My 5 Favourite Business Podcasts

My Overcast Playlist

These days I can’t fold laundry or clean my kitchen without a podcast playing in my ear.

I listen to a variety of podcasts but my go-to are business ones because they de-mystify real world complexities like inflation, supply chain or marketing (also, I’m a nerd).

If you’re looking to add a business podcast to your playlist, these are some of the best ones out there.

Acquired

The Premise

Acquired is hosted by two very smart tech investors and business geeks named David Rosenthal and Ben Gilbert.

Each episode is dedicated to a specific company and sometimes features interesting guests like CEOs and VCs.

Episodes are VERY long and well suited to a Sunday morning chore marathon or a long bike ride.

Who is it for?

David and Ben usually dig deep into their subject matter, often scouring all publicly available material for research.

So anyone who enjoys an in-depth look at a company (or an industry) can learn a lot from their thorough takes.

What do I love about it?

I love that both hosts are brilliant analysts and researchers.

Each time I listen to an episode, I gain a full understanding of not only the featured companies but also the key players involved.

I also love that they cover a wide range of Industries. Season 8, for example, featured both Berkshire Hathaway and Ethereum. I can’t think of two companies less alike, founded by two humans who couldn’t be more different!

Finally, both hosts are excellent story tellers and their chemistry make even the most mundane detail interesting to hear. Also, David Rosenthal has the most radio friendly, soothing voice!

Favourite Episode

I LOVED all 9+ hours on Berkshire Hathaway Part 1, Part 2 and Part 3 and the legend of Warren Buffet. To the point where I still drop random Warren Buffet anecdotes in conversations as if I know the guy.

The All-In Podcast

The Premise:

Easiest way to describe All-In is four billionaire best friends – J-Cal, Chamath, Sacks and Friedberg talk about business, tech, science and politics for a mesmerizing 90 minutes.

Who is it for?

Anyone interested in business or technology or is a fan of one of the hosts would love this podcast (chances are you’re already listening).

Why I love it?

I tuned into the first episode during Covid and when finished I felt more hopeful than ever before.

The four hosts are some of the most brilliant, forthcoming and accomplished people out there. As long time entrepreneurs and investors, they approach every problem with a series of solutions.

Their chemistry is undeniable and their world views – especially when they disagree – are nuanced. I feel better informed about the world for having listened to them.

Finally, I immediately become besties with anyone who loves All-In (because most listeners are action oriented, critical thinkers), so it’s a great way to make new friends!

Favourite Episode

They are ALL great. This is one of the best tech/business podcasts out there.

I had a chance to attend the first (and sadly last) All-In Summit this year and it was exhilarating.

If anything I wrote above resonates, then immediately go listen to all the episodes… like RIGHT NOW.

Gary Vee Audio Experience

The Premise:

Is there anyone out there who doesn’t know Gary Vee (a.k.a. Gary Vaynerchuk)?

I don’t remember when I started listening to Gary Vee. But it went something like this:

First, I thought he was obnoxious. Then, I thought maybe he is on to something. Finally, I thought the man was a genius! And today I follow him on all social platforms and periodically show his videos to my kids.

Who is it for?

Gary Vee is an acquired taste. But anyone interested in marketing or becoming a content creator will find Gary Vee highly inspiring.

Why I love it?

Gary Vee’s podcast is not polished or super structured. BUT Gary is a force of nature – super inspirational with crazy high energy.

If I am ever feeling low on a cold, winter morning, I listen to Gary pumping positive energy into the world and I feel better!

Favourite Episode

I loved Gary’s “Tea with Gary Vee” live episodes during the lockdown. But the one where Gary spoke with Sam Parr, was a standout episode. They had such an honest conversation about their origin stories and how both felt out of place amongst the Silicon Valley crowd due to their more humble beginnings.

My First Million

The Premise

Speaking of Sam Parr, My First Million is a podcast hosted by Sam and Shaan Puri. They deliver on the title and talk about ways to become financially successful.

They are tech adjacent but have all types of business people come through the podcast from influencers to factory owners.

Who is it for?

Sam and Shaan unabashedly give off the “bro” energy.

They are hyper intelligent and seem like awesome dudes but if dumb jokes and the bro vibe is a turn-off, then My First Million will quickly become insufferable.

