Episode 430 | What to Look For In a Co-Founder

Show Notes

In this episode of Startups For The Rest Of Us, Rob and Mike talk about what to look for in a co-founder. They touch on different aspects of evaluating someone for the role including, honesty/integrity, skill-set vs. future skill-set, fixed mindset vs. growth and more.

Items mentioned in this episode:


Mike: Rob, why was Pavlov’s hair so soft?

Rob: I don’t know, Mike. Why was Pavlov’s hair so soft?

Mike: He conditioned it.

Rob: Damn. Not fair.

Mike: This is Startups For The Rest Of Us Episode 430.

Welcome to Startups For The Rest Of Us, the podcast that helps developers, designers, and entrepreneurs be awesome at building, launching, and growing software products, whether you’ve build your first product or you’re just thinking about it. I’m Mike.

Rob: And I’m Rob.

Mike: And we’re here to share our experiences to help you avoid the same mistakes we’ve made. What’s going on this week, Rob?

Rob: I got so sick Sunday night. It was a stomach flu. My kids all had the prior week and I thought I had dodged it. I was doing all good and then it was one of the worst nights I can remember. I was up five different times during the night. I was delirious, stumbling around. It was nuts. I got up Monday and the kids are off school for a snow day. I was literally on my phone trying to just respond to email. I would write a sentence and then I would fall asleep.

Mike: Oh geez.

Rob: Yeah, it was crazy. I remember as a kid being sick a lot. I don’t know if that’s true or just my memory. Then as an adult, it’s pretty rare that I get sick now and to be that late out. When I get sick now, though, it knocks me out really good. I got a flu shot, I get one every year, all of our kids had flu shots but this year, it knocks through. I lost a bit of productivity and frankly I was dehydrated for two days after. It was crazy.

Mike: That’s rough. I remember getting sick as a kid, too. I think the difference is that you have less responsibilities as a kid. Your responsibility is just lay in bed, stay off the TV, and stuff like that. But it’s so much harder now because you’ve got all the different responsibilities, we each got businesses to run, and then you’ve got your own kids to deal. Hopefully, both parents don’t get sick at the same time.

As early as this week, my oldest got strep throat and then the past couple days, both my wife and I have been on the verge of getting sick. We’re not quite sure but neither one of us has strep throat yet. So, a little germ farm.

Rob: Yeah, that’s tough, How about you? What’s going on?

Mike: Well, I recently got back from Big Snow Tiny Conf. We can talk about that a little bit. The other thing I wanted to point out to other people is the AppSumo giveaway for MicroConf is still going on. That will end on February 11. You have about one week left from the date that this podcast episode goes live, so apply.

You’ll get a free ticket to each to the conferences, both Growth Edition and to Starter Edition, and the expenses for the trip are going to be paid by AppSumo. We’ll link that up in the show notes. You can go over there and get in on the contest. There’s a bunch of different ways you can get even more entries into it. Definitely check out the website.

You can link up your Twitter account or Facebook account, it’s all the MicroConf Twitter account and things like that. Each of those things will add to the number of entries that you get in there and you can get referrals as well. Check it out and hopefully we’ll see you there.

Rob: On my end, I’ve been working on improving this weakness I have. You know how everyone says I’m so bad with names? I don’t remember names, that’s the cliché thing. I’ve always actually struggled with that in a pretty big way. What’s interesting is that it’s not that my memory is bad. I’ve realized this over and over but it was called out to me again.

It was a couple weeks ago at a startup gathering here in Minneapolis. I talked to someone and I’m like, “Hey, I know we’ve met before,” and we’ve started talking, and I was like, “You know? I don’t remember your name name. I apologize but I remember that your startup is named X and I remembered that it launched on this date. I remember that your churn-up until this point was 2% and then I went to 1.8%.” I just rattled all the stuff and their eyes were huge. I was like, “No, this is my superpower.” I remember not just numbers but it’s the context around the concept, like in this case a startup. It all stuck in my head but I didn’t remember their first name.

It’s such an interesting model on how memory works differently in different people because my wife, Sherry, would have remembered the person’s name, their spouse’s name, and their kids names, and none of that locked-in for me. It’s such about relating to people versus relating to some other thing, concepts, or whenever.

