The Crunchbase “Female Founder Series,” is a series of stories, Q&As, and thought-leadership pieces from glass-ceiling-smashers who overcame the odds and are now leading successful companies.
Bilyana Apostolova Freye, Co-Founder & CEO of Orbiit, is helping communities realize their full potential through connection.
After working in a variety of roles including organized crime investigation, international finance, and technology, Bilyana set out to continue her philosophy of lifelong learning by expanding it to others. Evolved from the first job-shadowing marketplace, her company, Orbitt, is now a virtual networking platform that works with leading VCs, professional groups, and companies to scale knowledge-sharing through regular, curated, and guided one-on-one conversations.
We asked Bilyana about her journey navigating the fundraising, hiring, and scaling necessary behind the scenes—including recruiting its first early adopters to now servicing prominent industry leaders.
Q: Tell us the story behind your company’s founding. What led you to start this business?
A: My co-founder Luuk Derksen and I have always been proponents of lifelong learning. We believe the best way to keep up with our fast-moving world is through continuously exchanging best practises with other operators. Orbiit is an evolution from founding and running the world’s first job-shadowing marketplace for two and a half years, where we saw firsthand how shadowing unlocked unprecedented learning opportunities. When the pandemic struck and in-person experiences came to a standstill, we took a hard look at the options for our job-shadowing marketplace. Do we wait it out? Do we pivot? Do we give up? (These options were all too real while I was down with COVID-19 and five months pregnant in March). But how could we wait or fold when people needed more connection and support than ever? We quickly repurposed our tech, translated our insights of how to engineer the perfect connection into a virtual setting and re-launched with an even bigger mission — to enhance the potential not just of our own community, but every community out there.
Q: What problem does your company solve, or aim to? When it comes to that issue, what are some of the most meaningful impacts your company has had to date?
A: As community managers, we experienced first-hand the challenges of bringing people together in a meaningful way—from matching, to scheduling, to gathering feedback. Many communities take pride in the strength of their network but don’t focus enough on how activated it is. Like everyone else with a busy job, community managers struggle with limited bandwidth. They don’t have a systematic, data-driven process for keeping track of and connecting individuals who might benefit from networking with each other.
Orbiit provides a systematic approach to community activation. While we’ve created a seamless experience for the end-user. We built our platform with the community manager in mind. Once they set meeting parameters like topics or frequency of interaction, Orbiit handles all communications, scheduling, feedback collection, and analytics.
Since pivoting, we’ve been helping professional networking groups and leading venture capital firms looking to increase knowledge-sharing across their talent/members. We’ve connected leaders from companies like Notion, Airtable, Uber, Superhuman, and Warby Parker, many of whom are spread geographically and sector-wise, thus unlikely to connect organically.
Q: In what ways do you think differently about your industry than others do? In what ways are you disrupting your industry?
A: We believe that each conversation has the potential to be life-changing. But we also know that time is our most precious commodity and we don’t like leaving things to chance. Orbiit is not a conversation roulette program or a networking platform where you have to speak to 20 people to find one good conversation partner. Our approach has been shaped by the conviction that one bad match is one too many.
There are three aspects that ensure high ROI on each Orbiit connection—a robust matching criteria of participants (e.g. on years of experience, role, company stage, etc.), a relevant topic that both participants opted into to (complete with a suggested agenda), and overlapping availability, ensuring high completion rate of scheduled chats.
Our process and technology focus on curation at scale, and we use AI not to remove the humans from the equation but to put them at the forefront.
Q: At what point in your business did you decide to fundraise? Why was this the right time and right approach for your company?
Luuk and I were adamant that we wouldn’t be raising on just a big, unproven idea. We decided to fundraise after about a year of bootstrapping and “doing the things that don’t scale” (reference: Paul Graham). We did almost everything ourselves—hacking the product together, recruiting our first customers and overservicing them, generating PR, and learning the risks and opportunities of the market inside out. We wanted to go to investors with traction and plenty of proof that our early adopters love the platform. Only when we had all that and put the whole narrative together did we raise a friends and family round, get into a SaaS accelerator, Acceleprise, come out of the program, and get our first VC check from Founders Fund.
Q: What was the best piece of fundraising advice you got?
That it’s not just about taking any money, which is counterintuitive when fundraising can be intimidating and only 2.2% of the $130 billion global venture capital invested goes to female founders. However, building a startup is difficult as it is, so not having investors with relevant experience and contacts you can rely on, or worse, not fully trust because your incentives are not aligned, makes it virtually impossible.
I can’t stress enough how important it is to not settle for anything less than “smart money” from investors who are genuinely passionate about what you’re building and with whom you’ve built a good rapport. I couldn’t be more grateful to our investors, who continuously provide us with invaluable support when the going gets tough.
Q: What’s been the No. 1 lesson you’ve learned about hiring since you started your company?
Trust your instincts and do your diligence. Even if you instinctively like or believe someone could be great for a role, don’t cut corners with due diligence. Do the reference checks and set challenging tasks as part of the interview process. We’ve had instances where we’ve over-indexed on someone being cultural fit for the team but they’ve subsequently cracked under pressure. We’ve made the inverse mistake, too, to bring someone on who has been an exceptional candidate from start to finish, but we had ignored an inner nag they might not be a fit. Intuition, a stellar interview, and reference performance needs to be in place. It’s simply too costly to make hiring mistakes early on.
Q: Which books, podcasts, educational programs, or other resources have been most helpful to you since starting your company?
To this day, I find Y Combinator’s library one of the most relevant and comprehensive sources of gold dust on all topics. My two favorite VC blogs are the Review First Round Review and NFX’s Founder Library. My two go-to podcasts are Reid Hoffman’s Masters of Scale and Delian Asparouhov’s Operators, where he interviews key operators behind some of the greatest startup success stories. My all-time favorite book with entrepreneurial lessons is The Hard Thing About Hard Things by Ben Horowitz , followed by the biographies of all tech legends — Steve Jobs, Elon Musk, Jeff Bezos, etc.
Q: What advice would you give someone starting out on the journey you’re on?
Work your core.
I recently said this to an expecting female founder, when I realized that would be my advice to anyone. Firstly, this applies to your core mission. Make sure you’re obsessively passionate about what you’re building or you won’t have the resilience to push through the challenging times. The longer you persevere, the bigger your chances of success. That leads me to the second point — take care of your mental and physical health. Your well-being is correlated to your business. This is a marathon, not a sprint.
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