Sahil Lavingia is CEO of Gumroad and author of The Minimalist Entrepreneur. Many of our recent guests are recently-forged pioneers in the creator economy space, but Sahil has been building the passion economy since before it was cool. In 2011, Sahil founded Gumroad to help creators sell content directly to consumers. He was 19 at the time.But this episode isn't strictly about the passion economy, though we do chat about ideas like gatekeepers and shifting creator incentives. Much of today's discussion is Sahil reflecting on his ambitions to build a billion dollar company.Though Gumroad today is widely used by creators of all different sizes, its success story is not without growing pains. A decade ago Sahil raised venture-backed money to try to scale Gumroad at light speed. He details the lessons he learned trying to keep up with the aggressive timeline of venture capital firms. For better or for worse, he found that Gumroad only grew as quickly as the market determined they would grow. Now, Sahil fancies himself a "minimalist entrepreneur." He elaborates on what that means in today's episode and in his new book.For full show notes, links, RSVPs to live podcast recordings and more, visit thedeepend.substack.com

Tina He is an investor with Pace Capital and is also on the founding team at Station - which bills itself as building the rails for web 3. Her work with Pace & Station has helped her identify the myriad mental shifts that builders need to make when migrating from web 2 to web 3.Today's conversation is about those mental shifts. For example, the legal infrastructure that exists today has not caught up to technology's most recent community-organizing abilities. As DAOs gain more credibility and sophistication, there will also need to be clearer distinctions made between companies and communities. Contracts will look different too. Will employees and 1099 contractors have the same kind of benefits as community contributors?Tina also breaks down human-centric ideologies of web 3. The most talented builders are asking how we might redistribute value to the long-tail, as opposed to the FAANG behemoths who own so much of the overall value in web 2.The language we use in web 3 moving forward matters. This conversation with Tina helps us understand what some of these guiding rails can be.For full show notes, links, RSVPs to live podcast recordings and more, visit thedeepend.substack.com

Recently, many of our guests have been pioneers in the web3 space. Patrick Rivera provided a particularly helpful framework for understanding different eras of the web when he was on the show. From him, and other guests like Cooper Turley, we've learned that web3 is special because it enables users to have ownership of their different networks. Today's guests share the optimism of our past guests, but also note that the web3 is still in its infancy and is very much a work in progress.Those guests (Clarke & Jeff McKinnon) are building what they call "the reusable web." Like past guest Peer Richelsen, they believe that the internet works best when it's open-sourced and composable. To that end, yesterday they launched "The.com" to make it simple for website builders to create, 'remix,' and launch websites while getting paid and earning credit for their work.This is one of our favorite episodes we have ever done. We were struck by the balance that the McKinnon brothers are able to find between practicality and optimism. We'll be following along closely as they strive to live up to the ubiquity of their new domain.For full show notes, links, RSVPs to live podcast recordings and more, visit thedeepend.substack.com

A few weeks ago, our show carried a special announcement that On Deck had raised a $100 million fund to fuel the next generation of entrepreneurs. Swapstack, cofounded by Jake Singer & Jake Schonberger, is the first company to be accepted into an ODX cohort and receive a check for $125k check from the fund.Swapstack is positioned to be the premier newsletter advertising marketplace, connecting brands with writers to help the latter be able to become full time creators. The inbox, as the Jakes claim, is an intimate space. Newsletter creators want to make sure that they choose advertisers that align with their content so as to not pester their audience and risk losing carefully cultivated trust.This was a well timed conversation. It follows our discussion with Josh Kaplan about Creator Operators and builds off of last month’s discussion with Nathan, who runs a newsletter bundling company. We get into the nitty gritty of the newsletter business specifically. Swapstack wants to build the backbone for creator monetization and is well timed to assist a booming newsletter industry. We chat about the incentives of feed-based ads, how paywalls can lock creators into a restricting cadence,  and about the metrics that matter most when writers are first getting started.In addition to sharing a first name, both Jakes also are former On Deck employees where they were working on Swapstack as part of On Deck's creator offerings. Through that lens, we chat about intrapreneurship as both Jakes are able to lean on past innovative experiences they have had at other tech companies, including Facebook and Amazon. For more information about ODX, please visit beondeck.com/xFor full show notes, links, RSVPs to live podcast recordings and more, visit thedeepend.substack.com

Primer cofounders Ryan Delk & Maksim Stepanenko join the Deep End after meeting through On Deck. They are currently building a community for curious and ambitious kids to find and explore their interests together.Education is deeply personal, and so our conversation begins on a personal note, with a discussion of Ryan's background growing up homeschooled & Maksim's experience with highly structured curriculum back home in Kyrgyzstan.Both of them look back on their own learning experience and lament an education system designed with the  assumption that all children should move at the same pace. Kids' talents & interests vary wildly. Ryan and Maksim came to the realization  with Primer that they could build educational treadmills for kids to run as fast or as slow as they would like towards their particular interests. Our conversation centers on how to augment the education system to create more Michaelangelos and Albert Einsteins. How might we enable self-guided homeschooling without total involvement from parents? How can we leverage the dynamics of popularity to make learning cool?The kids that Ryan & Maksim are working with so far are incredible. They have a huge sense of ownership of their online community and are naturally creating governance protocols that limit toxicity and bullying. They're making friends and collaborating on projects, all while learning at a clip that outpaces traditional K-12 school.For full show notes, links, RSVPs to live podcast recordings and more, visit thedeepend.substack.com

