Episode Introduction

How do you go from maker to manager and create the building blocks of company culture? These questions were at the forefront of Adii and Ben’s recent conversation. Progress on Cogsy and 1-Click Pony has reached an exciting juncture, with marketing websites now live for both companies. Adii touched on his method for delegating to trusted team members, while Ben discussed the necessary value of honing young talent and attracting them with startup allure. Both Ben and Adii agreed that keeping your team on the same page in order to meet major milestones is a must.

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Show Notes

Key Takeaways

0:54 - Shifting from maker to manager

Ben describes the challenges that arise from going from the role of solo maker to the manager of a team in pursuit of a larger vision.

“I have shifted over my professional career from doing all the work myself as programmer and designer, and basically looking at other people, looking at teams and being like how are they not going faster? I think there's a lot of unsaid planning that happens when you're doing all the work yourself. Like I can more or less judge how long something will take. I can reprioritize in my head. And I think in general, and especially earlier on in my career, people would look at the products and be like, Oh, that's dope. That's great. It's interesting going from a maker to - I hate saying manager - but I have intentionally over the last seven years tried to extract myself from doing the work. In part because I figured that is the transition that most of us go through to be more effective and to do bigger and greater things. And there's much better great talent now. But I find it very difficult, I know a lot of people do, to get things shipped on a we'll call it predictable cadence.”

2:22 - Staying on the same page

Ben wants to walk the fine line of keeping his team productive from afar and being a more hands-on shepherd and engineer.

“As the business owner or as we'll call it the leader, I need to have a general idea of what's being worked on. How long is this gonna take? What roadblocks or decisions are you making along the way? And especially as a senior engineer, I also want to be involved in some of the planning process. I think there've been several moments in the last like six months where we've looked around and like, okay, this isn't going fast enough. I don't understand what is being worked on. And I'm trying to find that balance. And I keep trying to basically bring everyone back and be like, okay guys, we need to all be on the same page so that we don't have to think. So I don't have to be wondering what are people working on. I have not yet found an effective way to do that.”

4:13 -  Technical versus non-technical founders

Adii calls BS on differentiating between a “technical” and non -technical founder in the modern age. Instead, he says the importance lies in translating concepts for founders who aren’t programmers.

“I think this whole thing about what constitutes a technical founder versus a non-technical founder these days is like - there's bullshit there, right? I think most roles within a technology company these days are technical. Some are just programming and some aren't. So that aside, but those founders that struggle with this are generally the founders that don't program themselves, right. So they need almost that kind of translation of ‘here's the code we're committing to the code base. And here's what this actually means. And when we say we're making progress, here's what that means relative to these other metrics,’ that the founder or the leader is tracking that they do understand that is in their wheelhouse, i.e. we want like dates, right? Like i.e. we want to ship this feature, hold marketing release on this date - that's something I can track. Or like we ship this new kind of feature and it reduces support by 10%. That's a metric that I can track.”

5:37 - Don’t change deadlines, change scope

One of Ben’s cardinal rules is that he changes the scope versus deliverable dates. Right now, the product roadmap is fuzzy as he tests different hypotheses for 1-Click Pony.

“I’d say there's very few rules that I live by, or tenets that I live by that I’ve actually - you say it out loud and I’ll say one which is we don't change deadlines, we change the scope. So one of the most important things that I have learned and that I reinforce on any project is we decide on a date. And if we get to a point where it looks like we're not going to hit, don't change the date, we change the scope...part of the challenge is I can't look far enough right now to be able to say here's what our product roadmap really looks like. I am still at that point where it's like, we have hypotheses around what's going on. My number one priority right now is finding more qualified customers and testing the sort of we'll call it different like value proposition levers.”

8:38 - Trusting your team

Adii subscribes to a philosophy of delegating to trusted managers. When business size doesn’t allow for that, he tries to rally the team around shared goals.

“I generally am able to wear all of those kind of functional hats within a business and to the sense that I can understand what happens in every kind of new part of the business, right? Everything from engineering, product, sales, marketing success, operations, finances if you want to add that. So I also mostly only play in that upper end and then decide where I need to do a deeper dive...What was helpful is having leaders in place, firstly, by people that I can trust. So that I don't necessarily have to speak to five different people to get an answer, right, or to get the full answer. I can speak to a single person. I think that's helpful. But generally, like I get it, like you're a team of three. You're not going to impose that single manager at this stage, the unit economics doesn't make sense. But what was helpful is, what we used to do is we would essentially rally around a few kind of key goals. And then based on that decide, hey, these are the things everyone needs to do to meet those things. And then I would probably check in on, like, we did weekly meetings with Conversio, for example, where we at least sync up about those things. But I think in the early days, it's okay to probably do that biweekly or even monthly.”

11:06 - Peer-to-peer accountability

Adii enjoys fostering peer accountability to further cement shared goals and to diffuse top-down management responsibilities.

“I think the approach there is to get everyone's buy-in on what we're hoping to achieve as a team, right? Making sure every individual knows what they need to contribute. And then there is that peer-to-peer accountability, which is like, if I don't do this, then I'm letting my mate next to me down. Because they're going to do their work, and if I don't do my work, we're not going to meet or reach these goals that we set ourselves. So peer-to-peer accountability, instead of like everyone having to report into a manager or a leader, right, peer-to-peer. I think that's the first part. And then giving that person ownership. Say, listen, if you're clear about what you need to do here, the responsibility is now back on you to say, Hey Adii, I have a stumbling block. Hey Adii, I don't have this thing that I need, right. And then change that. Because again, that shifts part of that responsibility of management bottom-up versus top-down.”

