Episodes

Tyler Lieber, co-founder and CEO of Coconut VA, joins Matt Watson on the Startup Puzzle podcast to discuss the benefits and challenges of hiring virtual assistants (VAs) in the Philippines. They share their personal experiences with remote hiring and highlight the importance of trust and communication in working with VAs. Tyler explains that VAs can assist with a wide range of tasks, from email and calendar management to event planning and project coordination. They also discuss the unique advan...

In this episode, Matt Watson interviews Nimrod Vromen, author of Prompting Happiness, about the future of generative AI and its impact on various aspects of life. They discuss the role of lawyers in startups, the importance of focusing on distribution rather than protection in the early stages, and the need for founders to have a clear and comprehensive founders agreement. They also explore the potential of AI in enhancing communication, language translation, and interconnectivity among humans. ...

In this episode, Matt Watson and Ian Myers discuss the topic of hiring global talent. Ian shares his experience of starting a company in Sri Lanka and leveraging the highly skilled workforce there. They also discuss the challenges of scaling service-based businesses and the importance of upskilling and mentoring employees. Ian highlights the benefits of hiring talent from different countries and the opportunities it creates for both the employees and the local economies. They also touch on the c...

Chris Callen, founder and CEO of Plot, discusses his journey in the construction technology industry and the challenges of coordinating job sites. He shares his experience with his first software startup and the lessons he learned from it. Callen explains how Plot's job site coordination software helps streamline the delivery and procurement processes in construction. He also discusses the role of AI in the industry and the importance of building trust with customers. The episode concludes with ...

David Sinkinson, co-founder of AppArmor, shares his entrepreneurial journey and the lessons he learned along the way. He challenges startup myths and emphasizes the importance of finding the right co-founder. The conversation covers topics such as the need for funding, the psychology of being a founder, the evolution of AppArmor's product, the slow sales cycle in selling to colleges, and the impact of COVID-19 on the business. AppArmor was eventually sold for $40 million. The conversation explo...

In this episode, Matt Watson interviews Dan Kerr from Flyover Capital, discussing the evolving landscape of venture capital in the Midwest, particularly in Kansas City. They explore the importance of networking for founders, the structure of the upcoming Mid-by-Midwest event, and the changing dynamics of funding, including the rise of debt and royalty financing. Dan shares insights on Flyover Capital's investment strategy, the challenges startups face in revenue generation, and the growing vari...

In this episode, Matt Watson interviews Michelle Denogean, the Chief Marketing Officer of MindTrip and author of the book 'Grow Up.' They discuss the challenges that founders face when growing their companies and the importance of having a diverse team with different superpowers. Michelle introduces four superpowers: innovator, builder, connector, and persuader, and explains how each one contributes to the growth of a company. They also talk about the blind spots that come with each superpower a...

In this episode, Matt Watson interviews Markus Waite, the President of Empara and CIO of Goodroot, about healthcare technology. They discuss the challenges and complexities of the healthcare industry, the role of generative AI in simplifying healthcare processes, the high cost of healthcare in the United States, and the need for transparency and cost-saving solutions. Markus also shares insights into the work of Goodroot, a company that focuses on solving healthcare problems through innovative s...

In this episode, Matt Watson interviews Keith Harrington, the founder and COO of Novel Capital, about non-dilutive capital and alternative funding options for startups. They discuss the different types of capital available, such as revenue-based financing and venture debt, and the importance of understanding when and how to raise money. Keith emphasizes the need for entrepreneurs to have access to information, capital, and tools to make informed financing decisions. They also touch on the risks ...

Christian Hammer, founder and CEO of Vala AI, joins Matt Watson on the Startup Hustle podcast to discuss AI for software development and the concept of technical debt. They explore the challenges of bridging the gap between business needs and technology, the different definitions of tech debt, and the importance of keeping up with the rate of change in the industry. Christian shares insights into Vala AI's platform, which aims to provide a holistic view of an organization's tech stack and help i...

In this episode, Matt Watson and Ryan Dowdy discuss the difference between professional service companies and SaaS companies. They explore the challenges and opportunities of scaling a service-based business and the importance of sales and distribution in entrepreneurship. They also touch on the significance of personal branding for founders and the role it plays in building trust and thought leadership. The conversation focuses on the importance of values alignment, personal branding, and qual...

In this episode, Matt Watson and Brett Sears discuss the importance of customer onboarding and training in software companies. They highlight the need for software companies to focus on getting customers to see value and have an 'aha' moment as quickly as possible. They also emphasize the significance of understanding the perspective of new users and providing a seamless onboarding experience. The discussion delves into the evolving landscape of user onboarding and customer success, highlightin...

