The Exchanges

Q I love it. Why did you come up with the idea?

A Uh, we had many startup ideas that we're playing with, um, but this one came from our previous job. And I think like many B to B startups, you might find a problem or a gap, uh, in your, in your work, and then you, you have the idea to build something better. So, um, Jonathan and I, we were both, uh, engineers in a on-demand delivery startup. And, uh, we were, the startups was hiring lots of contractors. Uh, we were looking at the background check process. That was a bottleneck to hire people fast and with a good experience. And, uh, after looking at the options on the market, we realized, uh, there was a, a gap and, and no great solution. So we said, Hey, I think we can build something, something better here.

AI assessment note: “this one came from our previous job”

Q Totally get you. Um, can I ask, when you think about, like, advising founders today, in terms of, you know, their own personal development, final one, but like, where do you think most of them are weak? Like, are there commonalities in where you find founders need help?

A I think it depends on the personality of the founder. So, you know, I'm more of a, you know, hard charging, intense, confident, you know, perfectionist, direct kind of founder. And there's many other founders like me. So for, for the, the, the intense founders like myself, I think you need to work on self-awareness, listening, empathy, you know, putting yourself in other people's shoes and bringing people on together, not just your sheer power and will, but I also have other founder friends who Um, how are very empathetic and patient and, you know, don't like conflict. And so for those, they need to do the opposite. They need to actually be more direct, get, get more conflict, make the hard decision and hard calls. Um, so there's, there's just different human personalities, but, but if you're an intense founder, hard charging, I think you gotta work on the soft skills and self-awareness so that you work better with that, with other humans and, and teams.

AI assessment note: “I think it depends on the personality of the founder.”

Q I think another area is board management. I, I don't know any first-time founders that are innately skilled at board management and quite rightly so, it's a weird thing to be skilled at. When you look at board management, what do you think it takes to manage a board effectively and what have you learned over the years with regards to it? You've got some big hitters on the board.

A Yeah, I'm very fortunate. My, my board is amazing and, and they really helped me a lot in the journey and even helped me on how to manage the board. Uh, I have some other executives or previous founder CEOs on the board who, who helped me on how to manage the board. Um, I think there are similarities with managing your leadership team and managing your board at the end of the, of the day, it's also a team and a group of people who are here to work on the business and to help the business. So I think. You know, a few things. So first it's important, I think, to be very transparent with the boards, just share the truth, what's going well, and also what's not going well. Um, you don't want to sugarcoat or have just a rosy picture of your company with the board. That's going to create the divide of understanding of where the company is, um, and, and actually create more pressure. I think for the board can be scary for founders too. So sometimes you want to please your board and, and really take every feedback and ask, Um, immediately to heart and execute on it. But, um, sometimes you might not be able to, or it could be conflicting feedback, or maybe not the best thing for the company. Uh, for me, I would say a few years ago, there was pressure on financials, revenue growth, which is always going to be some type of pressure from the board who wants, of course, the company to, to, t…

AI assessment note: “first it's important, I think, to be very transparent with the boards”

Q Um, have you ever, have you ever drank your own Kool-Aid too much? I've done this too on the flip side, which is, you know, you raise a ton of money. A lot of smart people say you're a genius at 23 and you're like, yeah, I am. Yeah, I'm really good. Have you ever had the alternative where actually you get too confident?

A Yeah, no, it's possible. It's, it's, it's a hard balance. I think, um, especially in the early years when you get a lot of traction, you know, you think that any product we do, any move we do is going to be successful. And, and I'm lucky that I got some punches in the face and, uh, you know, we've had some very hard year in 2019, 20 20. Uh, so, so when problems hit, it's, uh, it's humbling and I'm glad We've had some of that because otherwise you can tend to get too confident. Uh, so it's a, it's a balance. You want to be confident without, uh, without losing that humility and perspective. So definitely I've been oscillating between some insecurity sometimes in the hard times and, uh, and overconfident when things are good. But, uh, I try to, to stay grounded. My, my family and my wife has been actually a good Um, support for me to, to keep me grounded, ah, on earth.

