
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.
Latest episodes

Aug 6, 2024 • 38min
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 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 for founders transitioning to CEOs, and the value of aligning goals and values. Vijay offers coaching and support to founders in various areas, including funding, go-to-market strategies, team building, and metrics. Takeaways Startups are facing economic uncertainty and longer fundraising timelines, making it important to be cashflow positive and consider alternative funding options. Marketing is crucial during challenging times, as it can provide opportunities to capture market share and offer value propositions that help customers save money. Founders transitioning to CEOs need to focus on communication, delegation, and defining their role in strategy, culture, and fundraising. It is essential for founders to align their goals and values with their business to make informed decisions and find fulfillment in their work. Coaching and mentorship can provide valuable guidance and support for founders navigating the challenges of entrepreneurship. Find Startup Hustle Everywhere: https://gigb.co/l/YEh5 This episode is sponsored by Full Scale: https://fullscale.io Visit the Startup System website: https://www.mystartupsystem.com Learn more about Vijay here: https://www.linkedin.com/in/vijayarajendran Sign up for the Startup Hustle newsletter: https://newsletter.startuphustle.xyz Titles The Value of Coaching and Mentorship for Founders Aligning Goals and Values for Informed Decision-Making Sound Bites "There are things that we can do for ourselves, for our companies, for the people around us that can help us get through what is an extremely difficult period." "If we're not in a market where companies are spending a lot of money and there's a lot of growth out there, it'd be hard to raise a lot of capital and think, hey, we're gonna grow, grow, grow, grow, because now that is not gonna happen." "Your answer lies in their success. So figuring out how to offer them a message of hope and survival is how you're going to improve and refine your value proposition." Chapters 00:00 Introduction and Overview 02:16 Startup Resilience and Economic Uncertainty 04:09 The Importance of Being Cashflow Positive 08:57 Adapting and Refining Value Propositions 12:25 Transitioning from Founder to CEO 27:37 Communication, Delegation, and Role Definition 32:58 Aligning Goals and Values 35:28 The Joy of Building and Creating 37:34 Contact Information and ConclusionSee omnystudio.com/listener for privacy information.

Aug 1, 2024 • 34min
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 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 challenges of transitioning from a founder to a leader and the importance of building a talented team. Dale provides insights into pricing strategies and the differences between selling to SMBs and enterprises. Takeaways Positioning is crucial for companies to focus on their target audience and effectively communicate their value proposition. Niche down and focus on a specific customer profile to make your marketing more relevant and effective. Transitioning from a founder to a leader requires delegation and building a talented team. Consider the size of the organization you're targeting when determining your pricing strategy. Selling to SMBs and enterprises requires different approaches and considerations. Find Startup Hustle Everywhere:https://gigb.co/l/YEh5This episode is sponsored by Full Scale:https://fullscale.io/Find out more about Njord & Co here:https://www.njordconsult.com/ Learn more about Dale Walden here:https://www.linkedin.com/in/dalewalden/ Sign up for the Startup Hustle newsletter:https://newsletter.startuphustle.xyz/ Sound Bites "Positioning is difficult to define, but you know it when you see it." "Make your pitch and proposition relevant to your customer's identity or aspirations." "Transitioning from a ruthless dictator mindset to a collaborative leader is crucial for scaling a business." Chapters 00:00 Introduction and Overview 03:01 Entrepreneurial Journey and Lessons Learned 05:30 Identifying Common Challenges in SaaS Businesses 08:18 Niche Down and Focus on Ideal Customer Profile 11:18 Creating Relevance and Emotional Connection with Customers 13:15 The Benefits of Focusing on a Local Market 14:13 Defining Good Positioning 15:30 Key Questions to Answer in Positioning 16:24 Differentiating Value and Making the Proposition Relevant 19:07 The Challenges of Psychological Positioning for Technical Founders 20:04 Quantifying Differentiated Value for Enterprise Customers 21:11 The Challenges of Unfair Advantage Perception 22:06 Transitioning from Founder to Leader 23:21 The Importance of Delegation and Collaboration 25:18 The Challenges of Letting Go of Control 27:20 The Importance of Talent and Building a Great Team 28:31 The Top Three Mistakes in Positioning 29:24 The Importance of Targeting the Right Market SizeSee omnystudio.com/listener for privacy information.

