How YOU Can Build a Ride or Die Team: AppSumo Exclusive Edition | EP 5.2

Eric Siu interviews AppSumo leadership about building a loyal team. They discuss hiring for culture fit, weekly rituals like Monday meetings and ROI stack-ranking, and how bootstrapping shaped their approach to company culture and team offsites.
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Hey everyone, today we have Ayman Ababdulla, who is the president of AppSumo, which I've been using for years and years. We talked about processes earlier, but so we got process, goals, and now I wanna talk about culture too. And I think there's a big story around the culture of AppSumo. I mean, you guys, there's tacos, there's a Sumo, all this kind of stuff. So what do you guys do from a cultural perspective? What are some stories you can share that are, you know, pretty amazing?
Yeah, so I mean, for us, like, we're only at 9 employees right now. Culture, I think, All too often, like, CEOs are thinking about, like, what is the culture of the business? How can we improve culture? I know we'll have happy hours and we're going to do trips and we're going to do all these things. And they think, like, by saying those things that that's going to impose the culture. Ultimate culture is just simply who you hire, right? And so for us, when we're going through the hiring process, we are looking for people that are like us. We want people that are super humble, that work hard, that are super smart, that simply have a results-oriented attitude. that are very team-oriented. They don't have, that's not my job, in their vocabulary, that don't believe in a 9-to-5 work set. They don't mind coming in at 10, 11, but they also don't mind working 10, 11 at night, right?
Mm-hmm.
And so the very first thing from a culture perspective is hiring the right people. If you try to shoehorn a square peg into a circle hole, they're just not gonna be a good fit for the team. And so before we hire anybody, we make sure we go to lunch with them. We make sure to bring them in for a day. Some of them are working 2, 3 weeks with us before we finally pull the trigger. That's number one. Number 2 is also, you know, acting like the culture, right? So like, you know, we got a text last night, 10 o'clock at night, like, hey, is the site down? 2 or 3 people immediately jumped on Slack, double-checked everything. Everything was fine. Site was running a little slow and we got it back ramped up. And so just constantly working towards that culture. And then the last thing is like recognizing that everybody has a goal and like being able to work together towards that goal, I think is super important for that team embodiment.
Got it, makes sense. How about in terms of team activities? What do you guys— you mentioned, you know, outings and things like that. What do you guys do?
So just 2, 3 months ago, we did a half-yearly trip. We do 2 trips a year to Seattle, and this is a great time for us to just sort of kick back.
Why Seattle?
So it's the middle of Austin and it's 100 degrees. It's a great time to get to Seattle. For those that don't know, Seattle is like the best-kept secret in America in the summer, right? It's like 70 degrees and sunny for 100 days straight. There's like sailboats everywhere. We went out there and we ended up renting 2 Airbnbs, one in the woods. We spent a couple days there just hiking and doing some bonfires, enjoying ourselves. And then we did another 3 days in the actual city where we went out and just partied together. And when you're spending that much time together, that's really when you get to know someone. You can be working and it's all about work, but once you get out of the office and you're having more personal conversations, you're able to bring that unity back into the office. So we'll make sure to do another one in December.
Got it. I think these team outings are really important. What typically goes into itinerary? You know, what kind of budget goes into these kinds of things? I mean, can you shed any insight to those?
So, you know, we're lucky enough that we're— the business is doing pretty successful, and so we're able to like afford something that's a little bit more fun where we are able to fly out of town and do all these things. But even for like someone that's just budget bootstrapped, it's like, hey, let's just spend a weekend at an Airbnb maybe an hour away from town. And, you know, we're gonna cook the meals in-house. We're gonna spend some time maybe just game planning the rest of the year. I think I'm a big fan of T3s and B3s, which is your top 3 things that happened last year, the bottom 3 things that happened last year. So we do T3s and B3s where we analyze, hey, like, what's working really well? And perfect example, like, for us, like, lifetime software deals have been selling very well on AppSumo. And so we just decided to double down on that. And that has resulted in a huge increase in revenue.
Good to know.
