Today is a special day for Odetta. Back in 2018, Katharine Wolf, our Founder and CEO, came across startling statistics about low female participation in the workforce of the MESA region. She saw an opportunity here. Opportunity to empower, build and realize the dreams of females across the region. She boarded a flight from New York to Jordan to search for possibilities and eventually founded Odetta on May 24, 2018.

Four years later, we have surpassed many challenges and achieved numerous milestones. So we decided to sit down for an in-depth conversation with Katharine on leading Odetta to its fourth birthday. We hope this can help spark ideas and inspiration for other companies and entrepreneurs.

1. How does it feel to see Odetta grow and celebrate its fourth birthday? Are you nervous or excited, and did you manifest this in the initial days of Odetta when you started off? 

I feel grateful and grounded on our fourth birthday. Odetta is the most authentic thing I've ever done, and it demonstrates to me that when you connect with your purpose, the universe does indeed conspire to make it come to life. For many years Odetta was a question: could we build a company like this that helped women do that? At the end of our 2nd full calendar year, we were solidly past survival mode, and now on our fourth birthday, I am more excited than nervous. I believe that we manifested Odetta in the best possible definition of that word. 

2. How did you figure out what roles to fill in the early days? What traits are necessary to become an Odettian and any advice for entrepreneurs on the kind of people to hire? 

I did a good job picking people who would be loyal. It is a long journey to build a company, especially bootstrapped, and so loyalty to the idea and to the team turned out to be much of our magic ingredient. Part of this was that we built a company that was needed but did not exist. We actually solved a need for our freelancers, and so they rewarded us with their dedication, gifts, and time. I love this story as so many of the women we hired had been overlooked by traditional employers, and we just proved so much to the world by turning them into our greatest strength. We look for Odettians who are dedicated to their work, kind in the way, they treat people, and humble in their approach to the world. It is wonderful to be surrounded by believers, especially in the early days.

3. You’ve mentioned on numerous occasions that sales are one of the toughest parts of leading a startup. Do business school and a prestigious MBA help with that? How did Odetta get its first client? 

Most MBA programs never teach sales and that is something that must change. I think the best sales training is to help a non-profit, or political organization fundraise or sell. For free, you will learn how to do sales. I am referring to the people in the streets or on the phone who ask for money for a cause; it's terrible soul-wrenching work yet is the best training for starting a company. Rejection therapy makes you able to ask for what you want. I try to ask for discounts and for extra random requests in my everyday retail experiences as I know these enhance my ability to ask for the important stuff when it matters most.

Our first real break was when my friend from college Justin hired our team to do lead generation. Our second client was Google!

4. Odetta has been bootstrapped. When did you decide to bootstrap Odetta? Did you ever think of raising capital or taking out a bank loan? Any advice for entrepreneurs seeking investment?

It was month 9 when I was considering taking venture capital. I was about to do term sheets and decided against it. Maybe it was fear or intuition, but I just did not feel like it made sense for Odetta. It is one of the best decisions we ever made.

If you can keep your company, especially in the early days when fundraising is distracting and the costs are exorbitant, then I think you will at least gain positioning power for later. If you can build a revenue-generating business that funds your company instead of taking on capital, then I would say this is ideal. 

5. Starting a company from scratch is hard work. Infinite sleepless nights and always being on your toes to grab any opportunity that comes your way! How do you stay productive with such a hectic and sometimes unpredictable schedule?

I think it's true that you must have an opportunity-seizing attitude when you start. I equate it to being endlessly hungry…it’s an intensity of “willing” something into existence even when logic says, “it is not possible.”

While I have prioritized Odetta above many things in my life, I do make sure that I have balance so that I am not burning myself out. I have always slept well, as for me sleep is what has allowed me to build this smartly. I used to do all-nighters early in my career, and I no longer find them productive. 

6. What is the right way to approach a failure? And how about success?

It is important to breathe and pause. I have found that both failure and success are part of company building, so I do not get too attached to either. For instance, we lost our largest customer in month 9 of building Odetta and life was stressful. I used that challenge to invest in building a sales machine and it turned out that this challenging time made us a more customer-focused company. 

It is important to celebrate the people and moments along the way. Life is short and it is all about the journey. Your destination always changes if you are listening.

7. How many times (if any) have you thought it was all over and all your efforts went in vain before something changed your viewpoint, with an answer, an intervention, or a new idea? 

Months 9 through 18 of building Odetta were challenging. I say that I left San Francisco because I did not like the city, but the harder truth of it was that I could no longer afford rent.  I was not able to pay myself anything from the business until the end of year three and a half, and so I was and still have massive credit card debt. These are the realities of personal liabilities but they do not speak to the more nuanced truth, which is I believe in the future of Odetta being rosy, and am completely comfortable today being stretched financially to make that happen. 

