I always say that startups are the wildest roller coasters. You can have your best day and your worst day oftentimes in the same day. You really need to learn how to deal with the ups and downs and accept that there are things that you simply cannot control.

Oskar Hjertonsson has been on a crazy ride for the past 14 years. Born in Sweden, he met one of his co-founders, Daniel Undurraga, in Chile, where they first created Needish, a marketplace where people could advertise what they needed, instead of what they were selling. Profitability was a big challenge, so they decided to pivot the company and renamed it to Clandescuento. The new business model copied Groupon’s, which only existed in the US at the time. After just months of operation, Clandescuento was acquired by Groupon, and Oskar and Dani led the expansion in Latin America.

They later took their entrepreneurial expertise into building Seahorse, a cloud based photo storage and sharing platform. But that didn’t quite work out like they expected.

In 2015, a 3rd co-founder who’d been working with them all along, Juan Pablo Cuevas, joined Oskar and Dani. From this partnership, Cornershop was born — launched first in Mexico and Chile as an on-demand grocery delivery service. In less than 2 years, conversations started with Walmart for a potential exit. The deal was announced in 2018, but after a long stressful wait, the antitrust authorities in Mexico ruled against it moving forward.

Having been on a similar journey myself, I’ve been exchanging personal struggles with Oskar for a while, and I’m excited to go deeper on some of his experiences here.

In this episode, we talk about lessons learned, his main takeaways on leadership and the emotional loops, dips, highs and turns that founders go through.

My name is Brian Requarth and this is Latitude 4 Podcast.

--------------------------------------------------------------------------------

Oskar

If I say the “F” word, can we delete it before we publish it?

Brian

Yeah, if you drop an “F-bomb”, first of all, it's not a family show, so it doesn't matter. And second, you know, I might have to excuse myself: I've got a potty mouth. So…

Oskar

That’s good to know!

Brian

So, hey, welcome to the Latitude 4 Podcast.

I've known your co-founder, Danny, for a long time. We met back in 2011, I don’t know if you know that.

We met at SxSW but I think we didn’t really start talking until maybe the last year. We connected through a mutual friend, Martin Schrimpff, and so I don't really know Juan Pablo, I knew Danny first. But you guys have been sticking together for a long time, building great stuff.

I want to start the conversation off with a WhatsApp exchange that we had. Just to get right to it, just to kind of get right to some interesting stuff, so… Don’t worry, there's nothing in here, you know, that you're going to be embarrassed about.

But I'm going back just I guess a couple months ago, to April. We've been chatting for a little bit and talking about, you know, we both were angel investors and some stuff, and we both I think share a passion for supporting founders, right?

Oskar

Yeah

Brian

So I remember early this year, I'm going to read you the message and it says: “hola! Regarding the way, we're back at the beach with the family. Regarding regulators, we will be notified on Thursday that COFECE sees risk in deal. We got a heads-up. By Friday I should have more intel”.

So that was April 28th.

Oskar

Last year?

Brian

This is April 28th 2019. Yes.

Oskar

So yes, last year.

Brian

I think most people that listen to this podcast are pretty informed about startups but you had this deal with Walmart, right? This was a year and a half ago essentially, right?

Oskar

Well, the deal with Walmart was like from 3 million years ago but this particular text was one and a half years ago. Many years into that deal.

I mean, that deal started a long time ago.

Brian

You started only a few years in your company, right?

Oskar

Yeah. So, they were a big partner to us and they approached us with the idea of an acquisition at a time, but it seemed like a good outcome and when we honestly were struggling to waste money on the private market. So it was a great deal. I loved the deal and we did the deal.

And then, from the time that hands were shaking, you know, and then you get the LOI and then the definitive agreement and then you file it with COFECE and then you wait for… Like, a lot of time passed. And it was f****** horrible — so that's your first F-bomb right there — because I'm not a patient person at all.

I know that patience is a virtue and I don't have that. I'm anxious and worried and I can't stand waiting. Particularly if the waiting is out of my control. It was painful. Honestly it was hard. It was a tough period. And it was a long period.

Brian

I responded with that fingers crossed and then your next text message was: “hi, I still can't commit to anything right now. Including travel. All focus on family. Just coping. COFECE MX antitrust has formally extended the period. It's all a shitshow. Family’s alternating between hotels and friends' places. It's not fun. Even if we get approval in May, I can't travel in June as all focus will be setting up new life in SF until new life is well-established”

Oskar

Yeah.

So we’ve made the decision to act on the signed and announced agreement as if it was a foregone conclusion, like if it was the deal. Because, you know, you read this on Techcrunch, or you read press releases that company A acquired company B and everybody's happy and there are exciting statements and bla bla bla. And then if you scroll way down, below ads and what not, it says “subject to regulatory review”. It never felt like a real thing going into that deal because of that experience and because our counsel, honestly, didn't see much risk in that deal.

So we announced the deal with Walmart I think in September 2018 and, by Christmas, we left Mexico. We put our furniture in a container, shipped it to Oakland and went to Sweden for Christmas and New Year's, and to get our visas for the US stamp in our passports, while we were waiting for this close of the deal — which would happen very soon, like in January. Or maybe February.

Our plan was to spend a few weeks In Sweden and then we were going to Chile, where we have our biggest office. I can work there, and my wife's family is from there.

So in Chile, it’s summer in February. So long so good, it was like a pretty decent plan. And the latest we would be in SF, in San Francisco, was like early March. But we thought it would be sooner.

