"Roy Rubin's journey from dorm room to billion-dollar business."

Join us as we delve into the journey of Roy Rubin and how he grew Magento from a UCLA dorm room idea to processing over $200+ billion GMV. In this episode, we unravel the strategies, innovative approaches, key decisions and the massive shift to enterprise sales that catapulted the business to great heights. Today, we'll cover: - The genesis of Magento and its innovative approaches to commerce. - The lessons learned from challenges faced during Magento's evolution. - The strategic decision to shift focus to enterprise sales and the impact it had on the company. - Roy Rubin's reflections on the past decade of entrepreneurial trends and the potential of AI and blockchain technology. - Dive into his latest venture, RSquared Ventures, and their unique approach towards incubating and investing in entrepreneurial teams.

"Retention Supercharged: See how brands are nurturing deeper customer relationships with easy to use retention tools that hyper target and provide immediate growth." — Ramon Berrios 00:01:02 00:01:33

"Timing is Everything": It just shows how important of a factor the timing is, which is an element that you mentioned earlier. — Ramon Berrios 00:31:04 00:31:23

"Accelerating Innovation": "I think we're entering an interesting and exciting phase now where anything that can help make the speed of iteration faster and the rate of deployment of things and testing that accelerated is probably what is the next phase." — Ramon Berrios 00:32:03 00:32:35

"Inward Discoveries: The Moment You Stop Looking Outside and Find It Inside, That's When Magenta Was Born" — Ramon Berrios 00:35:27 00:36:30

"The Commodity of Tech: What RSquare Ventures is About": "The tech is the commodity. So I'm curious. You have your fund RSquare Adventures. You've had all this experience selling, the company, going back, selling again. You've seen it all. How has that shaped your lens for what you look for, what opportunities you find interesting? And what is RSquared Ventures about in your guys'thesis and what you find interesting?" — Ramon Berrios 00:37:41 00:38:07

GPC three technology, education, technological advancements, open source technology, enterprise technology, internationalization, multi-currency support, multiple site and brand implementations, template engine, technical debt, product design, community engagement, enterprise business, revenue model, customization issues, product troubleshooting, entrepreneurial company, DNA of an organization, innovation, company acquisition, cloud company, Web Three, blockchain, cryptocurrency, Artificial Intelligence, entrepreneurship, RSquared Ventures, early stage funds, investment strategies, work-life balance.

1. Evolution of Magento and its innovations 2. Importance of community engagement and contributions 3. Shift to enterprise sales and dual licensing 4. Comparison between entrepreneurial and corporate cultures 5. Reflections on missed cloud trends opportunities 6. Personal involvement in AI and GPT-3 advancements 7. Early days and formation of Magento

02:28 Freelance programmer builds Magento for ecommerce, grows to 30 people, fires all customers to focus on product.

10:01 Open source product with UI/UX designer, flexibility to customize, multi currency, multi site, internationalization, technology debt-free; transparent development led to mass following before product launch.

15:10 Product had massive followers, but no revenue model. Pivoted to enterprise offering with dual license strategy and additional support.

18:46 Pivoted to enterprise business, sold $100 million+ but complex product caused difficulty in understanding customer issues.

21:41 Commerce matured quickly in 2006-2007, leading to the growth of Magento with 300 agency partnerships and over $1 billion in service revenues. Magento gave away a great product for free, but it was hard to monetize until the business caught up.

25:36 Entrepreneurial company aggressive, big dreams, innovative, successful, but ebay was very different, too slow and less risk taking; missed out on cloud opportunity, led to Shopify's growth.

28:58 Magento had apps and mobile capabilities since 2008, anticipated the cloud and Shopify, and discussed ideas for Shop app in 2006-2007.

38:07 Early stage fund investing in fintech, commerce, marketplaces & editing; seeking teams with product & technology acumen & go to market experience; operators rolling up sleeves to help founders.

41:36 Rewarding and fun experience of helping founders build amazing products, allowing entrepreneurs to have a life with family and friends while still building their company.

44:08 Incubating early-stage businesses that need assistance to become successful.

