35 Business Lessons From My Mentors

One of the reasons I enjoy flying planes, is that it’s damn humbling to be a beginner again.

With flying, there’s a lot of information to learn.

And I noticed something interesting about this new information…

I only truly “know” a piece of information when I’ve encountered it in multiple different situations.

Know what I mean?

For example, it’s one thing to memorise your downwind checks from your theory book. (That’s for when you’re preparing to land.)

It’s a whole other thing to carry out the checks at 1,100 ft, with the sun in your eyes, warm air throwing the plane around like a rag doll, and radio information from the tower telling you to join a queue of incoming traffic.

There’s knowing something in theory, and there’s knowing something in your bones.

I find the same in business.

Many of the big lessons I’ve learned in the last couple of years, I remember hearing in podcasts over 10 years ago.

In theory, I’ve “known” that stuff for 10 years.

But when I came across that exact situation in my business, somehow “knowing” the answer wasn’t enough.

I had to experience it in order to truly know it.

And this brings me to mentors.

I’ve had many business mentors over the years, and the immense value of mentors is that:

Mentors give you that “first contact” with ideas.

Often, you’re not ready to “know” the information just yet.

But it makes it so that when the appropriate situation comes up in your business, you’re ready to learn it for real.

Mentors speed up your learning cycle.

They make it so that you learn your lessons faster.

And so, in celebration of everyone who’s helped me over the years, I proudly present… a humungous list of the biggest lessons my mentors taught me.

There’s probably $10M of value here…

Part 1 - Mindset

  1. 1
    Business goes in seasons - Just like life, a decision can look very different depending on the season you’re in. Be sensitive to that and you’ll make better decisions.
  2. 2
    Alignment is a secret weapon - Mindlessly chasing bigger numbers while neglecting what you want out of life is immature and lazy. The better I know myself, the more I am saying “no” to all kinds of business opportunities. (This is a lesson I have to continually learn.)
  3. 3
    Speed to implementation - I’ve noticed that all successful people seem to run their business lives based on this metric. “When should I get this done by?” “How about today?” The faster you implement, the faster you learn. (Note: This does not contradict the last point in the list.)
  4. 4
    Money is 99% psychology, 1% reality - You have to redefine your relationship with money as an entrepreneur. Money is not for security, it’s for deploying.
  5. 5
    Practice non-attachment - You mustn’t attach your sense of self-worth and happiness to business outcomes.
  6. 6
    Mentors - All the most successful people have coaches and mentors. What does this tell you? Mentorship is the biggest ROI you’ll ever get.
  7. 7
    Beware lifestyle upgrades - Increasing your lifestyle expenses excessively will undo any real-world benefit from growing your business, and make it so that you never experience the fruits of your success.
  8. 8
    Know what “enough” is - There is such a thing as “enough”, and you should know what enough is. (Side benefit: It makes business decisions a lot easier.)
  9. 9
    Most people prefer a paycheque - Most people are not entrepreneurs, nor do they want to be. Most people prefer a steady paycheque and a simple life. Remember this when building your team.
  10. 10
    You don’t have to scale - Scaling comes with consequences, and you don’t have to chase it… even if everyone on Twitter is talking about “10X-ing”. If you don’t want a larger team, shrinking margins, and big spreadsheets… that makes you normal! (Be careful what you wish for.)
  11. 11
    Never let two lawyers negotiate directly - This bill gets large, fast. Instead: Ask one side for an “issues list” and work through it yourself, offline. Once you’re done, send it back for comments. This advice has saves me $10,000s.

Part 2 - Strategy

  1. 12
    “Faster and Easier” - For education businesses, the fundamental aspects of your offer that people will pay for are “faster” and “easier”
  2. 13
    Don’t use fancy email automation until you’re at $1M - Fancy behavioural automation (tagging, conditions, segmenting etc) only matters if the underlying business is solid. And if the business is solid, you don’t need the fancy stuff to get to $1M. Ergo, don’t waste time on behavioural automation until you are > $1M. (This one makes people crazy, but there’s a deep truth to it.)
  3. 14
    Teaching people how to make money increases your income, fast - This is a tough pill to swallow for educators. However, if you can somehow connect “make money” to your offering, it drastically raises your earning potential. (At StoryLearning, I did this with our certification.)
  4. 15
    What can you charge $10k for? - New entrepreneurs tend to be anchored to low price points. But there are always customer segments who will spend far more… If you have the right offer. Someone asked me this question early in my career, and it taught me an important lesson about how experienced entrepreneurs think.
  5. 16
    Guard access to you - Access to you is the most valuable thing in the eyes of your customers. Therefore, it’s the most expensive thing you should ever offer and must be closely gated.
  6. 17
    $3M in annual revenue is a sweet spot - Businesses that grow beyond $3M get complicated quickly, often with negative lifestyle consequences for the founder. When my mentor taught me this, it validateD a lot of my instincts around how quickly I wanted to grow.
  7. 18
    Data isn’t everything - Often, the most important things in your business cannot be tracked, so we settle for less important metrics that we can track. Big mistake. When data and tracking fail, instinct and belief take over. This is powerful and good.
  8. 19
    Business challenges at scale are highly predictable - When I was growing StoryLearning, it felt like every business challenge was unique to me. Turns out, everyone runs into the same challenges at different stages of business. (Usually tracking revenue levels.) This helps me in mentoring other entrepreneurs, because I often know what challenges they have even before they do!
  9. 20
    Most marketers are “day traders” - Marketers are always incentivised to produce short-term results, which leads to short-term thinking. When I was given permission to think like a “value investor” instead, I looked at growth in a different way.
  10. 21
    Built a cult around your personality - Russell Brunson first turned me on to this, and then I started to see it everywhere. The world is a noisy place, with a lot of competing information, mostly with zero personality. By having the courage to be yourself, you instantly attract people who are looking for likeminded souls.

