Ashley Cooper on Lovable, Local-First AI Apps, and Safe Agent Workflows for MSPs

The host interviews Ashley Cooper (COO at Cyber Drain, VP of Community at Rewst) about her use of Lovable and other AI coding tools to build small, local-first, deterministic apps and learn through prompting. Ashley describes receiving a Lovable contributor gift after ranking in the top 0.01% of users, her early failed attempt to rebuild community software, and her shift to rapid, browser-based prototypes like JSON-to-CSV converters, receipt/expense and food trackers, and a webhook-driven PSA time-entry timer. She explains her workflow moving from Lovable scaffolding to GitHub/VS Code with Copilot, plus experimenting with Bolt and tools like OpenClaw, emphasizing trust boundaries, least privilege, and treating agents like employees. They discuss prompt engineering using philosophical mental models, risks of unvetted "vibe-coded" SaaS, and advising MSPs to start with data readiness and education before deploying AI for clients.

This episode is brought to you by Opsleader Pro. A place for MSP owners and managers to get the systems and tools they need to build a stable and growing MSP. Part group coaching, part peer group, everything you need to run a successful MSP.

00:00 Meet Ashley Cooper

01:17 Lovable Gift Surprise

03:01 Early Builds and Lessons

05:25 Hackathon One Shot Apps

09:34 Finding Ideas to Build

11:00 Viral AI Side Projects

14:09 Keeping or Killing Projects

18:22 Local First Automation Wins

19:51 Beyond Lovable Toolchain

24:03 OpenClaw Risks and Power

30:49 AI As Employee

31:18 Stress And Bias

32:02 Context Anxiety

34:52 Prompt Writing Workflow

37:23 Mental Model Prompts

41:44 Deep Instruction Sources

47:20 SaaS Apocalypse Debate

49:53 MSP AI Readiness

53:47 Education And Governance

56:30 Closing Thoughts

Ever wonder what really happens behind the scenes when a rocket-ship MSP vendor goes from scrappy startup to multi-billion dollar public company? Today, I'm talking with Michael Fass, former Datto general counsel and now CEO at Slide. Michael's seen the vendor/MSP relationship from every angle—legal, operational, and now as a co-founder, building Slide for the MSP channel.

If you want a brutally honest look at what hypergrowth actually looks like from the inside, why most MSPs never get past "just technical," and how to avoid being the cobbler with ragged shoes, this episode is for you.

You'll walk away knowing how to spot your "butter zone" in leadership, and a new way to think about partnering with the tech vendors in your stack.

This episode is brought to you by Opsleader Pro. A place for MSP owners and managers to get the systems and tools they need to build a stable and growing MSP. Part group coaching, part peer group, everything you need to run a successful MSP.

Today I'm excited to bring you a really insightful conversation with Brian Largent. Brian brings nearly two decades of experience running an MSP that specializes in co-managed IT services, particularly in complex and regulated industries like healthcare and manufacturing.

In this episode, Brian and I get into the nitty-gritty of co-managed IT. What it means, why it's not just for large enterprises, and how his team lives and breathes this model for clients, unexpectedly in rural markets. 

We dive into the real challenges and opportunities of working alongside internal IT teams, what makes for a successful partnership, and some lessons learned from both our journeys in the MSP space.

Whether you're an MSP looking to branch into co-managed services or looking to improve your co-managed offering, you'll get a ton of actionable insights from this conversation.

This episode is brought to you by Opsleader Pro. A place for MSP owners and managers to get the systems and tools they need to build a stable and growing MSP. Part group coaching, part peer group, everything you need to run a successful MSP.

On the podcast today I'm speaking with Canon Bryan, CFO with Terrestrial Energy. Terrestrial Energy is an industry leader in next-generation nuclear energy. Nuclear is a fantastically efficient and clean source of energy, but over the years it's earned a bit of negative reputation. As Canon and I discuss this reputation is really unfair when you examine the facts. Terrestrial Energy is building the next generation of nuclear power. It's much more compact, it's dramatically safer, and could be the key to our energy future.

Resources mentioned

4th Generation Energy Blog

Terrestrial Energy on Twitter & Facebook

Taylor Wilson - MSR Ted Talk - This is the TED Talk that got me excited about the MSR technology

Turning CO2 into gasoline

Nuclear facilities have killed far fewer people than you may think.