But it’s GREAT for younger people looking to go from $0 to millionaire. Their advice is so specific that if someone WANTED to be a millionaire and was OK with hard work and learning new things, they probably could get there following Sam and Shaan’s playbook.

Why I love it?

I find Sam and Shaan to be absolutely hilarious.

They are highly successful and super smart product/business guys. They are also dead serious about making money.

Yet, there is a levity and irreverence to how they approach everything that is just fun.

I learned a ridiculous amount of practical advice on how to start/grow a business from these guys while genuinely laughing out loud at their silliness.

Favourite Episode:

My two favourite episodes were one with Dharmesh Shah (of Hubspot) and with Neil Patel.

This Week in Startup

The Premise

This Week in Startup (TWiSt) is a daily podcast hosted by Jason Calacanis and (recently joined) Molly Wood. As the name suggest, the show predominantly hosts founders of emerging and established startups.

But it also features interviews with fascinating people: from journalists like John Carreyrou to authors like Rory Sutherland.

Production value of TWiSt is super tight. It’s one of the best sounding and well paced podcasts out there. I love the professionalism and attention to details.

Who is it for?

I think TWiSt can be interesting for a wide range of people. Anyone who likes Tech and business can learn a lot from this podcast. The episodes usually start with a news segment and I enjoy getting my weekly dose of tech/business/streaming news from the show with some good analysis.

Why I love it?

I am a big J-Cal fan.

My entire family knows him by voice due to All-In and TWiSt often playing in the background.

I met him in person at the All-In Summit and I listened to the first episode of This Week in Start Up when I was on Mat Leave with my first kid back in 2011!

So it’s a LONG term & personal fandom.

Picture of me meeting J-Cal in Miami

Favourite Episode:

I have WAY too many favourite episodes to list.

But one episode that I listened to multiple times was a 2019 conversation with Twilio founder Jeff Lawson.

I also loved every episode with Bill Gurley and Keith Rabois.

Let me know if you are listening to any of these podcasts already! I am always open to discuss an episode or watching together when a new one drops!

My Own Personal Career Pivot – Part 3

My First Fintech Book

In part 1, I wrote about the early days of my career – starting at BMO and then at TD. 

In Part 2, I wrote about finding out what was next and reaching my immediate financial
goals.

In this post I’ll describe the steps I took to leave the corporate world and join a start-up and end with my evaluation process.

By the end of 2021, I had set up a secondary revenue stream via my condo and bought the house I planned to live in for at least the next decade. I also sold my old house for more than expected and used the extra money to set up an emergency fund and improve my savings.

I was ready to focus  on my career and take some risks.

In part 2, I wrote about exploring consulting to earn extra income and expand my skillset. During that exploration period, I became deeply familiar with two companies.

The first company provided recreation services to children, looking to spin up a tech arm to rebuild their software. And the second company was a fintech start up with a payment and communication platform, branching out to work with larger NFPs.

Both companies had innovative, hardworking founders with an interesting vision for the future and a history of success. However, it was clear to me that I was a better “fit” for the fintech company – even compared to what I was doing at the Bank.

That fintech company was Pllenty, where I currently work!

I had access to inner workings of both companies through my personal network. And the more I learned about Pllenty, the more I felt this COULD be the place for me!

So, at a 1-1 with my contact at Pllenty, I expressed my interest in working with them “one day”. I didn’t know exactly when that “one day” would be. But I followed up regularly with my contact throughout the next months to keep my interest top of mind.

The more I learned about Pllenty and the payments, the more I liked what I was learning and wanted to learn more. For example, after having an in-depth conversation with my contact about the payments space, I joined a Fintech book club online and bought my first book on payments (Anatomy of the Swipe). 

However, when I received the call from my Pllenty contact winter of 2022 for a potential job opportunity, I totally wasn’t ready!

At TD, I had an awesome salary, a fabulous boss, a leadership position in an interesting and career defining program rolling out Salesforce. While I wanted to take a career risk, I didn’t expect to cross that bridge for at least another 18 months!

I had been gathering intel on Pllenty for over three years, so I HAD to explore this  opportunity now that it had presented itself.