And then some bottom 3 things that, you know, just simply weren't working, decided to cut off the plate. Spend a little bit of time there, spend a little bit of time interviewing each other, right? Asking more personal questions, like asking about, you know, how they grew up, where did they go to school, and asking about their parents, like being able to learn, just becoming friends, right?
Mm-hmm.
And then obviously scheduling a lot of time for just fun activities. We did hikes, we went out to some clubs, we went out to some nice dinners. So being able to just do things together where you can have like that shared collective experience, I think is super critical to building that culture.
AppSumo is the thing that funded Sumo. So you have 2 businesses now. I mean, do you guys hang out with each other? When you guys do these offsites, is it together or?
Yeah, so the actual businesses themselves, they— we don't do the actual events together anymore, but we do happy hours together all the time, we do events together all the time. They're coming out to SumoCon to help out. So there is like, you know, it's great in that, you know, the businesses are operating independently, but there's also a lot of shared resources.
Got it. And you guys haven't raised any money, neither company has, right?
Correct, yeah, fully bootstrapped.
So what's your take on that?
So, you know, I do think that raising money has its time and place. I think the problem when you raise money is that you end up changing the trajectory or changing like the actual goal, and you're thinking about when is the next time we need to raise money versus for us, like, we needed to hit profitability on day one, otherwise we couldn't pay people salary. And so I think like the focus for a bootstrap company is always on the customer, whereas like the focus for an investment-backed company, at least in the beginning, is on the investor as the customer, because they're the only one really giving you money. And so I think the second you can make that transition back to the customer is really when the business is going to start benefiting.
Right, and you're building something real.
Yeah, exactly.
Got it.
Exactly.
Cool. So from a personal perspective for you, what are your daily habits? What are the things that make you kind of who you are?
So I'm a huge geek when it comes to that. I'm constantly analyzing, I'm measuring everything, and just trying to figure out what's the best way for me to be a better asset to this company and a better asset to myself. So a couple things that have worked really well for me is having a really good management system for my email, my inbox, my Slack, knowing what tasks need to come on plate. I've got a huge to-do list that actually has over 3,000 items on it. And then Sunday night, I completely ignore that list.
Mm-hmm.
Usually that list is like, hey, like, make sure to cancel this monthly recurring charge and like make sure to unsubscribe from this newsletter. And it's like all these like small things that just don't have an impact on the business. So Sunday night I go in full airplane mode and I just have a Moleskine and I just write down what are the 3 things that I need to nail down this month that is gonna help us reach our goal for the end of the year. And so when I wake up Monday morning, I'm looking at my 3 things and I'm making sure that that's getting blocked off in my calendar. Because the problem is, if you don't do that, you end up just answering the latest email, responding to the latest Slack message, getting sucked into a couple meetings. But if you know you need to do these 3 things this week, they're usually pretty big things, then you make sure that you're pushing back meeting invites, you're pushing back on things that just aren't a priority, because those aren't things that are going to help move the business forward. That's to me like one of the most critical things. The other thing that I make sure to do is we're constantly looking and analyzing what is the highest ROI items that the business can do to move forward. So every 3 months, every quarter, we do a stack ranking where we list out all of the ideas for the business. We measure them by impact and how long it's going to take, and we just create an ROI score. And so the highest ROI items get pushed to the top. And we assign those individual items to people across the team. And so at our Monday meeting, we can simply discuss, hey, are we moving forward on those projects?
Mm-hmm.
We were just talking about Danny, like our Facebook reviews was taking a hit. We were like around 4.1. We'd had zero Google reviews. And so like Danny in charge of our customer success, that was his initiative for the quarter. And he ended up ramping up our reviews significantly, both on Google and on Facebook. And now anyone that sees our deals, they're like, this looks too good to be true. and they Google us, they can see 50+ 5-star reviews on Google. They're like, okay, this is legitimate.
Got it. You talked about the Monday morning meetings. What do you guys do in those meetings?
So the Monday morning meeting is a great time for us to do 3 things. Number one, it's an update on the goal, right? How are we tracking both on the monthly goal as well as the yearly goal? The second thing is just tracking everybody's individual goal. Everyone provides an update. on how are they moving forward on their individual goal, whether that's Facebook ads, whether that's the deals closed, whether that's the average revenue per deal, average revenue per email. Then final thing that we end up doing is we talk about our weekend. You know, it's a great time for us to just catch up, like, hey, are there any highlights from the weekend? We crack jokes for the first 5 minutes. It just sort of sets the mood for the team, and then we're able to game plan what are we gonna do for the final week, the rest of the week.
