Transcript – #137 Jivko Bojinov, Co-Founder and SVP of Strategic Projects at ShipBob: On Playing Professional Tennis, Putting in the Work, Resilience, and Taking Things from Zero to One | 20 Minute Playbook

Please enjoy this transcript of my conversation with Jivko Bojinov, Co-Founder of ShipBob. We cover falling in love with the problem, inspiration from pro tennis, and maximizing learning early in your career.
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October 6, 2022
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Please enjoy this transcript of my conversation with Jivko Bojinov, Co-Founder of ShipBob. We cover falling in love with the problem, inspiration from pro tennis, and maximizing learning early in your career. Transcripts for other episodes can be found here

“At the start of your career, maximize learning and not your title or your pay, because the dividends that you would make over your lifetime from the greater knowledge and experience that you have early on your career are exponentially higher than getting an extra 5K on your signing from a company out of school.” – Jivko Bojinov 

Jivko Bojinov played professional tennis before co-founding ShipBob with Dhruv Saxena and Divey Gulati in 2014.

Jivko is currently the Senior Vice President of Strategic Projects at ShipBob. Over the last eight years, he's led the development and launch of almost every major strategic initiative that ShipBob has shipped, from their transition from owning their own fulfillment centers, to developing an asset-like partner network of fulfillment centers, to the launch of affordable two-day shipping for all of ShipBob's customers.

Transcript – #137 Jivko Bojinov of ShipBob: My Favorite Books, Tools, Habits and More | 20 Minute Playbook

Daniel Scrivner (00:06):

Hello, and welcome to another episode of 20 Minute Playbook by Outlier Academy, where we decode what iconic founders, renowned investors, bestselling authors, and outlier thinkers have mastered and what they've learned along the way. In each episode, we dive deep to uncover the tools, strategies, habits, routines, and hacks that we can all apply in our own lives, all in about 20 minutes. I'm Daniel Scrivner, and on the show today I'm joined by Jivko Bojinov, who played professional tennis before co-founding ShipBob with Dhruv Saxena and Divey Gulati in 2014.

Daniel Scrivner (00:33):

Jivko is currently the Senior Vice President of Strategic Projects at ShipBob. Over the last eight years, he's led the development and launch of almost every major strategic initiative that ShipBob has shipped, from their transition from owning their own fulfillment centers, to developing an asset-like partner network of fulfillment centers, to the launch of affordable two-day shipping for all of ShipBob's customers. You can find a searchable transcript of this episode, as well as our episode guide with ways to dive deeper, That's Please enjoy my conversation with ShipBob Co-Founder and SVP of Strategic Initiatives, Jivko Bojinov.

Daniel Scrivner (01:15):

Jivko, I'm thrilled to have you on 20 Minute Playbook. Thank you so much for joining me.

Jivko Bojinov (01:19):

Daniel, thank you for having me. Super excited to be here.

Daniel Scrivner (01:21):

Glad to have you here. Let's jump right into the questions. One of the things I always like to start with is a recent fascination. What are you obsessed with, fascinated with at the moment? What can't you stop thinking about?

Jivko Bojinov (01:34):

Yeah. Well, it's evolved over time, but I'm super fascinated with e-commerce and logistics. It's hard to shy away from that. To me, e-commerce is one of the greatest frontiers still where the American dream is still alive and you can have folks from zero to no education or zero to no funds figure it out, make it happen, and bring business commerce to not only their livelihood, but to also parts of the country that are maybe underserved. So it's something that I'm continuously fascinated about, and obviously logistics being with ShipBob.

Jivko Bojinov (02:11):

But recently, one of the things that has been more fascinating is just segments of the e-commerce space where fulfillment traditionally doesn't creep into or help out as much, and that's folks that do fulfillment on their own and they're in this stage where they're too big to hand it over to a more specialized professional service, and they're at a point where they need help. At ShipBob, we release some interesting products to help those folks out, but it's a really large segment that maybe gets overlooked at times that keeps me up at night these days.