I kicked off the exploration process with some real talk with my Pllenty contact. I asked probing questions about what was working and what was not working. I asked about the team and who they were. I asked about the history of the company and the vision for the future.

Then, I put myself forward for a conversation with the President & COO of Pllenty. He was an acquaintance and already a person I admired and respected. But in our 1-1 I was blown away by how he was able to walk me through the past, present and future of the company in a 45-minute conversation. For me, this was a sign of a leader who wanted to go somewhere, and I felt excited to be part of the journey.

After I felt “the feeling”, the rest was an exercise in satisfying the rational parts of me and identifying blind spots.

I had a solid career trajectory at TD but at Pllenty I had a tremendous chance to grow as a leader more immediately.

TD provided me with stability and predictability, but Pllenty will provide exposure to all parts of a business –  from the early sales calls to discussions on infrastructure.

I would be more vulnerable at a start-up if things didn’t work-out, but I also had a chance to be participate in tremendous upsides if they did.

As part of the blind spot evaluation, I had an hour-long conversation with my smartest and most brutally honest friend with a tech background and whatever downsides they could come up with didn’t sound all that bad.

I am not privy to what the conversations were like on the Pllenty side. But both parties saw a fit, took a chance, and I was offered a job!

I gave my start date as April 18th  to allow me 3 weeks of notice at TD, plus two weeks off to decompress.

That was now 3.5 months ago, and I haven’t looked back! It has been an intense ride so far and I enjoyed almost every moment of it.

Looking back, I can summarize my evaluation process (whether to stay at TD or join Pllenty) from three angles:

1.    Financial

My medium-term financial goals such as buying real estate and a substantial emergency fund were all met before leaving the Bank. If I still had such financial goals, I may have tried deferring the move for 1 or 2 more years. 

I also focused on adequate cash-flow vs total compensation to ensure we could maintain our current lifestyle (e.g., equity vs salary). Taking a big pay cut in exchange for more equity, for example, would not have worked for me.

Finally, I looked 5-10 years ahead and saw which would bring me more upsides. I felt that while steady ladder climbing at the bank would be great, I had a higher chance of being part of something more rewarding in the long term by joining Pllenty.

2. Flexibility 

Pllenty offered more flexibility of working hours compared to the bank.

Most of my meetings at Pllenty are concentrated between the hours of 10am and 4pm, Tuesday to Thursday. So, by working a few hours on the weekend, I can significantly improve the flexibility of my days outside of those core hours.

I also influence the efficiency at Pllenty, as we are a small team. So I feel more confident that I can continually improve efficiency over time in ways impossible within a complex corporation.

3. Growth

Finally, the nature of a start-up offers tremendous opportunity for growth. Any problem that occurs in the company, we need to solve ourselves – there is no X department (looking at you TRMIS) we can do an intake with. Additionally, origin of every mistake is painfully obvious – so there is no where to hide either.

I find that I have learned something new literally every day since I started, and I have not scratched the surface of all there is to learn.

That’s it! I hope you enjoyed my three part journey from a Corporate lifer to a start-up “newb”.

Thanks so much for reading, please keep reaching out with your comments and questions.

My own Personal Career Pivot – Part 2

My dream backyard

In part 1, I wrote about the early days of my career – starting at BMO and then at TD. In this post I’ll get into the critical three years where I achieved my financial goals and started thinking about what was next.

In 2018 I was 37, my sons were out of the baby stage, my mortgage was well under $100K and I  began to wonder what the next stage of my life will look like.

I started simply by listing out what I wanted to do more of: writing, travelling, and meeting new people. And I analyzed how much money I needed to support a
comfortable lifestyle for myself and the family.

I gave myself three years (or until 2021) to figure out how I was going to get there. The illusive goal was to make more money while also having more time to write, travel and meet new people.

First, I explored increasing my income by doing 10 hours of consulting work a month, in the evenings and weekends. I set my rate at $75/hr and started asking friends if their companies needed some help.

I quickly learned that working longer hours for more money aligned poorly with my overall goal.

Also, once I started a project with a company, 10 hours/week of sporadic work was not enough time to do a good job.

Finally, TD had policies against moonlighting, and I wasn’t sure I wanted this extra money enough to deal with the “paperwork”.

So, I went for door #2: that is get paid more for my 9-5.

