Most founders think investors bet on ideas. They don't.

Dave Lambert has funded over 2,000 companies through RightSide Capital, and he's seen this pattern play out thousands of times. Great product. No revenue traction. Wrong ask, wrong timing. Automatic no.

In this episode of Startup Hustle, Matt sits down with Dave to break down how RightSide Capital evaluates startups differently than traditional VCs. No subjective analysis. No months of diligence. Just data, profiles, and a decision in about a week.

They get into how AI is changing the startup game, not just for building products faster, but for every operational aspect of running an early-stage company. And why sales is still the one thing that isn't getting easier anytime soon.

Plus, the real talk on founder-market fit, why being slightly delusional might actually help, and what it takes to walk away with a check from an investor who's seen everything.

If you're a technical founder who knows how to build but has no idea how to sell, this episode is for you.

⏱️ Episode Breakdown

00:26 Introduction to Venture Capital and Startups

03:36 The Importance of Sales and Marketing in Startups

06:24 Data-Driven Investment Strategies

09:23 The Impact of AI on Startup Opportunities

12:23 Operational Efficiency and Cost Reduction through AI

15:28 Sales and Marketing Challenges for Startups

18:31 Support and Resources for Portfolio Companies

21:25 Evaluating Founders and Market Fit

24:28 The Role of Delusion in Entrepreneurship

Links & Resources

Connect with Dave Lambert on LinkedIn

What Smart CTOs Are Doing Differently With Offshore Teams in 2025

Subscribe to the Global Talent Sprint

Full Scale – Build your dev team quickly and affordably

If you’re trying to get your team out of the basement and into real product ownership, this episode is your playbook. Stop being a ticket factory. Build teams that think, create, and lead.

Follow the show, rate it, and send this to someone who’s still trying to do “real Scrum.” They need it more than you do.

Right Side Capital Management - https://www.rightsidecapital.com/

Matt Watson sits down with Mohan Reddy, serial entrepreneur and Chief Scientist at Cornerstone AI Labs, to explore how AI is fundamentally reshaping the way we think about work, skills, and human potential. Mohan shares the origin story of Skyhive—a workforce intelligence platform built to reskill and upskill people at a global scale—and how its acquisition by Cornerstone brought that mission to a larger stage.

The conversation digs into why AI doesn't eliminate skills but transforms them, the distinction between tasks that can be automated versus those that require human judgment, and why "vibe coding" is both a breakthrough and a danger. Mohan also makes the case for reverse engineering as the most critical skill in an AI-driven world, and why sandbox environments will be essential for building trust in AI-assisted workflows.

Whether you're a founder, engineer, or business leader trying to navigate the AI transition, this episode offers a grounded, optimistic perspective from someone who has spent decades at the intersection of human potential and machine intelligence.

If you enjoyed today's episode, subscribe to the Starter Hustle podcast and leave us a review!

⏱️ Episode Breakdown

00:30 The Journey of Mohan Reddy and Skyhive

03:34 Transition to Cornerstone AI Labs

06:22 AI's Impact on Skills and Workforce

09:33 The Evolution of Software Engineering

12:29 The Future of Coding and AI Collaboration

15:33 Upskilling in the Age of AI

18:30 Curiosity and Learning in Tech

21:34 Final Thoughts and Advice

Links & Resources

Connect with Mohan Reddy on LinkedIn

What Smart CTOs Are Doing Differently With Offshore Teams in 2025

Subscribe to the Global Talent Sprint

Full Scale – Build your dev team quickly and affordably

If you’re trying to get your team out of the basement and into real product ownership, this episode is your playbook. Stop being a ticket factory. Build teams that think, create, and lead.

Follow the show, rate it, and send this to someone who’s still trying to do “real Scrum.” They need it more than you do.

AI is changing how kids learn. But are schools ready?

Katie Boody Adorno is the founder and CEO of LeanLab Education. She's spent 13 years trying to close the opportunity gap in public education. In this episode, she and Matt break down how COVID widened learning disparities, why high-dosage tutoring works but doesn't scale, and how AI is now lowering that cost. They also get into what it takes to prepare kids for a world where AI handles most of the knowledge work.

Listen to the full episode now! Subscribe to Startup Hustle wherever you get your podcasts.