And then this special period in our lives started. For a bunch of reasons, we ended up staying at friends' places and hotels in Mexico, Chile in Canada for 5 months, with two kids in preschool and school-age, waiting. And at some point, in the middle of this waiting, we heard that there was a real risk that the deal might not happen.

I was sitting in a hotel in Toronto and just kind of “I can’t cope with the waiting anymore and you're now preparing for 2 alternative futures. One is: sold the company Walmart, going to set up an office in San Francisco with Walmart. Great deal. We loved the deal. But at the same time, you know, the deal has almost happened for 2 years but it’s never really happening, so you have to prepare yourself for the alternative, that is: there might not be a deal.

And in that scenario you’re looking at a bank account which is running on fumes with the debts to Walmart — and not a nasty debt, a very very friendly, awesome… — Walmart has been awesome to us throughout this period. But we owed them operating capital because they were alone in the company money and doing the antitrust review, which is very common.

So we would end up with debt and no money or having sold the company. And it was still maybe a month out. And we stopped being in board meetings. The VCs were mentally checked out, obviously. Because I think our VCs said that in the history of their funds they hadn't seen such an early-stage deal being blocked by regulators, nobody saw it coming.

So we had to start reimagining like what would it be, to keep building and be excited about it. And at some point start to tell the team, some of the top people in the team, like “hey, by the way this could happen”.

And, I'll be honest, by then, our future as an independent company was looking pretty good.

So I didn't even know what I wanted, I think, at that point. It was like the end of April or May. I just wanted to know. I just wanted the wait to end, because it was torture. We couldn't really operate, we didn't have the resources that we were worthy of having, based on where we were as a company back then. It was never the idea to spend all those months with that little capital. Which couldn’t be adjusted either. The way the deal was made, how we had submitted to the regulator service, it was shit. It was horrible. Really horrible.

And then, at the end of the day the deal got blocked by the Mexican regulators.

Brian

Yeah, I remember when it did get, blocked and I read about it and I think you sent a link, you said: “only in Mexico…”, which obviously is not “only in Mexico”.

We’ve talked… I'm going to do my own antitrust — which we will leave maybe for later because this interview’s about you — but hearing you, it's kind of cathartic to hear someone that's gone through a similar situation. And we kind of bonded on that as we are both in similar situations. You’re through the other side of it and I'm still in the tunnel. I see light but I hope it's not a train kind of situation.

You know, what’s cool about that is that in that text exchange I wrote you “okay, I'm so sorry this happened, Oskar. It's complete and utter BS. You're going to rally and you're going to crush it and, we're all here to help you in any way we can”. And that was with a few other friends on the text chain.

And the bottom line is: it was a blessing in disguise, right?

And, by the way, I love the way that you responded to it, because you posted on Twitter — there’s an avocado behind you and so it reminded me of that — “Salió un conejo del sombrero regulatório... ¿Y ahora qué? Keep calm and order avocados.” I thought that was just like… Just amazing.

Oskar

Well, we don’t do a lot of PR… Like, we are pretty bad at PR communication in our company. When we do, it’s mostly for the internal audience. So that was really a message for everyone working for Cornershop and our partners etc.

Yeah, those days were insane. I was with my wife and the reason we were in Toronto is because we have had a waiting in Mexico, we couldn't go to the US before the deal had closed, I don’t remember why… Immigration, whatever .

And then we had set up an office in Toronto, which was going to be part of the deal with Walmart. We were still partners then, with Walmart. They were great partners to us.

So we just wanted to get out of the resorts in Mexico. People were like “oh, that sounds amazing”. And yeah, if you go on vacation, it is. Not if you’re waiting.

But still, that’s a better place to wait than many others, for sure.

So we’re in Toronto, just trying to wait. And every week we would think “this is the week!” — and they would add another week. Or another two weeks. So it wasn’t like: in February they would tell you “oh, by the way, you’re going to know in June”. It was like: in February they’d say “early March”. And then in early March: “oh, it’s mid-March”. Then it’s mid-March: “it’s April”. Then it’s April: “end of April”...

If they had told us “make no plans for your life until June, because this is going to take 4 months”, it would have been a different story.

So we were in Toronto and I’m like… I’m running 15K one day to cope, emptying the mini bar the day after. Kind of coping in different ways on different days and I'm not getting any work done. Refreshing stats and waiting and being angry.

I just also, to be super clear, I’m not some crazy libertarian, I believe markets should be regulated. I believe in the role of the regulators. I don't think that the time spent on these processes, I don't think it makes sense for young companies with limited cash, frankly. It just doesn’t make any sense.

So you know, that was upsetting, that was hard and our kids had missed school for 6 months. All that is on us. I’m not blaming anyone else for that. But anyway...

So then we finally got… So yeah, so the last week was the most, again, this has been like a horror movie, like, the last week was basically “okay, they have announced on their website that they were going into the vote. So COFECE is going to vote”. And not until then did I learn that we don't necessarily find out that day. That was the worst part because, first of all that’s new information because, I don’t know, I hadn’t asked our counsel, they hadn’t told us, or maybe they had told us and I didn’t listen. Who knows. Maybe they told me 9 months before how the process works.

But I couldn’t believe it: “what do you mean? They vote and they don’t tell us?”. “No, because after they vote, they write up the resolution and sometimes they give a heads up or post something on the websites… But sometimes it takes some time, — quote — to write up the resolution”. “How much time?”. And then our counsel said “well, it’s normally a couple of days”. And I’m like: “days???”.

Back then for me… Because I have waited for this … I think it was a Thursday the day they were doing the vote, or like a Friday. Thursday or Friday. And we knew that for like a week. So that week I was like “we have a date, now you can start relaxing”.

