An Entrepreneurial Mindset Can Make You Skyrocket

[00:00:00] I'm Felicia Shakiba, and this is CPO PLAYBOOK, where we solve a business challenge in every episode. The reasons behind the failure of 90% of startups are multifaceted, making it challenging to attribute to a single cause, while some attribute this failure to insufficient funding.

[00:00:27] Acquiring funding itself necessitates an entrepreneurial mindset. But what exactly constitutes an entrepreneurial mindset? And how can it be fostered within a founding team to facilitate better decision making? In her article on the three traits of an entrepreneurial mindset, Meredith Summers highlights the importance

[00:00:47] of being solutions-oriented, adaptable and anti-fragile. Today, Jason Park, CEO and co-founder of Coldcart, shares his insights on the significance of an entrepreneurial mindset in launching a startup. He stresses how the success of his team members depends on cultivating this mindset and offers

[00:01:08] strategies for nurturing it within the team. Jason, welcome to the show. Make sure you're having me, Felicia. I'm glad to be here. We're excited to have you. Jason, could you please start by introducing Coldcart and explaining the core problem your company is focused on solving?

[00:01:27] So we are a technology platform for e-commerce brands with perishable products. So specifically, if your product is frozen or refrigerated, think like a meal chip or a frozen box of steaks or something like that. It is prohibitively expensive and prohibitively complicated to ship to your customers because

[00:01:48] the product spoils. So because the product spoils, you have to constantly change how you ship based on the temperature and the weather, on time delivery. And you have to do that while getting the lowest cost possible. This is just so unwieldy for companies.

[00:02:04] So we've created a technology platform that automates process across warehouses, shipping carriers. We figure out down to the level of each individual box, how many hacks of ice should you put in that box, for example? And all of that runs through a single plug-and-plug platform.

[00:02:22] And so companies on our platform are typically saving about 15% to 50% cost for shipment. And we've been reducing spoilage and refunds from lake shipments by about 52%. So just getting started, looking forward to continuing to scale this business. It's been quite a journey.

[00:02:39] We got a great team that we've been fortunate to bring on to do that with us. It's a pretty impressive problem you're taking on. It's very detailed and it sounds like you've put a lot of work behind coming up with a working solution.

[00:02:54] I'd like to refer to an article I read by Meredith Summers. And in her article on the three traits of an entrepreneurial mindset, it highlights the importance of being solutions-oriented, adaptable, and anti-fragile. Are these competencies important to you? Do they apply to your world?

[00:03:17] 100% it definitely resonates, whether it's a cold-cube or other situations I've been in where we were creating a new business or if I could just solve me a problem in a way that had it been solved before.

[00:03:31] And I think what also resonated about the article was the argument that, yes, startups definitely need this, but startups alone can't solve all the world's problems. You need large corporations. You need government. You need NGOs who also have an entrepreneurial mindset and can solve problems when you think

[00:03:48] about it. That's a lot of people who need to have this entrepreneurial mindset. And I think one thing that I've often thought about in this context is, I think it's commonly believed that the entrepreneurial mindset is a setup in nature personality traits,

[00:04:05] who you are versus something that can be taxed. And I think what they have really been trying to do is try to think of it not necessarily in terms of personality traits and sort of things that are inalienable.

[00:04:20] But what does it look like when people who have this mindset work? How do they approach a problem? What's distinct about that? And maybe by getting to a more framing of it, that we could kind of help more people

[00:04:33] have that kind of mindset or kind of solve problems in the way that I think I would agree with the article is needed in our society. But yes, it definitely resonates. And so as you continue your journey, how does the definition of entrepreneurial mindset take shape for you?

[00:04:49] Our customers are trusting us with one of their most, if not the most mission critical process they had. These were fulfillment of an order and delivery of that order to a customer. That touches every sale they make.