Once I made the decision, it was a relatively easy process. I applied to several internal positions and then landed a new role at TD that paid more, with a higher bonus and more earning potential.

In the meantime, I kicked off my pvot40 blog to fulfill my writing aspirations and interview interesting people. I also started booking more trips to satisfy the travelling dream.

Things were progressing well. By early 2020, I had a better salary, tripled the number of trips and written several well received articles on my blog.

Then the COVID19 pandemic hit! ALL my plans had to stop.

The kids needed my attention with virtual school, traveling was not possible, and I was just too busy and anxious to write.

However, as the chaos of the lockdown settled, I noticed that our expenses were down drastically: no daycare, no travel plans, no dining out or even driving. In parallel, the Toronto real estate market was taking a temporary nosedive.

I realized that one way I can make money without working longer hours was to
own Real Estate!

In fall of 2020, I engaged our Real Estate agent (the best one in the city), and by January 2021 we had a beautiful condo in downtown Toronto. It was a fantastic deal – the condo was priced $100K lower than even today and we snagged a 5-year fixed mortgage rate of 1.99% thanks to my AMAZING broker.

The condo increased our household income by almost 30K a year (our expenses also increased, but in a few years the condo will be cash-flow positive while raising our borrowing powers and net-worth).

But with travel plans still mostly on hold and lockdowns continuing longer than expected, I was aching for more outdoor space that my little townhouse was sorely lacking.

A bigger house meant bigger expenses! And it led me to go for round two of
job hunts in just 3 years. I lucked out and landed a new job March of 2021, with
a substantial increase in both salary and bonuses.

Armed with my new salary, I bought a detached, mid-century house, with an
amazing outdoor space and a fully finished basement for the kids to roam
free on September 1st, 2021.

I also happen to sell my old house a few weeks after purchasing the new house and we benefitted greatly from this minor arbitrage (in a rising market) because the sale of our house exceeded ALL my wildest expectations! And we were able to use the mini windfall to establish a good emergency fund, add to the RRSP, pay off consumer debts and set aside money for future house repairs.

By the end of 2021, we were in a great place financially.

I looked at our household budget spreadsheet and the projected surplus at the end of 2022 looked better than ever before!

Yet, I was not travelling more or writing more or meeting new people. And being on a complex program, with 100+ people and executive scrutiny at work meant almost non-stop online meetings.

I was also seeing that all my additional income was likely go into buying more stuff: more expensive restaurants; Smythe instead of discount Banana Republic; luxury car instead of our 2010 RAV4.

I was happy but not 100% aligned with where I wanted to be…

Stay tuned for part III.

My Own Personal Career Pivot – Part 1

In spring, I resigned from my corporate job after 15 years to start a role in a startup.

Over the next few posts, I am going to talk about this pivot and give updates on what I am learning from this new “world”.

First a little story about my career so far.

I started my first corporate job at Bank of Montreal (BMO) in 2007 as a Senior Business Analyst with a salary of $60,000.

Money had never been a big motivator for me and in 2007 I was married, living in an adorable apartment and a respectable job that paid well was more than enough to make me happy.

BMO was a blast for me.

We were several years past the dot com crash and at the height of the bubble that eventually led to the 2008 financial crisis.

It was a fantastic time to be at a financial institution. I was part of a cohort of New Grads in Capital Markets Tech. And we were treated like the “best of the best” and we were a group of fun-loving young people – smart, ambitious, energetic with a good future.

We were unencumbered, loved life, saw corporate success as a worthwhile ambition and loved being part of the Bay Street glamour.

I am friends with many of my former BMO colleagues 15 years later. I still adore every one of them and rejoice watching them blossom into their best selves (often on LinkedIn).

The early years went by quickly amidst a haze of good times.

There were poker nights, happy hours, and club nights.

There were tacos and margaritas and deep conversations about life, career, nature of humanity.

There were inside jokes and being squished in the backseat of a cab illegally with too many people.

There was Beatles Rock Band.

It all changed when I had a baby.

At 28, I was the youngest one of my peers to have a baby. The first maternity leave was an excruciating adjustment (but I survived and eventually thrived). But when I returned from my maternity leave, everything felt different.

Most of my friends had moved on to a different role or moved into senior positions, and I was now a mom who couldn’t go anywhere.

