A recap of some of the incredible wisdom shared by my array of guests on this last season of The First 10 Podcast

I asked Rob Walling, serial entrepreneur, investor, author, and host of the popular podcast ‘Startups for the Rest of Us’ , if I could reshare the audio from a Youtube video he posted entitled "Top 10 Avoidable Mistakes SaaS Startups Make with Rob Walling". When I saw this video, I knew I had to share it. Its short, and stuffed with classic (and not so classic) pitfalls to avoid when building your SaaS.

Joining me to wrap up this serial-entrepreneur season is founder and chief side hustler of Side Hustle Nation, Nick Loper.

Have you ever had the itch to get a side hustle going!? If so, you will love this episode! If you have ever researched how to start your own side business, chances are high that you’ve come across Nick’s go-to website, www.sidehustlenation.com. Through his website and books, Nick guides start-up and seasoned entrepreneurs from all corners of the globe to make extra money, amplify their power and security and create a business they love.

Are you currently creating or marketing a product in the SaaS space!? If so, you will love and learn so much from this week's episode with SaaS marketing expert Corey Haines. Corey is a marketer, entrepreneur, podcaster, investor, and soon to be an author who is on a mission to help people and their products, services, and content get the recognition that they truly deserve.

Wondering how best to grow your audience or perhaps, how to fund your next trip to Ireland? If so, this week's podcast is a must-listen for you! This week, joining Conor on the show is special guest and serial entrepreneur Brennan Dunn. Brennan is the co-founder of RightMessage, a platform for online businesses to enhance their automated segmentation and website personalisation. In this episode, Brennan walks us through his fascinating leap from consulting into SaaS, launching and selling his project management tool Planscope and the accidental beginning of his thriving community, Double Your Freelancing, where he advises 50K + freelancers and agencies across the globe.

This week, joining the podcast is special guest, serial entrepreneur, and the king of shiny objects, Brian Casel. Brian is the founder of Zip Message, a popular video messaging tool for async conversations, which launched at the beginning of 2021. Brian recently sold and exited some of his earlier businesses, including Audience Ops and ProcessKit. Brian firmly believes that with each business opportunity came great learnings and experiences, which he has carried forward to get him to where he is today.

‘’If I don’t understand the cost of selling the product, how to price and how to monetize it, I’m kind of screwed. Right? And that’s why 70 to 90% of startups fail, they start with that first bucket, and they don’t look at the second bucket.’’ – Dave Parker.

Each week on the podcast, we are joined by inspiring business builders who openly discuss their entrepreneurial journey with us, sharing how they obtained their first customers and revealing what worked and what didn’t throughout the growing process. This week, listeners are in for a double treat as joining Conor on the show is tech guru and five-time founder, investor, coach and author Dave Parker. Dave was formerly the VP of Programs at UP Global (Startup Weekend & Startup America) which Techstars purchased.

“The biggest risk is not can you build this? The biggest risk is that no one cares. So how do you validate that someone will care? And how do you validate that someone will be willing to pay for what you are selling?’” – Rob Walling.

Calling all bootstrap founders! Joining us on today’s masterclass on launching and growing a business is special guest Rob Walling. Rob is an admired serial entrepreneur, investor, author, and host of the popular podcast ‘Startups for the Rest of Us’. Since 2005, Rob has guided thousands of startup founders through his widespread books, recordings, articles and MicroConf discussions.

Have you ever heard that to grow your business, you must think big? Well, what if we were to tell you that's not always the case. Joining Conor on today's episode is special guest Daniel Vassallo. Daniel is a master of taking small bets and has a fascinating story to share.

Daniel's professional career was a roaring success as he worked for the globe's largest e-commerce retailer, Amazon. However, despite the promotions, benefits, and the attractive six-figure salary, Daniel decided to take the bold plunge from his desirable full-time role into the unknown realm of self-employment on a mission to strike a more sustainable work-life balance.

