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Shubha Dasgupta

@shubs88

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🏦 NYSE: PAPL 📣 Public Speaker 🏃 Runner

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I’ve learned a lot about running over the last six months, but one of the biggest lessons wasn’t what I expected.

I always thought getting better meant learning how to push harder.

Turns out, I already knew how to do that in many aspects of life, work, relationships etc.

What I needed to learn was when not to push.

To let easy days actually be easy. To take the rest day. To stop turning every workout into a test. To trust the taper when I’m restless and itching to move. And today, to start patiently when everything in me wanted to go faster.

I think that’s been one of the biggest shifts for me.

Progress isn’t always about doing more. Sometimes it’s about being disciplined enough to let the work do what it’s supposed to do.

The race taught me something else too.

A few days ago I was thinking about what I’d do when my mind eventually told me I couldn’t hold the pace anymore.

That moment came.

And what I realized is that I didn’t need to convince myself I could run another 5K.

I just needed to make the next good decision.

Hold the pace. Relax. Get to the next kilometre. Then do it again.

Maybe confidence isn’t about being certain you can do something.

Maybe it’s being okay with the doubt and continuing anyway.

And then there are the people.

Running looks like an individual sport because there’s one name beside the result, but so little of this happens alone.

When you’re surrounded by people who show up, work hard, push each other, laugh together, suffer together and genuinely want to see each other succeed, it changes you.

Their standard starts to become your standard.

I’m incredibly grateful for my coach @weldrickdarren my Runway teammates, my family and everyone who has been part of this block.

1:27:14. PB

Proud of the time. But even more grateful for everything I learned getting there and for the people I got to share it with. by @shubs88

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17

3 days ago

Izzy, 17 years ago today, you came into this world and gave me my favourite name: Daddy.

From the first day, you taught me patience, presence and unconditional love. Being your dad made me want to become the best version of myself, so I could set an example for you.

Today, watching you become your own person is one of the greatest joys of my life.

You are smart, hardworking and determined. When something matters to you, you put in the work and see it through. You know what you want, and you understand that you have a role in making it happen. You have a kind heart, a mind of your own, and the judgment to know when to offer a hand and when to stand your ground.

What makes me proudest is seeing you trust yourself. Finding your voice. Choosing your path. Becoming more fully you.

As you turn 17, I hope you keep that belief in yourself. Be brave enough to go after what matters to you, give yourself room to grow, and remember that you are loved through every part of the journey.

You are a force, sweetheart, and the world is better with you in it.

Happy 17th birthday, Izzy. I’m so proud of who you are, and I’ll always be cheering you on by @shubs88

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10

a month ago

I’m still trying to process what Le Wild Boar meant to me.

I’ve told the stories, shared the photos, laughed about the exhaustion, lack of sleep, chaos and everything that happened somewhere between London and Noyers. But even now, none of that captures the experience, because Le Wild Boar became so much more than a relay.

It was emotional in a way I wasn’t expecting. There were incredible highs, difficult lows and long stretches where we were simply tired, hungry and trying to keep moving. But somewhere inside all of that, something changed.

Friends became family. Family became part of the journey. Strangers in towns and villages welcomed us, encouraged us and, for a few moments, became part of our story.

What keeps coming back aren’t always the big moments. It’s the hundreds of little ones in between. The laughter in the middle of the night when nobody had slept. Someone handing another person food or water. Waiting on a dark roadside for a teammate to appear. The conversations in the RV. The silence when everyone was exhausted. The check-ins when someone was struggling. Watching one sunset disappear and being awake to see the next sunrise.

They were ordinary moments on their own, but together they created something extraordinary.

For a few days, life became incredibly simple. Run when it was your turn. Help when someone needed you. Eat when you could. Sleep when your body allowed it. Laugh whenever possible and keep moving forward.

There was something almost spiritual about being stripped down to that. No titles. No distractions. No pretending. Just people sharing something difficult, taking care of one another and experiencing every emotion with it.

The distance wasn’t the point. The running wasn’t the point.

It was what happened between us while we were doing it.

The trust. The vulnerability. The laughter. The struggle. The feeling of being completely present and realizing people you cared about somehow meant even more on the other side.

I may never perfectly explain Le Wild Boar to someone who wasn’t there. Maybe I don’t need to.

Some experiences don’t simply become memories.

They become part of who you are. by @shubs88

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5

a month ago

Every so often, a moment happens that you never planned for but somehow know, that you will remember forever.

For me, that moment happened in Étrépilly, a village in France, in the middle of a journey filled with enough stories to write a book

We had just come off another running shift. Legs tired, I was hungry and after no sleep, I knew I should climb into the RV and close my eyes.