⏱️ Episode Breakdown

00:00 The Genesis of Lean Lab Education

05:25 Innovative Approaches to Educational Challenges

09:08 The Impact of the Pandemic on Education

11:32 Funding and Sustainability in Education

12:58 The Role of Technology in Learning

18:12 The Importance of Human Connection in Education

20:12 Rethinking the Purpose of Education

25:30 The Future of Higher Education and AI

Links & Resources

Connect with Katie Boody Adorno on LinkedIn

What Smart CTOs Are Doing Differently With Offshore Teams in 2025

Subscribe to the Global Talent Sprint

Full Scale – Build your dev team quickly and affordably

Lean Lab Education - https://leanlabeducation.org

Zach Klempf is back! He joined Matt Watson on one of the early episodes of the show. Now, Zach is president of AutoManager, a private equity group with five automotive software companies under its umbrella.

In this episode, Zach and Matt get into how AI is making senior engineers more productive. They talk about why offshore teams tend to adopt it more slowly, and where vibe coding breaks down when you're running production software with real integrations. They also get into why simple SaaS products are getting harder to defend. And why leads and sales have always been the harder problem anyway.

Listen to the full episode now! Subscribe to Startup Hustle wherever you get your podcasts.

⏱️ Episode Breakdown

00:00 Introduction to Zach Klempf and AutoManager

03:09 The Journey of Selle Automotive

05:48 Outsourcing and Global Talent Strategy

08:59 Experiences in Jamaica and the Philippines

12:01 Transition to AutoManager and AI Integration

15:13 AI Adoption and Team Dynamics

18:02 The Future of Software Development and AI

21:02 Challenges in AI Implementation

24:10 Market Dynamics and Competitive Landscape

26:53 Final Thoughts and Reflections

Links & Resources

Connect with Zach Klempf on LinkedIn

https://www.automanager.com/

What Smart CTOs Are Doing Differently With Offshore Teams in 2025

Subscribe to the Global Talent Sprint

Full Scale – Build your dev team quickly and affordably

If you’re trying to get your team out of the basement and into real product ownership, this episode is your playbook. Stop being a ticket factory. Build teams that think, create, and lead.

Follow the show, rate it, and send this to someone who’s still trying to do “real Scrum.” They need it more than you do.

In this episode, entrepreneur Chris Jones shares his journey from personal tragedy to building MatchRite Care, a healthcare data integration platform. He discusses product-market fit, scaling strategies, and the importance of community and continuous learning in entrepreneurship.

⏱️ Episode Breakdown

00:00 The Entrepreneurial Journey Begins

02:54 The Birth of MatchRite Care

06:07 Navigating Product Fit and Market Strategy

09:04 The Importance of Data Sharing in Healthcare

12:01 Scaling vs. Selling: The Business Model Dilemma

15:08 Consulting and Mentorship in the Entrepreneurial Space

17:45 The Value of Lifelong Learning and Community Support

20:48 Reflections on the Entrepreneurial Journey

Links & Resources

Connect with Chris Jones on LinkedIn

What Smart CTOs Are Doing Differently With Offshore Teams in 2025

Subscribe to the Global Talent Sprint

Full Scale – Build your dev team quickly and affordably

If you’re trying to get your team out of the basement and into real product ownership, this episode is your playbook. Stop being a ticket factory. Build teams that think, create, and lead.

Follow the show, rate it, and send this to someone who’s still trying to do “real Scrum.” They need it more than you do.

In this episode of Startup Hustle, Matt Watson interviews Mark Roberge, a former HubSpot executive and current venture capitalist, about his journey from engineering to sales and the importance of scaling startups. Mark discusses the genesis of HubSpot, the significance of sales in startups, and the concept of product-market fit. He emphasizes the need for customer research, avoiding false positives in feedback, and identifying the ideal customer profile. Mark also shares insights on scaling strategies, key metrics for success, and the science behind scaling businesses effectively.

