Jeremy and David Podcast Cover copy

This conversation between my CEO, David Karandish, myself, and Hallie Warner originally aired on The Founder and The Force Multiplier Podcast and I’m excited to re-post it here on The Leader Assistant Podcast!

How has our partnership thrived since 2017?

Tune in to this fascinating conversation as we share the secrets behind our successful partnership, from overcoming early challenges and how the partnership has evolved as Capacity has grown, to maintaining work-life “wholeness” through intentional communication and scheduling.

We also explore the impact of AI and automation in the workplace, and how AI is replacing cognitive labor and the implications this has for EAs.


David Karandish is Founder & CEO of Capacity – an enterprise SaaS company headquartered in St. Louis, MO. Capacity is a support automation platform that uses AI to deflect emails, calls, and tickets so internal and external support teams can spend more time doing their best work.

Prior to starting Capacity, David was the CEO of Answers Corp. He and his business partner Chris Sims started the parent company of Answers in 2006 and sold it to a private equity firm in 2014 for $960m.

David sits on the boards of Create a Loop (a computer science education non-profit tackling the digital divide by teaching kids to code) and (a non-profit providing educational resources and strategic guidance about Artificial Intelligence to individuals, communities, and companies). David was also an early investor and board member at Nerdy (NYSE: NRDY), an on-demand, real-time learning platform in the ed tech space.

David lives in St. Louis with his wife, Erin and four kids. When not working, he enjoys spending time with his family and playing ukulele.

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Hallie Warner 00:02
Welcome to this week’s episode of the founder in the force multiplier Podcast where we explore how founders and leaders work together with their right hand partners to turn ideas into action and build a wildly successful businesses. Hi, David and Jeremy, welcome to the podcast. Thank you so much for being here. Thanks, guys. So let’s just get right into it. So David, you co founded capacity in 2017. Why was your first hire and executive assistant?

David Karandish 00:29
I believe that a great EA is like having a great partner. Without, I know myself well enough to know what I’m good at and what I’m not good at. I know myself well enough to know that I need someone who can help me drive and be more effective. And it truly is a force multiplier. When you bring on a great executive assistant to work with a CEO, particularly in a startup where you don’t have a lot of structure, you don’t have a lot of process. It’s all hands on deck. Having a great EA is a difference maker.

Hallie Warner 01:05
What does, What does, did that maybe like first six months to 12 months look like working with, the with an EA versus what the partnership looks like today.

David Karandish 01:15
I think when you start an organization, you are trying to fly the plane as you’re building it in the air. And so there was a lot of in that first kind of six months, a lot of time of doing anything from finding office space to doing incorporation data to getting our first recruits on we didn’t have a recruiter when we started, Jeremy was our recruiter, Jeremy was our office administrator, Jeremy was our keep the lights on person for 12 different areas of the organization.

Hallie Warner 01:48
And today, how does that, like how do you, how do you work together today? What does that look like? How are you communicating? How are you managing projects and priorities?

David Karandish 01:57
Yeah, I mean, first thing is we do a weekly one on one where I, despite my hectic schedule, I tried to make that every single week and not move it, not make it a punted to next week sort of thing. We also are obviously very big on using slack, we are communicating with each other all day back and forth on Slack. We also use capacity to help automate certain things. So answering certain types of questions that I would have to go to Jeremy for before, I’ve got the bot to answer some of that stuff as well. And then the other thing I would say is, and this was I think this is really important. In my last company, I worked about the same amount, so 60 hours or so a week. But I had a very up and down schedule. So it was very different from day to day, very different from week to week, there wasn’t a lot of norms around what that could look like. So one night, I might be home for dinner with my wife at 530. And other wife another night that other way. Another night, I might be home at closer to 8: 30. And so when we started this company, one of the things that Jeremy and I worked through is what would the ideal calendar look like? How can we take what’s still going to be a lot of work, but try to create some discipline around. Like for me Every Monday and Wednesday night, I work late. Every Tuesday night, I do a date night with my wife. Thursday nights kind of flex, I take a kind of work Sabbath email, Sabbath, Black Sabbath from Saturday afternoon to Sunday afternoon. And so figuring out those rhythms was really helpful, because then also for Jeremy, it’s like, oh, Jeremy knows, David’s working late on Wednesday. Jeremy knows not to ping David at seven o’clock on a Tuesday when I’m on date with my wife. So it’s that kind of rhythm, getting that setup right from the beginning was crucial to making sure we can both be optimally productive.