In this episode, Daniel reveals his small bets portfolio strategy, openly shares his learnings from failure, and explores the benefits of aiming for low-hanging fruit. Daniel also unpacks the randomness and unpredictability of business and reminds us how success is never a guarantee.

Are you ready to ignite an idea, fire up your business and transform your life!? If so, you will love soaking up today's episode with entrepreneur expert Shane Melaugh. Shane Melaugh has founded multiple seven-figure companies, including Thrive Themes and is currently building his cultivating personal development community, ikario.

Shane's personal story is fascinating. His mission via ikario is to share his life experiences with as many people as possible to help them break free and transform their lives into beautiful success stories. In this episode, Shane openly shares how his life transitioned from constraints, struggles and an overwhelming sense of failure to finding freedom, wonderful success and ultimately, unlocking a better life. Throughout the discussion, Shane explores the importance of building on what already exists, reveals a brilliant tool for filtering through business ideas and highlights why we shouldn't overlook self-care and personal development.

Indie makers and marketplace shakers, this episode is a must-listen for you! Joining the podcast today is the prolific innovator and creator Jakob Greenfeld. Over the last two years, Jakob has successfully launched over fifteen software products and is the host of The Business Brainstorms podcast and creator of The Opportunities newsletter.

In this episode, we learn about Jakob’s journey from becoming a physicist to testing out the road of entrepreneurship with his bootstrapped products. Jakob gives us great insight into the early days of his workings, framework, and product launching tactics. Jakob also shines a light on taking shots on goal, the importance of authenticity, sharing your origin story and how to increase your business visibility.

Welcome back to season four of The First 10 podcast. Kicking off this season’s debut episode is special guest Andy Mackin. Andy is the proud CEO of the Mackin group, based in Cork and operating globally. The Mackin group consists of two renowned companies Mackin EHS a heath, safety, and environmental service provider, and Mackin Talent, a talent management solutions provider.

Andy is a wealth of business knowledge and has so many fascinating stories to share, along with valuable advice and tips on succeeding in business. Andy openly shares insights from the beginning of his entrepreneurial voyage, explores the power of discipline and consistency, and reveals the importance of building and nurturing your network. Andy also breaks down the superpower that is relationships and why the value of Relationships Matters is at the core of everything his dynamic global company does.

Season 3 of The First 10 Podcast will focus on serial entrepreneurs, and this episode is a short message about why.

A recap of some of the incredible wisdom shared by my array of guests this last season, as well as mention a few things I'm working on right now.

It’s easy to look back at our mistakes and wonder how things might have gone differently, if only. There is only so much value to be had in that mode of thinking. The moment has passed, the decisions were made and paths were taken.

What does remain is the learning, the residual growth that can, if treated non-judgementally, can be the route to future success. The only thing to do with a good failure is to appreciate it and milk it for all its worth. Move over ego, I’m mining this failure for all its worth.

Here is a list of 10 (more) things I’ve learned along the way that might help you improve your decision-making process.

It’s easy to look back at our mistakes and wonder how things might have gone differently, if only. There is only so much value to be had in that mode of thinking. The moment has passed, the decisions were made and paths were taken.

What does remain is the learning, the residual growth that can, if treated non-judgementally, can be the route to future success. The only thing to do with a good failure is to appreciate it and milk it for all its worth. Move over ego, I’m mining this failure for all its worth.

Here is a list of 10 things I’ve learned along the way that might help you improve your decision-making process.

Tom Hirst is a WordPress developer, business owner, author, creator, mentor, and Twitter guru. Tom has a passion for helping others get ahead by sharing his experience and learnings with people from all corners of the globe, guiding them to become better freelancers through his newsletter, courses, books and mentorship programmes.

In this jam-packed episode, Conor and Tom dive into the world of freelancing, discussing how to generate leads, pricing your work and marketing yourself consistently.

If a life coach and a business strategist had a baby, you would get Darrah Brustein. Darrah is a four-time founder, author, connector and coach at Mind Your Own Business, a community for service-based business owners focused on maximising their profit and impact.  

