1,301 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

    • Business
    • 4.6 • 230 Ratings

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.   

    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
    The 7 Types of a CTO

    The 7 Types of a CTO

    Ever heard the term "CTO" and wondered what it actually means? In the wild world of startups, the role can be a bit of a mystery. 

    In this episode, we're joined by Adelina Chalmers, also known as the "Geek Whisperer." Buckle up as we dissect the ever-evolving role of a startup CTO. We'll crack open the code on how CTOs can translate techie jargon into investor gold, and explore the crucial (but often overlooked) skill of self-awareness for these tech titans.

    This episode is packed with insights to help you:


    Understand the evolving role of a startup CTO
    Identify your ideal CTO strengths and weaknesses
    Align technology with your business goals for success
    Overcome common CTO challenges and avoid burnout

    Don't miss this essential guide for anyone navigating the exciting, and often messy, world of CTO roles!

     

     

    Find Startup Hustle Everywhere:

    https://gigb.co/l/YEh5

     

    This episode is sponsored by Full Scale:

    https://fullscale.io/

     

    Visit the Geek Whisperer’s Associates website: 

    https://www.geekwhisperer.co.uk/ 

     

    Learn more about Adelina Chalmers:

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

     

    Sign up for the Startup Hustle newsletter:

    https://newsletter.startuphustle.xyz/ 

     

    Highlighted Discussion Points


    CTO roles in startups, evolution, and responsibilities. 0:33
    CTO roles and responsibilities in startups, with a focus on self-awareness and understanding one's strengths and weakness. 6:03
    Different types of CTO roles, including technical visionary, business strategist, and more. 14:33
    CTO roles, sales, and marketing in tech companies. 20:28
    Importance of understanding customer needs for software development and business success. 25:02
    CTO roles, challenges, and strategies for success. 30:39

     
    See omnystudio.com/listener for privacy information.

    • 39 min
    Pivoting & Bootstrapping to 1000 Customers

    Pivoting & Bootstrapping to 1000 Customers

    Ever gotten hit with a chargeback? You're not alone. In this episode, we dive into the world of e-commerce fraud with Qi Cao, the co-founder and CEO of Chargeblast, a company helping merchants fight back against unfair chargebacks.

     

    Qi Cao went from scientist to entrepreneur after experiencing the pain of chargebacks firsthand. Now, he's helping businesses win back revenue and avoid costly disputes. But Chargeblast's journey wasn't always smooth sailing. We'll hear how Qi Cao pivoted from B2C to B2B, bootstrapped his company, and leveraged data to achieve explosive growth.

     

    We'll also discuss:

     


    Chargebacks in e-commerce: Why merchants lose most disputes, and how to fight back.
    Bootstrapping and growth strategies: How Chargeblast achieved success without venture capital.
    Cost-saving hacks for startups: Cutting costs with AI tools and data-driven decisions.
    The future of AI in FinTech: Separating hype from reality.

     

    So buckle up, entrepreneurs! This episode offers insights to help you win the chargeback battle and grow your business.

     

     

    Find Startup Hustle Everywhere:

    https://gigb.co/l/YEh5

     

    This episode is sponsored by Full Scale:

    https://fullscale.io/

     

    Visit the Chargeblast website: 

    https://www.chargeblast.com/ 

     

    Learn more about Qi Cao:

    https://www.linkedin.com/in/xiuqi-cao/ 

     

    Sign up for the Startup Hustle newsletter:

    https://newsletter.startuphustle.xyz/ 

     

    Highlighted Discussion Points


    Chargeblast is a startup that helps merchants maintain low chargeback rates by alerting them before payment processors. 0:31
    Chargebacks in e-commerce, with insights on industries affected and strategies for resolving disputes. 8:47
    Bootstrapping, unit economics, and growth strategies for startups. 13:06
    Advertising strategies for early-stage companies, focusing on targeting and margin growth. 18:45
    Cost-saving strategies for businesses, including using AI tools and tracking ROI. 23:48
    AI in finance, Chargeblast's product, and entrepreneurship advice. 30:21
    See omnystudio.com/listener for privacy information.