But outside was the Perseid meteor shower.

Sleep, eat or experience something I may never see like this again.

Sleep could wait.

I stepped outside into a darkness that felt different from home. No lights washing out the sky, no noise, just a tiny French village asleep around us and an enormous black canvas overhead.

At first, I saw almost nothing.

So I stood there. Tired. Hungry. A little delirious. And stared.

Slowly, my eyes adjusted. A few stars became hundreds. Planets appeared between them. The longer I looked, the deeper the sky became, until it felt less like I was looking at the universe and more like I was standing inside it.

Then a streak of light cut across the darkness.

A shooting star. Then another. And another.

Soon we were calling them out, laughing when someone looked a second too late and waiting for the next one.

For those few minutes I forgot I was tired. I forgot I was hungry. I forgot about the kilometres still waiting for us.

There was only the darkness, the stars and the people beside me.

I thought about how vast the universe is and how small our lives must seem within it. But somewhere in that thought, I stopped looking up and started looking around.

At my friends. At the runners coming back from the road. At the people sleeping, driving, navigating and waiting their turn.

Somewhere between London and Noyers, through exhaustion, laughter and shared kilometres, we had become more than a group running a relay.

The meteor shower was incredible, but it wasn’t only the stars that made that night unforgettable. It was being there, exhausted and present, sharing something none of us had planned for.

And yes, I definitely made my wish.

Everything that mattered to me in that moment wasn’t millions of kilometres away. It was standing right besi by @shubs88

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7

2 months ago

La création, créer.

C’est l’acte de concrétiser une idée, une œuvre d’art ou l’univers lui-même, en leur donnant une forme réelle.

C’est exactement ce qu’était Lewildboar : un projet passion devenu réalité.
Lorsque ma femme et moi avons envisagé d’acheter une maison à Noyers, en France, je me suis dit : « Si je me lance, je dois faire découvrir ce lieu médiéval merveilleux et surréaliste à d’autres personnes. » Et quoi de mieux pour cela que d’y organiser une course ?
Nous avons donc acheté la maison de nos rêves, en avons fait un véritable foyer et avons créé quelque chose d’unique.

Nous avons couru sous une chaleur dépassant les 40 degrés, en plein soleil, dans l’obscurité (au sens propre comme au figuré) et au milieu de nulle part. Tout cela était magnifique.

Rien de tout cela n’aurait été possible sans la formidable équipe que j’ai réunie. Chacun a dépassé toutes les attentes pour concrétiser ce projet. Nous avons commencé comme coéquipiers, puis l’amitié nous a transformés en une véritable famille. Tout cela grâce, en particulier, à ma femme exceptionnelle.

Et que dire du soutien du village !?! Il a dépassé tout ce que j’aurais pu imaginer. Ce lieu unique s’est mobilisé pour nous accueillir : habitants, commerçants, amis, mairie et municipalité.

Merci Noyers.

Je ne veux pas redescendre de ce petit nuage. Mais je le dois, si je veux faire de la place pour créer à nouveau quelque chose d’épique.

Registrations for next year coming soon

#runningtherunway #fuelyourgoals #courseapied #france #runnersofinstagram by @shubs88

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6

2 months ago

Creation, to create.

It is the act of making, building, or shaping an idea, art, or the universe into a real form.

That is what Lewildboar was. Passion project made real.
When my wife and I thought about buying a house in Noyers, France I thought, if I do this, I must bring people to this wonderful, surreal, medieval place. What better way than to run here?
So we bought our dream house, made it a home, and created something special.

We ran through 40+ degree heat, sunshine, darkness ( both literal and metaphorical) and the middle of nowhere. All of it beautiful.

None of it could have happened without the best team of individuals I’ve put together in a long time. Everyone exceeded expectations to make this come true. We started as teammates, and moved through friendship to become a family. Especially thanks to my perfect wife.

And then the support of the village !?! More than I’d imagined. This special place came together to welcome us, from residents to business owners, friends, the town hall and the mayors office.

Merci Noyers.

Another post in French will follow shortly (en Français bientôt )
Stay tuned for registrations for next year!

I don’t want to come back down from this cloud. But I must, if I’m to make room to create something epic again. #running #boncourage #noyerssurserein #courseapied runnersofinstagra by @shubs88

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9

2 months ago

After 600km of running on no sleep and gummies how do you keep your team spirit up? A baton challenge of course.

A little delirious, incredibly hot but still going strong. Running builds community, health and memories that last a lifetime.

Which baton pass do you think was the best?