(In case you’re interested, this is why I’m always referring to Hobbitshire, my 6-day work month, and my hobby of flying planes. It’s what I have that’s unique to me, and consequently, it’s one of my biggest assets.)

  1. 22
    Make more offers - If you have a list of customers, one of the fastest ways to grow your business is to simply offer more stuff for sale. This means you need enough products in the first place. So make more products.
  2. 23
    You don’t have to scale - My world did a full 180º when I was first told that I didn’t have to endlessly keep scaling. Got a profitable business? Guess what – you’ll probably enjoy life more by just staying put.
  3. 24
    A-players come with a lot of baggage - I always heard that you had to hire A-players if you were serious. But then a mentor told me about the baggage that can come with hiring heavy-hitters (ego, team, culture shock, etc). I decided to always hire from within instead, and it’s proven to be a great decision. (See chapter 8 of the Case Study for more on this.)
  4. 25
    The bigger you get, the more you need consultants - Courses, masterminds and conferences are useful when you’re starting out, but their big limitation is that the advice you get is generic. Instead, as you grow, you need eyes under the hood of your business, to work the specific problem. This is what consultants are for. When I quit group events, and started spending money on individual help, we took big strides forward.

Part 3 - Marketing

  1. 26
    Study A-List copywriters - The reason copywriting is such a deadly skillset is that copywriters need to understand all aspects of the business to do their job: avatar, languaging, positioning, offer, objections, sales. Frankly, they put everyone else to shame. Studying copywriting was the most valuable thing I ever did.
  2. 27
    The Holy Metric - Only one metric matters in paid acquisition campaigns: [average cart value] divided by [cost to acquire customer] (ACV/CAC). This is useful because it helps you filter out the noise and stay focused on what matters.
  3. 28
    Use different modalities - Webinar, VSL, long-form sales page… however you sell, not everyone consumes information that way. So, send people the slides to your webinar. Make a VSL version of your sales letter. Put subtitles on your VSL. Sell in different ways, you’ll sell to more people.
  4. 29
    Write copy for an 8-year-old - It took me years to accept this, but today I swear by it. Good copy is about communicating basic points in stupid-simple language. That’s when it hits home. (See my Spanish Uncovered sales page for an example of this.)
  5. 30
    Look at email sequences side-by-side - I used to be lazy and treat email sequences as individual emails. But your audience is reading them sequentially, right? So, write your emails in advance and look at them side-by-side on a big screen. You’ll spot inconsistencies and opportunities for improvements.
  1. 31
    Relevancy is a super power — Scott Oldford taught me about the importance of continuously refining everything you do (emails, tweets, short-form video) to be laser-targeted to your avatar’s specific needs. It’s a real discipline. If most people just worked on their relevancy, they’d see a huge jump in revenue.
  2. 32
    Split testing is usually a complete waste of time - Another one that’s guaranteed to ruffle feathers. Look: Unless you have very high traffic, data from split testing is likely useless. In most cases, big, audacious tests (e.g. switch up the entire offer) will get you faster results than playing smart with AB testing.
  3. 33
    The best lists are small and curated - Use friction and barriers as a tool to filter out the wrong people. (Like a 117-page case study, for example. Ain’t most people gonna bother reading that!) You’ll get a more responsive, higher-quality audience, and that will result in you building your business in a stronger, less reactive way.
  4. 34
    Teach through stories - Whatever you want to teach, you’ll make it more memorable by telling it in a story. I learnt this from André Chaperon and my life has never been the same since.
  5. 35
    On video, be 2X your normal self - My early YouTube videos were dull as dishwater. But then, someone told me you need to have 2X your normal energy levels on video… just to appear normal. My videos improved instantly when I was told this.

So, that’s your lot.

Phil, Russell, Jason, Michael, Scott, Ben, André, Peter… thank you.

Feels kinda weird making a silly listicle out of things that made such an impact on me.

But if there’s one thing in here that helps you… it’ll be worth it.

Anyway…

If you enjoyed this, please do me a favour and forward it to a friend. A leave me a comment below with your favourite tip!

Namaste,

Olly

CASE STUDY: Blueprint Of A $10m Online Education Business:

  • Business model blueprint
  • Product ecosystem
  • Team structure
  • Evergreen sales strategy
  • And much more

Join my free newsletter for online educators and I'll send you the case study immediately...

We will protect your data in accordance with our data policy!

Leave a Comment