Anyway, I’m trying to make this long story short. So they go and they vote, so now I know that 8 people on Earth know. That was the most upsetting part of the experience. That 8 of these commissioners, these 8 people now know if our company is acquired by Walmart or if I have 30 days to find money for payroll.

And at the end of the day they knew, but I didn’t know. It just seemed so incredibly unfair. And just not cool, you know? And that’s a wild understatement about how I really felt.

So, anyway, days passed, the weekend passed, the Monday passed and any minute we will find out.

At the end of the day, all this is first world problems, obviously, we’re in a great spot, but it was tough.

And then we got the notice that they had… I got an email from the counsel saying: “no la aprobaran” or something like that. It was like a double negation. I didn’t really quite understand it. I had to read it like 2 times. And then I just yelled to my wife “they rejected the deal”. And I broke down crying for, I think, the first time since my second son was born. I just cried on the floor. Just relieved that the wait was over. Now there’s certainty. Now it's all up to us.

So that’s the story.

Brian

I think that the ups and downs of the startup life is just, like, I mean, they’re the wildest roller coaster, right? And the crazy thing about startup life, and I’ve been saying this a lot recently, is that your best day and your worst day are oftentimes the same day. Like, that's just how it is.

Oskar

Yeah, true.

Brian

In some ways, you were probably relieved to know the answer because of the stress, I mean. But you probably went in this thinking it was a done deal at one point, and then you started second-guessing it because of the extended period of the process.

How long did it take you to recover from that? Because you were leading from the front. I mean, you sent that message and then you had to rally the troops, right? How did that process happen from the moment you figured out? How did you address the entire company? What was the message inside the company? And how do you extend that message through your company when you are so physically and emotionally overwhelmed by it?

Oskar

I think I cried for, like, 2 minutes and then I was back to work. And also, to keep this honest, we had already lined up a convertible note from our existing investors. Because we know… Like, going into the vote,... our counsel told us: “we are going into the vote. And I don’t know”. Like, “I don't know”. And I asked him: “but what's your best guess?”. “We don’t know. They could approve it or they could reject it”.

So, obviously, we had had calls with our board by then and I knew that they were going to invest enough for a couple of months. And I had also written some communications for the team that was ready to send. Because, once they announced it to us, it would take like 2 hours for them to post on their website and then it was gonna be picked up by the press.

Brian

Yeah, You wanted to control the message, right?

Oskar

Yeah, I remember working on communications to rally the troops on the non-deal scenario, not knowing if there's a deal or not in the days leading up to this. I have that email, I’ll forward it to you, that I sent it to the team.

And then, you know, fast forward, everything that happened after has been great for the company.

Starting a company, part of it is about, you know, all right investors and value and all that. We're definitely, you know, we got lucky, at the end of the day, because we have grown so much during this process, to have this deal fall apart. And we were a much bigger company coming out of that process, and the markets were strong last summer. So we ended up in a better position.

Brian

Yeah, I mean, 2019 was an incredible year for Latam. Venture capital, Softbank arriving, dumping ungodly amounts of money into startups. It’s just that the market was hot, right?

Oskar

Yeah.

Brian

That is my reading of this too, but that’s probably not the thing you want to hear when you have all this stuff going on.

And I remember you actually told me something that you were still kind of struggling with this afterwards, right? Like, you don't just snap out of it. I’m sure you snapped out of it, got the team going, but I'm sure that there was subsequent repercussions of this, of the fact that this thing fell apart.

But I remember one thing you told me maybe 12, 6 months after the deal, even during the process, you guys were growing like crazy. I think you told me, like: “I don't feel like I was useful as a CEO at one point when we were going…”

Oskar

Totally useless. I was, like, useless for 6 months. Mostly useless.

Brian

It’s a testament of your team, man!

Oskar

Yeah. So then when we pitched the company... we immediately updated our B deck and slapped a C on it, tried to raise a C round.

And part of the pitch was that we came out of that stronger. Not only because we were a bigger company, with better economics, but also because we learned how well our baby was able to scale. Even without supervision or, you know, I just came out of that process… At the end of the day, the process was excruciating, but we came out of it very strong and convinced about what we were doing. And the team was amazing.

Brian

That’s awesome, man!

And then, here you are. A month ago, you guys completed the transaction. It all comes around.

And the timing couldn't have been better. Your business is performing super well. It’s probably super strategic for Uber now, given the certain climate we’re in. You guys brought it back around and you closed a deal that was probably two and a half, three times, larger than the original deal. Like a year and a half later, right?

Oskar

Yeah, so, again, the process was wrong. I don't think startups should spend that much time in those processes. I don’t think it makes sense. But the outcome is great in an absurd way. For us, not for Walmart. They always… When I tell the story I try to remember to make sure to mention that there was another part of that transaction that didn't get a better deal because it didn't happen.

You know, they wanted to buy our company, it would have been a great fit for them, so, obviously, it was very disappointing for them. And they were great partners back then.

Brian

Yeah, that's great that you maintain that relationship and that you have a commercial relationship now with them. That’s an amazing story.

And I’ve enjoyed our conversation because, as I mentioned, I'm going through something similar and it feels eerily similar in like “yeah, we’ll probably find out this week” and then it's like… So I'm supposed to like… But by the time this goes live on the recording of this — because we record these and we post it later — I'm hoping that like I already have the news.

Literally I’m supposed to know like in a week or two from now.

Oskar

You should expect three months. It’s better for your mental health

Brian

That my lesson I’m taking away. Like preparing my mind for this.

