Episodes

Oct. 31, 2024

Bootstrapping to $10M, The Future of Inbound Sales

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 mill...

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Oct. 24, 2024

The Business of Virtual Assistants

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 experienc...

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Oct. 17, 2024

Startup Lawyer Advice, Future Impact of AI

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 o...

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Oct. 10, 2024

Building a Global Service Business

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 chall...

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Oct. 3, 2024

Construction Tech, Building Additional Products

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 le...

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Sept. 26, 2024

Startup Different

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...

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Sept. 24, 2024

MidxMidwest and the State of Venture Capital in 2024

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, ...

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Sept. 19, 2024

Founder Super Powers

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 importan...

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Sept. 12, 2024

Healthcare Tech Needs a Check Up

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 A...

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Sept. 5, 2024

How to Access Non-Dilutive Funding

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, s...

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Aug. 29, 2024

Technical Debt, Bridging Business & Tech

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 b...

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Aug. 22, 2024

SaaS vs Professional Services, Business Growth

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 importanc...

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Aug. 15, 2024

Product Adoption & Reducing Churn

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...

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Aug. 13, 2024

Why the Inc 5000 is a Big Deal

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 m...

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Aug. 8, 2024

Creating a Private Stock Market

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. Hiv...

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Aug. 6, 2024

Transition from Founder to CEO, Resiliency, Avoiding Burnout

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 import...

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Aug. 1, 2024

Startup Positioning

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 audienc...

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July 25, 2024

The Remarkability Formula

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 impo...

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July 18, 2024

Scaling an Enterprise Data Startup

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...

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July 11, 2024

Building Up Tech Talent

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 …

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July 4, 2024

How to Make Opportunity Happen

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 valuab...

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June 27, 2024

The Complexities of SaaS Billing

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 C...

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June 20, 2024

Asking for What You Want, Slack Early Days

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 e...

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June 13, 2024

From Pet Stores to SaaS & The Steps to Success

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 w...

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