Charley Ma With Grace
Welcome to With Grace. This week, we feature Charley Ma, Co-Founder and Managing Partner at Pathlight Ventures. A repeat early operator, Charley was instrumental in scaling Plaid, Ramp, and Alloy—joining each at the ground floor and leading go-to-market through moments of breakout growth. Now at Pathlight, he backs early-stage founders with conviction, speed, and deep operating empathy, with a focus on fintech, B2B software, and applied AI. For Charley, great leadership starts with decisiveness: “I tend to believe that making a bad decision fast is better than making a good decision slow.”
What’s an unexpected tool you love?
Aranet4 CO2 monitor! You’d be surprised at the (lack) of airflow that a lot of rooms have - whenever it goes red and tells me the CO2 concentration in a room has gone up, just reminds me to open up a window and get fresh air. I definitely notice a difference in brain fog when it’s red for a period of time vs. green!
What’s a daily ritual you swear by?
Color coding my calendar! Every day, I look at the week behind and the week ahead and color code my calendar into categories of meetings (first founder meetings, networking, investors, LPs, internal, portfolio work, etc). On a monthly basis, I try and think through which meetings I should be doing more of vs. doing less, and actively try to change my calendar and prioritization.
What’s something new you’re trying?
Trying https://wisprflow.ai on more day-to-day workflows to see if I can get around some of the writer's block that I sometimes have, or just get stuff done faster. I still find it a little bit awkward, but I do find that it actually helps me practice speaking a bit more, which is something I'm always working on.
What’s an emerging technology or innovation in your field that you’re watching closely?
I've been quite excited about technology that was innovative in the last 10 years around vision processing and machine learning. Due to the influx of cash in the AI / chip market, we’re starting to see the commoditization of hardware. As a result, I think we're finally starting to see more mass-market use cases for vision processing. In particular, I'm excited about physical world observability products!
What’s a key quality or trait you believe is essential for leaders?
Speed of decision making. I tend to believe that making a bad decision fast is better than making a good decision slow.
How do you approach decision-making in high-stakes scenarios?
I first try to triage whether or not this decision is truly a one-way door or a two way door. If it's a two-way door, I try to make the decision as fast as possible with whatever data that I currently have or can get very quickly in order to move on to as many one-way doors as possible. Where decisions are truly irreversible, I want to understand the level of impact across whatever metric I think is most important / relevant, make sure that I'm bringing in all the right people with the right context, and be very explicitly clear on how the decision is going to be made. For these decisions, they tend to be more top-down than consensus-driven and I think it's important to be explicit on what type of decision that I will be making and explain why to the team to get them onboard as fast as possible.
What’s the best advice you’ve received, personally and professionally?
It's hard to be in the top 0.1% of one single thing, but it's much easier to be in the top 1% of two things. The intersection / venn diagram of the two can get you to 0.1% and if that intersection is valuable; that’s how careers are made.
What’s something you had to learn firsthand to truly understand?
Being on a sales quota! Being an IC sales rep and seeing my number go back to zero every single quarter, no matter how well I did the previous quarter, helped me build much deeper empathy for all sales people. Everything at some point turns into a sales role and I joke that as a VC investor now, I’m basically a glorified SDR that’s on quota to hopefully find great founders!
