

Startup Hustle
Startup Hustle
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.
Episodes
Mentioned books

Jun 27, 2024 • 33min
The Complexities of SaaS Billing
Nicholas Lilja, Founder and CEO of Younium, shares invaluable insights on launching a SaaS company in Sweden, navigating regulatory nuances, and understanding cultural differences. He emphasizes the importance of flexible billing systems and adapting pricing models to meet customer needs. Lilja also discusses strategies for focused market expansion and the critical role of defining an Ideal Customer Profile to drive growth. Tune in for expert tips on conquering the European market and mastering the complexities of SaaS billing!

Jun 20, 2024 • 35min
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 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, and the crucial lessons learned along the way. The coaching advantage: Discover how personalized coaching can help entrepreneurs overcome personal hurdles and become better leaders. The power of asking: We'll crack the code on why entrepreneurs often struggle to ask for what they want and equip you with practical tips to finally go for it! Following your gut: Learn how to trust your instincts and overcome the fear of rejection that holds so many back. Join us for an episode packed with actionable advice and inspiring stories that will empower you to become a more confident and successful entrepreneur. Find Startup Hustle Everywhere: https://gigb.co/l/YEh5 This episode is sponsored by Full Scale: https://fullscale.io Visit the Kenneth Berger Consulting website: https://kberger.com Learn more about Kenneth Berger: https://www.linkedin.com/in/kberger Sign up for the Startup Hustle newsletter: https://newsletter.startuphustle.xyz Highlighted Discussion Points Why entrepreneurs struggle to ask for what they want, with tips from an executive coach. 0:31 Slack's early growth and product development. 1:19 Product development and growth of Slack, with insights on lessons learned and challenges faced. 4:17 Coaching, personal growth, and business challenges. 9:06 Entrepreneurship, coaching, and asking for what you want. 12:24 The power of asking for what you want in life, despite fear of rejection. 16:12 Asking for what you want in life, entrepreneurship, and business. 19:10 Asking and accepting responses with intention and clarity. 24:29 Executive coaching, following gut instincts, and overcoming fears. 27:28 See omnystudio.com/listener for privacy information.

Jun 13, 2024 • 45min
From Pet Stores to SaaS & The Steps to Success
Brad Parker, a retail expert turned tech entrepreneur, shares insights on hiring developers, prioritizing tasks, building a sales team, and implementing reservation programs. He discusses his journey from retail to SaaS and the challenges of scaling a business, offering actionable advice for entrepreneurs at any stage.

Jun 11, 2024 • 38min
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.

Jun 6, 2024 • 41min
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.

Jun 4, 2024 • 40min
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.

May 30, 2024 • 40min
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.

5 snips
May 28, 2024 • 39min
Outbound Sales & Gamify Sales
Entrepreneur Steve Claydon, founder of The Outbound Game, shares insights on gamifying sales to boost engagement and success in car dealerships. He emphasizes personalized sales strategies, video content, and quality over quantity for marketing success. Learn how to stand out and crush your goals in this episode!

May 23, 2024 • 46min
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.

22 snips
May 21, 2024 • 40min
The 7 Types of a CTO
The podcast features Adelina Chalmers, the 'Geek Whisperer,' discussing the evolving role of a startup CTO. They explore self-awareness, strengths, and weaknesses of CTOs, aligning technology with business goals, overcoming challenges, and avoiding burnout. The episode provides essential insights for navigating the world of CTO roles.