    • 38 min
    The Power of Knowledge & Bootstrapping for 20 years

    The Power of Knowledge & Bootstrapping for 20 years

    Tired of your tedious onboarding routines for new hires and useless knowledge bases no one seems to use?

    This episode of Startup Hustle is your guide to conquering knowledge transfer in the digital age. We chat with Greg DeVore, CEO of ScreenSteps, a software platform that's helping companies slash onboarding times and boost employee productivity.

    In this episode, you'll learn:


    How to ditch the clunky manuals and build a system for capturing and organizing knowledge fast.
    A sneaky trick to separate foundational knowledge from step-by-step instructions, making training materials easier to digest for everyone.
    Why ScreenSteps is like a helpful but opinionated friend, guiding users through processes with laser focus.
    How AI is revolutionizing knowledge management, reducing onboarding times by a whopping 75%! (But beware of AI's love of bad data!)
    The secrets to running a successful business for 20 years, even with your siblings! (Hint: ditch the ego and embrace collaboration.)

    Whether you're a frustrated new hire drowning in documents or a business leader battling knowledge silos, this episode is packed with actionable insights to help you build a thriving, informed workforce.

     

    Find Startup Hustle Everywhere:

    https://gigb.co/l/YEh5

     

    This episode is sponsored by Full Scale:

    https://fullscale.io

     

    Visit the ScreenSteps website: 

    https://www.screensteps.com

     

    Connect with Greg DeVore:

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

     

    Sign up for Startup Hustle's newsletter:

    https://newsletter.startuphustle.xyz

     

    Highlighted Discussion Points


    Knowledge transfer and software development with a focus on ScreenSteps, a knowledge operations platform. 0:51
    How to improve knowledge transfer in organizations by separating foundational and actual knowledge. 4:25
    Creating opinionated software for onboarding and training. 8:51
    Using AI to improve knowledge management and employee training. 12:51
    Using AI in software development, including concerns about accuracy and communication. 17:36
    Running a business with brothers for 20 years, raising capital, and aligning with the right investor. 22:51
    Knowledge transfer and growth strategies for businesses. 27:35
    Changing market behavior and using AI in regulated industries. 33:39

     
    See omnystudio.com/listener for privacy information.

    • 40 min
    The Evolving Role of the CTO

    The Evolving Role of the CTO

    In this compelling episode, join Matt Watson as he sits down with Stefan Schmidt, a seasoned CTO coach and author of the acclaimed book "Amazing CTO." Together, they discuss the pivotal role of a Chief Technology Officer (CTO), exploring crucial insights on when to bring one on board and the critical errors to avoid in the selection process.

    Stefan underscores the importance of idea validation before engaging a CTO or developer and suggests starting with a PowerPoint slide deck to gather feedback. Moreover, he advocates for aligning with a co-founder who not only shares the product vision but also has industry expertise.

    As the conversation unfolds, Stefan navigates the intricacies of company expansion, underscoring the pivotal role of delegating tasks and strategically appointing team leaders. He underscores the critical need for CTOs to shift towards strategic direction, avoiding the trap of being consumed by routine coding tasks.

    Leveraging his wealth of experience, Stefan's book serves as a treasure trove of wisdom, providing CTOs with 140 actionable rules meticulously tailored to their needs. From mastering delegation techniques to nurturing employee growth and circumventing common challenges, his insights offer indispensable guidance for navigating the ever-evolving realm of technology leadership.

