Joining us today in the Deep End is Lauren Self. Lauren is the founder of Roots Homes, a fractional home ownership company, that allows you to build equity in your home while paying rent, which recently raised a $2.2M seed round. In this conversation we explore how Roots is finding the missing middle between renting and buying, helping ensure home-ownership comes with flexibility and how Roots is increasing access to the American dream. ---- View the full series on Housing: https://www.beondeck.com/deep-end/housing

Joining us in The Deep End today for our housing series is Kim-Mai Cutler, a partner at Initialized who invests in proptech, real estate, and climate. Kim's background as a financial markets reporter and early-stage venture startup enthusiast, allowed her to broaden her reporting to include the intersection of the industry and public policy. In 2014, her essay on TechCrunch titled "How Burrowing Owls Lead To Vomiting Anarchists (Or SF’s Housing Crisis Explained)" sparked almost a decade of public advocacy that changed a number of state laws in California around housing and zoning. As our first guest for this housing series, it’s only fitting that we invited Kim to help us understand why housing is a key problem worth solving, what are the implications around the current state of things, and what different bottlenecks founders can work on. We hope this conversation will give you a nuanced understanding of a complex market and practical tactics for building in housing.

Over the past two years, we've interviewed 100+ people for our podcast, The Deep End. Now we're relaunching The Deep End as a multi-media publication, focused on problems worth solving. In the first series, we are tackling an issue that affects us all: access to housing. Our house provides us with a sense of belonging and serves as a sanctuary where we can retreat from the chaos of the world. Once we accept the importance of housing, our focus needs to shift to how we can make it more accessible. We kick off the series with an introduction to housing as a problem. We look into why it's a problem worth solving and what are the bottlenecks to doing so – technology, culture, regulation, and more. Then, over the next few weeks, we talk to Lauren Lorraine Self from Roots Homes, Kim-Mai Cutler from Initialized, Will Jarvis from ValueBase, Peter Light from Lumen Energy and Riley Meik to understand the bottlenecks to housing, and explore possible solutions. Through this, we try to form a mental map of the problem: understanding its societal importance, the current bottlenecks to progress and setting out some of the most impactful solutions. In doing so, we hope to give the audience the tools and knowledge to build, invest or support some of the solutions to these challenges. Housing is not an easy problem to solve, but we believe it is a problem worth solving. So let’s get going. Episodes notes and more: https://beondeck.com/deep-end/housing

Joining us in The Deep End today is Vignan Velivela. Vignan is the co-founder and CEO of AtoB, a fintech payments platform modernizing the trucking industry’s financial system, which raised a $155M Series B last year. He was also a part of the On Deck Founders’ third cohort. We are taking a short break from our series on access to housing, to talk to Vignan about one of the biggest challenges facing us at the moment: transportation and logistics. In this episode, we cover the central and essential role of trucking in America’s economy, why the trucking industry’s financial systems were ripe for disruption, how far away we are from self-driving trucks, and what the future of transportation looks like in the coming years.

Joining us in The Deep End today is Tory Reiss. Tory is the CEO and co-Founder of Equi, an alternative investment hedge fund. Tory previously co-founded Archblock, a decentralized alternatives marketplace, and Harvest Money, an AI-driven debt management platform. We’re taking a quick break from our series on starting companies, to take a quick dive into the world of fintech. Our conversation with Tory today centers around how you can take control of your financial destiny and Tory’s journey from a Google Docs to starting Equi.