In this episode, Darrah discusses her steered transition into coaching, how to go above and beyond for clients and building a business that does not run you.

Matt Olpinski is a successful UI + UX designer and developer who teaches thousands of freelancers how to get more clients, raise their rates and create a better life for themselves.

In this episode, Matt discusses in depth how to operate as a freelancer. Matt shares how he accidentally fell into the world of freelancing and how you can find clients through your personal network by letting people know what it is that you do. Matt also reveals how he transitioned from being a full-time freelancer to running his agency and how he built his own lively community – The Freelance Institute.

Robbie Swale is a leadership coach who has built a successful practice of empowering clients to unlock their potential to thrive in their career, work, and life paths. Robbie’s clients include entrepreneurs, investors, theatre directors, and even other coaches. In this episode, Robbie shares his coaching journey, discusses getting comfortable with talking about money, the importance of honesty, and how we can improve our practices from learning through conversations with others.

Copywriting queen Margo Aaron is a wealth of business knowledge. Margo has taught thousands of students how to sell ethically, market honestly, and how to use words to stand out and inspire action. In this jam-packed episode, Margo and Conor discuss the rollercoaster of freelancing, hard learnings, the power of relationships, and the art and science of getting people to care.

Pete Shepherd is the 6”7’ founder of Human Periscope, co-host of The Long and the Short podcast and a head coach of Seth Godin’s altMBA, an online leadership and management workshop. Pete specialises in helping leaders around the globe to develop, grow and create great change by allowing them to see things they can’t. 


Jay Clouse is a writer, podcaster, and entrepreneur. Jay is the creator of Freelancing School, which provides the training and community to help people make a living freelancing. With three courses, coaching, and community support, Freelancing School has the tools to help creatives thrive as business owners.

Scott Perry is Creative on Purpose's Chief Difference-Maker and author of the Amazon top-sellers Endeavor and Onward. Scott is also the head coach for Seth Godin's Creative and Freelancer Workshops.

Scott has mentored and guided thousands of freelancers in helping them deliver work that is aligned with who they are and their key strengths, enhancing their own lives as well as the lives of others. In this episode, Scott shares with Conor his personal freelancing journey along with the key lessons he has learned throughout the adventure.

If I had just let some of those foundations myself in those early few years like my business would be in a totally different place right now like they're these are the old things that I'm like 2020 hindsight like those, those are the things that I would actually go back and change, quite painful to think about.

The power of habits in your business particularly when you're a one-person business, like a freelancer can completely turn your business around. It can help when you're lacking motivation, which happens to all of us when you're facing imposter syndrome, which happens with all of us. The power of habits can really, really drive your business forward.

Season 3 of The First 10 Podcast will focus on Freelancers, and this episode is a short message about why.

A recap of some of the incredible wisdom shared by my array of guests this last season, as well as mention a few things I'm working on right now.

And I think that a lot of really amazing art and design retailers and creators of products that are out there that have small businesses because of geographical restrictions or tech not serving them correctly. It's not right, and that problem needs to be solved.

The prerequisite you have to learn how to do that you have to stick it at doing the same thing. If you just like flitting around from marketing attempt to marketing attempt, or you know just doing it for two months and then not doing it for a while, I think you're just going to frustrate yourself and waste your time.

You may have 200 rejections, but the five or 10 that want to talk to you are people that have been thinking about the space long before you talk to them about it. And those are really the right people. And so if you get those type of investors, they're not going to ask you to focus too quickly.

That's the mistake a lot of people make when they're trying to get media in early stages. They just blast out what their product is product release. No one cares. No one cares what your product is literally no, not even your mom. No one cares. It's what's the story. And if you don't have that in your business, you need to find what that is.

Review of the First 10 Bootcamp and announcing the launch of the Freelancer Marketing Habit

You will be happier. And you'll find more success being really, really, really specific to target the exact type of customer. You want that as a need that your thing solves. And I think a lot of us, myself included, even you know, now after some years try to be something for everybody, and it's just not right. And like we all have to fight against that, I think.

