Thread
Over the last few years, I’ve grown my bootstrapped business to $50M+ in revenue.
The headline sounds great, but it wasn’t pretty.
There was a lot of failure, misstep and doubt along the way.
Here are 20 hard earned (non-fortune cookie) lessons, I picked up along the way:
The headline sounds great, but it wasn’t pretty.
There was a lot of failure, misstep and doubt along the way.
Here are 20 hard earned (non-fortune cookie) lessons, I picked up along the way:
1. There are 3 types of trust: Intent, Competence and Judgment
- Intent: heart is in the right place
- Competence: head is in the right place
- Judgment: heart and head work together
In any situation of disagreement, identify which type of trust is in question.
- Intent: heart is in the right place
- Competence: head is in the right place
- Judgment: heart and head work together
In any situation of disagreement, identify which type of trust is in question.
2. Everybody wants authority, less want responsibility, few want accountability
Authority puts you in a position to fulfill your responsibility.
Accountability is owning the outcome of your responsibility.
Accountability is the #1 metric I judge my leaders by.
Authority puts you in a position to fulfill your responsibility.
Accountability is owning the outcome of your responsibility.
Accountability is the #1 metric I judge my leaders by.
3. Strengths and weaknesses are two sides of the same coin
- Detail Oriented = Analytical / Paralysis
- Idea Generation = Innovation / Scattered
- Hierarchy = Structured / Inflexible
- Multitasking = Productive / Unproductive
Juice the former, squeeze the latter.
- Detail Oriented = Analytical / Paralysis
- Idea Generation = Innovation / Scattered
- Hierarchy = Structured / Inflexible
- Multitasking = Productive / Unproductive
Juice the former, squeeze the latter.
4. Don’t shy away from being overwhelmed
Being overwhelmed is good. It means you’re stretching your capabilities.
The solution is typically some combination of 4 things: (1) personally get faster, (2) hire someone, (3) develop someone, (4) improve your operations.
Being overwhelmed is good. It means you’re stretching your capabilities.
The solution is typically some combination of 4 things: (1) personally get faster, (2) hire someone, (3) develop someone, (4) improve your operations.
5. Adopt an “it’s my fault” attitude
- Sales were too low? It’s my fault
- Employee NPS is down? It’s my fault
- Customer isn’t happy? It’s my fault
The more quickly you do this, the more quickly you problem solve versus finding something (or in most cases, someone) to blame.
- Sales were too low? It’s my fault
- Employee NPS is down? It’s my fault
- Customer isn’t happy? It’s my fault
The more quickly you do this, the more quickly you problem solve versus finding something (or in most cases, someone) to blame.
6. Perception is reality and that isn’t good or bad on its own.
Sometimes it’s amazing - you get way more credit than you deserve.
Sometimes it really sucks - you get way less credit than you deserve.
This is part of the game. Embrace the good, fight the bad.
Sometimes it’s amazing - you get way more credit than you deserve.
Sometimes it really sucks - you get way less credit than you deserve.
This is part of the game. Embrace the good, fight the bad.
7. Ego is the most common enemy of progress
Differences of opinion can quickly escalate from healthy debate and searching for truth to battles of pride and proving “who is right.”
The former builds camaraderie, the latter builds resentment.
Differences of opinion can quickly escalate from healthy debate and searching for truth to battles of pride and proving “who is right.”
The former builds camaraderie, the latter builds resentment.
8. You are not responsible for your first thought, but you are responsible for your second thought
It’s natural to have gut reactions. You’re human after all.
Focus less time on trying to control that thought and more time on reflecting / honing your reaction to that thought.
It’s natural to have gut reactions. You’re human after all.
Focus less time on trying to control that thought and more time on reflecting / honing your reaction to that thought.
9. If left unchecked, impediment to action becomes action itself.
You don’t always have to have the right answer as a Leader. But you do need to know what questions to ask.
Otherwise what stands in the way becomes the way.
You don’t always have to have the right answer as a Leader. But you do need to know what questions to ask.
Otherwise what stands in the way becomes the way.
10. Calendar > To-Do List > Email
- Email is what OTHER people think you SHOULD work on
- To-Do List is what YOU think you SHOULD work on
- Calendar is what YOU (usually) ACTUALLY work on
@destraynor taught me this.