Today on the podcast, my guest is Nigel Moore, Founder of The Tech Tribe.

Nigel built and sold a successful MSP in Sydney. He now is leading a tribe of MSP owners looking to grow their MSP practice.

Nigel and I talk about the evolution of the IT service company to an MSP.

The mistakes people make and what makes it difficult. We also explore the idea of if you should do TnM & MSP or just go pure MSP.

Nigel is a fantastic guy and is truly passionate about the industry.

Managed Services in a Month - by Karl Palachuk

The Tech Tribe discount link here. Use this link and get 40% off your first month and the tech tribe will donate mosquito nets to communities in Africa!

Today's podcast is brought to you by Simplesat. Your tool for stupidly simple satisfaction surveys. I'm joined by Derek and Cory Brown, the father-son team behind Pronto Marketing and Simplesat.

If you're in a service-based industry it's important to know how your customers feel about your service. Traditional satisfaction surveys are terrible and the response rate shows that's the case. Simplesat can increase your client feedback 10 fold. Simplesat also makes the data more actionable. Jump over to simplesat.io for a free 30-day trial and try it out yourself.

Today on Evolved Radio we're talking everyone's favorite IT topic lately. Security!

I'm joined by Ian Paterson CEO of Plurilock. His company has a really innovative approach to security. It's an advanced form of user identification that can tell who you are by how you type and move the mouse.

We talk about why users hate passwords, security requirements for regulated industries, and much more.

Richard Tubb is one of the best-known experts in the global IT Managed Service Provider (MSP) community. His track record speaks for itself, as he launched and sold his own MSP business before creating a leading MSP media and consultancy practice. Richard is also the author of the IT Business Owner's Survival Guide and the author of the Tubblog.

We discuss why you may need a business coach, what business owners tend to struggle with most, and how technology is evolving MSP businesses as well as their client's businesses.

Several books are mentioned in the podcast in addition to Richard's book.

The E-Myth revisited

Getting Things Done

On the podcast today, I'm chatting with Alex Markov, President of Red Key Solutions and CEO of Strategy Overview.

Red Key is a mature and successful MSP in the New York area. Alex and his team work hard to deliver business value to their clients. One of the best way for MSPs to do that is implementing a QBR/TBR. Alex recognized the value in the system they had built and has created a SaaS product called Strategy Overview to help others deliver effective technology planning to their clients.

Dan Sutton is vocal leader in the BC cannabis industry. Dan started Tantalus Labs, a cannabis production company in 2012. Dan has been a strong supporter of greenhouse based production of cannabis. We talk about the social and financial impact of that approach. We also discuss the fast dissolving social and professional stigmas associated with cannabis. Canada is expected to federally legalize cannabis in 2018. The Canadian market alone is expected to be worth about seven Billion. Dan and his team hope to position sungrown BC bud as a market leader in the industry.

If you've never heard of Graphene, you can bet you'll be hearing a lot more about it in the coming years.

Graphene is a material that quietly holds the keys to many of our next generation of technological advances. Filtering water at an atomic level, creating impossibly lightweight bulletproof material, building a quantum supercomputer, and powering nanobots. This little-known material called Graphene is central to a series of fascinating technical discoveries.

Today I'm speaking with Dr. Joseph Meany. Dr. Meany is and his colleague, Les Johnson, have written a book about this amazing material.

Wim Kerkhoff and I talk lean for devops and IT managed services. Wim built a Kanban system for Connectwise Manage

James built an offshore support team to augment his MSP business. He found the offshore strategy enabled a scaling of his business that he otherwise never could have achieved. As more and more peers asked him how to do the same he recognized a business opportunity and Benchmark 365 was born. James and I discuss his journey, some of the common resistance points around offshoring and how his team integrates with existing MSP businesses.

Welcome back to the Evolved Radio Podcast! In today's episode, I'm joined by Anup Ghosh with Threatmate. Anup and I deep dive into one of the MSP industry's hottest—and sometimes most confusing—topics: cybersecurity. But instead of focusing on the aftermath of a security incident (what they call "right of the boom"), we shift the conversation to proactive measures—what it really means to operate "left of the boom."