Hallie Warner 03:56
Yeah, so it sounds like you had a very intentional conversation about not just the calendar, but in my mind, it’s also about, you know, work life balance. And that was obviously maybe important to you. But I’m also curious for both of you like what is your philosophy around work life balance. It’s such a buzzword these days. But what does that really mean to each of you? And how are you engaging in that and also engaging in that with the conversation with the rest of your company? Is it just between the two of you, or does that sort of philosophy permeate the rest of your organization?

Jeremy Burrows 04:28
Yeah, so I think early on what we did when we were smaller, we instituted Wednesday work late across the company. It wasn’t necessarily required, but it was encouraged and we got some dinner and we just worked on brainstorming and building and figuring out creative solutions to the problems that we had. And so that was kind of showing like, Hey, we are we’re inviting you to join us on this kind of structured idea week. Calendar. And then I think as the company has grown, it shows up in different ways. Like, for example, David’s very clear about like he mentioned his 24 hour, no email, no slack, you know, block on the weekends. And then we also instituted before. So slack did not have the feature to schedule messages initially. And so we had an I think we had an extra bot or something that we added to do this. But now thankfully, Slack has that built in where you can actually schedule message. So David has done a lot, a lot better job of, hey, you know, if it’s midnight, and he’s working late on Wednesday, and he has a crazy idea, and he wants to send it to someone, you know, he can send it to them, but they don’t get a ping at midnight. They get it the next morning during work hours. And so he’s able to schedule that. So just being intentional with things like that has, I think has shown the team that, you know, we respect their, their personal life and their family time. And we’re, we’re going to work hard, and we’re going to work a lot. But we’re going to also rest well and take time off.

Hallie Warner 06:07
Yeah, I really appreciate that you’re so transparent about it, and that you’re really leading David especially, you’re leading by example. Because very often people will say that’s what they believe in their organization, but then the leader and sometimes the EA, they’re not they’re not operating that way at all. They’re, they’re totally disrupting everyone else’s life.

David Karandish 06:26
Yeah, I mean, I mean, Jeremy came from a previous gig where it was pretty expected that he was on call through the weekend. And I don’t know, I think in the last year, how many times we talked on the weekend, maybe three times? Yeah, I don’t know. Something like that. So yeah, I think it starts from the top. I also, I don’t love the term work life balance, because it connotes like, Hey, I’ve got this scale and if I just put enough work here or enough personal time here, then it all just kind of evened out, I like to think of more work life wholeness, where you are wholly in what you’re doing, when you’re doing it. So if I’m at my aquarium field trip, I am not checking slack I am wholly in while I am there. Conversely, when I’m working, I am working, I’m not messing around to use an Arrested Development phrase, I like I’m to feed in when I’m on my date night with my wife, I’m not out, you know, firing through emails and doing stuff like that. So I kind of think of it less, hey, we just have to go tip the scales and get them all everything in this equal balance. You’re gonna have times in your life where personal things are personal time needs to have a bigger dialogue or certain work seasons that were things you’re gonna have to dial up. But it’s more about are you being whole, are you holy in two feet in whatever you’re doing at all time. And I can say I have many leadership challenges, failures, issues, flaws, Jeremy Burrows, all of them.

Hallie Warner 08:09
Jeremy, want to share all of this us?

Jeremy Burrows 08:11
we don’t have time, we don’t have time…

David Karandish 08:13
For a different day… But I haven’t met anyone who’s like, you know what that David really, he’s really not two fit in and what he does, and that’s those are the types of people we want to work

Hallie Warner 08:22
on. Really? Yeah, completely agree. I don’t want we don’t love the work life balance at our company, either. We call it work life presence, which is very much what you’re calling it that work life whole that wholeness. So obviously, time is something that you guys probably talk about a lot. And it sounds like you’re constantly optimizing time in your workdays. And clearly, that’s what capacity helps teams with is saving time solving major issues for teams, reducing time spent searching for information, answering repetitive tasks. So how is you know, what do people need to know in order to embrace AI automation, and tools like capacity, and other tool language tools like chat GPT? It’s clearly at the heart of your organization, like what do people need to know?

