The Capital Stack

David Paul

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. read less
TechnologyTechnology

Episodes

Nathan Firth of NewRocket on Finding Success in Niche Markets and Productizing Services
6d ago
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.TakeawaysFinding 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."Chapters06:10 The New Rocket Story08:03 Niche Market and Productization14:01 Lessons in Scaling a Company
Quentin Wendt of PadSplit on Achieving High Real Estate Returns via Technology Disruption
May 6 2024
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.TakeawaysPadSplit 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.Chapters03:44 Introducing Quentin and PadSplit07:30 What is PadSplit?09:23 The Housing Crisis and Affordable Housing12:02 Challenges in the Real Estate Market20:13 Hesitation and Pushback in the Market23:58 How the PadSplit Platform Works26:06 The Importance of Property Managers26:43 PadSplit: A Unique Model for Real Estate Investors29:56 Solving the Problem of Affordable Workforce HousingSound 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
Matt Ekstrom on the Evolution of HR Tech and Challenges of Outbound Sales
Apr 30 2024
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.Chapters00:00 Introduction and Cold Open08:07 The Parallel Between Sales Enablement and HR Tech12:01 The Challenges of Outbound Sales16:00 The Future of Email MarketingTakeawaysHR 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 businessSound 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?"
Seth Merritt of Welby Health on Value Based Care Challenges and having the right Capital Mindset
Apr 23 2024
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.TakeawaysImplementing 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."Chapters07:22 The Need for Innovation in...
Nick Steinwachs of Tidal Digital Health Partners on Building Healthcare Products and Navigating Stakeholders
Apr 16 2024
Nick Steinwachs of Tidal Digital Health Partners on Building Healthcare Products and Navigating Stakeholders
In this conversation, David Paul interviews Nick Steinwachs about the challenges and opportunities in the healthcare industry. They discuss the importance of customer empathy, the role of founders in healthcare startups, and the need for innovative solutions. They also touch on the difficulties of commercializing healthcare products and the importance of market validation. Nick shares his insights on finding a product-market fit and navigating founder bias. Overall, the conversation highlights the complexities of the healthcare industry and the importance of understanding customer needs. You can watch/listen to the podcast on YouTube, Spotify, and Apple.TakeawaysCustomer empathy and subject matter expertise are crucial in building successful healthcare products.Commercializing healthcare products can be challenging due to regulatory issues and the need for buy-in from healthcare providers.Shifting the market conversation can be more effective than trying to retool a product that is not resonating with customers.Founders should listen to their market and be willing to let go of their solutions to address the real problems.Market validation is important, and founders should focus on usability, feasibility, viability, and value in their product development process.Chapters00:00 Introduction and Background02:26 The Importance of Customer Empathy08:21 Challenges in Commercializing Healthcare Products14:51 Shifting the Market ConversationKeywords- healthcare, startups, customer empathy, product-market fit, commercialization, market validation, founder bias29:12 The Role of Market Validation
Lisa Diaz of Turf Advisory on Construction Tech Software and the America's Infrastructure Tailwinds
Apr 9 2024
Lisa Diaz of Turf Advisory on Construction Tech Software and the America's Infrastructure Tailwinds
In this episode, David Paul interviews Lisa Diaz, the founder of Turf Advisory, about the construction industry and the need for infrastructure investment. They discuss the challenges of government prioritization, the role of general contractors and subcontractors, and the low margins in the construction industry. They also explore the potential of construction technology to increase margins and address pain points in the industry. Lisa emphasizes the importance of integrating and connecting different systems and the need for standardization in construction. She also shares her excitement about using digital twins for infrastructure assessment and the opportunity for infrastructure repair. You can watch/listen to the podcast on YouTube, Spotify, and Apple.TakeawaysThe construction industry is in need of infrastructure investment to address deteriorating infrastructure and meet the growing demand for housing and transportation.Government prioritization of infrastructure projects is influenced by politics and the most pressing needs, often resulting in a shortage of funding for necessary repairs and upgrades.Construction technology has the potential to increase margins in the industry by improving efficiency and addressing pain points