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  • 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

  • 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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  • 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'

  • 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

  • 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

  • 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
  • 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?"
  • 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...

  • 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.

    Takeaways

    Customer 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.

    Chapters

    00:00 Introduction and Background

    02:26 The Importance of Customer Empathy

    08:21 Challenges in Commercializing Healthcare Products

    14:51 Shifting the Market Conversation

    Keywords- healthcare, startups, customer empathy, product-market fit, commercialization, market validation, founder bias

    29:12 The Role of Market Validation

  • 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.

    Takeaways

    The 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.

    Chapters

    01:05 The Need for Infrastructure Investment

    03:09 The Importance of Infrastructure to Joe Biden

    04:15 Improving Infrastructure in New York City

    05:19 Bidding and Contracting in the Construction Industry

    06:13 Different Types of Construction and Contractors

    07:38 The Role of General Contractors and Subcontractors

    08:33 The Transition to Design-Build Contracts

    09:20 Low Margins in the Construction Industry

    10:17 Increasing Margins with Construction Technology

    11:46 The Challenges of Construction Technology Adoption

    13:02 Using Technology to Track Labor and Materials

    14:53 Addressing Pain Points in Construction

    16:15 The Importance of Integration and Connectivity

    19:12 Regulatory Changes and Pain Points in Construction

    20:40 Using Digital Twins for Infrastructure Assessment

    23:16 The Need for Standardization in Construction

    27:17 The Opportunity in Infrastructure Repair

    29:38 Contacting Lisa Diaz and Turf Advisory

  • 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.

    Takeaways

    Building 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.

    Chapters

    02:10 The Importance of Team and Leadership

    05:27 Driving Innovation in a Large Company

    07:04 Structuring and Leading Complex Projects

    10:03 Navigating Change Management and Reputational Risk

    13:29 Effective Hiring and Onboarding

    25:03 Conducting Effective Interviews

    26:00 Areas of Concern and Excitement in Technology

    27:19 Benefits of Modern Tools in Coding Productivity

    29:15 Team Building in the Post-COVID Era

    30:27 Understanding the Data Stack

    34:21 Platforms vs. Best-in-Class Solutions

    38:32 The Importance of Making Choices in Strategy

    40:28 Learning from Leaders and Building Bridges

  • 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.

    Takeaways

    Building 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.

    Chapters

    02:23 Background and Experience

    03:24 Foray into Investing and Role at Sopras Capital

    04:37 Relationship with Sopras Capital

    05:30 Investment Advice from Andy

    06:41 Navigating Challenges in Early Stage Investing

    07:14 Managing Anxiety and Frustration

    09:21 Founder Buy-In on Operational Expertise

    09:38 Differentiation in Capital Allocation Strategy

    14:34 Flexibility in Entry and Exit Strategies

    15:48 Challenges of Overcapitalization

    19:22 Tech-Enabled Services vs. SaaS

    22:52 Decentralization of Healthcare

    26:11 Shift in Healthcare Awareness and Ownership

    28:26 Demand for Additional Healthcare Tests

    30:10 Advanced Practice Providers in Healthcare

    32:23 Favorite Investors and Reading Recommendations

  • 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.

    Takeaways

    Personal 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.

    Chapters

    03:20 Rebooting and Radical Self-Inquiry

    08:57 Reunion and Personal Growth

    16:05 The Importance of Painful Work

    25:15 The Role of Investors in Founder Dishonesty

    27:48 The Systemic Issues in Startup Culture

    29:09 The State of Investing

    30:06 The Importance of Relationships

    31:15 The Genesis of Reunion

    33:03 A Pointing Out Instruction

    34:29 Systematic Racism and Oppression

    36:00 Fear of the Other

    37:00 Radical Self-Inquiry and Leadership

    39:08 Attacking Ideologies and the Real Problems

    40:30 The Moral Responsibility of Business Leaders

    42:22 The Next Iteration of Jerry's Work

  • 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.