David Karandish 09:04
it’s a little let’s kinda start at the top. If you look at the history of computing, it’s been a history of taking machines and abstracting away different interfaces. So my dad was an electrical engineer, he worked on physical computers with switches and, and physical devices, and then punch cards and then DOS and then windows and then web and now mobile app. So each time what we’re doing is we’re, we’re abstracting away from the zeros and ones. The current paradigm where we’re at is we’re now at the point to where natural language can abstract away as an interface from what we want to do technologically. So I could ask Alexa, what the weather is, I could ask capacity, how do I connect to the VPN? So you have that kind of path going and if you think about where we’re heading ultimately with that, think the natural language processing is the penultimate interface before we get to the final interface of thought, being able to think your question and have it linked directly back into an AI system, we’re not there yet. But that will be, that will be on the horizon. So that’s kind of one, one thing that’s happened. The other thing that’s happened is, companies have moved their systems of record, from these on premise servers in the back room, kind of setups to the cloud. And everybody thought, wow, if I’ve got my CRM in the cloud, I’ve got my ducks in my cloud, I’ve got my help desk in the cloud, all my problems are gonna get solved. And it turns out that the systems of record are not great systems of engagement. And so you end up with Salesforce instances that are really bloated, when somebody just wants to go add a quick note to a particular particular contact, or you end up with people having to dive through folders and folders and folders on SharePoint, when really, they just want to ask the question into the policy and go get there with their answer back. So you’ve got the abstracting away of these interfaces, to where natural language is now prominent, you’ve got everybody moving their stuff to the cloud. And then with cloud connectivity, you could put a natural language interface on top of it. But with the advent of what’s happening from an automation perspective, you might have a process that cuts across multiple systems. So if you think about onboarding a new team member, you might be scheduling something with their calendar, sending the documents out of the cloud drive, you might be updating information in the HR system. So it’s not just working in one system. It’s a workflow that cuts across the different areas of the company. So that’s another thread that’s going on. Lastly, if you look at the history of automation itself, think of automation is really just like a almost like a proxy for human labor. Right. So when the car came out, I mean, they actually sent me, they still talk about cars in terms of horsepower, right, it was literally the power of the car is measured in how many horses you replaced, right? You fast forward till we’re at now, up until recently, most automation was replacing physical labor, right? Taking that horse to this place, or you think about all the everything in a construction site, all the physical labor that’s now being done by machines to happen with AI is if if you think of AI as simply put software that learns, and applies patterns, that we now have the ability to not just outsource physical labor, but to begin to outsource cognitive labor. So an example of this might be even in our own product, that AI can answer a lot of questions, but we still have tickets to get created in the Help Desk used to be that if a ticket went to the Help Desk, somebody would have to completely write out the entire manual response. Now, we can go into the AI and say, make this longer, improve this response. Summarize the three questions above this. And so we’re taking what used to be human labor, human cognitive labor, are saying, Hey, I think AI can start to take on some of that.

Hallie Warner 13:16
Yeah, that’s, it’s fascinating and obviously, you both have been in that world for a while. And it’s starting to become a bit more, you know, new to me. But it’s just, it’s fascinating. And of course, especially with the audience that I’ve talked to a lot, one of the first questions that comes up based on fear is, this is going to just replace my job as an assistant there, you’re no longer going to need an executive assistant, in an organization. So what would you say to assistants who are, who are concerned about their jobs being replaced by AI and automation?

David Karandish 13:48
Yeah, I mean, I’d say there was a pression book that came out a few years ago, called The Leader Assistant.

Hallie Warner 13:54

David Karandish 13:55
That talked about how we are heading toward a world where if you, if you’re not using an AI to better augment and improve your job, you will get replaced by an AI. And when that came out, that was a very controversial and very minority opinion statement at the time, it was borderline provocative, I would go as far as to say, because at that point, very few companies were using AI day to day. Now, the number of executives I’ve seen in the last six months, who are completely rethinking every single role in their company. They’re now saying, If I don’t have an AI enabled support function for every single part of the org, we’re falling behind. So I think the words of you either work with the AI or the AI replaces you are absolutely, absolutely pression today.

Hallie Warner 14:51
Yeah, yeah, I agree. And I know Jeremy that you’ve talked about this before, and obviously in the book, but I’ve completely agree from day one, I mean, the value of assistant and value of an EA is not in our ability to retrieve information or in our ability to answer repetitive questions the is to make better in my opinion, it’s to be that strategic thought partner, it’s to help lead up to your executives, it’s to be that leader assistant, and help them make decisions and help lead other people in the organization. That’s my opinion.