[00:05:03] And it's a process with a lot of steps and a lot of details below the surface and frankly a lot of interest views on how those steps should be performed. And so from a kind of as we're developing our product in our business, you know, our

[00:05:19] child was kind of two full. One was that because this is such a mission critical process, the bar on quote unquote minimum viable to use that kind of product management term, there's a very high level

[00:05:33] of minimum liability of every step of that process and a very high bar that customers are expecting it clear for them to actually trust you with their business and their customers. And so how that shows up at cold call there are three things that I've observed to you

[00:05:49] with a team and myself and just thinking about these things. And it comes out of how do these people work? How do they approach problems? I think there are three factors that I think sort of show up consistently.

[00:06:04] One is a focus on why over what you get a lot of information every day. You talk to people, you see and hear a lot of things, but this is really about going beyond what you see and hear and really digging for underlying causes, origins,

[00:06:21] motivations, that's that level where you actually start to solve problems in ways that are different and better. But you have to be the one to dig for those types of insight. They don't present themselves. Think about, for example, every company we meet, every brand we meet usually will

[00:06:42] say something at the beginning like, oh, I want to ship through UPS. Why do you want to ship through UPS? Oh, because I have discounts at UPS. OK, well, how's your all time delivery? Oh, I'm reached by the 10% of my shipments this past month

[00:06:54] because a lot of late deliveries. And so it's like, OK, one interpretation of that is I've got to ship them through UPS. But what if I can solve both your problems? Costs and on time delivery.

[00:07:07] What if I can do that by picking a different carrier for every shipment based on what the cost or the on time delivery is? And nothing actually started to move the curve forward in terms of being able

[00:07:18] to get to not just better costs, but also better on time delivery through a different model, but you don't get through to that kind of solution. I think unless you're asking the right questions. That's one.

[00:07:28] I think a second quality that manifests I think how people with the entrepreneurial minds that approach the work is this idea of progress before perfection. This is an idea that's become widely accepted over the past couple

[00:07:41] of decades with your actual product development needs started, but things like that. It means one that you don't let unknowns stop you from moving forward, but rather you use those unknowns as hypotheses to text and use tournament unknowns.

[00:07:56] It also means being very aggressive and very precise about deciding what do we actually need to solve versus what can wait to be solved until later? That can be very difficult. I do think this gets kind of misunderstood often as justification

[00:08:13] for lazy sloppy words and well, just put it out there. The question was, what's also they want? Sure, the customer is the ultimate judge, but a customer is not going to sort of forgive a happy product because oh, we run an agile development process.

[00:08:26] You both might try to tell that to the customer, right? But really, it doesn't have to be slow. It just means that just like everything else about the start up, be resourceful and fast about using what you have available with data, whether that's

[00:08:38] hardly a preferred thing to think about potential failure scenarios. You just this idea that we are so decisive or you are so decisive about what's important to know and what's not. And you don't let the unknown stop you.

[00:08:52] I think in one way that's manifested at cold current is we made a decision very early on in our product development to focus first on the physical shipping outcomes before we really got into optimizing and fine tuning

[00:09:07] the user experience, because ultimately what job is our customer hiring us to do? They need their boxes shipped. And while we made our physically touch the boxes, they're entrusted us to make sure the right thing happened with those boxes.

[00:09:21] What matters is what happens to the shipments and that the work gets done. And a lot of us kind of come from environments where UX is very important and we have a lot of passion about that and should

[00:09:32] the steps sometimes and say, all right, well, we're going to focus on that later in our standard for UX is it just shouldn't get in the way. And now that we've got the foundation for the platform that the

[00:09:43] operations side of it really works and works very seamlessly and scalably. But now we've really shifted to say, all right, now let's come back to the UX and think about, all right, the day to day users of our product and how can we make their lives more efficient?

[00:09:58] How do we give them better information faster and in better ways and then self-service and things like that? But there was a decision to say one comes before the other versus trying to solve all of it at the same time because it's all

[00:10:11] in a part of the same product. And then I'd say the third before you get to your third point, I wanted to ask, I've seen a lot of people struggle with this point progress over perfection because they really are perfectionist

[00:10:26] and they're extremely good at what they do and they can't hold themselves to a product or the work that they do and see something either unfinished, leave their fingertips. I'm just curious, how does someone successfully deal with that type of situation?

[00:10:42] It is very hard to do in practice. And frankly, we're taught in school to be the opposite of this, right? Your job is to learn the material, complete your assignments and answers are right or wrong. And we're taught to be completionists.