AI assessment note: “definitely I've been oscillating between some insecurity sometimes in the hard times and, uh, and overconfident”

Q I was chatting with them, there were a couple of areas that were very much commonalities in the discussion points. So let's start on delegation. I think most founders suck at it, especially first time founders. So when we think about delegation, how do you and how did you extract yourself from the weeds of what you didn't need to do? How did you put the support structures in place?

A Yeah, I, I would agree that, uh, first time founders suck at it. I, I, I sucked at it a lot. Uh, I might still do. Um, so it took me a while to, to learn how to delegate because like a founder, you want to make sure everything's perfect and good. And that, you know, I have a high bar and, and I liked, I liked the details and how things are built and how things are done. So I think for many years, um, I was very bad at it. And then, um, what helped is hiring good, strong, more, more senior people. So actually our first hire, um, was one of our Android investors, Pascal, who was really good and experienced in other startups in many, many areas. And so when he started to take on things off my plate and doing things very well, that gave me a little bit of confidence to, to delegate, but it's been a long journey, um, to try to delegate, I think. You kind of have to force yourself to do it as a founder. I mean, there's, there's so much you can say about like the person and everything, but I think for many founders like me, I had to, after hearing the feedback that this is not going to scale, there's not enough time. I have to prioritize other things. I had to force myself to let go of some areas. I think one thing that helps is, um, to then focus my mind on other things. So if you can kind of focus your mind on other bigger problems that only the founder can work on, like. You know, …

AI assessment note: “what helped is hiring good, strong, more, more senior people”

Q When do we expand into Europe? When do we expand with a new product? Do we hire a COO? And that's your discussions for the one hour. Financials are sent three days before, and they can review them ahead of time, and if there's any serious problems, then they can bring them up in the board meeting and any other business. Why have a three or four hour board meeting?

A Yeah, no, that's, that's, that's a good question. I think, uh, it can be more efficient. Um, things we've done is we send the board's information away ahead of time, multiple days before. All of the financials are already kind of in the appendix, so we don't spend any time talking about those. And then we, we have debates mostly on products, strategy, go to market strategy, leadership structure, the topics you mentioned. So I think those are the right ones. Um, yeah, I mean, it, it, it can be done efficiently, potentially in one hour or two, uh, board meetings do tend to drag more and more, but I think if you can have 3:04 hours, that's actually proactive debates. You learn something out of it. The company makes progress after having strategic debates. Um, that's, that's a positive. And I would say that's rare. Many board meetings, it's not, it's not adding value. It's actually, you know, Creating more burden and work for the, for the leadership team and the CEO. So I, I, I think we're lucky that our board meetings add value and are strategic.

AI assessment note: “if you can have 3:04 hours, that's actually proactive debates. You learn something”

Q I was chatting with them, there were a couple of areas that were very much commonalities in the discussion points. So let's start on delegation. I think most founders suck at it, especially first time founders. So when we think about delegation, how do you and how did you extract yourself from the weeds of what you didn't need to do? How did you put the support structures in place?

A Yeah, I, I would agree that, uh, first time founders suck at it. I, I, I sucked at it a lot. Uh, I might still do. Um, so it took me a while to, to learn how to delegate because like a founder, you want to make sure everything's perfect and good. And that, you know, I have a high bar and, and I liked, I liked the details and how things are built and how things are done. So I think for many years, um, I was very bad at it. And then, um, what helped is hiring good, strong, more, more senior people. So actually our first hire, um, was one of our Android investors, Pascal, who was really good and experienced in other startups in many, many areas. And so when he started to take on things off my plate and doing things very well, that gave me a little bit of confidence to, to delegate, but it's been a long journey, um, to try to delegate, I think. You kind of have to force yourself to do it as a founder. I mean, there's, there's so much you can say about like the person and everything, but I think for many founders like me, I had to, after hearing the feedback that this is not going to scale, there's not enough time. I have to prioritize other things. I had to force myself to let go of some areas. I think one thing that helps is, um, to then focus my mind on other things. So if you can kind of focus your mind on other bigger problems that only the founder can work on, like. You know, …

AI assessment note: “what helped is hiring good, strong, more, more senior people.”

