From Enterprise to Venture

Alex Smith, Entrepreneurship Editor

Alex Smith (MBA ’23) interviews Angela Son (MBA ’23) and Kevin Miao (MBA ’23), two incoming RC’s who left successful careers at large corporations to join startups. Son’s account at an early-stage venture and Miao’s experience in hypergrowth give unique insight into life at a startup.

Angela Son (MBA ’23) is an incoming RC who grew up in Vancouver, Canada. She attended UBC and, upon graduation, worked at McKinsey, Calgary for two years. For the past three years, Son has been working at Parallel Domain, an early-stage, venture-backed startup based in San Francisco.

What is Parallel Domain and what was your role at the venture?

Their mission is to create synthetic data or simulated data for all kinds of computer vision applications and to help develop the next generation of computer vision algorithms safely and efficiently.

I joined as the first business hire. I think I was employee number five or six. My role evolved so much as the company itself evolved.

In the beginning, when I went in, my title was head of business development.

We were so early as a company and we didn’t quite have product market fit so it was a lot of [thinking], okay, we have this technology, we have some customers, we’re not exactly sure how to take this and go to market with it. So, there were a lot of initial conversations with customers. I would prepare indexes and kind of learn the ropes of enterprise sales.

Then there were product strategy types of questions that needed to get answered. That’s when my title changed to leading product and strategy. I remember launching this huge initiative to go interview a bunch of different potential customers in the market [to understand] the different user personas, what kind of pain points they have, and how we could use our technology to potentially help address this.

Then my last role was head of strategy and operations. Other companies might call it biz ops or chief of staff. My goal was to answer [the question] “what are other big problems that we have as a company, whether it’s internal or external?”—Let’s go build out those functions or those processes.

What was your favorite part of working for an early-stage startup?

I think the really exciting but also really scary part of being at a startup, especially at an early-stage startup, is everything you do counts for the growth and survival of the company. I have to preface, yes of course the work you do as an analyst at McKinsey or wherever, that also counts, but you also have multiple layers of someone checking and gut checking your work.

At a startup, it is just so raw.

Regardless of whether the thing that I am doing is right or wrong, I still have the ability to put it out somewhere, get feedback immediately, and change the course of the business in small and big ways.  Sometimes that might be wrong, because I don’t have as many checks and balances, but at least I have the autonomy.

What surprised you about being at an early-stage startup?

I think first, especially coming from a professional services industry where every single word and punctuation you put out really matters for the brand image, I felt so uncomfortable in the beginning about not spending as much time beautifying the slide. Smaller details like font do not matter as much with startups. It’s more about the content that’s out there and being able to test and iterate really quickly.

The second part was the implication of the lack of structure, less that I didn’t know what to do, but more that I didn’t have very many validation points.  

More often than not, a lot of the things that I was doing, we were all kind of guessing and making best effort choices. Of course, when we needed to, we pulled in our network of advisors, and that’s why it’s nice to be in a venture backed environment where you have access to these people, but a lot of the time I didn’t have the validation I was used to getting in a structured environment. Fundamentally in the first six months I [questioned] “am I doing well?”

Am I good at my job?

Because there was no definition of good.

You mentioned you hope to start your own venture. Can you tell us about it?

I just know that, regardless of what I do, I am going to work hard and I am going to try and do the best in whatever that area is. So I think especially with the pandemic—I personally had a health scare within the last year and a half, that was a real catalyst for me to think “okay, well, if I am going to work hard regardless, why aren’t I putting that energy into solving a problem that’s very personal and relatable to me?”

I’m still exploring. I think there are a few key themes that I’m really passionate about. One is sustainability. And number two is women’s health. Or perhaps [the] intersection of the two topics. I’m excited to explore those topics while at HBS.

Do you have any advice for anyone looking to join a venture?

When I talk to other people, I usually ask them what are [they] looking for in [their] next step. They usually list 5-6 things.

As you know, in life you can never optimize successfully for five different things. I always ask them “if the next step of your career is the title of the next chapter in your life—it has to be one word or one phrase, what is that one thing that really matters to you? Is it the industry, is it the size of the company?”

There are so many startups out there, it’s so easy to boil the ocean and not know, it’s just really easy to get overwhelmed.

If you were an animal, what animal would you be and why?

I think I would be a turtle. So, there’s a few different characteristics of a turtle that I really like. One that really resonates with me is, depending on where they are, turtles can be really slow and derpy, or really fast and graceful.

In the water when they swim they’re actually super-fast and super-good at what they do. Maybe not on land where they are waddling around. I think there’s just like those kinds of examples of duality of turtles that I really like. Like, when people ask me are you competitive, I say I’m selectively competitive, like I don’t get upset when I lose in certain games or whatever, that’s fine, but there are certain things that I care a lot about, that I will put all my energy into.

And two, I’m like a slow and steady type of person. Whenever I go hiking, I’m always the last person in the tail of the group but I never give up, I always finish.


Kevin Miao (MBA ’23) is an incoming RC who grew up in Connecticut. He attended Bowdoin College and then spent seven years working as a trader at Citigroup. Over the summer, he left Citi to join Capchase, one of the fastest growing Fintechs in New York.

What is Capchase and what was your role at the venture?

Capchase is a leader in the revenue-based financing space, specifically focused on venture backed software companies and others with strong recurring revenue bases. Essentially the core product advances against future contracted revenue, so you can get non-dilutive capital upfront versus more extractive options like venture debt or additional dilution via equity raises.

