Tales from a 'failed' start-up

Updated: Nov 15, 2021

31 lessons learned and a cautionary tale of hope.


It is not the prettiest article I’ve written, but I think it's the most helpful to-date.


31 lessons learned the hard way over 4 years as I tried and failed (so far📈), to build a thriving online community.


If you are thinking of going - or have already gone - out on your own as a consultant, coach, or wannabe entrepreneur this article is for you. If you are thinking of investing your time in a side hustle, designing an app, or creating a community, there are valuable lessons here.


Before you ask, would I do it again? 110%. Would I do it differently. 110%.


Those are two important questions, but the most important question to ask is whether or not I'm happier and healthier now, than I was 4 years ago.


110% 💥


Click any of the links below to go directly to that lesson.


1. Find mentors (dead or alive), 2. Get advice from Google, 3. Ask for advice, 4. Pay for advice, 5. Use online marketplaces to save money and time, 6. Create a team, 7. Treat your start-up like a science experiment, 8. Never forget the 2x Rule, 9. Don’t forget sales and marketing, 10. Create your own luck by taking small risks, 11. Remember the Stockdale Paradox, 12. Redefine success, 13. Read a lot, 14. Do it for the right reasons, 15. Work with people you like, 16. Start small, 17. Don’t build an app, 18. Create a ‘coalition of the willing’, 19. Trust your gut, 20. Manage your time, 21. Manage your stress levels, 22: Always give back, 23: Detach from the outcome, 24: Don’t forget fun, 25: Remember it’s a marathon, not a sprint, 26. Crowdfund for the right reasons, 27: Create better habits, 28. Build boundaries, 29: Develop an abundance and collaboration mindset, 30: Remember there is a well-trodden path to follow, 31. Focus on fuzzy vision


It’s a long list, but not exhaustive, so if you have any lessons to add share them in a comment so we can learn from you. If you have any questions or want me to expand on any lessons just ask.


The lessons are not listed in any order of importance, and the idea is that you can dip in and out of the article in your own time. So I suggest you bookmark it for later.



1. Find mentors (dead or alive)

“What if I assembled a tribe of mentors to help me?” Tim Ferriss


I'm starting with this quote because in some ways Tim Ferriss is the apex predator of mentors. He’s made a career out of talking about and sharing his knowledge of mentors. Here is a select list of mentors that I’ve received advice from lately:

  • Tim Ferriss

  • Ram Dass

  • Jim Collins

  • Lao Tzu

  • James Stockdale

  • Marcus Aurelius


4 of these people are dead. Mentors don’t have to be someone you know, or even alive to give you advice.


There are millions of amazing people in the world just waiting to become one of your mentors. So, don’t limit yourself to people in your network.


A case in point for me is Marcus Aurelius, he is one of my mentors and he has been dead for over 1,800 years. Ideally, you have a few mentors in your personal network. But you should also find hyper-successful people (dead or alive) whose lessons resonate with you.



2. Get advice from Google

“For business, our internet love affair was a gift from the gods.” Gary Vaynerchuk


Before you pay for advice or ask your network the wrong questions, use the internet and the millions of sources available – like this article – to get advice. There is free info about almost anything and everything you need to know about starting a business online. I never pay for advice until after I have first done my homework using Google.



3. Ask for advice

“Be careful who you get advice from. I get advice from people who are where I want to be.” Robert T. Kiyosaki


Once you have some good questions don’t be afraid to ask for advice from your network. There are hundreds of people that have given me their valuable time and advice over the past 4 years. From ex-colleagues, the Surf Club, personal network, wife’s friends, school friends, so many people have helped me it is humbling.


Importantly, when asking for advice be as specific as possible about what you’re looking for so as not to waste your contact’s time. And try and give them something in return for their advice, whether that’s simply a thank you email, a bit of advice of your own, or a small gift (at the very least pay for the coffee!).



4. Pay for advice

“A consultant is someone who saves his client almost enough to pay his fee.” Arnold H. Glasgow


Yes, I’ve had great advice from my network. But, paid advice from a specialist can help you take a step change and/or create the clarity you need to move forward.

My recommendation is to a] do the research and planning yourself first, then b] get free advice from your network, and finally c] get paid advice.



5. Use online marketplaces to save money and time

“There are two fools in every marketplace; one asks too little, one asks too much.” Alan Sugar


My brother-in-law and business partner Jez taught me this lesson (more about him later 🦸‍♂️).

There are good online marketplaces out there - Fiverr is my favourite - where you can outsource work that you’re not very good at. Or get expert (and some not so expert) advice for a relatively low investment.


I’ve mostly used online marketplaces for help with creative, design, technical marketing, and specialist consulting. Think website developers, designers, graphic design, branding, SEO, SEM, content creation [be careful outsourcing certain content as you need to remain authentic], digital collateral, social media, etc.


A word of caution; it can take some time to find the right contractor or consultant on these platforms. As I’m based in Australia, the contractors are more cost effective than I can get locally, sometimes less than 20% the investment. But you need to be prepared for some trial-and-error when finding a good contractor. My advice is if it’s a simple / short task that you’re capable of completing yourself, then you might be better off doing it yourself rather than outsourcing (due to the set-up, management, and transaction cost [time and money]).


However, if it’s a bigger job, completely out of your skillset, or ongoing work, then using an online marketplace can save you a lot of heartache and money.



6. Create a team

“Great things in business are never done by one person, they are done by a team of people” Steve Jobs


One of the best decisions I’ve ever made in business was calling my brother-in-law Jeremy (Jez) Horne mid-2017 and asking him if he could help me out with the digital side of my first business idea “The Cave Network”.


Since then, we’ve gone into business together and are joint partners in MVLS Digital. We’ve spent more money than we’ve earned (don’t ask!), had heaps of fun, and made plenty of mistakes along the way (probably more me than him 🙄).