On Being a Founder: Office Hours with Vlad Shulman
Welcome to Merit Office Hours! This week, we’re chatting with Merit investor Vlad Shulman about his experiences as a founder. If you’re new to tech, what a founder does, what they think about, and how they operate can be opaque. We pulled back the curtain by asking Vlad about his current work as a founder and previous role as co-founder and CTO.
Vlad Shulman is the founder of Stork Oracle Network. Prior to Stork, he was the co-founder and CTO of Retain.ai. With almost 15 years in tech, he has worked both in product management and software engineering across adtech, enterprise, and Web3. He is based in San Francisco, California.
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Our conversation has been edited for length and clarity.
Rachel Spurrier: You have been a co-founder and CTO, and you are currently the founder of Stork. What is it like to be a founder/co-founder, and how would you describe that experience to someone who is new to the tech industry?
Vlad Shulman: Being a co-founder was a good segue into being a founder. In my experience, there are many more responsibilities involved with being a solo founder. If you’d asked me 10 years ago, I would have said that neither was particularly interesting to me. It all felt like a lot of “20% doing what you’re supposed to be doing and 80% paying bills.” [laughing]
I’ve changed my mind about this a lot, having done it. I think either way, for better or for worse, being founder or co-founder means that the buck stops with you.
I used to have this posture where I would point out a problem, and then feel like maybe it wasn’t my responsibility to come up with a solution. If felt useful to bring [the problem] up, and I didn’t bother to go through the exercise of thinking about what I would do to resolve it.
Being a founder, more than anything, changes that equation: I value somebody pointing out a problem a lot less than I thought it was valuable when I was on the other side of it, because the actual exercise of figuring out [the solution] is difficult. Being technical co-founder meant that I had to deal with those [problems] on the technical side.
Say somebody didn’t like the architecture, so they would question it. But you can’t think only about what the better way is to rebuild that architecture. You also have to think about what’s the best way to release it that doesn’t affect our customers adversely or what trade-offs we are willing to make explicitly about that and what features we are going to release later as a result.
Having to go through these trade-offs makes me think that product managers make good founders, partially because they’re forced to make those trade-offs. They’re forced to ultimately propose, “Here is the impact of this change.” Being a founder takes that to a level of fundamental company strategy.
Now, especially as a solo founder at Stork, having to deal with the implications of those decisions is very different because the considerations are very different. Things that looked like very straightforward decisions and simple from the outside — they’re a lot more complicated from the inside.
For better or for worse, being founder or co-founder means that the buck stops with you.
RS: You mentioned you worked as a technical co-founder, and you mentioned how your concerns varied from your non-technical counterpart. Could you talk a little bit more about how do your concerns or worries vary if you were on the non-technical side of things?
VS: It depends on the technical leaders and how they manifest their role. The leaders that I’ve worked under have been fairly holistic engineering leaders, meaning they focused on the people almost as much if not more than they focused on the underlying technology. That’s the philosophy I’ve taken into the role.
I was still able to abstract myself from areas of the business I didn’t enjoy, as long as they weren’t technical. For example, I don’t want to deal with making sure a customer pays their bill on time. I could say, “Look, somebody else is going to deal with that.” I can kind of delegate that.
As a solo founder, you have to actually figure out what are the mechanics and considerations at play when you’re trying to get somebody to pay a bill, or when you’re trying to chase down somebody that was supposed to write something for you. Those tasks have all these smaller muscles and all these supporting muscles that I was able to lean on my co-founder to do.
I thought we had a fairly complementary skillset, and without a co-founder, all of that goes away. I am very grateful for the experience of having been able to tackle half the challenge of founding a business before I tackled the whole experience because I was able to see somebody else handle it.
More than anything, I was able to understand that you don’t have to do these things perfectly. No founder out there is 10/10 in everything. You just need to be okay with being 6/10 on some things, as long as they’re not core to what makes your business successful. Being able to focus on more of the things that were in my strength-zone is something I was able to do as a technical co-founder.
No founder out there is 10/10 in everything. You just need to be okay with being 6/10 on some things, as long as they’re not core to what makes your business successful.
RS: I know that this changes over time as a company grows or as its challenges change, but what are the things that you think about the most as a founder? What occupies the majority of your brain space and your time?
VS: As a founder, in some ways, your high-level goals are pretty well defined. You need the business to survive, so you need some funding; you need some revenue coming in. To do that, you need to make sure the customers are getting value, or you have a path to getting them value. You can convince somebody that that’s the case, and they can fund you. You need to make sure that you have a team that is able to deliver on that value and that the team is going to grow in keeping with your demand or whatever kind of growth targets you have.