There was already a cohort of “new grads” who saw me as a boss type – a woman in her 30s with a child and a grown-up life.

So, I left it all behind and moved to TD and joined its insurance group. I spent the next 9 years of my life there in a variety of positions.

TD gave me some wonderful friendships that I still hold dear, but I never felt that sense of community I did at BMO. (I realize with some sadness that what I experienced at BMO was a product of my age and environment and I am unlikely to get there at work ever again.)

Still, there were lunches and pubs and at least one house party where there was dancing on a kitchen countertop.

The corporate environment, especially TD, gave me an enormous sense of stability.

It allowed me to make good money (salary grew at a steady pace) while having a manageable workload as I raised my children and dealt with my father’s cancer.

TD corporate culture was polite and organized. And I am so grateful for everything I had because of it.

Even as I write this, it is obvious that much more than the work, what made my corporate career satisfying were the friendships.

So in 2018, as I approached 40, I realized I could not picture myself climbing the corporate ladder for the next 20 years of my life. I needed something more.

Thus, I kicked off a major career pivot without even realizing it…

Stay tuned for Part II

Lessons Learned from Buying an Investment Property 

Mid-January I became the owner of my second ever property.

I bought a house back in 2008, a little Townhouse where I grew my family. And when I saw that our mortgage was about to finish, I thought why not get a new mortgage!

I like mortgages. They are a big pile of money a lender lends you, with a low interest rate (at least these days). In return you get an asset that increases in value and brings in some rental income!

Let me share with you my adventures in real estate and some lessons I have learned along the way.

The Whys

A very clever fellow named James Clear once Tweeted “Instead of working toward retirement, work toward your ideal lifestyle. There is usually a path to get there in a few years instead of a few decades.”

My ideal lifestyle always included a house in the Toronto Beaches neighborhood and a condo downtown.

Yet, considering how hot the downtown market has been the past decade, a downtown condo was not a realistic purchase for us. My value conscious, immigrant mind, could not justify paying $600K+ for a one bedroom in Liberty Village.

So, focus was on the house at the beaches. That was tough but achievable. We had good family incomes; we were lucky to buy the first house right before the R/E frenzy. And our most expensive years, two little ones in daycare, were behind us.

But buying a new house was not supposed to be for another few years! The kids were still in part-time daycare and we had grand plans to travel the world. I expected to move into our Beaches dream house when my older son was in high-school and that was still over 5 years away.

Then Covid happened.

Day care, vacations and travelling all became a thing of the past. We stopped going out. We stopped spending money. And with the mortgage nearly complete, an investment property seemed like a good place to funnel the savings.

Assembling the Team

Key to all successful projects (missions or heists) lies in the assembly of the team. We kicked off our investment property project by engaging a real estate agent.

I find Real Estate agents are often unusually beautiful, impeccably stylish and highly driven (shout out to my mother-in-law).  And our agent, Tori Nguyen, turned out to be one of the most beautiful, stylish and driven in the city (follow her on IG)!

Tori brought a wealth of Real Estate experience to the table. She knew all about renovations, noticed details we missed and was a master at seller psychology. She was also super generous, hard working and always prepared. Attending showings, even when the city was in lockdown, was easy and painless thanks to her.

Tori was just persuasive enough to help us overcome the fear of making big decisions. She helped us by asking questions, being totally honest, moving quickly, pivoting when needed and by being available.

Second member of the project team was my brilliant friend Quyen Taylor, who is a mortgage broker. This woman knew her mortgage products inside out and without her expert advice I doubt that we would have gotten so far.

Quyen’s real estate and financing lens is unique. She came to us with financing options normally unbeknownst to a layperson.

An independent mortgage broker is helpful for all buyers but can be especially invaluable for a second property or exceptional cases.

Finally, I downloaded an awesome little app called HouseSigma to browse real estate.

HouseSigma shows the listing, provides high level market analysis and provides past listings on the property, including leases.

The user interface is delightful and easy to navigate. If you are browsing real estate in the Ontario market, I recommend this app.

The Homework

Next step in the buying process was understanding our financial current state.

Buying a house 12 years ago was so much simpler as we had no money and only two bank accounts. Now we are a mess of checking accounts, savings accounts, RRSPs and Credit Cards and digging through all of that was not fun!

