The Capital Stack

David Paul
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Early growth investor David Paul interviews the world’s greatest founders, operators, and investors. Get an insider’s look into the tech ecosystem, learn how to start and scale your own business, and find an edge in today's capital markets.

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    Greg Head of Scaling Point on Changing Startup Funding and Drawbacks of Venture Capital Funding

    In this conversation, venture capitalist David Paul and Greg Head of Scaling Point discuss the changing landscape of funding for startups. They explore the drawbacks of relying on venture capital (VC) funding and the benefits of bootstrapping and practical founder approaches. Greg emphasizes that VC funding is not necessary for success and that there are multiple paths to building valuable software companies. They also discuss the role of private equity in acquiring SaaS companies and the importance of profitability in the growth game. Greg offers advice to founders and invites them to connect with him for further guidance. You can watch/listen to the podcast on YouTube, Spotify, and Apple. Takeaways VC funding is not necessary for building valuable software companiesBootstrapping and practical founder approaches can lead to successPrivate equity plays a significant role in acquiring SaaS companiesProfitability is crucial in the growth gameThere are multiple paths to success in the startup world Sound Bites "VC funding should be used in small doses only when it's really appropriate, like opioids.""VC funding is usually misunderstood by founders and overprescribed by big investors.""Getting to product market fit is the universal problem, whether you are funding it yourself or out of a service business or have a little angel funding or get to customer revenues." Chapters 03:08 The Changing Landscape of Startup Funding 09:15 The Drawbacks of Venture Capital Funding 15:37 The Benefits of Bootstrapping and Practical Founders 27:31 The Importance of Profitability in the Growth Game 29:13 Multiple Paths to Success in the Startup World

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    Dan Soviero of Signature Lacrosse on Over-Investing in Culture and Streamlining the Ordering Process

    Dan Soviero, founder of Signature Lacrosse, shares his entrepreneurial journey and how he built a successful sports equipment and events company with venture capitalist David Paul. He discusses the importance of hard work, discipline, and doing what you love. Dan explains how Signature Lacrosse expanded its offerings to solve the biggest problem in youth sports: ordering custom uniforms. He highlights the role of technology in streamlining the ordering process and improving the customer experience. Dan also shares his vision of getting more kids involved in sports and the impact his company is making in the industry. You can watch/listen to the podcast on YouTube, Spotify, and Apple. Takeaways Hard work, discipline, and doing what you love are key to building a successful business.Solving the biggest problem in your industry can lead to significant growth and impact.Technology, such as custom software, can streamline processes and improve the customer experience.The goal should be to get more kids involved in sports and provide them with a positive experience.Over-investing in culture and aligning the team around a shared vision can lead to a great workplace. Sound Bites "My dad was really big on us paying rent to stay at his house and to eat his food from a pretty young age. He kind of pushed us into the entrepreneurial spirit.""We have such a fulfilled life and so much fulfillment in every single day because we're doing what we love and we're making the impact that we want to make every single day.""Cash conversion cycle is king. Revenue is vanity, net income is sanity, and cash is reality." Chapters 00:00 The Signature Lacrosse Journey 19:06 Solving the Biggest Problem in Youth Sports 26:53 Tech-Enabling the Ordering Process 30:51 Lessons Learned and Impacting Youth Sports

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    Jon Corrin of Xilo on Strong Onboarding Processes and Pipeline Automation in the Insurance Industry

    In this conversation, David Paul interviews Jon Corrin, the co-founder of Xilo, a vertical SaaS company in the insurance industry. They discuss topics such as pipeline management, the evolution of the insurance industry, Xilo's value proposition, and their market segmentation. Jon shares insights on the importance of product development, the role of instinct in decision-making, and the significance of a strong onboarding process. He also talks about the fundraising journey and the qualities he looks for in investors. The conversation concludes with a discussion on the best business advice Jon has received and his favorite book, 'The 33 Strategies of War' by Robert Greene. You can watch/listen to the podcast on YouTube, Spotify, and Apple. Takeaways Pipeline management is crucial in the insurance industry, and Xilo has focused on automating processes and improving operational metrics to increase pipeline.Xilo's value proposition lies in providing a great customer experience on the form submission side and automating workflows into legacy back-office software.Jon emphasizes the importance of listening to customers and using instinct and gut feelings to make decisions as a founder.A strong onboarding process is essential for customer success, and Xilo provides one-on-one onboardings for each user to ensure a smooth experience.When seeking investors, Jon looks for those who can provide access to capital, talent, and customers.Jon recommends 'The 33 Strategies of War' by Robert Greene as a compelling book that combines history and business advice. Sound Bites "It's 6X what it was in Q4. So we're doing well.""You know, there are so many facets to that because I didn't come from the insurance industry.""I'm definitely the type of person that can create a funnel, handle all the operational metrics." Chapters 00:00 Introduction and Podcast Room Banter 02:10 Pipeline Management and Xilo's Growth 06:41 Xilo's Value Proposition and Automation in the Insurance Industry 10:46 Xilo's Target Market and Growth Potential 15:33 Fundraising and Investor Criteria 23:48 Creating a Strong Onboarding Process 26:05 Book Recommendation: 'The 33 Strategies of War'