So, I’m working on that because no matter how much, it’s an interesting parlor trick to be able to rattle off all the details of someone’s business. We had a conversation six months prior. It’s an interesting parlor trick but it still is not a good thing. I’ve been looking at […] ways to help me remember people’s names and/or to only go to events where there are name tags. I’m just kidding about the last thing.

Mike: Its funny you’ve mentioned that because I’m exactly the same way. I can remember lots of details and pinpoint exactly where we were standing at a particular event when we were talking about it, but I will just have a hard time with a person’s name. Maybe it’s just a matter of focusing on remembering the person’s name and just avoiding overemphasis of remembering all the details of the conversation. Maybe it’s just they stick in my head because those are pieces that are really interesting to me and I know that I can just look down at their name tag and see their name at any time.

Rob: Yes, probably.

Mike: I should have mentioned this a little bit earlier but the other announcement that I have is that MicroConf scholarship applications are going to start opening this week. We’ll open them up today, haven’t decided on exactly how long they will open but I’ll make sure that we put that on the application itself and we’ll link up the application in the show notes. We have a bunch of sponsors who have graciously offered to help fund these scholarships. The scholarships are all for MicroConf Starter Edition. We have at least 20 of them to give away. Last year, I think we had 14 or so and this year we have to least 20. I’m still working on a couple of different sponsors on that, so that number may go up but that’s what we have currently.

Rob: Love it. For me last update, you can back from Big Snow Tiny Conf East, which we’ll chat about in a second. I am heading to Big Snow Tiny Conf West out in Colorado. I think I’ll be there when is episode airs, actually, so this is my inaugural Big Snow Tiny Conf. Looking forward to hanging out with the people. This was your fourth or fifth, is that right?

Mike: Yes, it’s my fifth.

Rob: That’s cool. Any takeaways or thoughts having gone back that many times?

Mike: If it’s raining severely on the second day, just skip it. Just don’t even go out there. We went out on Thursday and it was just pouring. It was above freezing all the way up the mountain, it was raining, and we said, “You know what? We’re here. We’re just going to go skiing anyway.” By the third round were done and we’re just not going to ski anymore.

We’re probably about halfway down and I kind of pushed off to go down the hill. The front of my ski turned like it was supposed to and the back didn’t. Because I pushed off, my arms were basically kind of behind me because I was pushing myself forward. Of course, I just fall flat on my face and rolled down the hill little bit. I did a faceplant right into the slush. Not fun.

I hurt my shoulder a little bit, […] it about a few days later, jar right into the slush and twisted my neck a little bit. But both of those things is nothing major. A few days later I was still sore but at this point, I’m fine. Do you ski at all or do you snowboard?

Rob: I don’t, nope. Here’s the thing. I grew up 90 minutes from Tahoe in California but as kids we are always playing sports pretty intently. I played eight years of soccer and then track for nine years. Played football kind of cross country so we’re always super busy in the winter. Our coaches were like, “Do not go skiing,” because people would tear their knees up, they’d hurt their backs, they did all kinds of stuff, and we didn’t have enough money. We just didn’t have the money for ski gear and the rental and all the stuff. We’re a family of six growing up. I’m the youngest of four kids. People moved out and it just was never a thing even though it was obviously an option geographically. It’s just not something that my family prioritize.

I am going up there. Everyone else go skiing. I’m going to hang out. I’ll probably do a little bit work, I’ll probably do retreat stuff during the day. I have some things I want to get some pretty deep thought, too. I want to do that. I also like drinking hot cocoa and catching up on my reading. I’m looking forward to being up on the mountain hanging out with folks in the afternoons. I guess that’s how it plays out and then having some alone time during the day.

Mike: Yeah. The evening talks are really interesting because you get to hear in-depth details about people’s businesses. Some people come with questions and some people just come with a story. Some people just say, “Hey, this is a problem that I’m working on. Any help with it? What are your thoughts on it?” It’s pretty cool. You get a really good mix of things based on what the people’s businesses are. Some people to B2C, some people do B2B, and it’s just interesting.

Rob: Sounds good. What are we chatting about today?