“Customers, once they trust you with one thing, are potentially going to ask you to do many other things. But that’s where a lot of service businesses can get into trouble”

The “all or nothing fallacy” and Dan Pink’s To Sell is Human

“Don't frame your project as "research", instead tell your potential customer it’s up and running…and always be helping. It makes genuine business sense.”

I think you can get a customer with a decent looking website and a bank account, right? Maybe not even both people get lost in all the things they need to get a customer and it's like going to get a customer first and then you can figure out how to invoice them.

People seem to think that you have to have clarity before you take action. But it's exactly the opposite. In 99% of the cases I've seen, clarity comes from taking action and not the other way around, you don't have clarity and then take action. You take action, and then you get clarity.

“There are creative ways that you can either see if someone is willing to pay you, like put their money where their mouth is, or there are creative ways to actually get people to join in a journey with you, such as offering a discount, building a special feature for them with a pet project. There's so many ways to do that. And it's just going to serve you so much better in the long term, you'll be working on the right things”

Summary of key takeaways from Season 1 of the The First 10 Podcast

“The reasons why I maybe think the way I do or that I react to certain things in certain ways, has helped me to also better understand other people, and why other people think the way they do or act the way they do and helped. It's really helped me to empathise with other people more.”

“The First10, generally we don't know what we're doing. We don't know how to talk about it. We don't know what benefits the people we're talking to are looking for. And sometimes, if this is something you hone after talking to 5 or 10 people, you start seeing their objections..and this is what you can use to build, to tweak your offer and your messaging and everything you're doing for the next 10.”

“The first 10 people you meet aren't going to be your first 10 customers and that's okay. They shouldn't be because you're not for everyone. You can't be for everyone, right? The first 10 can come from anywhere, and it's probably likely that they're coming. They're not coming to knock on your door out of the blue. They're people, you know, they're people in your circle. They're people who have had experience with you before some other way and are willing to try something out because they trust you.”

“I'd say look, look close, there will be a blind spot, probably from your recent history. You already know somebody, already worked with a project you did before, an audience that you served once before, who actually would be great for this, but you've sort of skipped them over.“

“When you're asking questions that people say “I'm not comfortable answering that”, that's where the real nuggets of wisdom lie. And so, to me, that's what great discovery is. It's having a conversation with someone and not just scratching the surface. It's going deep.“

“I like to think of it as just being curious about people..…when you're curious about them, you can't really have any preconceived notions, you're just kind of like, Oh, interesting. You said this, tell me more like, like, why is this interesting to you? Why do you need this? Or what are your needs?”

“We often get caught up in this idea that we have this one idea. That's one thing or this one thought, and we need to make it work. But if we hold on to things too long, if we hold on to something good, we stop ourselves from getting to something great. “

“The difference between being top of mind and close to heart. And so, those first 10 like it's really easy to put a marketing strategy in place and spend lots of money to just kind of spread yourself out there and hope something sticks and hope something lands so reach is not the most exciting or important thing. And in those early days I think the effect of being close to heart, of mattering to someone is what's important and why those first 10 customers are so important because they will tell you so much, especially when launching a new business.“

“We have so little time to make an impact on people, we have to be very, very, very clear about what we want them to know about us. So in order to know that, you have to have a strategy, you need to know how you want to be positioned, which basically means how you want to be regarded by your target market, how did they want to think of you perceive what you can do for them, if you're very, very clear on that, and boil that down into something that's not going to take very long to deliver.“

“Identifying people and having a one-on-one conversation with them. And you would be really surprised how people want to help, as long as you make it genuine and you ask them in a really nice and transparent way. And if you get some no’s, you get some no’s. It's a part of it all.”

“Hello, hello, and welcome to the first 10 podcast. We've all heard the saying, if you build it, they will come. But when it comes to creating new businesses, the reality is more like, if you build a Dell probably do nothing. Every successful company that you can think of started with their first 10 customers, those early believers in your idea are crucial to your success.”