How a laid-off AI enthusiast pivoted to become a founder — while holding down a day job

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Jacky Liang knew he wanted to be in tech, but had trouble finding his groove at first — until he dove into AI. 

The Drexel University alum pursued computer engineering because it allowed him to learn about both hardware and software. His first job out of college was as a software engineer, but he quickly realized that he didn’t love coding as his full time job. 

Wynnewood-based Liang has tried many roles in his career, including being a product manager, a solutions architect and an AI engineer. Despite going through multiple rounds of layoffs over the years, Liang said that ultimately led him to finding a passion in AI. 

He never would’ve had the time to pursue that interest if he remained at his solutions architect role, he said. 

Earlier this year, Liang became a senior developer advocate or as he calls it, “software developer that yaps a lot,” at AI storage company Pinecone. This role involves writing code and sharing it widely, like at conferences and on social media. Now, he’s a developer advocate at cloud platform Timescale. 

His side hustle, however, has led him to entrepreneurship. Earlier this year, he founded Answer HQ, a tool that consumes companies’ data and builds AI chatbots to answer customer service questions. Liang pursued the startup after being laid off in September as a distraction from job-hunting stress. Now he’s juggling the growing platform along with a new full-time role.  

The company acts as another outlet for his AI obsession, which bleeds into his personal and professional lives wherever he can fit it in. Liang also writes about AI trends on his Substack and posts about it on social media. 

In this edition of Technical.ly’s How I Got Here series, Liang discusses his passion for AI and how getting laid off helped him start his own venture.

This Q&A has been edited for length and clarity.

What do you like about the tech industry?

It’s really about the constant pace of improvement, of people being interested in things, building cool stuff and then releasing it to the world. 

We have things like open source, in which people literally give out free software that you can use to implement your own projects, no strings attached. It’s just very common for people to just share knowledge like that. 

I really enjoy that type of quality where we’re working for something a little greater than just ourselves or just about money. It’s a very open industry, where, if you’re passionate, if you’re curious, you probably can find a job or people that resonate with you.

How did you find a role that fit you? 

It was definitely a lot of trial and error. If someone looks at my resume, they will see that I’ve tried many things. 

It’s pretty common for people to not know what they want to do, at least straight out of college or even after being in the industry for a while. It’s important to try different things if you think you don’t like it and to just trust your gut. 

I also went through two layoffs during a tech downturn. It’s important to just stay strong. It’s also important to be persistent and to be resilient, especially when things aren’t going great. 

Why did you start Answer HQ?

Honestly, it started during a pretty rough patch — I got laid off in early September. While prepping for interviews and sending out applications, I decided I would finally solve for a business problem that I see all the time: small business owners and early-stage startups drowning in customer questions while trying to run their companies. 

Instead of just anxiously waiting between job applications, I poured my energy into building something to help (it also helps distract from the negative emotions of being laid off).

What’s it been like running a startup? 

The startup journey has been wild yet exciting. 

My first paying customer was actually a friend who straight-up refused to use it for free because it was helping his shop so much. Having someone believe in what you’re building, especially when you’re spending your days interviewing and your nights coding — that hit different. 

I actually also just started a new role at Timescale last week after a full month of job hunting. Throughout September to now, I was basically living two lives: prepping for technical interviews and building Answer HQ at the same time. Oh, also training for bouldering competitions and being a partner. 

How does your founder experience and day job fit together?

These days I’m juggling the new job while running the startup in my off-hours. One day I’m coding, the next I’m chatting with shop owners on Reddit or friend’s referrals trying to understand their headaches better.

Every time someone tells me they’re saving hours on customer service or seeing more sales, it reminds me why I started this in the first place. It’s not easy juggling so many responsibilities at once but it’s real, and I wouldn’t have it any other way. I hit my fifth paying customer today, and it’s a complete blast getting that subscription notification every time. 

Building the startup also helps a ton in my daily job as a developer advocate at Timescale, because I get to learn more about technology that I will use at work, often in ways that I don’t get to in my day-to-day because there are urgent tasks to be done. 

What I’m building for Answer HQ is exactly the type of stuff I need to know and use at work, so there are dual benefits on both sides. The external learning of building a real application solving real business problems is underrated in how helpful it is for my day job. 

How did you become interested in AI?

I got into AI around the time that I got laid off from Oracle. This is around the time when ChatGPT came out. I started playing around with it. I started reading about it. I really started exploring ChatGPT, large language models and how to use it in as many ways as I can in day-to-day life.

Eventually, an opportunity came up where I could possibly use it as part of my job. It became an opportunity for me to play with it and use it professionally to help my coworkers be more efficient. 

I use AI as much as I can, both in my personal life and professionally, and just try to keep up to date by reading articles. 

Why are you so open to incorporating AI into your life? 

There are some very valid points coming from the anti-AI crowd. One is, is AI going to take our jobs? I think that’s a very valid concern. 

As AI advances, I think there will be a lot of opportunities where AI starts being better than people in certain parts. The other thing is that AI doesn’t sleep, it doesn’t get tired, it doesn’t get bored. It works as long as you want it to, which is both a good thing and a bad thing because people need to sleep. 

On the bright side, from what we’ve seen in the past, I think AI is actually going to be more of an augmentation of what people can do. 

The reason why I do enjoy using AI and why I use it is it just makes me more efficient. It augments what I’m able to do because I have a very clear idea of what an outcome for a project or a product looks like, but I might need a little help. 

What advice would you give people starting their tech careers? 

Be curious. Build stuff. Explore your curiosity. Embrace failure. Don’t let downsides affect you too much because it’s a natural part of anyone’s career. 

What advice would you give to people who are new to AI?

Just start using it, just start playing around with it. Even if you think AI is a hyped-up technology, it is actually a good idea to see what it is good at and to see what it is not good at. 

I have a very clear idea of what AI sucks at, but I’m also pretty clear on, based on a lot of my usage, what it is good at. I try to not use it for things that it sucks at, like generating art and creative writing, but then use it for things where it is good at, which are, critiquing, proofreading, brainstorming and summarizing.