Mike: Today, we’re going to be talking about what to look for in a co-founder. This came to mind because I’m specifically kind of looking around at my personal network and trying to figure out, is taking a co-founder on for BlueTech a path that I want to go down? If so, what would I be looking for in that type of person? What are the traits or capabilities? What’s their situation? How would that work for me and how will it work for them?

But I thought that it be interesting for the listeners to step back from that a little bit and more of an abstract fashion, think about what sorts of things you should look for in a co-founder and then from there, you can little down the list of potential options and how that would work. Obviously, there’s a little bit of putting the cart before the horse there because you have to decide, “Do I want one?” This is a qualification of, if you do then what would you look for?

Rob: And we recorded an episode about whether you should look for a co-founder, haven’t we?

Mike: I don’t recall. I looked back and I think that we talked about it in general. But I know as we went through and said like, “These are the things that you should actually look,” as opposed to, “Should I get one?”

Rob: There’s going to come a day when we record an episode that’s basically the exact same episode or at least the same topic as what we recorded years ago.

Mike: I know.

Rob: We’ve done that in real life. We’ve gone back and said, “Here are new thoughts on this topic,” but we’re going to do it unintentionally at some point. 430 episodes in, I don’t believe we’ve done that today, but this may be the day.

Mike: Possibly, but we’ll see. I’m sure somebody will remember it.

Rob: Let’s dive in.

Mike: The first one that came up on my list was honesty and integrity. For the person that you’re looking to bring on as a co-founder, what you want to do is be in a position where you know that the other person will always “try” to do the right thing, whatever that happens to be. What that happens to be has to boil down to what your goals in life are and generally how you address different situations or problems. Are they going to have your interest at heart or are they a little bit more selfish? I think you obviously want them to have your interests at heart whenever they’re making different decisions and then balance that against everything else.

You don’t want to sacrifice the entire business, probably, but at the same time there’s going to be certain situations where someone needs to make a decision that may not necessarily be you, and do you trust the other person to make those decisions? What you don’t want is a co-founder that essentially turns into someone you’re micro managing. You really want somebody who is on, equal footing is not quite the right way to put it, but somebody who you can at least respect enough to have a conversation about something, even if you disagree with them on it.

What I found is with contractors, for example, contractors are very loath to bring up stuff that is detrimental to the business or criticize work that you have done. They just don’t tend to give you an objective opinion about things in a way that is any way confrontational because I feel a lot of them are like, “Oh, I don’t want to rock the boat because this is my job at stake.” But at the same time, you need somebody to challenge you in different situations where you could be wrong or they perceive you to be wrong, so that you can talk through those things and say, “Is this the right decision for us and for the business?”

Rob: Yeah. I think this is a big one, being able to have the trust that your co-founder will do two things. One, that they will have your back in a way that, I think you brought up, the kind of the selfish or the self-centered, and I guess honesty and integrity is part of that. But it’s almost like they’re not always going to be thinking about themselves. We all know people who do that and people who don’t come across that way in the first meeting, can later you find out that they just really have an issue. Maybe it’s from childhood or maybe it’s part of the personality, but they really have an issue when talking about money or they have an issue when talking about time. There’s certain triggers that you need to pick up and be aware of because each of us has our own things that sets us off. I feel that’s something that is hard to evaluate in one or two conversations. It really needs to be done over an extended period of time, I think.

Then there is this integrity piece, kind of honesty, ethics, morals that your compasses align. Obviously, there are different ways of viewing the world and you don’t, as you said, want to have to manage this person’s every decision that they make and be like, “Oh, I feel like you kind of screwed that vendor with that decision,” or, “I feel like that was a disingenuous offer you made to that employee,” or, “You certainly didn’t do anything illegal and probably not unethical, but was that really morally the right thing to do?”

Those are hard conversations to have because that’s such a fundamental value that if you don’t share with someone, it’s going to be a constant conflict. Again, not something as super easy to evaluate upfront but it is nice to kind of a must-have, I think, that you do find someone where, in general and 80%-90% of the things, the two of you are going to rely in these hard decisions.