Listen, let’s go back a little earlier in your journey: I asked a couple… I asked a friend here that I mentioned early on, Martin Shrimpff, I said: tell me something interesting about Oskar, you guys are friends. What is something that I can ask you. And he said one of the most impressive things about you is that you made it big with Groupon. You know, Groupon to the IPO, you made great money and then basically you invested all into this new company, Seahorse.

Oskar

No, I didn’t invest it all. But I invested, you know, a significant amount, particularly taken into account that we didn’t get a salary for those two, two and a half, years.

Brian

But one of the things he mentioned is that, essentially, you made some money and then you were in a tough spot, because it didn't pan out. But bought some Bitcoin, right, during the time?

Oskar

So, a little bit. And that kind of saved, I guess it kind of saved me a little bit.

But, yeah, we were part of this Groupon IPO and, as I told you, I'm not used to talk about this publicly, but I guess the context…

Brian

I know. I know. For everyone that is listening: I had to twist Oskar’s arm during this conversation because he is like “I don’t do that. I don’t do that shit man”.

So thank you. Thank you for making the time and it's really… It's great. Because there needs to be more stories told about this stuff. And we’ve just talked about a success story, now we're going to talk a little bit more about the failures, because we all have them. And I think that startup success is romanticized, massively. I guess it's good because more people maybe jump in, but people aren't really psychologically prepared for the actual difficulty of what it is.

Oskar

I think it’s impossible to be prepared for... I think anything in life, either you’re an entrepreneur or not, whatever happens it’s pretty hard to be prepared for the big things.

But, yes, we… First of all, we didn’t sell all the shares from the IPO. After the lock-up expired, everyone that I know that likes me and that had more experience told me “don't be a f*** idiot. I know the shares are down like 50% from the IPO, whatever, but you're still up from that 0 basis that you had. Just sell it. Invest it in the market”. And we were like “no”, because we had just left Groupon, and we felt like they had shit together. And clearly they did not, by the way, I can’t believe I thought that back then. But we didn't sell.

That was really how we lost everything from that first exit. We didn’t sell the shares. I think the IPO had like, I don’t know, 38, 28... whatever, I think the lock-up expired at 13. And I think I sold my first shares for like 1 and a half or 2, or whatever. And then the cash proceeds from that deal… You know, inspired by Silicon Valley, together with Danny, we were like aggressive on angel investing in Chile.

I don’t regret it. Now. I did regret it a few years ago, because a couple of — I don't know much, but way too much money went into startups that I didn't really analyze much. I thought that was kind of a responsibility. And I think it is, in a way, still. Like, if you’re successful in Brazil or Colombia, it's still early days, but I think everybody is becoming angel investors. And I think it’s a much better time now for that than 2010. 2010 was way ahead of the curve in Chile.

But, anyway, so between that and our own failed photo app where we put a couple of hundred grand each, me and Daniel Diaz, and didn't have a salary and living, you know, building a family in SF without a salary for like 4 years. So yeah, it was pretty rough.

And I think that not having money is not a problem. Having money is not a problem. But having money and then losing it... That’s really where you don’t want to be.

It was stressful, because we had this exit when we were like 30, and then totally wasted it in 4 or 5 years and ended up being older with kids and, like, no credit because we sold our company to Groupon which turned out to be like the worst IPO ever.

So, whatever credit there was in that acquisition, I felt at least, wasn't worth much a few years later. I honestly don't think it was. I don't think I'm being paranoid or anything.

So, self esteem was running pretty low and that's when the photo app company in Seahorse failed, we shut it down in, like, Christmas 2014. We didn't have much left to keep living that life in San Francisco. And we're looking at “do I try to get a job? Who would employ me? And how would I enjoy that?” It was tough.

So I'm very grateful and happy that Cornershop has been a rocky ride but, at the end of the day, has had a great outcome. I’m very grateful.

Brian

Yeah.

And you guys, the 3 of you, this is like your 3rd or 4th thing together, right?

Oskar

That’s our 3rd together with Danny and 2nd together with Chaq. And he is the success factor. We’re 3 founders in the Cornershop. Me and Danny are more seen in the press, I guess, more known in the ecosystem. With Pablo Cuevas, a.k.a. Chaqueta, who was part of the first company and of Cornershop, since day one.

Brian

Yeah, and tell me about the balance of the, you know, I mean, you’re working together for like, I guess you and Danny for 14 years now and Juan Pablo… Chaqueta? Is Chaqueta his nickname?

Oskar

Yeah. Chaq.

We played soccer at the University when it was hot, and he was wearing a jacket even when it was hot and… Chaqueta, jacket in Spanish. I mean, jackets in Chilean spanish. It’s something very different in Mexican Spanish. I don’t know if you know.

Brian

Ok. (laughs)

Oskar

It’s spelled C-H-A-Q. And all the Americans when we are on call, think it's Chuck, like Chuck Norris.

Brian

Yeah, that’s what I understood. Nice.

So tell me about the balance of the founders' relationship.

I mean, it says a lot that you guys, you know, you've been a part of multiple things. That's a special thing when you figure that out. What's the secret to success there?

Oskar

Yeah, so, first of all, I’m not a solo founder. I don’t think I would never be a successful solo founder. I mean, I love having this team of three.

I mean we were trying to… One of the things I'm trying to do now is to kill the founder concept and kind of really use that context a lot less, because we're a bigger company and there are a lot of other people that are equally important at this stage so… But obviously earlier on, it’s a lot about the founders, we decide everything.

