I Left My 6-Figure Job at Zillow to Found a Startup. It Was Worth It.

I Left My 6-Figure Job at Zillow to Found a Startup. It Was Worth It.

Rebekah Bastian, 43, grew to become the CEO and cofounder of OwnTrail immediately after leaving

  • Rebekah Bastian, 43, grew to become the CEO and cofounder of OwnTrail immediately after leaving Zillow in 2020.
  • She produced $275,000 at Zillow but now tends to make $60,000 — she stated she took the pay out slash to support her group.
  • This is her job story, as advised to the author Perri Ormont Blumberg.

This as-told-to essay is centered on a discussion with Rebekah Bastian, the 43-calendar year-previous CEO and cofounder of OwnTrail, centered in Seattle, about her occupation journey. It has been edited for length and clarity.

I started off my job as a system manager at Microsoft in 2003. Then I grew to become a person of the first staff members at Zillow in 2005, when I joined as a method supervisor.

About the course of pretty much 15 decades I worked in several places and moved up to vice president of products, then pivoted to vice president of neighborhood and lifestyle. I still left Zillow in 2020 to start OwnTrail, a platform the place girls visualize their lifetime paths, influenced by my reserve, “Blaze Your Individual Path.”

When I started at Zillow there were about 20 staff, and the company was even now in stealth manner — so a lot so that I didn’t absolutely know what they were being operating on when I accepted the occupation. It turned out to be a terrific transfer. I learned so much about escalating a business, innovating in a legacy industry, and becoming a leader.

All through my 15 many years there I began the initial suite of mobile merchandise, developed out a number of income styles, led product integrations from acquisitions, and pivoted to begin their inaugural community-and-society business, which centered on social influence, fairness, and belonging.

I didn’t actually intend to start off a business or depart Zillow when I started out working on OwnTrail in summer months 2019

My book is a pick-your-individual-journey exploration of women’s everyday living paths. Soon after signing with my publisher, Berrett-Koehler, in February 2019, I started off actively playing all-around with what I considered would be a cool ebook-start platform.

I then satisfied my cofounder, Kt McBratney, who was the CMO at the movie-crowdfunding system Seed&Spark at the time. McBratney’s knowledge is in brands and internet marketing — an space of knowledge that was complementary to my product qualifications. Jointly we shaped a vision for what we could make with OwnTrail, and I finished up feeling like I experienced to choose the leap.

two women standing outside with trees in the background

Bastian and her cofounder, Kt McBratney.

Lisa Elliot


It was definitely scary to depart a comfy, safe job that I beloved and a base income of $275,000 — moreover equity and a good added benefits bundle — for no salary in my to start with calendar year of entrepreneurship. But immediately after many months of working on OwnTrail on the side, I realized I had to go all in for it to have the best chance of succeeding.

OwnTrail is a web page wherever individuals go to visualize and navigate profession paths. On the digital platform, people today share milestones across their own and professional life and can check with for guidance from others in the local community. People can be part of and share their daily life visualizations (“trails”) for free, and there are choices to pay back for a regular membership.

a screenshot of someone's OwnTrail

Bastian’s trail.

Courtesy of Rebekah Bastian


I took no wage my to start with 12 months at OwnTrail, and now I shell out myself $60,000 a year

I want to stretch our runway and get treatment of our wonderful workforce of 8, so my own wage has been a parameter I’ve been capable to be flexible on. Not each individual entrepreneur has that possibility, and I’m unbelievably grateful to have that economical privilege from getting an early employee at Zillow.

We’ve raised $1.2 million so much from angel investors and The Home Fund, and I have personally invested $100,000. I was not keen to budge on our values (like the fact that we will under no circumstances promote people’s info to advertisers) or on possessing a cap table — a checklist of all the securities a company has issued and who owns them — that represents the variety of our group. For the reason that of that, I had to get to out to far more than 300 buyers right before closing our preseed spherical. It was mainly a quantities match of discovering traders that had been the suitable suit for us.

There had been occasions when the fundraising procedure experienced me genuinely discouraged, but we ended up with amazing traders and a cap table created up of 68% gals and 49% buyers of coloration. The intentionality was truly worth it, and we are exceptionally disciplined now in how we expend individuals tough-attained resources. About 90% of our regular spend goes to salaries, and the rest is administrative.

To get over the rejection, I figured out to hold two conflicting truths at as soon as: The company is going actually properly, and fundraising is definitely tricky. Somewhat than likely by way of the roller coaster of feelings concerning the two, I acknowledged that these two points usually are not necessarily correlated.

The entrepreneurial journey is wild

It will stretch you to your limits, and you’ll encounter the greatest highs and cheapest lows — in some cases in the same hour. For instance, I’ve gotten back-to-back again notes from a neighborhood member saying that OwnTrail transformed her daily life and from a probable trader stating that they do not consider we are going to make it. Simply because of that, I imagine it can be incredibly critical to be developing something that you might be so passionate about, you just have to do it. You will will need that passion to get by the challenging sections.

I experienced a ton of options to be an “intrapreneur” at Zillow, starting new initiatives, items, and businesses from scratch. I assume that, coupled with my encounter increasing with the firm from a stealth startup to a significant platform, gave me a large amount of the tools that I use now as an entrepreneur.

Also, surrounding oneself with the proper persons is crucial. There’s no way I could do this with out my cofounder, my team, the other founders I have become near with, and the greater OwnTrail group. Many of our staff members and investors came specifically from the OwnTrail group, which was amazing since they now recognized and beloved what we have been setting up.

Want to share your career journey? E mail Lauryn Haas at [email protected]