Daniel Scrivner (02:57):

That's interesting. We're going to get into that a lot in our long-form conversation. I want to start with a question that's a little bit of a heavy question, but I wanted to ask it. Your parents immigrated to the US with you and became US citizens, and you're from Bulgaria originally. What kinds of risks did they take to do that, and I'm asking that because I know a little bit of the backstory, and what impact has that experience, being the child of first-generation immigrants, had on you?

Jivko Bojinov (03:23):

I mean, I can't speak enough about my parents, because my parents essentially gave up on pretty much everything that they were doing before in their life to come to a new country where they didn't completely understand the culture, the language, all those things, but saw an opportunity for my sister and I for a better future. When we immigrated, Bulgaria was like, it was the mid-'90s, communism fell apart in '99. There were a lot of turbulence, changes, and it was a great opportunity, and my parents were entrepreneurs in Bulgaria and they also had stable jobs and great education, and they literally came here and started from scratch.

Jivko Bojinov (04:11):

So, watching them go through that and the long hours they worked and the things they had to do to just put food on the table and to make things happen, yeah, it was a life-changing decade, or I don't know how long part of my life there, that instilled a lot of great lessons. But also, it instilled some things in me that, I'm not sure [inaudible 00:04:37], which is just this inner drive to essentially to make the most of the opportunities I have, to strive for more, because I've seen what people have sacrificed to give me that opportunity. So, I am incredibly humbled and thankful, and I can't speak about that enough for what my parents have done.

Daniel Scrivner (04:57):

Switching it up, you've taken a number of unorthodox routes in your career, including dropping out of college to become a professional tennis player, which is a whole interview we could do in and of itself on that experience and that period in your life. I'd love it if you could share a little bit about that experience, what you learned from it and what that taught you, being a professional tennis player for a year, what that taught you that you've applied to ShipBob and that you've applied to your life since then.

Jivko Bojinov (05:23):

I started college, and after my freshman year I dropped out to play tennis professionally. And at the time, I played tennis obviously for a long time prior, it wasn't just like a random venture, I wanted to essentially pursue my dreams and I realized that being in school was time that I'm not spending on the tennis court and if I don't give it a shot, I will never really know what I could have done with a tennis career. And after playing tennis professionally for a year, it helped me realize also the reality of what it would take to be successful and to be able to feed a family playing tennis, and more so the chances of doing that, which helped me ground myself back into the world of business.

Jivko Bojinov (06:12):

But there were some incredible lessons from it that apply to business. For one is, at some point, once you realize what you want to do, you've got to burn the bridges of everything else and have this deep level of focus. So dropping out of school, selling my car and moving down to Florida, like complete remove myself from my comfort zone and put myself in an environment where I can focus just on the one thing that I cared about, in that case it was tennis. Doing that in a business setting I think has massive dividends. It had massive dividends for my tennis game, even though I'm not playing tennis anymore, I still feel like a much better tennis player after that year, but some of the nuances once you've burned all the bridges and you're doing this a hundred percent of the time.

Jivko Bojinov (07:02):

One of the interesting takeaways was I was playing tennis and you could, in Southern Florida during the summer, you can spend maybe four hour tops in the sun outside, and the rest of the time, you were doing activities, like you're stretching, you're eating, you're sleeping, everything else, and all of that had to become a part of becoming a better tennis player. You spent way more time off of the court doing things that doesn't always seem to directly benefit your top mission that were extremely beneficial. Like if you didn't get enough sleep, you couldn't play for those full four hours and you didn't maximize that time.

Jivko Bojinov (07:43):

So I think just that concept of realizing how much of the things that you do have an effect when they're not necessarily in that prime moment. Like in the business world, you might have to be on a sales call or something where you have to deliver, but it's all the other time that you spent and the research and all those things, or whatever it may be, that help prepare you for that moment, and that's equally, if not more important than that hour or moment when you're actually, you have to perform.

Daniel Scrivner (08:16):

I want to ask one more question about tennis. Tennis is a sport with a lot of really colorful characters in it. Are there any, well, I'm sure you have them, who are your favorite players and why are they your favorite players? What do you take away from the way they play the game or the way they approach the sport?