Jul 25, 2024 • 36min
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 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 recurring revenue and the value of building relationships with clients. Rich's podcast, Agents of Change, provides actionable tips for digital marketing. Takeaways - AI is transforming the field of digital marketing, increasing productivity and improving the quality of work.- Finding your uniqueness and niching down is essential for standing out in a crowded market.- The Remarkability Formula consists of four lenses: find, focus, frame, and forge, which help identify and leverage what makes a business remarkable.- Recurring revenue is crucial for the long-term success and value of a business.- Building relationships with clients is key to retaining them and creating a loyal customer base. Find Startup Hustle Everywhere:https://gigb.co/l/YEh5 This episode is sponsored by Full Scale:https://fullscale.io/ Visit the Flyte New Media website:http://www.takeflyte.com/ Check out Rich Brooks' podcast:https://www.theagentsofchange.com/podcasts Learn more about Rich Brooks here:https://www.linkedin.com/in/therichbrooks/ Sign up for the Startup Hustle newsletter:https://newsletter.startuphustle.xyz/ Sound Bites "It's so much easier to just talk and just ramble and use AI to help you continue and improve it.""You don't want to be competing with somebody else. You don't want to be competing on price.""Find things that are very difficult to replicate and that your customers care a lot about." Chapters 00:00 Introduction to Digital Marketing and AI02:53 The Remarkability Formula and Leveraging AI in Content Creation05:35 Transitioning to Recurring Revenue in Professional Services11:41 The Value of Hosting a Digital Marketing Conference See omnystudio.com/listener for privacy information.

Jul 18, 2024 • 41min
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 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 Microsoft to becoming a solution architect and eventually starting his own company. They also delve into the unique problem that Edge Delta solves, which is processing and analyzing data at the edge to determine its value and optimize storage and retention. Takeaways- Observability is crucial for managing large amounts of data in complex production environments.- Developers need access to production data without compromising security.- Edge Delta solves the problem of processing and analyzing data at the edge to determine its value and optimize storage and retention.- The company provides flexible and scalable solutions for observability and data pipelines.- Edge Delta competes with log management tools like Splunk and DataDog, offering 80% of features that customers care about.- Edge Delta aims to be the best platform for customers in the long term, rather than focusing solely on revenue. Starting a deep tech and enterprise company requires a long-term vision and the ability to navigate both technical and sales challenges.- Raising early-stage funding can be lengthy, but having a strong team and unique insights can help attract investors.- The sales cycle for enterprise accounts is typically five to six months, involving multiple teams and evaluation periods.- Storing and analyzing large amounts of data in the observability space is a significant challenge, and implementing next-generation architectures can help bring down costs.- Entrepreneurs should seize the current market opportunities and the availability of talent and potential investors to pursue their dreams. Find Startup Hustle Everywhere:https://gigb.co/l/YEh5 This episode is sponsored by Full Scale:https://fullscale.io/ Visit the Edge Delta website:https://edgedelta.com/ Learn more about Ozan here:https://www.linkedin.com/in/ozanu/ Sign up for the Startup Hustle newsletter:https://newsletter.startuphustle.xyz/ Sound Bites"I'm excited because not very often do I get a podcast host who also has a tremendous amount of experience in the space.""I think my unique experience of being an ex-developer who then went solution architect and went salesperson, showing up once a week and really working with the customers on deep technical challenges, kind of in the front trenches, that...""Edge Delta is the concept of how do we start looking at data as it's being created, as close to the source of that data as possible, and how do we start to pre-process, pre-aggregate, and frankly have machine learning and some even basic AI running on the edge.""We have to have a very long-term vision on this, even on day one.""The team is probably the number one thing.""It feels like you're on the treadmill, just trying to get a few customers landed." Chapters00:00 The Challenges of Observability and Data Management06:17 Solving Unique Problems with Edge Delta12:55 Competing in the Landscape of Observability Vendors25:05 The Journey to Acquiring the First Paying Customer31:22 Innovation in the Observability SpaceSee omnystudio.com/listener for privacy information.

