The Capital Stack
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.
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...
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...
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...
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...
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...
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...
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...
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...
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.
Takeaways
Cu...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...
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...
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...
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...
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...
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...
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...
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.
...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...
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.
Takeaways
Blackboard revolutionized...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.
Takeaways
Scott shares his background as a...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...
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...
Bill Horne Turnaround CEO of over 10+ Companies on Why Founders Fail and What to Do About It

In this episode, venture capitalist David Paul interviews Bill Horne, a 10-time CEO, the founder of 88 Keys, and an expert in turning around struggling companies. They discuss various aspects of being a fixer for early-stage companies and the challenges that come with it. The conversation covers topics such as the value destruction when founders leave, common mistakes founders make, the importance of operational planning, and managing the board. You can watch/listen to the podcast on YouTube, Spotify, and Apple.
Takeaways
Being a fixer for early-stage companies requires reconciling the challenges of working with fragile employees an...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...
Gregg Scoresby of PHX Ventures on Mastering the Art of Startup Board Management and Building Vibrant Software Communities

In this episode, David Paul interviews Gregg Scoresby, the founder and CEO of CampusLogic and PHX Ventures about building a thriving startup ecosystem in Arizona. They discuss the challenges and opportunities of attracting institutional seed stage capital, the importance of community vibrancy in building a top software city, and the role of AI in the future of software companies. Greg shares his insights on identifying founders with ambition and the ability to confront reality and emphasizes the need for founders to be connected to the math of their business. He also provides advice for founders and investors on building...
Alan Roga of TruLight Health on Health Equity, Clinical Bias, and Creating Healthcare Categories

David Paul, venture capitalist and host of The Capital Stack Podcast is joined by Alan Roga, seasoned medical professional turned entrepreneur and founder of TruLite Health. Telehealth and telemedicine seem commonplace today, although it was not always that way. Listen to the interesting story of how it developed into what it is today and Alan’s view on the current industry. Alan provides deep insight into how the development of telehealth led to the development and sparking of health equity, providing care to individuals from all walks of life. You can watch/listen to the podcast on YouTube, Spotify, and...
Jim Cantrell of Phantom Space on the Space Tech, the Defense Sector, and Advanced Manufacturing Supply Chain

On this episode of The Capital Stack Podcast, venture capitalist David Paul is joined by lifelong space executive and CEO of Phantom Space, Jim Cantrell, to talk about the inner workings of the innovation happening in space exploration. Jim and David discuss the history of the space industry, why startups are outperforming primes and projections for the future of aerospace and defense supply chain. Follow along on this incredible episode where the inner workings of all innovation that goes into rockets and satellites are unraveled and explained in extraordinary detail. You can watch/listen to the podcast on YouTube, S...
Austin Poole of BIP Ventures on Inflation, Incentives, and Dysfunction in Healthcare Services

David Paul, venture capitalist and host of The Capital Stack Podcast is joined by Austin Poole - a partner at BIP Ventures focusing on healthcare. BIP Ventures is an Atlanta-based venture firm with various focuses, with hundreds of millions of dollars under management in credit and equity. David and Austin discuss the current state of the healthcare market, post-acute care in the market, and the software and technology that go into and scale healthcare. Listen to Austin’s unexpected path to BIP Ventures, how he chooses investments with his team, and what he sees for the future of healthcare te...
Jim Armstrong of JDA Software on Founding a $2B Company, Operating and Investing Lessons, and Finding Meaning in Wealth

On this episode of The Capital Stack Podcast, venture capitalist David Paul speaks with his mentor, Jim Armstrong, founder of JDA Software (now Blue Yonder) - a global supply chain solution for big box retailers. This inspiring episode is filled with invaluable information and highlights how opportunity is everywhere, and when acted upon with the right mindset, success can flourish. Listen to Jim speak about his irregular journey to success, what lessons he would tell his younger self, and how Jim chooses to spend his time today. You can watch/listen to the podcast on YouTube, Spotify, or Apple.
...Mike Becker of Vocapp Partners on Verticalized Generative AI Applications, East vs. West Coast Investing, Identifying Stages of Product Market Fit

David Paul is joined by fellow venture capitalist Mike Becker, the managing partner of Vocap Partners, a Series-A firm based out of Atlanta and Florida, on this episode of The Capital Stack Podcast. David and Mike discuss how to pick and choose ideal companies for deals, the importance of VC / founder balance in value add, and what is new and exciting in venture capital today!
What You Will Discover -
(5:00) - Mike’s view on value creation as a venture capitalist
(9:10) - The story of Vocap and Mike’s experience as a venture capi...
Todd Belfer of Brookstone VC on Raising Capital from LPs and Key Investing Lessons

On this episode of The Capital Stack Podcast, venture capitalist David Paul speaks with his mentor, Todd P. Belfer of Brookstone Venture Capital - an Arizona-based venture capital firm. Todd speaks about his irregular and inspiring path to success, the importance of consistency and discipline, and his learnings as an investor and operator. David and Todd discuss their wins and losses from working together, and their valuable insight on the startup market today. You can watch and listen to the podcast on on YouTube, Spotify, and Apple.
What You Will Discover -
(2:38...
Hamid Shojaee of Savvy Trader on Investor Bias, Regulating Emotions, and Emerging Trends