Jivko Bojinov (08:33):

I used to be, well, I still am a huge Roger Federer fan. How can you not love the guy? But I've come around on a Rafa, Rafael Nadal. Early in his career, we're the same age, when we started out, we had the same hairstyle and he obviously became a little more successful at tennis. But early on, I wasn't a big fan of Rafa. He seemed too bold and brash and stuff, but over time, just seeing the amount of effort and dedication and how much he's persevered and the things he's done, you're just humbled by that work ethic and that focus. So I'm a huge, huge Rafa fan now, but that wasn't the case in the start of his career.

Daniel Scrivner (09:21):

My mom's a huge Rafa fan, so she will appreciate that. I'd love to switch gears and talk about areas where you think you have an edge or a superpower. And that may sound a little bit lofty when I use a label like superpower, but from my perspective, the reason I frame it that way is I think we all come with things that are just innate to us that we kind of over-index on. And it can be due to the way that we're wired, it can be due to what we're attracted to in life, it can be to parts of our personality. When you think about your edge or superpower, what do you think those are? And then how do those show up in your day-to-day work?

Jivko Bojinov (09:54):

For me, it'd probably have to be resilience, and I think there's two facets to resilience. One is the ability just not to give up and to keep going under a great degree of pressure and whatever may come up, if numbers are not favorable to what you're doing, to keep going. And the second part to it is the part of resilience where you can bend and give, but not break. So I think the way this falls into my business philosophy is I'm pretty clear into the goal that we need to get to and I can give on how we get there, how much time or how we fund it or how we figure it out. And that comes into play in all daily project stand-ups, whatever we have with our team and the way we move through a lot of the goals, so yeah.

Daniel Scrivner (10:57):

I think resilience is a great answer, and I don't think anyone has given that on the show, so I love that is your superpower. This is a little bit of a curve ball, I haven't asked this one before, I'm going to try this question out on you. So thanks for being my guinea pig. If people listening could shadow you for a day and they can just see what your daily routines and habits and just your daily work and life is like, what do you think they would be most surprised by? And what I'm thinking of there is habits and routines, anything unique about the way you approach your work or approach your life. What do you think people might be surprised by?

Jivko Bojinov (11:29):

Yeah, it's evolved recently for me because I recently became a dad. So my daily routine's greatly changed.

Daniel Scrivner (11:39):

It's very different.

Jivko Bojinov (11:39):

Yeah, but one of the things is my team will always tell you that I'm always available any time of day, and they probably feel this way, but I go to bed super early and I think that's something that folks would be surprised by. And I get up now super early, and I spend probably about two and a half, three hours playing with our daughter and making her some breakfast, and that creates my routine for the day that kicks off my day. Yeah, and historically, I feel like folks in the creative space usually tend to stay up later and do a lot of creative work late at night, but that's completely flipped for me recently, and I can't advocate for it more.

Daniel Scrivner (12:22):

Now you're an early to bed, early wake up kind of guy. Related to that, what sorts of values and standards do you bring to your work every single day? And part of this goes back, I mean, resilience is maybe one of those, but what I'm thinking of here is you talked about being always available, what other values or standards do you set for yourself just in terms of how you show up, show up with your teammates, how you show up at the company?

Jivko Bojinov (12:46):

They're kind of profound in our company values. I think there were set as a reactive based on what myself and the other founders, and early on what we were doing. But just being humble, I think, and a lot of people say that word, but I think it's different to live it, and to be humble in the approach to dealing with folks, with merchants, with whoever you might interact with. The other one is just being a creative problem-solver. And that's in a lot of different facets, like for our department, we're setting up new business units all the time, so what we have to do is connect the dots between different ideas and departments and resilience, which you mentioned and you took out of my breath there. But yeah, those are the three things that I probably come to work with every day and shine through.

Daniel Scrivner (13:42):

I always love to ask guests about their favorite books. When you think about books, favorite books, are there any that either had an outsized impact on you or that you find yourself giving away to others, recommending to others? Any favorite books to share with the audience?