I love that because the fact that it's, okay, you have your metrics in there, but it shows, the other part is you show that you actually care about each other.
Yeah.
And not a lot of companies do that. I mean, when you hear about, especially the kind of Silicon Valley stand-up that you typically hear about, it's just one thing you're struggling with, one big thing you're working on, and then, you know, that's basically it, right?
Mm-hmm.
So I think it's really important to get that human aspect in there where you're actually, you're hanging out with each other, you're asking personal questions, things like that, because you are working with humans at the end of the day, and you don't want to go to work with people that you don't like, right? So the other thing I want to ask, I mean, so you have your daily habits. How do you get better? What do you do?
To me, like, every morning I make sure that I'm reading. I have like a daily morning ritual where I'm making coffee, reading for 30 minutes to an hour, making sure I'm hitting inbox zero so that way like my mental head is clear, and then just game planning for the individual day. And then the other thing that I love to do is like I try to schedule at least 2 or 3 conferences a week. I think like when you look back on the last 4 or 5 years, like the real difference in your trajectory is really like the books you're reading and the people that you're meeting. And sometimes when you're going to these conferences, which is one we're throwing this weekend, SumoCon, which is why you're here, right? It gives you an opportunity to meet like-minded people. These are the people that you're gonna be shooting ideas with, you're gonna be adding on Facebook, that you are gonna be potentially hiring in the future, potentially starting a business together with in the future. And so when you're able to share those ideas, you yourself will continue to get better.
What's— okay, so you sign up for 2 to 3 conferences per week?
Per month, sorry.
Per month, okay.
I mean, sorry, per year.
per year. Okay, got it, got it, got it.
Cool.
What's the best conference you've ever been to in your life?
I'm part of an online entrepreneur group called Dynamite Circle.
Never heard of it.
So it's actually thrown by Dan and Ian from Tropical MBA. And in 2013, they threw one while I was living in Munich, Germany, in Berlin, Germany. And so I was just randomly following them on Twitter. I tweeted at them. I didn't even know what the Dynamite Circle was at the time. And I just asked, hey, can I come to the event? They're like, well, it's sold out, you know, like, you know, it's typically only for members only. And I'm like, members of what? I just kept pinging them, bothering them, and then all of a sudden they're like, hey, we actually have one extra spot available if you want to come up this weekend. Bought the ticket, went up, and it was amazing. Like, I ended up meeting like a ton of really awesome entrepreneurs, but the best part about it was it was a small event. It was only 150 people, which we're trying to recreate with SumoCon, keeping it super small. And it gave a lot of chance encounters to run into the same people over the weekend. and create a lot of lifelong friends. Some of them I'm still friends with to this day. Some of them are actually now working at AppSumo.
Key takeaway, it's not what you know, it's who you know, right? Is there anything else you'd like to add?
Yeah, you know, I think like for those that are just going on the entrepreneurial journey, I think it's a great way to just make the world a better place, like in your own little world. I think the key takeaway for them is just constantly like analyzing over the last year, 2 years, what has been your top 3 Top 3 wins, the top 3 things that have helped you move forward closer to your goal, and just go do more of that. Entrepreneurship is not that difficult. It's not that hard to uncover. We don't need to overcomplicate it. If you simply just analyze what's worked really well, don't read the latest blog post, just look at what's worked well for yourself and just go do more of that.
Makes total sense. So there's a book I recommend, it's from Peter Drucker, it's really short, it's called Managing Oneself, and it basically tells you how to audit yourself all the time and all these other things. So actually, I have a final question for Eamon. What's one book you'd recommend to everyone?
You know, right now I'm actually, I'm reading this one, Mastering the Rockefeller Habits. It's actually a really, really good one. So that's one I'm really enjoying right now. Cool.
Well, Eamon, thanks so much for joining us.
Eric, appreciate it.