#UltraRunning #RunningCommunity #RunnersOfInstagram #RelayRunning #UltraMarathon by @shubs88

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22

2 months ago

18 years married today. ❤️

Every year I write one of these posts for my wife (and I). Partly to celebrate us, but also because I love the idea of leaving little time capsules along the way. This is for others to read, it’s for us, when they pop up on our feeds each year and for when we’re 90 years old and want to remember how we felt throughout the years. It’s a chance to stop for a moment, look around, and reflect on exactly where we were in this life we’ve built together.

Funny enough, we’re spending our anniversary apart today. But yesterday, we had what I can only describe as a magical day together in Paris.

We walked. We wandered. We laughed. We ate. We met with old friends and made some new ones in a couple on the honeymoon. We sat and watched the world go by. There was no big plan or grand moment that made it special. It was just us.

I think about the couple who we met at lunch, the kept glancing at the food we’d ordered and finally mustered up the courage to ask if the dishes were recommended. we asked them if they’d like a taste (because that’s who we are). The new husband looked mortified as his wife agreed and joined us in sharing bites off our plate. We all then laughed and they ordered the same items. It was a victory.

That’s our marriage, giving everything we can to everyone around us but most importantly each other.

18 years of marriage. More than 23 years since we first found each other. We’ve grown up together.

And through all of the versions of ourselves that have existed along the way, I still really love the simplicity of just being with you.

Yesterday in Paris reminded me of that.

There are a million things I could write about what marriage means after 18 years, but maybe this year I’ll just leave this little time capsule here:

August 10, 2026.

18 years married.

Still wandering the world together. Still laughing. Still dreaming. Still choosing each other.

And still my favourite person to get lost with.

Happy anniversary, Donna. ❤️ by @shubs88

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45

2 months ago

🏡 If you're a Realtor, understanding reverse mortgages could help you better serve clients and uncover new opportunities.

Join Pineapple CEO Shubha Dasgupta and industry lending leaders as they discuss how home equity is changing retirement planning, family wealth conversations, and real estate decisions for older Canadians.

📅 June 24, 2026
⏰ 10:30 AM – 12:00 PM ET
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Connect with industry peers, hear real-world insights, and stay ahead of an evolving market.

🔗 Register in the link in our bio by @shubs88

18

0

4 months ago

All winter we ran when almost nobody else was outside.
Pitch black. -25 windchill. Snowbanks. The kind of days where you stand at the door negotiating with yourself.

Some runs were quiet and alone. Some were laughs. Some were therapy sessions and some were with the team. We talked about life, stress, families, work, doubts… and then we’d run.

Today every single person in the group ran a PB.

That’s not a running story. That’s a life story.

Because what really happened wasn’t fitness. It was trust. We learned patience. We learned to stay when it was uncomfortable. We learned that progress doesn’t come from one heroic day, it comes from a hundred ordinary ones you almost skipped.

I’m honestly just grateful.
Grateful for the encouragement, the accountability, the friendships, and the quiet belief we gave each other on days when one of us didn’t have it alone. And grateful to our coach @weldrickdarren who uses us all to be better.

If you’re at the start of something right now… anything… fitness, business, health, healing, a new chapter in life… you don’t need a perfect plan. You need consistency and people who help you keep your promise to yourself.

Show up long enough and one day you won’t recognize the person you became.

Proud of this team. Love this crew. by @shubs88

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6

7 months ago

As we close out 2025, we’re feeling incredibly #PineappleProud 🍍

The past 365 days were filled with unforgettable moments shared with our Pineapple network members, valued lender and vendor partners, and our amazing team. From kicking off the year at the Pineapple Awards, to Horizons+ in Jamaica, spirited pickleball tournaments, weekly trainings, prime and alt/private lender speed dating, MPC Ottawa, and our annual Holiday Party—every moment reinforced what we already know.

Pineapple is built on community, connection, and people who genuinely care. The energy, collaboration, and heart we saw all year long proved one thing loud and clear:

THE BEST PEOPLE AND THE BEST BROKERS JOIN PINEAPPLE

Thank you to every individual who showed up, partnered with us, learned with us, and celebrated alongside us in 2025. We’re so grateful for each of you—and we can’t wait to do it all again.

Here’s to 2026… a year to remember 🥂✨

Happy New Year from all of us at Pineapple 🍍💛

#PineappleProud #BestBrokers #BestPeople #PineappleFamily #ThankYou #Hello2026 by @shubs88

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3

9 months ago

2025 was special and so are you. What’s one photo from this past year that’s special to you and really stayed with you?

A moment.
A person.
A place.

Would live to see what made this year special for all of you.

If you’re open to it, share it below. by @shubs88

14

0

9 months ago