such as labor tracking and material delivery.The adoption of construction technology faces challenges such as resistance to change and the need for standardization and integration among different systems.Chapters01:05 The Need for Infrastructure Investment03:09 The Importance of Infrastructure to Joe Biden04:15 Improving Infrastructure in New York City05:19 Bidding and Contracting in the Construction Industry06:13 Different Types of Construction and Contractors07:38 The Role of General Contractors and Subcontractors08:33 The Transition to Design-Build Contracts09:20 Low Margins in the Construction Industry10:17 Increasing Margins with Construction Technology11:46 The Challenges of Construction Technology Adoption13:02 Using Technology to Track Labor and Materials14:53 Addressing Pain Points in Construction16:15 The Importance of Integration and Connectivity19:12 Regulatory Changes and Pain Points in Construction20:40 Using Digital Twins for Infrastructure Assessment23:16 The Need for Standardization in Construction27:17 The Opportunity in Infrastructure Repair29:38 Contacting Lisa Diaz and Turf Advisory
Pete Colligan of Ariba on How to Hire Software Engineers and Change Management
Apr 2 2024
Pete Colligan of Ariba on How to Hire Software Engineers and Change Management
In this conversation, David Paul interviews Pete Colligan, the CTO of Ariba Business Networks. They discuss various topics related to leadership, innovation, and hiring in the corporate world. Pete shares his experiences and insights on structuring teams, driving innovation in a large company, navigating change management, and conducting effective interviews. He emphasizes the importance of building a strong team, setting clear goals, and creating a supportive onboarding process for new hires. Pete discusses his concerns and excitement in the world of technology, including the benefits of modern tools in coding productivity and the modern data stack. He also explores the challenges and opportunities in team building in the post-COVID era. The conversation touches on the importance of making choices in strategy and the ongoing debate between platforms and best-in-class solutions. Peter shares his recommendations for influential leadership books and resources, emphasizing the value of learning from leaders and building bridges to get things done. You can watch/listen to the podcast on YouTube, Spotify, and Apple.TakeawaysBuilding a strong team is crucial for success in any project or organization.Innovation in a large company requires curiosity, initiative, and the ability to build credibility and trust.Change management is essential when implementing new initiatives, and it involves creating a clear vision, aligning stakeholders, and setting expectations.Effective hiring involves being intentional about the desired culture and skills, using situational questions to assess candidates, and ensuring a smooth onboarding process.Modern tools incorporating breakthroughs in large language models can greatly enhance coding productivity.The modern data stack, including tools like Snowflake, offers easier data collection, transformation, and analysis.Team building in the post-COVID era requires understanding the impact of remote work and finding ways to maintain effective collaboration.Making choices and building bridges are crucial skills in strategy and leadership.Chapters02:10 The Importance of Team and Leadership05:27 Driving Innovation in a Large Company07:04 Structuring and Leading Complex Projects10:03 Navigating Change Management and Reputational Risk13:29 Effective Hiring and Onboarding25:03 Conducting Effective Interviews26:00 Areas of Concern and Excitement in Technology27:19 Benefits of Modern Tools in Coding Productivity29:15 Team Building in the Post-COVID Era30:27 Understanding the Data Stack34:21 Platforms vs. Best-in-Class Solutions38:32 The Importance of Making Choices in Strategy40:28 Learning from Leaders and Building Bridges
Vickram Pradhan of Sopris Capital on Decentralization in Healthcare and the Founder/Investor Relationship
Mar 26 2024
Vickram Pradhan of Sopris Capital on Decentralization in Healthcare and the Founder/Investor Relationship
Vickram Pradhan, an investor at Sopris Capital, joins venture capitalist David Paul to share his background and experience in investing, as well as his role at Sopris. He discusses the importance of building relationships with portfolio companies and providing operational expertise. Vickram also highlights the advantages of Sopris' capital allocation strategy and the flexibility it offers. He explores the growth of tech-enabled services in healthcare and the challenges of differentiating between tech-enabled services and SaaS companies. Vickram concludes by discussing the decentralization of healthcare and the increasing demand for personalized care and ownership of healthcare decisions. You can watch/listen to the podcast on YouTube, Spotify, and Apple.TakeawaysBuilding relationships and providing operational expertise are crucial in early-stage investing.Flexibility in capital allocation strategy allows for better alignment with portfolio