Jeremy Burrows 15:26
Yeah, I think that’s spot on Hallie. And I think that the point of the AI taking our jobs and all that I think it’s really kind of the wrong question. I think the real question is, you should be asking if you’re an executive assistant, is what is your job? Like, What is my job? And so one of the things I like, with working with David is, you know, he, we’ve talked about this for the last few years. But he basically said, Jeremy, your job is to help me stay healthy, stay married, and stay in business. And, you know, so when I, when I think about what’s my job, that’s my job is to help David stay healthy, stay married, and stay in business. And I’m going to use tools like capacity, or Zapier or whatever, to help automate certain things along the way, that help in all three of those areas. And so I’m excited to be part of the AI revolution and embrace it, and automate before I’m automated, and all that fun stuff. And so I think that it’s just for those listening, you know, that are hesitant, jump in, try it out, sign up for the chat GBT beta sign up for, you know, Google, Bart, or whatever you say, and just try it out, you know?

Hallie Warner 16:50
Yeah, I agree.

David Karandish 16:52
The other thing I was just going to add to that is, gravity naturally pulls on all three of those, you don’t naturally stay healthy. Gravity pulls you toward that bucket of ice cream and not working out and not getting sleep and not not getting rest etcetera. Gravity pulls on your marriage, when you have a startup, when you’re growing a company, when you’re traveling all the time. Gravity pulls on business, businesses change, business is fragile, business is hard to do. So you’re not starting from rest, on all three of those, there is a force that is pulling on all three of those by default. And so a good EA coming in and saying, Hey, I’m going to help you stay healthy, and help you stay married. And I’m going to help you stay in business. That’s starting with statics and starting with Dynamics from the get go.

Hallie Warner 17:45
Yeah, yeah, I love that. And that so far, cannot be automated. The parts of it can, right, but not the not the full, the understanding the whole person and understanding, you know, all of the complexities of that person’s life and how things you know, making judgment calls about where’s time should be spent. And so that, I think that’s where the EA role is going. In many ways it’s going to be, it’s a higher level, role, certain degree.

David Karandish 18:11
And I’ll add to this, Jeremy. I’m curious to hear your thoughts on this one. But I think a lot of people think about EAs in terms of time management, like I as the EA, I’m going to help my exec get more out of his or her time. And I think that’s part of it, for sure. And I don’t want to discount that. But I actually think that energy management is just as important, maybe more important, because we all have 24 hours in a day, nobody can add or remove that. But how we spend them and the energy we can apply when someone is in a heads down, create creative mode, it’s a very different mode of operating than when you’re in a leadership, organizational development type mode versus when you’re in a sales prep mode versus when you’re in a planning set. Like these are all different modalities in which an executive needs to be able to move sometimes between throughout the day. And so part of the EA role in my perspective is not just making sure all the meetings are lined up and in place and I, you know, get to the chapel on time sort of thing, but it’s making sure that I’m at the chapel with the right person. I’m managing the energy. I have toured that particular endeavor.

Hallie Warner 19:32
Yeah, yeah, absolutely. Awesome. What are you guys working on next?

David Karandish 19:36
Yes. So we have been going very deep in terms of applying AI in an omni channel way. And when we started out, we were, put capacity into Slack so it could start answering questions over IM. We added Microsoft Teams. We’ve since added email. And we’ve now just recently added SMS so you can actually text the bot. The bot can respond, respond back. When I think about that, the next layer, we have been pushing very hard on plugging directly, not just into your email support box, but on top of your email itself. So if I sent Jeremy a question, Hey, Jeremy, how do I, how do I register for these benefits? Even if that was already in the bot, when Jeremy pulls up the email to respond, it will actually inject the answer directly into his Gmail or directly into his outlook. And so we’re making it so that we think emails should be highly automated with technology like this. Another thing we’re seeing is that EAs in particular, have so many requests for travel requests for frequent flyer numbers, requests for scheduling requests, for personal health data, all this sort of stuff. And so we’re working on a package for capacity, specifically targeted for EAs, who can come in and say, Okay, I’ve got the top 250 questions every executive asks, from you just you name it A to Z. And so instead of your new EA, joining a new organization, you should be able to get the answer to that you know, that content pack, and then be able to start automating a lot of what well, you need to go do.

Hallie Warner 21:24
That is amazing. I’m very excited to see all of that stuff come out. And I’ll be keeping an eye on what you guys are doing, because it’s very exciting. And I really appreciate you spending the time with me today.

David Karandish 21:34
Thanks for having us.

Jeremy Burrows 21:35
Yeah, thanks, Hallie. And I’ll just say like we you know, as David alluded to, we’ve been working so much on kind of the broad platform, all the different elements of the platform. Now we’re excited to go deep and one of those use cases is with EAs. So we’re hoping that we can share more about that in the coming days. Yeah,

Hallie Warner 21:53
very exciting. Awesome. Thanks, guys. Thank you. Thank you.


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