What does building an attractive SaaS product and client trust take? Building an all-in-one platform in the vertical SaaS industry as a startup can be challenging and requires crossing the chasm and proving value to the target market to break even.In this episode of The Capital Stack, we have Sebastian Gabor, the Co-founder & CEO of Digitail. Digitail’s mission is to give veterinarians the ability to provide smarter, more effective, and personalized pet treatment. Listen in to learn the importance of understanding the key problem you’re solving and focusing on it when building a SaaS company. You will also learn what it takes to build a successful veterinary vertical SaaS, plus the future of the veterinary market.What You Will Discover:·       [02:15] How Sebastian’s frustrating firsthand experience with vet services led him to start Digitail.·       [05:35] How Digitail had to cross the chasm and prove its value to the target market to gain trust.·       [08:10] The importance of understanding the key problem you’re solving and focusing on it when building a SaaS company. ·       [10:11] The big lessons he learned building a veterinary vertical SaaS while meeting client needs.·       [13:10] He explains their simplified pricing and revenue strategy, plus their focus on working with aggregators. ·       [16:47] The challenges aggregators are having and the two sides of pricing in the veterinary market.·       [19:58] How the pet demand is predicted to affect the veterinary market in the future.·       [23:40] Sebastian on the investing power of AI in the veterinary market and how they’re doing it.·       [25:50] Random questions with Sebastian!Memorable Quote:·       “Instead of doing twenty things, focus on doing one thing really well and then move to the next.”- Sebastian [25:50]Connect with Sebastian:·       LinkedIn: https://www.linkedin.com/in/sebastiangabor/

How do you bring new principles into an old industry like dictation? In recent years, tech tools such as generative AI and software have changed the digital transcription and scribing industry to be more exciting for customers, developers, and investors.  In this episode of The Capital Stack, we have Shawn Wilkie, a serial entrepreneur, technology enthusiast, and the Chief Executive Officer at Talkatoo. Talkatoo is a dictation software changing how veterinarians document their medical records by allowing them to dictate directly into their practice management software.Listen in to learn how to build an attractive solution and a successful business when you already know your product market fit. You will also learn about the existing opportunities in the vet industry and how providing efficiencies with AI and software tools can lessen human resource requirements.What You Will Discover:[02:05] Shawn shares his journey in the veterinary vertical and building software.[06:52] How he built an easy-to-use solution and grew the business while already knowing the product market fit.[08:18] How they’re executing Shawn’s vision of enabling people to have speech-enabled experience on any internet-connected device.[10:19] How they allow people to get through documentation quicker, plus their continued growth.[11:40] How AI is changing the world of dictation by producing better results than what was said.[18:31] Factors that have caused a high demand low supply crisis in the veterinary industry.[22:14] How Talkatoo sells efficiency through its dictation products to improve veterinary workflow.[24:34] Talkatoo’s focus on not raising capital and growing beyond the veterinary vertical.[26:07] The incredible opportunities for efficiency gain and capacity building in veterinary medicine.[28:53] Random questions with Shawn!Memorable Quote:“Every single position in a veterinary hospital has a labor shortage right now, so if we can find other areas of efficiency with software and AI, that’s where the opportunities are.”- Shawn [26:29]Connect with Shawn:Website: https://talkatoo.com/LinkedIn: https://www.linkedin.com/in/wilkieshawn/Books Mentioned: Think and Grow Rich and Atomic Habits 

