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Why the Plan is Bull — Hands-On Strategy & Marketing that Moves the Needle with Neel Singh



What happens when you hand a client a beautiful, well-researched strategy and immediately tell them it's complete bullshit? According to Neel Singh, that's exactly the right move.

In this episode of Scrappy But Successful, Jack Tompkins sits down with Neel Singh — Managing Partner and Founder of Tropoly, a full-stack strategic marketing firm built for complex industries with complex sales cycles. Neel's story is one of the most wide-ranging origin stories we've had on the show: from hand-drawing comic books and video game levels in Vancouver, BC, to graphic design freelancing, to running a restaurant at 28, to scaling a startup from 15 people to 450 and a $36M Series A raise — and eventually to founding Tropoly in 2022.

What ties it all together? A philosophy Neel calls "heads and hands" — deep strategic sophistication paired with the willingness to get scrappy and make things happen in the real world.

From Comics to Consulting: Neel's Origin Story

Neel grew up in Vancouver in a family of creatives — his parents are accomplished writers in Punjabi and English, his extended family includes factory owners, singers, and poets. He describes himself as "the mix of all of that," and it shows.

As a kid, Neel drew comic books, designed his own video games on paper (laying sheets end-to-end across the living room floor), and even drew commercials inside his comics — a creative instinct that he later realized probably foretold his marketing career. He was drawing ads before he knew what advertising was.

School didn't hold his attention — "when I enjoyed the subject, I killed it. Otherwise I'd get bored and fall off." After dropping out of college, his sister pointed him toward Vancouver Film School, where he discovered classical animation. More importantly, he discovered Photoshop — and that changed everything. His ability to digitize his hand-drawn concepts got him into graphic design, and his first real business was born.

Bank Teller by Day, Side Hustler by Night

After freelancing, Neel landed a job at a bank through his best friend — going from teller to business teller to lender over two and a half years. But he never stopped freelancing. He kept two stacks of business cards: the bank's official ones on top, and his own graphic design cards hidden underneath. When clients walked in, he'd eventually slip them the second card. He got in trouble for it. He kept doing it anyway.

Eventually, the bureaucracy of banking — particularly watching the institution reject loan applications from deserving people due to technicalities — pushed him to quit. He and his best friend bought a restaurant at 28. They ran it for two years. Neel sold it on his 30th birthday.

"That's my MBA," he says. Managing cash flows, volatile staff, a drunk chef who wanted to fight him, a full rebrand from Italian café to tapas bar — two years of messy, exhilarating, real-world business education. As Jack put it: you can't learn that chapter in school.

From Scrappy Consultant to Startup CMO

After the restaurant, Neel went back to consulting — brand strategy, rebrands, marketing — picking up hospitality clients through his restaurant network. Then in 2012, a media tech startup of about 15 people found him on Twitter and recruited him to help with a rebrand. He showed up in a hoodie and a hat, had a great conversation with the CEO (whose TED Talk he'd seen), and agreed to consult for a month or two to see how it went.

Nine years later, he'd built out the entire marketing function, helped the company scale from 15 people to 450, and guided them through a $36M Series A and an IPO in 2020. He jumped out in 2021 to launch what would eventually become Tropoly.

The Plan is Bullshit (And That's the Point)

One of the episode's standout moments is Neel describing how Tropoly presents strategy to clients. They do the sophisticated work — market research, pricing models, projection spreadsheets, a clean three-stage adoption plan. Then they hand it over and say: "This is all bullshit, just so you know."

The point isn't that the work doesn't matter. The point is that the moment you go to market, reality doesn't follow the plan. So instead of leaving clients with a static document, Tropoly builds them a scenario planning dashboard — a live tool where the client can adjust the parameters, stress-test the assumptions, and stay agile when things inevitably don't go as scripted.

"It's turned from a sophisticated solid strategy into a playground and a scenario planning tool." That's the Tropoly difference: deep strategy turned into flexible execution.

Brands That Look Small Stay Small

Neel shares two of Tropoly's defining taglines that capture their philosophy perfectly.

"Brands that look small, stay small." This one came out of a rebrand engagement with a 15-year-old company working with enterprise clients — but whose branding still looked like it was done on Fiverr. The perception didn't match the capabilities, and that mismatch was a ceiling. Early-stage companies can get away with it. Growth-stage companies can't.

"Transformative growth." Tropoly isn't interested in tweaking a few buttons and delivering incremental gains. They want to fundamentally shift what a company is capable of — whether that's entering new markets, launching new products, or building capabilities that didn't exist before. "Your company should look a little bit different after we're done working with you."

Who Tropoly Works With

Tropoly's sweet spot is companies doing $5M–$50M in revenue, typically in complex industries with long, multi-touch sales cycles — energy, deep manufacturing, deep tech, food innovation. Their buyers are almost exclusively CEOs and founders who need both strategy and execution, not just one or the other.

They'll turn away clients who just want tactical execution without the strategic foundation. "Then you should probably hire an advertising agency," Neel says. "It's not a fit." Knowing when to walk away from work is — as Jack notes — the ultimate sophisticated move.

The Lightning Round

Books over podcasts. One phone number. Organized chaos on the desk (a dongle here, a convergence point there). And yes — Neel once wrote an entire email in the subject line and sent it to 40 people on his birthday, hungover, from bed. The first reply? "Loud noises." The second? "Must be quite a hangover." We'll let that be the final word on his scrappy credentials.

Connect with Neel Singh

LinkedIn: https://www.linkedin.com/in/neelsingh

Website: https://www.tropoly.io

About Pineapple Consulting Firm

Pineapple Consulting Firm specializes in white-label dashboards and data-driven solutions for businesses of all sizes. Whether you need a franchise dashboard, a CFO-level financial view, or fractional analyst support, Pineapple builds the data infrastructure that helps you make smarter decisions faster.

Explore our services:

  • Franchise Dashboards: https://pineapplecf.com/franchise-dashboards

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