On this episode of DTC Pod, we follow Roy Ruben, founder of Magento, as he takes us through his journey of building a business from the ground up. We learn about the challenges he faced when transitioning from an enterprise sales model to professional services and his experience with larger organizations like eBay. We also get a peek into the future of Roy's projects and the teams he is looking to partner with.

We built Magento and it was accessible to the world. And that's been an amazing journey. Roy Rubin is a former student at UCLA who had a passion for programming and a vision to make a mark in the growing ecommerce industry. Using his programming skills, he started a freelance business in 2001, focusing on open source ecommerce. His business quickly flourished as the demand for online stores grew and he grew his small consultancy to 25-30 full-time people while still at UCLA. In 2005, Roy decided to take a risk and fire all his customers so he could focus on building a next-generation platform that would become Magento. His risk paid off and his platform is now accessible to the world, making Roy a success story in the ecommerce industry.

Topic: Roy Rubin's Early Life - Freelanced in open source ecommerce - Started small consultancy at UCLA - Made good money and had interesting conversations with merchants
Topic: Magento - Early days of Google Ads - Open source vs. million dollar software - Doubled down and fired customers to build product - Founded with engineer and inspiration from 37 Signals

"In today's episode on DTC POD, we had an inspiring chat with Roy Rubin, whose journey from a UCLA dorm room to generating over $200 billion in GMV with Magento is nothing short of breathtaking. We covered his innovative approach to commerce, surprising revelations about Magento's early days, pivotal decisions that led to Magento's spectacular growth and Roy's insightful view on technological advancements. We also delved into lessons learned and future prospects in AI. From startups to breakthroughs, join us as we dive into this exceptional entrepreneurial odyssey."

Come listen to our most recent episode of DTC POD, where we take you behind the wheel with Roy Ruben, founder and CEO of Magenta, and get an inside look at his journey from setting up shop to selling Magenta to Ebay and Adobe. Plus, find out how he reflects on his entrepreneurial journey and what projects he's working on next. Use the code DTC Pod ten for 10% off your next content purchase.

Some key takeaways from the discussion 👇

1/ We had a lot of help from the community and we launched version one of Magento and version one was pretty successful. Ramon and Blaine, two former students of UCLA, started a journey in the early 2000s to build an open source ecommerce platform. By placing an ad for open source ecommerce services, they were able to build up a small consultancy with 25-30 full time people while still in college. They eventually fired all of their customers to pursue their ambition of building a product, which resulted in the launch of Magento version 1.0. With help from the community, the platform was successful and has remained a popular choice for ecommerce businesses.

2/ In the pre-cloud era, open source was one of the few options for technology stacks, and enterprise was the other. Magento was created to fill the gap between the two with an innovative and modern solution. It featured internationalization, multi-currency, multiple sites and brands, and a template engine that allowed for easy customizations. Magento also had a full-time UI/UX designer, something unheard of in open source products at the time. The creators of Magento were also incredibly transparent, sharing wireframes on their blog and engaging with the community to build the product. This level of transparency and engagement with the community helped Magento launch as a slam dunk from day one.

Subject Line: New Episode Alert! From UCLA Dorm Room to $200 billion in GMV on DTC Pod Hi there, We've got some incredible content coming your way in the latest episode of DTC Pod. In this episode, we're talking with none other than Roy Rubin, co-founder of Magento. This is an episode you won't want to miss! Here are five key things that you'll learn from Roy in this episode: 1. The journey of Magento: From a dorm room startup to handling over $200 billion in gross merchandise volume on their platform. 2. How Magento pivoted from being an open-source platform to offering an enterprise solution that generated significant revenue. 3. The importance of the customer community in shaping a product, as seen through Magento's utilization of their blog for product feedback. 4. Roy's insights on overcoming challenges in product customization and troubleshooting. 5. How larger companies can sometimes stifle innovation due to differing priorities, and the need for entrepreneurs to understand the DNA of an organization. Fun Fact: Did you know that Magento had an App Store called Magento Connect as early as 2008 or 2009? Yes, even before the concept became widespread. Outro: We wrap up the episode with Roy's thoughts on the fascinating world of AI and its potential to transform businesses. His frank views and experiences provide an insightful look into the mind of a pioneer who’s been at the forefront of eCommerce innovation. Call to Action: Sound intriguing? Tune in now to hear the full story on your favorite podcast platform, and don't forget to subscribe to DTC Pod for more fascinating discussions with industry leaders. Know a friend who needs to hear this? Share away! And as always, let us know what you think! Your feedback helps shape our content. Cheers and happy listening, Blaine Bolus and Ramon Berrios DTC Pod