On the bright side, reviewing our finances did motivate me to get my RRSPs organized, so that was a bonus!

Armed with all our financial info, Quyen was able to strategize the best way to fund our new purchase. She showed us how we can pay off our current mortgage six months earlier than expected.  And how we can use a combination of our home equity line of credit and savings to manage the down payment and closing costs.

On our side we created a spreadsheet with a detailed breakdown of our income and expenses and added easy ways to evaluate the affordability and profitability of potential properties.

We set an absolute maximum budget of $750,000 based on what we could afford comfortably.

The Search

Initially it made little sense to buy an investment property that did not generate a profit. And as homes in Toronto were hella expensive, Tori suggested we look to Durham region to find a “deal”. We investigated purchasing a small detached house, turning it to a duplex and collecting two rents.

Oshawa seemed perfect. It was a developing town with a bright future. Houses were reasonably priced. It was still a short commute from Toronto. As a bonus, Tori was experienced in the rental market in Oshawa and we trusted her judgment.

However, shortly after our first evening of showings, the Oshawa market skyrocketed. Properties started selling for $200K over asking and even before renos they were already outside of the budget.  

Oshawa market was too hot, and the pressure showed me that I was not ready to bet it all on Oshawa. Yes, it had good potential to make money, but the cost of buying, renovating and managing the rentals was still high. A house in Oshawa brought nothing but the possibility of a positive cashflow. And it really did not seem enough.

I was ready to wait.

But as the Oshawa market heated up, the downtown Condo market was cooling down. Inventory was piling up as people exited the city. Rental demand for small condos were dwindling with everyone working from home and sellers were ready to offload.

The more we looked at the downtown condos, the more it felt right.

Sure, it would not get us the positive cashflow that two units in Oshawa would, but it would be a step towards our ideal lifestyle. A condo at the heart of Toronto would be an investment in our future. I found it was easier to decide when the value was more than just monetary.

We narrowed our search based on a few criteria:

  • Close to subway
  • New building (under 7 years)
  • Low monthly maintenance
  • Has a parking spot, a good-sized bedroom, more than one room and a balcony.

We landed on two possibilities: first was on Richmond, few blocks east of Yonge. This condo was a bit cheaper, a bit bigger. But with no balcony and the location was still developing.

The second was on Adelaide, near John, it was a smaller unit, higher floor, more expensive but with a beautiful balcony and the most perfect location.

Now I must pause to express my love of Adelaide street.

Adelaide street, from Church to Spadina, is my downtown Toronto. Adelaide is humble and unpretentious. It does not have the edge and angst of Queen West, nor does it have the corporate coldness of King. Adelaide is full of heart, charm and innovation and merely blocks away from everything important.  

Once we saw the location and the building, decision was super easy. I wanted it.

I could see myself living there happily if I were alone. And even if we made little in rent, it was worth it to own a piece of a street that I love.

The Offer & Aftermath

Sellers were asking for $689,000. With Tori’s expertise, we put in an offer, and after some minor negotiations we settled on $675,000 with condo fees of ~$480 a month.

I felt good about it.

We asked for a 4-week closing period to get everything in order. Selected First National as our lender. Engaged a lawyer and an appraiser etc. Now we are mere weeks away from getting our keys.

Making the Decision

Looking back, I basically used three questions to make my decision.

First question was Can we afford it? Not just in the best-case scenario but under some stress.

I am naturally risk averse and for me this was the most important question (may not be for everyone).

We evaluated our incomes, expenses, debt repayment and additional expenses of owning the condo. Then we ran our calculations through three possible scenarios:

1a. Can we afford it if we did NOT have a tenant for a period of time?

1b. Can we afford it if we temporarily became a one income household?

1c. Can we afford it If 1 & 2 happened at the same time?

With our primary mortgage paid off, the answer to all three question was yes but with various degrees of belt tightening.

Second question was Is the property worth the price?

We relied on Tori’s expert judgment to determine a good price for the condo. An appraisal following our purchase concurred with the price we paid.

We additionally looked at historical price of similar condos in the same building. We tried to envision the value of the amenities in a post-Covid world. We invested in features we felt were valuable, like a bigger bedroom, a giant balcony and a parking space.  We chose a location that was most likely to recover quickly (compared to other downtown pockets).