This week I had the opportunity to invest with friend and serial entrepreneur Hamid Shojaee. Hamid has been the founder of several companies and products including Axosoft, NetTime Solutions, and Get Krackin. You can watch/listen to the podcast on YouTube, Spotify, and Apple.
On this episode of the Capital Stack Podcast hosted by venture capitalist David Paul - Hamid Shoajee, serial entrepreneur, author, investor, and founder of Savvy Trader, an Arizona-based investment portfolio-sharing software company, gets on the microphone. David and Hamid engage in conversation about how to get started in investing, how to balance and main...
Will Shaw of Better Agency on SMB Customer Churn, the Insurance Market, and a Winning Morning Routine

On this episode of the Capital Stack Podcast hosted by venture capitalist David Paul - Will Shaw, the pro-football player turned tech founder of Better Agency, an Arizona-based insurance management software company, gets on the microphone. David and Will discuss the current state of the startup market, the solution to high churn, why insurance rates are so high, and the back end of the insurance space. Will opens up about what habits he practices to stay successful, the importance of showing up, and what is most shocking about becoming a founder. Listen to this episode on all your platforms...
David Freedman of Freestar on the State of AdTech Today, Privacy, and Democratizing The Auction Process

Despite his reluctance, I got David to speak to me about the overly complex ecosystem of the adtech business today. David is an incredible entrepreneur who has helped disable the giants that have monopolized the digital ad business for decades. Hint- it rhymes with Schmoogle.
Have you ever wondered about the backend workings of website monetization and ad-tech? The ad-tech industry is a fast-moving industry that’s allowing publishers around the world to invest in their work and have world-class technology dealing with the inefficiencies in the industry.
In this episode of The Capital Stack, we have...
Will Caldwell of SnapNHD on Real Estate Tech, Bootstrapping, and Big Data

It is a great pleasure to introduce our next podcast guest - Will Caldwell founder and CEO of SnapNHD - a San Diego based real-estate data company. I had the chance to invest in Wills company very early and if I did it would of resulted in a 10x outcome. Oops. At least I can laugh at it and Will and friend. You can listen to the podcast on all your platforms including YouTube, Spotify, or Apple.
Does your startup have what it takes to identify strong business cases, have ready-to-go customers on the products, and have...
Liz Harrow of SHAKTI on Disrupting Commerce, Mobility, and Media Industries and Creating Value Through LP Engagement

I had the privilege of meeting Liz recently, thanks to a referral from one of the CEOs of their portfolio companies. It's worth noting that Liz is not one for outward marketing. Nonetheless, her unique perspective on the world is awe-inspiring, and I'm excited to share her story and the incredible journey of SHAKTI with you.
How does a small team and emerging venture capital fund prioritize supporting and empowering founders? Taking the community approach is a great way to add value to early-stage founders by bringing in mentors and industry titans.
In this episode...
Jessica Chang of Upwards (formerly WeeCare) on Solving the Labor Shortage through Democratizing Child Care

When searching for determined founders, it's crucial to recognize individuals with a chip on their shoulders. Jessica Chang undoubtedly possesses this quality. She's fed up with witnessing mothers, who are deprived of opportunities, forced out of the workforce due to exorbitant childcare expenses. Discover how Jessica and the Upwards team are revolutionizing traditional childcare, catering to those who need it most and breaking the cycle of inequality. You can watch/listen to this podcast on YouTube, Apple, or Spotify.
Are you aware of the struggle parents and childcare providers are going through? How do we make care...
Mat Elis of SixtyAI formerly of Cloudability on Generative AI and Building Viral Products

I recently had the pleasure of meeting Mat, and I must say, he is absolutely delightful, despite his charming accent. As is often the case with founders, he found it challenging to remain idle after the successful sale of Cloudability for a staggering $1.8B, backed by Founders Fund and Foundry.
What if you had a robot chief of staff to help you remember other people’s problems? Think of a human-compatible AI product built and designed to enhance your productivity which will, in turn, make you a better executive.
In this episode of The Capital St...
Jen Abel on Why Founders Fails to Find Product Market Fit

Jen is perhaps one of my favorite follows on twitter on Linkedin. She is relentlessly honest about why startup founders fail to find product market fit and self-destruct. This is a must listen for any early stage founder. You can watch/listen to the podcast on YouTube, Apple, or Spotify.
Do you know it’s almost impossible for a startup to succeed without the founder at the tip of the spear? For an early-stage startup to move from 0-1 and avoid premature scaling, it needs to be led by a visionary. Leading a startup as the founder is a com...
Anthony Enrico of LeanScale on Building RevOps Function within your Company and Steps going from Founder-Led-Sales to a Repeatable Sales System

Going from founder-led-sales to a sales team is a bi#Tch. One of the first things a founder needs to think about is how to connect data and systems together to effectively understand what is working and what's not. Join me in discussing revenue operations with the grand master himself - Anthony Enrico- of LeanScale. You can watch/listen to this podcast on YouTube, Apple, or Spotify.
How do you handle revenue operations in your business, and when did you start doing it? Revenue ops is a better management system for aligning go-to-market operations to boost revenue gro...