All right.
Hello and welcome to this episode of Beyond Titles.
I'm very excited to be joined by Brendan Grove today.
So we're going to have a lot of interesting conversation about, you know, translating technical language and technical skill into the business world to find success and to find
collaboration of all kinds.
So, Brendan, I would love to pass it over to you just to give us a little bit of an intro.
about who you are and your journey to this point.
Yeah, of course.
Thanks for having me.
Like you said, my name is Brendan.
I head up tech and data for PrizeOut.
So we work with both gaming companies, but more specifically credit unions, building their rewards products.
So like you said, there's a lot of translation between, you what are we doing on the backend?
How do we create this integration to how do we create the product that both our credit unions and their members expect?
without everyone needing to understand all that went into it.
This journey to this point started off at DraftKings after going to WashU in St.
Louis being a mechanical engineer and just kind of naturally picked the things I thought were most interesting and here I am.
So I'm sure we'll get into more as we go.
Yes, definitely.
And here you are.
We're so grateful that you are here.
And I'm sure that the journey has had uh mountains and valleys and everything in between.
uh So we'll start with uh an easy question, I suppose.
where was PrizeOut born from?
What was the idea behind it?
uh Did it start as an idea?
Did it start as technology?
Give us a little bit of insight there.
m
so our CEO, David, was running a paid trivia company.
So, right, I know more than you about podcasting.
So we're going to compete for $5 and winner takes, you nine of it.
And his company made a dollar.
And as that was happening, users were withdrawing to gift card.
So on one side he was acquiring users on the other side, he was basically giving them to brands for free.
And that was kind of the impetus of the idea.
I was at DraftKings at the time.
another one of our co-founders, Matt, ah who knew David through a mutual friend and uh us plus some others got together.
David explained his vision ah and basically asked each of us, like, can we do our part of it?
So for me, was, you know, can you build it?
ah I was data science at the time, which was engineering and algorithms.
And so I had my part pretty cleanly defined.
We started there and kind of
ended up in credit unions.
Can you build it?
What a big ominous question, right?
It was, can you, no, was actually, do you understand it?
Like, do you get it?
And can you build it?
And I was like, I think I understand the idea and I'm pretty sure I can build it.
And that was the kicking off point for our relationship.
Amazing.
And how many iterations have you had to date from, do you understand, can you build to now?
uh So we ended up finding early success in gaming and I think one of the directives was where else could it be or where else should it exist.
And so we ended up integrating to, I think it was 10 or 11 at one point, different industries, building products and kind of feature sets around this core idea of how do we
connect users and their money to brands outside of the traditional rail.
But Credit Unions was the one that we found uh even more success than our early days of gaming.
And it's definitely the one that we've doubled down on.
uh That has taken many iterations of the product, just in terms of how do we build something that's different, that members really love, that matches the ethos of the Credit
Union mission.
So it's been fun, it's been challenging.
It's taken, right, like the idea of this isn't good enough.
Right?
Like this doesn't meet the expectations we're setting out for ourselves, even if others might be happy with it.
So we've just continued down that path of perfecting.
Okay.
Ooh, that's a really interesting one that I'd like to dig into.
Um, because I think that there's, it's interesting when you're on a founding team and your co-founder and you have an idea of what great and excellent looks like.
And to others who come in, they might say, yeah, but people love it they're buying it.
So how do you balance and how do you have those conversations with your team to say, there's a, I guess there's a gap in expectations.
We need to close that gap.
And have you ever had to rethink those expectations for yourself to say, Hey, maybe this is good enough.
Well, the second question, definitely.
I took a personality exam at DraftKings when I became a manager and I was extreme on two things.
One was a dominant personality in terms of like aggressiveness and the other one was perfection.
And the comment was like most people with one don't have the other, right?
So like you got to be careful.
Like you expect everything to be done now perfectly.
And I was like, yeah, that's a pretty good rendition of the expectation.
So that has had to be adjusted.
think the conversation around, like, is it good enough?
A lot of times internally, it's kind of two things.
It's what are members telling us?
Like, what's the data say?
Because that's really the holy grail of everything.
ah Like, is it Craig's List looks like it was made?
in five minutes and it has probably spurned more startups than any other company.
think the second part too is just, my mom said something to me when I was little and it would be, this your best?
