Joining a startup early with Charley Ma

Charley Ma on his experience joining early-stage startups. He was the first business hire at Plaid and an early member of the Ramp team.
February 24, 2024
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Charley Ma is a full-time investor based out of New York City with investments in Apollo, Stytch, Finch, Unit, and Codat. Before that, Charley was Plaid's first business hire and employee #9. He then joined Ramp as their Head of Growth, where he helped them grow from 0 clients to the fastest-growing corporate card in the US.

Watch this if:

  • You’re considering joining an early-stage startup

  • You want to learn what high-signal things to look for and ask about when evaluating and interviewing at startups

Interview Transcription

Kieran: Hey Charley. Thanks for joining me today. Do you want to introduce yourself?

Charley: My name is Charley. I am based out of the New York City area and was born and raised in San Francisco. I am a full-time investor, but before starting my venture capital firm with my co-founder, I spent most of my career as an operator. I worked at companies like Plaid, Ramp, and Alloy and started my career at J.P. Morgan.

Kieran: I reached out because you’ve joined two incredible companies very early on. You were the first business hire and employee number nine at Plaid. You also joined Ramp as their Head of Growth before they had any customers. I know many of my audience members are interested in joining something at the earliest stages, so I wanted to try to capture your experience to the best of my ability. You mentioned you started your career at J.P. Morgan. When did you know you wanted to join a startup?

Charley: Yeah, it’s funny. I stumbled my way into startups. I attribute a lot of that to my time at J.P. Morgan. I originally joined J.P. Morgan in a mid-office, back-office rotational program. So, I was not part of the investment banker program. It was called J.P. Morgan TSS -- Treasury and Security Services. It comprised all of the corporate banking products and services we'd sell to the Fortune 500. So, think payment processing, portals, etc. There, I got a fascinating deep dive into payments and the lack of technology within the bank. I was really interested in how all this money was being made, but it was built on top of 1970s technology. I wondered what was happening from an innovation standpoint? It was funny because, at the time, I knew nothing about startups. I thought I would apply to venture capital because if I joined as an analyst or associate, I would get access to several companies, learn about startups, and figure out the right time to join one. I interviewed at several VC firms and did not get the role. I don't think my background was quite the right fit then. I even interviewed at several larger tech companies. I came across Plaid as part of my research and remember being very excited because they were going to build new products. After a few years at J.P. Morgan, I realized it was not the right time and place to be there if I wanted to learn how to build innovative technology. It was bureaucratic, much slower than I was expecting, and I wanted to go somewhere much faster-paced.

Kieran: When you joined Plaid, that must be a completely different environment from J.P. Morgan. What surprised you the most about working in a very early-stage startup? 

Charley: Oh gosh, everything. When I joined, I was most surprised by how fast-paced things were and how fast decisions had to be made. At J.P. Morgan, I was used to meetings upon meetings to make big decisions, and big is quote-on-quote relative. It's be meetings upon meetings — decks, presentations — meetings to prep for the meetings in order to present upwards to upper management and board members. That was a lot of the work that I was trained to do. I remember two months into Plaid, we had a board meeting coming up. I thought, oh, that's a pretty big deal, right? We'd have one once a quarter. I remember thinking, okay, great, I can help build the presentation, present, and put together a few slides on what we're doing on the business side and what the client pipeline looks like. Everyone, including Zach, our CEO and Founder, who I was fortunate enough to work with early on, was like, no, the max time we can spend given where we are at this super early stage is a day or maybe half of a day before we needed to get this stuff out. In addition to being really fast, it had to be high quality, too. I think that combination was a big adjustment for me. How do you combine and blend speed and quality, especially when you're so resource-constrained as a startup? You have to make decisions quickly and hope they are all right.

Kieran: What did you like most about the early days at Plaid? Do you have any favorite stories or core memories?

Charley: A bunch. It's been such a long time. I remember it felt very pure, if that makes sense -- I think everyone looks back nostalgically at that time. At the time, joining a very early-stage startup was not particularly common or popular. Most of my friends, I would say, went more traditional paths, such as banking, private equity, consulting, etc. The people who moved into tech work at Google and the larger tech companies as their first entry points. I was a bit weird because I joined a very early-stage fintech company in San Francisco when fintech wasn't very popular. It was unique because we were all surrounded by people who were just excited about what we were building. Before the SoftBank super rounds, I remember one day talking with a few of the engineers and asking, what would we do with a hundred million dollars if we received that tomorrow? I literally was like, I don't know what we would do with that much money. It's a crazy amount. I remember the dream as an operator was joining a company and getting it to a billion-dollar valuation. That was the end goal. I think nowadays, and we're resetting with the downturn in venture, but it almost feels weird as to how normalized that became. It became much more accepted for an operator to join an early-stage company. I think it's really good for the startup ecosystem, but I miss the times when I was surrounded by really smart people who were there just because they truly believed in the mission and vision. We were all focused on that at Plaid.

