. That’s probably the direction, is just a little bit up stack.

Chris: Well, what is something that you’re like, “We have to avoid this?” Or what is something that you feel is a future risk that you want to design a way to avoid in the future?

Katharine: Like in terms of types of work?

Chris: Yeah. Just for the trajectory of the business or, it could be types of work. What is the risk out there that would keep you from getting to the next step?

Katharine: Yeah. We are that bridge right between humans and artificial intelligence. If we don’t move fast enough, we get automated. That happens all the time with our workflows, so that’s a big risk; which is how do you stay ahead of that? I think a lot of the ways we do that is through software. So we’re learning software, and so something gets automated, but then we’re running the process to build the next kind of human project.

Chris: OK.

Katharine: So that’s what we’re doing to prevent against that.

Chris: Yeah. One of the ways that your workflows get automated is if you share your workflows that you’ve designed, right? Do you do any intellectual property protection or things like that? Algorithms are patentable. I have a patent on an algorithm. OK? So I know that those are patentable, and it’s largely a process. It’s the way data matriculates through a process, right? It’s a sequence of events. So are you doing anything to protect the intellectual property you and your team create?

Katharine: We have some. Yeah. It is, I think, maybe doing more of that. A lot of times, our clients are building kind of the IP, and then we’re the team that is supporting. But in the vision, in the future, it would be that we have a set of building blocks and patentable technology that then we’re sharing with other customers that don’t have the resources to build that.

Chris: Yeah. That’s interesting. That’s interesting. What’s next for you guys?

Katharine: Yeah. I try to think about what do we want this year? Then we have a more existential, longer-term question, “What does Odetta look like?” How do I imagine it, where it’s not so reliant on me or my role, and then it’s just a machine that runs. This year, we’re trying to get to 500 people, so 500 Odettans. That will then get us, maybe next year, closer to our a thousand goal. We hire 25 to 50 new people every month. We’re doing a lot on the hiring. On that front, there’s a lot of boot camps that we are building that we can build to get people ready to work faster.

One of the things that is most exciting, to me, is ... So we have a 10,000 person waiting list for our company. That’s both amazing and really sad. I think that a lot of the people that are waiting for work is just a few simple tweaks where they would be able to participate in the market if either they had that training or they had that just that first experience or that first person who took a chance on them. How do we build that for them? We have our vetted work platform, but then what are the learning organisms that can then help these women get ready and get connected?

Chris: So you have 300, you’re going to 500 and you’ve got a waiting list of another 10,000. These are all similar skill sets, yes? Or it’s maybe varying degrees of the skill because that’s what you were saying is that we don’t know how great some of these people are, but largely, there’s probably a low to very high capability of skills in the realm of what you’re looking for. So I think what, one of the things you’re saying is you need the demand to show up?

Katharine: Yeah.

Chris: Right? So what are you doing on that side to go drive demand for getting to your thousand and then being able to ...

Katharine: We need more clients. I mean, we’ve been really focused on particular types of clients. Some of our clients have been amazing. They have teams of kind of 50 to 75 people that are working for them. So that type of client is really great for us, because it provides very consistent work for our Odettans. We do sales. It’s just a B2B machine. I think we probably need to do a lot more in marketing to tell our story so more people could use us. I mean, the truth is that outsourcing pre-pandemic was being used, Ii wasn’t necessarily mainstream as much as it is now. But that was one of the big shifts in the pandemic that most small businesses, every tech startup, is outsourcing. They’re really trying to figure out who are their partners and how do they do this. It’s being done. So we really kind of accelerated a lot with the pandemic. I think there’s a lot more we can do in terms of just sharing our story with companies, and what we’re good at, specifically, so they know how to leverage us.

Chris: I think one of the things that has been really awesome about your story is your level of commitment is so high. Your level of compassion and care is so high. Your vision and your mission are super clear. I definitely want to know what we can do to help because it’s a pretty compelling story that I hope you have a lot of runway to tell. So super good.

That is amazing. I have rapid-fire questions for you now.

Rapid fire questions and closing

Katharine: OK.

Chris: Aside from the people in the Middle East and South Asia, what’s your favorite part about visiting that part of the world?

Katharine: Gosh. Probably the most striking are the sounds. Just being there, getting off the plane. For me, the most extraordinary thing is just listening to the calls to prayer. So in Jordan and Pakistan, five times a day, there’s this kind of sound that goes off that reminds people to kind of stop their worldly matters and go inside and pray. It’s this beautiful sound. Yeah. That was my favorite part, actually.

Chris: Well, do you still go to Pakistan?

Katharine: I am going at the end of this year. We have a lot of people to meet in person who I haven’t met.

Chris: So you haven’t been back since that first trip? That’s incredible. Wow. You used to live in San Francisco. Which do you enjoy the most between San Francisco or NYC, and why?

Katharine: Oh wow. Oh wow. I feel like I’ll make enemies here. I love New York. I’m a New Yorker.

Chris: Compelled to say that.

Katharine: Yeah. I love New York. I love the energy. Yes. New York is just the energy of the people, and you can just walk out for a break and walk anywhere. It doesn’t matter. And just this endless discovery. And why. You know what? I will say, though, San Francisco, I’m very into nature and camping outside. I had these amazing weekend trips where I would take my car and go to Big Sur. I don’t think you’re allowed to do this, but I would drive to Big Sur, and then they have these overlooks, and I would wait until the cops were gone, and I would park there and then sleep there. I’ve done that so many times, and it’s amazing to wake up on the cliffs of Big Sur.

Chris: Oh my goodness.

Katharine: So amazing.

Chris: Well, give a shout-out to your brothers. What are their names? What’s one word that they’d use to describe you?

Katharine: Oh, gosh. OK. It’s kind of like “Good Will Hunting,” but my brothers are James, and then ... I’ll do an order of birth, which is really important in our family. James, and then Andrew, within the quads now. Andrew was two minutes older than me. It was Andrew, then myself, and then Jeffrey, then John. They’d probably say some mixture of super independent or determined and adventurous. Because I was always going some far, fun location.

Chris: Yeah. Yeah. Are they travelers?

Katharine: Yeah. We’re kind of all travelers, but I ...

Chris: Do you travel in a wolf pack?

Katharine: No.

Chris: I’m just kidding.

Katharine: We don’t like to.

Chris: I had to say it.

Katharine: Yeah. I know. I mean, it’s funny, when I was in my twenties, I moved to Southeast Asia, and I had a brother who was living in, he was living in Hong Kong and then Tokyo.

Chris: Unbelievable.

Katharine: Yeah. Then my other brother lives in Singapore, and I have one in Berlin. So we kind of quest for being unique, coming back to that. Everyone got their location and learned their language. I own France because I speak French. It’s like we all have our different locations where we live, but we don’t ever live in the same location.

Chris: Totally understand. All right. Well, if you could place a billboard on a street that only little girls rode by and could see, what would you have on there and why?

Katharine: Yeah. That’s easy. I would have, “Your dreams are valid!” Be really kind of like a big, big sign. I think the message is not to lose yourself. Even if you’re in an environment where your dream seems outsized, or you don’t know anyone else who has that same dream, that it is valid and it is yours for the taking.

Chris: Oh, OK. That’s amazing. That’s amazing. Well, enjoy that. It was great to have you Katharine.

Katharine: Thank you for having me.

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