And if that's your best, that's okay.
ah But is this your best?
And that was across the board, report cards, it didn't matter.
So think internally too, we say, is this our best?
Is this the best we can do for members?
And if the answer is no,
then let's fix it, right?
Like, yeah, it might only be happening to 2 % of people on specific Android devices, but like, is it our best?
And so I think we kind of try to hold ourselves to that standard as well, even if it doesn't always show in the data.
I love that.
really love that.
And not only is that helpful for the quality of the product, but what a sense of ownership over individual growth that you're allowing your team to have by asking that question.
Right?
Do you notice that in tax performance?
Yeah, I think anytime people care, right, it means you're going to get two things from your team.
You're going to get opinions and you're going to get frustrations.
And if you try to eliminate either, you've kind of quashed their curiosity and their ownership and their autonomy.
But you've also, if you don't have that, you've probably hired the wrong people.
Right?
So like,
Just like what I was telling you, I'm a strong personality and you'll see it come out at times.
like if that means that people won't fire back at you, then you've done something wrong.
I like conflict.
So if I say something and you disagree and the team feels comfortable, they're just going to fire right back.
And sometimes people are like, whoa, what is happening?
And I'm like, no, it's good.
Like we care.
We all want to build something better.
um
But yeah, that's been a learning point for me too in terms of like perfection, in terms of like letting people find their way, um letting people figure out what they want to do uh
next versus me always dictating.
I just want to repeat that because that was such an impactful sentence.
When people care, you're going to get two things, opinions and frustrations.
And it's so true.
And both can be managed.
are conversations at the end of the day, but both lead to excellence.
And if both are centered around the right thing, right?
It's easy.
And we say people are very transparent with their intentions, right?
Like very few people can mask them.
Is this what they think is best for Prize Out or the member of the credit union?
Or is this what they think is best for them?
ah Sometimes people try to like mask one as the other, but nobody's as sneaky as they think they are, myself included.
I'm sure my intentions when I try to do it the other way are quite clear.
But if we're always trying to hold that thing central, right?
Like, are we building a better product right now?
ah There's no politics.
It's just work.
And it's just, you know, us trying to make something better.
And I think that it also creates this foundation of like, are we discussing or are we debating?
Because like, I don't want to debate.
um I will discuss.
Yes, yes.
Amazing.
So it sounds like you've got a open, transparent, healthy culture at Prize Out.
And would you say that it's always been that way?
Or was there a lot of work that went into developing this kind of culture?
I think it's always work.
It's probably like a...
You're not?
I can start again at that point.
note.
Okay, sorry about that.
You were saying.
Alright, I'll start with it's always work if that works for you.
Perfect.
I'd it's always work to create and maintain a culture.
um I think it starts at the top always and it always starts with the CEO, right?
Like there's no world in which the culture is probably not set by them.
um And then you need first followers, right?
No one can lead without followers.
And I think that kind of trickles down.
The one thing David said is a certain point, people need to tell your story.
um
and like nobody's perfect.
are they saying what you want them to say?
Understanding that like people are going to complain, they're going to vent, people are going to hate their boss at times.
That's just all natural.
um But I think that it's growth of us as a team too.
Like you need to build those relationships and you have to have this central group that kind of is embodying what
you want the culture to be.
And I don't think you can ever start with like, is what I want it to be.
It's different at every company.
It's different for every product.
It's different for every team.
So you kind of have to give each other space to like get better and change and learn and find working relationships.
um Changes as the team grows.
It changes as we get better.
It changes.
You bring in new people.
It's like integrating people now is different than like building the culture, which I think happened earlier.
ah And also letting it change and evolve and update.
ah So I would say it's a living organism more than it is, ah you know, a word on a wall that we came up with five years ago.
Like, I don't think that ever really.
Yeah, which is fantastic.
That's the sign of true leadership in my opinion, right?
Because it will change and it should change if you're still stuck, stagnant from five years ago, then what does that mean for your product too?
Has that evolved?
Like the words on the wall have not.
and it changes when you have different needs.
uh think it's Ben Horowitz talks about wartime CEO versus peacetime CEO.