Kieran: You ended up staying at Plaid for five years. You sort of scaled as the company scaled. I think that is pretty rare because fast growing companies often need to hire more experienced people or hire over people because they need different skillsets as they scale. What would you attribute your growth to in that company? What did you do right at Plaid that allowed you to move up within the company?

Charley: Yeah, I was going to argue I didn’t scale well. I think it’s very, very hard; I think I can count 2-3 people who have scaled in terms of their role with a company's growth. When I joined Plaid as an early business person, I had preconceived notions that one day I might run X, Y, and Z for part of revenue, sales, marketing, or whatnot. The more I learned, the more I realized I knew nothing. As we started to scale and hit product-market fit, I realized we needed to bring in really good people from whom I could learn. I made a deliberate shift to use the opportunity to learn as much as possible. I think the thing we did right at Plaid and Ramp was created this exceptional talent density where I could learn from the best operators, execs, managers, ICs, period. I think being open-minded, able to learn fast, and willing to do whatever the company needed helped me to continue to grow and stay with the company. I think there are certain roles that early employees are particularly well suited to. I figured out I don't like running large teams. I love running small, lean teams focused on a singular thing we need to build, which is why I am biased toward working with founders of the early stages. I don't enjoy managing managers. I don't enjoy it when the company becomes a little bit larger, and there are more communications and interactions between different layers of the organization. I think for employee roles I end up doing well in tend to be spearheading new product initiatives and going and fixing things that were perhaps going off the rails because I usually had a good sense of what the founders or other execs cared about across the company, what we were over-indexing towards and also had a lot of context and trust built into the organization to do so.

Kieran: How did you know it was time to move on? Did you realize that you didn’t like running large teams and wanted to go back to the early stages? And that’s why you joined Ramp?

Charley: No, it was honestly random. I very much enjoyed Plaid, but at this point, I moved to New York, helped open up Plaid's new office there, and had a really great team with whom I was working. As a startup, I think you're always trying to fight the entropy of what size brings to an organization. The bureaucracy, the additional effort to communicate, the context needed to operate. You try to operate like a startup, but as the company grows, it gets a bit slower. I started to open up my aperture. I was no longer obsessing about Plaid, trying to keep my job and not get fired. At a certain point, I knew what I was doing and was executing well. I was actually thinking about starting a company. That was my original intention when I joined Plaid and one of the reasons why I wanted to go somewhere early. I was exploring ideas, and one of them was in the APAR, accounts payable, accounts receivable space. I met the Ramp team one weekend and remember thinking this team is way better equipped and smarter than I am about the problem space. I think I have to join this company.

Kieran: You've touched on talent density. I watched some of your other interview recordings, and I know you have mentioned you should try to surround yourself with the best people possible. This may be a dumb question, but how do you know someone is good? Do you have something that you're looking for, or is it just pattern recognition? How do you spot talent density?

Charley: It’s a good question. What is good, right? I think there is a pure IQ element to it. You can be good at different aspects. The framework that I adopted from Plaid and the founders was hiring for spikes. We've talked about it, and you'll hear other Plaid execs talk about it. I very much believe that building a hypergrowth startup is a team sport. It's not a family. It's a team, and you don't build an all-star team by hiring a bunch of generalists who are all-around good at what they do. You hire for specific skillsets and then build complementary skillsets around those teams and functions. So, what does good mean for me? The other way to phrase it is like, what are these people's superpowers? Why are they working on the thing they're working on? Some part of it is a gut feeling. The other part is a cultural thing. In order to build talent density, you need to be extremely deliberate from day one. It's really painful to create a high bar for talent from day one. As an early-stage startup, if you get product market fit, you often feel the pressure to hire people to go do work. There's so much we need to do that we need to hire people. What I often see as a result, I don't want to say lower the bar, but you sort of change what you're looking for. I actually do think it's lowering the bar, right? I think the best founders not only maintain talent density but continue to raise the bar. I think what you look for changes as the company evolves. Some people are great at the early stages but may not necessarily be the best fit for a later-stage company and vice versa. I think you should always have a culture early on where you hire for spikes and be deliberate about why you're bringing someone in, what each incremental person brings to the table, and if they increase the company's enterprise value.

Kieran: It sounds like you're for hiring specialists even very early on. Where do generalists fit into early-stage startups?