1/ Imagine launching an innovative product only to find your partners becoming competitors. Welcome to the unpredictable world of tech entrepreneurship as lived by @royrubin05, co-founder of Magento. Let's dive into his extraordinary journey. 2/ Young and in college, Rubin decided to leverage his tech skills to offer freelance work focusing on open-source e-commerce. This venture would sow seeds of something more significant than Rubin could have imagined. 3/ The demand for his services skyrocketed so much that he had to shut down his ads. But it wasn't sustainable. Running service-oriented operations while building a key product became a herculean task. So he made a hard call- he fired all his customers. 4/ The product? Magento- Revolutionizing the e-commerce scenario, Rubin and team brought an open-source model to commerce. In a world of pricey software from Oracle & Microsoft or open source trends, Magento's uniqueness lay in its model. 5/ Magento’s enterprise was a fine piece of software engineering- internationalization, multi-currency support, and multiple site & brand implementations among others. But challenges lay ahead. 6/ Rubin had a massive following, a product that consumers loved, but what to do with it? Monetization, the omnipresent conundrum of many startups. Then, the unexpected occurred. His partners, aiding in support roles, began transitions to competitors jumping on the Magento bandwagon. 7/ What do you do when the world around you starts building similar things, creating an ever more crowded space? For Rubin, the answer was to pivot and cater to the enterprise space. 8/ Magento’s enterprise version was born out of this pivot. It came equipped with additional features & extensions not present in the free, open-source offering. Still, as customer issues revolving around customization & troubleshooting piled, the move seemed timely. 9/ Hindsight, Rubin says, shows the move was wise. 100+ million in revenue suffices as proof. But the journey wasn't all smooth sailing. Realizing Magento's potential, eBay swept in and acquired, slowing down progress due to different priority sets. 10/ And so came about the rise of Shopify. An opportunity missed, Rubin reflects, a cloud company that Magento could have become. What’s fascinating though is, Shopify's key innovations like its App Store were present in Magento years ago! 11/ Rubin’s journey is not just one of the entrepreneurship rollercoaster but also about how to adapt to what the market offers and demands. It's about leaps of faith, multiple pivots, and never losing the zeal to innovate. 12/ Today, Rubin & Co are nurturing nascent ideas, providing a launchpad to startups, through their early-stage fund - RSquared Ventures. Calling upon their arsenal of experience to guide others towards success - a true testament to an entrepreneur’s resilience. 13/ Rubin's saga of entrepreneurship is a story of survival, agility, & transformation. His talking about AI piques interest, talking of breakthroughs looming close. For now, the world continues to watch & learn from Rubin’s extraordinary journey. [End of thread]

1. "Embracing Tech Advancements": Evolving technologies are essential for businesses to create value and remain competitive. 2. "The Open Source Impact": Magento's open source nature allowed its wide adoption and engagement via insightful community input. 3. "Pivoting for Survival": When partners turned competitors, it was crucial for Magento to pivot towards an enterprise offering. 4. "Understanding Organizational DNA": Discerning an organization’s inherent style aids innovators in finding organizations that champion innovation. 5. "Cloud Transformation's Missed Opportunity": Magento's acquisition by eBay impeded its transitional journey towards becoming a cloud company. 6. "True Innovation Paradigm": Successful innovation strategies involve looking internally, implementing AI in existing workflows and solving current problems. 7. "Investing in Incubation Opportunities": Investing in teams with incomplete ideas but promising prospects presents exciting incubation opportunities. 8. "Value-added Venture Capital": A venture capital fund that actively assists founders can significantly supplement their journey. 9. "Breakthroughs in AI": There’s a looming breakthrough in AI, where entrepreneurs identifying core needs can tap into new markets. 10. "Origin of Magento": From a small freelance operation, Magento emerged as a leading open-source eCommerce platform.