Mike: I think the point that you just brought up about this being something that you may not learn right away and I may take time to get there. I think that’s one of the things that doesn’t bug me but it strikes me as odd when I see people looking around and saying, “Oh, I’m trying to build this business and I want to get a co-founder. Does anyone know where I can find a co-founder?” It almost feels like people are looking for a co-founder in a very, very short period of time. But because of this exact thing that we’re talking about, honesty, integrity, and trust, it takes time to get there.

In some ways you can look at it and say, “Well, are there proxies that I can use for this? Are there people that I know that trust that person?” You trust their experience and then by proxy, trust this new person that you’re looking at as a co-founder. I think that’s a good way to approach it. It’s not perfect but I don’t think that there’s any perfect way to analyze that. It’s not as if you’re cloning yourself and you can’t always know what the other person is thinking.

Rob: Yeah and I think evaluating this in the short term is to know yourself and know how kind of trusting or suspicious you are of new people that you meet. You and I talked about this a little bit but that there’s this test called the Enneagram. It takes about 15 minutes to take. It gives you a number from one to nine. It’s like a Myers-Briggs personality thing. My personality is like creative, introverted, I forget like visionary or something. There’s typically two or three things that are good and two or three things that can be detriments. One of mine is just naturally suspicious of new things and new people.

I know that as a rule, I tend to say I’m a good judge of character. What I actually mean is I really don’t trust people upfront and they tend to have a really good character to get through my defenses early on. I am a very discerning person, which is both good and bad. Sometimes, it’s to my detriment and I write people off too soon. I know that about myself and I will be having internal kind of self-talk or conversations about, are they really coming off the way that I think they are or is that just in my head?

I have known people, my relatives and friends who are on the opposite side. They are too trusting, they get in friendships really quickly, and get pretty deep with people who, it’s pretty obvious that person is not going to be a good friend. That person is going to treat them poorly. Maybe this co-founder relationship is a romantic relationship or maybe it’s a friendship. It is hard for me to watch that because it might end poorly and frequently it does. Those people, I think, are too far on the other side of the spectrum. They are not suspicious enough. I think it’s knowing where you lie and just trying to do your best, frankly, to figure out what you think of someone after few meetings.

Mike: The next trait that I kind of came up with was more or less a current skill set versus ability to learn new skills. You’ve talk about this in the past that comes from like a fixed mindset versus a growth mindset. I look at it in terms of what does somebody bring to the table now versus what could they learn in the future to bring to the table later.

I think that there’s the short-term aspect and then the long-term aspect. The short-term aspect, you’re really looking for somebody who can complement your current skill set. In the long-term, you’re looking for somebody you know what it is that they want to do and it’s not necessarily or directly overlapping with the things that you want to do long-term, because you probably don’t want to have two people who both want to do sales, for example. Long-term, you probably don’t want both to be doing sales. You probably need somebody to be doing technical stuff and the person to be doing more of the business, marketing, and the sales side of things. But if you both want to be doing development long-term, that may not necessarily be a great fit because then, who’s going to be doing the sales and marketing stuff long-term?

Rob: Yeah. This is a mistake I made in the early days. I think a lot of people make this mistake when hiring and finding a co-founder is similar. It’s not the same but it’s similar to evaluating a potential hire. The thing is not to look at their skill set because things are going to change. In startup, they just change so fast.

If I were to look back at myself 10 years ago, I didn’t know 80% of what I know now. You could have looked at me and said, “Wow, this person knows how to write, and he knows SEO, and he knows how to write code. That’s an interesting skill set. What is his potential someday?” You know what? I don’t do much SEO anymore and I don’t write any code anymore. I write a lot less that I used to, actually. Everything that made me who I was 10 years ago, really has have to adapt. I’ve had to learn to build relationships better. Even just speak in public which was something that terrified me early on, and to speak on the microphone which is something that terrified me early on, all the things that you just have to get over.

I have watched other people do the same thing. You look at Derrick Reimer, my co-founder with Drip, you look at Ben Orenstein and you see how they’ve adjusted and adapted over time. And you know when you look at people who are really sharp and who are getting […] done, something you’ll notice about them is they don’t stand still for long. They don’t have the same skill set for very long. They are constantly adapting to new things.