15:14 - Culture as collaboration

Adii added that the best company culture is a collaborative one. Getting team buy-in can and should be a genuine endeavor.

“What happens over time is I think if you put as founder, and as leader, if you put that first role that MVP out there, then you start the iteration process. And crucially, I think if you hire people that fit or where there is those shared values and interests about what we're working on and how we're working in that, then it can actually become a collaboration in terms of, hey guys, like we need to, for example find a way that - you don't even have to be narrow. Like I would say you could say, we need a way to sync on a weekly basis. Like, shall we do a meeting? Is there another way for us to say, okay, we're going to do a quick meeting. How long should a meeting be? What should we cover in that meeting? And those things can be I think collaborative...I don't think it tries to make any sense for any founder to adopt any kind of best practice for any part of their resonance. If it doesn't resonate with you, like if it doesn't energize you as a leader, right, then it’s not going to work in the long term. So I think that's why you should have the loudest voice initially, and then you slowly start paring that back as the team takes greater kind of ownership and as they develop a shared vocabulary about what this means for our culture, for the things that we agree on for the way we work.”

17:31 - Embracing short-term thinking

While Adii has a long-term vision, he’s setting that aside to focus on pared down V1 needs.

“So with Conversio, or Receiptful initially, there wasn't I think even medium-term vision for the product. Like we were trying to solve a single thing. With Cogsy, I had a different challenge, which is I first imagined this whole massive thing in my head. And then initially the biggest challenges were how do I pare this down? Because I can tell a very nice story to anyone about what kind of this 7-10 year journey looks like. But I couldn't tell a story about what does V1 do for a merchant. So I had to pare that down to just a single thing. So now for the first version I could probably see like a few things that if we released V1 tomorrow, we could stay busy with just things that I have in my head, or we've discussed with the team, for about three months. And then I also have this bigger vision that needs to be defined as features, not just ideas...But it's not something that I'm worried about. It's not something that I check back in consistently. Right now it is very short-term focused.”

21:32 -  On implicit trust in your hires

Adii likes to hire experienced people to help steer the business. At some point, you have to just trust in people to communicate and work at a professional level.

“And I think same way though that I think about hiring this head of growth, right. An incredible individual, they've got pedigree working for other companies. We spent an hour and a half on the call and a few emails back and forth. But again, like there is that assumed trust at least. Obviously that trust needs to be proven and we need to work together. But at least in that regard, like the hope there is they also come in and they lead things. And again, like I assume trust until I realize that hey, this is not gonna work. In reality, if this individual comes in and makes things work out and we can't figure out how I can trust them to flip that, how I manage kind of role, i.e.  they need to manage me more than I need to manage them kind of thing, then that probably is not the best fit in the long-term. It's not a reason to get rid of such a person, but it's probably not a great fit at least in the long term. So I think that trust is important. I think to that point, I trust myself right? And this sounds totally weird, but when I commit to doing something for people, I trust myself to do that. Or at least constantly communicate and say, hey, Ben, like, I'm stuck here. I need help. Or, hey, this came up, I made another plan, but unfortunately this changes X, Y, Z, right? That's what high-functioning people manage to do.”

23:18 - On honing the diamond in the rough

Ben agrees that seasoned staff are valuable. But when budget won’t allow for that, he tries to identify and help hone young talent.

“I think especially as someone who was the maker, when I first looked at hiring, maybe you can even say now, I often looked for younger talent who I thought part of the appeal was like to mentor them and basically looking for the diamond in the rough. Oftentimes we didn't have budget. Like the same thing happened at CartHook. What's interesting is what you just described is the same way if I were to summarize how a good friend of mine from college, Brian, he founded TodayTix. Raised a bunch of VC money, they are now a huge goliath in the theater tickets business, online tickets. He was a Broadway actor, but he also worked at a private equity firm. And his first thing was he hired senior-level people in all the different functions. And then it was up to them to hire below them. Which is like the opposite of how I approached it. And I think having gone through this process a few times of transitioning from the maker to more of a manager, it makes like what you just described - it makes a lot of sense of why that would be a better, healthier way. On the flip side is, that's expensive. And how could you go about hiring someone who's a young talent who like basically what you're selling them is a growth opportunity as well as money.”

28:04 - A clear value proposition

Adii is happy with the progress made over the past week, citing a clear, one-line value prop as the clearest sign of advancement.

“I've just been working very closely with our biggest customer. And I think the thing that excites me is as the things on our side are taking shape, getting literally that giddy kind of reaction from this customer like yes, yes! Getting that, that is showing a lot of promise. And yes, there are a few assumptions there still, right? We can't build something for a single customer. We still need to prove that the product and the messaging and all those things resonate. But I think from a product perspective, I think from the first new kind of show that we recorded a couple of weeks ago, we've made immense progress...we've really narrowed down the value prop for Cogsy to a single thing, right. Which is: we will help you make smarter purchasing decisions. And what that actually means is we do a lot of things, magic, magic, magic, magic. And then we just say, here's the kind of the best purchase order that you should send right now to any one of your suppliers or vendors.”