1. Be adaptable to technological advancement: Like the arrival of pocket calculators, new technologies may initially disrupt established systems but often become valuable tools. 2. Value lies in innovative use of existing technologies: Companies that can utilize new technologies to create unique value propositions will succeed. 3. Open-source provides an astounding degree of customization and flexibility: Harness it to create products that better serve your customers. 4. Align with your community: Engage with your users or audience to gather valuable input for product development. 5. Be prepared for competition: Always anticipate how your partners might eventually become your rivals. 6. Implement dual revenue strategies: While offering products for free can generate a large user base, implementing a paid service targeted at larger customers can provide substantial income. 7. Understand your product's intricacies: Not all user issues can be easily resolved; it's crucial to comprehend the complexities of your product or service. 8. Reflect on past decisions: Even supposed missteps can prove pivotal for business growth or change in direction. 9. Identify opportunities in larger organizations: While large organizations might appear slower or risk-averse, they often present huge opportunities for bold innovators. 10. Be ready to seize opportunities: Recognize and seize game-changing trends, such as the rise of cloud computing. 11. Learn from the past: Previous ideas and trends often resurface in a refined way. Recognizing their potential early can prove beneficial. 12. Embrace technological complexity: Novel, complex fields like blockchain and cryptocurrency can seem elusive but promise significant potential. 13. Pursue your curiosities: Innovations such as AI can lead to significant advancements. 14. Innovation can be found within: Instead of looking externally for inspiration, work on discovering and utilizing internal resources. 15. Value-Added Investments: When investing in start-ups, aim to provide more than just financial backing - active participation and consultation can lead to better outcomes. 16. Simplify complex systems: Capitalize on systems with high entry barriers or those utilizing outdated methods, like RV parks booking. 17. Remain committed to your portfolio companies: Investors should prioritize maintaining strong relationships with founders they support. 18. Constantly push innovation boundaries: Whether in AI or other technologies, being on the cutting edge can lead to breakthroughs. 19. Partnerships drive growth: Building partner programs and collaborations can help both scalability and profitability. 20. Harness global talent: Don't limit your team to a specific region; valuable talent can be found worldwide. 21. Prioritize the product: Juggling other business while building a product is challenging. Sometimes, cutting off some aspects helps focus energy on product development. 22. Disruption leads to opportunity: Identify areas ripe for innovation - like how Magento saw potential in the open-source model for commerce.

Subject: Thanks for Joining Us on DTC POD, Episode Now Live! Hey Roy, Just wanted to shoot a quick email to say a massive THANK YOU for taking the time to come on the DTC POD. Your journey from a UCLA dorm room to driving $200+ billion in GMV with Magento was an eye-opener for our listeners, and we've been receiving some really positive feedback! We've just published the episode, you can check it out [here-insert link]. It was amazing to hear your insights about pivoting to enterprise sales, betting on open source when it was still a novel idea and your fresh take on the emergence of AI. Your story has been inspiring and the insights invaluable. A big part of the success of these episodes comes not just from the recording, but also the chatter it creates afterward. If you could give us a hand by sharing the episode link across your social channels and engaging with any related content, it would be greatly appreciated. Once again, thanks a ton for sharing your wealth of knowledge and experience with us and our audience. Catch up soon! Cheers, Blaine & Ramon DTC POD Team

1. The speaker started as a student at UCLA with no money doing freelance work focusing on open-source ecommerce, revealing that Magento was conceptualized in a dorm room. 2. Despite having a successful product and a massive following, the speaker initially had no revenue model in mind, showing the unpredictability of entrepreneurial journeys. 3. Interestingly, Magento had an App Store called Magento Connect dating back to 2008 or 2009, long before such features became standard in similar platforms.