Yeah we have worked together since… So those two guys have worked together since 2004. They had a company before we had our first company together, a dev shop in university. So we’ve been working together for 14 years. I love them. They’re 2 of my closest friends and I have the deepest respect for them personally and professionally. And we fight all the time. Every day. About something. But it never lasts until the evening. Never. Not once. I think… I mean, seriously. So that I think is amazing.

Like, you cannot not fight with your co-founders. That means you're not emotionally invested in what you’re building. If you agree with everything, that’s ridiculous. And if there's no fights, well, somebody's being apathetic or lying.

So a lot of fights, but somebody always wins with a better argument. Like we don't have any nasty bouts, like two against one. We never had that either. I think we've never had a, let’s call it a material issue about anything. Which is kind of amazing given what it’s at stake.

I think there’s a deep kind of sense of shared, kind of, basic values. Like we are politically aligned, mostly, which I think is important, you know. Specifically given how the world is becoming more divided, I think. I think that's something you rarely hear, but I think that’s key.

And, you know, the way we view our role as an employer. Things like that… I'm not talking about, you know, “should the button be red or green on the app”. More like fundamental things that have to do more with values and kind of sense of humor, like, movies we like or whatever… I think there’s a lot of shared stuff there that makes it all work.

And then I think we have a respect for the other guy’s expertise — this is a ridiculous word but — I mean our three roles are very clear and distincts: I'm the CEO and Danny’s the CTO and Juan Pablo is the COO. And for sure I couldn’t do their jobs. They would probably do a better job doing my job. But hopefully there's something unique to the way I do my job.

And then I think we all know that together we're stronger. We’re equal part founders. And we kind of leave the other person alone in doing what they do the best. But we are there for each other, sounding boards all the time, like, asking all kinds of things and obviously in the big decisions: M&A, financing, etc. They're very much involved.

And I’m very grateful. Again using the word grateful, I don’t think I ever used that so often in a one-hour conversation. But, yeah, they’re amazing.

Brian

It's really a critical, fundamental part and I get what you're saying about it's less about the founders at some point.

When you're scaling a company your whole objective is to position people inside the company so they can take the burden and share the burden. And some founders I think have trouble doing that like when they get to, you know, they want to stay in front and center and… But I think it’s the only way to really scale.

What are your takeaways in terms of, you know, you've led a couple companies now with your co-founders, what’s the lesson you've learned about what makes a good leader?

You know, not just the typical kind of cliche answers, but, like, what is the thing that you can boil it down until like a balsamic reduction sauce? Like, what is it that really just grabs you about leadership, that is important in a startup?

Oskar

You read about startups which watched from the outside seem completely dysfunctional cultures that are doing extremely well, right? And so I can't speak for generally what I think or know about leadership.

I can tell you that, in our company, leadership is about being the best individual contributor in the area you’re leading.

So it’s not some kind “oh, thirty thousand foot view, the strategic alignment, pointing with the whole hand and whatever”... it’s “are you the best person doing that job?” So you run the area with 50 people doing their jobs. That’s how we look at leadership. We lead by example.

And your instant feedback, good and bad. We don’t do that… whatever, quarterly reviews. I can’t f**** wait to tell people that they did something horrible or did something amazing. I’ll do it immediately. And I want everybody on the team to do instant feedback so we can just move forward and kind of, rule out bad behavior and encourage good behavior immediately.

So I would say… That I think is just “no bullshit”. I think if you want to talk to someone about their performance and you’re willing to wait for a month, that’s just inherently bulshit to me. That is dishonest in some weird way. Some weird corporate dystopian way. Like “I have some things I should talk to you, Brian, but I’ll wait until our monthly review”. That’s it. And I know and I respect a lot of people who work like that. It’s just not for me. Not for us.

Brian

Super inefficient too, right? Like, what are you waiting for?

Oskar

Yeah. So great individual contributors. Like, if you’re running editorial, you should be a great copywriter. If you’re running iOS, you should be a good iOS developer. If you’re running design, you should be a great designer.

And then, staying on top of people. We worked for Rocket Internet, we sold the first company to Groupon, and it was powered by Rocket Internet, their international effort, so I reported to Oliver Samwer for a few months.

And they would send this handbook, the holy handbook of micromanagement. And they would say: “if you share this outside the company, you’ll have to pay a 1 million euro fine”. He would say on the cover of this 90 page-long deck about how to be the perfect micromanager. And some of that is frankly amazing. You stay on top of people. Make sure that shits gets done, right?

Just fast, people working in the details and lead with example and just honesty. I appreciate it.

Brian

Yeah.

One other thing I want to ask you about, this is a very specific question, but I’ve talked to a handful of people, about you, in different circumstances, your name has come up. And I remember someone describing you guys as having the best internal reporting they've ever seen of a startup. Which is very random question, but: is that a thing inside your company? Because access to data and information, is that something you are passionate about? How does that come to fruition? How do you make that part of your DNA?

Oskar

I don’t know if it’s true anymore, but it was definitely true I think in the first 1 or 2 years of this company. Because in our previous company, which we ran together, which became Groupon Latin America, it was a B2C ecommerce — a lot of sales reps, a lot of contracts, a lot of deals, daily deals…

And we learned too slow in that company that having your shit together really matters. And knowing every aspect of your business, really understanding it, all the KPIs and drives, customer growth, whether it’s new customers or retained customers, it really matters. So we launched with all that. A battery of reports, and alerts and daily reviews of KPIs, hourly alerts on Slack of a wild amount of KPIs…

I think for many first-time founders, it’s more like an afterthought. Like, you launch the app but it doesn't have a back-end yet, and if it doesn't have a back-end, it definitely doesn’t include reporting on the first version. So then you go out and talk to investors, and they ask about your cohorts. And you’re like: “shit. What’s a cohort?” That was our first startup.