Overall, we bet on the city returning to pre-Covid vibrancy eventually and that the property will appreciate.

And the final question was am I getting something beyond just money when investing in this property?

Whenever I envisioned my future, I always saw a house in the Beaches and a condo downtown. And this little condo fulfilled a part of that vision. When I think of future moments in this place, even if we rent it out for the next few years, it makes me smile.

I can see one or both of the boys living in that condo when they go to school or start their first jobs.

I can see date nights or girls nights downtown ending with cocktails at the condo.

I find myself already call the building, our building. It feels right.

Lessons Learned

In summary, here are the key lessons I learned from the process of buying a second property:

  • You have thousands of options available in a place like the GTA. Take time to dream about your future and explore different options. Let your imagination guide you to what is possible and eventually you’ll land on something that fits.
  • When ready to start the purchase process, assemble a good team first. I recommend an experienced real estate agent and a knowledgeable mortgage broker, especially for an investment property.
  • Know what you can afford. Spend the time to dig into your own finances and be hyper realistic about your budget. When buying real estate, going too cheap is not necessarily a good idea. But maxing out your budget can be even worse.
  • Be reasonable with your fears. When evaluating your worst-case scenario, try not to think of catastrophes. The only decision when faced with a catastrophe is to do nothing. Conversely, you will own this property for a few years, so account for realistic set backs.
  • Trust the experts to guide you. Be very selective when assembling your team of experts, but after that trust their judgment and ask for recommendations. If you feel the urge to second guess your expert, ask a lot of questions instead. It is very likely they know something you don’t.
  • Give yourself time and be patient. It can take months to find the right property.
  • But decide quickly when you find something you want. All the preparation you have done up front should help because real estate moves quickly – be decisive and stick to your criteria.
  • Make sure your team compliments your blind spots. I am naturally very risk averse, so I appreciated a real estate agent who was bolder. On the flipside, I knew little about the mortgage world, so Quyen’s vast knowledge of mortgage products filled me with comfort.
  • Aim for the best you can afford. Think in dimensions of what can you comfortably afford versus what is the best you can afford. Buying a slightly cheaper property in a shittier neighborhood or without the things you truly value is probably not that great. You get what you pay for.
  • Finally, buying an investment property can be exciting and fun. Try to enjoy the process and learn along the way.

Looking back at 2020

I stopped writing in this blog mid-way through 2020. I felt my brain was saturated.

Days felt relentless – job, kids, family, worry, missing loved ones – and evenings were tiring, doom-scrolling Twitter. Every Covid morning kicked off a series of tasks to be completed, last one being sleep.

One downside of kids always at home is every thought can be interrupted and the only way to avoid frustration is to not have expectations.

Turns out, I did not train myself to be creative without a lot of mental space. I learned in 2020 that I can be busy and productive, but I am shit at being busy and creative. I am hoping to be better, more aligned with my goals, in 2021.

Our collective lives are in flux and these changes will continue. And even when Covid stabilizes, our fears may not. Experts are already worried about the second order effects of the pandemic and lockdown.

We have no choice but to move forward. Continue to work on self-actualization even as the base of the pyramid shakes violently.

Anyway, allow me to kick off 2021 with a self-indulgent, self-reflective post. I hope you will find something familiar in the joys and learnings of an extraordinary year lived by an ordinary person.

The Kids

What I will cherish most about 2020 are the presence of my children. My adorable and challenging little humans were with me nearly every moment of 2020.

Once maternity leave was over, I was OK with not being around them always as I had my own life to live. But Covid happened and I had a whole year of having them near me most of the day.

Children start their lives being a part of our bodies and few boundaries exist between the parent and the baby in the beginning. Then with each difficult day forward, they grow a little bit apart from us.

This separation continues until one day they exist completely as an individual both physically and mentally. My kids are rapidly entering that phase where they are entirely separate from me.

Covid and quarantine gave me extra time with these little humans. In the beginning I was a witness to their first tooth and first step but in 2020 I was able to watch them discover the joys of livestreaming, inventing hybrid dinosaurs, and learning how to read.

