Empowered by Support: Communities, Connections & Careers – Part 3
Part 1 – Introductions and impact of communities in career
Part 2 – Initiatives and communities for women

We continue with Kathleen’s journey in a startup. Kathleen, please tell us more about OwnTrail, which you were a member of before you joined the team. Now, you’re the VP. So, how did that journey play out?
Kathleen: I didn’t find a space in social media that felt very comfortable, primarily because of the inauthenticity of how people presented themselves or how you felt you had to present yourself. So I had been following OwnTrail because I knew one of the co-founders, Rebekah Bastian, who has been a speaker in this series. Also, the previous VP of engineering was my former business partner. So, I knew the company and followed what they were doing. I joined the community early on, and the community there is very authentic. The way people share their experiences is genuine. Own Trail – the trail part- is a visual representation of your journey through life. It encompasses your work and personal life; you can share as much as you want, and the trail has milestones. One of the features we built after I joined the company is called Help beacons. You can add this beacon on a milestone on your Trail where you’re looking for support, and the community can come and help you. Sometimes this is a career pivot: people may be looking to get into a data science field who previously have been traditional software engineers. Sometimes it’s: “I’m setting up a home recording studio, and I need help doing this”. The array of things that people ask for help is quite broad. The community we’ve built so far has just been so great. It doesn’t have the negativity that I felt around other social media sites where they did not bring any joy to my life. So, I have since left them. I’m sure many of us can relate that many social media sites do not spark joy.
Are there any requirements for joining the OwnTrail community?
Kathleen: No, not at all. We did start out as a woman-focused site. So, you will find that many of our members are women, but we are open to all genders and all stages of careers and students. Most of our members are mid-career adults looking to make a career pivot or work on their next milestone, but we’re open to anyone. It is free to create an account. The trail Creator is in our free tier, as also the Help beacons and conversations. We have a paid membership option for making more direct connections and private messaging. But anyone can join.
OwnTrail is a woman-led startup, and we all know a woman-led startup is a challenging adventure to embark on. So how has the journey been so far?
Kathleen: Recently, there was a report that less than two percent of all VC funds in 2022 went to women-led startups, which was down from 2021. Our co-founders, Rebekah (Bastian) and Kt (McBratney) started OwnTrail in February 2020. We immediately went into the pandemic, which made it an interesting time to try to get funding for a startup. Still, we have raised $1.5 million. Rebecca started another Community called Authentech, which she found as she was trying to raise funds from VCs that OwnTrail didn’t fit into – like Fintech or Healthcare. So, she created this community called Authentech which is more value-driven human-centred technology. OwnTrail is currently in the Tech Stars Anywhere Accelerator, which goes through April. That’s exciting, and we got some more funding through that. We’re currently a team of eight employees and hope to grow the engineering team and the rest of the team. So, we’re doing good and excited to grow more.
Nidhi, what are some of your plans to move SheTO forward and make it more financially self-sufficient?
Nidhi: If you think being a woman founder makes it hard to raise funds, try raising funds for a non-profit. That’s a thousand times harder. One of my goals this year is to make SheTO a self-sustaining organization and begin by establishing partnerships with corporations. Salesforce is actually one of our early partners. So I’m super excited about that. This economy obviously is not the best for these conversations. Still, I never thought I would be a founder, but here I am. I didn’t think I could raise money, but here I am. So, this year’s goal is to raise funds to sustain and invest more in the growth of SheTO. Our approach this year is to monetize some of our programs, e.g. accelerators and workshops, without taking away the significant value we provide for our community members.
These are challenging economic times. We hear about layoffs, and maybe tech is no longer the blue-eyed child of the job industry. People are nervous. Rose, what is your advice in this situation?
Rose: Many tech companies are going through a reduction in their workforce and trying to reduce operating costs. Still, this is also an opportunity. Such situations allow me to be more creative and see where to make more impact. So, I consider it as an opportunity rather than something really scary. With COVID, we have seen that areas such as healthcare and education need the help of technical professionals. There are many problems and issues in smaller communities. In hospitals, nurses and doctors are trying to be ahead of the game this time around because it’s not as if the next pandemic will not happen. It’s just a matter of when. We saw an entire education system go virtual, from grade school K-12 to colleges and universities, which they were not technically prepared for. So there’s so much need for experienced professionals to help solve problems. The US federal government and even state and municipality governments need to digitize. I have been part of this kind of collaboration with civic tech organizations here in DC. Still, all across the country, tech skills are needed.
We need to understand many different industries go through these [changes] every so often. Everybody’s revamping, and they’re thinking about what’s the next innovation. As a co-founder, it helps me focus on how to make an impact in this world and leave it a better place.
When I retire, I expect things to be very digital so that I can access everything from my watch, phone and wherever. So, we’re not there yet, so this is an opportunity. I always tell people that when you see a lot of downsizing, there’s also an opportunity to start your own thing. Now is the time if you have an invention or something you’re working on. There’s a lot of money right now, particularly from the federal government and the investors looking for the next big thing. So, we can put our heads together and develop some amazing solutions right in our backyard.
My final and favorite question. What career advice would you give to your younger self today?
Rose: I would let myself know that just lead with life. You’re going to have opportunities. You want to plan, but sometimes the plan doesn’t always go in your favor. You get discombobulated sometimes. But, my life events have led me to incredible opportunities. I’ve had such a fantastic time in tech, and it pushes and energizes me even further. So, lead with life.
Farah: It’s been such a fun career. There’s so much that you can do in Tech. I would tell my younger self we can do much more together than alone, so don’t be afraid to seek help. Let people know you’re struggling, need support, or want to understand something new – find communities. It doesn’t always have to be in the workplace; it can be things you enjoy, leading to other opportunities. The more people you know, the more you will feel at ease. Everybody’s similar, and everybody struggles at times. So, that perspective really helps.
It’s a difficult time for many people, and I want to offer the same encouragement and support. It feels like doom and gloom, and everything’s falling apart, but just take perspective. It’s a global macroeconomic trend, affecting not only tech but many other areas. Natural disasters are happening in countries. Other countries have all kinds of political upheaval. People from tech are probably in the best position. They have excellent employability skills. They should be snatched up really quickly. Compared to some of these other things [happening in the world], that perspective really helps.
Nidhi: So, plus one to what Farah said, I’ll keep it short. Two things. One – find your tribe and use it. Often we get motivated to find a tribe but never use it. So, in a community, you will get back as much as you give. Two- just be kind to yourself. We’re too hard on ourselves. We want to be perfect, the ideal workers. But it’s not our fault because we got laid off. This, too, shall pass, and you will thrive coming out of this recession.
Kathleen: I am in an interesting position now, watching my daughter, who is almost 20, and in electrical and computer engineering. So, she’s following a similar path, and I watch how she’s doing things. When I think about how I do things and what she does that I didn’t do in university, I see she has found her tribe. She is not just joining communities but getting into leadership positions in those communities, which would be advice I would give myself. Especially in my early career, I just fell into leadership roles or leading projects. I would encourage myself to seek it out more actively as a student and in my early career. So, it’s really a great experience watching her. She’s doing a great job.
Thank you so much, Kathleen, Nidhi, Farah and Rose, for spending time with us.