So we really set out to be anal micromanagers of so many KPIs and so many intersections of KPIs, like, I think we did a good job there.

Brian

Yeah, I feel like a lot of early-stage founders, first-time founders, they don't really get that right. They don't really obsess about the data as much. If you have control over that and you have clarity over that, it’s something that I think is a fundamental part.

Well, that’s awesome. I mean, I talked to Andrew about you and he said that you're one of the most impressive CEOs he’s ever worked with, and that guy invested in...

Oskar

What?

Brian

He said that. He said that to me.

Oskar

He probably says that about all theCEOs.

Brian

No. I actually said that. I’m like “yeah, you say that about all the CEOs”. But he said then: “no, no bullshit”. He said that to me. He had you up there, man!

And there’s something about building a business in Latin America. There’s a lot of opportunities but there’s also a lot of challenges.

So it takes a skill set to build and navigate. A lot of things that you might not see in the US, difficulties that arise from, you know… Things like regulatory decisions and other things.

I love the candour that you approach things with. My observation is that it’s probably one of your greatest qualities as a leader.

So I asked you about the leadership thing because, in all my interactions with you, it's always been like really authentic. We got to the heart of shit when we start having lunch in San Francisco and we swap a few stories, designed also to make the other person feel a little bit better. And share a little bit of vulnerability and share the ups and downs of the roller coaster ride that is entrepreneurship.

So I think that what you do for the ecosystem is awesome, man!

Oskar

I really appreciate that.

One comment on that: first of all, just because of the comment from Andrew, I’m not thinking that he would ever listen to this but I really want to use the opportunity to thank ALLVP, Accel, JSV and Creandum, the 4 VCs that invested into our company.

They've been amazingly supportive for all these years. Andrew’s on my Slack daily, emotional sounding board, you know? Everything, from small shit to like big, strategic stuff… if anyone listening can get an opportunity to work with Accel out of Silicon Valley, or ALLVP out of Mexico, I strongly recommend both of those funds. The other two are less likely to invest in Latin America.

But on the honesty, I think it's true. I think we have a style of being very transparent and “no bullshit”. We call it “no bullshit”. So not being honest is kind of a fault “bullshit”. So it’s really bad for fundraising. That's what I wanted to say.

I think it’s just made our fundraising harder throughout the years. I was going to these meetings and I’d be honest about what’s not doing well. And we were bad at presenting our numbers in the best way or whatever. Seriously.

And I’m not saying that great fundraisers lie. Not at all. But that kind of projecting success and total conviction and security, like “we totally know where we're headed and there's no doubt” — that's not really how we built Cornershop.

I think there are benefits to that. I think it’s good for culture and team morale to see that you can be open about your insecurities, and you don't have to pretend or posture to be a leader. But it's bad for fundraising.

Brian

I like those businesses that step function, right? It's like: here we are. We're going here and we're going here. It's like it's very consistent in its rise. And the step-ups are nice but they're not 20X step-ups. And that is much easier to control, as a CEO and as a founder, because you're not setting this expectation, then all of a sudden you're dealing again with this crazy situation.

And it's funny you mention that about being honest about where you are. I actually was in Accel’s office in 2011, 2012, I think. I pitched Accel and one of the partners there asked me when I thought we would pass our competitors. I said “18 months” and it just was an unsatisfactory response. And they ended up passing on me and… It wasn't Kevin Efrusy who ended up investing later on, but it was a partner there and, ultimately, we ended up passing them in 12 months. I was conservative in my response. And probably, the investor hat, when they put it on, it’s like “oh, when they say 18, it's really 36”, you know?

Oskar

So part of it could be the timing itself of your answer, but also, consider this: I think investors just want a certain kind of alpha male mentality kind of person to invest in. So they're not really… It doesn’t matter if you say 18 months or 18 years, it's more like they want you to be like “we’re gonna f*** kill them”. Like, “what do you mean pass them? They are going to die”. Like, “who are they? Competitors? We don’t have competitors, we are unique”. You know what I mean?

Brian

If you look at the data, it kind of supports that, right? Women are much less likely to be funded, it’s a massive problem.

Oskar

Yeah.

Brian

And a massive opportunity for investors, because there are amazing women that are getting passed on because they don’t have the brashness that maybe the kind of type A male CEO has, that just thinks that they can't do anything wrong.

Oskar

Yeah.

I wonder if that becomes a self-fulfilling prophecy, when most of the people who get funds are those types, so then people think that those types are better at building companies.

But when we've pitched Cornershop and haven't done well, I’d think “how is it possible that these other companies are raising money? I know their metrics, I know their apps. And we even raise a third of our valuation, or whatever…?”

It’s been a frustrating part of our journey, for sure. And I think that I'm to blame for part of that, for sure. But it doesn't mean that we’re less aggressive or that we want to win any less. It's just that we projected differently. So, anyway, that is for another podcast I think. We could dive into that.

Brian

Yeah, but one thing that happens is if you build a track record. At that point, it doesn't even matter anymore.

Oskar

Right.

Brian

You get to a point where it’s like “ok”.

