Tobi Oluwole

In my first leadership role, I changed all the processes on day 1.

I wanted to show my new team that there was a new sheriff in town.

Within a week, I had lost the trust of the entire department and people wanted me gone.

It took months to turn around and win my team's trust back.

And if I hadn't turned it around, I'm sure my actions would have started to affect them in other ways.

The worst bosses I've had in my career have also disrupted my sleep schedule, made me cry in public and caused me a lot of anxiety.

My favourite managers have made me feel like I'm capable of anything and have boosted my overall confidence.

They backed me for promotions, defended me when I wasn't in the room, fought to get me the compensation I deserved and cared about my life outside of work.

This post has gone viral on multiple platforms for a reason.

More than 300,000 people have liked it and over 15 million people have seen it.

Because it's true!

Your manager has more impact on your mental health than your therapist or your doctor.

Having a good boss can literally change your life.
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I’m building a community for people who want to retire from corporate in the next 5-10 years to live life on their own terms. Join the waitlist: https://bit.ly/41P1KAQ

I tried to recruit my friend to join Shopify.

He has been with his company for 4 years.

I told him about the pay, the benefits, how amazing the people are and everything else.

He just smiled and said:

“I love my team, I’m doing what I love and I’m happy with what I make.”

That was pretty much the end of the conversation.

It was almost like nothing else mattered.

It’s hard to lure someone away from where they feel valued.

Ghosting needs to stop.

Recruiters ghosting candidates after rounds of interviews.

Candidates ghosting companies after accepting an offer.

Companies ghosting candidates that try to negotiate.

Clients ghosting business owners.

All of it needs to stop.

If you’re a candidate: have the conversation and explain your reasoning.

If you’re a recruiter: share feedback to help the candidates get better.

If you're a client: tell the company you're no longer interested.

The world would be a better place if we all stopped treating everything like transactions.

Let’s start treating each other as human beings.

My wife and I bought our first house in Canada at 25.

A few months into the pandemic in 2020, I had just started my job at Shopify and my wife had just been laid off from Uber.

For some reason, I thought it would be a great idea to buy a house when everyone was too scared to do anything.

Within 10 days, we signed for a pre-construction townhouse in Ottawa.

Even though we barely had enough for the first deposit.

I had faith that everything would work out. And it did!

We moved into our first home in May 2021.

I still remember the look on our parents faces when they came to visit for the first time.

Then in May 2022, we bought another pre-construction house in anticipation of our future family.

We wanted enough space to allow our parents, siblings and future kids to be able to stay under one roof over Christmas.

So today we’re selling our beautiful home on Chipping Circle and getting ready to move.

The Canadian dream continues.

I arrived in Canada in 2010 as an international student

Did a year of high school in Hamilton, Ontario

Started at Carleton University in 2011

Failed most of my 3rd year classes in 2014

Almost dropped out because tuition was too high

Built my first 5 figure business in 2015

Graduated in 2016 and landed a tech sales job.

Got laid off from that job in 2017

Was on EI and had to borrow money from friends for 4 months

Started a clothing business summer of 2017 and lost over $10,000

Landed a new job in September 2017 with less pay

Fired in 2018 for being too distracted at work

Landed a new tech sales job in summer 2018

Sold $800k+ worth of software under the greatest boss I’ve ever had

Got a 20% raise in 2019 and married my best friend!

Helped both of my siblings get great jobs in 2019

Joined Shopify in May 2020 on my 7th attempt

Bought a house with my wife in June 2020

Moved into the house in May 2021

Bought my dream Tesla in June 2021

My parents arrived this week to witness it all.

Seeing the pride in their faces made me realize that it was all worth it.

That’s the Canadian Dream.

There is no such thing as “overnight success.”

EDIT: The response to this post has been pretty overwhelming. So I'm considering starting a project to teach people everything helped me get to where I am step-by-step. Here's the interest form: https://lnkd.in/dRvqDrc

Esther Crawford was the Chief Executive of Twitter Payments.

A few months ago, someone on her team tweeted this picture.

She commented saying sometimes you need to sleep where you work to make deadlines.

This week she was fired abruptly.

No matter how great you are, you are ultimately disposable.

So while you do your best work, don’t forget to prioritize yourself and your well-being.

Live for yourself.

One of my reps created a cold-call technique that was almost flawless.

It helped them book more than 23 meetings in just a few days.

So I asked them to create a template so we could share it with the rest of the team.

In the past, I had worked for managers who acted like they created everything they shared.

It always made the team feel like they weren't being rewarded for their ideas - which led to less creativity.

So during our next team meeting, they spent the first 10 minutes teaching their teammates this unique tactic.