We unpack the concept of security as a utility, discuss how to utilize NIST and CIS frameworks, and explore fear-based selling.

This episode is packed with insights that will help you strengthen your security posture before disaster strikes. So listen in to stay ahead of the next big threat.

This episode is brought to you by Opsleader Pro. A place for MSP owners and managers to get the systems and tools they need to build a stable and growing MSP. Part group coaching, part peer group, everything you need to run a successful MSP.

Ted is the Chief Revenue Officer at Itopia. Itopia's mission is to make it easy to migrate Windows workspace environments to the cloud.We talk about the evolution of Cloud computing, including Desktop as a Service (DaaS) and using the public cloud for rapidly deploying computing infrastructure. This is a rapidly growing solution in the IT industry enabling providers to spin up remote desktop environments in no time at all. Ted and I also talk about the competition between AWS, Azure, and Google in the public cloud arena.

Tim Kane is co-founder and CEO of myHSA. myHSA is a technology company that facilitates Insurance brokers with the ability to offer in-house health spending accounts. In my interview with Tim, we explore his evolution from brick and mortar business owner to digital entrepreneur. His journey has been filled with hard lessons about building a software business as a non-technical founder. His passion, determination, and strong focus on customer service have served him well. Tim and his co-founder Steve have grown the company from two people and a database to 8+ staff and a fast growing client base. 

You have probably heard the term Big Data. What does that mean anyway? Today I'm joined by Alastair Woolcock, to talk about Data Science. We uncover the science of data analytics and how data is unlocking market changing insights at all levels of business. Whether you're a small business trying to understand social media and it's influence on your marketing efforts, or an enterprise organization trying to understand client behavior, data can be a powerful tool. There is a growing industry of data science that is trying to use the power of hypothesis to mine for insights in the mountains of data that our modern businesses produce. 

Today's podcast I'm joined by Raj Goel, CISSP. Raj is the founder of Brainlink and the creator of SOP Culture. Raj and I explore the benefits and the challenges of creating a SOP driven culture in your business. SOP Culture was formed out of years of Raj standardizing his teams work at Brainlink to ensure a consistency of service that gives him an unusual competitive edge in the market.

Dr. Ray Hsu and I discuss how higher education needs to evolve to best serve students and innovation.

Dr. Ray Hsu Professor at UBC. He is both the founder of the VR/AR  working group and faculty in residence at the emerging media lab, conducting research on the immersive technology. When most people think of VR they think of video games. Like many of us, Dr.Ray sees the value of VR in the gaming field, but his vision for its impact go far beyond that. In particular, I wanted to talk to Dr.Ray about his view on how VR/AR will influence education.

My guest today is Miguel Sanchez with Mass Ideation. I think that augmented reality and mixed reality are going to have a massive influence on how brands market their ideas and products. Why simply have a glossy photo with some cool print, when you can have a mini-movie built into your advertisement. Miguel's company is leading the way in the industry helping companies use leading-edge technologies to create a more memorable and engaging experience in their marketing work. This market is evolving fast with all the big names getting behind AR after the success of Pokemon GO. I hope you enjoy my conversation with Miguel.

My guest today is Bill Stucklen, CEO of Stack Advisors. Bill and I discuss a specific portion of the Managed IT space. Stack Advisors is a company that provides expertise to MSPs using Labtech and Connectwise. The reason I was interested in having Bill on to chat was that it seems counter-intuitive that an IT company would outsource its internal systems management to a third party, but it makes a ton of sense for many MSPs.

Welcome back to another episdoe of the Evolved Radio Podcast! In this episode, I'm joined by Peter Melby and Ryan Barton with New Charter Technologies. 

Sure, AI is everywhere these days, but we cut through the hype to talk about how things actually changed when ChatGPT hit the scene and suddenly put powerful AI tools in the hands of everyone.

Ryan shares how that breakthrough moment inspired him to roll up his sleeves and experiment with AI in real business scenarios.

Peter talks about why New Charter decided to take a hands-on approach with AI, instead of just waiting around for vendors to figure it out.

We talk honestly about what's working, what isn't, and why sometimes you just have to make your own path with new technology.

If you want an inside look at how AI is impacting MSPs or you're just curious about what's really possible right now, tune in!