And I think about it sometimes like wartime versus peacetime CTO is like there's yeah, there's times when you have to do things a certain way.
I try to be transparent like, yeah, this is gonna suck.
Like, we're gonna go hub and spoke like
we're going to run a lot of one-to-one here.
We're going to go super flat and it's going to be six months of craziness.
like, trust me that everything's okay and trust me that this is what we need to do.
ah But I'm not going to sit there and pull the wool over your eyes.
And other times, like you can't do that all the time.
Other times it's like, okay, now we have structure again.
We have, you know, we know where we're going.
We've, we've, we've kind of figured out a few things along the way.
So I think we've, we've ebbed and flow.
We've been product led, we've been sales led, right?
It's just not a one size fits all, especially when you're trying to make something work.
Yeah, absolutely.
With everybody with the same objective and the same goal at the end of the day.
uh And I'd really like to dig into something that you just mentioned about being product-led and sales-led and seen with a lot of organizations, especially that are
technology-focused, that there's often two different ideas of how to sell something, what that looks like in almost two different languages.
And you, as I've heard from your team, blend
those two worlds and those two languages very well.
So what's your trick in helping the teams bridge that gap that most, I would say, most CTOs struggle with?
Yeah, it's two.
think one, just being honest about who's in charge of certain decisions or certain, uh call them like roughly things.
So I think you see that even when it comes down to smaller decisions like product or who makes the final call and uh a microservice that exists.
uh Is product supporting sales or is sales supporting product?
And it can be different.
It can change.
It can be different based on the people.
It be different based on the product.
But like one person needs to lead and the other person needs to create the conflict that you know is the rocks in the tumbler making something better.
So you know if we draw that kind of analogy I guess or metaphor I don't actually know which is which.
Through to conclusion like my job is easy it is always support right like if we're building technology we're supporting product we're supporting sales we're supporting the
business we're
trying to integrate like we're either integrated or we're not and it's binary.
So I think it lets you kind of throw your ego aside.
um Let's you get into the weeds and it lets you tell the person what they need to know to get to the outcome that you need to get to.
Right?
You don't need to be the smartest person in the room.
You don't need to have everyone know that this wasn't your fault or the frustration they're experiencing is like theirs because of something in the business.
It's like
You can just recognize, like, if you flip the empathy, like, the situation could be frustrating for them.
You totally understand.
You have extreme empathy.
And, like, here's how we could solve the problem.
Like, what do you think?
ah My parents were teachers.
I think that probably helped.
ah Like, you try to explain it three different ways.
And ultimately, what I like to say to our engineers, because every engineer thinks they're the smartest person that's ever lived, for the most part.
ah
You know, we aren't always the most socially adept and we definitely think we're smarter than we are.
So what I say is it doesn't matter if you're the smartest if nobody understands.
Right?
So that's great that you have the solution.
That's awesome that you think everyone else is stupid.
Like, that's cool.
I agree, actually.
Like, let's go on to the starting point that I agree.
How do you get what we need done then?
Like, convince them.
Be the smartest person and get them on board.
Right?
If you're so effing smart.
then double them.
And so I think like, you know, those conversations don't happen a lot like that.
But, you know, there's times when frustrations bubble up and ultimately our job is support and our job is to get it done.
So let's go figure out how to do that.
Brilliant, brilliant.
And I love even the terminology that you use, right?
It's not collaborating with them, but it's supporting them, which is very much rooted in action and rooted in empathy and rooted in collaboration to some degree.
But just the framing of it looks very different than how I've heard it couched before.
So, we can see.
through uh trial and error.
Like I said, we're lucky.
We've worked with so many different industries.
uh I've seen very different companies.
Even with them, see also who's in charge there, ah who's getting pushed down on.
ah And again, how do you create that relationship?
Imagine you're trying to integrate and the other person's been told to integrate 10 things and you're one of them.
ah
Like they're already stressed.
You don't need to add to that stress.
You just like your team told you and their team told you to figure something out.
Like we're in this together.
I feel your pain.
This sucks, but we're also going to get it done.
ah So if you can be that support mechanism for them too, it's pretty valuable.
I just muted myself because that was going off again.
So that was perfect.
Caught it right before, so we got all of what you just said.
Apologies again.
