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The Effortless Podcast

Dheeraj Pandey, Amit Prakash

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Join longtime friends and entrepreneurs Dheeraj Pandey, founder of DevRev, and Amit Prakash, co-founder of ThoughtSpot, on The Effortless Podcast as they explore the art of building, innovating, and thriving in tech—without losing sight of what really matters. With decades of experience scaling companies and navigating risk, Dheeraj and Amit tackle tough questions for modern entrepreneurs: How can startups feel effortless in the face of endless challenges? What does “long-term greedy” mean w ...
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Have you wondered what it takes to thrive in the accounting industry? Or how the experts established their successful careers? Learn from industry experts with Canopy. In each episode of the Practice Success Podcast, Canopy takes a deep dive with accounting professionals, exploring their career trajectory, extracting advice for firms, and discussing the latest trending topics.
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Every founder has 1 goal: find product-market fit. We interview the world's most successful startup founders on the 0 to 1 part of their journeys. We've had the founders of Reddit, Gusto, Rappi, Glean, Cohere, Huntress, ID.me and many more. We go deep with entrepreneurs & VCs to provide detailed examples you can steal. Our goal is to understand product-market fit better than anyone on the planet. Rated one of the world's top startup podcasts.
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Instigators of Change is a Khosla Ventures podcast that explores innovative ideas, the people who come up with them, and those who invest in them. Our guests are the outliers, creators, mavericks — those who imagine differently. They build companies that alter transportation, retail, food, energy, entertainment, space. And when they succeed, we cannot imagine life without them. Tune in to hear about non-obvious ideas from inspiring people. The podcast is hosted by Kara Miller, former host of ...
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Send us your thoughts or what you want to hear more about! In this episode of the Canopy Practice Success Podcast, KC Brothers sits down with Dheeraj Pandey, co-founder and CEO of Credfino, a fast-growing firm that supports more than 100 accounting and tax practices across North America. Dheeraj shares how Credfino started during the pandemic, how …
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Alex built the original Snapchat filters-- and sold his company to Snap for $166M. Then he left to start Higgsfield. The company just raised a $50M Series A to help brands create AI-generated video ads at scale. We go deep on why he thinks Adobe is in trouble, how top advertisers are already producing 10,000+ ad creatives a year, and why the compan…
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Send us your thoughts or what you want to hear more about! Editor in chief of Accounting Today, Dan Hood, joins host KC Brothers to look back at two decades of “whispers” in the profession that either reshaped accounting or quietly disappeared. From the long, painful march to the cloud to the hype cycle around blockchain, Dan unpacks what actually …
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Eric spent 30 years in cybersecurity. Built and sold an MSSP to private equity for hundreds of millions. Then he started Tenex and hit $43 million in revenue in ONE YEAR. This isn't theory. This is a founder who's done it multiple times breaking down exactly how AI-native companies are about to eat every services industry alive. If you're building …
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Carta's Peter Walker is back with the freshest data on what's actually happening at the early stage—and it's not what you're reading on X. While headlines scream about record-breaking rounds, the reality on the ground tells a different story. Seed deals are down. Time between rounds is stretching. And there's a brutal divide between the companies g…
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Alex and his co-founders spent 2018 pitching parking lot owners on computer vision tech. Every meeting ended the same way: "Cute startup, come back in 30 years." So they did something else—they bought the parking operators and implemented the AI themselves. VCs called them delusional. But today, Metropolis has 20 million members and adds 1 million …
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In this episode of The Effortless Podcast, Amit Prakash sits down with Abhay Parasnis, Founder and CEO of Typeface, to explore how AI is reshaping marketing, creativity, and entrepreneurship. Abhay reflects on his incredible journey from building foundational internet technologies at IBM, leading Microsoft’s Azure transformation, driving Adobe’s sh…
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Amit walked away from being President of 1-800-Flowers after scaling it from $500M to $2B because he saw smart people trapped in dumb systems. His insight: half of global GDP is 90% manual work—salespeople entering data instead of selling, technicians reading manuals instead of fixing. He started Instalily in Spring 2023 when everyone said AI agent…
