"Stop Being the Bottleneck" Oddbox Founder Deepak Ravindran on scaling yourself as a leader

0:14Deepak Ravindran:Hello and welcome to the Tomorrow Brands podcast where we explore what it takes to build a brand of tomorrow. I'm your host Ruth Vitok and today's guest is Deepak Ravindran. Deepak co-founded Oddbox, the UK's leading ugly produce subscription service and scaled it from a Churchill side project to a nine-figure valuation in under a decade. But the real story isn't the growth, it's what happened to him inside of it. In this conversation, Deepak talks honestly about what hypergrowth actually feels like from the inside, becoming the bottleneck in your own business, the Sunday dread that can creep in at Series B, and the moment he realised his leadership style hadn't kept pace with the company he'd built.

0:48Deepak Ravindran:Now working as a founder coach, he helps consumer brand founders scale themselves, not just their businesses. This is one of the most honest conversations I've had about what it really costs to grow fast. Let's get into it. Hi, Deepak. Thanks so much for joining us today. Before we get into it, I'd love to hear your background and the origin story for Oddbox. So I essentially cut my teeth in finance about 25 years ago, working in corporate finance at the start. And then I moved to investment banking until about 2015. I had this epithynic kind of moment where I went not really happy doing what I was doing.

1:21I didn't have any purpose. I was working on a capitalist problem, essentially trying to make rich people richer, really sit well with me. And essentially, I decided to quit, to follow my passion, follow my purpose. And as you do, it was either going to be food or fitness, still my passion areas, and something with purpose underpinning all of that, either social or environmental of some sort. So as you do, I removed my investment banking suit and I became a personal trainer running boot camps in Clapham Common. And as I was doing that, my wife, Emily and myself went away to Portugal on a holiday.

2:01And if you went to Portugal, you come across these local street markets that are absolutely amazing. In one such market stall, we came across an ugly, viciously ugly looking tomato. It tasted absolutely delicious, but it looked really addly, lots of scars. It's this big, big red tomato, lots of scars. We would have never seen something like that in a local Sainsbury's. And so we said, what was going on there? Why can't we find, why do the tomatoes taste a bit tasteless in the local Sainsbury's? And two, why are they all perfect in plastic packaging? And so that piqued our interest, curiosity. And then we went to a bit of research when we came back to the UK.

2:42we came across the problem of food waste that happens at a farm level. Essentially, 20 to 40 % of produce that is grown for human consumption never mixes outside the farm because of size, shape, color, or because there's surplus to requirements. And what that means is they either get sent to animal feed, landfill, or juicing, or one of those kind of low-income propositions for the farmer, and that leads to food waste at a farm level, which then has a direct impact on climate change. And so we thought, you know, naivety, we said, surely we should, A, you should do something about this big problem.

3:20And surely a fruit and veg business from the farm to people stable should be easy. So there was a lot of naivety there thinking fresh produce business is easy. Little did we know how hard it was. And yeah, we did a bunch of research. we saw that there were companies that were doing something similar elsewhere across the globe. In the US, there was companies like Imperfect Produce and Misfits Market that essentially had this direct-to-consumer model working directly with growers and bringing fresh produce in sort of a wedge box kind of scheme to people's doors. And that resonated with us for two reasons.

3:59One, as I said before, naivety, we thought, how hard could that be? We didn't realize how hard it was. And the second was, we thought it was a great opportunity to use the box as a medium to tell stories about what was happening with the produce. So if I converted that hail-damaged apple, say, to juice, we kind of lost that story. But if I showed you the hail-damaged apple and said, look at that hail-damaged apple, that cost the farmer had to lose 50 % of his orchard. He couldn't sell that to supermarkets. That's a more powerful story. It resonates with consumers and something that resonated with us deeply, which kind of comes down to building a brand and what really resonates.

4:46So yeah, that was the kind of, yeah, origin story, I suppose.

4:49Deepak Ravindran:Amazing. I love it. And I love anything that makes us people, consumers think more about where our food comes from, because I think we're so separate. It's a great point. don't reflect on it at all there's so much we could talk about but what I wanted to talk to you about today was hyper growth because I know this is something that you've talked about publicly before because obviously I think Oddbox now is very well-known brand you just talked about the origins there was a period there where you grew incredibly rapidly right you went from 25 to 100 people in 12 months and I'm sure lots of other things grew as well.

5:29Deepak Ravindran:Talk to us about how that actually felt because growth is good in business, growth is good, but it doesn't always feel that way. For sure, yeah. Let me set the scene here. 2016 is when we started the business and year one was us working from a local church hall because we didn't have money for a warehouse and then growing on from there. Then we started moving to a shared warehouse, from all car to a zip car, zip van. So we'd seen the business evolve many baby step by baby step because we didn't have money. And then in 2020, obviously the pandemic was a terrible period for many businesses. But for us, demand exploded, went through the roof.

