Video Transcript

00:12 Scott Gerber: You obviously went into business with a very close friend that you've met and reconnected with. Why did you feel it was a good decision to go into business with someone that you knew ahead of time, and ultimately, what were the discussions that you had to have at the up front, say, "This is... We're putting our friendship on the line here to do this." What are some of those conversations and what kind of conversations should they have before they decide to partner?

00:34 Alexis Maybank: Well, listen, not all friends should go into business together, not all family members, and not all people, obviously. So, I had come off and start up right before Gilt that didn't work out, and it was purely a failure of partnership. Great idea, but that's the most common grounding force for good ideas.

00:52 Gerber: What would some examples be of why that partnership failed?

00:55 Maybank: Well that's... It's a great question 'cause it led to many of the conversations Alexandra and I had about why we should or shouldn't work together. But at the base, some of the things that happened that can tear apart partnerships are trust. Do you have that trust? Is there any red flag around it that says, "Maybe we have different values, or maybe we want different things for our business." If your goals aren't entirely aligned for the type of business you want to build, a really big one, a small one that you're on top of. If you... Your goals aren't aligned in terms of how you wanna do business, the operating principles you wanna instill, then it's gonna create tensions that could potentially ground the business to a halt.

01:35 Maybank: In the case of my second startup, I ran into many of those things. We viewed very differently how you set up the office culture and environment, how often you're even in the office, what you want out of the business. Do we want to be king no matter what? Do we wanna build a big business no matter what? And that was really a critical thing that I overlooked. So going into business with Alexandra, what I wanted to make sure is that we had the really hard conversations of what we both wanted for this business, the environment we wanted to build, create, and importantly how we'd handle conflict.

02:07 Maybank: No matter what, you're gonna have conflict in a business environment, but what's most important is how you fight. And in our case we wanna be able to fight well, but not in a disruptive fashion where people thought, "God this is uncomfortable." So we had to figure out how we were gonna handle that, and we decided ultimately okay we're gonna have to disagree on things, but we're gonna go into a room, we'll chat, we'll reach a decision, and we'll agree to disagree and just move forward and not revisit it. Here's how we'll communicate, here's how we'll make sure that our business working relationship doesn't overtake our friendship. Because that can happen a lot too, where your personal friendship goes out the door and all you do is talk about work. So there are a number of things that you have to talk about and make sure that you have almost that pre-marital counseling before you get in the marriage. If you see any of those red flags pop up or that concern of, "Oh, maybe we're not on the same page", address it as soon as possible, not even a day later, because it will crop up and grow and grow bigger over time.

03:06 Gerber: When you decided to partner, where did you see each of your strengths and each of your weaknesses that could be helped by your strengths?

03:13 Maybank: Our skill sets are entirely different, and that's helpful. She has a background in merchandising and sales. I have a background in digital marketing and product user experience. E-Commerce, as a whole, is the only industry I've ever worked in, but I think that is where people begin and stop usually. I actually think it's more critical to see how your personalities differ, because those who are very, very similar going into business together, they're always constantly agreeing and maybe running down the same path. For me and Alexandra, I tend to be a lot more focused on what's gonna happen a year or two down the line. I'm terrible at details. Sometimes I don't think everything through. I'm always about five or ten minutes late, she's always five or 10 minutes early, she loves focusing on lists and execution. So we looked, and I'm giving very short piffy examples of how we're different, but I think you really have to look at your personalities too, as founders, and think how complimentary are we. And are we different enough, that perhaps we're getting to a much better place, better decisions. We're balancing each other's blind spots in a way that are really necessary for success.

04:19 Gerber: How in-depth should the initial partnership agreement be? I mean I've heard everything from folks saying, frankly, in my opinion, stupid thing of write it on a napkin, "We trust each other, let's go into business", and I've heard people writing 100-page documents with every possible scenario. Where do you fit in the mix and how in-depth, for that first startup, should you be thinking future-based, thinking the here and now, what should be included?

04:40 Maybank: Listen, you wanna get all the paperwork done. And that's great, get it done for six months if you can. But no paperwork, no matter how well thought out it is, will ever pave the ground for a great partnership. It just won't. So what's much more critical is figuring out how you're gonna work together, how you're gonna fight, who's gonna lead, who's gonna make decisions, how you're gonna disagree. And if you can't get that stuff figured out, if you can't figure out the operating environment you wanna create and what you want for your business, it doesn't matter how good the agreement is, the partnership will never work.