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Wayne tested flight insurance over a single weekend with a WordPress site and Google ads. When people tried to pay, he showed a fake error message. The result: 15.9% conversion. That validation led to Sure, now powering insurance for Tesla, Toyota, and MasterCard. But the journey was brutal. Wayne worked solo for a year, burning through savings in …
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Matt sold his first company at 19 and made $100K. He sold his second at 21 and made $800K. A couple years later, he launched Clover and grew it to $8M ARR in 6 months. His secret? Insane distribution. His formula is to ignore quality—and engineer quantity instead. While everyone obsesses over viral content, Matt posts 1,000 videos across 333 accoun…
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Russ has started and sold multiple companies over 30 years, but his Dynamic Signal journey will change how you think about product-market fit. They had $5M ARR selling influencer marketing software. Then Russ told investors to pretend the $5M didn't exist and bet on a $200K pipeline instead. That pivot led to 600 Fortune 2000 customers and an exit …
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Harish spent 9 months building Deliver and could barely get 10 customers. The product worked. Merchants liked the fast delivery promise. But nobody was signing up. Then he made two changes—and scaled to $100M in revenue in 2 years. Shopify acquired them for over $2B. Harish says it wasn't about finding product-market fit. It was about finding produ…
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Send us your thoughts or what you want to hear more about! Guest: Darren Root, CPA Host: KC Brothers Topic: Darrens Book Building The Simple Firm In this episode of Canopy Practice Success, host KC Brothers sits down with Darren Root, CPA, author, and co-founder of Rootworks and Better Everyday, to explore how firm owners can simplify their practic…
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Dheeraj built Nutanix into a $20B public company—then walked away to start DevRev. He just raised a $100M Series A. This episode breaks down why most founders "sell and run" (chase new logos instead of delivering value), why that strategy fails, and how Dheeraj thinks about building platforms with use cases instead of just features. He explains why…
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Simon spent 10 years at Shopify scaling databases to millions of requests per second. Then he discovered vector databases were so expensive that companies couldn't launch AI features. So he solved it. When Cursor emailed about their crushing costs, Simon flew to San Francisco unannounced. They migrated their entire workload within a week, cutting t…
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Guy spent 2 years and $4M building Snyk to $100K ARR. Thousands of developers loved the product. They just wouldn't pay. Then he figured out the problem: he had product-user fit, but not product-buyer fit. Developers loved Snyk. Security teams (the actual buyers) didn't care about it. The distance between user and buyer was killing him. So Guy spen…
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Amar is a 5x founder who helped birth Tinder (it was the 10th project—after the first 9 failed), then sold his next company to Ford for putting a platform in every single vehicle they make. But the wildest part? He got Ford to commit in under a year by doing something most founders would never do: he asked for SO MUCH money that only the CEO could …
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Send us your thoughts or what you want to hear more about! In this episode of Canopy Practice Success, host KC Brothers sits down with Ashley Carroll, founder of Operations House, to explore the balance between people, process, and profit. Ashley’s journey is one of grit, growth, and giving back. From growing up below the poverty line to leading a …
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Ben Alarie spent 8 years building Blue J with "partial product market fit"—real customers, real revenue, but no real market pull. Then he made a bet that would either kill the company or 10x it: he put the existing product in maintenance mode and gave his team 6 months to rebuild everything from scratch using a technology that barely worked. Two ye…
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Dean thought he'd have to bootstrap Axonius because no investor would fund a solution to a problem that had existed for 20 years. He was wrong—they've raised $500M. The breakthrough came when a Fortune 500 company was actively being hacked by Chinese state actors. Their first customer almost said no—they had 20 bugs during the POC. But Dean's team …
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Casey turned hackers into a marketplace and built Bugcrowd to $180M+ raised. But the real story isn't about cybersecurity—it's about how he validated a two-sided marketplace with almost no product, refined his pitch by literally testing it on Uber drivers until it clicked, and cracked the code on category creation when everyone thought hackers were…
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Zach spent 8 years at Google leading engineering for Google Docs, then left to build a photo sharing app with zero go-to-market plan. Reality hit hard: "At Google, anything you launch gets millions of users. At a startup, the challenge isn't building—it's getting anyone to care." After writing a brutal postmortem documenting everything that went wr…