⏱️ Episode Breakdown

00:00 The Genesis of HubSpot

02:56 Transitioning from Engineering to Sales

06:06 The Science of Scaling

08:53 The Importance of Selling Early

12:12 Understanding Customer Needs

14:58 Avoiding False Positives in Feedback

15:39 Design Partner Dilemma

18:21 Target Audience Insights

19:56 Ideal Customer Profile Framework

23:00 The Science of Scaling

25:05 Understanding Growth Investment

30:55 Navigating Growth Challenges

35:25 Final Thoughts on Scaling Success

TAKEAWAYS

Sales is crucial for startup success.

Understanding product-market fit is essential before scaling.

Customer research should start at the ideation stage.

Avoid false positives by validating customer interest.

Identify your ideal customer profile to focus efforts.

Scaling should be approached methodically and strategically.

Establish leading indicators of customer retention.

Sales methodologies must evolve as the company grows.

Demand generation must align with growth aspirations.

The science of scaling involves data-driven decision making.

Links & Resources

Connect with Mark Roberge on LinkedIn

What Smart CTOs Are Doing Differently With Offshore Teams in 2025

Subscribe to the Global Talent Sprint

Full Scale – Build your dev team quickly and affordably

If you’re trying to get your team out of the basement and into real product ownership, this episode is your playbook. Stop being a ticket factory. Build teams that think, create, and lead.

Follow the show, rate it, and send this to someone who’s still trying to do “real Scrum.” They need it more than you do.

In this episode of Startup Hustle, Matt Watson interviews Krishna Oza, founder and COO of Git Hired, discussing the challenges of hiring software engineers, particularly for startups. Krishna shares his personal experiences that led to the creation of GitHired, an AI-driven platform designed to help startups find the right technical talent based on proof of work. The conversation delves into the unique needs of early-stage developers, the importance of product thinking, and how GitHired identifies and surfaces 10x engineers. Krishna also discusses the business model of GitHired and the struggles faced by startup founders in finding suitable engineering talent.

TAKEAWAYS

Krishna's personal experience with hiring challenges inspired GitHired.

Startups need engineers who can match their fast-paced environment.

Early-stage developers are builders who understand product development.

Product thinking is crucial in today's AI-driven landscape.

10x engineers possess product vision and minimal organizational friction.

Get Hired surfaces hidden engineering talent through GitHub analysis.

The platform creates one-page portfolios for applicants based on their work.

Complexity of projects is a key factor in evaluating candidates.

The business model includes a flat fee for successful hires.

Startup founders often struggle to find engineers who can build for users.

⏱️ Episode Breakdown

00:00 The Genesis of GitHired

03:01 The Ideal Early Stage Developer

07:01 The Importance of Product Thinking

10:10 Identifying 10x Engineers

12:52 The Role of Proof of Work

20:09 Business Model and Market Fit

23:40 Startup Founder Struggles

Links & Resources

Connect with Krishna Oza on LinkedIn

What Smart CTOs Are Doing Differently With Offshore Teams in 2025

Subscribe to the Global Talent Sprint

Full Scale – Build your dev team quickly and affordably

If you’re trying to get your team out of the basement and into real product ownership, this episode is your playbook. Stop being a ticket factory. Build teams that think, create, and lead.

Follow the show, rate it, and send this to someone who’s still trying to do “real Scrum.” They need it more than you do.

In this episode of Startup Hustle, Matt Watson interviews John Morlan, founder and CEO of Smarter Risk, about the transformative impact of AI on startups. John shares his journey of integrating AI into his business, enhancing productivity, and improving collaboration with developers. He discusses the balance between product-led and sales-led growth strategies, the importance of knowledge management, and the challenges of achieving product-market fit. The conversation emphasizes the necessity of hands-on involvement from founders and the evolving role of AI in business operations.

⏱️ Episode Breakdown

00:00 Introduction to AI in Startups

00:57 John's Journey with AI

04:58 Prototyping and Development with AI

09:47 Balancing Coding and Leadership

15:03 Sales vs. Product-Led Growth

19:51 Building a Knowledge Base with AI

24:57 Final Thoughts on AI and Productivity

Links & Resources

Connect with John Morlan on LinkedIn

What Smart CTOs Are Doing Differently With Offshore Teams in 2025

Subscribe to the Global Talent Sprint

Full Scale – Build your dev team quickly and affordably

If you’re trying to get your team out of the basement and into real product ownership, this episode is your playbook. Stop being a ticket factory. Build teams that think, create, and lead.