companies.Tech-enabled services in healthcare offer opportunities for growth and disruption.The decentralization of healthcare and the increasing demand for personalized care are emerging trends.Reading quarterly letters from hedge funds can provide valuable insights into pricing risk and investment strategies.Chapters02:23 Background and Experience03:24 Foray into Investing and Role at Sopras Capital04:37 Relationship with Sopras Capital05:30 Investment Advice from Andy06:41 Navigating Challenges in Early Stage Investing07:14 Managing Anxiety and Frustration09:21 Founder Buy-In on Operational Expertise09:38 Differentiation in Capital Allocation Strategy14:34 Flexibility in Entry and Exit Strategies15:48 Challenges of Overcapitalization19:22 Tech-Enabled Services vs. SaaS22:52 Decentralization of Healthcare26:11 Shift in Healthcare Awareness and Ownership28:26 Demand for Additional Healthcare Tests30:10 Advanced Practice Providers in Healthcare32:23 Favorite Investors and Reading Recommendations
Jerry Colonna on Radical Self-Inquiry for Startup Founders and Investors
Mar 19 2024
Jerry Colonna on Radical Self-Inquiry for Startup Founders and Investors
Jerry Colonna, executive and life coach of Reboot.io, discusses the importance of personal growth and self-inquiry for startup founders. He shares his own journey of rebooting and how it led him to become a coach. Colonna emphasizes the need for founders to confront their own brokenness and take responsibility for their actions. He also explores the challenges faced by investors and the need for empathy and self-soothing in the startup ecosystem. Jerry Colonna discusses the state of investing and the need for a shift in focus from financial returns to building meaningful relationships. He shares the genesis of his work with Reunion and the importance of personal growth and being a better human. Jerry also explores the impact of systematic racism and oppression, as well as the fear of the other in society. He emphasizes the moral responsibility of business leaders to address these issues and create positive change. The conversation concludes with a discussion on the next iteration of Jerry's work and the importance of asking meaningful questions. You can watch/listen to the podcast on YouTube, Spotify, and Apple.TakeawaysPersonal growth and self-inquiry are essential for startup founders to navigate the challenges of entrepreneurship.Confronting one's own brokenness and taking responsibility for one's actions is a crucial step in personal growth.Investors should lead with empathy and self-soothe their own anxieties to create a healthy and supportive environment for founders.The startup ecosystem needs to address systemic issues and lower expectations to foster a more realistic and sustainable approach to entrepreneurship. Investing should focus on building meaningful relationships rather than solely pursuing financial returns.Personal growth and being a better human are essential for effective leadership.Systematic racism and oppression must be acknowledged and addressed.Business leaders have a moral responsibility to create positive change in society.Chapters03:20 Rebooting and Radical Self-Inquiry08:57 Reunion and Personal Growth16:05 The Importance of Painful Work25:15 The Role of Investors in Founder Dishonesty27:48 The Systemic Issues in Startup Culture29:09 The State of Investing30:06 The Importance of Relationships31:15 The Genesis of Reunion33:03 A Pointing Out Instruction34:29 Systematic Racism and Oppression36:00 Fear of the Other37:00 Radical Self-Inquiry and Leadership39:08 Attacking Ideologies and the Real Problems40:30 The Moral Responsibility of Business Leaders42:22 The Next Iteration of Jerry's Work
Al Doan of Missouri Start Quilt Company on Self-Destructive Founder Mindset and How to Overcome It
Mar 12 2024
Al Doan of Missouri Start Quilt Company on Self-Destructive Founder Mindset and How to Overcome It
In this episode, Al Doan, the founder of the Missouri Star Quilt Company turned investor at Rolling Fun, shares his journey as an entrepreneur and investor. He discusses starting the quilt company as a way to support his mother and how it grew into a successful business. He also talks about his transition out of the company and his ventures into tech startups, investing, and real estate. Al shares his passion for revitalizing small towns and his experiences as a founder, including the challenges and sacrifices involved. He emphasizes the importance of finding happiness and fulfillment beyond financial success. In this conversation, Al Doan discusses the importance of setting realistic goals and reflecting on past aspirations. He emphasizes the need to adjust goals as one grows and changes. Al also shares advice for his younger self, encouraging patience and a focus on personal fulfillment. He highlights the value of learning from failures and frustrations. Additionally, Al discusses finding joy in the journey and the importance of enjoying the process. He shares his reading preferences and talks about his exciting projects for the year, including involvement in local politics and exploring various hobbies and trades. You