Navigating the Idea Maze to The Unlikely Birth of FinchFinch, a platform providing a unified API for employment data, was born out of failure and uncertainty. Ansel Parikh and Jeremy Zhang, the co-founders, first met during On Deck's second cohort. Both were passionate about solving the plumbing behind big problems and gravitated towards challenging infrastructure issues.Finch was born out of failure. Initially, they attempted to launch an embedded lending platform, but the COVID-19 pandemic disrupted their plans. Banks and customers began rejecting them as the future of lending became uncertain. Who was going to give a loan in such an uncertain environment? It wasn't until a small business lender they were potentially going to work with approached them with a request to help access employment data for the Payment Protection Program (PPP) that they discovered the opportunity that would eventually become Finch.Although the PPP was nearing its end when they built their solution, Ansel and Jeremy received enough positive feedback to continue pursuing the employment data problem. They embraced a "hard to get information made legible" business model, rather than following a thesis-driven approach. This allowed them to quickly pivot and adapt based on their unique founder-product fit: Ansel's background in fintech and infrastructure investments, combined with Jeremy's engineering and product experience, enabled them to quickly develop a product and secure their first customer. They emphasized the importance of failing quickly and focusing on the problem, rather than falling in love with a particular solution. Ansel also highlights that there is no “perfect moment” to get to conviction, you just need to make a decision.Finding the Right Co-FounderFor Ansel and Jeremy, finding the right co-founder was critical to their success. On paper, they had a unique founder / product fit.Jeremy had a background on engineering and product, and had worked on API challenges before that transferred to employment data ecosystems and the work they were doing at Finch.Ansel had been a late-stage investor at Kleiner Perkins and had spent a considerable amount of time on fintech and infrastructure investments so he was deeply familiar with the space.That said, they had to test whether they actually worked well as a team. They recommend setting up a three-week sprint with a potential co-founder to work on a project together, setting daily goals, and discussing progress. On top of that, they found another co-founder team who were going through the same stage and became accountability buddies. In their case, On Deck played a crucial role in helping them meet and build a strong working relationship because it provided with the structure they needed throughout that period.Embracing Complexity and Turning Illegible Information into Legible DataFinch's business model revolves around transforming illegible, hard-to-find information into legible, connected, and programmable data. The challenge of building a single source of truth for employer-employee relationships lies in the uniqueness, obscurity, and hyper-dynamic nature of these connections.Employment relationships vary significantly across industries and sectors, with different structures and incentives. Blue collar vs. White collar is not the only distinction. As an example, startup employees value equity, other type of non-tech companies value benefits, and factory workers value overtime.Moreover, employment data is often hidden in obscure systems that don’t communicate with each other, making it difficult to access. Adding to the complexity, this information is continuously changing, and outdated data is often used for critical decision-making at various levels.The US tax system and the US employment rules are a nightmare. There are different tax brackets and regulations at a city, state and federal level, and they also vary across industries. By focusing on making illegible information legible and valuable, the company offers a playbook for others looking to build successful businesses in the face of adversity.

Gina Gotthilf is the co-founder and COO at Latitud, a platform helping build the next generation of iconic tech startups in Latin America through products, a dedicated fellowship and fund. Gina met her co-founder, Brian Requart, through On Deck. Before Latitud, Gina was the VP of Marketing and Growth at Duoloingo, helping scale the company from 3 to 200 million users, and worked on the Mike Bloomberg presidential campaign. Continuing with our series on the meta-problem of helping people start companies, we talk to Gina about the bottlenecks to starting companies outside the United States.

Joining us in The Deep End today is Sophie Alcorn. Sophie is the founder of Alcorn, a Silicon Valley immigration law firm that helps tech talent immigrate to the US. She is also the host of the podcast Immigration Law for Tech Startups and author the TechCrunch weekly immigration advice column “Dear Sophie.” Continuing with our series on the meta-problem of helping people start more companies, we talk to Sophie to understand why immigration is a bottleneck to company creation, and what founders, investors, and policy-makers can do about it.

On The Deep End today, we welcome Sasha Orloff, the Founder and CEO of Puzzle, a modern accounting software package for startups that recently raised $15 million in series A. Sasha joins us to discuss the use of accounting as a powerful decision-making tool and the creation of infrastructure to start and scale businesses, as part of our series on meta-problems to help founders start more companies. Despite advances in financial technology, Sasha believes that core accounting software remains outdated and does not take advantage of modern capabilities. He suggests that accounting could be a competitive advantage for businesses if it were reimagined as a tool for data-driven decision-making, empowering founders to build better businesses. During the episode, Sasha identifies three key areas that founders should focus on when fundraising: telling a compelling story, taking the process seriously, and planning for success: Founders must have a strong answer for what sets them apart from their competitors, and they should be intentional about raising venture capital. As the market returns to normal, Sasha advises founders to be aware of business compliance and financial diligence to avoid giving away a larger percentage of their company for less money. Throughout the episode, he emphasizes the importance of founders understanding their business numbers to make informed decisions and build successful companies. You can learn more about Puzzle at https://puzzle.io.

Joining us on the Deep End today is Minn Kim. Minn spent a few years as an investor at Ridge, Bloomberg Beta and On Deck, backing founders as early as possible and is now building Plymouth to help extraordinary talent immigrate to the US. In this conversation we go deep into Minn’s core belief – that technology enables step changes in human agency. We discuss navigating the idea maze, picking who to start a company with, why immigration is key to innovation and so much more.