This week I am talking to A++ operator Sergio Radovic, founder and CEO of Dyper - a $100M run-rate DTC CPG brand located in Scottsdale, Arizona. - Sergio shares his background as a technologist and his previous roles in various startups and technology companies. - Exploring Sergio's journey into the diaper business driven by his desire to address the environmental impact of traditional diapers. - Sergio discusses the hidden environmental consequences of traditional diapers, such as the use of plastic and their contribution to landfills. - The mission of Dyper is to create a responsible and sustainable diaper alternative using bamboo as a primary material. The bamboo plant's fast growth and minimal need for fertilizers make it an environmentally friendly choice. - Dyper's unique approach involves a cradle-to-compost solution, including a pickup service for used diapers in select cities. - Quantifying the impact of Dyper's products on carbon emissions and landfill waste. The challenges of being a challenger brand in the direct-to-consumer space, particularly in the highly regulated and competitive diaper market. - Dyper's strategy to capture emerging trends in sustainability and cater to customers willing to pay a premium for eco-friendly products. Balancing price considerations and margin protection while expanding into retail partnerships with giants like Walmart and Amazon. - The importance of brand messaging and adapting brand blades to different distribution channels. - Sergio shares the story of Dyper's beloved giraffe mascot, Frankie, and the unintentional brand recognition it has gained. - Exploring the transition from direct-to-consumer sales to retail and the challenges faced along the way. - The impact of COVID-19 on fundraising and adapting to virtual fundraising processes. - Navigating the changes in advertising channels and the effects of privacy issues with Apple and Facebook. - Leveraging first-party signals and targeted marketing to reach the right audience for Dyper's niche product. - The future possibilities and expansion of Dyper beyond the baby diaper market. - The speaker discusses the importance of data and data enhancement in their business. They mention that every record that comes to them goes through a data enhancement process to model customer behavior clusters. - Data enhancement helps them provide detailed information to retail partners about their customers, such as shopping preferences, media consumption, household income, and presence of children. - They give an example of targeting customers who buy fancier kids' clothes based on income propensity rather than broad market segmentation. The speaker compares selling to retailers to selling to investment partners, emphasizing the need to bring data and spin a compelling story. - They talk about the challenges of pitching to first-time venture capital funds and the importance of tailoring the story to align with their interests. - The speaker mentions finding an investor specialized in direct-to-consumer challenger brands, highlighting the investor's focus on being a permanent source of capital. - They explain that their company has only common shares, which was not an easy negotiation but aligns management and investor interests. The speaker discusses the focus on brand building and creating an enduring American brand. - They emphasize the need for a longer-term horizon and substantial capital investment in building a brand. The speaker mentions measuring brand perception and recognition as important metrics alongside sales. - They discuss the direct-to-consumer (D2C) model and its limitations, stating that it is not a sustainable standalone channel for most brands. - The speaker suggests treating D2C as a fast channel for customer feedback and market proof, but not as the sole strategy for reaching households. - They mention the importance of having an Amazon strategy and a retail strategy to reach larger scale and align with consumer preferences. - The speaker highlights the execution of Walmart and other retailers in adapting to the shift in consumer behavior, including same-day delivery and eco-friendly packaging. - They mention the significant number of brands launched by retailers like Target compared to CPG companies, highlighting the importance of strategy and understanding customers. - The speaker discusses the potential benefits of Walmart acquiring TikTok and leveraging its user-generated media platform.

In this episode of the Capital Stack podcast, host David Paul interviews Ross Fubini, the managing director of XYZ Ventures based in San Francisco. They discuss various topics related to venture funding, technology, and market trends. Here are the key highlights from the conversation: Ross Fubini's Background: Ross shares his background as a computer scientist and his early experience working for Netscape in the late '90s when the internet was still in its early stages of development. Netscape's Impact: They discuss Netscape's role in creating various foundational elements of the internet that are now taken for granted, such as the browser and proxy server, which laid the groundwork for the CDN (Content Delivery Network) business. Ross's Career Journey: Ross talks about his career path, including working for companies like Tellme, Plum Tree, Symantec, and starting his own enterprise software company, which was eventually acquired by SuccessFactors. He also mentions his transition into venture capital and his experiences at KPort Capital and Canaan Partners. Village Global: Ross briefly introduces Village Global, a network-based venture firm that connects luminaries, investors, fund managers, and founders. He highlights the power of networks and the opportunities they create. XYZ Ventures: Ross dives into XYZ Ventures, his current venture capital firm. They have a deep focus on founders coming from the Palantir network and have invested in companies within the enterprise software, FinTech, and SureTech sectors. Public Sector Opportunities: Ross explains their interest in the public sector, driven by his personal background and passion for making a significant impact in areas like defense, healthcare, and government procurement. He mentions their investment in Anduril, a defense contractor, as an example. Identifying Opportunities: Ross emphasizes the importance of identifying changing trends and industries where significant opportunities for innovation and growth exist, such as climate technology and procurement. Software Adoption in Traditional Industries: The hosts observe that traditionally stodgy industries like utilities and infrastructure are now buying software solutions, indicating a shift towards digital transformation and increased adoption of technology. Early Stage of Transformation: They acknowledge that despite the progress, these shifts are still in the early stages, and there are significant opportunities for innovation and growth in industries like defense and FinTech. Missed Opportunities in Healthcare: The hosts reflect on the missed opportunities in the healthcare sector, particularly during the COVID-19 pandemic, where the focus was primarily on telehealth and not enough on tech-enabled solutions and efficiency improvements. Complexity and Competition in Software: They discuss how software solutions that address complex problems tend to offer more value, as the easy problems have already been solved. Additionally, they note that the competitive landscape in the software industry can be intense, requiring constant innovation to stay ahead. Network-Driven Investments: The hosts emphasize the importance of networks and relationships in venture capital. They share their approach of focusing on founders introduced by other founders, as about 50% of their portfolio companies have come through such introductions. Outbound Sourcing: While they don't rely heavily on outbound sourcing, they believe in being proactive in reaching out to potential founders through their networks and leveraging existing relationships. Market Cycles and Portfolio Companies: The hosts mention that they are fortunate to be in a strong position with profitable late-stage investments and well-funded early-stage companies. They advise their portfolio companies to be appropriately skeptical, closely monitor budgets and sales performance, and continue demonstrating growth despite market challenges. Overall, the episode covers Ross Fubini's background in technology, his venture capital journey, the focus areas of XYZ Ventures, and their interest in venture funding within the public sector, including defense and American infrastructure.

