The Obsession Tax: Building a Billion-Dollar Unicorn in 16-Hour Days

"You are committing to an obsession," Tim Hwang warns anyone considering starting a company. At 30, he's already the youngest Asian American publicly traded CEO on NASDAQ, having built FiscalNote from a dorm room idea into a billion-dollar unicorn.

FiscalNote collects and analyzes laws and regulations, serving clients from the White House to the CDC. But behind the impressive client list and public offering lies a decade of 16-hour days, near-bankruptcy moments, and the kind of relentless focus that most people can't sustain.

In this candid interview, Hwang reveals the unglamorous middle part that movies skip over – the people problems, the cash crunches, and the psychological toll of building a unicorn startup. His lessons on timing, hiring, and maintaining founder mentality offer a rare glimpse into what it actually takes to scale from zero to billion-dollar valuation.

Tim Hwang: Building a startup requires the founder to have a very strong sense of mission. Why does this company exist? What purpose does this company serve? That mission is gonna be what draws people to the company, and the people that are attracted to that mission are gonna find your company very, very compelling because life is extremely short. In that short amount of time, do you want to go to a 9 to 5 job making somebody else wealthy, or do you want to come and change the world?

Now imagine this, you're a software engineer making a decent amount of money, 6 figures, and you get a cold email from a startup founder. So I have this company. The product is not built. We just raised a small amount of money. Do you wanna quit your job and come work for us? I'm gonna take a huge pay cut and maybe a little bit of stock. 90%, 95% of people would say no. I mean, why would I do that? I have such a comfortable life.

Your job as a founder or CEO is to convince that person that this company is gonna be a unicorn and to look them straight in the face and say, you're gonna quit your job, you're gonna take this opportunity because it's a once in a lifetime or twice in a lifetime opportunity, and you're not gonna regret it because high quality people are drawn to high quality founders. If you essentially take capital and you hire a bunch of people or low quality people, then the company is not gonna succeed.

Tim Hwang: For FiscalNote we typically almost in every case with the exception of one or two have acquired founder-driven companies. For me, founder-driven companies are very different. They're very special because the founders themselves picked each person individually in their organization. They also have a very strong sense of responsibility of making this company a success. They also typically have taken some level of venture capital. There's sort of this very aggressive speed mindset, and they typically tend to treat their employees very, very well, almost like a family-like environment.

If you combine that experimentation and bias for action and family-like environment and sense of ownership, that's a really great culture to have, and it's something that we had at Fiscal Note for a long time. I don't know what it is, but I think when we were very, very young and we had a very good team, we had computer science PhDs quit their jobs. We had people who had come from the military. We had this very strong sense of mission even though we had a small amount of time.

I think that very quickly we built a team that was gonna stick together for good times and bad. At fiscal note, we were probably working 16 hours a day, 7 days a week for almost 2 years. I told my employees actually I need you in the office somewhere between 9:30 and 10, 7 days a week, every single day. Right now at a Series A stage company where you have 18 months to basically hit a particular milestone, you need to be in the office 7 days a week.

Tim Hwang: Just because you receive investment doesn't mean that you're gonna succeed. It's actually higher likelihood that you're gonna fail because at this point, you've taken the money from the investors and you now have to spend it, and you have to spend it very quickly because the market is changing, the landscape is changing, competitors popping up. Investors expect you to generate a return in a particular amount of time.

The timing is probably the most important thing in my opinion, and it depends on the sector. And technology, the good thing about technology is that these timing trends happen all the time. 2007, Steve Jobs gets up and he introduces the iPhone that launches a whole next 10 years of mobile investing, mobile companies, mobile startups, that trend, you have to be able to jump on it immediately.

From a startup perspective, when you pick the idea, you have to understand not just why does this company exist, but why now? Why is this timing right now the perfect timing for the company. In my opinion, actually, having done startups now for almost 10 years, I think that's probably one of the most important questions that founders have to ask themselves why is the timing for this exactly right now? Why wasn't it 5 years ago or 10 years ago? Why isn't it 5 years from now? And I think that if you can get that timing exactly correct, then the startup should be able to ride the tailwinds of some general market trend.

Tim Hwang: The biggest decisions that we made were always about people. People problems are what really, really break down companies, particularly for Series A or Series B companies. Those companies have significant management issues. If you watch the movie The Social Network's really interesting. They go from like their dorm room at Harvard and then literally 10 minutes later they're like in this massive office with hundreds of employees, right? I was just thinking in my head like what happens in the middle, because in the middle there's so many problems and there's so many people problems.

And I remember when I was a Series A founder, Series B founder, every time an executive would quit, I'd have to jump in there I have to manage the entire team myself and so suddenly I go from managing maybe like 4 or 5 people to managing like 20 people overnight. I have to do damage control and all these different things and so startups are, it's a very, very analytical job. It's very self-reflective.

It's almost like swimming. You have to constantly know what your limits are, what your energy level is all these different things. I think startup is the same thing, right? Everything stops and starts with you. You founded the company, it was your idea you take responsibility at that level you have to know what are my strengths, what are my weaknesses, where am I gonna fail? Where are my blind spots? And if you don't know what those fundamental kind of personality traits or flaws are for you, then it's gonna be very hard to do your job.

Tim Hwang: And if you can really hone in on what that is, that kind of mentality is constant because when you make a mistake you put that into your frame. Where you make another mistake, you put that into your framework. For instance, for me, I have a bias when I'm hiring executives, right? I look very heavily at the resume and I don't interview enough for particular skill sets and so I've definitely made that mistake almost one too many times where you overhire on the resume and you under hire on the personality traits.

I had to train myself to remove that bias from my head to make better decisions. That again is a very introspective thing. You just have to constantly be thinking about that on a daily basis.

Tim Hwang: I spent the entirety of my twenties building a company from the moment I woke up to the moment I went to sleep every single day I was thinking about how to make the company successful. When a lot of people ask me, Oh, should I start a company? Should I start a startup, I just tell them, you really need to know what you're getting yourself into. I mean, you are committing to an obsession.

You need to make mistakes, get to a point where you have significant hardship, and then you essentially learn from that hardship. There are times when I was starting fiscal note Series A, Series C, Series D, the times are very, very challenging for sure. Right before our Series A closed as an example, maybe about 6 weeks of cash left in the bank, I had to call all of our employees in and I had to tell them that our Series A fell through and I need to go back to Silicon Valley. I need to try and raise funding again.

Those types of situations when you're basically put face to face against like complete failure are the places where you grow the most.

Tim Hwang: The last couple of years in fiscal note, I'm definitely growing as a founder, but the thing I really want to do is continue to maintain my early stage mindset and be very, very plugged into the early startup trends and investment trends and the like. That I think is becoming more difficult for sure. And I'm definitely trying to continue to keep my 0 to 1 kind of founder mentality as much as possible.

Tim Hwang: When you succeed, it's an unbelievable feeling. I'm lucky to be the youngest Asian American publicly traded CEO on the NASDAQ or the New York Stock Exchange. And when I reflect upon the last couple of years of my life and what it took to get there, I think that it's definitely an amazing sense of accomplishment.

To be honest, I definitely feel like I missed out on a lot of things, right? I mean, but you sort of give something up to gain something else. And I think that at least for me, it was definitely worth it in the long run. I don't, I definitely don't regret it for sure.