In this episode, Matt Watson and Ryan Dowdy discuss the importance and benefits of being recognized on the Inc 5000 list. They explore the motivations behind winning awards and the impact it has on company culture, employee morale, and recruiting. They also highlight the value of third-party validation and how it builds credibility and trust with customers and investors. The conversation emphasizes the significance of celebrating wins and the role of awards in showcasing a company's success. Ta...

Sim Desai, founder and CEO of Hive, discusses the creation of a secondary stock market for private companies. He explains the challenges of the current system, where selling private stock options is fragmented and opaque. Hive aims to centralize and automate the secondary market process, providing a platform for buyers and sellers to connect. The target market for Hive ranges from small companies with a post-money valuation of $300-500 million to large companies like SpaceX and OpenAI valued at ...

In this episode, Matt Watson interviews Vijay Rajendran, the coach and CEO of Startup System, about startup resilience and fundraising in the current economic climate. They discuss the challenges faced by startups, the importance of being cashflow positive, and the need to adapt and refine value propositions. They also explore the role of marketing, the significance of communication and delegation for founders transitioning to CEOs, and the value of aligning goals and values. Vijay offers coachi...

In this episode, Matt Watson interviews Dale Walden, the founder of Njord & Co, a SaaS B2B marketing company. They discuss the importance of positioning in marketing and how it can help companies focus on their target audience. Dale shares his experiences in the B2C and B2B worlds and emphasizes the need for founders to niche down and focus on a specific customer profile. They also discuss the challenges of transitioning from a founder to a leader and the importance of building a talented team. ...

In this episode of the Startup Hustle podcast, Matt Watson interviews Rich Brooks, the president of Flight New Media, about digital marketing and the Remarkability Formula. They discuss the impact of AI on marketing, the importance of finding your uniqueness, and the benefits of niching down. Rich explains the four lenses of remarkability: find, focus, frame, and forge. He also shares insights on recurring revenue and the value of building relationships with clients. Rich's podcast, Agents of C...

In this episode of the Startup Hustle podcast, Matt Watson interviews Ozan Unlu, the founder and CEO of Edge Delta, an observability company. They discuss the challenges of managing large amounts of data in complex production environments and the need for developers to have access to production data without compromising security. Ozan shares his journey from being a software developer at Microsoft to becoming a solution architect and eventually starting his own company. They also delve into the...

Neelima Paraskar, founder and CEO of Snap IT, discusses her journey in the tech industry and the challenges of hiring and retaining talent in the IT field. She shares how Snap IT started as a training company to address the lack of affordable and skilled engineers in Kansas City. Neelima also talks about the impact of AI on software development and the changing skills required in the industry. She highlights the importance of certifications and government contracts in growing her business. Neel...

Maria Flynn, founder and CEO of AmbioLogix, discusses her background in healthcare technology, entrepreneurship, and the digital health industry. She shares insights from her book 'Make Opportunity Happen' and provides valuable advice for entrepreneurs. The conversation covers topics such as urgency, finding opportunities, and practical advice for business success. Urgency is a critical factor in entrepreneurship, and it's important to align urgency with partners and customers to drive progress...

Thinking of taking your software global but worried about navigating different markets and regulations? We've got you covered! Join Matt Watson as he explores the world of SaaS in Sweden with Nicholas Lilja, the founder and CEO of Younium, a billing and subscription management platform. In this episode, you'll discover: The unique challenges and opportunities of launching a SaaS company in Sweden (hint: it's not all about Vikings!) How to scale down to scale up - practical strategies for co...

Ever wonder why amazing entrepreneurs sometimes struggle to ask for what they want? This episode explores the surprising roadblocks that can hold even the most successful founders back. We'll be joined by Kenneth Berger, an executive coach who's seen it all—from Slack's explosive growth to the unique challenges faced by startup founders. Here's what you won't want to miss: Secrets from Slack's early days: Kenneth shares behind-the-scenes insights on scaling a product with millions of users, a...

How does an experienced retail expert construct a cutting-edge financial platform? Prepare yourself because that's precisely the fascinating topic we're exploring in this episode! Our guest today, Brad Parker, takes us on a wild ride through his 20-year retail experience, growing a business from a single location to a multi-million dollar empire. But Brad's story doesn't end there. He saw a gap in the market and decided to leverage his retail expertise to create FormPiper, a revolutionary platf...

Have you ever dreamt of launching a startup but worried about the dangers of scaling too quickly? Or maybe you're already running a business that feels stuck, unable to reach its full potential. This is the podcast for you. Join host Matt Watson as he explores the fascinating world of entrepreneurship with Dave Hirsch, a seasoned investor and turnaround specialist. Together, they'll crack the code on fundraising, growth strategies, and how to avoid the common pitfalls that can sink even the mos...