What a gift that has been. I do not mean to sugar coat the exhaustion that comes with trying to manage work, children and household without any external support but when I look back on the year, all I feel is grateful for my time with the kids.

Joys of Social Media

I finally discovered the joys of social media in 2020. I am into technology, always have been. But social media was this annoying thing in the background for me.

Yet, when my external, physical world closed down around me due to Covid, my internal world opened up via Twitter, IG, blogging, TikTok and Clubhouse.

I made some new friends on all these platforms. They are all strangers in the real sense, but for a year now we have shared small slices of our lives with each other.  

Pre-Covid I limited my friends circle to those within my physical orbit, but social media opened up possibilities of being friends with people who are very far away.

In the past I was skeptical about online friendships and over valued in-person interactions and interpersonal intimacy. But I was wrong.

Sharing anything, even Memes, over a period can lead to a kind of friendship. And these friendships can be even more satisfying than some “real-life” friendships.  

As my real world shrank to the four walls of my home, it was cathartic to open myself up to everywhere else. The world is full of interesting people and ideas and it can be incredible to connect to them.

I thank 2020 for that realization.

Buying a Condo

Confinement cut down our spending dramatically. I am not berating myself for it, I work so I do not have to worry about where the money goes.

Still it was shocking to see money accumulating in the checking account for a change. With the additional funds and the bleak reality of staying at home (read no big vacation), we indulged in buying a small condo on one of my favorite streets downtown.  

It was not the most financially optimized decision; we could have bought a duplex outside of the GTA, for instance. But it felt like the right decision.

I am betting on my city to return to its former glory by betting on this little condo. It is my tiny investment into a brighter future for all of Toronto.

Changing Friendships

It turns out some relationships were not built to withstand not doing stuff together.

Some people in my life were always a bit difficult, even before the pandemic, but the pressures of the Pandemic and confinement took their difficulties to new heights.

Combined with the inability to go out and DO something and not just talk, and I supposed my own “meh” emotional state, I struggled with navigating the interpersonal turbulences successfully.

On the flipside it was also delightful to discover that some bonds never weaken permanently. During hard times, they just find a new source of nourishment and keep going.

Covid brought a rearrangement of relationships, some positive and some negative. But it is all OK in the end, as the good outweighed the not so good.

Changing Priorities

After a year in confinement, I am surprised that I miss only a small (but important) subset of my pre-pandemic life.

In 2020, I grew my “alone but not lonely” muscle without the access to my usual group of colleagues and friends. I also learned how to just be OK without the constant physical presence of friends and family.

I transitioned from restaurants, pubs and dancing to video chats, walks and camping- without a material drop in happiness.

While I do not want to live like this long term, I am looking forward to discovering new joys in 2021 as we slowly exit the confined state.

Plunging into 2021

Someone on Twitter said what if 2020 is the least crazy year we have moving forward – it is an interesting thought.

But it is probably the “arrogance of man” to think what is crazy to us is what is crazy in general. Pandemics are nothing new. Humanity survived the old ones; humanity will survive this one.

Individually I think the pandemic slowed down our individual lives and allowed us to pay attention to the world at large. And the world is exhilarating. I am even more eager to go out and explore.

Pushing Fitness Beyond Mental and Physical Limits

This is the story of Ryan Keay, who at 38, started on a fitness path that eventually led him to race in Spartan obstacle courses, while shedding 50lbs along the way. In this highly inspiring interview, Ryan and I talk about what made him start and what it took to get to where he is today.

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Five Ways to Level Up Your Life Using New-found Extra Time in Quarantine

If you are currently in the mood to simply stay in your pajamas and check Twitter every 5 minutes or just cut out the world and cuddle your family, then go for it. You do what you need to do to survive some of the worst weeks of our lives. However, if you are looking for some ideas to Level Up during Quarantine 2020, look no further than below! I have compiled 5 ways you can level up easily and emerge as a new you when life outside of the home resumes again.

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Leaving Corporate Life to Become an Independent Consultant

This is the story of Joanne Dong, an independent consultant, currently focused on solving challenging problems in US Healthcare using technology. In this in-depth interview, Joanne and I speak about her journey from growing up in communist China to becoming a consultant and the many pivots she made along the way.

Continue reading “Leaving Corporate Life to Become an Independent Consultant”