We've got practical insights, plenty of candid takes, and even a few laughs along the way.

This episode is brought to you by Opsleader Pro. A place for MSP owners and managers to get the systems and tools they need to build a stable and growing MSP. Part group coaching, part peer group, everything you need to run a successful MSP.

New threats are emerging on the internet. Just in recent months we have seen shockingly more mature attacks on the internet. State sponsored cyberwar tactics are being brought in to the public eye. Last month we saw one of the largest DDoS attacks ever recorded. So I wanted to chat with a friend of mine that has deep roots in the Internet Security industry and get his thoughts on the rapid evolution of the security industry.

Rob Malec is an author, consultant, active keynote speaker to the business community and business columnist. He is the President of Businessworks Consulting Inc. Based in Vancouver British Columbia he has been helping his clients increase the revenue their company's generate while operating more effectively as an organization since 2001.

Continuum has a strong and diverse marketing approach that is geared toward the digital age.  Some of the topics we cover are social media, content marketing, and how to noticed amid the noise of the internet. This episode will give you some actionable advice on how to mature your digital marketing strategy to drive your success.

Vancouver is often talked about as future tech hub. Already big companies like Microsoft & Amazon are expanding their presence in Vancouver. I reached out to our guest today to chat about the expanding tech sector in Vancouver. We discuss some of the opportunities and challenges with this growing sector of our local economy and how it fits into the global tech market.

Tyler Orton is a reporter at Business In Vancouver newspaper who specializes in B.C.'s tech sector.

He also hosts BIV's daily show on Roundhouse Radio 98.3, tackling headline news and interviewing the city's most notable names in business.

Kevin Crowe is the founder of Give A Mile. Give A Mile is a 'not for profit' online platform that enables people to visit a palliative ill loved one or people with a life threatening illness through crowdfunding of flights via donations of travel loyalty miles. Kevin was inspired to start Give A Mile after losing a very close friend to brain cancer.  Kevin is also a member of the leadership team of Long View Systems a technology company.  As a member of the Long View leadership team he has helped take the company from 11 people to over 1,100 people working across North America.  Kevin also loves to pursue endurance sports having completed several ultra-marathons including the Canadian Death race and the Ironman.  He currently lives in Calgary with his amazing wife and awesome son.

Alex is a cyber security expert professionally but also has a deep passion for drone technology. His passion led him through a hobby interest in flying drones, to building and racing drones. He now helps organize a regional drone racing league in Vancouver. In the conversation, we chat about the growing sport of drone racing, some of the safety concerns around drones, the development of flying AI, and a few of the numerous commercial applications for drone tech. Lots of people are familiar with drone tech, but few appreciate how dramatically this tech will weave its way into our daily lives. 

Robert Merki is Director of Product at CognitiveVR. He started exploring web development at the age of 10 and continued building technology products all throughout his youth. After working at a variety of technology startups, Robert joined cognitiveVR to head up product development. CognitiveVR is a virtual reality analytics company based out of Vancouver BC. The company's analytics platform helps their customers overcome the complexity of VR to bring them deep insights into how their users are interacting with their products. With the advent of VR, analytics becomes a vital way VR experience creators hone and optimize their narratives, games, and tools.

Rachel is a consultant and trainer to project managers, freelancers, and creative teams. She is also an active leader in the Digital Project Manager community in Vancouver, BC. This episode is a lot of fun, Rachel and I talk about the evolving history of project management and it's increasing role in the digital economy. Then we go down a few fun rabbit holes about finding a higher purpose, machine learning, AI, and other futurist topics.

David reviews with us his eco-system for a healthy culture and we chat about the evolution of corporate culture through the years. We also touch on some of the key struggles that business owners deal with when trying to develop a healthy culture.

Kevin is a Microsoft MVP specializing in App-V and application delivery technologies. We chat about the MVP program, App-V itself and its evolution from Softgrid. We also touch on application delivery options for IT shops and MSPs. Then we look forward to the future of application delivery, how Azure will play a role and industry adoption of cloud infrastructure.