Charley: This is kind of a weird statement, but I think to a certain extent, I consider myself a generalist, but there are specific areas I probably spike on. I describe myself as a product-oriented early-stage go-to-market generalist. I will probably not be your best head of sales, marketing, and account management, but I think I could do a pretty good job at all of those things. I have a good orientation around how products are built, what's actually important versus what's not, and how to give that feedback loop to the product and engineering teams. I also have technical tendencies, which help me understand and grok basic engineering concepts so I can talk to engineers and CTOs. So, I think those are the areas where I tend to be good. One framework I like to use is how do you actually become the top 0.1% best in something? For example, I think being the top 0.1% best salesperson is very tough. There is always going to be someone who is just obsessed with it. So, how can I find overlapping areas where I can be the top 0.1%? Maybe I'm in the top 1% in sales and marketing, and from there, I can combine that with a vertical like fintech. I think I would fit in the top 0.1% of early-stage go-to-market people who have sold fintech infrastructure. It is somewhat niche, but that niche ended up being surprisingly large, and that's where I've started to build out edges and specialties.

Kieran: What are good questions that you like to ask startups when trying to get more information to decide whether to work there?

Charlie: Think like an investor. I got very lucky in picking, and I wish I could say I was great at picking and I will say I am because I'm an investor now and that's what I have to say, right? When joining as an early employee, you have a portfolio size of one. You have to get it right. The part you have is the duration of your career. I believe joining startups and entering the startup ecosystem is relatively non-risky now. But joining an individual startup is quote-on-quote risky. So, I think thinking like an investor is important. I would care about the founders, how they met, and everything you could possibly care about as an investor. Almost imagine if you were to put a million dollars or a large amount of money into this company; what would get me to say yes? I think it's really important, but you can also overanalyze these companies. Early-stage companies may not even have a product, customers, or revenue yet. So, there is not much information to go off of. Where I've landed, and to a certain extent, my advice may not be helpful, but I tell people you kind of have to trust your gut. Are you really excited about what they're building? There have to be some other intangibles as to why you're joining this company, particularly early on. If you don't have any other big considerations and you have the aptitude and aperture to go do it, then kind of just go do it. It'll probably fail, but know that coming in. So, one of the things that you have to bet on is the growth potential and team. When there is a high likelihood that the company will fail, the only thing that still compounds is the people you work with. Those people will hopefully bring you to your next job or help you find the next thing to work on. That is the thing that compounds from a career perspective.

Kieran: How do you try to understand growth potential? I know you mentioned you want to avoid overanalyzing it, but are you just trying to understand how pressing a problem this is, or are you doing more research on the market?

Charley: The framework I find helpful is to be extremely customer-centric. I think there are multiple ways to slice and dice the approach, but I think my favorite thing to ask for is a recording of sales or customer calls. I love obsessing through those. I think that is the most high-signal thing you can do when you diligence a company. I want to listen to some calls where the customer call went really well and calls where the client tells them the product is not useful at all. I want to understand your ideal customer profile, who you are selling into, what's the problem your product solves, how hair on fire is the problem set, and how you think about the problem space you're building in. Then, I come to a conclusion about whether I believe this is a big enough market and something I would be excited to build. I think it's a classic mistake, particularly with early-stage startups, to overindex on TAM. I think most investors get it wrong, it's just so hard to figure out. So, I always index towards great teams. Who are the customers you're selling into? I tend to be B2B. Am I excited about the problem set? Do I think it's a big problem set and this could potentially be large? Ok great, that seems interesting.

Kieran: I know I have a lot of university students who are considering joining an early-stage startup. Would you recommend joining an early-stage startup as the first thing you do out of university or do you think it's better to go work at a big tech company, build a skillset, and then transition to startups later in your career? How do you think about the path?

Charley: There's no right or wrong answer. I think everyone I know who has joined an early-stage startup has sort of figured out there path, but I would not actually recommend most people join a super early-stage startup. I frankly would not, I don't think it's worth the risk/reward. I think it's really hard to pick and get it right when you're that early. I think as much as Silicon Valley is meritocratic, but there is still signaling, logos, people, and networks. The entire thing is built on networks. So, I would optimize around a reputable logo or company known for having a good talent density and a high bar from an interviewing perspective. In addition, does it have a growing product or revenue stream? The reason why you're able to grow your career at an abnormal rate with venture-backed startups is because they grow at an abnormal rate and you have to give people things to do, right? You have to give your junior people more responsibility because you literally don't have enough people. Hello, random person who knows nothing. Congratulations, you're running marketing because we have no one else to run it. We need you to do it. So, you're going to do it. If the company isn't growing, that problem doesn't exist. So, that's always my number one criteria. Join something that is extremely fast-growing and has really great people. That is where I would start my career ideally.

Kieran: Can you plug a couple of startups that fit your criteria? Is that a Ramp? Something earlier?

Charley: I think this is where people get overindexed. It could be almost anywhere, right? Ramp is a great example. It has amazing product velocity, revenue growth, and amazing talent density. Some people will say, it's growth or later stage. Doesn't matter. It still has those two things. You still have plenty of room to build, and you're building something worth something, right? You'll get those experiences and be in the environment you seek to grow. I don't have a short list, but I would definitely recommend a Plaid, Ramp, Alloy. All of those are still growing and compounding well, but that's where the diligence starts to come in.

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