Q When do we expand into Europe? When do we expand with a new product? Do we hire a COO? And that's your discussions for the one hour. Financials are sent three days before, and they can review them ahead of time, and if there's any serious problems, then they can bring them up in the board meeting and any other business. Why have a three or four hour board meeting?

A Yeah, no, that's, that's, that's a good question. I think, uh, it can be more efficient. Um, things we've done is we send the board's information away ahead of time, multiple days before. All of the financials are already kind of in the appendix, so we don't spend any time talking about those. And then we, we have debates mostly on products, strategy, go to market strategy, leadership structure, the topics you mentioned. So I think those are the right ones. Um, yeah, I mean, it, it, it can be done efficiently, potentially in one hour or two, uh, board meetings do tend to drag more and more, but I think if you can have 3:04 hours, that's actually proactive debates. You learn something out of it. The company makes progress after having strategic debates. Um, that's, that's a positive. And I would say that's rare. Many board meetings, it's not, it's not adding value. It's actually, you know, Creating more burden and work for the, for the leadership team and the CEO. So I, I, I think we're lucky that our board meetings add value and are strategic.

AI assessment note: “if you can have 3:04 hours, that's actually proactive debates. You learn something”

Q and I mean this with total respect before with Checker, they've been pretty high, and I've always thought, wow, That's pretty high. Um, and then you've always done incredibly well, and, you know, raised subsequent great rounds. But did you worry about raising it high valuations and being able to live up to it? And what would you advise founders having been through some very competitive and high priced rounds?

A Yeah, no, I, I do a lot. Um, and, uh, at Checker, actually, we've been quite conservative on all of our fundraisers. So we rarely fundraise really too far ahead of our scale. Um, we've always been a profitable business, which most companies are not. Um, so actually, you know, we, we are, we're lucky to not push the valuation too high. We never fundraise that, you know, 30 to a hundred times revenue multiple or so things like that. We actually always had pretty Reasonable, I would say lower valuation than other companies. Um, and we, we are very careful with the amount of money we raise and the, and the, we have almost no burn, uh, and are profitable most of the time. So I've been more on the conservative type, uh, side of the spectrum and I'm involved with many other startups and companies. And I always try to coach them on not raising too much money and then being stuck, running out of money and having to do a down round, which is a horrible situation. So I think the risk is high now, especially with the crazy valuations from the last year or two. Um, but knock on wood, I think with checker, we've, we've been careful not to push the valuation too high and also to, to make sure we're, uh, always profitable or very close profitability, which then you own your own destiny. If you're profitable, you can always, you know, keep pushing for a few more years and, and, and catch up to …

AI assessment note: “I always try to coach them on not raising too much money”

Q What was the hardest fundraise for you? When you look back, was there one fundraise that was a bear to get over the line?

A Yeah, I think it was our Series C, um, hardest. I mean, overall we've been lucky. I've had really fast, easy fundraisers because the business has been performing well and we have a good team. Um, but the Series C, uh, was one of the hardest because we got the term sheet for the Series C and then we, you know, our revenue slowed down a little bit. So we missed the quarter, uh, in terms of, uh, revenue targets compared to what we had in the Series C pitch. And, uh, the investors in the, in the series C, uh, started to get worried and we haven't closed the round. So we actually had to, um, negotiate very slightly some of the terms to get it back on track and close it. I'm grateful that the investors were flexible and friendly, but there was one, one that was harder. Um, yeah.

AI assessment note: “Yeah, I think it was our Series C, um, hardest.”

Q What was the best decision then? Where are you like, yes, I deserve a fucking medal for this.

A I, I mean, I don't know. It's been a lot of good little decisions. Maybe if I can pinpoint one or two I mean, I think, you know, starting the company to be an API first, uh, the way we did it, I think was really good. And today it's still differentiates us. So building an API, being an API first company and being focused on the developers, that has been magical for us, like brought us so much growth, so differentiated, uh, and still helps us win today. Another one is we've done some pretty good M&A and acquisitions early on. Um, we're a data company at Checkr and we, you know, I, I decided earlier on to, to buy some of our data suppliers and, and supply chain, which was a non-obvious decision. And that has been a very good investment and move. So yeah.