Shouldn't be long.
Believe it or not, that's been going off for an hour.
uh I think it works.
I can tell them that it definitely works.
That's good feedback, right?
Like, hey, 100 % good.
Yeah, yeah.
Speaking of making things easier for people, right?
And this is something that I will say for the episode here.
I've just had to pause because the fire alarm has been going off for the last hour.
And as Brendan was just saying, you know, don't want to add more stress to somebody else's plate.
And if it works and if you've tested it and you can leave people in peace, then that's the best case.
Just let them be happy.
So...
You spoke about, you know, taking the data and taking inspiration from other industries.
And one question that I had early on that I want to come back to is why do you think you found so much success with credit unions?
specifically, and you briefly touched on it, but what specifically is the alignment there?
um Probably two.
There's obviously a product component to any success, right?
Like ah if the product doesn't work or the product doesn't resonate, it doesn't matter how much two people like each other.
But I think the continued success partnership comes down to shared values more than anything else.
I think just like what we talked about, the internal how do we make this better.
um
You know, how do we take some of that perfectionist mindset that I think can get in the way at times and turn it into a strength versus just a, you know, a negative.
ah Is credit unions ultimately have a mission to support their members ah that isn't always going to be profit first?
And I think we share a similar ethos when we build these products is we're building something that they will love, not something that we will love.
ah
Right?
Like I'm not the member.
And so we always have to kind of take that step back and remind ourselves of that.
ah But ultimately, they want to support uh people that, you know, times feel like they've been left behind or been betrayed by the financial system.
And, you know, why don't they get rewards?
Like, why do I get rewarded for taking out debt?
Like, it is a crazy concept when you think about it.
So how do we flip that and how do we get deeply embedded?
And their teams are spending as much time as ours.
They're doing a lot of work, technically, to give us the keys to the kingdom that will allow us to give their members what they think they deserve.
And there's trust there.
So they couldn't do all of those things if they didn't trust us not to go sell the data or trust us to move on to the next industry.
And I think that is shared values.
I don't think you can fake that.
Right?
Because it's every single interaction between every single person.
It's our engineers with their team.
It's this constant, like, if you are faking it, you will be found out.
And so I think that's what's given us a lot of success.
It's allowed us to integrate pretty quickly into the ecosystem.
And I think it's going to be ultimately what allows us to build better products.
So ah I think that's probably the most important part.
Brilliant, brilliant.
And I would say from what I've heard ah in this conversation as well, it sounds like, yes, the shared values are huge.
And then you back up what you're saying with data.
that shows, mean, if I were one of your clients, that would show me that I can trust you so much, not just because we have the shared values and we have the same objective and
mission, but also that you've gone out and you understand what it is that people want.
you're collecting that data and you can prove it to us that it is sustainable.
that's, so in thinking about those two paired side by side, would you say that data plus the, we'll call them the softer skills, right?
Understanding the values and whatnot are equally as important?
Yeah, think data also comes in two forms.
There's qualitative and there's the quantitative.
So I think on the whole, like, yeah, the product needs to be engaged with and needs to work.
I think on the softer side of data, it's the person who reaches out and tells you that they finally bought new sneakers for themselves with the cash back they've earned that
they've never had.
I think one of the things about credit unions, and this is
blending the data and the values is they do give a lot back to their members.
And I don't know if they've always been given credit for it.
So part of our product is just about celebrating the things they're already doing.
It's not trying to get them to be something different.
If you want points in travel and luxury in lounges, you're going to go with Amex or something similar.
um This isn't a product for them.
Like this is a product for credit unions and for their members.
And so when you hear that feedback of like, I recognize the value I'm getting and I finally did something nice for myself.
ah I think those stories go a long way as well ah because it's building on what we're trying to do.
how refreshing is that that you know in a world where things are constantly changing and evolving but staying true to the to the core and to why you started into the mission
that's that's not something you hear about all that often these days I don't know yeah
I played Call of Duty a lot growing up and they made it so complex to play that I stopped playing.
ah And I think that's how I feel personally about points and other programs.
But I think it relates to what we were talking about internally is if the things get so complex, you need a lot of people to do it, then like maybe you're doing something wrong.