Oskar

But you get there though, I think it's sad if only super alpha males are invited to… And clearly it’s not only super alpha males. Because I know a lot of really nice, friendly entrepreneurs like you, but I think that… Anyway that’s a different discussion I guess…

Brian

Yeah, but I like the perspective about it. It’s interesting and there's a lot of psychology that goes on, right? In this whole investor game and…

Oskar

Huge! And this is F.O.M.O. It’s creating F.O.M.O. It’s all about creating F.O.M.O. And I was way too old when I realized how that is done, you know?

I got to send the deck to 50 investors on the same day and make all of them believe that someone else is writing the lead and you got … It’s like mechanics, almost.

Brian

Yeah.

Oskar

It’s much more science than art, for sure! And I always underestimated the deck.

We were like “marketing last” as a company. In many ways. We really are. Today we discussed: we don't have an “About us” on our website.

I mean this is just the base… it’s a weird thing, I think, about us, that has to do with not being PR kind of marketing.

When I say “marketing” I mean external, outside the product.

Inside the product experience, I think we are pretty good at the marketing. Our bags, our copywriting, and all of it… But outside the product experience, we suck!

So I think our decks, our fundraising... We would be like “oh, we are going to start fundraising on Monday and we’ll do the deck on Friday”. Because they’ll love the data, because the KPIs are good.

So I was always like “well, if the KPI’s are good, they're going to see that and they're going to get it”. So in a way, it’s very arrogant.

Brian

A bit naive, maybe, too.

Oskar

Oh, well, naive/arrogant. That’s a good way to put it.

Brian

But the funny thing about that is: that is a little bit more true, I think, in a growth company. That the metrics become more important. The story is so fundamental in the seed, the pre-seed, the series A…

And the problem is: if you're unsuccessful at that, you're almost seen as this pattern of a company that if you're not nailing it from the beginning, it's like you very rarely all the sudden, like, “oh, we have this other big story now”.

It’s almost like it needs to be designed like that from the very beginning to set you off on a track.

Oskar

For sure. Hopefully, that's what you’re helping your companies with. If you look at the YC companies, they’re great at fundraising. That's really what they do, you know?

And that’s very, very valuable. I think I still probably don’t quite appreciate the importance of that.

Brian

I would take a kind of hustling CEO/founder that's able to “GSD”, get shit done, and make it happen a hundred times out of a hundred times, over someone that can just tell an amazing story.

But unfortunately the person that can tell the story oftentimes gets the investor’s love.

Oskar

Yeah, and it’s fair. It is fair, but it’s… It’s interesting.

Brian

Well, you mentioned your investors… When you first started out, I guess, you know, going back to 2007, there's no funds, right? Like who's investing in 2007 in Latin America?

Oskar

Well, luckily Wences Casares was. Do you know Wenceslao?

Brian

Wences is an investor in my company too!

Oskar

Of course! He is in all the good companies in Latin America. He must be one of the most successful angels down there.

So he really was a key to us. Like, if I look back, luck is such a fundamental component of our entrepreneurship journey. The way that randomly Wences replied to a cold email that Danny sent to him. Because I think Danny went to the bathroom in someone's office and saw a magazine you could read… — Maybe it was not the bathroom, it doesn’t matter, but — Wences was on the cover of that magazine and Danny was like “oh, man! That guy! I remember him! I’ll email him”. And he knew someone who knew someone who had an email that was maybe Wences’ correct email.

And Wences replied! That’s just such a random thing!

Knowing Wences now, it’s not that random. I think he’s amazing!

Brian

I think people will be listening to this and scanning the internet for Wences’s email address.

Oskar

Right. Maybe!

So he invested in that, later he attracted a few other angels and Chilean businessmen. But also family and friends, like my mom, Danny's mom… And our first round was $500,000.

Brian

Yeah, I guess that’s Wences signal, right? Like, something that Latin America lacked particularly back then is having someone that had like a reputation back you. It was an instant way to help you.

And Wences has that signal. Because he’s been part of a success story and had tons of experience in investigating and as a founder.

SoI'll tell you a quick story about Wences, real quick, because this is kind of a funny story: so a couple of years ago, I reached out to Wences as I was trying to think about my next thing that I wanted to do. And I said: “hey, Wences, I'd love to get together with you”. And he responds with “yeah I'm in Argentina. I'm down in Patagonia for the next nine months. So it has to be when I'm back” And so I literally respond to him with: “can I come visit you there?” and he responded back: “you want to come all the way down here?”.

And so I literally bought a ticket to fly 4 days later. I flew to São Paulo, stopped in my office and then I caught a ticket all the way down to visit him and I had a scheduled meeting with them. Like “I'm going to meet you on — I think it was like a — Tuesday, in the afternoon.

Oskar

In San Martin.

Brian

In San Martin de Los Andes.

Oskar

Yeah.

Brian

I was in Buenos Aires. I was almost there and I stupidly missed my flight. I missed the meeting.

So I literally just traveled for like 24 hours and had one more flight, and I’m like: “I’m just the biggest idiot”. And so I ended up buying another ticket to Bariloche and then I drove from Bariloche. I was looking at crypto and looking at all this other stuff that I wanted, just to pick his brain.

And so he ended up basically saying “hey, don't worry about it. Just come anyway”. And I joined him and I had dinner with his family and all their neighbors. It was like a meet-and-greet dinner with all his neighbors. So I was the totally awkward guest that had invited himself. I sat next to Bel, his wife, and they were the most amazing hospitable people.

Oskar

Yeah, they're so cool. We were there at a barbecue a few weeks ago with the family. So he invited me and Danny — first me alone, and then me and Danny— to stay at his house for like a month, outside Palo Alto in 2008. For a month! And they had young kids. They’re the coolest.

