Anurag Gupta of “Failure is an option”

The important thing to realize is that, if you’re not on the path to your goal, you need to change your path or you need to change your goal. Life really is that simple. We just sometimes don’t want to make the hard choices that implies. Many successful people reinvented themselves in a later period in […]

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The important thing to realize is that, if you’re not on the path to your goal, you need to change your path or you need to change your goal. Life really is that simple. We just sometimes don’t want to make the hard choices that implies.

Many successful people reinvented themselves in a later period in their life. Jeff Bezos worked in Wall Street before he reinvented himself and started Amazon. Sara Blakely sold office supplies before she started Spanx. Dwayne “The Rock” Johnson was a WWE wrestler before he became a successful actor and filmmaker. Arnold Schwarzenegger went from a bodybuilder, to an actor to a Governor. McDonald’s founder Ray Croc was a milkshake-device salesman before starting the McDonalds franchise in his 50’s.

How does one reinvent themselves? What hurdles have to be overcome to take life in a new direction? How do you overcome those challenges? How do you ignore the naysayers? How do you push through the paralyzing fear?

In this series called “Second Chapters; How I Reinvented Myself In The Second Chapter Of My Life “ we are interviewing successful people who reinvented themselves in a second chapter in life, to share their story and help empower others.

As a part of this interview series, I had the pleasure of interviewing Anurag Gupta, current founder and CEO of

Anurag is the founder of, a DevOps company focused on incident automation — making it easy to automate away commonly occurring incidents and possible to quickly and safely debug and repair new incidents. Before Shoreline, Anurag was a VP at AWS, where he was responsible for transactional database and analytic services, growing this business a thousand-fold over his time there. He has also been an early member of three startups, with one IPO and two acquisitions.

Thank you so much for doing this with us! Before we start, our readers would love to “get to know you” a bit better. Can you tell us a bit about your childhood backstory?

I grew up in New York City. My parents moved to the US from India when I was 4. It was hard for them, but it gave me so much access to libraries, museums, music, magnet schools, computers, etc. We’re all shaped by our childhood experiences — I’m probably more direct, more passionate, and have more varied interests because I grew up as a New Yorker than if I grew up somewhere else.

After college, I came out to the Bay Area, working at Oracle. While Oracle was already a billion-dollar company, database development was just 20 people. I learned a lot there — most importantly, that you can do large impactful work with a small team. I then did 3 startups and eventually landed at AWS, which was just getting going at that time. It was a great place to build, innovate, and grow services that mattered to customers. After that, I started Shoreline, which is the next chapter in my life.

You have been blessed with much success. In your opinion, what are the top three qualities that you possess that have helped you accomplish so much? If you can, please share a story or example for each.

1. I’m self-critical. That sounds like a flaw but viewing yourself critically is the first step to improvement. When I was young, each year I’d try to find the one thing holding me back the most and spend the year trying to extinguish that flaw. Nowadays, I find the flaws that remain much harder to fix so instead, I find people who compliment my weaknesses with their strengths.

2. I’m creative. I believe that ‘different is better than better’ and, if you want to do big things, you have to approach problems differently than others have in the past. For example, when I started Amazon Aurora, databases had been around for 30+ years. We took a different architectural approach than others which led to being meaningfully better in some ways.

3. I seek clarity. I try to see the world as it is, not as I wish it were. Understanding what is and what should be, seeing the gaps between the two, and charting a path from one to the other is powerful. I find too many people fear seeing things as imperfect will sow dissatisfaction. I don’t see why — it just tells you what to change in a purposeful way.

Let’s now shift to the main part of our discussion about ‘Second Chapters’. Can you tell our readers about your career experience before your Second Chapter?

Most recently, before Shoreline, I was at AWS. Over the eight years I worked there, my team grew a hundredfold and our revenue grew a thousandfold. We built things I hadn’t imagined possible. I developed close relationships. In many ways, I’d carved out an ideal place to work and create. It was very fulfilling.

Can you tell us about the specific trigger that made you decide that you were going to “take the plunge” and make your huge transition?

The important thing to realize is that, if you’re not on the path to your goal, you need to change your path or you need to change your goal. Life really is that simple. We just sometimes don’t want to make the hard choices that implies.

I have a special needs child. When he regressed, it gave my life a purpose to help not just him but also other children like him. The specific trigger for me was when my wife came to me and said, look, you make more money than I ever thought you would, but it is water poured on sand. We’re not going to be able to have any real impact unless you’ve made 50 or 100x that number. That wasn’t an amount I was going to make at AWS or any other large tech company.

I wasn’t on the path to my goal. Since I didn’t want to change my goal, I had to change my path. A startup does have the potential to get me there. Even if most startups fail, the risk is not symmetric. If you succeed, you can succeed big. If you fail, you just go back and do what you would have done otherwise. There’s no reason not to try.

How are things going with this new initiative? We would love to hear some specific examples or stories.

It is early days, but it is going great so far. I really believe incident automation will become a third pillar for production operations just as observability and incident management are today. When I was responsible for at-scale services at AWS, I didn’t get excited when someone gave me one more dashboard or a better process workflow. I did get excited when someone told me that some ticket was extinguished forever and we wouldn’t have to wake up to deal with it anymore.

Shoreline makes it easy to automate repairs to the commonplace incidents that burn operator hours and kill availability. It also makes it possible to quickly diagnose and repair new issues on your fleet as though it were a single box. There’s a lot of deep technology under the covers, but it is surfaced as a simple, easy to use system that feels just like a shell. It is very fulfilling when our customers realize all the things they can do and the time they will get back.

Did you ever struggle with believing in yourself? If so, how did you overcome that limiting belief about yourself? Can you share a story or example?

I struggle with this all the time. Perfectionists procrastinate. Delay is death at a startup, where time literally is money (or runway). The key is to stay focused and do the work immediately in front of you despite the ambiguity swirling about.

What helps me most is surrounding myself with people whom I believe in. I also find it helps to visualize the large-scale best case — people’s shock and delight at seeing something done they didn’t even know was possible — to overcome day-to-day challenges. Finally, even if every day at a startup brings its own difficulties, if I look back a month or three, it is remarkable how much progress has happened. I just need to believe that continues to be true in the next month or three.

What are your “5 things I wish someone told me before I started leading my organization” and why? Please share a story or example for each.

1. You are not your work. It is hard to start a new chapter. Not only because you’re taking on ambiguity and risk, but because you’re dismantling much of how others perceive you and how you perceive yourself. We tether who we are to what we do. Starting a new chapter resets this. Many people won’t perceive you the same way in the new setting. You shouldn’t do the same.

2. Find what you must do. Creating something from nothing is hard. Harder than pretty much anything you’ll do. The only way it is worth it is because you’re going after something important to you. It will help you persevere.

3. Failure is an option. You just need to make small incremental steps to some large daunting goal. The setbacks along the way are recoverable.

4. Burn the places you hide. There are endless reasons not to do something. You aren’t good enough, you’ll be judged, you might fail, etc. etc. You have to find ways to overcome the obligations and fears that are holding you back.

5. We’re all just muddling through. No one has the answers. Listen to lots of people. Figure out what resonates for you.

How can our readers further follow your work online?

You can learn more about Shoreline at I’m accessible as @awgupta on LinkedIn — your readers can reach out to me there and ask me anything.

Thank you so much for sharing these important insights. We wish you continued success and good health!

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