Aaron Charlesworth is one of the best B2B Marketers I know- he has been a marketing and product executive for some incredible B2B companies including Vocalocity, Onsolve, Omnilink, and SpaceIQ. He has a wealth of knowledge about B2B marketing, strategy, and product management. It's no surprise that he is regularly sought out for expert advice on the topics from industry leaders. On this podcast we are going to talk about what early stage company founders get wrong with marketing and what is the correct way to start a marketing motion. We will also explore tactics and strategies that Aaron has used in his own businesses as well as how he spot trends and moves quickly to capitalize on them. Tune in to hear all of this great advice from one of the best B2B marketers out there! I'm sure it's going to be an amazing episode.

Have you thought of all the different revenue outcomes your company can have? With revenue-based funding, you don’t have to exit to make a meaningful return; you can share a percentage of your revenue over time.In this episode of The Capital Stack, we have Melissa Withers, co-founder and Managing Partner of RevUp Capital. Her interest lies in supporting founders building their businesses without the benefits of economic and social privilege. She talks about the type of revenue-based funding RevUp does to help underserved companies. Listen in to learn why some companies are underserved by traditional venture capital and how revenue-based funding gives these companies the opportunity to grow. You will also learn why aspiration, authenticity, and credibility are qualities of a great founder looking to overcome the early stage.What You Will Discover:·       [00:00] Intro·       [01:52] The type of revenue-based funding RevUp does – returning value to a revenue contract.·       [05:48] Melissa on speaking for revenue-based funding as it’s applied to founders underserved by venture capital.·       [06:47] The reason why some companies are underserved by traditional venture capital.·       [08:39] Why she wanted the flexibility to invest without being dependent on exit as the primary way of delivering value.·       [11:44] The importance of having optionality – the ability to survive and sustain without dependency on someone else’s money.·       [16:07] The importance of figuring out how to be a good capital operator to hit your growth goals.·       [18:18] The qualities that make a great founder, as Melissa has seen working with founders.·       [20:47] The healthiest form of grit – the authentic ability to process good and bad and start fresh.·       [24:56] Melissa unpacks the toxic masculinity aspect within the investor side of the industry.·       [30:47] Random questions with Melissa!Memorable Quote:·       “You’ve got to look at your business, your goals, your plan, and then have a capital strategy that matches that.”- Melissa [16:07]

How do you take lessons from a high-performing culture and venture into a different industry? As an innovative individual, you don’t always have to enjoy the experience of learning something to use those lessons to build something bigger for yourself.In this episode of The Capital Stack, we have Will Drewery, an early-stage venture founder, tech investor, supply chain enthusiast, and experienced board member. He has a track record of bringing technical products from the idea stage to reality for iconic brands such as Tesla and Astra.Listen in to learn the responsibilities Will handled at Tesla and how that experience enabled him to start his own company. You will also learn the importance of the American manufacturing base stepping up and automating back-office operations to make things easier.What You Will Discover:·       [00:00] Intro·       [04:12] Will explains the meaning of advanced manufacturing technology and how it’s used.·       [05:51] The tech advancement that’s drastically bringing down the cost of advanced manufacturing and making it accessible.·       [09:48] He describes his experience working as a contractor for the US government and the lessons he learned working at Tesla.·       [16:26] How former employees of Tesla and SpaceX are reapplying their learned lessons into new industries.·       [18:12] He shares his experience working at Astra and the career milestones he made while there.·       [19:40] How Diagon is building a platform for manufacturers to find manufacturing & automation equipment.·       [29:00] The ways American manufacturers can step up to digitize and make things easier in the industry.·       [31:58] The opportunity and healthy demand that exist in machining and manufacturing.·       [33:12] Random questions with Will!Memorable Quote:·       “You can be grateful for the opportunity even if you didn’t always enjoy the experience of going through it.”- Will [16:04]Connect with Will:·       LinkedIn: https://www.linkedin.com/in/williamdrewery/