Title: A Journey from UCLA Dorm Room to $200+ Billion GMV - Reflections with Roy Rubin Subheader: Navigating eCommerce Challenges, Open Source Innovation, and the Untapped Potential of AI with Roy Rubin Section 1: Bootstrap Beginnings and Embracing Open-Source In a jaw-dropping episode of DTC POD with hosts Blaine Bolus and Ramon Berrios, guest Roy Rubin captivates us with his story of starting as a UCLA student doing freelance work in ecommerce. Faced with saturated options of open-source or expensive software products, Rubin saw potential in innovating on the open-source model, which hadn’t been applied to commerce yet. Eager to realize this potential and take their efforts to the next level, the team took the brave step of transitioning from a services company to create what is now known as Magento. They fired their clients, focused on product development, and Magento was born. Section 2: Building Magento and Learning from Partners Turned Competitors Magento's unique approach to commerce, with features like internationalization and multi-currency support, made waves. However, the road to success was not without its bumps. Rubin and his team were optimistic but did not foresee the support their partners would provide for their product, making them competitors. Despite these unforeseen challenges, Rubin pivoted, focusing on enterprise sales and adopting a dual license strategy. This innovative maneuver significantly helped boost revenue, surpassing the $100 million mark, an outcome that exceeded initial expectations. Section 3: The eBay Acquisition and the Shift That Could Have Been After being acquired by eBay, Rubin describes a shift from Magento's innovative, fast-paced atmosphere to a slower and less risk-taking approach at eBay. With a keen focus on transformation into a cloud company, Rubin suggests that this shift could have potentially bullied the growth trajectory of competing platforms like Shopify. Magento was already setting the tone in innovation with products such as Magento Go and a structured App Store long before its time. Section 4: Exploring Web Three and the Promise of AI Rubin's insightful conversation with the hosts navigated through his exploration of elusive domain developments such as Web Three, blockchain, and cryptocurrency. He expresses a personal fascination with the field of AI and believes it could usher significant changes in the business landscape. Providing a perspective on future technological advancements, Rubin stressed the importance of integration and innovation in transforming businesses, highlighting how AI-driven solutions could open new market opportunities. Section 5: A Venture into RSquared Ventures Rubin also shares his current foray into venture capitalism with RSquared Ventures, a fund he co-founded with Roy Ariz. Focusing on fintech, commerce, marketplaces, and editing staffs, RSquared Ventures sees potential in young teams with incomplete ideas and takes an incubation approach to development. With twenty investments already under their belt, Rubin and Ariz look forward to supporting more founders and driving the innovation ecosystem. Section 6: Reflections and Belief in Future Breakthroughs Drawing parallels to the field of AI, Rubin emphasized the importance of internal resources and solving current problems with the implementation of AI in existing workflows. Looking back on his journey of building Magento from scratch to driving over a billion dollars in service revenues for their partners, Rubin sees the shift in the industry and acknowledges challenges they had to overcome. The combination of a unique product, the ability to harness technology, and a community-focused approach were key to their success. Concluding, Rubin highlighted his personal aim for work-life balance and expressed appreciation for the rewarding journey he has embarked on in this industry. As he looks to the future, he firmly believes we stand on the verge of a breakthrough in the AI field that will unlock new market opportunities and reaffirm the potential innovations technology holds.

"Join us on DTC POD as we learn from Roy Rubin, co-founder of Magento. Discover his journey from a UCLA dorm to handling billions in global transactions. We delve into the innovative approach and pivots that lead to a successful enterprise offering, capturing the importance of understanding a product's user base. We explore the transformative role of technology, learning how past ideas keep surfacing with improved execution. Also, we outline how Rubin sees AI reshaping the future and highlight lessons learned for entrepreneurs. So tune in for an insightful conversation packed with wisdom from the arena of digital commerce."

When launching a disruptive technology or product, engaging with the community and gathering input is essential. A transparent approach and consistent storytelling can build a large following pre-launch. Innovators should stay agile, ready to pivot and adapt to unexpected changes, like competition from partners. A dual license strategy can offer a core product for free while monetizing through an enterprise version. If user issues arise due to complexity, providing an abundance of self-serve resources and tutorials can be beneficial. Importantly, companies should continuously look inwards for innovation and improvement rather than externally. Lastly, valuing existing relationships with founders and supporting them can be as rewarding as the innovations themselves. Always stay excited and dedicated to the journey of innovation.

