1,306 episodes

Startup Hustle is a podcast for entrepreneurs, by entrepreneurs.  With the mission of telling the real story of startups and entrepreneurs, topics range from funding to failure and beyond.  If you want to start, own, or build a business then you're in the right place.   

Startup Hustle Startup Hustle

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    • 5.0 • 1 Rating

Startup Hustle is a podcast for entrepreneurs, by entrepreneurs.  With the mission of telling the real story of startups and entrepreneurs, topics range from funding to failure and beyond.  If you want to start, own, or build a business then you're in the right place.   

    Why Startups Get Stuck & The Pitfalls of Raising Money

    Why Startups Get Stuck & The Pitfalls of Raising Money

    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 most promising startups.

    In this episode, you'll hear:


    Why too much money can be a bad thing for your business (and how to raise capital responsibly)
    The surprising truth about the chances of startup success (hint: it's not what you think!)
    The secret weapon for achieving long-term growth (it's not what you think either!)
    Why some startups end up selling, and the challenges they face along the way
    How to avoid common scaling mistakes that can derail your business

    So, whether you're a budding entrepreneur or a seasoned business leader, tune in and get ready to unlock the secrets of building a sustainable, thriving company. Together, we'll debunk the myths, confront the challenges, and ignite your entrepreneurial journey!

     

     

    Find Startup Hustle Everywhere:

    https://gigb.co/l/YEh5

     

    This episode is sponsored by Full Scale:

    https://fullscale.io/

     

    Visit the Metamorph Partners website: 

    https://www.metamorphpartners.com/ 

     

    Learn more about Dave Hersh:

    https://www.linkedin.com/in/davehersh/ 

     

    Sign up for the Startup Hustle newsletter:

    https://newsletter.startuphustle.xyz/ 

     

     

    Highlighted Discussion Points


    Entrepreneurship, fundraising, and growth with a focus on avoiding premature scaling and false narratives. 0:31
    Raising capital for startups, focusing on responsible growth and market realities. 4:25
    Entrepreneurship, fundraising, and growth challenges. 8:27
    Buying and growing profitable businesses. 13:21
    Reasons why startups sell, including investor pressure and growth challenges. 15:46
    Common pitfalls in scaling startups include hiring the wrong team and over-engineering sales and marketing. 20:43
    Entrepreneurship, business growth, and leadership. 25:11
    Entrepreneurship, leadership, and company transformation. 29:37

     
    See omnystudio.com/listener for privacy information.

    • 37 min
    Mastering Software Sales

    Mastering Software Sales

    Have you poured your heart and soul into building a game-changing SaaS product, only to find crickets chirping when it comes to sales? Fear not, fellow entrepreneur, because you're in the vast company of frustrated founders.

    This episode of  "Mastering Software Sales" dives deep into the trenches of selling software with industry expert Matt Wolach. Matt, a former technical founder who himself battled fierce competition in the early days, pulls back the curtain on the biggest challenges SaaS founders face: reaching the right audience, educating them on the value you offer, and ultimately, closing the deal.

    But fear not! Matt also shares the golden nuggets of wisdom he learned while building his own Inc. 500 company. We'll talk product-led growth strategies, the importance of results-oriented demos, and how to scale your sales with a repeatable process (no more throwing darts in the dark!).

    Join Matt Watson and Matt Wolach as they unpack powerful lead generation channels, explore the art of uncovering customer pain points (we're talking metaphorical knife-twisting!), and demystify the creation of ideal customer profiles for laser-focused sales efforts.

    So, whether you're a seasoned founder or a fresh-faced startup warrior, this episode is your roadmap to SaaS sales success. Buckle up, hit play, and get ready to transform your closing rates!

     

    Find Startup Hustle Everywhere:

    https://gigb.co/l/YEh5

     

    This episode is sponsored by Full Scale:

    https://fullscale.io

     

    Visit the Xsellus website: 

    http://www.mattwolach.com 

     

    Learn more about Matt Wolach:

    https://www.linkedin.com/in/mattwolach

     

    Sign up for the Startup Hustle newsletter:

    https://newsletter.startuphustle.xyz

     

     

    Highlighted Discussion Points


    Challenges faced by SaaS founders in identifying and selling their products. 0:31
    Challenges in selling software include a lack of understanding and difficulty reaching the target audience. 5:35
    Product lead growth strategies and the importance of educating clients on industry changes and results. 8:24
    Scaling a software company through inbound and outbound lead generation methods. 11:32
    Various business lead generation channels include content marketing, engineering as marketing, and SEO. 16:25
    Sales strategies, including personal branding, lead generation, and problem-solving in discovery calls. 18:37
    Identifying and addressing pain points in sales and marketing. 23:25
    Identifying ideal customer profiles and buyer personas for startups. 28:19
    Prioritizing sales efforts based on market knowledge and closing skills. 30:44
    SAS sales strategies and metrics with industry expert Matt Wolach. 35:33

     
    See omnystudio.com/listener for privacy information.