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    Krista Morgan of Stage Fund on Investing in Failed Startups and Navigating Distressed Assets

    Krista Morgan, General Partner at Stage Fund, joins venture capitalist David Paul to discuss their unique approach to investing in early-stage technology companies that are unable to raise more funding. Stage Fund focuses on control acquisitions and provides a second chance for struggling companies by offering new capital and a new path forward. They often acquire distressed assets and work closely with founders to turn the companies around. Krista emphasizes the importance of alignment, accountability, and operational expertise in the success of these companies. She also discusses the challenges and opportunities in the emerging asset class of early-stage private equity. You can watch/listen to the podcast on YouTube, Spotify, and Apple. Takeaways Stage Fund specializes in control acquisitions of early-stage technology companies that are unable to raise more funding.They provide struggling companies with a second chance by offering new capital and a new path forward.Alignment, accountability, and operational expertise are crucial for the success of these companies.The emerging asset class of early-stage private equity offers opportunities for new investment strategies and approaches. Sound Bites "We are a control investor, making control acquisitions of early-stage technology companies that are unable to raise more funding.""The number of calls I get where people think they're at that place of getting a hard deal done, but actually being there are two very different things.""We really like finding value in the chaos. Like I like chaos." Chapters 03:13 The Stage Fund’s Approach to Investing 07:11 Challenges in Getting Deals Done 12:53 The Importance of Alignment and Accountability 25:31 The Future of Early-Stage Tech Investing

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    Nathan Firth of NewRocket on Finding Success in Niche Markets and Productizing Services

    Nathan Firth, founder and CEO of New Rocket, founder of LaunchPad San Diego, and current CCO of ShareLogic shares his journey as an entrepreneur and the success of his tech-enabled service company with venture capitalist David Paul. He emphasizes the importance of finding a niche market and specializing in one thing to become the best at it. Firth discusses the benefits of being a tech-enabled service company and how they productize their services to increase efficiency and deliver more value to customers. He also talks about the challenges of scaling a company and the lessons he learned along the way. Firth is now exploring new opportunities and investing in startups. You can watch/listen to the podcast on YouTube, Spotify, and Apple. Takeaways Finding a niche market and specializing in one thing can lead to success as an entrepreneur.Productizing services can increase efficiency and deliver more value to customers.Scaling a company comes with challenges and requires careful allocation of resources.Exploring new opportunities and investing in startups can lead to new ventures and growth. Sound Bites "Find a niche market, specialize, and be the absolute best at doing that one thing.""Productizing our services made us more efficient and allowed us to deliver more value to customers.""Finding the right balance in company size can maintain agility and a startup culture." Chapters 06:10 The New Rocket Story 08:03 Niche Market and Productization 14:01 Lessons in Scaling a Company

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    Quentin Wendt of PadSplit on Achieving High Real Estate Returns via Technology Disruption

    In this conversation, David Paul interviews Quentin Wendt from PadSplit, a prop-tech company that allows investors to rent out single-family homes by the room. They discuss the housing crisis, the need for affordable housing, and how PadSplit provides a solution by adding density to single-family homes. Quentin explains how the platform works, with members going through a background check and income verification to become approved tenants. The platform handles demand aggregation, collections, and communication between members and investors. They also discuss the hesitation and pushback from investors and municipalities, as the concept of shared housing is still relatively new in the US. PadSplit offers a unique model for real estate investors to generate high returns and scale their businesses quickly. By converting single-family homes into shared living spaces, PadSplit provides affordable housing for essential workers and generates more cash flow and tax benefits compared to traditional rental properties. The company aims to solve the problem of affordable workforce housing and offers a faster and more profitable alternative to traditional real estate investments. PadSplit's model appeals to both investors and tenants, providing a win-win solution for all parties involved. Takeaways PadSplit is a prop-tech company that allows investors to rent out single-family homes by the room, providing a solution to the housing crisis and the need for affordable housing.The platform handles demand aggregation, collections, and communication between members and investors.There is hesitation and pushback from investors and municipalities due to the unfamiliarity of shared housing in the US.PadSplit's model allows investors to add density to single-family homes, increasing revenue and providing affordable housing options for low-income individuals.The platform is still in its early stages, but early adopters are finding success and building portfolios of income-producing properties. PadSplit offers a unique model for real estate investors to generate high returns and scale their businesses quickly.By converting single-family homes into shared living spaces, PadSplit provides affordable housing for essential workers.PadSplit generates more cash flow and tax benefits compared to traditional rental properties.The company aims to solve the problem of affordable workforce housing and offers a faster and more profitable alternative to traditional real estate investments. Chapters 03:44 Introducing Quentin and PadSplit 07:30 What is PadSplit? 09:23 The Housing Crisis and Affordable Housing 12:02 Challenges in the Real Estate Market 20:13 Hesitation and Pushback in the Market 23:58 How the PadSplit Platform Works 26:06 The Importance of Property Managers 26:43 PadSplit: A Unique Model for Real Estate Investors 29:56 Solving the Problem of Affordable Workforce Housing Sound Bites "PadSplit is a five-year-old startup that allows investors to take single-family houses and add density by renting by the room.""PadSplit has almost 12,000 units across 20 markets in the country, and our hockey stick curve is starting.""PadSplit is a cashflow machine that allows investors to offset negative cashflow from other real estate investments.""It's a really fast way to scale your business because the returns are typically 2 and 1 half to 3 times returns on a normal long-term investment.""Does it break