How do I make sure that we have the money we need to survive in the next five years to deliver on our vision? How do I make sure that a customer is both understanding our capabilities now and our vision so that they’re interested in working with us — or prospects are interested in working with us?
And I have to make sure that I grow the team, and that’s its own set of challenges. That’s both hiring but also keeping the existing team excited about what they’re working on and sold on the same vision that our customers are sold on.
There are three dimensions that I end up coming back to. How do we get the next cohort of customers? What’s the value proposition that aligns with our vision that I can start delivering or I can start selling folks on? How do we start building the product?
I’ve learned in a real way to start thinking much bigger picture before I think about technical execution.
I’ve learned in a real way to start thinking much bigger picture before I think about technical execution.
RS: For someone who’s considering founding a company: they want to be a founder someday, or they want to be a founder tomorrow — what advice would you give them? What do you think they should know going into it?
VS: Take into account where people are starting and what their strengths are. The most valuable thing you can do for those folks is frame it in the context of “why?” And what they’re good at and what they’re concerned about in starting a company.
For me, I never imagined being a founder so demystifying the act of founding really helped. Realize that you don’t have to go into it knowing what all the responsibilities of being a founder are. You just need to be able to handle them one at a time. You don’t have to see the full picture in order to move forward. Just take it one day at a time.
Also, a lot of advice that people give you I find that is only useful when you’ve run into that same problem, and it’s rare that advice actively preempts something from happening. Advice can help you see that you’ve fallen into a pattern that’s been experienced before. Dealing with all these things as they come up and realizing that I didn’t have to know all the answers upfront has been helpful.
Realize that you don’t have to go into it knowing what all the responsibilities of being a founder are. You just need to be able to handle them one at a time. You don’t have to see the full picture in order to move forward. Just take it one day at a time.
RS: For someone who’s starting their first job in tech and who is interacting with their first founder or set of co-founders, what should that person know about the founder or co-founders? What would help them better understand the founders’ actions and incentives?
VS: I think it’s all about trade-offs. I would emphasize the amount of the trade-offs that founder is making as they’re having [a] conversation with you.
And if there’s a problem, can you go through the full exercise of not just pointing out a problem but also pointing at why you think it’s important, what the priority is, and how you suggest solving it? Because otherwise you’re effectively transferring that responsibility to somebody else, and you’re just creating more mental overload for them. It never resonated until I found myself on the other side of it and realized that I only have so much brain space.
I think understanding what founders are optimizing for is important. One of the most effective pieces of advice I’ve ever received, when speaking to not just senior leaders but also speaking to partners, is to understand what their top three priorities are.
The way that they’re probably organizing their thoughts is that they have some key results or some priorities or some goals. If I don’t have something useful that touches on their top priorities, chances are that they’re going to slot my concerns somewhere at the bottom of the list or not care about my product.
Being able to speak to people in terms of what they’re interested in or what they are spending their time thinking about is incredibly effective, just shockingly effective to a degree that I think I never appreciated.
When talking to a founder, think about the amount of trade-offs that founder is making as they’re having a conversation with you.
RS: As we’ve been talking, I realize that one question that I didn’t ask is “how would you define the job of a founder?” Other than having an idea and starting a business, what does a founder do? What is their job; what are the roles and responsibilities?
VS: In my perspective, it’s making sure that you deliver the best product and experience to your customers. Through the experience you set out to deliver, you’ve solved their problem.
People say that the founder plugs the holes to make sure the company can deliver that experience. I do think that’s true, but it doesn’t always look like that. Typically the founders have strengths, and they will lean on others who have more of a capability that they don’t have. But if you’re in a business where the problem you’re solving for a customer is very technical, and you are not a technical founder, then there’s only so much you can do. Your job now becomes to hire the person who can help.
You’re starting a company because you enjoy the challenge or the journey of solving a problem. You’re excited to work on a particular solution or maybe you come in from the perspective of you just like the journey.
My professional experience with this has been that — if you’d asked me 10 years ago, I would’ve said that it’s not dignified to want to start a company just because you like starting companies. You feel like you have to feel passionate about a specific space. I’ve learned to get a real satisfaction from trying to find a way to make people’s lives better even if they don’t start out knowing what that is.
And in fact, most of the surface-level problems have already been addressed, or there’s a reason they haven’t been addressed, so there’s actually a lot to be said for the journey of not knowing for a few months and trying to figure it out. So, simply, you stumble into the problem you want to solve, into the value you want to deliver, and then your task becomes trying to deliver it efficiently and quickly.
In becoming a founder, you stumble into the problem you want to solve, into the value you want to deliver, and then your task becomes trying to deliver it efficiently and quickly.