    • 39 min
    How Honeycomb Created a New Product Category: Observability

    How Honeycomb Created a New Product Category: Observability

    Do you feel like you're flying blind when it comes to your software?

    In today's episode, we dive deep into the world of observability - it's not just monitoring on steroids, and we'll explain why. Our guest, Charity Majors, co-founder and CTO of Honeycomb, will break down the concept and how it's changing the game for developers.

    Get ready to hear about:


    Observability 1.0 vs. 2.0: Is your toolkit stuck in the past? We'll explore the evolution of this critical practice.
    AI in Debugging: Friend or foe? We'll discuss the role of AI in software analytics and why it won't solve all your problems (but can definitely help!).
    The Single Source of Truth: Tired of juggling metrics, logs, and traces? Honeycomb's approach might be the answer you've been looking for.
    Building a Boring Company: Forget ping pong tables and nap pods. We'll chat about why a well-run, functional company might be the key to long-term success.

    So buckle up, developers and ops folks! This episode is packed with insights to help you see your software like never before.

     

    Find Startup Hustle Everywhere:

    https://gigb.co/l/YEh5

     

    This episode is sponsored by Full Scale:

    https://fullscale.io

     

    Visit the Honeycomb.io website: 

    https://www.honeycomb.io

     

    Learn more about Charity Majors:

    https://www.linkedin.com/in/charity-majors 

     

    Sign up for the Startup Hustle newsletter:

    https://newsletter.startuphustle.xyz

     

    Highlighted Discussion Points


    Observability in software development, its definition and evolution. 0:31
    Software observability and analytics, AI's limitations in solving complex problems. 3:54
    Challenges of creating a new market for software tools, particularly in selling to developers and overcoming resistance to change. 9:03
    Challenges of building a successful tech company, particularly in sales and marketing. 14:35
    Leadership, sales, and transparency in a startup. 19:24
    Leadership, growth, and prioritizing a well-run company over a "fun" one. 24:46
    Honeycomb's product development and future plans, including new features and architecture improvements. 29:17
    Observability in software development with Charity Majors, CTO of Honeycomb. 33:21

     
    See omnystudio.com/listener for privacy information.

    • 38 min
    AI in Healthcare, First-Time CTO

    AI in Healthcare, First-Time CTO

    Did you know traditional breast cancer screenings can miss early signs of the disease?

    In this episode, we get an exclusive look into MedCognetics, a company using AI to revolutionize breast cancer detection. Matt Watson chats with guest Tim Cogan, MedCognetics co-founder & CTO, about how AI can:


    Catch cancer earlier: Imagine AI spotting subtle abnormalities that might escape the human eye, leading to earlier intervention and potentially better outcomes.
    Free up doctors' time: AI could become a doctor's partner, prioritizing patients and allowing for more focused care.
    Improve accuracy: AI algorithms trained on vast datasets might produce more consistent and accurate diagnoses than traditional methods.

    But developing AI for healthcare isn't without its challenges. We'll also discuss:


    The road to FDA approval: The rigorous process of getting AI-powered medical tools cleared for use ensures patient safety and efficacy.
    Building unbiased AI: Ensuring diverse datasets and addressing potential biases in AI development is crucial for fair and accurate diagnoses.
    The changing role of the CTO: Tim Cogan, a seasoned software developer, shares how his perspective on technology has shifted to focus on business goals and, ultimately, improving patient care.

    Join our host, Matt Watson, a tech leader with over 20 years of experience, and Tim Cogan as they explore the exciting potential of AI in breast cancer screening. This episode is a must-listen for anyone interested in the future of healthcare, medical technology, and the fight against cancer.

     

     

    Find Startup Hustle Everywhere:

    https://gigb.co/l/YEh5

     

    This episode is sponsored by Full Scale:

    https://fullscale.io

     

    Visit the MedCognetics website: 

    https://www.medcognetics.com 

     

    Learn more about Tim Cogan:

    https://www.linkedin.com/in/timothy-cogan 

     

    Sign up for the Startup Hustle newsletter:

    https://startuphustlenews.com

     

     

    Highlighted Discussion Points


    Using AI to improve breast cancer screening process. 0:32
    Developing AI software for breast cancer detection. 4:37
    Developing AI for medical image analysis, challenges, and potential impact on healthcare. 9:47
    AI in healthcare, prioritizing patient care, and CTO's role in software development. 16:17
    Shifting mindset from technical expertise to problem-solving and business outcomes in software development. 20:51
    FDA approval process for AI-powered cancer diagnosis tool. 27:34
    AI in medical imaging, the potential for accuracy improvement. 31:50

     
    See omnystudio.com/listener for privacy information.