Today on the Evolved Radio Podcast, I'm joined by Paul Green,  the author of "MSP Marketing Start Here," for a deep dive into the world of LinkedIn social marketing. This episode is perfect for MSPs looking to streamline their marketing efforts. Paul shares insights from his book, emphasizing the importance of simplifying marketing strategies and focusing on building long-term relationships through platforms like LinkedIn. He discusses practical steps like creating engaging content, leveraging LinkedIn's unique tools and features, and the power of setting up reliable marketing systems. Todd and Paul also explore the importance of connecting with ideal clients, the impact of video content, and why consistency is key to achieving success in the competitive MSP ecosystem. Use the insights to discover actionable tips that can transform your LinkedIn presence and take your marketing to the next level.

Also there is a time limited ester egg at the end of the pod, so listen early and stick around till the end for that bonus.

This episode is brought to you by Opsleader Pro. A place for MSP owners and managers to get the systems and tools they need to build a stable and growing MSP. Part group coaching, part peer group, everything you need to run a successful MSP.

Vanbex is a group that specializes in strategy, marketing, and operations consulting for blockchain companies. Lisa has a relatively long history with blockchain tech having worked with companies like Mastercoin, Ethereum, Factom, and Tendermint. Lisa is a strong believer in the future of the blockchain and its power to evolve countless aspects of not just finance, but all businesses. We chat about the politics of bitcoin, the fast evolution of the blockchain markets, and hurdles still in place before the mainstream adoption of blockchain currencies.

Luis Giraldo is the Founder and CEO of Ook Enterprises, a Managed IT service provider focusing on the small business space in Vancouver. Luis and I explore the what and the why of managed services for businesses. As well as, some of the trends we see in the partnering and sales process for managed service business owners as well as companies looking to outsource their IT to a partner.

Marc Stoiber is on a mission to make speeches and presentations interesting and engaging. Marc has a rich history in advertising and has won numerous awards for his work with all sorts of brands including local brands as well as huge multi-national ones. We talk about the evolution of marketing and advertising in the digital age and why TED-style speeches have become such a pop-culture phenomenon.

Alex Sterk is passionate about all things blockchain. For the past year, Alex has been interviewing members of the blockchain and fintech space on his podcast Blocktalk. Alex and I talk about the power of the blockchain, some of the cool projects he's come across in his interviews and what the future may hold for this technology.

Jessie Adcock brought her deep experience in enterprise organizations to government. The City of Vancouver has a vision for a digital strategy. Jessie is responsible for the development and implementation of that strategy. We explore the evolution of government and technology, how the city of Vancouver is supporting their digital economy and the city's open data initiative.

Interview with Lachlan Turner of Arkinfosec (@ArkInfosec). We discuss the current state of cybersecurity. What hack attacks look like and how the hacker conducts the attacks. How can people and businesses protect themselves? What does the future hold for cyber security?

Some portions of the audio have a slight echo. I'm quickly learning how to properly engineer the audio for future episodes.

Welcome to another insightful episode of the Evolved Radio Podcast! Today, we dig into the timeless wisdom of "The 7 Habits of Highly Effective People." with Andrea Caldwell, VP of Coaching and consulting at Franklin Covey. Celebrating the book's 35th anniversary, Andrea sheds light on why Stephen Covey's principles have stood the test of time, attributing their longevity to the foundational truths they encapsulate. We explore how these habits have shaped our personal and professional lives, emphasizing the significance of paradigms, proactive behavior, and continuous self-renewal.

Whether you're familiar with Covey's work or new to these concepts, this episode promises to offer valuable insights into creating a more intentional and effective life. So let's go!

This episode is brought to you by Evolved Management Training Courses.

Online courses specifically crafted for MSP needs. A Service Manager BootCamp course, a project manager for MSPs course, an MSP Account Management course course, and an IT Documentation Done Right course.

In this episode of the Evolved Radio Podcast, I'm joined by Alex Markov from Strategy Overview. Alex and I continue the rethinking vCIO series. 

Alex is a long-time friend of the podcast, appearing in a very early episode of the pod (ERP031). 

I had him back to jam on vCIO again. We explore the importance of mature VCIO practices, the integration of AI and automation, and maintaining high standards in client services. 

Enjoy the continued conversation in rethinking the vCIO series.