Slide 1: "Maxims from DTC POD: Roy Rubin of Magento" Slide 2: "Not: Dismiss Innovation" Do: Keep an open mind to new technological advancements and look for ways to integrate them into your business. Slide 3: Not: "Ignore Customization Concerns" Do: Provide resources and support to customers experiencing issues with customization. Slide 4: "Not: Compete In All" Do: Know when to pivot, focus on strengths and rechannel energy to where you can provide unique value. Slide 5: "Not: Off-the-Shelf Approach" Do: Custom-build solutions to match your business model, like Magento's dual license strategy. Slide 6: "Not: Underestimate Partners" Do: Acknowledge that partners can comprehensively understand your product, sometimes better than you. Slide 7: "Not: Rush Decision Making" Do: Take your time, understand the DNA of an organization before committing to it. Slide 8: "Not: Neglect Internal Innovation" Do: Shift focus from external ideas to finding potential internally. Slide 9: "Not: Pass On Incomplete Ideas" Do: See incomplete ideas as opportunities for incubation and creation of value. Slide 10: "Not: Rely On Capital Alone" Do: Look for investing partners who can add value beyond just providing capital.

Slide 1 (Cover Slide): "10 Crucial Insights Every Innovator Should Know from Roy Rubin's Journey" Slide 2: "Embrace Open-Source" Harness the benefits of open-source technology as it can give you a unique edge while reducing risk and cost. Slide 3: "Prioritizing Innovation" Focus on internal resources to unveil hidden ways to innovate instead of copying pre-existing technologies. Slide 4: "Transparency Matters" Build a large following pre-launch by engaging with the community and being honest about your product. Slide 5: "Customer Support" Identify when partners are outperforming you in customer support; pivot your approach accordingly. Slide 6: "Enterprise Pivot" Consider adapting your product offerings to cater to larger, enterprise clients to maximize revenue. Slide 7: "Mastering Complex Products" Complex products can present challenges, but they also provide opportunities for deeper technical comprehension and innovation. Slide 8: "Value in Incomplete Ideas" A seemingly incomplete idea or team can potentially become a game-changer. Look for hidden opportunities. Slide 9: "Technical Debt Management" A robust template engine can allow easy customization without incurring technical debt, hence facilitating scale. Slide 10: "Embrace Change" Especially with technological advancements, accept the inevitability of change and learn to adapt swiftly. Slide 11 (CTA): "If you enjoyed these insights, tune in to DTC POD for more invaluable lessons from industry leaders like Roy Rubin!"

1. Every innovation has a "pocket calculator" moment--that tipping point when a new technology goes from controversial to indispensable. Utilize tech for value before it becomes just another commodity. 2. Open source doesn't mean inferior. Our build and finish garnered no small wonder from the tech circle. Surprises can come from anywhere! 3. Your partners may become your competitors, but that just means it's time to pivot and redefine your game. We can turn rivals into inspirations. 4. We’re not just an open-source entity, we're a community. Through gathering ideas on our blog, we have shaped an amazing product together. 5. Sometimes the key to innovation is looking internally, not externally. Magento sprung from a shift in perspective towards our own resources. Discover your own power. 6. An operator mindset can turn any incomplete idea into an opportunity. We see potential in the incomplete - the rough edges often hide the diamonds. 7. Building the perfect product for an imperfect market can be quite the adventure. We're reshaping booking experiences for campgrounds through innovation. 8. We're more than just a source of capital at RSquared Ventures. We strive to be an extension of your team, actively helping evolve ideas into real-world solutions. 9. A breakthrough in the AI space is not far off. Look for the innovators who are hard at work turning AI dreams into a scalable reality. 10. The journey from an UCLA dorm room to a billion-dollar industry was not easy. We built Magento as students learning PHP, and today we shape the way online business is conducted globally.