When I initially applied, they offered me a full-time role as Director of Business Operations, which I seriously considered for nearly the entire summer even though it meant giving up HBS. Eventually, however, I decided I had to come and pursue my own idea.

Technically, I came in as an Operations Manager, but I basically did the other job. I was in charge of revamping the underwriting system, helping the engineers automate it, instituting a portfolio monitoring system, so really kind of bringing in more of the, I don’t want to say traditional financial services perspective, but kind of structure and processes around some of these early lending decisions, as well as helping them think about risk.

What was your favorite aspect of working at a startup?

My favorite job ever was driving an ice cream truck around in Connecticut during college. You could end the day, and you could do nothing. You just wouldn’t make that much money that day because you only hit the beach like two or three times.

Or you could really, really hustle and make a bunch of money, but you would be really, really grinding all day. There’s a direct correlation between the input and the output, and I felt like that was often the case for sell-side trading.

The problem is that, in that environment, you’re just so used to operating on your own and maximizing for your own output, which is very different from maximizing for the output of a team in the context of an organization. Being at a startup, where you’re actually able to understand how you fit in across the broader organization and, more importantly, how you can influence the direction they go, was really awesome.

What surprised you about working at a startup that was experiencing hypergrowth?

I think dealing well with uncertainty was huge. Even for me, as a trader, we’re nominally making decisions where you know many of them are going to go awry, [but] you still have a process that you’re following. The process was basically learned into you through [the] osmosis of following all these other people.

Then you use that framework to make a bunch of decisions which is good in many ways, but it’s also constricting.

Then to be at a place like Capchase, where you know you don’t have those frameworks, you’re developing those frameworks as you go, but you’re also developing them with an imperfect idea of what you’re trying to optimize for.

You don’t know how the context is going to shift, how different resources are going to be moved around the organization, or even how organizational priorities will change. It’s so exciting but it also took me some time to adapt to that environment.

You have had a successful career working at Citi and then Capchase. What stands out as the major differences in working for a large established corporation compared to a startup?

I read this book, Do Dice Play God? about introducing randomness. If you think about outcomes as a three-dimensional plane, many people have personal processes that get them to a local high. Then they look around and they are like okay, well, I’m at the best place that I could be right now. [This] is as good as it is going to get, because when I look around me, I don’t see anything better.

But then introducing randomness, constantly having to deal with different situations, being plucked off one place in this three-dimensional map and then thrown to the complete other side, can create outcomes where you identify the absolute peak.

You realize that maybe if I introduce this randomness, I’m tossed somewhere completely new where I optimize and find a new, higher peak, then I’m at a place where the process is 10 times better than before, but I wouldn’t have ever gotten there because I didn’t have the incentive when things were running smoothly enough.

Which is something that I found at Citigroup constantly.

When I deferred last year, for the last four months our first-year analyst was unable to be with the team. I was like “alright, well I know I’m leaving, so I don’t want to shunt off this responsibility to others. I’ll just do it myself.”

To fulfill those duties, I was doing the same exact thing with the same exact technology as I was seven years ago when I was a first-year analyst.

That’s the epitome of this problem. It’s working well enough, and I don’t think that I need to do that much better, but I know that it could be better. There’s just no accountability, there’s no reason or there’s no belief that you could influence something like that at a place like Citi, whereas at Capchase, that was every day.

You mentioned that you are considering starting your own venture. Where are you focusing your energy?

When I had to make this decision between HBS or staying at Capchase, the one thing that really kept sticking out in my mind was a conversation with my first boss at Citi.

I was telling him about Capchase. He was like oh that’s really cool, I think you’re going to do great, but that’s not what you told me about why you were going to go to business school before. You always used to ask “how am I going to use finance to help the little people?”

That really stuck with me.

When I would walk around New York, I would see commercial real estate buildings, every car, every loan, every residential mortgage, they are all touched by the securitization industry. The current capital markets platforms, the opacity and inefficiency that gatekeeper broker dealers surround themselves with, are a tax that’s extracted on each transaction and the proceeds go to pay someone like me to keep these things complicated.

In other contexts, like Airbnb vs. hotels, Uber vs. yellow cabs, we see platforms that leverage technology to make things simpler and more transparent. Obviously, these platforms all extract take rates, fees and stuff like that, but the core concept is still a simple, a transparent platform that’s facilitating these transactions amongst supply and demand nodes.

My goal is to come here, figure out how to build a tech-enabled capital markets platform in the context of our regulatory regime today, maybe a mix between one of the electronic trading platforms that already exist like Market Access or Tradeweb, but with an actual bank and balance sheet behind it.

I’ve been really obsessed with that idea for a couple of years. My ideal dream scenario would be to come here and find someone who is also interested in doing that.

If you were an animal, what animal would you be and why?

I would definitely be some sort of mountain cat. I don’t really know anything about the animals themselves but one, my last name is Miao, so it had to be some sort of feline-related thing.

And at least from what I understand about them they track for a while, and then they pounce when the opportunity presents itself. They feel fairly confident about their ability to succeed. I would say I am fairly methodical about decisions that I make, but then when I make them, I’m all in, and it’s because I think that I’m making a calculated bet that’s going to pay off.

Alex Smith (MBA ’23) is a dog mom from Texas. She previously worked for Chevron Technology Ventures helping startups to scale. Skiing with friends, listening to the Energy Gang podcast on long walks, and singing Billy Joel on road trips are some of her favorite pastimes.