Jul 11, 2024 • 36min
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 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 highlights the importance of certifications and government contracts in growing her business. Neelima offers tips for entrepreneurs, including the value of networking and persistence.Takeaways- Snap IT was founded to address the lack of affordable and skilled engineers in Kansas City.- The company started as a training company but evolved into an IT solutions provider.- Retaining talent is a challenge in the IT industry, especially for small businesses.- AI is changing software development and the skills required in the industry.- Government contracts and certifications have been instrumental in the growth of Snap IT.- Networking and persistence are key for entrepreneurs. Find Startup Hustle Everywhere: https://gigb.co/l/YEh5 This episode is sponsored by Full Scale: https://fullscale.io Visit the SnapIT Solutions website: https://snapit.solutions Learn more about Neelima here: https://www.linkedin.com/in/neelimaparasker Sign up for the Startup Hustle newsletter: https://newsletter.startuphustle.xyz Sound Bites:"I wanted to hire talent, which is affordable.""Everybody's a free agent, right?""We keep them in Snap IT for about three to four months till they become independent."Chapters:00:00 The Launch of Snap IT06:36 How to deal with employees who leave10:28 How to make opportunities for your future workforce17:01 How AI is changing software development22:31 Working with a significant other in the IT business24:52 The real deal in getting government contracts29:10 Neelima's journey in creating a software company33:00 Tips for Entrepreneurs See omnystudio.com/listener for privacy information.

Jul 4, 2024 • 32min
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 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 entrepreneurship, and it's important to align urgency with partners and customers to drive progress. Finding opportunities often involves recognizing the cracks in closed doors and actively pushing them open to create new possibilities. Practical advice and templates provided in Maria Flynn's book 'Make Opportunity Happen' offer valuable insights for entrepreneurs, covering topics such as decision-making, rapid discovery, and hiring. Follow-up and persistence are essential in sales and business development, and having a routine for follow-up can lead to successful outcomes. Momentum is key in business and entrepreneurship, and taking small steps can lead to significant progress over time. Find Startup Hustle Everywhere: https://gigb.co/l/YEh5 This episode is sponsored by Full Scale: https://fullscale.io/ Visit the Ambiologix website: https://ambiologix.com/ Check out Maria Flynn's book here: https://makeopportunityhappen.com/ Learn more about Maria Flynn: https://www.linkedin.com/in/mariasflynn/ Sign up for the Startup Hustle newsletter: https://newsletter.startuphustle.xyz/ Sound Bites "This is known to be the place to do animal health and similarly it should be the place to do digital health." "No, they can't sign a PDF file, guys. We need to send like a DocuSign or something like, why are we making it hard for them to sign the job offer? Like, it's all the little details like that that just add a lot of friction." "And if you don't feel like that, you should be doing something else." Chapters 00:00 Introduction and Background 03:02 The Role of Urgency in Entrepreneurship 06:07 Finding Opportunities and Pushing Open Closed Doors 11:52 Practical Advice for Business Success 24:48 The Power of Momentum in BusinessSee omnystudio.com/listener for privacy information.

Jun 27, 2024 • 33min
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 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 (hint: it's not all about Vikings!) How to scale down to scale up - practical strategies for conquering the European market, one country at a time. The secrets to mastering the art of billing and pricing for SaaS companies, from navigating cultural communication styles to mastering B2B complexities. Why focusing on a laser-sharp Ideal Customer Profile (ICP) is the key to unlocking explosive growth. Get ready to unlock valuable insights on everything from navigating regulations to cultural nuances, and discover how to build a thriving SaaS business on the European stage! Find Startup Hustle Everywhere: https://gigb.co/l/YEh5 This episode is sponsored by Full Scale: https://fullscale.io/ Visit the Younium website: https://www.younium.com/ Learn more about Niclas Lilja: https://www.linkedin.com/in/niclas-lilja/ Sign up for the Startup Hustle newsletter: https://newsletter.startuphustle.xyz/ Highlighted Discussion Points Starting a SaaS company in Sweden, with insights on the market and regulatory challenges. 0:31 Scaling down target markets and expanding internationally, with insights on business culture and communication differences between the US and Europe. 5:24 Billing and pricing strategies for software companies. 12:47 Billing and revenue recognition for SaaS companies, with emphasis on the importance of accurate data and staying focused on ICP. 18:56 Billing and pricing strategies for SaaS companies. 22:51 Pricing strategies for enterprise software companies. 28:39 See omnystudio.com/listener for privacy information.

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
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