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Send us your thoughts or what you want to hear more about! In this episode of Canopy Practice Success, host KC Brothers welcomes two leaders who have been shaping Client Advisory Services for years: Deneen Dias and Christine Triantos, co-founders of Infinite Ties. From their early-adopter journeys to launching a new venture, Deneen and Christine sh…
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Alex had $2,000 in his checking account when Microsoft acquired his last company. For years, he paid himself $30K while his friends made six figures at corporate jobs. He had only 2 months of runway for 18 straight months. Then retail media exploded and everything changed—he went from grinding against the current to riding a wave. After selling to …
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Brett had a drug dealer's car for 13 days. By day 11, the death threats started coming. This is the reality of building ServiceUp, the "DoorDash for auto repair." Brett literally stole DoorDash's entire playbook—city launches, three-sided marketplace, everything—but discovered even if he got 90% right, 10% of B2C customers can end you. He raised fr…
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What drives real product growth—launching new features, or helping existing ones land? In this episode of The Effortless Podcast, Dheeraj Pandey and Amit Prakash sit down with Ken Rudin, former Head of Growth at Google, Facebook, Zynga, and ThoughtSpot, to unpack 15 years of lessons at the intersection of analytics and product. Ken shares the story…
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Arnold Schwarzenegger mastered three completely different fields—bodybuilding, acting, and politics—with one simple philosophy: reps, reps, reps. This solo episode reveals why speed of execution is the only real moat for early-stage founders. One founder takes an idea from conception to signed customers in three weeks. Another takes six months. The…
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Send us your thoughts or what you want to hear more about! In this episode of Canopy Practice Success, host KC Brothers sits down with Dave Spence, a CPA turned financial planner with decades of experience in both public accounting and wealth management. With six years in public accounting, 18 years at AXA Advisors, and 15 years at LPL Financial, D…
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Aviv spent months walking construction sites carrying tools for managers just to understand their problems—speaking to customers is "bullsh*t"—you need to work beside them to see reality. His company Buildots had a working AI product that tracked construction progress perfectly, but 90% of users got zero value from it. Until he made one key change …
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Shensi cold messaged 50,000 engineers to build Merge. She worked 9am-9pm every day, gave her first customers two months free to prove herself, and refused to hire anyone remote—even during peak COVID. She purposefully didn't collect a single dollar of revenue until she knew she could hit $1M in a months. "Startups are all about momentum." She lost …
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Eldon put a $150K line of credit on his house to start eSentire in 2001. No VCs would touch him—they didn't understand services businesses. He worked 12-hour days, 7 days a week for 7 years to hit $1M in revenue. His co-founder coded while he flew to New York on $99 JetBlue flights from Buffalo to save money. Then something clicked: they brought in…
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Send us your thoughts or what you want to hear more about! Summary In this conversation, Michael Ly, founder of Reconciled, shares insights on the importance of listening in sales, the unique structure of his accounting firm, and how to build trust with clients. He emphasizes the need for accountants to ask the right questions and focus on client n…
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Soham spent 6 months building AI that would auto-generate integrations between any software. He locked down Glean as an early customer because he had friends there. And it failed completely. So he pivoted. This time, he refused to work with friendly customers who knew him. Instead, he did 10-20 calls per day with strangers who would tell him his pr…
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Sahil was 18 when TechCrunch published a hit piece calling him a copycat. His co-founder Aaron was 16. They'd just raised $6 million from YC and top VCs for their crypto startup, then got subpoenaed by a state government and watched their business implode. So they fired everyone, moved back to their parents' homes, and spent months cold-calling den…
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Jon spent 3 years building Gamma with barely any traction—just a few hundred users after burning millions. Then ChatGPT dropped. In desperation, he pivoted to AI-powered presentations in March 2023 with one year of runway left. What happened next was insane: Paul Graham publicly mocked their launch tweet calling it worthless—then it went viral. The…
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Soham co-founded Rubrik by taking what he learned from building Google's data center tech to enterprises desperate for cloud migration. Two quarters later, he hit $1M ARR. And a few years later, a $16B IPO. Soham breaks down why paid pilots beat free trials, how to sell enterprise hardware before it works, and why early customers become your bigges…