Jivko Bojinov (13:56):

Yeah, so this is not a normal business book, or I have a theory that I think a lot of folks in the business space need to read a little bit more fiction. So that book for me is The Count of Monte Cristo. For one, I think as a business leader, a lot of what you do is storytelling, and having examples of great fiction, of great storytelling helps with that, and also being able to, I think, take your mind off of the everyday things and connect dots. And then something about the book, it's like there's a lot of different business analogies in there, but just the ability to deal with what happens when your reality completely shifts and how you react to it. The Count of Monte Cristo ends up being a vengeful path in the second half of the story, that's maybe not the best takeaway, but just what do you do when your whole life flips upside down? Yeah, so that's a book that I've given away a couple times to folks and I love to reread.

Daniel Scrivner (15:03):

Yeah, that's a great one where I've definitely seen the movie, I imagine a lot of people have seen the movie, but I don't think enough people have probably read the book. I know I haven't. And I imagine there's probably a great audio book version of that, so I need to go and look. One of the questions I was burning to ask you is, and you touched on it a little bit, but your role at ShipBob is really unique. You're in charge of strategic projects. You've basically spent a number of years now standing up new business lines, new features, new products within the company.

Daniel Scrivner (15:30):

And so one of the questions I want to ask is what you think you've learned by taking a number of things now from zero to one? Because obviously, if you're focusing on strategic projects, you're starting off with some sort of business challenge or some sort of goals, typically metrics that you need to be moving towards, but you have to fill in all of the blanks and then take that from an idea into something that's working that at some point you likely hand off to somebody else or to a new team. Any thoughts on solving zero to one or navigating the chasm?

Jivko Bojinov (15:59):

I think that on the zero to one, I think for one is you need to find something that you love doing and you need to keep refinding that in whatever problem you're solving. If you don't really love it, even when somebody else tells you to, just throws you into it for example, like I get to be in a lucky position where I get to chart that path, but in some cases, folks in a similar role might be, their C-level executives might tell them, "Go do this," you need to fall in love with it, and if you don't, you need to question it until you do. And then you need to get started, and to get started, I think you need to have somewhere around 30% of the information to get moving forward.

Jivko Bojinov (16:42):

That's a number where I think you recognize that you mostly don't know everything, but you have enough information to get a directional start. And from there, it's just a matter of getting feedback from the people that you think are your customers. And I say the people that you think are your customers, because that might change by the time when you start to talk to those folks. And then taking that feedback to fill in the rest of your, probably not all 70%, but maybe at least 60% of that. And then one of just the things about doing this over and over is one of the most difficult things is, well, for one, that if you follow this of falling in love with a problem, you get to a point where you have to create this organization where you're useless and you hand it off to somebody else, and that's a really difficult thing if you actually loved it.

Jivko Bojinov (17:39):

I'm thinking about my child currently right now and when she grows to be, goes off to college or something of that sort, but you have to find a way to be in a position where you're comfortable to do that. And it's really difficult, till this day when some of the most recent business unit that became and got absorbed by ShipBob in full, it was really difficult to let it go. And that's probably a good thing if you feel that way. That means you've done something right. But you still need to be prepared for it, because it's a difficult stepping stone.

Daniel Scrivner (18:15):

Yeah, I love that framework. One of the questions I want to ask related to that is solving the zero to one problem, it makes me think of what you brought up earlier, which is resilience. I have a background in design, I feel like as a designer, as a company builder, you grapple with a lot of zero to one problems, and one of the things you realize is there are just really hard moments in creating anything. You come through periods where you're either stuck in a negative feedback loop, you don't feel like you're making progress, you have to just keep moving forward. What's your approach in those moments or what have you learned from being in those moments so often?

Jivko Bojinov (18:51):

Yeah, it's difficult, but I think what gets you out of it is just doing more. So if you have a negative feedback loop from let's say your internal team or just simply your numbers or whatever it may be, it's talking to more customers. And in this case it's maybe you're not talking to the right customer, so you might need to start looking at what are tangential or folks that were referred, but yeah, talking to more people that face this problem essentially on a daily basis. And you might not get enough traction still or what you need to move forward, but sometimes their stories or knowing the things that you will solve for them when you get this right is what will keep you going.