    • 38 min
    Outbound Sales & Gamify Sales

    Outbound Sales & Gamify Sales

    Are you tired of the same old outbound sales tactics that just don't work?

    In this episode, we'll be joined by entrepreneur Steve Claydon, founder of The Outbound Game, to chat about shaking things up with gamification and personalization.

    Steve used to be stuck in the trenches of sales, and let's face it, it can be a grind. But he realized there had to be a better way to motivate salespeople and drive results. That's where gamification came in. We'll hear how Steve used fun and competition to turn photo uploads and inventory management into a game, skyrocketing engagement and success for car dealerships.

    But gamification is just one piece of the puzzle. Steve will also share his insights on personalized sales strategies, the power of video content, and why focusing on quality over quantity is the key to sales and marketing success. So, ditch the generic emails and phone calls, and get ready to learn how to stand out from the crowd and crush your goals.

     

     

    Find Startup Hustle Everywhere:

    https://gigb.co/l/YEh5

     

    This episode is sponsored by Full Scale:

    https://fullscale.io

     

    Visit the Outbound Game website: 

    https://www.outbound.game 

     

    Learn more about Steve Claydon:

    https://www.linkedin.com/in/thesteveclaydon 

     

    Sign up for the Startup Hustle newsletter:

    https://startuphustlenews.com

     

     

    Highlighted Discussion Points


    Sales, marketing, and gamification with entrepreneur Steve Clayton. 0:31
    Incentivizing salespeople to take photos and upload inventory using gamification. 3:27
    Outbound sales strategies, emphasizing the importance of personalized efforts. 7:36
    Personalized sales strategies and the use of AI in outbound email campaigns. 12:08
    Personalized video content for outbound marketing. 16:32
    Prioritizing marketing efforts and simplifying strategies to achieve goals. 20:09
    Sales and entrepreneurship, prioritizing quality over quantity. 24:53
    Entrepreneurship, sales, and delegation. 27:26
    Gamifying sales and marketing with Outbound Game. 32:01

     
    See omnystudio.com/listener for privacy information.

    • 38 min
    Generative AI & Legal Tech

    Generative AI & Legal Tech

    Are robots about to take over your lawyer's job?

    Not quite, but Artificial Intelligence is poised to revolutionize the legal industry. In this episode, Matt Watson ventures into the world of immigration law with Josh Waddell, co-founder of VisaLaw.ai.

    Josh isn't just another lawyer; he's a legal tech pioneer who saw the limitations of traditional practice and decided to disrupt it from within. We'll hear how his law firm embraced AI to automate tedious tasks, leaving lawyers free to focus on complex cases and high-touch clients.

    But innovation doesn't come easy. Josh shares the challenges of building trust in a skeptical legal market and the surprising pivot that led to the creation of VisaLaw.ai, a powerful AI tool for immigration lawyers.

    Is this the future of legal practice? Tune in to find out if AI is a friend or foe and how even the most traditional professions can leverage technology to stay ahead of the curve.

     

    Find Startup Hustle Everywhere:

    https://gigb.co/l/YEh5

     

    This episode is sponsored by Full Scale:

    https://fullscale.io

     

    Visit the Visalaw.ai website: 

    https://www.visalaw.ai

     

    Learn more about Josh Waddell:

    https://www.linkedin.com/in/jnwaddell

     

    Sign up for the Startup Hustle newsletter:

    https://newsletter.startuphustle.xyz

     

    Highlighted Discussion Points


    Using generative AI in the legal landscape with a focus on a law firm's innovative approach. 0:52
    Immigration law and AI-powered legal tools for automating complex document drafting. 4:09
    Using AI to automate legal document drafting and research. 8:13
    Creating an AI-powered legal research tool for immigration lawyers. 12:53
    Developing and selling AI-powered legal tools. 17:51
    Startup success factors, including industry expertise and following. 22:35
    Potential disruption of the legal industry by tech companies. 26:20
    AI-powered legal research tool for immigration lawyers. 31:00
    Using generative AI in the legal field, potential benefits and limitations. 36:55

     
    See omnystudio.com/listener for privacy information.

    • 44 min

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