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Is AI truly delivering ROI, or are we just “burning tokens”? In this episode of The Effortless Podcast, Amit Prakash and Dheeraj Pandey unpack the MIT report that sparked debate on AI’s real impact and revisit the timeless dilemma of whether to build or buy. They frame the conversation through a pyramid of adoption—from global enterprises with engi…
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Stéphan bootstrapped AODocs to $55M in revenue and 250 employees without taking a dime of VC money—while competing directly with venture-backed competitors. Starting as a services company in 2012, he spotted the cloud migration wave early and built document management for enterprises moving to Google Workspace. In this episode, Stéphan breaks down …
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Send us your thoughts or what you want to hear more about! In this episode, KC Brothers interviews Kane Polikoff, a seasoned expert in accounting services, discussing his extensive career journey and the evolution of Business Process Outsourcing (BPO) to Client Accounting Services (CAS). Kane shares insights on overcoming imposter syndrome, the imp…
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How do you build a successful AI company in today's landscape? Do you go broad and build a horizontal platform for everyone, or do you go deep and create a vertical solution for a niche market? In this episode, Dheeraj Pandey and Amit Prakash dive into one of the most critical strategic challenges facing founders today. They explore the paradox of …
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Andrew bootstrapped Wrike and grew it from 0 to a $2.2B exit by doing the exact opposite of what every startup book tells you. No pivots. No talking to customers before launch. No narrow niche. Just 17 years of relentless focus on one problem while everyone else was pivoting every 18 months. In this episode, he breaks down exactly why bootstrapping…
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Peter Walker from Carta drops the hard data every founder needs. Based on actual cap table data from 1000s of startups, this Q2 update reveals the brutal new reality. It takes 2+ years to go from seed to A (up from 1.6), you need 3X the revenue you used to, and if you're not AI, you're getting half the attention. But there's good news too—teams are…
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Hedra CEO Michael Lingelbach breaks down how his generative video app went from zero to millions of users and an eight-figure run rate in months — then deliberately slowed down to rebuild a V2 that enterprises would pay for. We dig into the prosumer-to-pro upsell, why free users are a false signal, and how a creator-seeded launch can outpull ad spe…
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Ross went from lawyer to self-taught engineer to CTO at a 1,600-person unicorn—then quit to build Wordsmith AI. In 18 months, he's raised $30M and grown to mid-single-digit millions in ARR by doing everything differently. He tested co-founders by starting fights. Built in Slack for 10 months before adding a web interface. Kept his team at 8 people …
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Send us your thoughts or what you want to hear more about! In this episode, KC Brothers interviews Ryan Lazanis, founder of FutureFirm, discussing the challenges accountants face in building scalable practices. Ryan shares his journey from running an online accounting firm to coaching others on achieving freedom and growth in their businesses. The …
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Rick built Persona into a $100M+ ARR unicorn, but he never thought it would work. In fact, Rick started Persona believing it would probably fail, and that mindset might be exactly why it succeeded. In this episode, Rick reveals how a casual project with zero expectations turned into a billion-dollar business, why early-stage startups should avoid h…
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Neil Patel just flipped everything you know about startups upside down. He says product-market fit is overrated, giving away your software for free can make you rich, and the real secret to scaling isn’t charging customers—it’s monetizing the leads your free product generates. Neil breaks down his playbook on how startups can leverage free products…
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Roy Lee went from getting kicked out of Harvard and Columbia to building Cluely, one of the fastest-growing AI startups ever—going from 0 to $5 million ARR in just 3 months. We go deep on Roy’s playbook for using controversy, virality, and content to get millions of views—and millions in ARR. You’ll learn why Roy intentionally designs content to sp…
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Mary Beth Snodgrass shares the raw and real story behind Healthiby—an innovative healthcare startup that succeeded in delivering measurable health outcomes but ultimately didn't take off. Hear firsthand what went wrong, from unclear payer dynamics and sales friction, to macroeconomic shifts and storytelling gaps. This episode pulls back the curtain…
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