Startup Hustle

In this episode, Matt Watson interviews Andrew Plato, a seasoned entrepreneur and author of 'The Founder's User Manual.' They discuss the challenges of entrepreneurship, the importance of differentiation in a competitive market, and the role of trust and credibility in business. Andrew shares insights from his experiences, emphasizing the need for startups to establish a unique identity, navigate...

Adam Robinson, founder and CEO of Retention, discusses his new product RB2B and the importance of simplicity and profitability in building a successful business. He emphasizes the value of bootstrapping and achieving $10 million ARR before considering raising funds. Adam challenges the traditional venture-backed model and highlights the benefits of owning a profitable business that generates milli...

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 an...

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 po...

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 t...

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...

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 impac...

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 Cap...

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 contribut...

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. Marcus also shares insights i...

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...

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...

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 lead...

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.  Th...

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 emphasize...

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...

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...

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...

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...

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 Microsof...

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...

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...

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...

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 ear...

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...