How does your company facilitate online payments? As a merchant, online payment facilitation isn’t easy, especially if you’re a software company operating in the processing volume of $50M to $2B.In this episode of The Capital Stack, we have Caleb Avery, the CEO and Founder of Tilled, a fintech and PayFac-as-a-service company helping software companies monetize their payments. He is redrawing the map for online payment facilitation—and changing the landscape of fintech in the process.Listen in to learn how Tilled makes payment facilitation easier for software companies and approaches them in an educational and consultative way. You will also learn the importance of getting customer feedback to understand what’s working and not working with your payment model. What You Will Discover:·       [00:00] Intro·       [02:50] Caleb on his background and where he saw the opportunity to help software companies monetize payments.·       [04:30] He explains the layers of how payments move from the consumer to the merchant.·       [07:17] How risk differs with different payment models, plus the advantages of the PayFac process in risk absorption.·       [10:02] The processing volume that would make sense for a PayFac investment.·       [12:18] How Tilled makes the PayFac payment model easier, plus where it makes sense to move from ISO to PayFac.·       [15:37] The impact of creating a payment monetization strategy that companies are starting to understand.·       [17:23] Why Tilled approaches software companies in an educational and consultative way. ·       [20:17] How effective payment monetization has allowed software companies to compress the margin for their SaaS products.·       [21:43] The importance of getting customer feedback to understand what’s and what’s not working.·       [24:33] He describes Tilled future plans in scaling and focusing on customer relations.·       [26:33] Random questions with Caleb!Memorable Quote:·       “Part of the reason why you’re seeing more of that margin compression on the SaaS products is because some of the bigger competitors have figured out how to effectively monetize the payments.”- Caleb [20:53]Connect with Caleb:·       LinkedIn: https://www.linkedin.com/in/caleb-avery/

This week I talk to Peter Morgan co-founder and CSO of Phylum- A malware cybersecurity company. Pete talks to me about malware like I am five years old as well as other applications within the cybersecurity technology stack. How well do you understand cybersecurity, and is your organization well protected? Ransomware has become a cybersecurity nightmare for many organizations in America today, so it’s important to know how it works. In this episode of The Capital Stack, we have Pete Morgan, the Chief Security Officer and co-founder of Phylum, a software supply chain security company. He shares his career journey in high-level cybersecurity before starting Phylum. Listen in to learn how a penetration tester is hired to locate weaknesses by breaking into an organization’s computers and compromising them. You will also learn about the categories of cybersecurity that software companies are currently addressing. What You Will Discover: • [00:00] Intro • [01:34] How Pete’s love for computers from a young age turned into a career in high-level cyber security. • [04:30] The penetration tester – hired to find weaknesses by breaking into computers and compromising them. • [06:33] Understanding ransomware – how hackers turn a computer compromise into money. • [09:44] The financial damage of ransomware on organizations plus the challenge with cyber security insurance. • [12:44] He explains the law against cybercrimes in America and on an international level. • [17:27] The market map of software companies and vendors currently addressing cybersecurity. • [22:35] How Phylum’s product is extremely purpose-built with reliable and reproducible software. • [27:08] Why the level of software tools automation is making it difficult to defend. Memorable Quote: • “It’s pretty tough to get cybersecurity all right all the time in a large organization that’s moving fast.”- Pete [25:40] Connect with Pete: • LinkedIn: https://www.linkedin.com/in/peterjmorgan98/

Why do you care about the big valuation? Are you taking millions that you don’t necessarily need to generate returns? You can generate better returns and fund better companies without needing large capital raises at every stage.In this episode of The Capital Stack, we have Corey Kossack, the Founder & CEO of Aspireship, an online platform that trains you for sales careers in the SaaS industry, then helps you show off your skills to fast-growth tech companies.Listen in to learn how to be an outstanding, fearless investor who sees and invests in opportunities rather than numbers. You will also learn how Aspireship trains people to gain skills in different industries and helps companies reduce high staff turnover.What You Will Discover:·       [00:00] Intro·       [02:18] Corey’s belief that we can generate better returns and fund better companies without large capital raises.·       [08:40] Why the fund structure design needs to change, not to prioritize big valuation.·       [13:41] He explains what Aspireship does, how they help employers, and its growth strategy.·       [17:51] The companies Aspireship works with, plus how they train people to gain skills in different industries.·       [22:42] He explains his focus on business growth with efficiency as he continues to learn.·       [27:00] How to be an outstanding investor investing in opportunities rather than numbers.·       [32:56] Corey on his angel investing ventures and how that’s working out for him.·       [35:25] The impact of AI on business and why Corey worries about its impact on the workforce.·       [36:50] How Aspireship is building a trusted and powerful brand that will expand exponentially.Memorable Quote:·       “The rules for investing are so prescriptive everyone’s following the same playbook.”- Cory [30:48]Connect with Corey:·       LinkedIn: https://www.linkedin.com/in/coreykossack/