Brian

Yeah. I rolled up and, like a gaucho, he had a gigantic blade on his hip, you know? The guy is legendary.

But,I think the key thing here is like having those early people that take a bet on you, right? And you probably were inspired by him and others that supported you when you made all those angel investments, in 2010. You were probably just like...couldn’t have done this without the support of someone like Wences. Mickey was like that for me, who is his business partner, and others. Many others.

Oskar

For sure!

That’s what I said: I think it is a responsibility. I think that we are doing it, maybe, a bit irresponsibly. But it’s nevertheless a responsibility.

I mean, everybody who had success in the market should invest part of their proceeds. It could be time. It doesn’t have to be money. But significantly add back value into the ecosystem.

Brian

Yeah, I fully agree.

That’s kind of what I want to dedicate the next 10 years doing. Latin America is an amazing place and it's been amazingly good, I think, to both of us.

Oskar

Totally.

Brian

There’s something special about it, right? I mean, having lived in multiple countries…

Oskar

Yeah.

We live in San Francisco now, which we love. But we miss Latin America, we miss Spanish and the culture and how everything is later, dinners are later, you wake up later and… I don’t know…

Brian

Well, listen, just kind of coming to the end of the interview here: so you got this deal with Uber now and I think you said “por la primera vez tenemos capitalización para poner en marcha proyectos”. So what’s next, man?

Oskar

Yeah, so, we are doing things that the world will see. (laughs)

I don't know if they're that exciting but there are a lot of projects on different fronts.

One, we announced a couple of weeks ago, a big partnership with Cencosud, one of the biggest groceries in South America. And we had a lot of calls with them, now it’s a pretty big deal. And we are going to build dark stores together. That's very exciting. And, kind of expand our business model. And something that we will hopefully do with other partners soon, in other markets. So that’s fun.

Brian

For the people who are listening: a dark store is basically when you have all the supply of all the goods, and then you basically order it online and it gets brought to you. Kind of like a dark kitchen, but dark store.

Oskar

Yeah, I mean, it’s basically… So, the size of Cornershop in some of the mature markets is to the point where it becomes a big problem for the stores, because there's too many independent contractors in these stores competing elbow to elbow in the aisles with food traffic. So the retailers would rather prioritize their food traffic, which makes total sense. So the idea is that you move the ecommerce picking operation into dedicated hubs. Dark stores is a bad name. Call it “ecommerce fulfillment center”.

But that is not that different from a supermarket. It has a lot of thousands of products and it’s in an urban area, but it doesn't have to have all the fanciness and the perfect location for a kind of food traffic store. So they should have benefits. So we’re working on that.

We're also allowing ourselves to invest in some projects that might or might not work. Nothing crazy, but just, you know… That's what I meant with that tweet. We now have time to build things that might not go live until 6 months from now, and that might not be very impactful. But it's okay to dedicate a few people to work on that for a while.

Brian

When you’re running a company and you're also under the gun financially and you've got this kind of competitive landscape, it's hard for you to think super moon shot, long long term.

Oskar

Yeah.

Brian

Do you feel like you're able to do that a little bit more now?

Oskar

Yes, exactly. Totally.

So, moonshot, I don’t like saying “moonshot”, because I think of Google’s moonshot, which is flying cars or whatever... Like we are not building any flying cars, we don’t have the capital nor the ability, I think. But definitely…

Brian

Long term initiatives, right?

Oskar

Long term initiatives… Right now we're in the process of repurposing some of the core, the core team, to be working on, not the day to day stuff. So to let the second generation of the core team kind of take much bigger responsibility and to shift some of the very very core people, including some of the founding teams’ time, to projects that will see the lights in a couple of months and that are, you know, bets. In slightly different directions. Not necessarily super intuitive to what we're doing today always. Leveraging everything we built, you know? We have stores and shoppers and brands, and retailers and…

It’s super fun. I consider this… If we forget about the whole homeoffice thing — which I find depressing. It’s not for me. I like to work together with people. But — other than that, this is really a honeymoon of the startup that I’m experiencing now.

It’s the commitment and the speed of decision. Seeing it more as a hobby than a job for many people in the team of a startup with the resources of a big company.

I never really experienced that, so that's kind of a dream, in a way, come true. Like, really.

And it's also a little bit mind blowing and it’s kind of big. Now we have 1500 employees, tens of thousands of contractors shopping on our platform actively. So it’s a big responsibility and we can really build something very meaningful and everlasting.

We can also totally f***** it up. And that's the challenge, right? That's what makes it fun.

It’s a happy time for Cornershop for sure.

Brian

Listen, man, this’s been a super enjoyable chat. I super appreciate the conversation and thank you for sharing your story. I know that you hate this stuff, you know, you kind of don’t like to be public with all these details, but I think it's great for the founders to hear it. And it's motivation, because you were knee-deep in shit at one point and then you figured out how to get out of it and now you're kind of on the other side of it.

So I think that people need to hear those challenging stories and it gives a little bit more, you know, kind of hope for the founders in the tough moments. And resilience is like at the core of what we have to do as founders.

Oskar

Thank you, bud. Really appreciate it.

Brian

Thank you!

--------------------------------------------------------------------------------

Thank you for listening to the Latitude 4 Podcast with Oskar Hjertonsson, co-founder of Cornershop! Each week we’ll be talking to great founders and investors like him, so be sure to subscribe wherever you listen to your podcasts and check out latitude4.com to find out more about the Latitude 4 Fellowship Program. I’m your host, Brian Requarth. Until next time!