“To scale, it’s not what you start doing, it’s what you stop doing…
the only way to scale is to give things up.”
– Jim Estill
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In this episode my good friend Saud Juman and I have the privilege of interviewing Jim Estill, one of Canada’s most eccentric and notorious entrepreneurs. This man has invested in over 150 businesses, boasts 99 consecutive quarters of profit, and successfully scaled his first business, which he started out of the trunk of his car, from zero to $2 Billion dollars.

In the last couple of years Jim became famous for giving 1.5 Million dollars of his own money to secretly launch a resettlement program that brought 58 Syrian families into Ontario and provided them with housing, language training, and employment. He coordinated the entire program and didn’t even tell his own wife until it was ready for launch.

In this episode the three of us talk about the struggle of giving up control in order to scale a business, what to look for when you’re considering investments, understanding your company’s niche and finding your micro competitive advantages, and why Jim does not give money to his kids.

Show Notes:

10:11 –

Q: Can you give us a little context and share your story?

A: (Jim Estill)

  • Jim talks about how he grew up in Woodstock and had small businesses as a kid.
  • He went to university for computer science.
  • He joined SYNNEX.
  • He had 99 consecutive quarters of profit.

13:12 –

Q: Entrepreneurship now is sexy, was it sexy back then?

A: (Jim Estill)

  • Not at all – when Jim told his parents he was going into business his mom actually cried.

14:15 –

Q: Is there a recurring theme for success that still holds true at any scale? What are some of the fundamental lessons you’ve learned?

A: (Jim Estill)

  • There’s so many fundamentals in business. Jim’s businesses have not been inventive, but more distributive.
  • Jim’s focus has always been to try to come up with ‘micro competitive advantages’ – essentially tiny little competitive advantages.

15:45 –

Q: At scale, at a company that’s worth billions, what are those micro competitive advantages?

A: (Jim Estill)

  • The most obvious one would be to go into a company that’s the right size, and understand your niche and the market share that’s most appropriate to the size of your company.
  • As you grow, the market size that you can go after is bigger and bigger, but your company needs to be the appropriate size for the right market.


Q: Have you always known that you wanted to build a big business? Was that always your goal or did it just organically happen?

A: (Jim Estill)

  • When Jim was in University he said to himself that he wanted to build a $100M company.
  • His first businesses just kind of happened.

18:53 –

Q: Did you have to deal with being a bottleneck and micro-managing as you scaled your businesses?

A: (Jim Estill)

  • Yes he absolutely did.
  • The only way to scale is to give things up.

19:38 –

Q: What are some of those key hires when a founder wants to start delegating as they go from 8 figures to 9 and so on? Would it be a COO / Operations type person?

A: (Jim Estill)

  • He hires people to do the things he doesn’t like doing.
  • He also has learned that while you would love to have all A-Players, you have to have some people who are average on your team and upgrade them one at a time.
  • Jim is very frugal and has clear HR ratios for salaries: 1 highly paid person, 5 mid range salary, and 15 lower paid people. You just can’t get those ratios out of line, because if you do you don’t thrive.

21:35 –

Q: So you’re pushing back against the trend towards topgrading (90% high paid)?

A: (Jim Estill)

  • “I believe hire average people, our job is to make them above average through systems, process, training, coaching and mentoring.”
  • Slotting is also very critical.

22:58 –

Q: Going back to the time logs, you actually marked up your likes and dislikes?

A: (Jim Estill)

  • He breaks the day up into 15 minute increments and marks what he’s doing during those slots, which is why he only does it quarterly.
  • It is interrupting, but worth it.
  • He marks down: likes and dislikes, high energy and low energy, high productivity and low productivity.
  • Analyzes why he doesn’t like something, because you often can solve why you don’t like something.
  • Has been doing this for decades – wrote a book on time management.

25:15 –

Q: How have your days changed as the companies have scaled?

A: (Jim Estill)

  • Revenue levels haven’t changed the organization of Jim’s life, but different stages of life have (his kids are older now, he has more time for work).
  • He has found that as he gets older his energy level has gone down.
  • His competitive advantage used to be work ethic – he used to work very, very long hours.  But he can no longer ride on that.

26:45 –

Q: Validate or debunk this rule of thumb: businesses have to shift according to the rule of 3’s and the rule of 10’s as far as processes and as far as communication?

A: (Jim Estill)

  • Jim agrees but he has different numbers.
  • The rule of 50 – 1 person influences 7 people, who influence 7 people…
  • Most companies have a real challenge getting through that 50 person barrier (that’s a loose number).
  • The next challenge point comes at about 200 people – you can’t have a single social fabric with 200 people.

29:04 –

Q: Tell us the story about 20 keys.

A: (Jim Estill)

  • He was driving home from work, dead tired.. and the reason he was driving home so late was that he had the only key to the office and said to himself “I won’t be able to grow my business if I have the only key…”
  • It was symbolic, he had to trust his employees and it turned out to be liberating.