can watch/listen to the podcast on YouTube, Spotify, and Apple.Chapters00:48 Starting the Missouri Star Quilt Company02:16 Transitioning out of the Quilt Company03:13 Starting Let's Make Art04:33 Venturing into Tech Startups05:01 Investing and Real Estate09:24 Revitalizing Small Towns10:35 Balancing Work and Family12:14 The Therapeutic Catharsis17:52 Stepping Back from the CEO Role20:14 Finding a New CEO22:44 The Challenges of Being a Founder23:10 The Happiness of Founders25:30 The Cost of Being a Founder28:19 The Addiction to Validation29:17 The Illusion of the Finish Line30:58 The Ego-Driven Nature of Founders32:06 The Loneliness of Founders33:27 The Difficulty of Letting Go33:45 Setting Unrealistic Goals36:06 Reflecting on Past Goals36:18 Advice for Younger Self39:30 Lessons Learned: Patience and Timing41:37 Finding Joy in the Journey44:36 Reading Preferences45:30 Exciting Projects for the Year45:53 Interest in Local Politics46:47 Exploring Lost Trades and Hobbies
John Lott of Predicate Wealth Partners on Tough Board Meetings, Restructurings, and Mentorship
Mar 5 2024
John Lott of Predicate Wealth Partners on Tough Board Meetings, Restructurings, and Mentorship
On this episode with host David Paul, John Lott, CEO of Predicate Wealth Managers, shares his insights and experiences in the world of finance and entrepreneurship. He emphasizes the importance of operating skills and the potential of digital currencies. John also discusses the challenges in the private equity market and the significance of alignment between investors and founders. He shares his personal journey of transitioning to entrepreneurship and building a successful business with his wife. John's passion lies in helping others find their purpose and achieve success, which led him to develop the 8-Block Method. Overall, this conversation provides valuable lessons and perspectives for both investors and entrepreneurs. In this conversation, the principal themes revolve around finding passion, sustaining motivation, and the resilience of entrepreneurs. The guests emphasized the importance of pursuing something one is truly passionate about, as it provides the necessary drive to overcome challenges. They discuss the idea that everyone has a plan until they face adversity, highlighting the need for resilience in entrepreneurship. The conversation concludes with closing remarks and a call to action for listeners to subscribe, share, and leave reviews. You can watch/listen to the podcast on YouTube, Spotify, and Apple.TakeawaysOperating skills are crucial for success in business, and they are often more valuable than finance skills.The private equity market is not always efficient, and success depends on the alignment between sponsors and management teams.Effective communication and collaboration are essential for building successful partnerships between investors and founders.Working with a spouse as a business partner can be challenging but can also lead to personal and professional growth.The 8-Block Method is a framework for finding purpose and achieving success in life and business.Chapters00:00 Introduction and Background02:09 The Importance of Operating Skills03:25 The Potential of Digital Currencies05:25 Challenges in the Private Equity Market07:41 The Importance of Alignment Between Investors and Founders09:07 Effective Communication and Collaboration11:04 Transitioning to Entrepreneurship14:28 Lessons from Building a Successful Business17:55 Working with a Spouse as a Business Partner23:19 Starting Predicate Wealth Managers25:37 The 8-Block Method and Building a Legacy40:47 How to Learn More about the 8-Block Method43:31 Finding Passion and Sustaining Motivation44:01 The Resilience of Entrepreneurs
Maya Watson of Manual on the Failure of Learning and Development Industry and Lessons from Working for Oprah
Feb 20 2024
Maya Watson of Manual on the Failure of Learning and Development Industry and Lessons from Working for Oprah
Maya Watson, co-founder of Manual, discusses her background working for companies like Netflix and Oprah Winfrey, as well as her experience during the rise and fall of Clubhouse. She explains the genesis of Manual and its mission to help individuals understand themselves better and create a more flexible and fulfilling work experience. Maya highlights the challenges with traditional learning and development (L&D) programs and the need for a more personalized and contextual approach. She shares the company's plans for the future and how leaders can implement Manual in their organizations. Maya also reflects on her time working for Oprah Winfrey and the lessons she learned from the media mogul. You can watch/listen to the podcast on YouTube, Spotify, and Apple.TakeawaysManual is a platform that helps individuals understand themselves better and create a more flexible and fulfilling work experience.Traditional learning and development (L&D) programs often lack context and fail to address the individual needs of employees.The future of work is shifting, and tools like Manual can help individuals navigate this transition and find meaningful work.Leaders can implement Manual by leading by example, creating their own manuals, and encouraging their teams to do the same.Chapters01:08 - The Rise and Fall of Clubhouse03:00 - The Intersection of Factors06:14 - Introduction to Manual07:32 - The Genesis of Manual10:22 - The Problem with L&D14:09 - The Product and Company Today24:09 - Future Plans for Manual30:01 - Implementing Manual in the Workplace33:43 - Working for Oprah Winfrey