8. Sometimes we are so focused on the everyday tasks that we subconsciously begin to live in a bubble. We tend to lose sight of the big picture and get lost in cumbersome details. How do you make sure to look at every scenario from various perspectives while being ruthlessly objective at the same time?

I journal every day and this helps me process things that are hard to understand and keep track of our insights. I have to constantly remind myself of what we have accomplished and why we are here, as the world can be distracting and I can forget what I have learned. 

I take a lot of weekends to remove myself from the business, and I often return with fresh ideas. I took a month last year away from the business while I was in Costa Rica, and this was one of the best things I did for myself as a founder. 

9. How tough is it to ‘stop’ working and take a break when you’re leading a startup? You have taken breaks twice during the journey of Odetta till now. Your team managed everything during the time. How important is it to trust your team and any secrets to such a trustworthy and reliable team?

When you have great people, it is not too hard to take breaks. It requires the ability to delegate and trust people, and both for some reason are easy for me. I think our mission attracts great people. I believe that our asynchronous model instills trust in people. I know that our belief in people is the magic behind everything we do.

10. How to approach the mistakes made by your team? As humans, we can become frustrated and anxious, but one should not inflict negative emotions on others. How do you guard your team against the negative/gloomy emotions that you are feeling at a specific moment? Or do you prefer to be transparent and share it all, ultimately seeking advice from the team?

This is one of the greatest continuing lessons for me. It is so important to place yourself in the shoes of someone else, and also not to react to triggers at the moment. My regrets within Odetta are any time I have not followed these rules. When I am distressed, sometimes I have this naggy voice that is trying to teach a lesson while I process our failure. Usually, the failure resulted because of something I never communicated. My work is the everyday love I invest into the business, and I hope I will be remembered as someone who is approachable and focused on being a better human. 

I do believe in sharing direct feedback constantly so that our teams can learn. My intentions are to build someone up and not break them down. 

11. Constantly motivating yourself and trying your best at anything & everything can be tiring. Do you ever think of finding a co-founder or not finding one proved to be a blessing in disguise? Who is your go-to person/mentor when seeking advice? 

Without a cofounder, you can move faster and you can build something straight from the heart. Both of these were very important to me, and so I am grateful I decided to do it alone. 

I have chatted with nearly four hundred Stanford GSB founders along the way, and these founders have been my greatest source of advice and support.

12. How important is networking when leading an early-stage startup and how do you approach the concept of networking? Any advice for our readers on networking with the right people?

It's great to ask for advice and build a machine around the process of asking for advice. These people will help you on the call, but also later by building an ever-increasing network of helpers. I think one thing most people fail to do is to invest in their network with follow-through. I do this by setting recurring calls with people who are most critical to our health, and I also write a monthly newsletter from the heart for nearly four thousand people who have supported us along our journey. 

13. There are Odettians who have built startups with fellow Odettians. How does it feel that you have motivated, inspired, and provided a network for people to connect and work together on things they believe are important?

This makes me so happy!

14. How encouraging or demotivating is the (presence or lack of) media spotlight? And did ranking higher in Forbes twice (America’s Best Startup Employer 2021 & 2022) change people’s perspective of Odetta or presented you with more opportunities for scaling and potential investments? 

I like to say that “no news is good news”...I think many founders place the cart before the horse when it comes to press. Do something notable and then drum your chest, or better yet, let your customers do that for you. I know this first hand as I made the mistake of over-reliance on self-promotion in my second company I was building a company for patients to get access to organ transplants, and we were all about the press and marketing. We had no product and nothing of value to offer, and yet all I wanted was awareness. I feel so much shame around how I acted as that leader, and have used that to change my approach to the media for Odetta. It was a hard lesson well-learned.

I am skeptical of business rankings in general, but for Odetta to rank at all shows that company culture and identity can be built remotely while still being organic.

15. How do you manage to keep sane, stay contented in your personal life, and grow a startup simultaneously? Do you practice any hobbies?

While my career is Odetta, my vocation is writing, and my hobbies are reading, camping and travel. These are mostly solitary creative pursuits, and so I balance this with spending time with a network of friends. 

16. Let’s talk happiness. People often think that once they reach a certain goal (like getting admitted to a top university or being hired by a great company) they would feel happy. But you mentioned in Odetta’s newsletter (Feb 2022) that if the journey does not make you happy, the destination won’t either. How important is it to enjoy the journey and how to do that?

I think a good way of saying this is that if you are unable to be in the present and enjoy what you are doing, you may not be happy later, at least until you learn that lesson. I think it is important to have goals, and I love being ambitious and driven, but without being able to sit still, I do think you may end up with regrets about how fast it all went. 

One way to enjoy the journey more is to make lists of what you are grateful for and to send love to the people you are on the journey with. I think writing about the journey for me is rather healing and helps me live it more in my daily life. Probably an important hurdle is to become aware of and slowly empathize with your critical voice; I am referring to the small voice that causes so much unhappiness. I have found that this voice often demands too much of me, and if I can calm that voice (instead of listening to it), I can enjoy so much more of what is amazing and startling in my everyday life. 

