Ask the Expert: Comfortable but bored at a tech giant? Consider key risks before the startup leap

It’s not easy making the leap into the world of tech startups, especially when it comes to leaving a comfortable job at a big, established company.

As with any major change in life, it’s important to understand and evaluate the risks before making a major move.

Rebekah Bastian is a tech executive, entrepreneur, writer and multi-disciplinary artist, currently serving as SVP of product and marketing at Glowforge. She previously made her own risky moves to join startups, first from Microsoft and then from Zillow.

Bastian founded the social timeline platform OwnTrail, which was acquired by Teal, and spent 15 years at Zillow, with roles including VP of Product and VP of Community & Culture. She wrote the award-winning book “Blaze Your Own Trail,” is a Forbes contributor and is an investor and advisor to technology startups and venture funds.

Ask the Expert is a recurring GeekWire business advice column featuring different voices from the Pacific Northwest tech community, answering questions about an array of topics. It’s inspired by common questions from tech workers and entrepreneurs.

Do you have a good question, or are you an expert that wants to contribute to a future column? Email us at tips@geekwire.com. 

Q. I have an incredibly comfortable, stable job as an executive at a local tech company (not naming names, but it’s one of the big ones). I’ve been here for years, am well respected, and get paid really well. The problem? I don’t feel as challenged and motivated as I once did. I see some of my friends building or joining startups, and I feel a little envious of the innovation and excitement they’re experiencing. How do I decide if I should take the leap into the startup world? Thanks, Comfortably Bored.

Rebekah Bastian: I’ve definitely been where you are … twice! 

The first time was a pretty easy (and in hindsight, smart) decision — I was still an individual contributor, working on Microsoft Office Outlook, and was low-key bored out of my mind. Also, I couldn’t stand the commute from Ballard to Redmond any longer. So I answered an ad on Craigslist and took the leap to a tiny, stealth startup called Zillow. That was probably the most successful leap of my career, leading to 15 years of growing, learning and earning. By the time I left that tiny startup, it was a publicly traded company with 6,000 employees, and I had held multiple executive roles across several areas of the business. 

My next leap was much scarier, with much more to lose. During my last years at Zillow, I wrote a book, “Blaze Your Own Trail.” That book ended up turning into the idea for a startup: OwnTrail. I had explored plenty of startup ideas before that, but always managed to talk myself out of them. This one I couldn’t get out of my head, and I ended up feeling like I had to see it to fruition. 

This is a good point in the story to introduce how I think about risks. While most accomplishments in life involve taking risks, not all risks can be evaluated in the same way. I break them into three categories: 

• Physical risk: the decision you make could have life-impacting consequences. This could be a recreational choice, like whether to go bungee jumping, or a health decision, like carrying a high-risk pregnancy to term or working in a hazardous environment in order to make ends meet. With physical risks, you need to take into account probabilities, mitigations and worst case scenarios. 
• Financial risk: the decision you make could impact your livelihood. Financial risks can be largely assessed with math. How long can you live without a salary, or with a reduced one? How much do you need to borrow or raise? What are you willing to live without in order to take the risk you want to take, and for how long? It’s important to note that there is inherent privilege (or lack thereof) in the calculations available to you.
• Reputation risk: the decision you make could damage others’ perceptions of you. This could include speaking in front of an audience, showing your creations to the world, or attempting something that you might fail at. There are some mitigations to reputation risk, like learning, preparation, and finding strong communities to lean on. But the most important thing is to understand that no one thinks about you as much as you do. If the worst case scenario for the risk you want to take is that you’ll look stupid if you fail, it’s probably a risk worth taking. 

For most startups that you might be considering (unless you’re thinking of building the Uber for shark rides), you’re probably most concerned with financial risk and reputation risk. So I recommend that you do your math, and embrace the possibility of failure. 

The nice thing about the mathematical assessments and structural mitigations that can be done around financial risks, is that you can usually make a pretty informed decision. You can end up saying, “I won’t quit my day job until I have x paying customers, or until I have raised y in funding for this idea.” Or you could say “I’ll try to bootstrap this for x months, and if it doesn’t reach y in revenue by then I’ll get another job.” 

And that possibility of needing to get another job … It isn’t the end of the world. The more you fail, the more you realize that it generally doesn’t impact people’s perception of you, and you gain a whole lot of powerful experiences and lessons in the process. 

I ended up building OwnTrail for four years, meeting the most amazing people, learning more than at any other point in my career … and ultimately having to sell it because we ran out of money in a brutal venture market. And you know what? I wouldn’t trade that experience for the world! 

When I look back at how those risks played out for me, I think my assessments were pretty spot on. I never dipped under what I could afford to lose in our savings, and found an amazing job immediately after the acquisition that pays better than my pre-startup roles. And while the startup trajectory didn’t go as I had hoped, I was never made to feel like a failure by anyone – including my investors, employees, or most importantly myself. 

All of that is to say: if you’re feeling the call to a new startup adventure, do your risk analysis and mitigations, and then take the leap! You’re clearly smart, capable and resilient, and you’ll land on your feet regardless of where the journey takes you. Enjoy the ride! 

Previously: 

• Working remotely vs. in the office — which actually works better?
• What are my career options at a slow-growing software-as-a-service company?
• How should I monetize AI agents?