If I’m hiring a team member, if I’m looking for a co-founder, if I’m evaluating a startup founder as I’ve been doing for the past several years but more intensely over the past 11 days since TinySeed applications have been open, a lot of this is not what do you know. It’s what can you learn, how quickly, and it’s trying to be able to evaluate how they can do that. So my question to you is, how can you evaluate that?

Mike: I think if you look at the history of what people have done, whether it’s launching small apps or working for different businesses, I feel like if you’re looking at somebody’s experience and they’ve done consulting at a bunch of different companies, that right there says that they have the ability to adapt, change, work in different environments, and presumably be productive. Otherwise you’re probably not going to get a lot of consulting gigs that way.

I have mixed feelings on somebody who’s doing consulting work for the same business for like five years or ten years or something like that. I would question how much adaptation there is there because you’re not adapting to different business environments and changing conditions. Going from one company or customer to another, it’s a very, very different experience between those two and there’s a lot of different things you have to manage. Whereas, if you stay in the same company or within that, the sandbox there, it’s not going to change a lot or dramatically.

I think in those cases, it’s a little less clear cut as to how to measure that. But I would definitely say, if somebody’s hopped around a little bit, then you can give them the benefit of a doubt in terms of their ability to learn new skills. The thing you have to be a little careful of though is, is it like entrepreneurial ADD where they just can’t focus on something and that’s why they switch so often? I think that many people suffer, I myself included, suffer from the shiny object syndrome where you hop from one project with other because something interest you and you’re not necessarily finishing things. That’s something that kind of comes into this. That’s something you have to balance that against.

Rob: I agree. That’s what you have to dig into. You touched on it exactly is was the person running away from something? Like, “Oh, this got too hard,” or, “Oh, that boss was dumb,” or, “They didn’t value me there,” or, “Oh, I got bored of that.” Or is it ambition? Ambition is not the right word because it’s this weird thing. I’m not that ambitious but I love creating new things. But I also finish what I started. I think that’s something to look at when your evaluating.

I agree that hopping from one thing to the next can actually be a good and a bad trait and it’s determining what their reasoning, logic, and motivations for doing that are, then I agree. If someone’s been working the same job or the same contract for years on end, it can be hard to gauge. You almost have to like, “I don’t know what else I would look at to figure out.” It just makes it harder to evaluate if someone hasn’t been tackling new challenges. I think that that’s kind of the thing that I’d be looking for.

I think the four axis that I look for when I think about someone as a startup founder, like skill set, I think of technology skill set, like are they developer or do they speak developer? Marketing, can I actually get stuff done, drive traffic, optimize a funnel, convert people, trial to paid? SaaS experience which is pretty unique. Most people don’t have it but do they know all the metrics and the numbers that churn the LTVs? Do they think in terms of SaaS numbers? This is one thing you can certainly learn but if someone already has that experience, whether they worked in-depth for one or whether they start at one. The fourth is kind of hiring, managing, and delegating of people.

There are certainly more more axis but those are honestly the four that, when I’m evaluating a startup founder, do I think they’re going to succeed? I look along those axis and they don’t need all four of them. Again, if they can learn stuff, you can start with one of them and branch off into the other three. But if you have two co-founders, I really don’t want two co-founders who both have a ton of tech experience and both want to write code. You want one of them who’s willing to know the marketing or to learn the marketing. Or one who’s willing to do the hiring and managing because assuming that you are going to scale up at least a little bit, you need to learn all these skill sets.

Mike: And that kind of leads directly into the next one which is difficult to measure resources. There’s certain types of resources like time and money which I think are directly measurable. But when you come into things like your personal network or your experience and your skill set, I feel like those are a little bit more difficult to measure in terms of what it brings to the table and what it means for the future. I think every situation is different. Those things are going to mean different things for different businesses.

Let’s say somebody brings a lot of domain knowledge and expertise to a particular problem that you’re working on and you want to involve them. The stuff that they know and that they have experience is going to be valuable. Is it stuff that you could learn on your own? Yes. The other side of that is perhaps and perhaps not. You have to take those things into account some way because they do make that relationship a little bit more valuable.