- Email is what OTHER people think you SHOULD work on
- To-Do List is what YOU think you SHOULD work on
- Calendar is what YOU (usually) ACTUALLY work on
@destraynor taught me this.
11. Color code your calendar
If your calendar is actually your source of truth - then color coding it helps you visually soft track your time.
For me:
- Blue - Strategy
- Green - Recruiting
- Purple - 1:1s
- Orange - Customers
- Red - Prospects
If your calendar is actually your source of truth - then color coding it helps you visually soft track your time.
For me:
- Blue - Strategy
- Green - Recruiting
- Purple - 1:1s
- Orange - Customers
- Red - Prospects
12. Readjust your calendar every quarter
Every 3 months, I reflect on all my standing meetings. I ask:
- Does this need to be a meeting?
If so,
- Does the length make sense?
- Does the frequency make sense?
- Does the time of week make sense?
Every 3 months, I reflect on all my standing meetings. I ask:
- Does this need to be a meeting?
If so,
- Does the length make sense?
- Does the frequency make sense?
- Does the time of week make sense?
13. Don’t hire Execs from big companies
An Exec in a $50M company is very different from an Exec in a $1B+ company.
The right Exec for this stage is comfortable doing the job & managing the job.
Many BigCo folks say they want to "be entrepreneurial"; in reality, they don't.
An Exec in a $50M company is very different from an Exec in a $1B+ company.
The right Exec for this stage is comfortable doing the job & managing the job.
Many BigCo folks say they want to "be entrepreneurial"; in reality, they don't.
14. Hire a team of Rogers and Tigers
Tiger Woods was an uber specialist (golfing since age 2)
Roger Federer was the consummate generalist (didn’t start playing tennis until 11).
Early in your journey hire smart, hungry generalists. As you grow, hire best in class specialists.
Tiger Woods was an uber specialist (golfing since age 2)
Roger Federer was the consummate generalist (didn’t start playing tennis until 11).
Early in your journey hire smart, hungry generalists. As you grow, hire best in class specialists.
15. The real risk in hiring is hiring too many Bs
There are 3 types of employees: As, Bs and Cs.
Conventional wisdom says Cs are a big risk. I think that’s wrong. Cs are easy to identify/fire.
Bs are the ultimate passenger and they burn out your As (the drivers).
There are 3 types of employees: As, Bs and Cs.
Conventional wisdom says Cs are a big risk. I think that’s wrong. Cs are easy to identify/fire.
Bs are the ultimate passenger and they burn out your As (the drivers).
16. There’s a difference in being a manager and a leader
A manager is really good at delegating - identifying who needs to do the job.
A leader is really good at synthesizing - taking multiple points of view and putting forth an objective and direction.
A manager is really good at delegating - identifying who needs to do the job.
A leader is really good at synthesizing - taking multiple points of view and putting forth an objective and direction.
17. Culture is built in moments of continuity and tested in moments of adversity.
Culture isn’t concrete ; there are no deadlines, goals or metrics.
But it’s something intangible you have to invest in daily or when a boulder hits (and it will), the house will collapse.
Culture isn’t concrete ; there are no deadlines, goals or metrics.
But it’s something intangible you have to invest in daily or when a boulder hits (and it will), the house will collapse.
18. Customers only care about themselves. As they should.
They don’t care about how many employees you have, how much money you’ve raised, how many times you’ve been featured in the press.
They care about how quickly and painlessly you solve their challenge.
They don’t care about how many employees you have, how much money you’ve raised, how many times you’ve been featured in the press.
They care about how quickly and painlessly you solve their challenge.
19. Your culture determines your financial results
Put #17 and #18 together and you realize that long term performance is a function of employee sentiment.
😀Employee = ⬆️dedication = ⬆️service = 😀customer = 🚀long term performance
Put #17 and #18 together and you realize that long term performance is a function of employee sentiment.
😀Employee = ⬆️dedication = ⬆️service = 😀customer = 🚀long term performance
20. Always keep shooting your shot.
- ⬆️attempts = ⬆️misses
- ⬆️misses = ⬇️importance per miss
- ⬇️importance per miss = ⬆️attempts
The dirty little secret of success is, most of the gains come from a handful of the attempts.
- ⬆️attempts = ⬆️misses
- ⬆️misses = ⬇️importance per miss
- ⬇️importance per miss = ⬆️attempts
The dirty little secret of success is, most of the gains come from a handful of the attempts.