6:11And at this point in time, year four, we had about 8 ,000 weekly subscribers. And we went to about 50 ,000 subscribers in six months. We did that without spending any money on marketing. And we were based only in London. So all of those customers came purely from London simply because we didn't have the operational capacity to service all of the UK. It's crappy. Operationally, the supply chain was creaking, but the team did a phenomenal job responding to that. And then I suppose we had to take down the website for three weeks, which was unheard of for a startup to stop the website because we just couldn't handle that.

6:50So we took that three weeks to really take stock. Again, you always say luck kind of happens. You create luck along the way. But three months prior to all of this, since the Feb 2020, the first lockdown, we had just outsourced our packing to a co-packer based in Ken. And this was in progress. Half of it was in our warehouse. Half of it was there. Just all work in progress. The team just did this kind of magic job of, A, working remotely, and be just bringing all that together to help service essentially what six times, seven times in six and seven months, unheard of. And I think, and this is a phenomenal period, literally 25 people at this point in time.

7:32And that rapidly, A, the team was doing what 100 people should have been doing with 25 people. Yeah, it's just a phenomenal period for us as a business.

7:43Deepak Ravindran:You've said that the way you lead at 500K won't work at 10 million in terms of revenue, what specifically breaks when you pass that point? And what did you have to unlearn about yourself as a leader? Yeah, so multiple things break, by the way. So it's just one thing, but I won't talk about all of them because some of them are mostly tactical. Your operations break, your technology break, and so on. What I want to focus more on is the human side of that equation because it's less spoken about, right? We all bandy the successes that we have as founders, entrepreneurs. the human side is less spoken about because somehow feels like you shouldn't be talking about that as a week, but I don't mind saying that.

8:26So at each stage of the business, your identity evolves and has to evolve from an individual contributor and you just rolling up your sleeves and getting everything done to then a manager of a small team. And then essentially you can have a part manager team, you're a part operator, you take on a few areas where you haven't recruited for, and then from manager to a leader of a business. And this leadership happens as you scale and as the team grows as well. And for me personally, what stopped working for me was being this kind of scrappy operator in a business that then needed a much clearer a leadership system.

9:09Before I was just doing getting the job done and setting the standard really high. But then now I had to convince not just my direct reports, but their teams as well and bring them along the journey. And the biggest thing I had to unlearn was assuming alignment, when too much of the decision-making logic was still in my head. I was just this kind of ideas lead founder, just throwing ideas at the team and then assuming that they would just get it because I said so thing. There was a bit of that kind of, again, naivety in that equation. Whereas people, smart people, and we were hiring extremely smart people, they will belong, buy into that journey.

9:47They need to be bought in. And you can't just say, do it because I said so. That just doesn't work. And so a lot of time, I have to roll from explaining the what and the how to more explaining the why and the what, And then letting the team come up with the how and letting go of some of that control, letting go of the fear of what if a standard slip or what if we start moving too slow? What if things break? And all those kind of doubts in your head to say, well, here's the why. I wish it's clear. Now you go work out the how. I'm happy to support you in the best way you can kind of a thing. Because that was the biggest shift for me.

10:29Deepak Ravindran:You mentioned sort of those different stages and those different roles you have to take on as a founder, but equally you're moving at pace and there's no one saying to you, okay, and now it's time that you step into this next role. You're having to figure it out as you go. How was there anything? How did you do that? Were there any, when looking back, was it talking to other people? Was it mentorship or was it just very instinctive building the plane as you're flying it, as we say? Yeah, it was a bit of everything. Some of the learning happened on the back of things breaking and getting feedback.

11:07So for instance, example is exit interviews where people leave and they say, ah, as a founder, for example, the feedback I got from someone who left was the founder should just let us get on with our jobs and assume less controls. That's one piece of feedback that you get. the second piece of feedback you get again is as you raise investment you start becoming and especially from institutional investors you start growing from this really scrappy okay now i'm doing everything on my own with the ultimate responsibility in the business to then okay we get some angel investors who can i let us get on with it with a bit of input and then to an institutional investor you start having a formal board now board meetings things get structured, things get questioned.

11:53It took me a long while to understand that and land in my head that once you raise that level of investment, you become a salaried person in your own business. This is a hard concept to grasp and it took me a long while to get this around. This is the business I started with my wife. Essentially it was a family business if you will and suddenly we had grown to this massive team, ESB investment and I think And you get feedback. And the feedback can be pretty brutal. One of the feedback I got from Series B investors were, what's my role? And that was coming through a chair. That cost a lot of friction.