It also depends a lot on how long it’s going to take you to acquire that knowledge, like have they already tried to do a startup in that space and they either succeeded or failed? Those things can make a huge difference in terms of whether or not want to add that your team.

Rob: And then there are the measurable resources that each co-founder might bring. How much time does a person have? Obviously, a lot of us start by our products by working on them part time. What I’ve found in my experience is that people have a lot less time on the side than they think they do. A lot of times I have hired contractors—this probably happened six or seven times to me—where I’ve gone through a full interview process, done video interviews with 6-7 people, narrow, narrow, narrow, get somebody it’s like, “You’re sharp. Cool. You have a day job as a marketer and you want to run Facebook ads for me on the side. Love it. How many hours a week? Okay, you’ve got 15 hours, 20 hours. That’s great.” Then we’ll start and they’ll work four or five in a week. I’m going to, “Hey, what happened?” “Yeah, I just have a lot less time that I thought I did.”

This is something that I think you really need to dig into. If someone tells you they have 20 hours a week to work, I honestly think you should try to get a schedule and say, “Carve that time out because if you have kids, you probably put them to bed at seven or eight or whatever. So you’re working three hours a night during the week and then some on the weekend. If you don’t have kids, what does that look like?” Again, everybody seems to overestimate the amount of time that they have. I think it’s kind of human nature.

The other thing to think about in terms of a measurable resource is money. Does having some money help you get to escape velocity quicker? How much money does each person have to contribute? If you have an even amount, then cool. You can be 50/50 partners. If one person has more, that probably should buy them more equity, I think, unless time is out of whack. There is a bunch of things to think about but certainly someone bringing money to the table can be a bonus. I would say with caution, money is a very short-term thing.

In the early days of a startup you can think, “Oh my gosh. This person is bringing $20,000 to the table but they don’t have much time so they should get this huge chunk of it.” That makes sense for about six months. It makes sense until you get to the point where you launch and suddenly you start growing and $20,000 just isn’t that much money anymore. There’s the balance here because money in the early days is more risky. It is a big deal for someone to bring $20,000, $30,000, $40,000 into a startup that may never work. I would say consider all of these other factors. I would probably put above the value of just pure dollars invested.

Mike: Yeah. I think time and money tied together to some extent as well because if somebody has money set aside and the business isn’t quite making enough to pay the founders of reasonable income, can somebody extend the runway to some extent by living off of less? You may be able to command a salary $150,000 a year but do you have to? If the business can’t support that, then obviously you can’t pay yourselves that. How is that going to work? Is somebody essentially taking a massive pay cut in order to be able to contribute time? Do they have other sources of income?

That’s kind of really what I was getting at in terms of the measurable resources. Not so much can they dump a bunch of money on it but are they able to be somewhat self-sustaining and still contribute to the business while it’s getting further along? Nights and weekend project is a very different story. I think you brought up a lot of great examples and points about the fact that people have probably a lot less time available to them than they think they do. Some of that comes into motivation and as you commented earlier, whether they’re running towards something or away from something.

Rob: I think another big thing to think about is, talking about long-term goals a big deal because startup had a lot of connotations. Startup may mean you just want to start a really nice lifestyle business. It’s going to get you collectively $200,000-$300,000 that you guys split and that’s a good goal to have as long as you both agree on it. But if one person wants to raise venture funding or they want to go seven or eight figures and stay bootstrap, these are all different paths and it’s going to impact a lot of things along the way.

This is something that I would at least have a conversation. You may not need 100% everything ironed-out upfront, but to say, “What really is your goal here? Is your goal to work as little as possible and for both of us to make six figures? Okay, let me think if that’s what I want to do.” If you don’t, there’s going to be this constant tension as you’re growing your product.

Mike: And sometimes, these things don’t always work out and you may think upfront that your goals overlap. Those goals may change over time. I read an article from the guys over at Buffer where there’s three co-founders and initially, everybody was kind of on the same page. They all wanted to do the same things. Over the past couple years—I forget the exact timeline of that—they ended up kind of going in different ways. Two of the co-founders left the company and there’s one still there that’s running everything.