Follow the show, rate it, and send this to someone who’s still trying to do “real Scrum.” They need it more than you do.

In this episode, Matt Watson interviews Matt Haycox, an experienced entrepreneur who shares insights from his 25 years in business, focusing on capital raising, the challenges of entering the tech space as a non-technical leader, and the impact of AI on business development. Haycox discusses his journey from traditional businesses to tech ventures, emphasizing the importance of understanding both technical and commercial aspects of business. He also highlights the value of learning from mistakes and building trust within teams.

Chapters

00:00 Introduction to Matt Haycox

02:52 Matt's Entrepreneurial Journey

05:46 Transitioning into Tech and SaaS

09:00 The Role of AI in Business Development

11:55 Understanding the Micro-SaaS Landscape

15:08 The Importance of a Good CTO

18:03 Learning from Mistakes in Business

21:05 Conclusion and Resources

Links & Resources

Connect with Matt Haycox on LinkedIn

What Smart CTOs Are Doing Differently With Offshore Teams in 2025

Subscribe to the Global Talent Sprint

Full Scale – Build your dev team quickly and affordably

If you’re trying to get your team out of the basement and into real product ownership, this episode is your playbook. Stop being a ticket factory. Build teams that think, create, and lead.

Follow the show, rate it, and send this to someone who’s still trying to do “real Scrum.” They need it more than you do.

What happens when you mix creative agency chaos with world-class engineering? You get teams that don’t just write code—they own the product.

In this episode, I’m talking with David Mitchell, CTO at VML, one of the biggest creative agencies on the planet. With thousands of engineers and global clients like Wendy’s and United Airlines, David’s teams are building things that most devs only dream of—and doing it without getting buried in bureaucracy.

We break down what it really takes to foster creative engineering inside a massive org, how to keep engineers out of the ticket-taking trap, and how AI is reshaping what engineering leadership actually looks like.

If you lead teams and want to stop micromanaging, or if you're just tired of pretending Agile is still helping... this one’s for you.

⏱️ Episode Breakdown

[00:15] — What is a "creative engineer" and why don’t we have more of them?

[06:00] — Why software engineering should be creative work

[07:40] — The evolution of engineering: From basement coders to business thinkers

[11:20] — Ownership vs. ticket-taking: How VML trains teams to lead

[13:30] — Journey-Driven Development and the myth of “API-first”

[20:45] — Is AI changing how we build software—or just hyped?

[24:00] — Hackathons, prototyping, and the rise of “vibe engineering”

Links & Resources

Connect with David on LinkedIn

Product Driven - Get the Book

Subscribe to the Product Driven Newsletter

What Smart CTOs Are Doing Differently With Offshore Teams in 2025

Subscribe to the Global Talent Sprint

Full Scale – Build your dev team quickly and affordably

If you’re trying to get your team out of the basement and into real product ownership, this episode is your playbook. Stop being a ticket factory. Build teams that think, create, and lead.

Follow the show, rate it, and send this to someone who’s still trying to do “real Scrum.” They need it more than you do.

Engineering Clarity in the Age of AI: How Docs, Context, and Product Thinking Shape Better Software

Seth Rosenbauer is the founder of a tool that uses AI to help engineers create better documentation—and, more importantly, the right thing, faster.

But this conversation isn’t just about tooling.

It’s about how context is the new currency in engineering. Why your team’s ability to understand what to build and why is more critical than ever. And how AI is changing the shape of product communication, technical documentation, and engineering ownership.

Whether you lead a growing dev team or are trying to ship more with less, this one’s for you.

Key Discussion Points

Seth’s journey: From PM to founder to doc tool builder

Why traditional documentation fails engineers

The real cost of unclear requirements

What AI can (and can’t) fix in engineering communication

How better docs lead to better products

The problem with "done"—and how teams miss the last 10%

Building a culture of engineering ownership

Links & Resources

Connect with Seth Rosenbauer on LinkedIn

Joggr

Product Driven - Get the Book

Subscribe to the Product Driven Newsletter

What Smart CTOs Are Doing Differently With Offshore Teams in 2025

Subscribe to the Global Talent Sprint

Full Scale – Build your dev team quickly and affordably