AI assessment note: “starting the company to be an API first”

Q Do you not think that everything can be delegated away essentially? Launching a new product? A product manager can do that. A great product manager. Fundraising, I agree. Setting the mission, I agree. Hiring a C-suite as well, but pretty much everything else can be delegated away, don't you think?

A Yeah, absolutely. Everything can be delegated. And, uh, but in the early days, there's always going to be some gaps in your startup, right? Like you might not have a head of sales or a head of product or recruiting team, so you can go, you know, push hard in the areas where there's no coverage. Uh, the best thing you can do is hire someone. So I completely agree that the highest leverage activities you can do as a founder is hiring the best bench and C-suite and VPs you can. Um, Setting the vision. That's only something you can do, you know, finding the values and the purpose of the company or mission, um, being the cheerleader of the company in the media, outside, um, you know, fundraising. Those are some of the highest leverage activities only the, the founder or CEO can do. Also spending time with customers is very important, and I don't think you should delegate all of that. Um, founders should stay close to the customer.

AI assessment note: “Yeah, absolutely. Everything can be delegated. And, uh, but in the early days”

Q I think another area is board management. I, I don't know any first-time founders that are innately skilled at board management and quite rightly so, it's a weird thing to be skilled at. When you look at board management, what do you think it takes to manage a board effectively and what have you learned over the years with regards to it? You've got some big hitters on the board.

A Yeah, I'm very fortunate. My, my board is amazing and, and they really helped me a lot in the journey and even helped me on how to manage the board. Uh, I have some other executives or previous founder CEOs on the board who, who helped me on how to manage the board. Um, I think there are similarities with managing your leadership team and managing your board at the end of the, of the day, it's also a team and a group of people who are here to work on the business and to help the business. So I think. You know, a few things. So first it's important, I think, to be very transparent with the boards, just share the truth, what's going well, and also what's not going well. Um, you don't want to sugarcoat or have just a rosy picture of your company with the board. That's going to create the divide of understanding of where the company is, um, and, and actually create more pressure. I think for the board can be scary for founders too. So sometimes you want to please your board and, and really take every feedback and ask, Um, immediately to heart and execute on it. But, um, sometimes you might not be able to, or it could be conflicting feedback, or maybe not the best thing for the company. Uh, for me, I would say a few years ago, there was pressure on financials, revenue growth, which is always going to be some type of pressure from the board who wants, of course, the company to, to, t…

AI assessment note: “first it's important, I think, to be very transparent with the boards”

Q Um, have you ever, have you ever drank your own Kool-Aid too much? I've done this too on the flip side, which is, you know, you raise a ton of money. A lot of smart people say you're a genius at 23 and you're like, yeah, I am. Yeah, I'm really good. Have you ever had the alternative where actually you get too confident?

A Yeah, no, it's possible. It's, it's, it's a hard balance. I think, um, especially in the early years when you get a lot of traction, you know, you think that any product we do, any move we do is going to be successful. And, and I'm lucky that I got some punches in the face and, uh, you know, we've had some very hard year in 2019, 20 20. Uh, so, so when problems hit, it's, uh, it's humbling and I'm glad We've had some of that because otherwise you can tend to get too confident. Uh, so it's a, it's a balance. You want to be confident without, uh, without losing that humility and perspective. So definitely I've been oscillating between some insecurity sometimes in the hard times and, uh, and overconfident when things are good. But, uh, I try to, to stay grounded. My, my family and my wife has been actually a good Um, support for me to, to keep me grounded, ah, on earth.

AI assessment note: “definitely I've been oscillating between some insecurity sometimes in the hard times and, uh, and overconfident”

Q Do you not think that everything can be delegated away essentially? Launching a new product? A product manager can do that. A great product manager. Fundraising, I agree. Setting the mission, I agree. Hiring a C-suite as well, but pretty much everything else can be delegated away, don't you think?

