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I’m becoming Executive Chairman of Printify (yes, that means I won’t be CEO)

I’m delighted to announce that the fantastic, amazing Anastasija Oleinikais going to be spending the next few months transitioning into becoming Printify’s new CEO. 🙌🥳🎉👏🏆🚀 This is the culmination of an 18-month process and a new chapter in my and Printify’s story. So it deserved a few thoughts, which you can read here:




Warning: There is some self-indulgence and reflection in this piece. If you want to get to the reasons I’m not going to be Printify CEO scroll down to “Reasons for the Change”.


The great thing that happened:

Yesterday, the fantastic, amazing Anastasija Oleinika became Printify’s Co-CEO. She'll shadow me for a few months until she’s ready to take over from me as CEO. When she’s ready, I’ll become Executive Chairman, focusing my time on delivering strategy and working out the next big bets for Printify to delight our millions of merchants.


This is my decision!

Yes, really, 100% me, no one is pushing me out of nowhere. Yesterday was the conclusion of an 18-month process to establish a world-class leadership team that includes me as Executive Chairman. During this time, the board and the team around me have been incredibly supportive, and now starts the next part of the plan - the transition.

I’ve loved being Printify CEO. But as we continue our journey to being a multi-billion dollar company that changes the lives of people around the world, I’m going to spend less time on the day-to-day challenge and put my energy where I can have the most impact - working on strategy and big bets.



The Reflection

8 years. That’s how long I’ve been CEO of Printify. For the sake of comparison, I asked ChatGPT for some other ‘things’ that take 8 years. Here’s the list it came up with:

  1. Completing a degree or two

  2. A medical residency

  3. Saving up for a down payment on a house

  4. Paying off a mortgage (this seems to contradict No. 3 a little)

  5. Learning a musical instrument

  6. Training a cat to do tricks

  7. Growing a bonsai tree from a seed

I look at that list and I feel pretty good about what we achieved at Printify. Sure, when I go to parties I can’t impress anyone with my saxophone skills or acrobatic cat, and I don’t have any micro-Japanese shrubbery to sit in the back of my Zoom calls, but I do have a sense of achievement that I’m sure is equivalent to all the things on ChatGPT’s list. We formed a company, reached 600 employees, raised $50m in investment, grew at an incredible YoY rate, attracted over 6 million sign ups, survived a pandemic, became the first Latvian startup to grant employees equity, and we’re now the most-searched-for print-on-demand platform in the world (we get more searches than “Print on Demand” these days). Oh, and I got to play tennis with Richard Branson - I lost.

When I started Printify, Artificial Intelligence was still a thing from the Terminator movies. I was in my mid-20s, no one could remember the last global pandemic, and eCommerce was still “emerging”. I was obsessed with becoming an entrepreneur. I think it’s because my parents always ran a business. I tried and failed a lot. Printify, my big success, emerged from the ashes of one of those failures. The idea for this failure was simple:

  • People have laptops

  • Laptops need a protective sleeve

  • People want something personalized

  • Personalized laptops sleeves should sell well

And they did sell well. But there was a problem, we had to buy a ton of stock without knowing exactly how much we would sell. The result was boxes of unsold stuff all over my dad’s garage, and a company with a cash flow problem that led to failure.

Surely there’s a better way!

Can we sell after a customer has bought?

Can we make everything on-demand?


Turns out that there is, we can, and we do. These were the key questions that led Artis Kehris, Gatis Dukurs, and myself to create Printify.

We started small, a shopify app with a few print partners. And we grew, sometimes fast, sometimes slow. We switched to a marketplace model (that was way harder than those 6 words suggest), we added a lot of print partners, we went from t-shirts and mugs to more than 850 products, we’ve shipped more than $1Bn worth of packages. And now we have built a team of 600 of the most bad-ass professionals anyone has ever had the pleasure of working with.

It’s been an amazing 8 years as CEO. I asked ChatGPT for words to sum it up. It gave me these:

  1. Rollercoaster

  2. Wild ride

  3. Marathon

  4. Saga

  5. Epic

It was all these things. And eventually, every epic wild marathon rollercoaster saga comes to an end. But this is not the end, it’s a new chapter.