And in front of her colleagues, I praised them for thinking outside the box and the team showed their gratitude for it!

When other team leads or reps asked why we were getting such great results, I told them this rep had created a technique that was working.

Then shared the reps template with them.

As a leader, it's not your job to be the smartest person in every room.

It's your job to bring the best out of people and make sure they get rewarded.

The best leaders give you credit for your work - even if you're not in the room.

My CEO gave me a $10,000 raise a month into my first job

This was back in 2016.

I used to come to work an hour early to talk with him and learn about the business.

He would teach me about raising funds, bookkeeping and investing.

There were countless stories he shared about how he almost lost his business and how people had stolen from him, and what to look for in great employees.

One day during our 1-on-1, I brought up the fact that I was struggling to make ends meet but that I would just out in more work to make more sales.

I was only a month in so I wasn’t making any commission.

An hour later, he called me into his office and said “I’m increasing your base salary by $10,000 effective immediately.”

I don’t know if I fully deserved that raise but once I realized how much my boss cared, I poured my heart and soul into his company. I was already working hard, but it made me want to work harder.

It boosted my confidence and I will always be grateful for his belief in me.

We need more leaders with big hearts who are willing to make big bets on PEOPLE; not just big ideas.

#internationalstudents #ottawa #jobs #leadership

One of my friends is still on stress leave after 4 months.

His team lead actively made his life a living hell for over a year until he almost broke.

I remember every terrible manager I have had - just as vividly as I remember every great one.

The trauma attached to some of those experiences is very real.

It's not just work that gets affected.

A bad manager can literally ruin your life.

But working for a great leader can change your life forever.

My wife changed jobs 6 times in 6 years.

She went from working as a nurse to being a top-performing Account Executive and thrived in each role.

On one hand, she was looking for a career that truly brought her fulfillment.

On the other hand, her compensation increased by over 60% by simply refusing to settle.

Stop buying into the myth that job hopping will hurt your career.

Being stagnant is what will kill your potential.

That doesn't mean you should change jobs every 6-12 months!

It means you should relentlessly pursue what you want until you find it.

Life is too short to hate what you do while getting paid less than you deserve.

Job hopping isn’t going to hurt your career.

It’s going to accelerate your income.

I worked for a company that used to use the word “family”.

On my 3rd week there, they laid of 20% of staff - I survived.

That was the last time I associated the word family with a company.

This is a much better definition.

This is a reminder.

Stop living for the approval of other people.

If you try to do something great, they will judge you.

If you do nothing, they will judge you.

If you fail, they will judge you.

And if you succeed, they will still judge you.

So just do what makes you happy.

Last year, one of my reps was getting criticized in a meeting.

They were not doing well that quarter.

But since they weren't present to defend themselves, I stood up for them during the meeting.

I truly believed this rep was great and was just going through a rough patch.

And after the call, I set up a meeting with the rep where I laid it out simply:

1. People are talking about you - you need to prove them wrong
2. Let your activity and results do the talking for you
3. I believe in you and I let the team know that.

They finished that quarter at 130% of their quota.

This is something I learned from one of my favourite bosses.

The best managers always have your back.

2022: Klarna replaces 700 employees with AI

2023: Klarna lays of 40% of their employees

2025: Klarna announces $136 million loss because people aren't paying back loans (shocking)

2025: Klarna has lost $40 billion in company value and CEO wants to rehire humans.

Apparently AI agents failed to meet expectations in delivering effective customer service.

Turns out AI can't do everything and replace everyone.

Stop putting profits over people.

I remember telling my boss at my last company that I got an offer at Shopify in 2020.

It was a 33% increase on the base salary alone and I knew he couldn’t match it.

He literally celebrated with me and then acted as my reference for the new job.

While I was still his employee!

I could tell that he was genuinely happy for me and I never forgot that.

Of course he was sad to see me go and I was sad to be leaving him.

But he knew I had so many family responsibilities and that I wanted to buy my first home.

We talked about it in 1:1s often.

I needed the higher income for that and he helped me get there.

We’re still great friends till this day and he was one of the first mentors for 3Skills.

That’s what true leadership looks like.
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I'll be sharing more stories like this on my newsletter next week: https://lnkd.in/eVsJseP6

6 years ago, I married my business partner. \n\nWe were running a clothing line together at the time. \n\nEven though that business failed miserably, she never stopped believing in it. \n\nAnd at 24, we decided to get married and sunk everything we had into making it happen. \n\nThe first year was unbelievably rough. \n\nWe didn’t even have our own apartment for the first 3 months of our marriage. \n\nI still remember having to borrow $150 for groceries from my sister a few months after our wedding. \n\nThat was the day we decided that we would get serious about building the life we dreamed of. \n\n6 years later, we’ve done just that and we get to take care of our families while traveling the world. \n\nWho you choose to spend your life with matters more than any other decision you will make. \n\nSo choose wisely. \n\nThanks for sticking by my side Brunette Katombe \n\nHappy 6 year anniversary.