A Yeah, absolutely. Everything can be delegated. And, uh, but in the early days, there's always going to be some gaps in your startup, right? Like you might not have a head of sales or a head of product or recruiting team, so you can go, you know, push hard in the areas where there's no coverage. Uh, the best thing you can do is hire someone. So I completely agree that the highest leverage activities you can do as a founder is hiring the best bench and C-suite and VPs you can. Um, Setting the vision. That's only something you can do, you know, finding the values and the purpose of the company or mission, um, being the cheerleader of the company in the media, outside, um, you know, fundraising. Those are some of the highest leverage activities only the, the founder or CEO can do. Also spending time with customers is very important, and I don't think you should delegate all of that. Um, founders should stay close to the customer.

AI assessment note: “Yeah, absolutely. Everything can be delegated. And, uh, but in the early days”

Q What was the best decision then? Where are you like, yes, I deserve a fucking medal for this.

A I, I mean, I don't know. It's been a lot of good little decisions. Maybe if I can pinpoint one or two I mean, I think, you know, starting the company to be an API first, uh, the way we did it, I think was really good. And today it's still differentiates us. So building an API, being an API first company and being focused on the developers, that has been magical for us, like brought us so much growth, so differentiated, uh, and still helps us win today. Another one is we've done some pretty good M&A and acquisitions early on. Um, we're a data company at Checkr and we, you know, I, I decided earlier on to, to buy some of our data suppliers and, and supply chain, which was a non-obvious decision. And that has been a very good investment and move. So yeah.

AI assessment note: “starting the company to be an API first”

Q What would you advise others when it comes to CEO coaches? Having not had one and now having had two actually different ones, what would you advise other founders on when to get one, the type to get, and how to use them?

A Yeah, it's been the best thing in my life. Uh, it did change my life. I don't know if I would have made it that far without, without this help. So I absolutely recommend it to any CEO. I mean, unless you are a CEO and you feel like you're doing amazing and there's nothing you can improve on, uh, which I would be skeptical for any founder or CEO. I think it's, it's the best investment you can make. Many people tell me that they don't have the time to, to spend time with a CEO, with a coach. I think that's BS because having a coach helps you better prioritize your time, um, be more effective as a leader. And then what, what type of coach? I've, I've interviewed a bunch. I've asked for referrals. Um, I think you, you just, I don't know. I couldn't, the best thing for me was to, um, to interview a bunch of coaches, ask them what type of leaders they work well with. Uh, you know, share your, your weaknesses and areas to work on and, and test them. So I think doing some testing with a few different coaches might be the best way. I think that the personal fit is, is very important. You feel like you enjoy this person and, and you think they're gonna help you. So most of them are happy to do like a, you know, trial session, one or two coaching sessions. So I would, I would encourage people to, to, to just try different coaches and see the ones that that's best for them.

AI assessment note: “the best thing for me was to, um, to interview a bunch of coaches”

Q What would you advise others when it comes to CEO coaches? Having not had one and now having had two actually different ones, what would you advise other founders on when to get one, the type to get, and how to use them?

A Yeah, it's been the best thing in my life. Uh, it did change my life. I don't know if I would have made it that far without, without this help. So I absolutely recommend it to any CEO. I mean, unless you are a CEO and you feel like you're doing amazing and there's nothing you can improve on, uh, which I would be skeptical for any founder or CEO. I think it's, it's the best investment you can make. Many people tell me that they don't have the time to, to spend time with a CEO, with a coach. I think that's BS because having a coach helps you better prioritize your time, um, be more effective as a leader. And then what, what type of coach? I've, I've interviewed a bunch. I've asked for referrals. Um, I think you, you just, I don't know. I couldn't, the best thing for me was to, um, to interview a bunch of coaches, ask them what type of leaders they work well with. Uh, you know, share your, your weaknesses and areas to work on and, and test them. So I think doing some testing with a few different coaches might be the best way. I think that the personal fit is, is very important. You feel like you enjoy this person and, and you think they're gonna help you. So most of them are happy to do like a, you know, trial session, one or two coaching sessions. So I would, I would encourage people to, to, to just try different coaches and see the ones that that's best for them.

AI assessment note: “doing some testing with a few different coaches might be the best way”