[00:10:59] So we're taught to do the whole thing and it's very binary. Oh, biology is more important than social studies. So I'm going to focus most on biology and not going to redo me social studies. You can do that, right? But then you get penalized through a lower grade.

[00:11:11] We're disincentivized to do this from early on in our lives. So it is challenging. I think one thing that our team has done really well is we've really built a process around ensuring we do this. Our head of product here runs this great process

[00:11:24] where we get together every month. Let's call it better table. And for product ideas and priorities are accumulating kind of throughout the month and that they all get reviewed in conjunction with each other during this betting table process. And then we allocate points across and say, OK, well,

[00:11:39] this one's going to get five weeks worth of engineering time versus two, et cetera. And then that is the work that's then done the following month and it all watches before the end of the month. And so what that does is you just

[00:11:51] like we were talking about earlier with book is not the back end versus the front end. New user experience at first is it forces us to prioritize because at the end of the day, everything is important. People don't just create bad product ideas to the secret idea.

[00:12:06] Yes, yes, yes, it creates these ideas because they matter and they are important. It's what's so unabated, but it ensures that we're constantly forcing ourselves to prioritize as well as it keeps us focused on output and ensures that we are continually to ship features,

[00:12:20] that we are continually to not just talk about ideas, but actually publish and put things out. And I think process has been one way our team is you really come up with a good way of helping us make those decisions collectively and have that mindset.

[00:12:35] Because it's very hard because even so we're taught from birth essentially that this is not how the world works and all of a sudden you get into business and startups and stuff like, oh no, that's going to do it completely different. Right?

[00:12:48] I really like that idea, the betting table. OK, so I'm going to let you hit on your third point. Go ahead. The third way that I think an entrepreneurial mindset has shown up at Holdcard is people, team members, really seeing ambiguity as opportunity.

[00:13:05] And what that really means is sometimes there's a way that and this is the way things are done. And it's the opposite of that. It's, oh, we don't have a way to do that yet or there isn't a way to do that yet.

[00:13:15] And the people who I think kind of have these traits look at that as opportunities to take ownership to create, to build something worthwhile. And in many ways, just like we talked about with this idea of progress over perfection that this is also not intrinsically wired into us.

[00:13:35] Humans are biologically wired to fear ambiguity and to crave. There's a lot of good sort of biological reasons why that makes sense. Startups are entirely ambiguity because nothing exists yet. And so logically startups equal fear. And while the idea of being a startup

[00:13:55] and having a big sort of blank canvas to create all these solutions is very exciting, the experience is different. And it is scary and you don't always know what to do or there's no clear right or wrong answer. And a great example or one example

[00:14:11] like has really kind of shown itself in action is something that could have been very simple and kind of a chore which was that we got to a point in our company where we needed a CRM system to manage all the sales lead, the different sales conversations happening.

[00:14:25] And part of the answer to that is you're gonna find a tool so we went and decided to use HubSpot. But the other part of that's how you use the tool. A lot of companies will just take something like HubSpot and implement it and call it a day.

[00:14:37] Our team and it was really cool to go to watch this. You get almost like even though 100% or more you can see the energy kind of coming through through the virtual room, so to speak is that actually really saw that as an opportunity

[00:14:49] to really build a best in class sales machine. They're kind of like, look we can use this to make ourselves faster. We just hired our first full time sales hire but there was a lot of kind of just work with your R.

[00:15:00] Like how do we really make this into an advantage for us? And I think team in this case really saw this blank space and saw that as an opportunity to not just sort of hope the gap gets filled with something off the shelf

[00:15:13] but really to create and to define what do we want our sales process to be like? How can we move through these deals as fast as possible with this high kind of close rates as possible and a lot of great I think insights

[00:15:25] and kind of finding the discoveries just even came out of the process of doing that. And so I think that's an example of when ambiguity is opportunity and when people really see that. I like that you framed it as ambiguity as opportunity. I've heard this competency shared

[00:15:40] as dealing with ambiguity but I think you said it better. And when I first came across this competency when I was getting certified by Cornfury International's 360 Executive Coaching Report when you get that type of certification you're actually shown all of the statistics around each competency.