Today on the Evolved Radio Podcast, we continue our series on Rethinking the vCIO role in MSPs. I'm joined by Jim Tarala from VCIO University to discuss the challenges and opportunities of the vCIO role. We'll explore the importance of role clarity, client segmentation, and tips for distinguishing between account managers and vCIOs. Jim shares valuable insights into the need for a strategic approach when targeting different client segments and how MSPs can create value with vCIO services. Listen for more actionable strategies to refine your client interactions and elevate the services you provide.

This episode is brought to you by Evolved Management Training Courses.

Check out my latest course! MSP Account Management.

On this episode of Evolved Radio, we're continuing our rethinking vCIO series with Adam Walter from Humanize IT. Adam helps give a fresh perspective. Adam has years of experience as a director of security and as a vCIO in the corporate world. He has great insight on what it's like sitting on the other side of the table from a typical MSP. 

In this episode, Adam shares a compelling story from his career, highlighting the crucial role of curiosity in client interactions.

Whether you're an MSP owner, a vCIO, or someone looking to enhance client relationships, this episode is packed with valuable insights and practical advice to help you rethink your vCIO strategy.

This episode is brought to you by Evolved Management Training Courses.

Check out my latest course! MSP Account Management.

In today's episode, I'm joined by Alex Farling from Empath. In the last episode, Luis Giraldo and I were talking about vCIO. Alex was listening to the episode and took up my challenge to fight us in the comments. Alex has lots of opinions and experience in the vCIO field, having built one of the leading platforms for vCIO out there. Interestingly, even Alex says he hates the term vCIO and explains why. We also discuss "firing" clients, the critical role of communication in maintaining positive relationships, agendas, and the nuanced roles required in smaller MSPs.

This is another episode packed with insights and on the role of account management in the MSP space. So get ready to rethink the vCIO role again with us on the Evolved Radio Podcast!

This episode is brought to you by Evolved Management Training Courses.

Check out my brand new course - vCIO and Account Management for MSPs

Or my other online courses specifically crafted for MSP needs. A Service Manager BootCamp course, a project manager for MSPs course, an MSP security fundamentals course, and an IT Documentation Done Right course.

Today, I'm chatting with my old friend Luis Giraldo, Chief Experience Officer at Scalepad. Luis and I are discussing how most of our industry might be doing vCIO all wrong.

vCIO has the Critical Objective of creating real client value by delivering services that lead to genuine business outcomes, but many struggle to make this a reality.

We discuss why people hate the vCIO title and ideas about what we should call it instead.

We discuss some common pitfalls, like focusing too much on tools over processes.

Whether you're trying to start or improve your vCIO process, this episode is a must-listen. So let's go.

This episode is brought to you by Evolved Management Training Courses.

Online courses specifically crafted for MSP needs. A Service Manager BootCamp course, a project manager for MSPs course, an MSP security fundamentals course, and an IT Documentation Done Right course.

Today, we have a unique perspective on AI, courtesy of our guest, Jeff Gaines with Treeline.ai.

In this episode, we're exploring what it truly means to be "AI-first" in the MSP space—not just adding AI as a feature, but building it into every layer of the operation for a fundamentally different approach to service delivery.

If you've been following the rapid changes in software, automation, and managed services, you won't want to miss this episode. We're getting into operational strategy, technology adoption, and the future of MSPs in the age of AI.

This episode is brought to you by Opsleader Pro. A place for MSP owners and managers to get the systems and tools they need to build a stable and growing MSP. Part group coaching, part peer group, everything you need to run a successful MSP.

Welcome to another episode of Evolved Radio Podcast! Today, we're talking Sales strategies and tactics with my guest, Megan Killion, chief consultant with MKC Agency.

We start off by discussing finding strength in adversity. Megan shares her story about an incredibly challenging period in her life and what she learned. This was an unexpected rabbit hole we went down, but it's relevant since business development means getting a lot of "No"s, which can be so uncomfortable for people that they never start.

Then Megan shares practical tactics on qualifying leads, understanding client needs, and framing discussions to turn prospects into customers. This episode is packed with useful tactics that you can use immediately to grow your business. So let's go.

This episode is brought to you by Evolved Management Training Courses.

Online courses specifically crafted for MSP needs. A Service Manager BootCamp course, a project manager for MSPs course, an MSP security fundamentals course, and an IT Documentation Done Right course.