17. Intuition vs Facts? How to know which one to follow and when?

I usually distinguish between being data-driven and intuition-led. I would say I am guided by my intuition. While I love data and surveys to gain insights about the business, the most important part of what we do is human.

18. Are you a spiritual person? If yes, how does it affect the way you deal with everyday matters?

I consider myself spiritual. I have built a much stronger spiritual practice while I have been building Odetta. Most of my spirituality consists of journaling, being one with nature, breathwork, meditation, and the moments I have in religious ceremonies. I was raised Catholic, and more recently, I have spent time in Church, being inspired by the autobiographies of Trappist Monk Tomas Merton and Catholic Social Activist Dorothy Day. That said, I probably derive most guidance from Buddhist religious texts and teachers. Religion for me is a way to go inside and connect with the source. 

My spiritual practice has helped me connect with my intuition in a fundamental way, and align my values with my everyday activities. It has become clear to me that we all have a purpose that is lodged deep within us, and I think our life journey is to find that purpose and express it. Doing the inner work is what helps you along most. For me, I can connect most deeply when I am still. That said, when I go on new adventures or move to new places, I feel an aliveness that helps me connect deep inside. One thing that has helped me in the last year is connecting to my breath. I can go inside, identify the area of stress, release it, and find my balance. 

19. Odetta has a horizontal organizational structure. How important is that in defining the culture at Odetta? Is the world a better place without a Board of Directors or Executive Management layer intervening every step of the way?

I certainly like to think so. I try to lead by empowering others with trust. I try to pick leaders who are humble and who naturally do the same thing, and in doing so we can flip the traditional hierarchies. People who are new at Odetta often ask for hierarchical maps, and many will notice that we have never provided one. 

20. What pressures do you feel every day as a startup founder (more specifically a female founder)? And how do you deal with them?

I used to feel a lot of pressure around what I did not do as a founder. I felt that since I did not have a CTO or build a product I was not a real tech founder. I thought that since we did not raise money, we were not an ambitious company and maybe only a side project. These ways of speaking to myself were actually messages I had received from society, and my world changed when I tagged them as such and moved on with my own view of the world. 

I think that, female founders have a lot to give the world, especially when they embrace some traditionally female traits such as empathy, kindness, and listening. I say traditionally in that this is what the world tried to teach us as little girls. 

I think the world would be a better place with more leaders embodying these traits of leadership. I also stay away from the rooms where female founders are not valued.

21. You often emphasize the importance of values like empathy, kindness, and slowing down to speed up in Odetta’s newsletters and your social media posts. These are considered feminine values and are not practiced much in the corporate world. Do you think gender plays an important role in the way you lead and make decisions?

I was born as the only girl in a set of quadruplets. I had three brothers in my set of quads and one older brother. I learned very early on that our gender dictated the outcomes, and this was sometimes to my benefit, and sometimes to my disadvantage. I would mimic my brothers and get very different results, and so I learned that society has different operating manuals for us based on our gender and what we look like. Little girls are taught many things, but politeness and self-sacrifice are top of the list. We learn to be intuitive and must be cooperative in order to succeed. I have naturally embraced many traditionally female traits and I do think the world benefits from this type of leadership.

22. The most significant turning point or ‘Aha’ moment in Odetta’s journey till now?

The day we realized that the magic of what we do is in the way we do work, not the type of work we do. This eased so much pressure on me around use cases. 

23. You regularly publish the important lessons picked up as an entrepreneur as part of the ‘Founder Lessons Learned’ series on Odetta’s website. Could you point out the most important one?

My most important founder lesson learned is that what we dislike in others is what we dislike in ourselves. This has been my most important insight. What it has helped me do is a shift from a victim mentality where I blamed others for what they did to me, to seeing everyone as a helper and seeking to change myself. In the end, the only person you can direct is yourself.

24. How has Odetta changed in 4 years and are you a different person now?

I live in much greater alignment with my values than I ever did before. I believe that I am more grounded and down to earth than I was when I was seeking to find myself and my purpose. I like to think of myself as more grateful too. I am so appreciative of my last startup job, as I made so many mistakes there, especially in how I motivated people, how I ran sales, and how I let people go. I believe that the important things went smoother this time around. 

25. Your plans for the next year of Odetta?

My plans are to truly invest in the happiness of Odettians, grow the team with virtual boot camps, and continue finding clients that can deliver recurring meaningful work. 

Today, Odetta empowers hundreds of women to realize their dreams of financial independence and well-balanced professional life. Wolf envisions Odetta as a top source of technical talent globally while allowing women to work around their schedules and interests. We are thrilled to experience what the future holds for Odetta. 

Our team is growing fast! To view our current positions, click below.