It was interesting to see that they laid out the different types of conversations they had and how it took a long time for them to get there. There are ways out of the situation if long-term you find out that your goals have diverged. But I think it’s important to keep in mind that if you have that conversation early and they don’t overlap right then, it’s possible they could kind of come in alignment but it’s probably not a good place to be starting from.

I think one of the last important things that you should be looking in a co-founder is, do they work well with others? Specifically, by others I mean you. But in general, are they easy to work with? Are they, not necessarily focused and driven, but can you hold a conversation with them and not get angry with them about how they’re doing things? Or vice-versa. Are they going to critique your work all the time and if so, is that something you can deal with?

There’s only so many ways that you can figure this stuff out. I think probably the best way to do it is just work together for a little while. I think you’ll very quickly see whether or not you’re going to be able to work with them long-term or not. There’s soon going to be some things that jump out of you very quickly and then some things that you’re going to learn six months, two years down the road that you didn’t necessarily pick up on right away.

It’s not necessarily good or bad but I think that hammering out what those things are that really irk you or the things that you do that irk them, if you know those upfront you can at least have the conversations and talk about it, and figure out whether it’s something that you can both live with or not. If you don’t do that then you could head for trouble.

I haven’t found any other good ways of doing that other than actually working with somebody. You can ask friends or colleagues or people who have worked both with you and that other person but sometimes those recommendations are: (1) hard to come by, and (2) people don’t really want to throw other people under the bus. It’s difficult to get that information from a third party.

Rob: That’s right and when I’ve done these reference checks, I tend to say, “Tell me about the hardest part about them. Tell me their biggest weakness. Tell me where did their plans […] are like.” I try to dig into this stuff. I try to just prove my theory that they are someone that I should work with. Or even not even just prove it but just to know. I can work with blind spots as long as I know what they are, like this person tends to give a very direct feedback, so be prepared for blunt feedback. It’s like, “Okay, that’s not a deal-breaker for me,” but when this person says something that shocks or offends me, it just be like, “Cool. That how they roll.” That’s also a big plus for a number of other other reasons.

I think a good story of this is like Jordan Gal with Ben Fisher and the founding of CartHook. They say they dated as founders and they really tried it out for quite a while. A couple months, I believe. They went and co-worked in one location and then another because they lived across country from each other. But they really got to know each other. I’ll even say with Einar Vollset and I, co-founders of TinySeed. I asked some folks who knew him better than I did. I know him through MicroConf but he and I never worked together. I asked a few folks, “Hey, you know him better than I do. Tell me about him.”

Then we started just working on a deck and that’s all it was. He said, “I don’t know. What you think? Should we do a deck?” “Cool.” Then I get to see not very much skin in the game. He and I are both saying, “Well, we’re not sure we’re going to do this.” I knew we’re going to do it but it was both of us kind of sizing each other up and saying, “Is this person going to be fun and complement my skills and are they going to work well with others?”

That was the big thing to just sit and hammer something out, to agree on certain things, disagree on other things, be convinced by the other person because you’re like, “Wow, this guy’s smart.” That’s the thing that I think you want to get to. So, even doing one or two smaller projects together before you do a full commit, I think can really be helpful.

Mike: In the beginning of this episode, you and I have chatted briefly about whether or not we’ve actually covered this particular topic before. I went back and looked in episode 408, evaluating whether or not you should take on a co-founder. That’s where we talked about that. This is more about what to look for in a co-founder.

Rob: And that was only 22 episodes ago and we had already forgotten? That is like six months.

Mike: We we were pretty sure. We knew we’ve talked something about it. We just didn’t remember the specifics.

Rob: I total did. It was vaguely. I knew we’ve talked about co-founders a number times. I just don’t know what the specific episodes have been.

Mike: That’s okay. We’ll let it go this time.

Rob: All right. If you feel like you’d like to add something to this list of what to look for in a co-founder, including how to evaluate that, you can either post at Startups For The Rest Of Us episode 430. You can post a comment there, or you can email us at questions@startupsfortherestofus.com, or call into our voicemail number and 888-801-9690. Our theme music is an excerpt from We’re Outta Control by MoOt. It’s used under creative commons. Subscribe to us on iTunes by searching for startups and visit startupsfortherestofus.com for a full transcript of each episode. Thanks for listening and we’ll see you next time.

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