Today conversation with Stephen Sikes (COO of Public) is about how millions of Americans are entering the stock market for the first time with mindsets and behaviors unlike any generation that has come before. New investors, particularly those who have started recently via a mobile app, believe they're part of a movement that's making investing more inclusive and accessible.Public exists to help these people get started investing and become better, more thoughtful investors too. In that vein, we talked about how to build community through investing, how to build financial literacy especially in regard to meme stocks, and the benefits of fractionalization.Stephen labels the stock market as the greatest wealth creation engine ever known to humanity, but we also examine that statement through the lens of crypto markets over the last decade. Stephen's built much of his own success through good timing - he started investing when the market was at a low point during the financial crisis in '07-08. We draw parallels between that opportune moment and the one that many others found themselves in last year during the height of lockdown.One huge difference between those two moments? The number of folks who are empowered to invest has skyrocketed. The implications of that and more ahead in today's episode.For full show notes, links, RSVPs to live podcast recordings and more, visit thedeepend.substack.com

Nathan Baschez joins the Deep End to discuss the passion economy, the realities of building a media business, and gets real with Marshall about  the realities of embarking on the founder journey as a creator. The two also chat about Every, which Nathan describes as a writer collective for productivity, strategy, leadership, & culture.This conversation with Nathan blends a few different threads that we've covered on The Deep End. Nathan's background as a prolific writer & podcaster makes this a natural extension of the conversation that we covered when discussing Creator-Operators with Josh Kaplan two weeks ago. We chat about the wavering stability of media companies and the obvious upside of the substack economy to creators. We ruminate on questions like “Should writers try to become stars in their own right?” and “What did early millennial-centric media businesses get wrong?” while examining how ambitious people often are replicating their behavior based on the models that have proven to be successful.The episode also echoes some of what we chatted about with Saagar Enjeti when we discussed the challenges & benefits of going independent. Nathan thinks that the fact that creators can reach fans more directly than ever before is to the passion economy what the shift to mobile was for tech.Finally, right after having Dr. Anhalt on the show to discuss mental health, Nathan & Marshall do some therapizing of their own as we discuss the day to day realities of the creator journey and how it affects us on a personal level.For full show notes, links, RSVPs to live podcast recordings and more, visit thedeepend.substack.com

Joining the Deep End is Doug Ludlow, CEO of Mainstreet. Today's conversation is about the unbundling and re-bundling of the smart bank and how the 35 million small businesses in the US can benefit from aggregating their business identity data in one place.We talk about helping small businesses navigate PPP loans during COVID, discuss how startups can earn tax credits easily for things like research & development and other ways that  Mainstreet can help restore America's economy coming out of the pandemic.Doug was a particularly fascinating guest because he has spent his life between two worlds. There's the tech world, where he's been a senior employee at Google, AOL, and other iconic tech companies, and then there's the world of his upbringing: he grew up in a small, rural   USA town t where farmers have been seeing  their land get consolidated and sold off. His unique perspective led us to chat about the brain drain among US heartland cities and how the rise of remote work might enable talent to stay in more rural communities where they grew up.For full show notes, links, RSVPs to live podcast recordings and more, visit thedeepend.substack.com

At On Deck, we believe that startups are the building blocks of a better future. Startups drive global economic growth by creating jobs, improving quality of life, and making meaningful progress to solving society's biggest problems. We also believe that the the biggest constraint on startup creation is the number of founders - for each person starting a company today, there are hundreds more sitting on the sidelines. This is an enormous waste of human potential.That's why we are excited to announce ODX - a $100 million community-backed fund to put the next generation of founders in business.ODX backs founders with a check for $125,000 and unlimited access to the On Deck network, which includes thousands of companies, founders, operators, and investors that builders can tap into for talent, capital, and distribution. Many of those investors & operators are also participants in the community-backed fund, meaning that they are personally incentivized to help ODX participants succeed.ODF - our original founders fellowship - will continue to exist under the On Deck umbrella, but will now be free for those accepted. ODF and ODX are interlinked programs, separated by a key difference: conviction. ODF is for prospective founders who are in more of an exploratory phase. They are likely researching markets, validating an idea, hunting for a cofounder, or leveling up founder skills. ODX will be for those 100% ready to take the plunge and start a company.Both programs will exist as part of On Deck's global network of networks. Erik & David join the show to discuss their belief that Silicon Valley is no longer a physical location, but a mindset. On Deck captures the essence of Silicon Valley - an abundant system of talent, capital, & ideas, and makes it available for an internet-native era. Our conversation today speaks to these big ideas and dives into the exciting details of ODX and the many other programs & communities that make up the On Deck ecosystem.For full show notes, links, RSVPs to live podcast recordings and more, visit thedeepend.substack.com

Joining Marshall in the Deep End is Sara Du - cofounder & CEO of Alloy Automation,  a no-code tool for automating e-commerce stores.The conversation begins by discussing how the line between commerce and e-commerce is blurring as e-commerce penetration continues to accelerate across the consumer economy.  This trend was certainly accelerated by the pandemic, but Sara notes that Black Friday shopping patterns and other indicators suggest that such a shift was inevitable anyways.The discussion then moved  to the power of no-code tools, and their potential applications to helping unlock value for  small businesses without engineering teams. Sara thinks that Alloy can be for commerce what Zapier has been for tech.Finally, we discussed the implications of automation itself. Does it replace jobs or augment current ones?For full show notes, links, RSVPs to live podcast recordings and more, visit thedeepend.substack.com