12:31And that's the other bit. Which all this feedback then meant that there is discomfort. And you can start feeling, I wouldn't say resentment, but start feeling disengaged, fear, and essentially leads to disengagement at some point. which then made me start working with a coach who then helped me. She helped me, A, understand what is important to me, what are my strengths, but also surfacing my blind spots through a 360 degree kind of care review. And I think with all that knowledge is how I, okay, now I understand I need to be a better leader myself because I work on self-leadership first before you lead the team because otherwise, yeah, you're just trying to be this leader without any L &D budgets, without training, which all the big corporates equip you for, right?

13:22That's the best part about working for a corporate is they kind of train you. But as a startup, you don't have the budgets, you don't have the time. You essentially are learning everything on the job alongside several other things as well. It's extremely hard for a founder.

13:36Deepak Ravindran:And you mentioned you went from it being like a family business to feeling like a salaried employee, almost like it's shifting from your business to an organization that you play a role in was that were you aware that shift was happening or did it come as a consequence of the series be raised that you weren't necessarily prepared for yeah i think it was happening because we were growing so fast i think every week every day became a lot of our survival and doing stuff executing executing whilst trying to keep up with the pace of other team which is growing they need more communication now they need to be brought on the journey and I think also when you start seeing your initial team they get where you're coming from they move at the same speed that you do like the business to move but then you also realize that you can't be the you can't all decisions can't come through you, you start becoming the bottleneck because there's only, and you can see, I would see slacks just racking up.

14:40There's so many slacks all waiting on my decision or Emily's decision. I'm going, that's not the way I'm becoming the bottleneck here. And so when you start seeing several things falling out of place, in other words, that's when you start realizing, I mean, I'm in an organization now. It's not just a scrappy startup but there needs to be structure and processes in place whether that's one-to-ones or bringing the team along that journey sharing what one part of the team does to another part of the team because that has an implication how does that impact the customer how does that in all these different things moving parts you become the kind of you have to bring them together or at least lay the foundation for them to speak to each other otherwise it becomes people stepping on each other's toes and essentially you being in the backseat just trying to manage it all.

15:31So yeah, I think that's when you realize, okay, now it's an organization, a clear-off chart, and that means more structure, more communication, yeah, and a bit more rigor around the decisions we make as well as a business.

15:43Deepak Ravindran:Looking back now, because hindsight's a wonderful thing, do you think it's ever too soon to bring in that sort of structure and processes? Or do you think there's like magic in the early stage where you're just doing or should that be something that people are looking to bake in from day one? I mean, if you want to give a cop-out answer, it depends. I'd say too much structure can slow you down as well. That's what happens in corporate is what used to frustrate me in a corporate. And I think there's a balance to be struck between lots of structure, lots of meetings. Like meeting is a perfect example.

16:16You can, today, the biggest problem with the workplace today is meetings. It's more of a block than an enabler. So to answer your question, I think structure is important to a certain degree and at a certain stage of the business. It is important to, for instance, I strongly believe that the old adage of, oh, business is 1 % idea, 99 % execution. I don't believe in that. And I explained to you why. I think it misses a big point about planning and visioning and thinking about the future. So I, for example, my advice is always for the founders is spend 20 % of your time on strategy and the vision and the future, thinking about risks, thinking about opportunities and so on, don't just spend your time execution focused.

17:00That's a structured block in your calendar, which is important to have from day one. So don't just go into the execution mode that most founders do because we're all good at executing stuff, doing stuff, getting shit done. That's great, but don't forget to take a step back and evaluating what does success look like? Otherwise, we're just all running like busy fools.

17:21Deepak Ravindran:At some point within all of that rapid growth, you're managing lots of stakeholders now. So investors, board, fast growing team, still doing a lot of the execution. What was the hardest part of holding all of that together? Yeah, I think when you have, so you've got investors, you've got team and you've got customers. I'd say those are the three main stakeholders, if you will, in a business that is scaling. I think the hardest part for me was holding this kind of external confidence. and internal clarity at the same time. Investors are always constantly pushing you, over-indexing on growth, and they want visible delivery.

17:59They want you to move fast. The biggest challenge that investors always had for us was you're moving too slow. Could you move faster? At the same time, you're also balancing this friction internally for the team around what are the priorities. Again, the why is clear in your own head, but not clear to the team. That gap catches with you very quickly. So it's constantly making sure what is important right now and why is it important. And you're constantly bringing your investors and team on board. Because otherwise you can be this typical syndrome of managing up and managing down. And you shouldn't be having this when you're running your own business, but you do if you don't manage it carefully.