     

    Takeaways


    Validate your idea before hiring a CTO or developer
    Find a co-founder who shares the product vision and has experience in the industry
    Delegate tasks and hire team leads as the company grows
    Focus on strategy and vision as a CTO, rather than getting caught up in day-to-day coding

     

    Find Startup Hustle Everywhere:

    https://gigb.co/l/YEh5

     

    This episode is sponsored by Full Scale:

    https://fullscale.io

     

    Visit the Amazing CTO website: 

    https://www.amazingcto.com

     

    Learn more about Stephan Schmidt:

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

     

    Sign up for the Startup Hustle newsletter:

    https://newsletter.startuphustle.xyz 

     

    Highlighted Discussion Points


    Validating startup ideas before hiring developers. 0:51
    Finding a technical co-founder for a startup. 5:22
    Hiring a CTO for early-stage startups, with insights on product vision, ownership, and team leadership. 10:13
    Challenges faced by CTOs in scaling their teams, including delegation, team leads, and maintaining technical expertise. 17:30
    CTOs prototyping and delegating tasks to bring joy to the job. 26:37
    CTO coaching, delegation, and leadership challenges. 30:47

     
    See omnystudio.com/listener for privacy information.

    • 37 min
    From Sales Guy to Tech Founder

    From Sales Guy to Tech Founder

    In this episode of Startup Hustle, Matt Watson interviews Robby Yates, co-founder and Chief Everything Officer of FollowApp, a networking software company. They discuss Robbie's journey from being a salesperson to becoming an IT guy and starting his own company. They also talk about the importance of networking, the challenges of being a non-technical founder, and the benefits of white labeling. Robby shares tips for effective networking and emphasizes building a strong team and listening to others. He also highlights the importance of perseverance and believing in oneself as an entrepreneur.

    Important Takeaways


    Networking is a valuable tool for entrepreneurs and should be approached with intention and a focus on helping others.
    Building a strong team and listening to advisors are crucial for success as a non-technical founder.
    White labeling can be a game changer for a business, allowing for easier promotion and increased revenue.
    Effective networking requires being yourself, not wearing a mask, and following up with contacts.
    Raising funds can be challenging, but networking events can lead to unexpected opportunities.
    It's important to embrace rejection and keep going, believing in oneself and the value of the product or service being offered.

    Don't miss this insightful conversation about becoming a non-tech founder in the tech world. 

     

    Find Startup Hustle Everywhere:

    https://gigb.co/l/YEh5

     

    This episode is sponsored by Full Scale:

    https://fullscale.io

     

    Visit the Follow App website: 

    https://thefollowapp.co 

     

    Learn more about Robby Yates:

    https://www.linkedin.com/in/robert-yates-130105 

     

    Sign up for the Startup Hustle newsletter:

    https://newsletter.startuphustle.xyz

     

    Highlighted Discussion Points


    Creating a software company, challenges and lessons learned. 0:31
    Entrepreneurship, trust, and business growth. 6:03
    Pricing sensitivity and value-based pricing, with a focus on B2B vs. B2C. 10:53
    White labeling software, networking, and app deployment. 12:43
    Networking strategies for introverts and extroverts. 17:49
    Using software to manage networking at events. 22:33
    Entrepreneurship, networking, and fundraising challenges. 25:41
    Building a tech company, overcoming challenges, and staying motivated. 30:44

     
    See omnystudio.com/listener for privacy information.

    • 35 min

Customer Reviews

4.6 out of 5
230 Ratings

230 Ratings

Dan in KC ,

Love it!

Love these folks! Rotating host is a pretty unique idea. Fun to get to know the hosts and their speciality. Seems like that helps produce a ton of good content at scale almost daily. Literally have pulled over my truck and downloaded something or researched something I got from this podcast for my business. 👍🏻👍🏻

Gotchayeah ,

👀

Good podcast but needs better cover art

ASobering ,

Top Tier!

This is one of the most insightful podcasts that I have ever come across! Startup Hustle does such a great job highlighting meaningful conversations with guests who bring so much experience to the table. Highly recommend checking this show out - you won’t be disappointed!

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