50 Lessons Learned from 10 Years in Business

I left the security of the corporate world back in 2013 to pursue a side hustle called?Hotdesk, and never looked back.

In the time since, I’ve had a few modest successes in business and numerous failures.

My biggest success was?Collective Campus, a 7-figure tech consultancy that worked with huge brands all over the globe, and incubated 100 startups, helping them raise $200M in the process. It was named one of Australia’s fastest-growing new companies back in 2018.

Lemonade Stand, a kids' entrepreneurship program I founded, had modest success. It was a darling of the mainstream media but ultimately remained a low 6-figure business, teaching several thousand children entrepreneurial thinking in the process.

I spun off a number of businesses and projects such as?Metavise,?NoFilter Media?and?NewLaw Academy, as well as tons of media assets such as podcasts, books, online courses, and so forth, that had mixed results.

I learned a little from the successes and?a lot?from the failures.

As I near my ten-year anniversary as an entrepreneur, and take stock of what I’ve learned to help chart my own path forward, I thought I’d share my reflections, as some of these might help you on your own entrepreneurial journey.

So, without further ado…

1. Every business is different (the tools, tactics, and strategies that work for one business at one point in time might not work for another business at another point in time)
2. Your value proposition is everything. Are you solving a real and big enough problem or creating enough genuine value for customers?
3. Be laser-focused on one thing — the customer segment, the problem you’re solving, and so on. This makes it easier to align your marketing, copy, brand and so on. If you focus on too many customer types it becomes brutally difficult to get to hit brand-market fit.
4. Be customer-centric: listen, listen, and listen some more. Ask questions. Listen some more. Then introduce your solution.
5. In the beginning, you want to do one thing and hit one customer segment really well. The moment you branch out to multiple products and customer segments, you begin to seriously compromise your focus and execution across all areas of your business. Doing one thing well can help you build network effects within an industry, which creates a flywheel of sorts and makes it easier to sell going forward.
6. Focus on what you know.
7. When ready to scale (i.e. you have a predictable and repeatable sales process in place), hire competent salespeople — do reference checks, fire fast if need be. Don’t let one bad hire put you off what is a fundamental growth driver.
8. Content can be a powerful lead generator and sales closing tool. Create ebooks, blog posts, podcasts, videos, case studies, emails, and so on.
9. Relationships, relationships, relationships — keep them warm before, during, and after closing and delivering on work. Who you know is as important as what you know or what you do.
10. Align your work with strength, meaning, and joy — otherwise, it will feel like a job, and become difficult to sustain enthusiasm and high performance for the long haul. Don’t just pursue a business because it makes money.
11. Automate and outsource all repeatable, rudimentary tasks. You need to remain focused on high-value tasks and cultivate as much flow state as possible each day.
12. Be careful if/when outsourcing high-value tasks such as software development or UX design. When doing this, it pays to have at least one in-house or higher-paid contractor on board to direct such work.
13. Measure what matters. Then monitor and manage it.
14. Signals can be a very powerful source of market sentiment and leads.
15. Avoid generic outreach emails and be uber-targeted and personalized with your sales outreach and messaging. The time taken to target the right people, and personalize the right message will repay itself many times over in dollars.
16. Don’t enter saturated markets unless you can be 10X better — they’re usually a painful race to the bottom.
17. Just because you think it’s a good idea, and you’re enthusiastic about it, it doesn’t mean it will work. The optimism bias makes a fool out of you and me.
18. Fish where few are fishing but the fish are enough.
19. You need to adapt as markets change constantly. Don’t be left holding the bag.
20. Being the best isn’t enough. The market needs to know you’re the best. If they don’t, copycats will muscle in on your market share.
21. Follow up, follow up, follow up, follow up, follow up. No less than five follow-ups with sales prospects.
22. Call, call, call, call, call… email is not enough.
23. Go for recurring revenue models from day one. This will make your business much easier to sell in the future. Buyers want to see recurring revenue and a somewhat reliable EBITDA.
24. Use code, contractors, content, or capital to scale.
25. You can be global from day one. Doing so can be a blessing or a curse, depending on how you execute.
26. If you can, pay 50% to 100% more for better people. The right people will generate a lot more value than the extra dollars you pay them.
27. Get your unit economics right.
28. Good people are almost everything. Treat the good ones well. Cater to their professional and personal needs.
29. Most decisions should be made quickly. Empower your people to make decisions quickly. Wrong decisions made quickly can be learned from fast and corrected fast.
30. Task boards are key to managing workflows and getting the best out of people without micromanaging them.
31. Rapid experimentation is great but you need balance — be wary of premature false positives or false negatives when concluding experiments.
32. Social proof is a?very?powerful sales tool. Capture all client case studies in as compelling a medium as possible.
33. A few people will create most of the value (Brooks’ Law) so reflect on your people and their contributions frequently. Fire fast if necessary, and replace them with higher performers. Over time, this will improve the talent density at your organization.
34. Don’t fall into the trap of keeping people employed because (a) the relationship (b) comfort/familiarity, or (c) you’re shying away from difficult conversations. Chances are you can replace them with better, or outsource/automate their work for cheaper, or do it yourself quicker, or maybe what they do no longer adds any value
35. Have regular and transparent check-ins with your team about performance.
36. Hire people whose values align with the organization’s values, and ensure they buy into the mission.
37. Build a culture of extreme ownership and accountability for one’s work.
38. Build a culture of radical transparency.
39. 14-hour days are toxic, but 4-hour days might not be enough… six to eight well-structured, focused hours on high-value work seem sufficient and optimal for long-term performance and sustainability.
40. Tools are only as good as how you use them. Be careful with social media, Slack, and so on, as these can kill your team’s productivity and focus, whilst lulling them into a false sense of busy-ness.
41. Kill shallow and ‘insecurity’ work. Work shouldn’t be a crutch, it should help us become the best version of ourselves.
42. Life is a team sport. There’s little point in being successful in business if you don’t have people to share your success with. When you do have such people, it makes focusing and being successful in business much easier and makes the success so much sweeter.
43. Don’t underestimate the role of luck — you can do everything ‘right’ and still fail. Accept this fact, but try to increase your chances of being lucky by doing the work.
44. You can dramatically increase your surface area of luck by positioning yourself geographically and physically in the middle of areas densely populated with people of interest — be they customers, investors, and so on. This also extends to picking the right networking events and conferences to attend (but be careful not to confuse motion or entertainment with productivity when it comes to conferences — most conferences are an expensive waste of time).
45. The people you meet can open doors for you. Meet more people. Be a good and interesting person.
46. Deliver an awesome experience every time. This will create repeat business and referrals.
47. Influencer marketing can be a very effective way to dramatically expand your brand’s reach.
48. You can get almost anyone to do anything if you can make it all about them, and what they value. Knowing what that is and delivering it is the hard bit.
49. A solid and consistent brand and aesthetic across your assets reflects on your work and creates a sense of comfort for would-be customers.
50. Success in business won’t necessarily make you happy or content with your life. Happiness comes from a deeper place within ourselves, and the quality of the people we surround ourselves with. Don’t neglect your personal relationships or your physical and mental health for the sake of more money. Watch out if you find yourself saying “if I can just get X,?then?I’ll be happy”.