Since leaving Dubai and moving home to New Zealand at the beginning of October my day-to-day life has been transformed in nearly every way imaginable.

For the past 4 years I’ve well and truly lived the online business / digital nomad dream:

 • Living out of a suitcase for most of the year
 • Working from home
 • Running the business through Google Meet and Slack

Nowadays my life looks very different.
 
 • Having a stable ‘home’
 • Commuting to work in rush hour traffic (thank god for podcasts…)
 • Checking into our Morningside AI office in Auckland CBD every day
 • I’m working in-person with the team

If you had told me last year that I'd be trading my ‘freedom’ for a 9 to 5 office routine, I'd have asked if you'd had anything to drink!

But after seeing the world and the lonely side of constant travel, I'm ready for this new chapter - one that puts our team and organization's growth first.

The good news? I couldn't be happier.

Looking back on this winding journey - 670+ days of building in AI - I've gone from complete beginner to AI business to building multiple companies and generating over $3M in revenue (and counting!).

But it wasn't all smooth sailing.

Along the way I made plenty of mistakes that cost me time, money, and sanity.

Today, I want to share my 5 biggest regrets so you can avoid these traps and accelerate your own path to success in AI.

NOTE: If you’d like to watch my YouTube video on this topic you can watch it here instead!

Regret #1: Hiring the Wrong Developers

When I started Morningside AI, my AI Automation Agency, I made the rookie mistake of going straight to Upwork for developers. I filtered for top-rated AI devs, thinking I'd find what I was looking for.

Big mistake.

These in-demand freelancers treated us like just another client, leading to unresponsive communication and subpar deliveries. We constantly had to step in and manage projects that should have run smoothly.

The Fix: Look for developers who:

 • Understand your specific business model and tech stack (e.g. the AAA model)
 • Aren't marketing superstars (less in-demand = more attention for you)

Pro Tip: Check out the hiring tab in my free community. It's full of talented devs looking for work in the AI automation space.

Regret #2: Neglecting Content Systems

While I've grown to 260,000+ subscribers in less than 2 years, I regret not systemizing my content production earlier. The entire journey has been chaos of last minute uploads and squeezing in videos here and there.

This was largely because I always felt conflicted about spending so much time on content vs. "real" business operations.

The Reality: As your team grows to handle day-to-day operations for you, high-quality content becomes one of the most valuable things you can provide as a founder. It's not just about being a "content creator" – it's about driving business growth through the most effective marketing method in today’s world.

The Fix: Invest time in creating robust systems for consistent, valuable content production. This might include:

 • Content calendars
 • Schedule time for ideation, writing and filming weekly
 • Repurposing systems
 • Clear SOPs for editing and publishing so you can delegate it

Set a schedule that allows you to ‘get ahead’ without burning out. Until you are ahead you will be constantly stressed and unable to work on other parts of the business that need your attention!

Regret #3: Chasing Shiny Objects

The AI space moves at lightning speed, with new opportunities constantly emerging. It's easy to get distracted by every exciting lead or potential partnership.

My Mistake: We wasted months negotiating massive deals (like a promising military bidding SaaS play) that had a tiny chance of actually closing. This took focus away from building momentum with smaller, more achievable projects.

The Fix: Implement a strict opportunity evaluation process:

 • Measure new opportunities against your current core business and projected growth rates
 • Consider both potential outcome AND likelihood of success - ask yourself two key questions:

1. “How much could this make us in 5-10 years?"
2. "How likely are we to pull this off?"

If it can make significantly more AND has a high probability of success, only then allocate limited resources to explore it further. Never go all in.

Remember: a new business venture is far riskier than scaling your current one. The devil you know is better than the devil you don't - there are too many unknowns in new ventures.

Regret #4: Not Implementing Exploration Milestones Sooner

In the early days of Morningside AI, our sales process went straight from discovery call to full proposal. This led to tons of wasted time creating detailed proposals for leads that weren't serious (tire kickers).

Basically, there’s a lot of ‘AI enthusiasts’ out there. There are far fewer serious business owners ready to spend $10,000+. Never forget this!

The Game-Changer: We introduced a paid "Exploration Milestone" between discovery and proposal. For $800-$4000, we'd do a deeper dive, create a prototype, and deliver a feasibility report.

The Results:

 • Financially qualified leads
 • Improved cash flow
 • Increased our close rate (of those who started an exploration) from single digits to 80-90%

This was what allowed us to break through the $20,000 - $30,000 p/m range consistently and scale to our first $100,000+ month.

For more a full breakdown on this strategy check out my YouTube video on it here.

Regret #5: Competing Instead of Collaborating

When other creators started making AI business content similar to mine, my first instinct was defensiveness. I worried about losing my position or audience.

The Mindset Shift: Reaching out to "competitors" and turning them into collaborators has been a massive win for me. We now have a tight-knit group of AI content creators who:

 • Share knowledge and solve problems together
 • Provide support in a rapidly changing industry
 • Create opportunities for joint projects and growth

The Takeaway: There's often more to be gained through collaboration than direct competition, especially in a rapidly evolving space like AI. The market is growing faster than new people are entering. We aren’t fighting over limited resources here!

I hosted my crew of AAA creators in Dubai earlier this year, if you haven’t seen the podcast from that event you can watch it here.

Final Words.

While I say that I regret these things, I don’t really.

Discovering these gems was part of the fun. 

Those little (or big) changes you make that actually work and you see the business grow. That’s what makes entrepreneurship so rewarding.

So while you all can learn from my ‘mistakes’ and get ahead faster than I did, you all have your own mistakes to make, and hidden inside each is a satisfying learning that you will carry with you forward.

For those who are on the ropes right now and struggling, I want to remind you that AI business is the play right now. EVERYTHING points to this being the biggest opportunity for entrepreneurs of this decade.

Success is just around the corner. Don’t stop now.

I'll see you next week,

Liam 💪🏼

P.S. if you haven’t already watched my new course on starting an AI Automation Agency you can access it for FREE in my Skool community here.