Or if you can't explain the integration simply, like, maybe we should take a step back here.
And so I do think there's, what entropy always goes up.
So like things will always naturally get more complex unless you constantly try to stop it and try to refine what you're doing.
You'll always need more hires.
You'll always need a bigger team.
You'll always need six decks versus one.
And so I think that's a process that we do too, is how do we...
How do we look at what we're doing all the time and say, like, can we make this a little bit simpler?
Okay, I think we I think we got it, which is great.
I will just make a note of this and 25 and then I've got one more question and then we should round out for around the between 20 and 30 minute mark.
Is there anything I was going to ask you what you believe the the most important soft skill for anybody in the technical space to have?
But is there something else you think should be asked?
That's fine.
call it 26 even.
All right.
So Brennan, we've covered a lot of ground in a short amount of time and I can't wait to pull out some of these absolute nuggets of gold that you've shared.
There are so many really, really not just inspirational things you've said, but I think very tangible reflection points for leaders across the board to sit and say, yeah, no, our
team does that or our team should be doing that if they're not already.
So my final question for you is as a CTO, as a co-founder, uh what is, you can distill it down to one that's great, or a suite of soft skills that you feel are most important for
any technical leader to possess these days?
technical leader.
was gonna say, and for an engineer, think it's simple.
It's, kind of just giving a shit.
Like, do you care?
And if you care, it goes a long way.
um I think as a technical leader, the biggest thing that I had to learn, get better at practice um is you, you go from being the best in your domain to arguably the worst,
right?
Like you, I grew up in data science and got promoted and then I'm running front end teams and
And I think that you also get away from the tech, you get away from the code, you get away from kind of how things get done, no matter how much you try to push, is letting go of
being the best, know, inviting those opinions like we talked about, and also knowing like, is this my ego talking or is this, am I right?
Right, if there's two ways to do it, and even if it's 64, do you think in your favor, like, does it really matter?
um How can you get the person to see your concern and then handle it however they they want?
um and just like yeah, you're gonna hear things and people are gonna question you and You have to just kind of be at peace with it and take the nugget of truth from what they're
trying to tell you because they're probably not wrong you might disagree, but there's probably something that they're experiencing that you can do better, so I think I think
that's kind of
One thing for me that I've had to learn, get better at is just be okay.
ah Be okay with the frustrations, be okay with the opinions and kind of try to channel all that into like, we aligned though?
Like are we all moving in the same direction?
And if we generally are, you know, let them keep doing what they're doing.
Yeah, fantastic, fantastic.
And I have to say, ah giving a shit is also one that's never come up in this question.
And I'm so happy that you said it, because it is a big skill.
And then removing some of that ego and being OK with not knowing everything.
the there's no silver bullet framework.
Are you monolith?
Are you micro service?
Are you some variation?
Are you react?
Are you angular?
Like every person always has the new silver bullet.
Ultimately, it's like, are you going to figure out how to make this work?
And do you care?
Yeah, are you smart?
You know how to code?
Are you thinking of the right principles?
Like those are probably table stakes.
But what separates great from good is just like
I actually want to figure out what the business is trying to do and then I want to make it work faster.
And so I think that's my do you give a shit ah ideology.
I love it.
love it.
Thank you so much for taking the time to chat with me today to share all of your wisdom and your experience.
you know, final question for listeners, where can they find you and follow along your journey and just get to know you a little bit better?
um That is a great question.
I don't really maintain any social presence.
I have a LinkedIn.
don't maybe I've posted once on it.
um Our head of PR finally got me to change my headshot like two years back.
But I am at Brendan at prizeout.com.
I'm happy to chat.
um Happy to get pushback um if you disagree.
And maybe at some point I will find my way into
morpholyx fear at you know first up first I want to make the products work
Definitely.
No, I completely appreciate that.
you know what?
People can follow Prize Out's journey too, right?
So there's many other ways that we can follow along.
That's right.
Yeah, definitely follow Prize Out.
Our team loves to post and we love to celebrate some of the credit union wins.
Okay, awesome.
Well, we'll be celebrating with you and Brennan, thank you again so much.
Really, really appreciate your time.
It's been an awesome conversation.
Yeah, thanks for having me.
It's been fun.
Okay, recording.