Brian Miller of Bloom Venture Partners on the Private Secondary Market and how to Unlock Liquidity for Employees and Early Investors
Feb 13 2024
Brian Miller of Bloom Venture Partners on the Private Secondary Market and how to Unlock Liquidity for Employees and Early Investors
Brian Miller, Partner at Bloom Venture Partners, discusses the secondary market for private company shares and the challenges and opportunities it presents. He explains the difference between primary and secondary markets and how secondary transactions work. Brian also discusses the controversy surrounding Carta and the importance of secondaries for both employees and investors. He highlights the restrictions on selling equity and the treatment of early-stage investors. Brian shares his optimism for the future of the market and emphasizes the importance of trust and differentiation in the industry. You can watch/listen to the podcast on YouTube, Spotify, and Apple.TakeawaysThe secondary market involves the transaction of shares that have already been issued by a private company.Companies and investors use the secondary market to provide liquidity to shareholders who want to sell their shares.The Carta controversy highlighted the misuse of customer information and led to the shutdown of their secondary business.Companies have different views on secondaries, with some seeing it as a positive benefit for employees and others concerned about control and optics.The majority of secondary transactions occur in later-stage companies that no longer need to raise capital.Chapters06:02 - Primary and Secondary Markets07:30 - How Secondary Transactions Work11:33 - The Carta Controversy14:09 - Importance of Secondaries for Employees and Investors18:46 - Restrictions on Selling Equity20:03 - Treatment of Early-Stage Investors23:34 - Current State of the Market25:52 - Majority of Transactions in Later Stage Companies26:27 - Challenges in the Secondary Market28:03 - Differentiation and Trust in the Industry29:12 - Personal Excitement and Future Outlook
Rahul Sidhu of Aerodome on Drones, American Dynamism, and Raising from a16z
Feb 6 2024
Rahul Sidhu of Aerodome on Drones, American Dynamism, and Raising from a16z
In this episode, host David Paul interviews Rahul Sidhu, the founder and CEO of Aerodome, a drone company for the public safety sector. They discuss the concept of Aerodome and its ability to send drones to 911 calls in an average of 98 seconds. They also delve into the regulatory challenges and waivers required for operating drones in the public safety space. Rahul shares his experience raising funding, including a seed round with 2048 Ventures and Andreessen Horowitz. They explore the intersection of American dynamism and lagging industries, as well as the importance of hardware sourcing in the United States. Rahul also discusses the progress of Aerodome and his excitement for the future of AI and robotics. The conversation concludes with a discussion on the impact of the 2024 election. You can watch/listen to the podcast on YouTube, Spotify, and Apple.TakeawaysAerodome is a drone company that sends drones to 911 calls in an average of 98 seconds, providing air support for public safety personnel.Regulatory challenges and waivers are necessary for operating drones in the public safety sector, and there is a need for innovation in this space.Raising funding for a startup like Aerodome can involve securing investments from venture capital firms like 2048 Ventures and Andreessen Horowitz.The intersection of American dynamism and lagging industries presents opportunities for innovation and growth.Hardware sourcing and supply chain regulation are important considerations for companies like Aerodome.Exciting developments in technology include advancements in AI, robotics, and the integration of AI into everyday life.The 2024 election is expected to have a significant impact on various industries and the country as a whole.Chapters03:00 - The Concept of Aerodome08:00 - Regulatory Challenges and Waivers11:00 - Raising Funding and Investors17:00 - The Intersection of American Dynamism and Lagging Industries23:00 - Supply Chain Regulation and Hardware Sourcing28:00 - Company Progress and Future Plans30:00 - Exciting Developments in Technology31:00 - The Impact of the 2024 Election
Matthew Pittinsky of Parchment and Blackboard on Revolutionizing Educational Technology and Building Networks
Jan 30 2024
Matthew Pittinsky of Parchment and Blackboard on Revolutionizing Educational Technology and Building Networks