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    Matt Ekstrom on the Evolution of HR Tech and Challenges of Outbound Sales

    In this conversation, David Paul and Matt Ekstrom - an executive with over 10+ years in sales and marketing within the HR tech space discuss various topics related to HR tech, sales enablement, and the challenges faced in these industries. They talk about the evolution of HR tech and its impact on employee onboarding and hiring experience. They also discuss the parallel between sales enablement and HR tech, the challenges of outbound sales, and the future of email marketing. Matt shares his favorite book and the best piece of business advice he has received. You can watch/listen to the podcast on YouTube, Spotify, and Apple. Chapters 00:00 Introduction and Cold Open 08:07 The Parallel Between Sales Enablement and HR Tech 12:01 The Challenges of Outbound Sales 16:00 The Future of Email Marketing Takeaways HR tech has not significantly improved the employee onboarding and hiring experienceThe HR tech industry continues to fracture and expand with new companies and solutionsSales enablement tools and strategies are evolving, with a focus on content creation and audience targetingThe future of sales is uncertain due to email deliverability challenges and the need for new outreach methodsKnowing what you don't know and being humble about it is important in business Sound Bites "No, no, absolutely not. And I don't, I really don't sit this at the feet of the entrepreneurs or those companies necessarily.""The technology can only do so much for that experience. It's up to the recruiters as well and the hiring managers to put the effort in as well.""The inbound method is no longer a thing, right?"

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    Seth Merritt of Welby Health on Value Based Care Challenges and having the right Capital Mindset

    In this conversation, David Paul interviews Seth Merritt, the founder of Welby Health, about value-based care in the healthcare industry. They discuss the challenges of implementing value-based care initiatives, the need for innovation in the healthcare system, and the difficulties faced by providers and payers. Seth shares his journey as an entrepreneur and the lessons he learned about raising capital and finding the right investors. Overall, the conversation highlights the complexities of the healthcare industry and the importance of finding solutions that work for both providers and payers. In this conversation, Seth Merritt discusses his experience with raising capital and the challenges of managing money in a startup. He emphasizes the importance of delivering value to investors and being thoughtful about the use of capital. Seth also shares his perspective on the changing dynamics of the market and the need for startups to focus on profitability and differentiation. He highlights the importance of stewardship and the long-term commitment required in the startup journey. Seth concludes by discussing his excitement about the future of his company, Welby Health, and the opportunities for growth and scaling. You can watch/listen to the podcast on YouTube, Spotify, and Apple. Takeaways Implementing value-based care initiatives is challenging due to the complexities of the healthcare system and the resistance to change.Innovation in healthcare is necessary to improve patient outcomes and reduce costs, but it requires understanding the nuances of the industry.Finding the right investors and partners is crucial for the success of a healthcare startup, as they provide not only capital but also guidance and support.The healthcare industry needs solutions that work for both providers and payers, considering their different needs and constraints. Delivering value to investors is crucial in the startup journey.Being thoughtful about the use of capital and focusing on profitability are essential for long-term success.Differentiation and demonstrating real value are more important than just having a great idea or pitch.Stewardship and a long-term commitment are necessary to navigate the challenges of the startup world.Scaling a startup requires managing costs, finding the right talent, and charging what the company is worth. Sound Bites "We were dealing with a lot of health systems and larger providers and administrative pieces of the organization versus the individual doctor working in his office and the patient who has hypertension and diabetes, they were just sort of like numbers on a chart.""Everyone complains about healthcare spending, but no one's really putting their money where their mouth is, you know, and trying to do anything about it.""You're asking doctors on their 2% margin to go pay for something else, even if it's the best thing ever, it's just not gonna happen.""The only thing contractually that VCs have to do is why are you money?""Sometimes you just need the person that believes in you, right? Even if it is a dick.""This idea is actually real. That gave me like a little bit of push." Chapters 07:22 The Need for Innovation in...

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Early growth investor David Paul interviews the world’s greatest founders, operators, and investors. Get an insider’s look into the tech ecosystem, learn how to start and scale your own business, and find an edge in today's capital markets.

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    David Paul
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