[00:16:01] And this particular competency I can tell you is the most challenging for anyone to achieve. It's like one of the top five I would say. And it's actually like one of the most desired. And so I think that there's a lot to say

[00:16:17] when someone works in a startup because startups are always known to have this ambiguous factor. And if someone can get through that I think it's really admirable to see that people can actually successfully view ambiguity as an opportunity. So I agree with you.

[00:16:34] I agree with all of the three points that you made which leads me to my next question and I wanna understand because knowing how important an entrepreneurial mindset is I'd love to learn what were the biggest hurdles you faced during the initial stages of hiring for your startup

[00:16:52] and how did you address those? Hiring the people to begin with because when you think about what does a startup look like at the very beginning I was a guy working out of my basement. There's no business, there's no product yet.

[00:17:06] I'm saying, hey, like we've got a lot of great equity we can offer you and one day this will be worth so much money but right now it's pieces of paper. And I think that because again especially these days people find the idea of startups very exciting

[00:17:20] but I think that in the hiring process people really do self-select and there are a lot of offers that I made before. Finally someone decided to join who's our CTO who is still with us despite having to work with me. It was interesting that you actually

[00:17:35] were talking about things like ambiguity, control, fear and things like that that go along with that that when I've made offers these people and we're really going through the process of they were going through the process of do I want to leave what I'm doing

[00:17:49] and do this startup. The amount of existential anxiety that came out in those conversations I mean so much more than hiring for role at a more established company or something like that because really it's like the type of risk that goes into joining a startup

[00:18:06] really gets into these sort of fundamental who we are as people and what is an archetype for risk and how do we sort of face challenges a lot like the entrepreneur mindset article is describing anti-fragile things like that and again not to say that people

[00:18:20] you shouldn't join on it therefore fragile no of course not but it's just a specific type of kind of risk and sort of challenge that you put yourself through and it's a G I even had one person who I'm pretty senior person in their career

[00:18:32] who deliberated for weeks on I really want to do this but I'm just not sure and the thing that ended up pushing them to not do it there's a big signal from the universe was that they just started remodeling their house yeah the cost of the house remodeling

[00:18:48] was the straw that broke the camel's back eventually really? well yeah they're like okay I do think this is an area where having multiple co-founders helps because then you're not the only crazy person that someone sees they see that there are other people

[00:19:04] who are also committed to the mission and in my case even though I was the only full time employee at ColdCard in the beginning I did have three co-founders who had exited startups previously and very successfully and one of them was the founder of Blue Apron

[00:19:20] which was the company that essentially created the perishable e-commerce industry that we sell to now at ColdCard and so I think this helped give us credibility and legitimacy that helped the people who joined us in the early days kind of get over that hump you know, strengthen numbers

[00:19:38] even last week I was telling our CTO Joe you know, as soon as you joined you de-risked this thing for everyone else by more than 50% so now it's not just me who they see who's crazy there's someone else who's bought into this as well

[00:19:55] and so each person who joined ColdCard made me just a little less crazy in the eyes of everyone else who joined afterward and they reduce kind of the risk for the next person and the next person when you reflect on your experiences are there any insights

[00:20:12] you wish you had gained earlier or actions you would have taken differently concerning talent and people related challenges? I think that's a question that in some ways never reaches a final answer because every specific person is different every specific situation is different and a lot of times

[00:20:35] you don't really know how effective something you did was in this regard until later but when I've tried to assess myself on the three dimensions we talked about based on things people have told me I've done better on versus worse on

[00:20:50] you know, starting with this dimension of why over what this idea that you abstract away from specifics and get to another level of why root causes, etc as someone whose Myers-Briggs personality type is very high on the intuitive and conceptual dimension

[00:21:09] for me it's almost easier to use an analogy than it is to say something specific and so I naturally get a lot of energy from this type of thinking and dialogue I think that at Cold Cart as a team we've been fortunate to

[00:21:25] build a team of people who are naturally curious who are high on critical thinking and generally not content to just accept the first answer they get if you listen to our meetings you hear a lot of questions like what are we really trying to solve here