30:40 –

Q: A lot of people talk about the mechanics of scaling a business, but who does somebody have to become in order to grow?

A: (Jim Estill)

  • For Jim it’s all about micro competitive advantages.
  • The biggest one would be constant learning – as soon as you stop learning, your business stops growing.
  • When he was doing 50M, he would study people doing 100M, and so on.

32:40 –

Q: What’s the difference between an entrepreneur and a CEO? Does one have to cross that threshold at some point?

A: (Jim Estill)

  • “If you’re willing to study, you can become the CEO.”
  • Mentorship is the difference. Jim’s also been a voracious reader (does not watch television) and loves audiobooks and podcasts .

34:35 –

Q: What is one of the books that you’ve gifted the most?

A: (Jim Estill)


Q: You were on the board for Blackberry which grew but then lost a large amount of its market share – Is there a takeaway from the demise of that company? What happened? Did they take their eye off the ball? Did they get cocky?

A: (Jim Estill)

  • They underestimated Apple, and they did have an arrogance that made negotiations with carriers difficult.
  • High growth… and high growth means waste which is difficult to keep under control.
  • Waste and inefficiency grows exponentially. You’re most vulnerable when you’re most successful.

41:30 –

Q: What do you look for? What’s the weighing factor in you investing in a company? Is it the entrepreneur themselves or their idea?

A: (Jim Estill)

  • “You want entrepreneurs to be coachable but you don’t want them to be too coachable.”
  • The best entrepreneurs have enough bravado to not be completely coachable, but they’re still open and listen. It’s a tightrope.

43:30 –

Q: Do you see anything really super special out there in terms of products or companies?

A: (Jim Estill)

  • “Most successful businesses will be doing stuff that other people already do, it’s a matter of them having their own little niche, their own competitive advantage but I don’t think there’s that much rocket science”
  • The world focuses on the unicorns… but you don’t just have to hit grand slams to get people in.

44:25 –

Q: How active are you in the businesses that you invest in?

A: (Jim Estill)

  • Depends – sometimes your involvement is high where you add value and less in other things.
  • Tends to stay within tech. His experience has been when he goes outside of that he loses all of his money – “Every time I try to invest outside my field I lose money.”

47:05 –

Q: What percentage of your net worth do you allocate to investments? And how do you split that up?

A: (Jim Estill)

  • Safe investments are what I stick to.
  • A good rule in angel investment is you want to have 3 times what you’re investing – gives you follow-up funds that you will need in case investments fail.

48:41 –

Q: What is your view of wealth?

A: (Jim Estill)

  • I have friends who are already worth a lot who are out there trying to make more money but that’s not who I have chosen to be.
  • Everything above and beyond that “number” Jim gives away.

51:30 –

Q: How do you instill grit, hustle and hunger in your kids considering their relative privilege?

A: (Jim Estill)

  • “If you make your children’s life too easy they will never stand on their own… So I actually don’t over-support my children.” He does not have his children working in his businesses.
  • Jim doesn’t think it’s healthy to give them anything. The only thing he helps them with is their first house.

58:05 –

Q: We take our entrepreneur identity and we wrap it up with who and what we are – we measure our success as a person by our success in business. What’s your take on that?

A: (Jim Estill)

  • “If you’re an entrepreneur you’ll definitely commingle these two things regardless.
  • I’ve always said “fail often, fail fast, fail cheap. Having a failure does not make you a failure.”
  • “I am successful because I have more failures than most people.”

1:01:45 –

Q: Has the urgency of time management been with you always or has it gained more importance as you’ve gotten older?

A: (Jim Estill)

  • It’s always been there.
  • He’s always had this drive to grow and that means being pressed for time.

1:02:55 –

Q: Why didn’t retirement work for you?

A: (Jim Estill)

  • Partly the reason he sold his business was fear… He didn’t want the business to die before getting off.
  • He had always enjoyed mentorship and investing but he learned that you don’t get as much juice sitting on the sidelines.

1:04:45 –

Q: What does your average day look like now?

A: (Jim Estill)

  • The beauty about being a CEO is there is no average.
  • He has in office days but he also travels a lot.
  • He always works out and get his emails down to 0 every day.
  • He does a lot of journaling, spend at least 20 minutes a day outside, and is a huge advocate of walking meetings.

1:12:35 –

Q: Is business always on your mind or are you able to shut off?

A: (Jim Estill)

  • He tries, but it’s not easy.
  • Always carries a pen – if he writes it then it gets it out of his mind which is a waste of mindspace.

1:14:45 –

Q: How do you find a mentor?

A: (Jim Estill)

  • He looks for people that he genuinely likes.
  • But he often refers people to books.

1:26:56 –

Q: What is one word that you hope people will use to describe you?

A: (Jim Estill)

  • Other than eccentric, congruent. Real.

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