18:40So I think that's where biggest friction lies.

18:43Deepak Ravindran:You've been very open about the fact that you burn out at the end of this experience. What did that actually look like? And when did you know something wasn't right? Yeah. So just for context again, Series B was in 2021 after Series A. We didn't want to raise money, but we essentially had investors knocking on our door. Peak of the DTC, boom. We had a nine-figure valuation with our script. And then the slowdown started in 22. The war in Ukraine, cost of living crisis. So we were seeing costs going up, raw material costs going up and demand falling, which meant this essentially cash problem, cash running out, nine-month runway and all these kind of.

19:28And nine-month runway, that meant that a couple of things happened. One was investors had invested on this massive high of a valuation and we're seeing this tank over, essentially over a year. there was a lack of trust and we went from literally four board meetings a year in our series 8 2020 to 12 board meetings a year in 21 22 huge shift right you're running a business and you're running board meetings every single month alongside that we also realized that on the cash position we had to let people go and so we had to let 40 percent of a team go it's a huge thing that for me was one of the hardest thing i never let people go before and we were this really small scrappy unit not that long ago and here I was seeing people join on Zoom.

20:16I didn't know a lot of their names when they joined this kind of new team 100 people strong team and suddenly all of these things were happening at the same time. The business was slipping under our feet. Investors no trust. They let people go and all that meant really was I was questioning essentially what is this business that we've built. I didn't set out to build a big business for that. I didn't set out to build a business where we had to let people go because I'd watched all these things and corporates in the US and all of this is very normal. And it's not like this is business, right? It's this business that people go.

20:48And for me, I think because I'd never done that before, I just thought it was a very inhuman thing to do, especially as a mission-led business. Part of it was like, where did I go wrong? Did I let this come to this kind of situation, this stage? What could I have done differently were the questions that would essentially keeping up at night. And then that would lead to this Friday, cut the laptop at 4 or 5 p.m. It's done. And then slowly your relief on Friday and Saturday and then fear on a Sunday afternoon. Yeah, I remember taking my five-year-old daughter to the playground and just standing there thinking this dread, this killing of dread that treats us on a Sunday afternoon.

21:29Go to office on a Monday. That then the dread becomes leads to a sense of disengagement. I'm looking forward to Monday. And then the fundamental thing in all of this is that I've always believed that when you run a business, you can look at, you put choices, right? You've got an option. You've got to look at business through a lens of fear and risk, or you can look at a business through a lens of opportunity. Now, the best business people balance with both. They don't take unnecessary risk. They take calculated risk. I think for me, because of all what was happening externally, I was looking at the business more from a sense of risk and fear and looking at it less from a place of opportunity and growth.

22:14And that's when I knew, well, everything was protecting this thing that we started from scratch rather than thinking about how do we let it flourish and thrive or just survive. So yeah, I think that's where I'd say it was burnout central, where it's fear, it's disengagement, and essentially starting to look at things from a place of, yeah, fear, rather than love and opportunity and growth and sunshine on winter and yeah, all of that.

22:43Deepak Ravindran:So what happened next? So two things happened. We were on holiday in Vietnam. I was there, but I was not there. Physically there, mentally not there. and essentially we were having this conversation with our then chair and she was mentioning that we have all these roles that need to go and my role was on the table. It was the kind of message that I was getting and it was a super hard thing to just process and then I came back and I had this conversation with her which directly said that in this room I remember quite vividly and then I was like, okay, I was happy to just leave and then had a really long an open conversation with my co-founder and my wife, Emily, who said this, we've done all that we could get the business so far.

23:30Why should I quit? And I should be fighting essentially. And so that was a joint decision. We decided to let the chair go. And then I did a change in my roles. I went from this managing a big team, technology, kind of happiness, kind of part marketing and stuff like that to this non-team management role where I decided to essentially create a startup within a scale-up. So launching a CPG brand and bringing that to retail under the Oddbox banner. I did that for the last two years of my stint at Oddbox. I got super proud of conceptualizing that idea, packaging, branding, and then launching Locado and going through that completely on my own to a large degree with some help from the team.

24:18But working through a coach, I gave this realization that I am a startup person. I'm not a scalar person. And this was a hard pill to swallow. I'm like, no, I see all these billion dollar business, million dollar business. I can do it. But then you realize, I don't enjoy that, that the rigor of managing teams and managing P &Ls and managing retailer. Just don't enjoy all of that. What I enjoy is the scrappy nature of doing stuff. And maybe that's my levitation and that's non-abuse me joy. That's in alignment with my values and I should go follow that. See, about 18 months ago, I decided I should follow my happiness, my potential.