REASONS FOR THE CHANGE

So why am I moving to the Executive Chairman role?

Because it will put Printify in the best possible position to become a multi-billion dollar company and delight customers around the world. Dreaming big and delivering innovation is where I know I can deliver the most value, and where I can help Printify reach its potential. Thinking about what innovation, product, features, or design will help more people unlock financial freedom and be their own boss is the reason I get out of bed every morning.

I love strategy. I will continue to participate in weekly strategy meetings, regular off-sites, and business review meetings. I’m excited to free up time from daily operational tasks to work on crafting our strategy, next big bets, and how we reach multi-billion dollar status.

Myself, my amazing leadership team, every employee, and the board, we’re all happy with what we’ve achieved at Printify. But we want more. We want to be a multi, multi-billion dollar company. Forget Unicorns, we want to be printing t-shirts with decacorns on them. And to do that, we need a CEO who can lead us there.

It’s just like having a prodigiously talented child who becomes a professional athlete (stay with me on this one). The early years are all about giving birth, nurturing the potential, getting through teething/growing problems, all that stuff. Then there comes a point where you have to get your child a professional coach who has what it takes to get your baby to the next level. Someone who can take your child to the next level. They’re still your child, you’re still going to go to every game, you’re still going to cheer louder than anyone else, but you’re not going to every training session, and neither should you.


So who is this amazing new coach (leader) that I’ve found for my baby - Printify? It’s Anastasija Oleinika. She’s awesome. She’s done it before leading Twino as CEO, helping them acquire an EU brokerage license and successfully transitioning from CFO. She knows us, she’s been our CFO for 7 months, during which time she’s impressed me and the whole team to a level I didn’t think possible. She’s shown us that she can drive impact (all the charts are going in the right direction). She’s undoubtedly the person to take us to the uni→deca→hecto-corn level.

I think my baby - Printify is really super prodigiously talented, so the fact Anastasija has a great team to help her raise my child is very comforting. Scott Richardson, currently Chief of Supply, is going to step up to COO. Scott has two decades of experience at Amazon and across eCommerce. He knows what it takes to create a category leader and provide world-class customer experiences. And to go with them we already have Greg Sewastianowicz who built the growth engine at Poker Stars, as well as Ashish Chopra who has joined us after running Product at Zalando, one of Europe’s biggest online marketplaces. My dear friend Edgars Peics whose been with me for 3 years completes the Printify leadership team as our CTO.

Printify is in a position to be the leading and dominant player in the on-demand manufacturing industry. I feel incredibly confident about the execution capabilities of Anasstasija. That is why I’m sure this setup will best realize Printify’s potential. And, I’m not going anywhere, I’m staying as Executive Chairman…

WHAT DOES AN EXECUTIVE CHAIR EVEN DO?

A: Nothing, it's a title people take before they go to Burning Man ❌

B: It has a really comfy cushioned leather seat and wheels on the legs ❌

C: They play a key role in setting strategy and direction for a company alongside the CEO ✅

This is not a ceremonial role, I’m still the single biggest shareholder at Printify, no one cares more than me about our direction and success. Second, I’ve promised my team that I will stay involved, I won’t just be turning up to the office with a tan to hand out high-fives. I’m going to lead our strategy, make decisions on our direction, and seek out the big bets, innovations, and opportunities that will help shape Printify into the colossal force that I know we have the potential to be. Yes, there may well be high-fives, but they will be handed out by someone who is deeply invested.

The thought of moving into this role after 18 months of planning it (yes, I spent that long on it, told you it was my decision) is super exciting. I know I’m at my best and happiest when working on strategy. I have incredible confidence in the execution capabilities of Anastasija. And I know together we will be a great team.

I can’t write this much without saying a massive thank you to every single person that’s contributed to Printify in the last 8 years. Our success so far is down to you, not me, and getting to spend time with you, learning from you, and sharing the journey with you was the very best bit.

Right, I’m off to help our new co-CEO take over from me so we can build the greatest version of Printify. See you around.


James

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