    Chapters

    00:48 Starting the Missouri Star Quilt Company

    02:16 Transitioning out of the Quilt Company

    03:13 Starting Let's Make Art

    04:33 Venturing into Tech Startups

    05:01 Investing and Real Estate

    09:24 Revitalizing Small Towns

    10:35 Balancing Work and Family

    12:14 The Therapeutic Catharsis

    17:52 Stepping Back from the CEO Role

    20:14 Finding a New CEO

    22:44 The Challenges of Being a Founder

    23:10 The Happiness of Founders

    25:30 The Cost of Being a Founder

    28:19 The Addiction to Validation

    29:17 The Illusion of the Finish Line

    30:58 The Ego-Driven Nature of Founders

    32:06 The Loneliness of Founders

    33:27 The Difficulty of Letting Go

    33:45 Setting Unrealistic Goals

    36:06 Reflecting on Past Goals

    36:18 Advice for Younger Self

    39:30 Lessons Learned: Patience and Timing

    41:37 Finding Joy in the Journey

    44:36 Reading Preferences

    45:30 Exciting Projects for the Year

    45:53 Interest in Local Politics

    46:47 Exploring Lost Trades and Hobbies

  • 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.

    Takeaways

    Operating 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.

    Chapters

    00:00 Introduction and Background

    02:09 The Importance of Operating Skills

    03:25 The Potential of Digital Currencies

    05:25 Challenges in the Private Equity Market

    07:41 The Importance of Alignment Between Investors and Founders

    09:07 Effective Communication and Collaboration

    11:04 Transitioning to Entrepreneurship

    14:28 Lessons from Building a Successful Business

    17:55 Working with a Spouse as a Business Partner

    23:19 Starting Predicate Wealth Managers

    25:37 The 8-Block Method and Building a Legacy

    40:47 How to Learn More about the 8-Block Method

    43:31 Finding Passion and Sustaining Motivation

    44:01 The Resilience of Entrepreneurs

  • 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.

    Takeaways

    Manual 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.

    Chapters

    01:08 - The Rise and Fall of Clubhouse

    03:00 - The Intersection of Factors

    06:14 - Introduction to Manual

    07:32 - The Genesis of Manual

    10:22 - The Problem with L&D

    14:09 - The Product and Company Today

    24:09 - Future Plans for Manual

    30:01 - Implementing Manual in the Workplace

    33:43 - Working for Oprah Winfrey

  • 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.

    Takeaways

    The 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.

    Chapters

    06:02 - Primary and Secondary Markets

    07:30 - How Secondary Transactions Work

    11:33 - The Carta Controversy

    14:09 - Importance of Secondaries for Employees and Investors

    18:46 - Restrictions on Selling Equity

    20:03 - Treatment of Early-Stage Investors

    23:34 - Current State of the Market

    25:52 - Majority of Transactions in Later Stage Companies

    26:27 - Challenges in the Secondary Market

    28:03 - Differentiation and Trust in the Industry

    29:12 - Personal Excitement and Future Outlook

  • 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.

    Takeaways

    Aerodome 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.

    Chapters

    03:00 - The Concept of Aerodome

    08:00 - Regulatory Challenges and Waivers

    11:00 - Raising Funding and Investors

    17:00 - The Intersection of American Dynamism and Lagging Industries

    23:00 - Supply Chain Regulation and Hardware Sourcing

    28:00 - Company Progress and Future Plans

    30:00 - Exciting Developments in Technology

    31:00 - The Impact of the 2024 Election

  • 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.

    Takeaways

    Blackboard 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.

    Chapters

    03:14 The Genesis of Blackboard

    08:00 The Shift to the Cloud

    12:05 The Birth of Parchment

    15:29 Building a Networked System of Record

    20:17 Adoption Challenges and Cultural Battles

    21:47 The Vision of Parchment

    23:34 Current Pain Points in Education

    26:18 Is College Worth It?

    29:55 Favorite Books

  • 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.

    Takeaways

    Scott 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.

    Chapters

    03:57 - Transition to Venture Capital

    05:30 - Recruitment into the CIA

    07:19 - Transferable Skills from CIA to Venture Capital

    09:48 - Investment Strategy and Reading Founders

    13:16 - Early Light Ventures and Investment Thesis

    15:29 - Transition from Board Seats

    17:52 - Portfolio Construction and Miss Rates

    20:49 - Beliefs that Have Changed

    24:24 - Excitement for 2024

    27:17 - Conclusion and Contact Information