My base salary progression since 2016:

Year 1: 0% increase (New job)
Year 2: 11% increase (New job)
Year 3: 20% increase (Same job)
Year 4: 33% increase (New Job)
Year 5: 3% increase (Same Job)
Year 6: 73% increase (New Job)

Sharing for transparency again.

Invest in yourself but don’t forget to collect on the other side.

As your value increases, so should your paycheck.

Stop settling for symbolic gestures.

Go where you are valued.

I bought my mom a car last year.

It's a promise I made to her when I was 14 because I knew she loved cars.

And it was one of the most fulfilling moments of my entire life.

Many of my friends think I'm passionate about LinkedIn - but they're wrong.

This is what I'm really passionate about:

- Taking good care of my mom
- Paying my brother's college tuition
- Taking my dad to watch Arsenal live
- Traveling around Europe with my sister

Getting the most out of life with the people I love the most.

A job is a means to an end.

So is creating a personal brand.

And so is building a profitable business.

Don't get carried away comparing yourself to people trying to look successful.

Write down your own definition of success.

Then pursue it relentlessly with everything you've got.

I promise that it will be worth it.

For years, I used to commute 1 hour each way to work.

I would be up at 6am to get ready.

Leave the house at 7am to catch the bus.

Arrive at work at 8am and start my day.

Then head out of the office at 6pm on most days.

Another hour back to the apartment - just in time for dinner.

And then the day was pretty much gone.

When I started working remotely, I realized how much of my life was being spent commuting.

All of a sudden I had that time to reallocate to my wife, family and friends.

And if I wanted to get more work done, I would just open my laptop and execute.

Working remote didn't just make me more productive.

It gave me my life back.

LinkedIn changed my life.

June 2020: I wrote a post that went viral

May 2021: Hit 10,000 followers & $150k in revenue

August 2022: Passed 100,000 followers & 100M impressions

June 2023: Quit my job at Shopify to build more businesses online

July 2024: Surpassed $1.5m in revenue and over 220M impressions

Yesterday I finally got to visit the LinkedIn office in London, UK.

Finally met my Creator Manager Dani Markovits in person.

We exchanged a ton of ideas and learnings from both sides over coffee.

And by the end of our conversation, two things were abundantly clear:

1. The opportunity on LinkedIn is still massive

98% of people are still consuming & only 2% produce content

2. It's still so early to get in on the action.

Someone compared creating on Linkedin today to creating on YouTube in 2006.

It's that early!

Excited about what we're working on next!

2025 is going to be an insane year.

—-
P.s. I’ve gotten a lot of messages from people who want to replicate what I’ve done. I’m hosting a FREE webinar on October 31st. Sign up here: https://bit.ly/3YG0CQ7

I didn't quit my job until my business revenue was double my salary.

Because I was terrified that I would ruin my life without the safety net of a pay check.

Every time I heard someone say they are “going all in“, I get scared for them.

Entrepreneurship is the most unpredictable revenue stream - especially at the beginning.

One small mistake, one new piece of technology, one bad customer can put your whole business at risk.

So instead of quitting your job to become a full-time entrepreneur...

Treat your salary as startup capital and build your own thing from 5-9 and during the weekend.

Take your time, build an emergency fund and build a sustainable business.

Go big of go home is how so many people end up at home.

Start small and move quick.

Stop over-explaining your price.

Once you become the best at what you do, own it!

That’s your imposter syndrome kicking in.

You have spent years, maybe even decades, mastering what you do.

You have then built systems that create repeatable results.

And you have enough testimonials to prove that you are not a fraud.

So stop talking after you share what people have to invest to work with you.

You deserve what you’re asking for.

My friend recently turned down a job.

Because the job title wasn’t senior enough for him.

Even though the pay was good.

I just went through the job description and it perfectly aligns with what he’s passionate about.

Don’t make the mistake of prioritizing your position over your purpose.

My co-founder & I built our business from $0 to $1 million in 12 months.

Her first 2 pay checks were on my credit card.

Because we had no revenue.

She had already quit her C-level role to join me.

Bu we had no clue what we were going to build yet.

Our first experiment failed woefully - $1k in revenue after 8 weeks of building.

But our second experiment was a hit - $120,000 in revenue in the 60 days.

Till today, I'm still grateful that she was crazy enough to believe we could actually build something from scratch.

You don't need a massive team to be successful.

You need believers who are willing to put in the work.

Find the right people and you'll build a great business.