In this episode, David Paul interviews Matthew Pittinsky, the founder of Blackboard and CEO of Parchment, about his journey in the educational technology industry. They discuss the genesis of Blackboard and its role in revolutionizing the learning management system (LMS) industry. They also explore the shift from on-premises software to cloud-based solutions and the challenges faced in building a networked system of record. Pittinsky shares his insights on the current pain points in education and the value of a college degree. The conversation concludes with a discussion of favorite books and closing remarks.TakeawaysBlackboard revolutionized the LMS industry by creating a front office system for universities that facilitated instruction and learning.The shift to cloud-based solutions, exemplified by Instructure's Canvas LMS, disrupted Blackboard's on-premises model.Parchment was founded to address the need for a networked system of record that allows learners to collect and manage their academic and professional credentials.The education industry faces challenges such as fragmented technology ecosystems, math achievement gaps, teacher retention, and the perception of the value of a college degree.Chapters03:14 The Genesis of Blackboard08:00 The Shift to the Cloud12:05 The Birth of Parchment15:29 Building a Networked System of Record20:17 Adoption Challenges and Cultural Battles21:47 The Vision of Parchment23:34 Current Pain Points in Education26:18 Is College Worth It?29:55 Favorite Books
Scott Garber of Early Light Ventures on Founder Interviewing via CIA techniques, Pre Seed Portfolio Construction, and Farting in Jars
Jan 23 2024
Scott Garber of Early Light Ventures on Founder Interviewing via CIA techniques, Pre Seed Portfolio Construction, and Farting in Jars
In this episode, David Paul interviews Scott Garber, Managing Director of Early Light Ventures. Scott shares his background as a former CIA operative and how he transitioned into venture capital. He discusses his investment strategy, including the importance of reading founders and identifying grit. Scott also talks about the portfolio construction and his focus on smaller exits with lower failure rates. He reflects on his beliefs that have changed over time and shares his excitement for the future. You can watch/listen to the podcast on YouTube, Spotify, and Apple.TakeawaysScott shares his background as a former CIA operative and how it has influenced his venture capital career.Reading founders and identifying grit are important factors in Scott's investment strategy.Scott focuses on smaller exits with lower failure rates in his portfolio construction.Scott's beliefs about valuations have evolved, and he now considers quality as an important factor in investment decisions.Scott is excited about the sales prospects for startups in the first half of 2024.Chapters03:57 - Transition to Venture Capital05:30 - Recruitment into the CIA07:19 - Transferable Skills from CIA to Venture Capital09:48 - Investment Strategy and Reading Founders13:16 - Early Light Ventures and Investment Thesis15:29 - Transition from Board Seats17:52 - Portfolio Construction and Miss Rates20:49 - Beliefs that Have Changed24:24 - Excitement for 202427:17 - Conclusion and Contact Information
Luke Harmon of Serendipity on When Bootstrapping Backfires, Identifying Blue Ocean, and how to Increase your Company's Valuation
Jan 16 2024
Luke Harmon of Serendipity on When Bootstrapping Backfires, Identifying Blue Ocean, and how to Increase your Company's Valuation
Luke Harmon, founder and CEO of the Serendipity marketing agency, shares his startup journey and the challenges of bootstrapping a company. He discusses the importance of balancing sales and product development, as well as the need for founders to be involved in the sales process. Luke also highlights the significance of building strong relationships with clients and the value of nurturing prospects. Overall, he emphasizes the importance of revenue generation and the need for founders to understand the market dynamics and make strategic decisions. In this conversation, Luke Harmon discusses the HubSpot focus and alignment, the future of go-to-market strategies, the flipped funnel approach, and partnerships as a growth strategy. He also emphasizes the importance of considering the impact of partnerships and provides his contact information for further communication. You can watch/listen to the podcast on YouTube, Spotify, and Apple.TakeawaysBootstrapping a company requires careful financial management and a focus on revenue generation.Founders should be actively involved in the sales process and develop sales skills.Building strong relationships with clients and nurturing prospects is crucial for long-term success.Balancing product development and customer needs is a challenge that requires constant iteration and adaptation. HubSpot's focus and alignment have been instrumental in their success.The traditional funnel approach is being replaced by the flipped funnel approach in B2B SaaS.Targeted content creation and brand personality are key in the flipped funnel approach.Partnerships can be a game-changer for businesses, but careful consideration is needed.Chapters01:19 Definition of Bootstrapping03:33 Luke's Startup Journey06:18 Early Days of Employee Engagement Giving09:25 Product Development and Growth Challenges11:14 Acquisition by BlackBod15:54 Life After the Exit24:06 Serendipity Marketing Agency28:59 Balancing Sales and Product Development33:44 Qualification and Sales Coaching37:23 Building Deal Stages and Nurturing Prospects38:40 Future Outlook and Excitement38:45 HubSpot Focus and Alignment40:26 The Future of Go-to-Market Strategies42:47 The Flipped Funnel Approach43:22 Partnerships as a Growth Strategy44:21 Considering the Impact of Partnerships