[00:21:41] or you know, when does that matter and I think these types of questions that get to or help get to the root cause of different things you're seeing and where I have to challenge myself in this regard is to not abstract

[00:21:56] so much that what I say is too open-ended that it leaves too much room for people to diverge in what they take away and understand and that makes it harder to get to alignment later at the end of the day

[00:22:12] why is still a house to turn into what because we're building something and that's why we exist and so I have to find ways to check myself on whether I'm being specific enough you know, I always ask the people I work with

[00:22:26] to call me out if I'm not being specific enough or it's not clear what the action is I just have to remind myself to be mindful of that slippery slope very obviously I value rigor, I have a lot of questions and ask those questions in a way

[00:22:41] that doesn't either slow down the process or seem like it's slower down the process right and you kind of remember that is a slippery slope but I think having an institutional process helps but then also I think for any one of us

[00:22:55] everyone and start up as a leader so we're not going to play a guess like how we kind of ask those questions how it gets feedback and just kind of remembering that these things tend to get overly interpreted as too little it's a delicate artful balance

[00:23:08] is it, so it's kind of like this one I say even more in the other two are kind of more concept tug-of-war that you sort of have to keep pulling on to make sure you have the right balance across both and then in terms of ambiguity as opportunities

[00:23:23] so I'm an incredible weird person in the sense that I actually get a lot of energy from ambiguity that for me ambiguity is actually freedom and I know we're talking about that kind of positive sense of this discussion but really I'm refracting on war

[00:23:38] as maybe a person out of the father and I have or something but I personally I was volunteering in a food bank in Chicago where I was the other day and they give you this set of art follow these 10 steps to hack these boxes

[00:23:49] that we're gonna ship out and without even knowing of course I'm like I want to do that I'm gonna create my own process I can't even help process and I wasn't really aware of it and then when we came out they were like what all this short term

[00:24:01] of everyone else I know so and I think part of that's also like the learning or the thing that I had to constantly sort of hold myself accountable to is that remembering that I'm kind of weird in that regard and that most people have different levels

[00:24:17] of ambiguity, tolerance most people have different ways to deal with there's fun ambiguity with a player create structures some people just want to spend an hour talking through it and then that's how they kind of get comfortable with it

[00:24:28] I think as a team we sort of got each better knowing what each other needs and incorporate that into how we work almost self-contrasting at this point remember when I started out as a new consultant at Bain and Company where I used to work

[00:24:41] they kind of get all the new post MBA consultants into the same hotel in Miami from all the little offices every year and they do everyone change together and they do this exercise where they actually use a Myers-Briggs and you take your Myers-Briggs

[00:24:55] and see where your type thing is and they do this exercise where a facilitator stands up and says okay we're gonna walk through now and literally walk through an example project for a client and they're like okay and different things milestones happen in the project

[00:25:07] and oh, Clad just sent you one out of 10 pieces of data if you're at end, the intuitive kind take 10 steps forward if you're at end some of it's more sensory and concrete by nature take two steps forward

[00:25:19] and what it shows you is that different people get to the answer they get to the answer but they get there in sort of their own cadence and through the way they get there and the whole sort of moral of the exercise is that everyone handles ambiguity differently

[00:25:37] it's important that we are aware of that and consider that and build that into how you work together and for me too it's also some of these very much like well, one of the quickest numbers we can get oh that data exists I was probably 80% correct

[00:25:50] and someone, others on our team they were more like we really need a plan, a process and seeing how they had advantage and have the unity of making sure I'm also learning as much as I can from them going through that exercise

[00:26:02] the insight could come out of that and then also just ensuring that I'm building enough of that into my own process and the way I work with others on the team and I think you're really doing a fantastic job at Cold Cart having this reflective conversation

[00:26:18] on how these apply it's clear that this is why you're so successful and where you're at today so Jason thank you so much for your time and for being with me today and sharing with our listeners how to really cultivate an entrepreneurial mindset

[00:26:38] so thank you for being here Thank you so much, I really enjoyed this and appreciate it I guess I'll spend this time with you