Jivko Bojinov (19:39):

Yeah, and it's not easy, and at some point things just don't work and you need to move on. But it's a really tough and fine line to be able to make that call. But generally, when I'm facing those situations, and then you're close to giving up, I think that you need to do that twice at least. And on the third time, you could be like, "Okay, maybe it's time. Maybe I've exhausted everything that I've tried."

Daniel Scrivner (20:07):

Yeah, I like the three strikes rule. It's also very hard to get to three, I imagine, for a lot of people. I want to ask a closing question to wrap up this interview, and it's the same one I ask every guest, which is if you could go back to the start of your career and whisper some advice, a reminder, or words of wisdom into your ear, is there any advice that you would give your younger self?

Jivko Bojinov (20:26):

That's a great question, and I think the keyword there is the start of your career, and I think I feel lucky to have kind of fallen into this advice, but it would be to maximize learning and not your title or your pay, because the dividends that you would make over your lifetime from the greater knowledge, experience that you have early on your career are exponentially higher than getting an extra 5K on your signing from a company out of school, or an extra, I don't know, whatever, a couple, two weeks off or whatever that benefit package might be from a company.

Daniel Scrivner (21:10):

I think that's a great lesson to share with everyone listening to the episode, because I've found the same thing. Money, yes, you can invest it, you can compound it, a title doesn't get you anything else really, maybe other positions in a similar title. But yeah, I think when I think back to the early part of my career, the thing I'm most grateful for was, one, not to be in COVID where everyone was working remotely and to be around people, because I so much learning happens by just talking and sitting and observing other people working, and I feel like a lot of people miss out on that today. Do you feel similarly, any thoughts on how to learn in this kind of remote or hybrid world?

Jivko Bojinov (21:46):

Some things that we've done internally as a company, that if your employer or your company's not doing that you could just kick off, is we have these virtual coffee sessions. We use an app for it that randomly matches folks, but if you don't have something like that, be the person that sends an email or Slack, whatever you're curious about, and just put time on people's calendars. I think generally, folks will come to it. And early on, it's okay to be ambitious or brash and ask for forgiveness. If you put 30 minutes on the CEO's calendar and he doesn't want to give you the time or doesn't like it, that's okay, you tried. But you could have picked their brain for something really cool.

Jivko Bojinov (22:32):

And then also, just try to connect with people in unique ways. I think a lot of people are coming, getting into the office or some sort of hybrid, but sending people gifts and getting to talk about those gifts or things are a way that I found connecting with folks during COVID was great. I sent some books out, it's actually great that you asked that question, but yeah, just some ideas.

Daniel Scrivner (22:59):

Yeah, that's great advice. Well, thank you so much for joining me, Jivko. This has been a great conversation and I appreciate your time.

Jivko Bojinov (23:05):

Really enjoyed it.

Daniel Scrivner (23:08):

Thank you so much for listening. You can learn more about ShipBob, including their global omni-fulfillment solution that's trusted by over 7,000 brands to ship orders everywhere their customers shop, at You can find a searchable transcript of this episode, as well as our episode guide with ways to dive deeper, at That's

Daniel Scrivner (23:31):

For more from Jivko Bojinov, listen to Episode 138 where we decode how ShipBob has grown from shipping orders from the Co-Founder's apartment to running a network of 30+ fulfillment centers located around the world that 7,000+ brands used to ship orders everywhere their customers shop, including brands like 100 Thieves, Spikeball, Tom Brady's TB2, and many, many more. You can find that episode at That's

Daniel Scrivner (24:00):

For more from Outlier Academy, follow us on Twitter, LinkedIn and TikTok. Subscribe to our YouTube channel at or visit Outlier Academy for more incredible 20 Minute Playbook episodes. We'll see you right here with a brand new episode next Tuesday.

On Outlier Academy, Daniel Scrivner explores the tactics, routines, and habits of world-class performers working at the edge—in business, investing, entertainment, and more. In each episode, he decodes what they've mastered and what they've learned along the way. Start learning from the world’s best today. 

Explore all episodes of Outlier Academy, be the first to hear about new episodes, and subscribe on your favorite podcast platform.

Daniel Scrivner and Mighty Publishing LLC own the copyright in and to all content in and transcripts of the Outlier Academy podcast, with all rights reserved, including Daniel’s right of publicity.

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