Angela Lai former Founder of Betteromics (former CTO of GRAIL) on Building Software for the Life Science Industry and What The World Doesn't know About Big Pharma
Jan 8 2024
Angela Lai former Founder of Betteromics (former CTO of GRAIL) on Building Software for the Life Science Industry and What The World Doesn't know About Big Pharma
In this episode, David Paul interviews Angela Lai, the founder and CEO of Betteromics. They discuss Angela's background in the tech industry and her transition to the life sciences business. They explore the intersection of biology, chemistry, big data, and AI in the field of healthcare science. Angela explains how Betteromics serves as a regulated data lake for healthcare science data, providing a system of record and interoperability for clinical discovery. They also discuss the challenges and opportunities in the life science industry, the future of pharma and personalized medicine, and the importance of transparency and storytelling in the industry. Angela shares her insights as a founder and the personal growth she has experienced in building a startup. You can watch/listen to the podcast on YouTube, Spotify, and Apple.TakeawaysThe life science industry is undergoing a transformation as biology, chemistry, big data, and AI converge.Betteromics serves as a regulated data lake for healthcare science data, providing a system of record and interoperability for clinical discovery.The life science industry faces challenges in data fragmentation, data governance, and the need for more efficient and predictable drug development.Specialty pharma medicines, personalized medicine, and biologics are the future of the industry.Founding a startup requires versatility, problem-solving skills, and a willingness to learn and adapt.Chapters02:08 Transition from Google to Grail to Betteromics03:32 The Intersection of Biology, Chemistry, Big Data, and AI06:06 Betteromics as a Regulated Data Lake for Healthcare Science09:08 Challenges in the Life Science Industry12:18 Positioning Betteromics in the Market16:23 The Future of Pharma and Life Science19:40 Technological Advances Enabling Betteromics22:52 The Success Rate of Drugs and Therapies28:14 The Opacity of the Life Science Industry31:17 The Rise of Specialty Pharma Medicines34:30 Lessons Learned as a Founder37:49 Personal Growth and Privilege
Matt Munson of Sanity Labs on Founder Burn Out, Executive Coaching, and Board Dynamics
Dec 26 2023
Matt Munson of Sanity Labs on Founder Burn Out, Executive Coaching, and Board Dynamics
In this episode, David Paul interviews Matt Munson, a CEO whisperer and performance coach for startup founders at Sanity Labs. Matt shares his experience working with Jerry Colonna, a renowned coach, and the impact it had on his own coaching approach. They discuss the importance of recognizing inner complacency and the deeper challenges faced by entrepreneurs. Matt also explores the concept of founder burnout and the need for a shift in mindset to prioritize well-being. They delve into the role of attachment to identity and business success, as well as strategies for maximizing creativity and vision. The episode concludes with advice for investors on supporting founders in a more communicative and supportive manner. You can watch/listen to the podcast on YouTube, Spotify, and Apple.TakeawaysCoaching should involve more than just providing frameworks and advice; it should involve a deep understanding of the founder's challenges and a willingness to climb into those challenges with them.Founder burnout often stems from a feeling of misalignment, disconnection, and inefficacy. It is important to address these deeper issues rather than just focusing on external factors.Attachment to identity and business success can hinder a founder's ability to lead effectively. It is important to shift the focus from personal validation to the collective vision and purpose of the company.Slowing down and creating space for innovation is crucial for founders. Prioritizing activities that foster spacious thinking, long-term visioning, and deep connection with the team can lead to more effective leadership.Investors should approach founders with curiosity and support rather than solely focusing on performance metrics. Creating an open and supportive environment can lead to better outcomes for both the founder and the investor.Chapters01:00 Working with Jerry Colonna03:02 Jerry Colonna's Questions04:36 Searching for Coaching07:48 Recognizing Inner Complacency08:58 Founder Burnout11:20 Attachment to Identity and Business14:39 Finding Clarity and Vision20:45 Maximizing Creativity26:05 Slowing Down for Innovation29:29 Supporting Founders as an Investor